By: Stella Satin
I may not be very big, but while I was Cindy’s boyfriend I felt over ten feet
tall.
She’s my ideal woman. Tall and athletic. Kinda bossy now but - I kid you not -
when she’d take my arm when we’d go out on a date, I was the proudest guy in the
world – knew damn well that just about every guy that saw us was jealous. Okay,
I’m well aware that with me being reasonably well off, this was a major
attraction for Cindy, but I didn’t mind – hey, she was honest about that – and
everything else too – another thing that made her the most attractive girl in
the world to me.
But I was too much in love with her, and probably made it too obvious because I
guess she saw that she’d some sort of power over me and started to try and see
just how much she had – and probably wondered how far she could push it.
It started off in small ways. We’d finish making love and she’d look up at me
and say, “Hey Mike? Not one of your better performances, you know? Think you
could come on a little stronger? Last a little longer? Be a little more
macho?”
I started trying to do as she wanted, but she’d just laugh at me and say things
like “You’re not much of a man, are you Mike? Maybe I should start calling you
Michelle?” Then she’d laugh when I’d get indignant, then pull me into her arms
and fondle me. “Oh, I’m only teasing, you silly little thing!”
One night she was in a bit of a cranky mood. I was waiting for her to get ready
to go out and have dinner with me. “C’mon Cindy! For goodness sake! Would you
hurry up? Our dinner reservation’s for seven thirty and you’re making us late!”
She was sitting in front of her dressing table mirror, just applying the
finishing touches to her makeup and I saw the smoldering look she gave me from
the mirror, but then she gave me a big phony smile. “Why don’t you come over
here and sit beside me, sweetie?” she purred.
There was something in her smile that scared me, but I really couldn’t deny her
anything. “Okay!” I grumbled. “If it’ll help you get finished, who am I to say
no?” I crossed the room and she slid over to one side on her little bench so
that I could sit beside her. She put one of her arms around me and, for the
first time ever, showed me how strong she was by squeezing me to her side. I
let out a little gasp of surprise and pain – hell, it felt as if my ribs were
cracking!
“Is big, mean, Cindy hurting her little Mikey?” she crooned.
“Hey! Of course not!” I said, trying to maintain my macho image.
“Wonderful!” she said, then increased the pressure! “Oh, I just feel like
loving you to death! But know what, little Mikey?”
“What?” I gasped.
“What’s the matter? Are you sure I’m not hurting you?” she teased.
“Well, maybe a little bit,” I admitted.
She eased the pressure off and kissed the side of my cheek. “I’m sorry darling.
You just feel so soft and nice. Vulnerable – and I like that. Makes me feel
kinda sexy, you know?”
“Me too!” I said, squirming a little because she was still holding me tightly.
“But I have a problem tonight sweetie,” she said sorrowfully.
“Period?”
“Nah. I just have a confession to make.” She started squeezing me tighter
again. “And I’m not sure that you’ll keep on loving me.”
“Oh Cindy!” I managed to get out. “I’ll love you forever! I want to get
married!”
“Aw! But you might not want that after I tell you my little secret.”
“Never!” I said, and the pressure relaxed a little.
“Okay! Now promise you won’t laugh!” she said.
“I promise.”
“Well, you probably noticed that I’m in a little bit of a bad mood tonight?”
“Maybe a teeny bit,” I answered.
“Well, I am. And it’s because I feel randy! Need sex really bad!”
“Well? Here I am, ready, willing, and able!”
“Oh you’re SO nice. But you see sweetie, sometimes I get an awful urge to make
love to a woman! And right now, I got that urge – so bad!”
I tried to shrug. “Must admit that I can’t help you there Cindy.”
She took her arm away from my shoulders then cupped my face in her hand, turned
me to look directly into her eyes. “You sure?” she asked softly. “Didn’t you
just say you were willing?”
“Yea – but I’m not a woman Cindy.” I tried to laugh, although I didn’t care for
the way the conversation was going. Felt decidedly uneasy.
“I know that, silly. But hold on a minute! What do you think of this?” And she
was holding an opened bottle of perfume under my nose.
“Not bad,” I said.
She put it back down and came up with another. “Well? What about this?”
“Better. Much better.” Then I squealed. “Hey Cindy! What’re you doing?”
“Hush,” she said and continued to dab touches of perfume behind my ears, on my
wrists then at the hollow below my neck. “There! Wasn’t that easy? Now you
smell like a girl! And know what? Cindy just loves the way you smell now. Want
to be Cindy’s girl?” She was caressing me now, then she kissed me firmly on the
lips. “Want to come to bed with Cindy?” she asked seductively.
“Oh yes!” I sighed – meaning an answer to her last question..
“Oh, THANK you so much Michelle!” she giggled though, with her voice being deep,
it didn’t sound too girlish – if you know what I mean.. “But if you’re to be my
girl? A little bit of makeup maybe?”
“Hey! Wait a minute! I didn’t mean . .” I couldn’t say anything else because
she’d taken a hold of my chin and was squeezing my mouth open. Staring coldly
into my eyes. “You just said that you wanted to be my girl Michelle. Now listen
up! I don’t want you to be a prick teaser! No sir! Worst kind of girl there
is! Now tell me Michelle. Tell me that you’re not a girl like that!” She
eased up the pressure.
“I’m not.” I mumbled.
“Not what, Michelle!”
“A girl like that.”
“So you want me to make you pretty now?” She asked then paused when she saw my
expression. “Aw come ON Michael! It’s just a game! Lighten up!”
To tell the truth? I actually did feel that I was getting aroused. The smell of
perfume lingered in the air. Okay – it was ME that was wearing it, but it was
sexy. The way she’d held me was probably uncomfortable, but there was something
erotic in that as well. But when she was looking at me commandingly, I felt I
could refuse her nothing. Plus? She was right – it was only a game after all,
wasn’t it? “Okay. I’m sorry,” I said shyly.
“Good girl! Let’s do it!” she said.
She was fastidious about the way she put the makeup on my face.. Didn’t put too
much of anything on but after she shaped my eyebrows a little, she applied
foundation, eye shadow, blush, mascara, touched up my eyebrows, then applied a
nice red lipstick, then outlined my lips in a darker shade, using a small brush,
I bore very little resemblance to a male.
“There!” she said in a businesslike tone. Then she applied a touch of her own
lipstick, pursed her mouth a little. “Okay Michelle Let’s go! I’m hungry!”
“Huh? Go where?”
“Out to eat – you silly girl! Weren’t you just nagging at me to hurry up a
little while ago? Here! Carry my purse for me, would you?”
“I can’t go out looking like this – and carrying a purse!” I yammered.
“Would you rather I put you in a dress? That make you feel more at home? If
you don’t hurry up, that’s exactly what I’ll do. Coming – or not?”
“But Cindy? You said that you were randy – and that you wanted us to go to
bed!” I complained as she was leading me out of the front door.
“So? The night is young! Later will do. Come on Michelle!”
In her parking structure she opened up the passenger door in my car, then
drove. Made me sit with the handbag on my lap for anybody to see, “Like a young
lady should,” she laughed. Actually made me take out her compact and powder my
nose at a stoplight I felt such a fool when I saw the carload of teenage girls
stopped beside us pointing and laughing at me. I was really glad when she
finally took me into a nice quiet, dark combination bar and restaurant –
although she made me link my arm into hers as she escorted me inside. I blushed
a lot when she referred to me as Michelle a number of times in front of our
waitress then pulled my chair out for me at our table.
It wasn’t until we’d been in there for a while that I realized it was a lesbian
bar and that no one was paying the slightest attention to us. Didn’t even draw
any funny looks when we danced on the small floor – even though it was her that
did the leading.
She was very gallant and even though I was embarrassed at first, I started
feeling flattered at her compliments and how her hand would brush against my
thigh or how snug and secure I felt as she took me in her arms and held me close
while we danced. By the time she had me back at her apartment, I was feeling
nice and sexy. Objected of course when she loaned me a pair of baby doll
pajamas to wear to bed, but she just scoffed at me. “You’ve been a good little
girl all night. Don’t be changing now!” she warned me gently.
When she took me to bed, she demanded that I act all soft and compliant and I
did. As she finally climbed on top of me and inserted my erection inside of
her, I actually felt relieved. For once, I wasn’t having to perform to a slew
of taunting comments about my masculinity or lack of it. Instead, she was
kissing and fondling me – and saying how pretty I was. She had told me not to
ejaculate, but I couldn’t help it. Came into the condom she’d put on me.
“Is that you coming? After I told you not to?” she asked from above me.
“I’m sorry. Couldn’t help it.” I said sleepily.
“Naughty girl! Bad girl!” she said – and seconds later, I was over her knees,
my panties around my knees, her hand falling on my buttocks and spanking me as I
yelped and squealed.
“There now Michelle! You’ll remember after this that when Big Cindy tells you
not to do something? You won’t do it, will you?”
It was the first time I ever heard her refer to herself in that manner, but I
knew enough to respond properly. “No, Big Cindy,” I said weepily.
She pulled me around and sat me on her lap. “Well Michelle? You didn’t make a
very good girl tonight. But you’ll do better next time, huh?”
My ass still smarting from the spanking, I wasn’t taking any chances. I nuzzled
into her neck. “I’ll try Big Cindy. I’ll try.”
“For your sake? You’d better,” she told me ominously.
But it was a few weeks before she wanted a girl again. In the meantime, she had
stopped allowing me the upper position when we made love and would laugh at me
when I’d try to initiate sex. Kept criticizing my performance as a man – and
even the size of my member – even called it my “clit” a few times. She was
sweet to me at times, but it often had a big percentage of mockery in it. Once
she swept me up cradling me in her strong arms and carried me to the bedroom
where she made love to me, but she only talked baby talk to me all that time.
Then came the night when she felt I should be her girl again. This time when we
went to the lesbian restaurant, I wore a pretty white blouse under my jacket.
Naturally, she made me wear makeup and carry a purse – a smaller one this time
and, as she remarked, it went with my outfit much better. That night she had me
sit around and watch TV with her when we got back to her apartment – made me
wear a dainty peignoir over my baby dolls and sit on her knee while she fondled
me. Again, I got over excited and came. Got another spanking, then was given a
new nightdress and peignoir to wear, then made to rinse out “my” baby dolls –
and some of her lingerie.
She made love to me in bed that night with me again playing the role of the
woman. I didn’t get spanked this time because I was able to hold myself from
exploding until she gave me permission.
The following morning she had me do some housework, then iron the lingerie I’d
laundered the night before. “If you can’t be worth a shit in bed as a man – OR a
woman - you can at least do something useful,” she told me. Naturally, I was
somewhat indignant in being talked to in this manner, but didn’t want to raise
any kind of fuss so kept quiet.
Over the next few weeks, I learned that she really appreciated me doing her
housework. I can’t say that I liked it, but it seemed to be some protection
from being constantly criticized and demeaned. Although one time when she was on
the phone while I dusted, I heard her make some comment about how she’d always
felt that pansies made great housemaids while she smiled mockingly at me. From
then on, she demanded that I wear frilly little aprons that she’d bought “just
for you” while I did the housework.
But then, one night, she delighted me. I had been doing the after dinner dishes
when she came into the kitchen, smiled and took a hold of my hand, Pulled me
into the living room, then sat down Had me sit on her lap. “You know Michael?
You’re not very good as my girl. You don’t like it, do you?”
I was a little nervous about what her reaction would be if I told the truth, but
she seemed to know what my honest answer would be, so I prevaricated a little.
“Well, not really. I suppose it’s just because I haven’t got the hang of it
yet.”
She nodded calmly. “Fair enough. You tried, couldn’t hack it. That’s it. You
don’t need to be my girl any more.”
I was ecstatic for a few seconds, until she added. “May as well tell you. I’ve
got a real girl now that can take care of me in that regard. Her name’s Vicki –
and she’s a doll. Great in bed too!”
“But what about us?” I asked nervously.
“Up to you,” she said. “If you’re gonna be all jealous because I need a girl
now and then? We may as well split up. What do you think?”
“I wouldn’t be jealous.” I panted desperately, then honesty cut in. “Well,
maybe I would. But I’m crazy about you Cindy. I’d like to stay on being your
guy. Can I?”
“Sure. If you want,” she said – almost as if she didn’t care. “Though to tell
you the truth? You’re not much in the guy department either.”
I took a deep, relieved, breath. Sure, she hadn’t been overly complimentary,
but she hadn’t sent me away either. “Guess I don’t have to wear these aprons
any more,” I said.
“Huh? What’re you talking about?” she said, astounded. “You may not have to be
my girl any more, but I’ve got too used to you helping out around here – and if
you’re going to do sissy things, you may as well wear sissy aprons.”
“Aw Come ON Cindy! Please don’t call me a sissy,” I complained weakly.
“Did I call you a sissy?” she asked indignantly. “Did I?”
“Well maybe not in so many words,” I argued weakly.
“Then stop your bitching! Go and finish your dishes, then mix me a drink.
Okay?” She said this quite harshly.
I knew she was upset with me so made her drink before I did my dishes then had
an idea. The apron I was wearing had got creased and had a few splashes on it.
I changed it for my prettiest, full, one. Then took her drink in on a tray.
“Cindy? I’m sorry if I sounded like I was complaining,” I said meekly.
Her eyes took in my changed appearance and she rewarded me with a slight smile.
She took the drink and nodded. “Maybe you should start learning to curtsey?”
She said this seriously enough, but smiled when she saw me blush. “Just
teasing.” She said.
But another week or two went by – with her being increasingly contemptuous of my
abilities in bed, when she finally broke my heart. She knocked on my apartment
door late one afternoon.
“Hi Michael, can I come in?” she asked when I opened the door.
“Yes Cindy. Of course! Come in! What’s the matter?” I said as she passed me.
“Thought I’d best tell you face to face. Sorry Michael, we’re through. I’ve
got a guy now – a real man – a real stud. Sorry.”
I felt the blood rush from my face. “Oh Cindy! You don’t mean it! You know I
love you! I can’t give you up!”
She shrugged. “Michael? That’s just the way things are. You were fun for a
while, but you know that I’ve lost all respect for you as a man – and you
certainly weren’t much good as a woman.” As she talked, her yes took in my
apartment. “Though I’ll admit this Michael,” she said. “You sure do take great
care of your place. A great little housekeeper.”
“But this guy? Maybe he’s just a passing fancy? Maybe you’ll drop him pretty
soon. Couldn’t you just keep me on Cindy – please?” I babbled.
“As what? My housekeeper?” she laughed.
“Why not? Just for a while? Until you were sure that you love him?”
“LOVE? Who said anything about that?” she sniggered. “It’s great to get humped
by a real man – not a little sissy pansy like you!”
I couldn’t help it. “Oh Cindy! That’s mean!” I squeaked, almost in tears.
To my surprise, she was beside me now, and taking me into her arms. “Yes, I was
mean – and I’m sorry,” she said. “But if you want to keep on seeing me? You’ll
have to come and do my housework – all of it.”
“Honest?” I asked.
“Well? You can’t act the man around me. Nor the woman. Only thing left is for
you to do my housecleaning – and you know what I think of men that do housework
in pretty little aprons?” She smiled at the expression on my face. “That’s
right. You can be my little sissy Michelle. How’s that?”
“But I’m not a sissy,” I wailed.
“Don’t care. But if you’re going to do this? I’ll expect you to walk like a
sissy, talk like a sissy – and dress like a sissy until I break up with Doug.
Maybe by then? You’ll have remembered how to act like a man again, and I’ll
take you back.”
“You’ll take me back?”
“Maybe. No promises.”
“Oh Cindy! This is too much! I can’t!”
She got an aggravated look on her face. You know? You’r getting to be a royal
pain in the ass! You’re not a man – you’re not a woman – and now the way
you’re acting? You can’t even act like a proper sissy! What do you want me to
DO Michelle? Beat you? Threaten to spank you? Or do you still feel that your
that much of a male that you can fight me?”
With that, she took a step forward, and before I knew it sent, a hard punch into
my upper arm! I didn’t even have time to start crying when she gave the other
arm identical shrift! Both arms now paralyzed, I started to cry.
“Gonna come and be my little sissy maid Michelle?” she growled in a very
frustrated tone.
My arms hurt terribly and I had another awful intimation of how much I was
turning into a woman – what kind of makeup could I use to cover up my bruises
was of paramount importance for a second. But I was still convinced she
wouldn’t split up with me, so I pouted and shook my head stubbornly.
She looked like she was going to punch me again, and I cowered away. Then she
just shrugged. “Okay Michael. It was nice knowing you. Keep in touch, but
don’t be a pest about it. Okay?” And she started walking towards the door.
“Please! Can I at least think about your offer?” I begged, shaken that my
opinion had been disproven so quickly. She obviously wasn’t fooling around.
She stopped and looked back. “Not gonna screw around with this. Arguing with
little pansies is NOT my thing! You have a one time shot. Be at my door on
Friday night at seven sharp. Be prepared to spend the weekend. I’ll have Vicki
there, so you’d better behave. You can spend the weekend cleaning house and
learning how I want my sissy to behave. Don’t even think of knocking on my door
five minutes after seven, it won’t be opened for you. Understood?”
I nodded and a grin suddenly crossed her face. She came back and kissed me.
Took me into her arms and as I laid there, soft, weepy eyed, and submissive, she
grinned down at me. “Know something? I think you’re going think about it – then
you’ll come to my place on Friday – and be such a great little sissy! I don’t
think I’ll ever have to complain about you again! Goodnight sissy Michelle!”
She left me distraught and near weeping. As a mater of fact, I did shed some
tears – but they were more of anger than anything else. Who did that big broad
think she was? Who – or what – did she think she was dealing with? I raged for
all of my waking hours for the next day and a half. Then I started to try and
reason things out. Okay. This guy she was seeing. Suppose he was just a flash
in the pan? If I’d been supportive in this infatuation of hers? Maybe she’d
see that I was the right guy for her. Surely? Take me back in a flash?
Sure, the thought of being regarded as a sissy wasn’t appealing. But if I
actually hated it – which was highly likely? I could always quit – and who
would know the part I’d played? Surely, I could manage a few weeks of
indignity? I really loved Cindy after all – and what was a few weeks of shame
where love was involved? I started experimenting with makeup to cover up the
bruises on my arms. Okay, I still was undecided and did this just in case – but
I didn’t want Cindy to be reminded of how mean she’d been to me – or her friend
Vicki to see it either.
I knocked on the door at exactly seven o’clock on Friday night. A very pretty
brunette answered it. I knew that this must be Vicki – Cindy’s new girlfriend.
I felt a pang of jealousy, but smiled at her. “Yes?” she said, smiling
prettily.
“Hi. I’m Michael,” I said.
She cocked her head to one side and regarded me quizzically. “Who?”
“Michael. I’m a friend of Cindy’s.”
She shook her head. “Don’t think she’s expecting anybody called Michael
tonight.”
The curious inflection she put on my name gave me the hint. I blushed furiously
– which seemed to amuse her a little. “Maybe she mentioned me as Michelle?” I
asked.
“That’s something like it. Should I go check with her?” she asked innocently.
My mouth dry, I tried again. “Maybe she mentioned sissy-Michelle?” I said.
“Ah! I think that’s it! Hi sissy Michelle – or would you prefer to be just
plain Michelle when Cindy’s not around? I’m Vicki. ” As she said this, she
came forward and gave me a cheek to cheek kiss.
“Hi Vicky. Is Cindy around?” I asked.
“Well? She is – and she isn’t. Why don’t you come in and get dressed? She’ll
probably be more than willing to see you then?”
“I have to get dressed?”
“She expects her sissy to at least dress like one. Want to come with me?” With
that, she laid a dainty, beautifully manicured hand on my arm. “Come on. It
might not be as bad as you think,” she said consolingly.
But it was worse than I’d have ever dreamed possible! It took almost two hours
to get me ready to be presented to Big Cindy. She nodded approvingly when she
saw me. “Hi sweetie! Don’t you look cute! Come over here and give Big Cindy a
nice sissy kiss!”
One hand on my (padded) hip, the other drooping from my wrist, I minced over
towards her. “Hi, Big Cindy!” I lisped through scarlet, wet looking lips – and
batted my false eyelashes at her.
“These hot pink pedal pushers look lovely on you dear.” She said. “Just LOVE
those ribbons that tie at the calves. What material are the pants Michelle?”
“Thank you Big Cindy. The pants are satin.”
“I notice they zip up the back. Did Vicki do that for you?”
“Yes Big Cindy.”
“Do all the little fasteners too?”
“Yes ma’am.”
“Wasn’t that nice of her? I hope you said thank-you nicely.”
“Oh she was as sweet as could be!” Vicki laughed. “A regular little lamb.”
“I think you’ve forgotten dear? But Michelle is a Man – not a woman – though
it’s an easy mistake to make, isn’t it?” Cindy laughed and Vicki nodded in
agreement.
Then Cindy turned her attention back to me. “Is the blouse satin too?”
“Yes ma’am.”
“But isn’t that shade of blue kinda masculine for a sissy to be wearing? Though
I must say that those full sleeves look lovely on you. And are you wearing a bra
under it? Sure looks like it’s holding up a pair of somethings too. Is that
right?”
“Why don’t you tell Cindy about your pretty undies?” Vicki urged.
I gulped. Then quoted Vicki word for word “Darling pink satin with lace trim
to die for! Uplift bra, garter belt and nylons - Vicki told me you can’t abide
panty hose! (Giggled girlishly here). Oh – nearly forgot! A camisole –
matching of course. Would you like to have a little look?”
“Yeah. Open up your blouse. Let me see your sissy tits.”
“You didn’t answer Cindy’s question about the color of your blouse, sissy
Michelle!” Vicki chided me, but nicely, as I fumbled with the buttons of my
blouse, unused as I was to the long, scarlet false nails I now wore.
“No, Big Cindy.” I said, still working at the blouse buttons. “A sissy isn’t a
man, and isn’t a girl – just somewhere in between – so it’s okay to mix pink and
blue.” I looked anxiously at Vicki. “Did I say that right?” I asked.
“Like a good little sissy should. Just perfect!” she said and clapped her
hands. I blushed at the praise.
“Come over here sissy – let me see better!” Cindy commanded as I finally got my
blouse opened.
Humiliated, I minced over to stand directly in front of her. “Bend over!” she
said. Then as I did so, she winked at Vicki. “Kinda hard to imagine that little
sissy here was my boyfriend not that long ago?” With that, she cupped a lace
cup of my bra and lifted it gently. “I think his tits are bigger than yours
Vicki!” she laughed. “I like the way they move.”
“Well? I’ve always felt that you consider my breasts on the small side – so I
wanted to make you happy – but not TOO happy. It’s ME that’s your girl!” Vicki
retorted. Then added. “Come over here sissy! Don’t want Cindy getting too
excited – do we? I’ll help you fasten your blouse.”
So, back to Vicki I flounced back to Vicki, very conscious of my breasts bobbing
up and down inside the lace cups of the bra. Stood obediently in front of her
as she deftly fastened my blouse buttons again.
“But that lacy little apron with all the frills and ruffles. You expect to do
much work in it sissy?” Cindy asked as Vicki finished.
“Oh no, mistress!” I said, and, remembering Vicki’s advice and training,
curtsied prettily. “Mistress Vicki just thought I should look pretty for you in
my debut.” I added.
She laughed.
I thought that weekend the ultimate in humiliation. Little did I know what
fate, Big Cindy, Vicki – and Nona - had in store!
By late Sunday evening I had been almost converted to the mincing parody of a
walk that was desired of me. I lisped, I primped, and I flounced like any drag
queen. Learned how to insert and remove a butt plug – something necessary to
keep me walking correctly. Learned how to make sure that my makeup was kept at a
whorish level at all times. Learned to talk softly and effeminately – with a
pretty, seductive, lisp. Learned how to strut in high heels. Learned how to
roll my hair at night – and how to put on my OWN makeup.
Somehow, I wasn’t surprised when the clothes I’d worn to get there weren’t
returned. Was surprised though, when I was given a suitcase full of girly
clothes to take home with me. “You’re Cindy’s sissy now,” Vicki said.
I nodded, but Cindy, who’d been watching, showed no sign of having understood
me. Then she explained. “That means that you’re my sissy – PERIOD! All the
time! No days off! Understand?”
I swallowed hard – and nodded again.
I appreciated Vicki escorting me to the parking lot and driving me home. Wasn’t
too keen on giving up my car to her, but acquiesced when she told me she’d pick
me up ‘for work’ on Tuesday morning. Seemed I was to be allowed a day ‘off’ –
usually Mondays – but would be decided by Cindy on a week to week basis.
“In other words, I can’t make any plans?” I asked Vicki.
She patted my thigh. “Michelle? Sissies do what they’re told. They don’t make
plans. Why don’t you just settle down and accept your position with Cindy now.
You’re going to be her personal sissy – and, from what I can see? You’re going
to love it. You’re picking things up so fast, it’s incredible!”
“You really mean that?” I asked shyly, absurdly pleased that she saw me as
being good at anything.
“Why, of course!” she said. “You’re a natural! But let’s get you up to your
apartment, shall we?”
I was starting to like Vicki very much. Not only was she pretty, she was kind
to me. Okay, she’d had to talk firmly to me a few times over the weekend, but
she’d never spanked me for anything, although Cindy had told me that I’d better
hustle over Vicki’s knees any time I was told. “Vicki? Can I ask a question
before we go in?”
She cut off the car engine. “Yes sugar. But you’re not just trying to delay
going into your apartment building as a sissy for the first time, are you?”
“I’m scared of that,” I admitted. “But it’s these clothes in the suitcase.
What am I supposed to do with them? You’ve told me that sissies aren’t
supposed to do anything that involves lifting – we’re so weak. But I forgot and
tied to lift it . .”
“Hope Cindy didn’t see you!” Vicki admonished me.
I paled under my makeup. “No. And I’m sorry for disobeying you Miss Vicki. I
just forgot.”
“That’s all right Michelle. But from now on? You’d better remember that you’re
a full time sissy.”
“I’ll try,” I said contritely. “But like I was saying, the suitcase feels like
it’s got a lot of clothes in it. What am I supposed to do with them?”
She drew back from me in some surprise. “What do you think, Michelle? Wear
them!”
“All the time? I can’t see why!” I squeaked.
She shook her head. “Suppose Cindy or I call you and want you to come over to
our apartment and you’re not dressed properly? Going to tell us that you have
to get ready? Keep us waiting? Michelle, I’d suggest that you go nowhere
without your butt plug in place and your makeup on. You’re Cindy’s sissy now –
full time!”
It was not the answer I wanted, but I can’t say it was unexpected. I sighed.
“Pop the trunk, will you Vicki. I’ll get the suitcase.”
She shook her head. “Don’t know what I’m going to do with you. Silly sissy!
You just concentrate on walking properly while I carry the suitcase. When we
get inside, just ask the doorman to bring it upstairs to your apartment. But to
be sure? Just check in your handbag. Sure you got you keys?”
“They’re there Vicki,” I said after checking.
“Good girl! Let’s go!” she said.
I took a deep breath as we entered the apartment foyer. I’d never been
particularly friendly with the doorman or security people, but they all knew me.
The one who stood by the door didn’t recognize me as I sashayed towards him,
wrist drooping, hips swinging, my high heels click clacking on the parquet
flooring.
“Yes ladies? Anything I can do for you?” he asked, giving me the fisheye.
“I’m not a lady. I’m a sissy. Name’s Michelle Dean and I live on the seventh
floor. Could you carry my suitcase up there for me?”
Vicki was looking at me approvingly as I went into my prepared speech, speaking
and acting as campily as I could. He shook his head. “Can’t do it right now –
miss. But I’ll have it up there before You know it.”
“Thank you,” I lisped. Then in time honored girlie fashion, said goodnight to
Vicki, the doorman watching incredulously as I minced to the elevator.
I made it to my apartment without any difficulty. A while later, a knock on my
door let me know my suitcase had been delivered. I let it sit a while before I
got it. Noticed with some alarm that the suitcase that Vicki had carried with
no problem seemed awfully heavy now. Maybe I really was turning into a weak
little sissy? I shook my head in denial.
Okay. I was silly. Washed my makeup off and took my butt plug out. Went to
bed in my old pajamas and, when I woke up in the morning, threw on my plaid
robe. Was sitting in the kitchen drinking a cup of coffee – when Cindy
appeared! Furious!
“Wh- wh-wh? How’d you get in?” I stammered.
“Never mind!” she snarled – and had a firm hold on my ear. Hauled me, weeping
and wailing into the living room where she put me over her knees and literally
blistered my ass. Then, she carried me to my bedroom where she dumped me into
my bed. “Stay there until I let you know it’s safe to get up!” she hissed at me
then left. I heard her on the phone for a little while, but didn’t hear her
going out.
My backside was burning with pain and my eyes were raw with weeping. I’d had a
good night’s sleep but must have drifted off. I woke with a beautiful girl’s
face peering down at me. She showed perfectly white teeth in a smile. “Hi!” she
said. “I’m Nona. I’m one of Cindy’s buddies. We work out often. I’m going to
be staying with you for a while.”
“Okay,” I said sleepily. “Hi Nona.”
“Why don’t you get up, and then you can make me breakfast after you get
dressed?” she suggested silkily.
I felt my eyes widen and mouth fall open as she stood up – and up – and up! She
was huge! In great shape, mind you – probably not an ounce of fat anywhere.
Cindy is tall – about six-three but Nona dwarfed her by at least a few inches.
“You’re not going to hurt me, are you?” I asked fearfully.
“No sweetie. Cindy’s the one that doesn’t mind hurting little sissies that
don’t behave. I just like to humiliate them. So why don’t you get up and get
dressed Michelle? I’m kinda hungry.”
She meant what she said. Wouldn’t leave my room, just watched me while I got
myself ready for the day. She did ask me to take off “those silly clothes” and
I wasn’t about to refuse. So, nude, I had to look out undies and an outfit from
the suitcase. She nodded approvingly as I lubricated myself and slid the butt
plug into position, the slid into jet black satin undies, topped off with a
tight black satin skirt and scarlet silk blouse. Fishnet stockings and black
high heels completed the clothes. While chunky matching bracelets, necklace and
clip on earrings helped to accessorize the outfit after I’d made myself up and
brushed my hair.
When I finished, she drawled. “Any joy juice in there honeybunch?”
“Eh? I don’t understand?”
“You will. Go back and lie on top of your bed. Go on.”
I swished over to the bed and lay down on my back.
“Now pull your skirt up – and your panties down Michelle.”
I could taste my waxy lips as I wetted them with my tongue. “What are you doing
Nona?” I asked nervously as she came and knelt on the floor beside the bed. “Now
don’t move!” she warned me. “Not an eyelash!”
She was now putting her mouth over my erection – and sucking! I started to
undulate at the eroticism of what she was doing to me and she stopped and gazed
down on me with enigmatic eyes. “Behave, sissy! Be still!”
And now, the epitome of a feminized, submissive, male I lay there passively as
she sucked me into ejaculation. “Ah! Nice and fresh!” she said and wiped her
mouth with the back of her hand.
Nona took over my life completely – except when she took me to Cindy’s. She had
been perfectly truthful when she said that her enjoyment was centered around
humiliation. Under her constant scrutiny, I was Introduced to levels of
humiliation I would have never dreamed possible.
She was an extraordinary seamstress. Moved her own sewing machine into my
apartment and took over my bedroom. Had me hire an interior decorator and a
firm of painters to re-decorate a bedroom for me. They were all women and
treated me with a level of amused contempt as I swished and sashayed around the
apartment in some of the most ludicrous outfits imaginable. I think that Nona
got a real kick out of seeing some of the more mannish ladies making me squeal
by pinching my backside, or patting me in the most suggestive way as I blushed
and simpered.
Nona also took me outside at times when I wasn’t cleaning at Cindy’s. Loved to
take me for a walk in the park – literally put me on a leash and would talk to
other pet owners – often commanding me to “stay” while she chatted. She’d make
me put on my most garish clothes, my highest heels – and layer my face in gaudy
makeup. Drench me in perfume. Obediently, I’d ‘heel’ on her command and mince
along, my two arms bent at the elbow, sticking straight out in front of me, with
my hands drooping. – and lord help me if I wasn’t smiling happily, or chattering
girlishly the whole time.
She made me ‘working’ outfits too, which usually had Cindy roaring with
laughter. Abbreviated maid uniforms – more suitable for stage or porno films.
Stark white nurse’s uniforms of similar style. Ballerina in a tutu. Cheer
leader – where I was taught to do simple dance routines with the pom-poms.
Harem girl in bloused chiffon trousers and beaded satin jacket.
Nona would often disappear while I was at Cindy’s. Took care of her own
business, went and worked out. I think she was starting to look upon me as her
own personal property and didn’t enjoy seeing somebody else boss me around.
Either that, or she wasn’t interested in seeing Cindy and Vicki playing around
with each other. And? Playing out was something they’d often do around me. It
was pure shame for me when I’d be dressed in one of my skimpy maid outfits and
have to serve both ladies while they’d be lying in bed – or on a couch – and
slowly making out.
And then came the day of my total humiliation. Cindy had bought me a proper
maid’s uniform. Oh, it was pretty. Decidedly feminine. I had been quite
surprised when I got to the apartment and Cindy looked at me. “Go and take that
muck off your face.” She pointed to her bed where the uniform lay along with
some respectable lingerie. “Also? Take that butt plug out of your ass. See if
you can walk properly – like a maid instead of some swish drag queen. Think you
can do that? And when you put your makeup on? Try and look human, would you?”
I did have a problem walking like a proper woman but practiced as much as I
could in the bedroom before presenting myself for approval. I was SO happy.
Was this, possibly, my initial release from sissyhood? Maybe she was realizing
that I was a human being again?
When I did report to her, she smiled. “You’ve turned into quite a pretty girl
Michelle. Think you’d rather be a girl than a sissy?”
I curtsied as daintily as I could. “Oh yes! Miss Cindy. Oh yes!”
“Well let’s see how you do this afternoon. Doug’s coming over for an afternoon
session. He’s still all man. Only thing? He really hates pansies and fairies.
If he finds out that you’re a sissy? I wouldn’t like to be you, is all. So?
Think he’ll find out?”
I looked at her, horrified. “You want me to be your maid – while your boyfriend
is here?”
Cindy smirked. “Yes Michelle. Thought it might teach you something about what
girls see in real men.” The doorbell rang. “That’ll be him now, I expect. Go
and answer the door.”
Terrified, I hurried to the door and opened it.
Doug wasn’t as big as I’d imagined. Probably not even as big as Cindy –
although he was whipcord lean and moved athletically. Had a pleasant enough
face as he smiled at me, surprised to see a maid I think. “Hi,” he said. “I’m
Doug. A friend of Cindy’s.”
“I think she’s expecting you sir,” I said softly as I curtsied, burning with
shame inside at what Cindy was making me do, gradually realizing that any
chances I had of ever reverting to masculinity in her eyes was becoming
increasingly remote.
I think that Doug was originally embarrassed when she called me into her bedroom
by the use of the tinkling maid’s bell. They were lying, half naked on the bed
and she moved in such a way that I saw his member. It was huge, and I felt
diminished because of my own small sexual organ. “Michelle? She drawled. “Be a
darling and bring over the package of condoms from the top drawer over there,
would you?”
Face on fire, I did as I was told. As I took the package of condoms towards
them, she smiled. “Well? Take one out for the man, would you sweetie?”
Fingers trembling I picked out one and held it towards him. I think he was
embarrassed too, but managed a small “Thanks”
“Would you like Michelle to put it on for you Doug? She’s got lovely soft hands
– and I’m sure she’d be thrilled!” Cindy purred, smiling as the horrified look
crossed my face.
“No. But thanks for the offer,” he said, taking the condom from my hands.
“Thanks Michelle.”
“You’re welcome sir.” I said this gratefully – and honestly as I curtsied
again.
“Put the rest over on the bedside table Michelle. We’ll probably need them
later. Right lover?” she said, turning suddenly lustful eyes up to him.
“Sure hope so!” he laughed. “Now, if you don’t mind. Would you ask Michelle to
leave? I don’t like performing in front of an audience.
“Aw! She’ll be SO disappointed.” She shot a look at me and made a shooing
gesture with her hands? Well girl? You heard the man! Scoot!” She said it
with such disdain that I started to cry. “See Doug?” she laughed. “Told you
she’d be disappointed!”
There wasn’t much more to that day. They were still in bed when Nona came to
take me home. I even didn’t mind it so much when she sucked me off when we got
there. As it was about the only way I got any kind of sexual relief any more I’d
learned to just lie down when told to do so – and stay still. It was
humiliating of course, but as the rest of my life was too, I didn’t see much
percentage in fighting it. As always, it left me exhausted.
Vicki wasn’t allowed to be in Cindy’s apartment when Doug called – so she’d come
over and visit with me – Doug would not have been pleased to know that Cindy had
a girl friend and seemingly didn’t want me there either. This allowed Nona to
take time off from supervising me, so she’d take off as often as not. Vicki
treated me nicely. Okay, she was my boss – no question about it. But one
afternoon, she brought me some of her own clothes to wear – and took me out
shopping. Even let me take out my butt plug and tone down my makeup. “I’d rather
be with someone who looks like a girl than a flaming drag queen. You don’t
mind, do you Michelle?”
Mind? I adored her for it! Told her so – and she gave me such a nice kiss!
“You really want to be a girl, Michelle?” she asked.
“Yes,” I replied shyly. “It’s much better than being a sissy.” Naturally, I
meant that I much preferred the more conservative dress and makeup – and acting
less flamboyantly. But maybe I should have thought more before answering in
that fashion.
And, over the period of a month or so, I gradually was allowed to tone
everything down. Nona still liked to humiliate me in many ways, but I was
allowed to become more and more feminine – as versus being a garish sissy.
Then, one day, Cindy spoke to me. “Vicki tells me that you want to be a girl?”
“Yes, well, kinda,” I answered.
“Good! I’ve scheduled an appointment with a plastic surgeon for you,” she said.
“Huh? What for?”
“Well? I’ve sort of grown to like you working here as a maid, so think I’ll
take you on full time – so don’t want you embarrassing me by prancing about like
a sissy all the time. Let you look a little more human.”
I was excited but confused. “But I don’t understand. What’s the plastic surgeon
for?”
“Breast implants, hip enhancement – plump up those lips of yours.”
“Ha ha! I don’t need that sort of thing. Please don’t Cindy?” I quailed.
“Well – it’s as much for Vicki’s sake as mine,” she said. “She’d like you to be
her girl friend. She’s never used a dildo before, but she’s really interested.
Says she’s becoming really fond of you.”
I stared at her unbelieving. “But Vicki’s SO feminine!”
Cindy shrugged. “She’s probably more masculine than you. Wouldn’t you agree –
you swishy little excuse for a man?”
I pouted. “No. Don’t agree!”
She shrugged. “Okay. Tell you what. Tomorrow when you come over here? I want
you in a nice, girlish dress and made up pretty. When we get to Vicki’s, I’ll
tell her that if she wants you, she’s gonna have to take you, because you’re not
willing to volunteer to be her girl. If she can’t talk you into it? I’ll cancel
the appointment. How’s that?”
“But can I come and stay here as your maid – and stop wearing all those ugly
clothes – and stop using the butt plug?”
“Sure.”
“Promise?”
“You got it sweetie – but you have to make yourself as pretty as possible
tomorrow. Deal?”
“Okay,” I said.
I took a lot of care the following morning. Probably overdid it a little. A
soft, summery, floral, sundress with a matching jacket and short white cotton
gloves. A scarf to match, tied into my hair, and white sandals. Matching purse
of course. I muted my makeup – although I did use a stronger pink on my
lipstick than would be considered ladylike – it was one of my favorite shades.
I wasn’t a hundred percent sure that I was that much stronger than Vicki – but
I’d manicured her fingers for her a number of times and knew that her hands were
just as soft and plump as mine. Her arms just as weak. Where did she and Cindy
come off thinking that I would ever consider being a girl for her?
“Aw Michelle! How pretty you look. Why don’t you lie down for Nona?” Nona said
when I took her breakfast to her..
“But Nona darling? I’ll have to do some work for Cindy – and you know how much
you tire me out.”
“Sorry dear. Can’t resist you when you look so pretty – so lie down!” she said.
Almost weeping, I did what she said. Then, to make matters worse? She couldn’t
resist it, she said – and did it to me again, just before we left for Cindy’s.
I actually fell asleep in the car as she drove us there, I was so tired.
Vicki opened the door for us. She looked lovely in a pretty silk dress and, as
always, was made up beautifully. More man than me? I thought to myself and hid
my grin – although I was SO sleepy.
“You look lovely today, Michelle,” she said coming forward to kiss me.
“So do you, Vicki,” I said preparing to brush cheeks.
But she surprised me. “Think I’m gonna eat you all up!” she said, grinning,
took my face in her hands – and kissed me firmly on the lips! Then she gently
tugged me into the apartment. “Nona and Michelle are here Cindy!” she called
out.
“Let’s see them!” Cindy shouted back.
Cindy made me do a twirl in front of her and indicated how pleased she was with
my appearance. Nona sat down on the couch. “Well? When does this big battle
take place Cindy?” she asked.
Cindy shrugged. “Whenever Vicki wants I guess.”
Vicki still had a hold of my arm. “Why don’t we sit over here Michelle – and
you can explain why you don’t want to be my girlfriend.” And, somehow, she was
pulling me over to sit on a sofa in front of the two grinning women.
“But I’m not a girl Vicki,” I said.
“But didn’t you say that you wanted to be one - a number of times!” she
answered. “And you look like a very pretty girl! Now give me a kiss!”
Our dresses rustling, our perfumes mingling, our lipsticked lips met once again
– and suddenly her hand was up under my dress, softly touching my erection.
“Kinda small, isn’t it Michelle?”
“Well, maybe.” I admitted.
Then her hand took one of mine and was pulling it up under her dress! And she
had a dildo on!
“Mine isn’t as little as yours, is it?” she whispered.
“But it isn’t real!” I protested.
“Real enough!” she laughed. “Want to see?” With that, she pulled her dress
and slip hems up to show the big thing bulging under her panties. “Why don’t
you give it a little kiss!” she suggested, now taking a hold of my scarf and
pulling my face down towards her.
I tried to resist – but she was too strong and weakened by Nona earlier on, my
lips were soon touching the tip of the dildo. Cindy and Nona both chuckled and
applauded.
“That’s a good girl! Now that wasn’t so hard, was it?” Vicki crowed, letting
me get up before twisting me into her embrace again. “Why don’t you ask me to
make love to you?” she asked.
“NO Vicki! Please! I can’t” I wept as she started turning me over onto my face
and lifting up my dress and slip to bare my panties.
“Such a weak, pretty little thing. Aren’t you?” she laughed, pulling my
panties down. “I’m just not sure. What do you want – a C cup or a D?”
28 March 2011
27 March 2011
The New Secretary
By: Anonymous
I had been looking for work in the want ads and noticed there
weren't many choices. Most of the jobs were menial labor or fast
food types and didn't pay much. But I did find a job opening
listed at a local law office. I circled the ad then drove down
to apply.
I entered the small out of the way building and noticed a stack
of papers and books on a couple desks in the main office. After
asking if anyone was in I heard a ladies voice. She told me to
come into her office. I entered to see her moving about the
paperwork while she talked on the phone. After she motioned for
me to take a seat I waited until she was done with her call.
"Can I help you?" She said with a smile. I showed her the ad she
had placed in the paper for a legal secretary. She took her seat
and looked me over as I handed her my resume.
"I do need a secretary very badly as you can probably tell from
the mess of papers and books in here" she said. "I know these
days that there are a lot of male secretaries out there and you
seem well qualified" she continued "but I am more in the market
for a woman secretary, it's more traditional, you understand."
I told her that I had a degree and would rather use my brain
than have to twirl either a spatula or a shovel. She seemed to
understand as I continued about really needing a job and after
I nearly begged for the chance she finally relented.
"You don't mind doing what is usually women's work then?"
I told her I didn't mind. With that she hired me and had me
report bright and early the next day.
It didn't take long to get the place in shape and within a
couple weeks I pretty much learned all I needed to know. I
worked at my desk answering the phone and typing reports in the
outer office and Donna worked in her private office. She was a
good lawyer, was in her early 50's or so and had a bit of a
buxom build. She was larger than I was and with me being
slightly built and short as well she was also a couple inches
taller. She often teased me that I should maybe wear high heels
around the office so I could be taller than her! I then thought
it a bit strange as I noticed that her clothing seemed just the
slightest bit masculine in appearance.
I passed the comment off until a couple weeks later. I had been
working there for a month and everything was rolling right along
when one Friday afternoon Donna called me into her office. It
had been a bit slow that week and it was nice to not have to
hustle quite so much and I thought that after the work got down
to a routine it would be a pretty good job, especially since I
was making about ten bucks an hour more than most any place else
in town. I went into Donna's office and after closing the door
behind me took a seat and awaited what she had to say.
I figured it might be some extra work, or maybe her thanking me
for getting everything caught up or maybe even her telling me I
could leave early for the weekend but that isn't what happened.
She rummaged through her desk drawer then brought over a small,
paper bag package and handed it to me. I opened the package and
reached in to feel something slippery and silky then pulled the
material out and noticed I was now holding a pair of ladies
panties! They were full cut, white nylon briefs and very
feminine all done up with lace and bows!
"What's this!?" I questioned with a funny look on my face.
"Just a little something for you Dennis" she said with a smile.
"I'd like you to start wearing them under your suit when you
report for work. And don't worry, I will pick up enough of these
pretty, feminine panties to keep you properly dressed from
Monday through Friday. You don't have to pay me for them,
consider them a bonus." She said as she returned to her desk and
took her seat.
I folded the panties and put them back in the bag. "I don't
think so Ms. Roberts."
She didn't like my apparent stubbornness.
"What did you say?" She said.
I repeated that I wasn't about to wear women's panties but she
only giggled slightly as she continued.
"I told you this was traditionally women's work didn't I?" She
said.
I said that I remembered that but continued on thinking she was
joking. I got out of my chair saying I had work to finish before
five o'clock but she replied by saying "you're not dismissed
yet! Pick up that package," she said with a demanding tone.
"Monday morning you will come to work and I will check to make
sure you are properly dressed."
I told her I wouldn't do it! She then ended the argument.
"You'll report to work on Monday wearing these panties under
your suit or you'll look for another job!" She said with
authority.
She relaxed a bit by telling me it really wasn't that big a deal
and that I would get used to it.
"I just like knowing my little secretary is dressed just a
little feminine underneath. And what's the worry? Who's going to
know?" She finished, then said I could return to my work.
I didn't know what to think! If I didn't do what she said I
would be out of a job and in a real jam! I quietly gathered up
the package then left her office closing the door behind myself
as I left.
I dreaded the following Monday morning. I got up, showered and
got ready for work. I took my suit off the hanger and grabbed a
fresh shirt and tie then noticed the package Donna had given me
sitting on the dresser. With no way out at least for the moment
I took the package, reached into it then took out the panties
and began putting them on! I finished dressing as usual and then
drove to work.
I entered the office and had just started for the coffee machine
to make coffee when I heard Donna call me into her office. I
entered the office and as I closed the door she was already
moving towards me asking how my weekend was. She then moved in
close and reached for my pants! I startled back. "Just relax
now, I'm not going to bite!" She said as I stood there.
She reached over and holding my belt with one hand unzipped my
pants with the other. She then reached in and felt the front of
the panties I was indeed wearing. She felt the creamy smoothness
and could feel the lace trim at the front and the little bows at
the front of the lace trimmed legs.
"Feel good don't they?" She said with a wicked smile as she felt
me through the panties.
Just as she started to stroke my member I pulled back and she
withdrew her hand and returned to her desk. I could feel my face
redden with embarrassment as I quickly zipped back up then
mentioned that I had coffee to make.
The morning went as usual until after lunch. Donna got back
about a half hour late and after hanging up her coat she smiled
and put another package on my desk as she left for her office.
I could tell the package was from one of the local lingerie
stores. I couldn't believe she was serious but realized she was
as soon as I looked inside and saw another dozen or so pairs of
ladies panties! They were in several pastel shades and all the
full cut type and all had lace and were adorned with appliques
and other lacy trim and little bows. I quickly closed the
package and put it in one of the desk drawers realizing that I
would now be wearing panties to work every day! I was a bit
sickened to see that the days of the week were embroidered on
one set of the panties as well when I got them home and took
them out of the package!
The next morning I was back in Donna's office for inspection.
She had me take my pants down this time and then rubbed her
hands over the cool, slippery pink fabric.
"My, you seem to like the pink ones hummm?" She said with a
giggle as she looked me over then pulled them up tight on my
waist and squeezed and rubbed my bottom through the shiny nylon.
I asked how it could possibly matter which color I wore and she
giggled, satisfied I was still following her orders.
"But there's one thing though," she said as she looked me over.
"I'd like to have you start shaving," she said as she saw the
sparse but noticeable hair on my legs. I felt shocked!
"Shave?" I said with a gasp.
"Yes, you'll look so much better in these when you are properly
shaved," she added as I pulled my pants back up.
"How much to I have to shave?" I asked in quiet terror.
"Everything silly!" She said with a giggle. "Tomorrow morning I
will expect to see you nice and smooth all over without a hair
below your eyebrows except for your 'bikini cut' down below" she
giggled at allowing me to keep a little hair.
I pleaded with her to not make me do this but she was insistent!
It was either that or get ready to start looking for another job
with what most likely would be a menial labor one with a lot
less pay! I quietly returned to my desk and finished out the
day.
The next morning it was inspection time with Donna again in her
office. This time she made me strip down to my socks and panties
while she looked my now totally shaved body over! Later that day
she called me in to her office once again and this time handed
me several pairs of nude, support pantyhose! I knew what was
next. Now in addition to wearing panties to work I would now be
wearing women's hosiery to work too! And the next day it was
another inspection. Donna noticed my panties under the shiny
nylon pantyhose as she fondled my now shaved and nyloned legs!
"Mmmmmmm, don't they just feel delicious?" She said as she
marveled at how the nylons shined in the light and how they felt
under her hand as she rubbed the material against my legs! I
started having second thoughts about continuing working for
Donna and even though I needed the job I thought about just
quitting while the quitting was good.
But as I finished pulling up my pants and tucking in my shirt
once again Donna told me she was giving me a raise for my being
a good secretary and such a good sport. She then handed me
another package and told me how nice I would feel with a
pedicure! Then once back at my desk I noticed the nail polish
and other do-dads in the package!
The days went by and with the workload I found I actually forgot
about the panties and pantyhose from time to time, just like
Donna had said by saying "don't worry, you'll get used to them
in no time."
With another week came another feminine addition to my lingerie
wardrobe, and then another, and another! The following Monday I
was standing in Donna's office before starting work while she
looked me over once again. By now, she really had me decked out!
I was wearing my panties and pantyhose complete with my now red
nailed pedicure done up in a bright gloss red that showed
through the toes of the stockings. She had also added a tight
girdle briefer panty to my wardrobe and showed me how she wanted
me to "tuck" myself so I wouldn't show a bulge. Finally, she had
me wear a pair of white nylon pants liners and finished the look
with a matching, lace trimmed nylon camisole! I was now,
underneath, totally dressed!
I begged her to let me take off the camisole saying the straps
would show through my shirt but she wouldn't have any of it! She
said if I was worried I should start wearing T-shirts and / or
keep my suit coat on at all times. I thought the next step was
the last straw though because the following Monday, she brought
a pair of high heels to work that were in my size!
The shoes were black patent leather pumps and Donna made sure to
get a pair with open toes to show off my painted toe nails! I
was grateful that most of our work was corporate and didn't
involve a lot of walk in traffic but I drew the line at wearing
high heels and complained immediately!
"What are you doing to me Donna!?" I asked with a quizzical
glare as I stared at her. But she only smiled with her usual air
of authority knowing full well who was in control.
"I thought you said 'who'll know' and that nobody could tell I
was wearing ladies lingerie? If I wear these shoes around the
office what happens when somebody comes in!?" I said in a
terrified tone. "They'll freak out!"
"Don't worry!" She said. "You just get yourself a pair of
loafers and keep them under your desk. Then, if someone comes
into the office you can change shoes without them knowing."
"But what about these nylons?" I said pointing to my ankles.
"Your pants are long enough, just put your dress socks in the
drawer until you leave at night."
She had it all figured out and even though I tried to argue
further it did no good. Then she told me If I could learn to
master the heels in a week she would give me another raise!
It became very strange almost surreal. She watched as I went
back to my desk and took off my wingtips and black dress socks.
My nyloned feet complete with red nail polish were now clearly
evident! And worse now because I was stepping into women's high
heeled shoes! Donna smiled with satisfaction at seeing them on
me.
She had to help me stand at first and giggled as I wobbled on
the five inch stiletto heels as I moved around the office doing
nothing more than trying not to fall. She had me continue to
practice and coached me how to step until I started walking a
little better. She then returned to her office. An hour later I
heard her ask me to bring her in a fresh cup of coffee. I knew
what she wanted, she wanted to see me mincing on the heels and
did just that as I carefully made my way into her office with
the hot coffee. Donna thanked me then watched as I teetered, the
heels forcing my hips into a slight wiggle as I moved back to my
desk. And that's how it went.
As the days went by I would put on the high heels immediately
after arriving to work and leave them on until my lunch break.
After lunch however, it was back in the heels! The following
Thursday I was just finishing putting away some files in the
cabinet and walking back to my desk. It wasn't five minutes
later that a gentleman came into the office wanting to talk with
Donna! I managed to slip out of the heels and put my new slip on
loafers on and then escort the man in to see Donna! After he
left I had to put the heels back on but I was shaken from the
incident and complained to Donna about it.
She then said we were taking the next week off! I asked why and
she replied "if you are worried about wearing the high heels we
can do something about it so you won't look or feel so out of
place. And since you're getting so good in walking in them it'll
be easy." She said with another of her smiles and finished by
telling me that I would be spending the entire week at her home.
I had an inkling of what was going to happen but not to the
degree it happened! I threatened to quit and didn't really care
but Donna was insistent and with an even larger raise being
offered I felt almost stuck somehow. The job wasn't that hard,
even in the heels but I knew after I was told the rest of
Donna's plan that I could never pull it off.
The first thing I was to do was pack up and move out of my
apartment. I would be living with Donna now and after she was
finished with me there would be no way I could really go back to
my place anyway. Then the next week passed, and with the fifteen
hour days and all the work it passed slowly! But soon it was
Monday morning and the start of another work week.
I was terrified to get out of the car when we pulled up to the
office but Donna insisted that I could make a go of it and that
no one would even notice my changes. I was just the "new"
secretary. I was nervous as I opened the car door and felt the
click of my high heels as they hit the pavement. I took my purse
and after leaving the car I made my way up the sidewalk with
Donna. I could feel my new bust jiggling and feel the cool
morning air swirling around my nyloned legs! And could hear the
swish of my nylons brushing my calves and thighs with each step
as I minced along in my tight, satin lined skirt on those five
inch heels! I saw a few people moving about and driving past on
the street but nobody pointed, or laughed or yelled out. I did
notice a few women give me a passing glance as they went about
their business and a few men looking me over as we made our way
to the office door.
Once inside I was now the "new" secretary and would be known as
Deborah. I hung my car coat up, set my purse on my desk then
went about my regular duties by making coffee. Donna looked me
over.
"Yes, you're a proper little secretary now, very nice, very
ladylike." Then, issuing a satisfied smile she went into her
office.
In being off for a week there was a lot of mail and paperwork to
file and catch up on. I finished with the coffee then swished
into Donna's office to deliver her cup. She noticed me mincing
on the heels, my shiny nylons swishing under my tight pencil
skirt and my bust jiggling under my satin blouse as I set the
cup on her desk.
"Thank you Deborah dear" she said as she casually went back to
work.
"Yes ma'am" I replied as I returned to my duties.
I sat down at my typewriter and was glad that Donna didn't have
my salon nails made that long. This way they were short enough
so I could still type. And I had a lot of correspondence to
answer and a lot of typing to do. So I set to work. A couple
hours later Donna left for downtown on a couple errands and I
decided to stay through lunch to stay safe at the office on my
first day totally dressed as a woman, and to get the extra work
done.
I took phone calls, answered letters and did my filing as usual
then noticed myself in the mirror at the new look Donna had
helped to give me. I ran my hands over my feminized form and was
astounded! She had dressed me from head to toe and from the skin
out! She had gotten me a complete new wardrobe so I would be
able to look like the perfect little feminine lady every day
around the office. She had corseted my waist, and gotten me a
well padded girdle that really widened my hips and rounded my
bottom, and I could feel the weight and jiggle from the silicone
breast forms that now sat snugly in the cups of my satin
brassiere under my lacy, white nylon full slip and my blue, long
sleeved satin blouse with high collar and large satin sash bow
at the front.
My eyebrows had been plucked into a high and feminine arch now
and my ears had been pierced. I could feel the gold hoops as
they dangled against my neck from under my long hairdo that was
now dyed a bright blonde and fixed in a feminine style that
parted in the middle and feathered away from my face in large
sweeping curls. I was slightly built and small in stature to
begin with but looked nothing like a man anymore and any
masculine nuances I had were now hidden by Donna's intensive
week long training session and any left over manly traces were
now totally muted, covered up and totally concealed by the
ladies clothing, hairstyle, makeup, perfume and jewelry.
The days and weeks passed. And although we had little walk in
traffic, no one ever suspected that I was a man. They simply saw
the name plate "Deborah" and behind the desk a feminine, shapely
lady going about her secretarial duties as the scent of perfume
hung in the air and the sound of swishing nylon echoed through
the office whenever I moved in my seat or crossed my legs!
I had been looking for work in the want ads and noticed there
weren't many choices. Most of the jobs were menial labor or fast
food types and didn't pay much. But I did find a job opening
listed at a local law office. I circled the ad then drove down
to apply.
I entered the small out of the way building and noticed a stack
of papers and books on a couple desks in the main office. After
asking if anyone was in I heard a ladies voice. She told me to
come into her office. I entered to see her moving about the
paperwork while she talked on the phone. After she motioned for
me to take a seat I waited until she was done with her call.
"Can I help you?" She said with a smile. I showed her the ad she
had placed in the paper for a legal secretary. She took her seat
and looked me over as I handed her my resume.
"I do need a secretary very badly as you can probably tell from
the mess of papers and books in here" she said. "I know these
days that there are a lot of male secretaries out there and you
seem well qualified" she continued "but I am more in the market
for a woman secretary, it's more traditional, you understand."
I told her that I had a degree and would rather use my brain
than have to twirl either a spatula or a shovel. She seemed to
understand as I continued about really needing a job and after
I nearly begged for the chance she finally relented.
"You don't mind doing what is usually women's work then?"
I told her I didn't mind. With that she hired me and had me
report bright and early the next day.
It didn't take long to get the place in shape and within a
couple weeks I pretty much learned all I needed to know. I
worked at my desk answering the phone and typing reports in the
outer office and Donna worked in her private office. She was a
good lawyer, was in her early 50's or so and had a bit of a
buxom build. She was larger than I was and with me being
slightly built and short as well she was also a couple inches
taller. She often teased me that I should maybe wear high heels
around the office so I could be taller than her! I then thought
it a bit strange as I noticed that her clothing seemed just the
slightest bit masculine in appearance.
I passed the comment off until a couple weeks later. I had been
working there for a month and everything was rolling right along
when one Friday afternoon Donna called me into her office. It
had been a bit slow that week and it was nice to not have to
hustle quite so much and I thought that after the work got down
to a routine it would be a pretty good job, especially since I
was making about ten bucks an hour more than most any place else
in town. I went into Donna's office and after closing the door
behind me took a seat and awaited what she had to say.
I figured it might be some extra work, or maybe her thanking me
for getting everything caught up or maybe even her telling me I
could leave early for the weekend but that isn't what happened.
She rummaged through her desk drawer then brought over a small,
paper bag package and handed it to me. I opened the package and
reached in to feel something slippery and silky then pulled the
material out and noticed I was now holding a pair of ladies
panties! They were full cut, white nylon briefs and very
feminine all done up with lace and bows!
"What's this!?" I questioned with a funny look on my face.
"Just a little something for you Dennis" she said with a smile.
"I'd like you to start wearing them under your suit when you
report for work. And don't worry, I will pick up enough of these
pretty, feminine panties to keep you properly dressed from
Monday through Friday. You don't have to pay me for them,
consider them a bonus." She said as she returned to her desk and
took her seat.
I folded the panties and put them back in the bag. "I don't
think so Ms. Roberts."
She didn't like my apparent stubbornness.
"What did you say?" She said.
I repeated that I wasn't about to wear women's panties but she
only giggled slightly as she continued.
"I told you this was traditionally women's work didn't I?" She
said.
I said that I remembered that but continued on thinking she was
joking. I got out of my chair saying I had work to finish before
five o'clock but she replied by saying "you're not dismissed
yet! Pick up that package," she said with a demanding tone.
"Monday morning you will come to work and I will check to make
sure you are properly dressed."
I told her I wouldn't do it! She then ended the argument.
"You'll report to work on Monday wearing these panties under
your suit or you'll look for another job!" She said with
authority.
She relaxed a bit by telling me it really wasn't that big a deal
and that I would get used to it.
"I just like knowing my little secretary is dressed just a
little feminine underneath. And what's the worry? Who's going to
know?" She finished, then said I could return to my work.
I didn't know what to think! If I didn't do what she said I
would be out of a job and in a real jam! I quietly gathered up
the package then left her office closing the door behind myself
as I left.
I dreaded the following Monday morning. I got up, showered and
got ready for work. I took my suit off the hanger and grabbed a
fresh shirt and tie then noticed the package Donna had given me
sitting on the dresser. With no way out at least for the moment
I took the package, reached into it then took out the panties
and began putting them on! I finished dressing as usual and then
drove to work.
I entered the office and had just started for the coffee machine
to make coffee when I heard Donna call me into her office. I
entered the office and as I closed the door she was already
moving towards me asking how my weekend was. She then moved in
close and reached for my pants! I startled back. "Just relax
now, I'm not going to bite!" She said as I stood there.
She reached over and holding my belt with one hand unzipped my
pants with the other. She then reached in and felt the front of
the panties I was indeed wearing. She felt the creamy smoothness
and could feel the lace trim at the front and the little bows at
the front of the lace trimmed legs.
"Feel good don't they?" She said with a wicked smile as she felt
me through the panties.
Just as she started to stroke my member I pulled back and she
withdrew her hand and returned to her desk. I could feel my face
redden with embarrassment as I quickly zipped back up then
mentioned that I had coffee to make.
The morning went as usual until after lunch. Donna got back
about a half hour late and after hanging up her coat she smiled
and put another package on my desk as she left for her office.
I could tell the package was from one of the local lingerie
stores. I couldn't believe she was serious but realized she was
as soon as I looked inside and saw another dozen or so pairs of
ladies panties! They were in several pastel shades and all the
full cut type and all had lace and were adorned with appliques
and other lacy trim and little bows. I quickly closed the
package and put it in one of the desk drawers realizing that I
would now be wearing panties to work every day! I was a bit
sickened to see that the days of the week were embroidered on
one set of the panties as well when I got them home and took
them out of the package!
The next morning I was back in Donna's office for inspection.
She had me take my pants down this time and then rubbed her
hands over the cool, slippery pink fabric.
"My, you seem to like the pink ones hummm?" She said with a
giggle as she looked me over then pulled them up tight on my
waist and squeezed and rubbed my bottom through the shiny nylon.
I asked how it could possibly matter which color I wore and she
giggled, satisfied I was still following her orders.
"But there's one thing though," she said as she looked me over.
"I'd like to have you start shaving," she said as she saw the
sparse but noticeable hair on my legs. I felt shocked!
"Shave?" I said with a gasp.
"Yes, you'll look so much better in these when you are properly
shaved," she added as I pulled my pants back up.
"How much to I have to shave?" I asked in quiet terror.
"Everything silly!" She said with a giggle. "Tomorrow morning I
will expect to see you nice and smooth all over without a hair
below your eyebrows except for your 'bikini cut' down below" she
giggled at allowing me to keep a little hair.
I pleaded with her to not make me do this but she was insistent!
It was either that or get ready to start looking for another job
with what most likely would be a menial labor one with a lot
less pay! I quietly returned to my desk and finished out the
day.
The next morning it was inspection time with Donna again in her
office. This time she made me strip down to my socks and panties
while she looked my now totally shaved body over! Later that day
she called me in to her office once again and this time handed
me several pairs of nude, support pantyhose! I knew what was
next. Now in addition to wearing panties to work I would now be
wearing women's hosiery to work too! And the next day it was
another inspection. Donna noticed my panties under the shiny
nylon pantyhose as she fondled my now shaved and nyloned legs!
"Mmmmmmm, don't they just feel delicious?" She said as she
marveled at how the nylons shined in the light and how they felt
under her hand as she rubbed the material against my legs! I
started having second thoughts about continuing working for
Donna and even though I needed the job I thought about just
quitting while the quitting was good.
But as I finished pulling up my pants and tucking in my shirt
once again Donna told me she was giving me a raise for my being
a good secretary and such a good sport. She then handed me
another package and told me how nice I would feel with a
pedicure! Then once back at my desk I noticed the nail polish
and other do-dads in the package!
The days went by and with the workload I found I actually forgot
about the panties and pantyhose from time to time, just like
Donna had said by saying "don't worry, you'll get used to them
in no time."
With another week came another feminine addition to my lingerie
wardrobe, and then another, and another! The following Monday I
was standing in Donna's office before starting work while she
looked me over once again. By now, she really had me decked out!
I was wearing my panties and pantyhose complete with my now red
nailed pedicure done up in a bright gloss red that showed
through the toes of the stockings. She had also added a tight
girdle briefer panty to my wardrobe and showed me how she wanted
me to "tuck" myself so I wouldn't show a bulge. Finally, she had
me wear a pair of white nylon pants liners and finished the look
with a matching, lace trimmed nylon camisole! I was now,
underneath, totally dressed!
I begged her to let me take off the camisole saying the straps
would show through my shirt but she wouldn't have any of it! She
said if I was worried I should start wearing T-shirts and / or
keep my suit coat on at all times. I thought the next step was
the last straw though because the following Monday, she brought
a pair of high heels to work that were in my size!
The shoes were black patent leather pumps and Donna made sure to
get a pair with open toes to show off my painted toe nails! I
was grateful that most of our work was corporate and didn't
involve a lot of walk in traffic but I drew the line at wearing
high heels and complained immediately!
"What are you doing to me Donna!?" I asked with a quizzical
glare as I stared at her. But she only smiled with her usual air
of authority knowing full well who was in control.
"I thought you said 'who'll know' and that nobody could tell I
was wearing ladies lingerie? If I wear these shoes around the
office what happens when somebody comes in!?" I said in a
terrified tone. "They'll freak out!"
"Don't worry!" She said. "You just get yourself a pair of
loafers and keep them under your desk. Then, if someone comes
into the office you can change shoes without them knowing."
"But what about these nylons?" I said pointing to my ankles.
"Your pants are long enough, just put your dress socks in the
drawer until you leave at night."
She had it all figured out and even though I tried to argue
further it did no good. Then she told me If I could learn to
master the heels in a week she would give me another raise!
It became very strange almost surreal. She watched as I went
back to my desk and took off my wingtips and black dress socks.
My nyloned feet complete with red nail polish were now clearly
evident! And worse now because I was stepping into women's high
heeled shoes! Donna smiled with satisfaction at seeing them on
me.
She had to help me stand at first and giggled as I wobbled on
the five inch stiletto heels as I moved around the office doing
nothing more than trying not to fall. She had me continue to
practice and coached me how to step until I started walking a
little better. She then returned to her office. An hour later I
heard her ask me to bring her in a fresh cup of coffee. I knew
what she wanted, she wanted to see me mincing on the heels and
did just that as I carefully made my way into her office with
the hot coffee. Donna thanked me then watched as I teetered, the
heels forcing my hips into a slight wiggle as I moved back to my
desk. And that's how it went.
As the days went by I would put on the high heels immediately
after arriving to work and leave them on until my lunch break.
After lunch however, it was back in the heels! The following
Thursday I was just finishing putting away some files in the
cabinet and walking back to my desk. It wasn't five minutes
later that a gentleman came into the office wanting to talk with
Donna! I managed to slip out of the heels and put my new slip on
loafers on and then escort the man in to see Donna! After he
left I had to put the heels back on but I was shaken from the
incident and complained to Donna about it.
She then said we were taking the next week off! I asked why and
she replied "if you are worried about wearing the high heels we
can do something about it so you won't look or feel so out of
place. And since you're getting so good in walking in them it'll
be easy." She said with another of her smiles and finished by
telling me that I would be spending the entire week at her home.
I had an inkling of what was going to happen but not to the
degree it happened! I threatened to quit and didn't really care
but Donna was insistent and with an even larger raise being
offered I felt almost stuck somehow. The job wasn't that hard,
even in the heels but I knew after I was told the rest of
Donna's plan that I could never pull it off.
The first thing I was to do was pack up and move out of my
apartment. I would be living with Donna now and after she was
finished with me there would be no way I could really go back to
my place anyway. Then the next week passed, and with the fifteen
hour days and all the work it passed slowly! But soon it was
Monday morning and the start of another work week.
I was terrified to get out of the car when we pulled up to the
office but Donna insisted that I could make a go of it and that
no one would even notice my changes. I was just the "new"
secretary. I was nervous as I opened the car door and felt the
click of my high heels as they hit the pavement. I took my purse
and after leaving the car I made my way up the sidewalk with
Donna. I could feel my new bust jiggling and feel the cool
morning air swirling around my nyloned legs! And could hear the
swish of my nylons brushing my calves and thighs with each step
as I minced along in my tight, satin lined skirt on those five
inch heels! I saw a few people moving about and driving past on
the street but nobody pointed, or laughed or yelled out. I did
notice a few women give me a passing glance as they went about
their business and a few men looking me over as we made our way
to the office door.
Once inside I was now the "new" secretary and would be known as
Deborah. I hung my car coat up, set my purse on my desk then
went about my regular duties by making coffee. Donna looked me
over.
"Yes, you're a proper little secretary now, very nice, very
ladylike." Then, issuing a satisfied smile she went into her
office.
In being off for a week there was a lot of mail and paperwork to
file and catch up on. I finished with the coffee then swished
into Donna's office to deliver her cup. She noticed me mincing
on the heels, my shiny nylons swishing under my tight pencil
skirt and my bust jiggling under my satin blouse as I set the
cup on her desk.
"Thank you Deborah dear" she said as she casually went back to
work.
"Yes ma'am" I replied as I returned to my duties.
I sat down at my typewriter and was glad that Donna didn't have
my salon nails made that long. This way they were short enough
so I could still type. And I had a lot of correspondence to
answer and a lot of typing to do. So I set to work. A couple
hours later Donna left for downtown on a couple errands and I
decided to stay through lunch to stay safe at the office on my
first day totally dressed as a woman, and to get the extra work
done.
I took phone calls, answered letters and did my filing as usual
then noticed myself in the mirror at the new look Donna had
helped to give me. I ran my hands over my feminized form and was
astounded! She had dressed me from head to toe and from the skin
out! She had gotten me a complete new wardrobe so I would be
able to look like the perfect little feminine lady every day
around the office. She had corseted my waist, and gotten me a
well padded girdle that really widened my hips and rounded my
bottom, and I could feel the weight and jiggle from the silicone
breast forms that now sat snugly in the cups of my satin
brassiere under my lacy, white nylon full slip and my blue, long
sleeved satin blouse with high collar and large satin sash bow
at the front.
My eyebrows had been plucked into a high and feminine arch now
and my ears had been pierced. I could feel the gold hoops as
they dangled against my neck from under my long hairdo that was
now dyed a bright blonde and fixed in a feminine style that
parted in the middle and feathered away from my face in large
sweeping curls. I was slightly built and small in stature to
begin with but looked nothing like a man anymore and any
masculine nuances I had were now hidden by Donna's intensive
week long training session and any left over manly traces were
now totally muted, covered up and totally concealed by the
ladies clothing, hairstyle, makeup, perfume and jewelry.
The days and weeks passed. And although we had little walk in
traffic, no one ever suspected that I was a man. They simply saw
the name plate "Deborah" and behind the desk a feminine, shapely
lady going about her secretarial duties as the scent of perfume
hung in the air and the sound of swishing nylon echoed through
the office whenever I moved in my seat or crossed my legs!
Love Ya
By: Vickie Tern
"Yes, Carl, I do know you've been feeling stressed lately, and also
that you aren't too happy with my schedule these days, my long hours at
the office and my evenings with clients, and so on. But as I keep
explaining, that's the price we both have to pay if I'm to earn the
money that provides you the freedom to stay home and perfect whatever
this ... this digital whatsis thing that obsesses you. Yes, suspicious
and depressed doesn't cover half of what you feel, I know that! You
think what you wish, but I've got some good news for you! I've been
talking about this situation with some people I know and I've got the
perfect solution! The perfect anodyne, really, in a way. You take
just one of these each morning, at first, no more, and then you'll find
you feel a lot better about lots of different things. By the time a
week's gone by, no more problems, or anyhow, nothing you'd consider a
problem, which is the same thing after all. Oh, don't make a fuss,
baby, this is for both of us! Now open up like a great big baby bird,
and ... that's it!"
***************
"Hi honeybun. Oh, what a lovely kiss. I told you those pills would
help you feel more comfortable about everything! Only a week since we
added the last two, and already you're so much more relaxed, and
affectionate, and you feel so much softer too! That extra hour's nap
each morning after you take the pink one does you no harm either, I'm
sure. Yes, isn't her voice soothing in those soft, foamy earphones?
Margaret is the first one's name, as I recall, but she's only the first
in a long series. I'm told you'll be hearing a number of different
women's voices advising you how to relax and forget your troubles be
more of yourself while you're asleep. Now come into the kitchen with
me and help me get dinner ready -- after all, you'll soon be wanting to
do it all on your own, won't you?
***************
A margarita to greet me at the door, and made with fresh-squeezed limes
too! Is that what I've been missing all this week when I was working
so late at the office? I should try to get home earlier! Oh, and
dinner is ready already? I should ytell you, Carl, I may need to go
out later this evening for another meeting with a client. Don't worry,
Bob will be with me this time -- he'll be picking me up, and he'll
bring me home too when we're done, so there'll be no need for you to
worry about my driving home alone when its late and I'm tired."
***************
"Never mind dinner for me tonight, honey. Clark and I will be dining
together later on. Be sure to get to bed early -- I may want to bring
him home afterward. Oh yes, I've meant to tell you, use the spare room
this time just in case I do bring him home -- you might as well get
used to it, that's your own special private place from now on. It'll
be much more convenient for you for fixing breakfast for me and any ...
guests, since it's just off the kitchen. I've already moved your
undies and low-heeled shoes and a work dress and so on into the closet
there, along with some of the make-up Bernice showed you how to use.
From now on, do make up your face each morning, just a little.
Sparingly -- you do need to look proper and presentable and all when we
have guests, but no more than that. I'm the gorgeous member of this
household after all!"
*****************
"Oh, God, I'm so tired, I haven't danced this much since before our
marriage -- I mean my marriage. I'm glad you waited up, though, Carla.
Craig will be here in a moment -- see if he needs anything, and plan on
serving us both breakfast at eight tomorrow morning. In bed this time
if you don't mind. Oh yes, tomorrow I think you'd better look into
getting yourself a new cotton dress for cleaning the house and so on --
that one we got you a month or so ago is beginning to show wear. Maybe
it's time for you to accept a real maid's uniform, mob cap and all?
Wouldn't you like that?"
*****************
"You look perfect, sweetheart! Just darling! With your cheeks so pink
and puffy and your eyes so bright! Oh, I've meant to tell you before,
when you're dressed like that don't call me 'Sue' or 'Susan,' not any
longer -- it creates a bad impression when the maid acts too familiar.
'Ms. Everson' will do fine -- yes, that's right, my maiden name. Don't
worry, you and I will know we're still married, but we won't want
others wondering whatever became of my former husband, if there ever
was one, do we? It might be embarrassing for you. 'My former
husband,' if anyone should ask you directly, remember, that's what we
agreed to call him. When I bring gentleman friends home from now on I
don't want any of them feeling in any way inhibited -- you can
understand that now that you and what's-her-name, the Sloane's maid,
Theresa, now that you and Theresa have started going out to try to meet
guys together on your evening off each week."
******************
"Oh, don't worry about it at all, Carla. Your hairdo's perfect and
those make-up lessons at the Community College have certainly paid off.
Jimmie will think you're incredibly lovely and that he's a lucky guy
that someone as beautiful as you is willing to go out with him at all.
You have no reason to be nervous about yourself one bit. And your
dress is perfect too -- satin may be a bit flashy for this kind of
date, it's not at all what I'd wear, but it's a lovely gown, and it's
what you chose at the consignment shop, and certainly he'll love how it
feels when you're slow dancing with him. How you feel in it. Just
remember what I told you -- when he takes you home, no good night
kisses on the cheek or lips or anywhere else, not until you finish your
laser treatments and the skin on your face is as smooth as mine. Above
all, no parking and making out! That's way too risky -- if he gets his
hands into you down there he may just discover what you've got and what
you don't have, and ... ahhh ... lose all interest in you. So when he
brings you back here, just before you get out of his car, surprise him!
Unzip his pants and take him into your mouth and pull on his thing and
suck on it for a while, and then when he comes, swallow it all up and
then give him a delicious big smile! I guarantee he'll call you for
another date tomorrow morning if he doesn't ask you out again then and
there. Oh, sweetheart, of course, I learned that way back in high
school, all girls know that, you don't?"
******************
"I agree, Carla. While Craig and I -- remember, he's now Mr. Craig to
you -- are on this Bermuda cruise, that'll be the perfect time for you
to go get your thingies removed and a proper pussy installed. Tell
Jimmie you're going with us and then you can check into the hospital
the day we leave. Tell him that when you get back you'll have a
marvelous surprise for him -- no more insisting he use only your rear
so you won't get pregnant, that now you want him to have all of you.
I'll suggest to Dr. Berenson that he enhance your boobs a little too --
that'll add to Jimmy's pleasure when he finally gets to see you again,
and yours too when Jimmy decides to show you how much he appreciates
them. It'll open up other possibilities with other guys too. Honey, I
think you can do better than Jimmy. I'm told that the Gottfrieds have
gotten themselves a new chauffeur and handyman who's a real go-getter
and a hunk to boot, a Tim Something. I tell you what, when Craig and I
return I'll invite the Gottfrieds to dinner, and that'll give you ample
opportunity to meet and chat with Tim and then we'll all see if
anything develops."
********************
"Don't worry about it, Carla dear. Girls tell all sorts of stories
about their early years, some of them true and some of them they should
only wish. If you can't remember your own girlhood, or anything at all
about your life before you began to work here as my live-in maid, well,
so much the better. Make up whatever stories you like whenever you get
together with other girls on their days off, or when you're chatting
with dates. They'll respect you all the more if you've had a life like
the girls in those Harlequin romances you've been reading -- they never
read novels like that, so they won't have the foggiest that you're
borrowing someone else's story. Oh, I won't need you tonight after
you've cleared the dishes and straightened up, so you can go to your
room early, or maybe go to a movie, or do whatever you like. Just
don't stay out late if you go out -- I'll be bringing Craig home, and
he needs to be up at six to make a plane first thing tomorrow, so his
breakfast will need to be ready strictly at six-thirty. Just for him -
- I'll be sleeping in."
*********************
"Honey, if Tim wants to take you to a downstate resort this weekend, I
don't mind. I can do without you this one weekend. I won't be
entertaining, and Jimmy won't ever need to know. You think of something
to tell him -- I can't cover for you all the time, especially not this
time, because Scott and I will be going out of town ourselves. Oh, of
course, just tell him you're going with us. My goodness, I should
think you'd know by now, no girl ever needs to be with only one guy at
a time. She only needs to seem to be going with that one guy, and only
as far as he's concerned. I mean, when I was married to Carl -- you've
heard me mention him even though he was before your time -- well, I
can't begin to name the other men I was also seeing, and Carl was so
preoccupied with his own things he almost never noticed. Until one day
he began to suspect and ... well, luckily, I found out he was
suspicious before he found out I did, so I had time to ask around what
to do about it. Anyhow, it's the same thing with Craig these days. He
doesn't know a thing about Scott, not even about Duncan, and Duncan is
his best friend he thinks, can you imagine? Men! Anyhow, go, do enjoy
yourself honey! Enjoy Tim and any of the other men you may meet there,
but regardless, don't forget, no matter where you may be, first thing
when you wake up every morning -- no matter who's in your bed or what
you've been doing with him -- you must take your pills! All of them!
We don't want you ever having bad thoughts about anything, right? And
now that you have a figure that can stop a clock, certainly stop
traffic, you won't ever want to lose it! No more than I want to lose
the prettiest maid any girl ever had!"
"Oh, sweetheart, you're always so gentle, the way you brush my hair
when you're getting me ready for a date! I hope you're as pleased as I
am. This is so nice! So much nicer than when Carl lived here! Love
ya!"
"Yes, Carl, I do know you've been feeling stressed lately, and also
that you aren't too happy with my schedule these days, my long hours at
the office and my evenings with clients, and so on. But as I keep
explaining, that's the price we both have to pay if I'm to earn the
money that provides you the freedom to stay home and perfect whatever
this ... this digital whatsis thing that obsesses you. Yes, suspicious
and depressed doesn't cover half of what you feel, I know that! You
think what you wish, but I've got some good news for you! I've been
talking about this situation with some people I know and I've got the
perfect solution! The perfect anodyne, really, in a way. You take
just one of these each morning, at first, no more, and then you'll find
you feel a lot better about lots of different things. By the time a
week's gone by, no more problems, or anyhow, nothing you'd consider a
problem, which is the same thing after all. Oh, don't make a fuss,
baby, this is for both of us! Now open up like a great big baby bird,
and ... that's it!"
***************
"Hi honeybun. Oh, what a lovely kiss. I told you those pills would
help you feel more comfortable about everything! Only a week since we
added the last two, and already you're so much more relaxed, and
affectionate, and you feel so much softer too! That extra hour's nap
each morning after you take the pink one does you no harm either, I'm
sure. Yes, isn't her voice soothing in those soft, foamy earphones?
Margaret is the first one's name, as I recall, but she's only the first
in a long series. I'm told you'll be hearing a number of different
women's voices advising you how to relax and forget your troubles be
more of yourself while you're asleep. Now come into the kitchen with
me and help me get dinner ready -- after all, you'll soon be wanting to
do it all on your own, won't you?
***************
A margarita to greet me at the door, and made with fresh-squeezed limes
too! Is that what I've been missing all this week when I was working
so late at the office? I should try to get home earlier! Oh, and
dinner is ready already? I should ytell you, Carl, I may need to go
out later this evening for another meeting with a client. Don't worry,
Bob will be with me this time -- he'll be picking me up, and he'll
bring me home too when we're done, so there'll be no need for you to
worry about my driving home alone when its late and I'm tired."
***************
"Never mind dinner for me tonight, honey. Clark and I will be dining
together later on. Be sure to get to bed early -- I may want to bring
him home afterward. Oh yes, I've meant to tell you, use the spare room
this time just in case I do bring him home -- you might as well get
used to it, that's your own special private place from now on. It'll
be much more convenient for you for fixing breakfast for me and any ...
guests, since it's just off the kitchen. I've already moved your
undies and low-heeled shoes and a work dress and so on into the closet
there, along with some of the make-up Bernice showed you how to use.
From now on, do make up your face each morning, just a little.
Sparingly -- you do need to look proper and presentable and all when we
have guests, but no more than that. I'm the gorgeous member of this
household after all!"
*****************
"Oh, God, I'm so tired, I haven't danced this much since before our
marriage -- I mean my marriage. I'm glad you waited up, though, Carla.
Craig will be here in a moment -- see if he needs anything, and plan on
serving us both breakfast at eight tomorrow morning. In bed this time
if you don't mind. Oh yes, tomorrow I think you'd better look into
getting yourself a new cotton dress for cleaning the house and so on --
that one we got you a month or so ago is beginning to show wear. Maybe
it's time for you to accept a real maid's uniform, mob cap and all?
Wouldn't you like that?"
*****************
"You look perfect, sweetheart! Just darling! With your cheeks so pink
and puffy and your eyes so bright! Oh, I've meant to tell you before,
when you're dressed like that don't call me 'Sue' or 'Susan,' not any
longer -- it creates a bad impression when the maid acts too familiar.
'Ms. Everson' will do fine -- yes, that's right, my maiden name. Don't
worry, you and I will know we're still married, but we won't want
others wondering whatever became of my former husband, if there ever
was one, do we? It might be embarrassing for you. 'My former
husband,' if anyone should ask you directly, remember, that's what we
agreed to call him. When I bring gentleman friends home from now on I
don't want any of them feeling in any way inhibited -- you can
understand that now that you and what's-her-name, the Sloane's maid,
Theresa, now that you and Theresa have started going out to try to meet
guys together on your evening off each week."
******************
"Oh, don't worry about it at all, Carla. Your hairdo's perfect and
those make-up lessons at the Community College have certainly paid off.
Jimmie will think you're incredibly lovely and that he's a lucky guy
that someone as beautiful as you is willing to go out with him at all.
You have no reason to be nervous about yourself one bit. And your
dress is perfect too -- satin may be a bit flashy for this kind of
date, it's not at all what I'd wear, but it's a lovely gown, and it's
what you chose at the consignment shop, and certainly he'll love how it
feels when you're slow dancing with him. How you feel in it. Just
remember what I told you -- when he takes you home, no good night
kisses on the cheek or lips or anywhere else, not until you finish your
laser treatments and the skin on your face is as smooth as mine. Above
all, no parking and making out! That's way too risky -- if he gets his
hands into you down there he may just discover what you've got and what
you don't have, and ... ahhh ... lose all interest in you. So when he
brings you back here, just before you get out of his car, surprise him!
Unzip his pants and take him into your mouth and pull on his thing and
suck on it for a while, and then when he comes, swallow it all up and
then give him a delicious big smile! I guarantee he'll call you for
another date tomorrow morning if he doesn't ask you out again then and
there. Oh, sweetheart, of course, I learned that way back in high
school, all girls know that, you don't?"
******************
"I agree, Carla. While Craig and I -- remember, he's now Mr. Craig to
you -- are on this Bermuda cruise, that'll be the perfect time for you
to go get your thingies removed and a proper pussy installed. Tell
Jimmie you're going with us and then you can check into the hospital
the day we leave. Tell him that when you get back you'll have a
marvelous surprise for him -- no more insisting he use only your rear
so you won't get pregnant, that now you want him to have all of you.
I'll suggest to Dr. Berenson that he enhance your boobs a little too --
that'll add to Jimmy's pleasure when he finally gets to see you again,
and yours too when Jimmy decides to show you how much he appreciates
them. It'll open up other possibilities with other guys too. Honey, I
think you can do better than Jimmy. I'm told that the Gottfrieds have
gotten themselves a new chauffeur and handyman who's a real go-getter
and a hunk to boot, a Tim Something. I tell you what, when Craig and I
return I'll invite the Gottfrieds to dinner, and that'll give you ample
opportunity to meet and chat with Tim and then we'll all see if
anything develops."
********************
"Don't worry about it, Carla dear. Girls tell all sorts of stories
about their early years, some of them true and some of them they should
only wish. If you can't remember your own girlhood, or anything at all
about your life before you began to work here as my live-in maid, well,
so much the better. Make up whatever stories you like whenever you get
together with other girls on their days off, or when you're chatting
with dates. They'll respect you all the more if you've had a life like
the girls in those Harlequin romances you've been reading -- they never
read novels like that, so they won't have the foggiest that you're
borrowing someone else's story. Oh, I won't need you tonight after
you've cleared the dishes and straightened up, so you can go to your
room early, or maybe go to a movie, or do whatever you like. Just
don't stay out late if you go out -- I'll be bringing Craig home, and
he needs to be up at six to make a plane first thing tomorrow, so his
breakfast will need to be ready strictly at six-thirty. Just for him -
- I'll be sleeping in."
*********************
"Honey, if Tim wants to take you to a downstate resort this weekend, I
don't mind. I can do without you this one weekend. I won't be
entertaining, and Jimmy won't ever need to know. You think of something
to tell him -- I can't cover for you all the time, especially not this
time, because Scott and I will be going out of town ourselves. Oh, of
course, just tell him you're going with us. My goodness, I should
think you'd know by now, no girl ever needs to be with only one guy at
a time. She only needs to seem to be going with that one guy, and only
as far as he's concerned. I mean, when I was married to Carl -- you've
heard me mention him even though he was before your time -- well, I
can't begin to name the other men I was also seeing, and Carl was so
preoccupied with his own things he almost never noticed. Until one day
he began to suspect and ... well, luckily, I found out he was
suspicious before he found out I did, so I had time to ask around what
to do about it. Anyhow, it's the same thing with Craig these days. He
doesn't know a thing about Scott, not even about Duncan, and Duncan is
his best friend he thinks, can you imagine? Men! Anyhow, go, do enjoy
yourself honey! Enjoy Tim and any of the other men you may meet there,
but regardless, don't forget, no matter where you may be, first thing
when you wake up every morning -- no matter who's in your bed or what
you've been doing with him -- you must take your pills! All of them!
We don't want you ever having bad thoughts about anything, right? And
now that you have a figure that can stop a clock, certainly stop
traffic, you won't ever want to lose it! No more than I want to lose
the prettiest maid any girl ever had!"
"Oh, sweetheart, you're always so gentle, the way you brush my hair
when you're getting me ready for a date! I hope you're as pleased as I
am. This is so nice! So much nicer than when Carl lived here! Love
ya!"
Recruiting Letter
By: Sweet Sabrina
Dear Reader:
You have been sent this letter, because we have reason to
believe you may be qualified for and interested in a
position in our firm as an Executive Secretary. Some
details regarding the position follow.
Policies
1. Executive secretaries are considered to be on duty 24/7/365.
2. Dress code applies whenever secretary is on duty.
3. Each secretary reports directly to one executive.
4. Secretary must address that executive as Master or
Mistress as appropriate.
5. Secretary will address other executives as Sir or Madam
as appropriate.
6. Secretary's Master or Mistress will determine the name that
the secretary will be called.
7. When in the presence of Master or Mistress, secretary will
kneel at his or her feet.
8. When walking in Master or Mistress' company, secretary
will walk 2 steps behind and to the right.
9. Secretary will perform all tasks assigned without
complaint or hesitation.
10. Any failure to follow policies and/or dress code will
result in any disciplinary action deemed appropriate by the
executive.
11. When an executive is forced to take time from his or
her busy schedule to discipline a secretary, secretary will
show proper gratitude immediately.
12. No executive secretary will hold the position for more
than five years, after which time, secretary will be
reassigned within the company or released at her choice. If
release is chosen, letters of recommendations will be
given.
Dress Code
1. Skirts and dresses must end no lower than 3" above the
knee.
2. Shoes must have no less than 4" heels.
3. These shoes may be pumps or sandals, but must strap on
to prevent the temptation to kick the shoes off when at
your desk, as this is prohibited.
4. Nail polish and lipstick must be stylish and must match
(black and other Goth colors are not acceptable).
5. No clothes may be larger than a size 6.
6. Hair must be at least shoulder length and styled
fashionably.
7. Garter belt and stockings must be worn at least twice a
week.
8. No outfit may be worn more than twice in any month.
9. Jewelry will be tasteful and classy; wedding rings are
not permitted. Earrings and ankle bracelets are required at
all times.
10. Chastity devices will be worn at all times unless
removed by an executive. The executive decides who will be
given keys to the chastity device.
11. Friday (casual day) outfits may vary from standard, but
must be approved by H.R. Manager and the secretary's
manager before being worn.
12. Any executive may check at any time to ensure that the
secretary is in compliance with all aspects of the dress
code.
As an outsider reading the above you probably think this is
a company just waiting for a sexual discrimination suit.
However, the company has never been sued and should not be
sued anytime soon. As Director of Human Resources, I have
been careful to make sure that the executive secretaries to
whom the above policies apply have the same gender ratios
as the rest of the company and the rest of the community of
the home office. We currently have 5 male and 6 female
Executive Secretaries. Since we have 12 positions we are
currently looking for 1 male who meets the requirements and
can perform the duties listed above.
As you can see from policy 12 this position can be a great
boost to a young person's career. In fact two of our
directors were once executive secretaries here and many
others have good positions with other firms. For someone
like yourself, 5 years experience as an executive secretary
could well be the beginning of the life you have dreamed of
for so long. I will not deny that the work is hard, and the
executives are extremely demanding, but the rewards are
worth it. (The salary is also generous, but I doubt that
salary is your main concern.) If you are interested in the
position and I am sure you are, please send a current photo
with application.
Sincerely,
Richard Johnson
Human Resources Director
Dear Reader:
You have been sent this letter, because we have reason to
believe you may be qualified for and interested in a
position in our firm as an Executive Secretary. Some
details regarding the position follow.
Policies
1. Executive secretaries are considered to be on duty 24/7/365.
2. Dress code applies whenever secretary is on duty.
3. Each secretary reports directly to one executive.
4. Secretary must address that executive as Master or
Mistress as appropriate.
5. Secretary will address other executives as Sir or Madam
as appropriate.
6. Secretary's Master or Mistress will determine the name that
the secretary will be called.
7. When in the presence of Master or Mistress, secretary will
kneel at his or her feet.
8. When walking in Master or Mistress' company, secretary
will walk 2 steps behind and to the right.
9. Secretary will perform all tasks assigned without
complaint or hesitation.
10. Any failure to follow policies and/or dress code will
result in any disciplinary action deemed appropriate by the
executive.
11. When an executive is forced to take time from his or
her busy schedule to discipline a secretary, secretary will
show proper gratitude immediately.
12. No executive secretary will hold the position for more
than five years, after which time, secretary will be
reassigned within the company or released at her choice. If
release is chosen, letters of recommendations will be
given.
Dress Code
1. Skirts and dresses must end no lower than 3" above the
knee.
2. Shoes must have no less than 4" heels.
3. These shoes may be pumps or sandals, but must strap on
to prevent the temptation to kick the shoes off when at
your desk, as this is prohibited.
4. Nail polish and lipstick must be stylish and must match
(black and other Goth colors are not acceptable).
5. No clothes may be larger than a size 6.
6. Hair must be at least shoulder length and styled
fashionably.
7. Garter belt and stockings must be worn at least twice a
week.
8. No outfit may be worn more than twice in any month.
9. Jewelry will be tasteful and classy; wedding rings are
not permitted. Earrings and ankle bracelets are required at
all times.
10. Chastity devices will be worn at all times unless
removed by an executive. The executive decides who will be
given keys to the chastity device.
11. Friday (casual day) outfits may vary from standard, but
must be approved by H.R. Manager and the secretary's
manager before being worn.
12. Any executive may check at any time to ensure that the
secretary is in compliance with all aspects of the dress
code.
As an outsider reading the above you probably think this is
a company just waiting for a sexual discrimination suit.
However, the company has never been sued and should not be
sued anytime soon. As Director of Human Resources, I have
been careful to make sure that the executive secretaries to
whom the above policies apply have the same gender ratios
as the rest of the company and the rest of the community of
the home office. We currently have 5 male and 6 female
Executive Secretaries. Since we have 12 positions we are
currently looking for 1 male who meets the requirements and
can perform the duties listed above.
As you can see from policy 12 this position can be a great
boost to a young person's career. In fact two of our
directors were once executive secretaries here and many
others have good positions with other firms. For someone
like yourself, 5 years experience as an executive secretary
could well be the beginning of the life you have dreamed of
for so long. I will not deny that the work is hard, and the
executives are extremely demanding, but the rewards are
worth it. (The salary is also generous, but I doubt that
salary is your main concern.) If you are interested in the
position and I am sure you are, please send a current photo
with application.
Sincerely,
Richard Johnson
Human Resources Director
10 March 2011
Intimacy
By: Bea
"Miss Matson will see you now, Mr. Ellis, but she's asked me to tell
you that she has a busy schedule this morning and will not be able to
spare you much time."
I looked at this perfect example of a modern secretary. Immaculate,
frozen faced, and dressed in a most conservative – but extremely
feminine style. Wanted to put her in her place – SO badly, but knew
that I was in no position to annoy anyone in Gloria Matson's employ, so
smiled as nicely as I could. "Thank you very much," I said humbly. She
looked down her nose at me and flipped her head in a sideways motion to
indicate that I was to go in to Gloria's office. I edged past her into
where Gloria sat making notes on a paper on her desk in front of her.
"Yes? What do you want?" she asked rudely, without even looking up,
before her secretary had enough time to shut the door behind me. I
flushed.
"Gloria? I received your letter this morning. We need to talk. Please?"
She stopped writing and put her pen down. Looked up at me.
"NEED to talk? Harold? Maybe YOU need to talk to me – but I don't see
ME needing to talk to you!"
"Well, some professional courtesy wouldn't be amiss!" I retorted, my
face reddening.
"My goodness! The little bunny has a temper, does he?" she said, openly
sneering.
"Now as I heard Edna tell you, I don't have much time for you. But I
can make some – if you wish?"
Gloria Matson is a high priced attorney with a mind like a steel trap –
absolutely beautiful in a dark Mediterranean way. Always impeccably
dressed, no hair out of place, obviously rich from the custom designed
jewelry she wears – not chunky – but sleek and expensive – like her.
Frankly speaking, she scares and intimidates me normally – and at that
moment, she held my career in her hands – and knew it. Knowing that
retreat was my only viable option, I softened my tone. "That would be
very nice if you could do that Gloria. I'd really appreciate it."
She gave me a predatory smile. "I'll tell you this up front. I'm going
to humiliate you. Really put you down. I've looked forward to doing
something like this to you for a LONG time and I want you to know this
before I start. You understand what I'm saying? Accept this?" I could
see there was no give in her. Nodded.
"Very well. Both of us know why you're here and both of us know that
I'm the one person in this world that can help you. You have been very
naughty Harold so, know what I want you to do for a start?" She paused,
looking at me intently. Pointing at the corner of her office diagonally
across from her desk she told me, "Go over there and stand in the
corner. I'll let you know when you can come out again. Now?" she jerked
her thumb. "GIT!"
I looked at her in amazement. She meant it! Licked my lips. Swallowed.
"You gotta be kidding. Come on Gloria. Stop with this nonsense. Huh?"
A look of unholy glee crossed her face as she saw my weak indecision.
Somehow knew that I would do as she said. Showed her teeth as she bared
her lips. "You weakling! You namby pamby weakling! Go and stand in the
corner! Or leave this office and never come back. NOW!" I had no
choice. Went over to a corner and stood there. "Face INTO the corner!"
she barked. I did.
She actually kept me standing there for almost an hour! An hour in
which she chatted with friends on the telephone, ordered some clothes
the same way – made it very obvious that I was less important to her
than any of these minor chores. Then she called through to her
secretary. "Edna? Do you have a moment please?"
I heard Edna come in to the office. "Yes Miss Matson?" From the way her
voice changed I got the impression she saw me and was enjoying my
discomfiture.
"Grab a chair. Make yourself comfy. Is there any coffee in the
machine?"
"Yes. Would you like me to get you a cup?"
"No. Not yet. Harold?"
I breathed a sigh of relief, my legs were killing me! I turned around.
"Yes Gloria?"
"I did NOT tell you to turn around! Face back into that corner! And
from now on? I'm MISS Matson to you! Understand?"
Shamefaced at allowing myself to be talked to in this manner, I turned
around again. "Yes, Miss Matson." I said meekly. Was sure I heard a
giggle from Edna.
"Very well! Now you can come and stand over here in front of my desk!"
The humiliation was so intense that I felt the tears come into my eyes.
Gloria's keen eyes saw this immediately. "Would you just LOOK at this
pussy, Edna. Crying! Like a goddam woman!"
She pointed to a spot on the floor. "Stand there – and while you're at
it? Clasp your hands in front of you and place them down over your lap.
That's how maids stand when talking to their mistresses. That's how you
will stand when I address you from now on. Good!"
She turned to Edna. "Isn't he just the nicest, softest, marshmallow?
Standing there, just waiting for his mistress to tell him what to do?"
Edna giggled, then Gloria turned her attention back to me. "Tell you
what pussy. Go to the outer office there and get me and Miss Edna a cup
of coffee. You'll find a tray there. Both of us like our coffee black.
Don't dawdle! Off you go!"
I reddened at what I was about to say. "Yes Miss Matson – but is there
a bathroom I can use? Please?"
She smiled gleefully, "Pussy need a wee wee?" I nodded, shame faced.
"Okay – you can use ours. It's a LADIES room. You won't mind using it,
I trust?"
"No, Miss Matson."
"Very well! But if you are going to tinkle in a Ladies? Please sit down
like one. Can I trust you to sit and pee like a good girl?"
"Yes Miss," I said – so desperate that I'd have promised the moon..
She waved her hand in dismissal and I rushed into their private
bathroom – which WAS very feminine in it's set up. Sat down as
requested, and relieved myself. This turned out to be more difficult
than I had anticipated because I had an erection, and it took me some
desperate mental exercises to get it down to where I could pee
satisfactorily.
When I finally came out, I saw the coffee machine and the tray. Set up
the two cups – and saucers and filled them with the aromatic brew that
was in the machine. Took them into the ladies – who regarded my
approach with bright, shining, predatory eyes. Took their coffees from
me with polite 'thank you's', then settled back in their chairs,
waiting for me to return to my servant's stance.
"You were very naughty – stealing all that money from your poor old
clients, weren't you?" Gloria said after taking a sip of her coffee.
I felt my knees almost buckle. "Gloria! You know I wouldn't . . "
"Oh hush, you silly pansy! I know damn well you don't have the smarts
to pull that scam!"
I was thoroughly confused. "Well then, why are you treating me this
way? You have been very mean . ." and to my own outrage, felt the tears
begin to well in my eyes again.
"Dearie? The perception one gets from reading all the documentation is
that you ARE guilty. Your partner – Dorothy? That ditzy blonde that
everyone takes for a lamebrain? It was her. But she's got that audit
trail leading ALL the way back to you – your offshore accounts in the
Cayman
islands – your sweet little partnerships? None of which contain any
money of course. Did you just sign EVERY goddam piece of paper she put
in front of you – you stupid idiot?"
"I trusted her!" I wailed, "But if you KNOW she's the guilty one? Why
are you coming after ME?"
"Because sweetie? You're easy meat, she's not. The way things are? I
can get most of the money from you – but don't have a hope in hell of
getting it from Dorothy unless I get your cooperation. I mean to say,
what jury would ever find someone like her guilty? So listen up. Here's
what is going to happen dearie. I'm buying your share in your
partnership with her. Once I'm in? She'll end up refunding most
everything she's stolen back into the proper places. Then? I'll resell
you your share in the partnership – at a considerable discount of
course, I'll tell you up front."
She smiled at me like a Cheshire cat. Sighed happily and took another
sip of her coffee.
I felt relief surge through me. Okay, my stupidity was going to cost
me, I knew, being fully aware that if money was involved, Gloria was
going to pocket a good percentage of it – but at least my family name
wasn't going to be dragged through the mud. "Okay Gloria. Thanks. I
know I deserve to be. . ."
"MISS MATSON you silly cow!" she snarled loudly, almost spilling her
coffee.
"I'm terribly sorry Miss Matson," I groveled. "I forgot. But may I ask
how long this will take?"
She shrugged, calmer now, "How long? A year – maybe two."
"A YEAR!" I squealed. "But what am I to do in the meantime?"
"Work for me, silly! What do you expect? I'm buying you out – amn't
I?"
"But I'm not a lawyer," I said slowly.
"You're not much of anything!" she said snidely. "But I'll make you my
Associate in the running of the office here."
"That's very kind of you Glo – Miss Matson," I said.
She waved her hand airily, "Don't thank me, sweetie. It's Edna here
you'll be reporting to."
"But doing . . what, exactly?" I asked.
"Whatever she tells you, I'd imagine. I trust her implicitly – and
anything she tells you to do? I want you to see it as word coming
directly from God – namely me." Both women smirked. Gloria sniggered
some more. "Now that I think of it? You DO see me as some sort of
goddess I hope?"
I tried to make light of it. "Of course! How else?"
"Let's see," she said, getting up out of her chair and walking to right
in front of me where she stopped. "Get down on your knees!" she purred.
"Show some respect for your new goddess."
"Please miss Matson. Please don't . . ," I started to say, but she
smiled and put a hand on my shoulders, gently forcing her hand
downwards.. "Down you go! There you are. That's it!" she exulted as I
slowly sank to my knees. "Now? Take my shoes off!" she commanded.
She had very elegant feet and shoes whose glossy perfection and obvious
workmanship indicated a very high price tag. Carefully, I took each of
her silken ankles in turn, lifted them and removed the shoes.
"Now kiss my feet sweetie! Nice big sucky kisses! Take my toes into
your mouth and suck on them real good! I'll enjoy it more if you
slobber a little bit."
She made me perform this subservient act while she stood – and had a
conversation with Edna about some movie she'd seen a few nights before.
Then, she finally patted me on the head as if I were a pet.
"That was very nice sweetheart. Did you enjoy that?"
"Yes Miss," I mumbled.
"But isn't Edna your new boss? Don't want to disrespect her, do you?"
"No ma'am"
"Very good! So why don't you crawl over to her and do the same thing,
huh?"
I did start to cry as I crawled over the office floor and performed the
same act for Edna, the only difference being that she was not quite as
elegantly shod – remaining seated, and constantly wiggling her toes
inside my mouth and sighing with pleasure as I attended to her. To
humiliate me further, Gloria came and sat beside her – and put her feet
up on my back as if I was a footstool!
Finally, I was allowed to leave the office after signing some papers –
which Gloria refused to let me read. "Just sign those sweetie. Please
don't try to read them – they'll just confuse your pretty head! And
when you get here tomorrow – eight o'clock SHARP! Report to Edna.
She'll tell you what to do."
Emotionally exhausted I arrived home about an hour later. Pamela, my
lovely sweet wife, was there to greet me. Looked at me and gave me a
lovely, sympathetic hug. "Oh dear! You've been crying. Was it that
bad? Here, come sit beside mummy and tell her all about it."
"It was awful! Really awful! The way Gloria and Edna humiliated me!" I
started and, as she pulled my head into her shoulder, started to weep
copiously.
"What did she do?" she asked dabbing at my eyes with a dainty,
perfumed, handkerchief after my crying had abated.
I didn't tell her everything of course – I mean, a man has his pride
don't you think? I also may have exaggerated my own responses as well,
but all in all, Pamela was suitably impressed by my revised version of
the actual events. "Oh, you wonderfully brave man! To suffer such
indignities for me! No, NO! I cannot let you go on with this! We'll
tell her to do her worst! Tell her to go to HELL!"
I was SO encouraged by my wife's reaction. Felt it to be somewhat on
the melodramatic side, but was strengthened by it. "No dear!" I said
bravely. "It is a sacrifice I'm making, but with you by my side? I can
make it – and do so willingly!"
She shook her head admiringly. "My MAN!" she said. "You may be small
in stature – but you're a GIANT in my eyes!"
Then she smiled tentatively. "But dear? If you're going to go through
with this? We'll have to do what Jenny suggested, don't you think? I
feel just awful asking it of you. But she's been very accurate in
forecasting what Gloria would do so far."
"Damn lawyers! They're all monsters! Takes one to know one!" I growled.
"Yes dear – but Jenny's my friend – she wouldn't steer us wrong. If
you sign the house and bank accounts over to me? Gloria won't have a
chance of laying her sticky hands on them – and that way, when this is
all over? We can simply reverse the process." A hurt look came into her
eyes. "Of course – if you don't trust me?"
I felt a rush of shame for my attitude towards my loving wife. "Oh
darling! Of course I trust you! Did you get all the paperwork from
Jenny?"
"Yes dear. They're over on the table, but are you REALLY sure you want
to go through with this?" She looked at me coyly, her beautiful eyes
shining.
"Of course, my darling!" I said happily.
I had just finished signing a mess of documents, with Pamela taking up
each one into her hands as I signed it. "Well!" I said, clapping my
hands.
"That's that! Gloria will probably be mad – but ask me if I care!"
"My HERO!" she then said, taking me into her arms and kissing me. Not
for the first time, I was surprised by the strength in her arms. Then
she disengaged her lips from mine. "Oh I forgot! She called when you
were on your way home. Said she'd forgotten to talk salary with you."
"Guess I can discuss it with her tomorrow," I said, shrugging.
"No need darling. She discussed it with me. Actually? Considering that
what you're going to be doing – a sort of assistant to her secretary?
I thought her offer most generous, and accepted it for you. She's going
to make out your paychecks to me – putting them directly into my
account."
"I don't understand that." I said, a little put out with the idea of
her discussing my salary with Gloria.
"What's to understand?" she asked.
"I didn't know you had a separate bank account," I said.
"Well – it WAS our joint account," she said "But didn't you just sign
it over to me?"
"I see. I'm sorry, just didn't think. How much is she going to pay
me?"
"More than enough my dear. And don't worry. I'll make sure that you
get enough pocket money." Then she paused. "But something else about
money I'm afraid? Please don't be angry with me darling?" She was
using her little girl voice now, one that always won me over.
"I never could be angry with you sweetheart!" I assured her.
"Well? Gloria said that I've to take your credit cards away . . and .
. you've got to tell me every cent you spend in a day."
"WHAT!" I yelled.
"Well sweetheart? She thinks that you're silly with money – and now
that you're working for her? She just wants me to keep an eye on you is
all. I mean it sounds reasonable – don't you think?"
"I guess so . . I guess." I stammered, seeing everything that amounted
to my independence being removed, item by item.
"Very good then!" she smiled widely. "Now, would you go and pour us
both drinks? We can drink a toast to our new arrangement!"
"Okay dear . . but won't you even give me a hint about how much I'm to
be paid?"
Her smile dimmed. "Drinks please, pet!"
I could see that she was getting a little aggravated, so took off and
poured the drinks. Then she said she was a mite puckish, so I put a
little tray of munchies together for her, then started making dinner.
We chatted quite a long time, then I was stupid and asked her about my
salary again. Her eyes got cold. "Don't you trust me darling?
Frightened I'll steal your money from you?"
"Oh no! It's not that at all! It's just . ."
"Don't you have dishes to do dear?" she said this with a considerable
amount of ice in her tone.
Later on, she wandered into the kitchen when I was just about finished.
She was nice enough to put some dishes away though she was somewhat
distant in her manner. But after I apologized for bugging her about
my wages, she returned to her normal sweet demeanor. "Wonderful! Thank
you dear. We don't need to mention this distasteful subject again, do
we?"
"Not if you don't want to darling." I said, grateful to see myself back
in my wife's good books. Was even more grateful when she took me in her
arms again and kissed me.
The following morning I had to wait outside Gloria's office door until
Edna appeared. She opened the door, and ushered me in. Good morning
Harold," she said, pleasantly enough. "You can go and put a pot of
coffee on. Miss Matson likes that special mix in the cupboard there –
put six heaped measures and make a full pot. But here, before you
start? I have a little present for you to wear while your doing chores
here," and she pulled out a frilly, dainty little half apron of some
filmy material. "Here. get this on. After you've made the coffee, I
want you to dust and vacuum Miss Matson's office – so look sharp!"
"I don't really need that apron though, do I?" I replied.
She just stared at me for a second without replying, then handed it to
me. "Put a nice bow in the back. Think you can do that?"
"Yes," I whispered.
It took me some time to get over wearing such a feminine garment but I
had made coffee and dusted Miss Matson's office by the time she came
in. I was just beginning to vacuum when she entered. "Very good. That
apron looks nice on you. But you can vacuum later. I'm expecting a
client shortly. So put your vacuum away and go and get my coffee."
"Yes Miss Matson," I said and was just about to leave her office when I
heard Edna's voice on the intercom. Gloria? You have a Mrs. Trellis
here to see you. You ready for her?"
Gloria was obviously about to say yes, but stopped when she saw my
expression. "Something wrong?" she asked. "She's a good friend of
Pamela's" I said "and please, I don't want her to see me like this?
Can I take the apron off?"
"Yes – but only if Edna okays it."
"But Edna's out there with Mrs. Trellis. Please let me take it off?"
"No! Find yourself somewhere to hide if it bothers you that much!" She
snapped.
I looked around the office. Okay, I'm very small, but there was
nowhere that I could use. "But there's nowhere . ." I started. She
pursed her lips impatiently and beckoned me around to her side of the
desk, then rolled her chair back to reveal the depth of the well. Go in
there!" she said. Lots of room for a tiny thing like you! Just think of
yourself as a bunny in her burrow. In you go now – quick!"
Seconds later, she was telling Edna to let Mrs. Trellis in, as I
crouched under her desk on my knees.
Gloria did get up to greet her client, but then came back and sat down.
As she did, she hiked her skirt up to reveal a gorgeous black satin
slip, with ultra delicate lace around the hem. Then, after they had
discussed what was going on, she asked Mrs. Trellis to define what she
saw as the problem in her own words.
Mrs. Trellis being a real chatterbox was only too happy and started in
talking. As soon as she did so, Gloria kicked off one of her shoes –
and started probing at my face with it. What she wanted was immediately
clear. Obediently, I took her toes into my mouth and started to lick
and suck them through her nylons. To my amazement and chagrin, her
right hand dropped under the desk, and hiked up her dress and slip to
reveal matching black panties. Slowly, she began to finger herself.
Right in front of me!
When Mrs. Trellis gave signs of slowing down, Gloria let out a small
sigh of contentment before getting back down to work again. Altogether
I was under her desk for over twenty minutes and, once I heard Mrs.
Trellis leave I slowly uncorked myself from my hiding space – legs
cramping - and immediately found myself in an entirely different form
of trouble – Edna!
Her face was a little blotchy and her breathing a little fast and, to
my dismay, she was holding a riding crop in one hand – smacking it into
the palm of the other – a most disconcerting sight to see. "Where WERE
you!" The words formed a question, but it was a statement more than a
question.
"I was hiding from Mrs. Trellis. She's a friend of ours and . . ."
"Did you ASK for my permission to hide?" she snapped.
I felt my knees start to shake. "No Miss Edna. I didn't have time –
and I got permission from Miss Gloria. It was her that suggested it!"
"But you know that you report directly to me?" she was now speaking in
a silky smooth voice.
"Yes Miss Edna."
"Okay? Just to remind you for next time? Drop your pants and bend
over!"
I paused in obeying her, just enough to infuriate her all the more. "If
you don't hurry up?" she hissed, "I'll give you SUCH a hiding!" With
that, she swished the crop venomously through the air! Terrified, I
undid my belt buckle and the fasteners that held my pants.
"Let them fall! And bend over!"
As I obeyed her, from the corner of my eye I saw Gloria return from the
Ladies room. "What's all this then?" she asked at the same time as the
crop whistled through the air and seared my buttocks.
I had not anticipated such a pain. Let out a shriek and jumped about
six inches straight up into the air! Scared both women for a second,
then they started laughing so hard because when I landed, I had a
problem keeping my balance and with my pants down about my ankles was
hopping about the office like an offended kangaroo, rubbing my
posterior and weeping with the pain.
"Oh dear Oh dear!" Gloria was hiccupping, "Thank god I just had a pee!
But why are you punishing him Edna? He just gave me a dreamy toesuck!
Wonderful!"
"He hadn't told me he was going to hide, and anyway? I just felt like
giving him a whipping!" Edna said, the color mounting on her face
again. She whistled the crop through the air again. "C'mere you damn
pansy! I want to give you another couple!"
I wept and pleaded but she just pointed to a spot in front of her. "I'm
not coming to you, dearie! Better get your ass over here! I was just
gonna give you two more. Now? It's three. Keep fooling around, and I'm
gonna raise the count some more!"
They both giggled as I shuffled and hopped to where she pointed,
because she wouldn't let me pull my pants up. Then I was in front of
her, my backside in the air – weeping still and pleading, when Gloria –
of all people – saved me! "Edna? That's a pretty good welt you've
raised on his buttocks. Very unsightly, don't you think?"
"Can't make an omelet without breaking eggs, huh?" Edna replied, then
started to take her stance again.
"It must be very painful – that crop really whistles Edna. Harold?
Does it hurt?"
"Oh YES! Miss Matson, it really DOES!" I whimpered.
I saw her nodding sagely. "Yes, I thought so. Tell me sweetie, would
you rather be hit with the crop or put over her knee and spanked?" she
asked me.
"A spanking! Oh YES!" I answered promptly.
"Aw Gloria! That sounds okay – but I think he's more humiliated this
way!" Edna grumbled.
"Well, maybe we could even it up a little?" Gloria commented. "Harold?
Suppose I told you that if you come in tomorrow, dressed as you are,
you'd get your punishment with the crop?" She paused for a second as if
waiting for an answer. Then, getting none from me. "Or? If you were
wearing nice, satiny, panties – you'd get a spanking instead? Just by
hand?"
"They'd have to be PINK!" Edna stated firmly.
"I think we should leave it up to Harold," Gloria said. "See Harold?
Wear nice panties – pink panties, you simply get a spanking. Don't?
Edna practices her crop technique on you. That simple. Your choice.
That okay by you Edna?"
"I guess!" Edna said grudgingly.
I looked at it this way. I could argue the point – and get whipped by
the crop. Or? Just tell them I'd wear panties tomorrow – give myself
time to think? If she whipped me tomorrow because I wasn't wearing
panties? I'd be no worse off, would I? Eager to defer the punishment
any way I could, I nodded, eagerly.
Edna kept me busy filing and cleaning out the Ladies room and didn't
punish me any more. But by the time the end of the day came, I'd
reconsidered. Hey, I'd told them I'd wear panties – and god knows what
Edna would do to me if I didn't. And who was to know anyway - other
than her and Gloria? Sure, it might be difficult to sneak them past
Pamela – but I did the laundry anyway, so I could probably get away
with it. I wasn't too keen on the idea of buying panties – but I could
always tell the salesgirl that they were for my wife, huh? No problem.
I don't know what possessed me to look in my wallet at quitting time.
I nearly fainted! There was about two dollars there – and my credit
cards were all gone! Pamela must have taken them without telling me!
My delectable wife greeted me with a big hug. "Hi sweetie! I've been
waiting and waiting for you to tell me all about your day! Why don't
you pour us drinks, then you can tell me all about it before you make
dinner."
"Pamela darling? You didn't leave me very much money – and you took
my credit cards. May I have some money?"
"Certainly darling! But what do you need money for? And how much?"
I had absolutely no idea of what panties cost – and it suddenly dawned
on me that I'd no idea where to buy satin panties either!
"I lost a bet," I said, grabbing for the only explanation I could think
of.
"Who do you owe the money to?" she said, knitting her brows with
disapproval. "I can see why Gloria had this idea to control your fiscal
activities! Harold? That is disgraceful behavior!"
"Edna." I quavered – everything was going wrong!
"Well, I shall have a nice long chat with Edna tomorrow! Taking
advantage of her position like that!"
I felt my face begin to crumple, felt tears well in my eyes. "Please
Pamela. Please?"
"No! Harold? I'm not being mean! This is for your own good!" She
suddenly looked at me shrewdly."I have the feeling that you're telling
mummy big fibs. Am I right?"
"Yes Pamela," I mumbled, and the humiliations of the day overcame me
again, and I started to cry.
"Well, come and tell me all about it," she said kindly then took me
over to the sofa. Like the previous evening she embraced me and patted
my eyes with her perfumed handkerchief – but this time, it finally
dawned on me that I was sitting on her lap! Telling her all about my
day – this time a little more honestly.
Her response surprised me. Yes, she was as supporting as ever – but
where I'd expected nothing but scorn from her with regard to the
panties, she was as pragmatic as could be. "I don't know why you're
making so much fuss about wearing panties," was the first thing she
said. "You are simply playing into their hands by reacting this way!"
"I don't understand Pamela. What do you mean?"
"Harold! You knew yesterday that Gloria was going to humiliate you. She
told you that for goodness sake! Right?" I couldn't remember telling
Pamela this, but nodded in agreement. "So now they spank you – and you
act all humiliated – and tell you to wear panties – and you act
humiliated all over again! They're just acting like bullies the world
over. Do something - and get a reaction from you, so think that it was
fun – let's do it some more! And you're humiliated! Just a vicious
circle!"
"But what are you suggesting? That I act like I'm NOT humiliated?"
"EXACTLY! Wear the panties – but not just tomorrow – EVERY day! I've
got lots of pretty ones and can give you all that you need. Let's go
and look you out some right now!"
"You mean that by doing that, they'll stop?"
"Oh, they'll think up something else, I'm sure – but if you still want
to keep the promises you made last night and put up with it? All you
have to do is go along with what they tell you to do – but don't let
out a single PEEP about how embarrassed or humiliated you feel!
Understand?"
It made sense, in a convoluted sort of way – but I was so relieved to
have escaped the scorn I'd thought I'd get from Pamela that I accepted
her ideas enthusiastically. She went to our bedroom while I made the
drinks. When I got there with them, she had about a dozen pair of
panties laid out on the bed. Happy and smiling, she kept pressing one
pair after another into my hands making me say how nice they felt – and
admire the lace, etc. Actually? They did feel very nice to the touch.
"You're blushing!" she accused me.
"Well? It IS kinda embarrassing, you know!" I replied.
"Can't have you acting like this at work tomorrow! Let's get you used
to them!" she said. "Get your shoes, socks, and pants off. Let's see.
Those pink ones are lovely – and just a little shade pinker than that
other pair – these you can wear tomorrow. Okay sweetie! Panty time!"
It was bad enough wearing the panties, but my embarrassment was made
worst a hundredfold and she compounded that by not letting me put my
other clothes on, tying me into a frilled opaque half apron that I'd
never seen before, with a large bow at the back – then made me make,
serve, and eat dinner – then clean up, with nothing but the panties and
apron underneath my waist. Teasing me of course, she caressed and
patted my backside often, commenting on how pretty I was. We had very
good sex that night – although I found her to be a little more
aggressive than she was normally.
When Edna spanked me the following day, it wasn't sore at all. She did
sting my buttocks with the first slap – which was STILL a lot less
painful than the crop – but then said that if I kicked my feet prettily
and squealed, she would take things easy on me. Later, she and Gloria
both commented on how well I'd emulated a girl being spanked – but
they'd noticed some hair on the backs of my thighs – told me to borrow
a depilatory from Pamela and get rid of all my body hair that night –
except to have my pubic hair formed into a heart shape – and dyed pink!
What could I do? I asked Pamela to help me – and she was ecstatic about
the results! Helped me to apply the depilatory – even shaped and dyed
the hair around my privates! Raved about how wonderful my buttocks felt
under my panties afterwards! Then after we'd almost settled in for the
evening, she started to giggle and, saying she had a great idea, ran
off to the bedroom. When she returned, I almost fainted with desire –
she was dressed in a beautiful set of pink baby dolls and a shortie
peignoir!
"WOW!" I gasped as she sauntered up to me in a sexy provocative
manner.
"You like, sailor?" she said in a fair imitation of Marlene Dietrich.
"Here! Touch me here!"
"You bet doll! Wow! Do you feel nice!" I said.
"You want to feel nice too?" she purred playfully.
"Oh Yeah!" I replied.
A little while later, she had me parading around our bedroom together –
me in my pale blue baby dolls, her in her pink ( The blue looks so
masculine on you darling!" she sniggered).
I'd objected of course, but she persuaded me with a very logical
argument.
"Look! Edna and Gloria are still embarrassing you, right? Dressing you
in girl's clothes! Spanking you on your panties – and when you act like
a little girl? Taking it easy on you!" Her voice was quite scornful.
"They're wanting you to act like a sissy! Making you more girly every
day!"
"But you said . . ," I wailed.
"Oh Tush! They're introducing you to all the girlish things! But what
would it be like if you actually got ahead of them? Then your reaction
will be that much less, won't it?" her voice got firmer, a little
angry.
"Why don't you stop arguing with me! Trust me, I know I'm right! And
anyway? This is also for ME! I want to feel how pretty you feel with
nice clothes on! Now, let's get these baby dolls on you!"
That night she taught me a lot of things I didn't know about pleasing
her – where to stroke her body and face gently – where to caress
firmly. How to use my lips, fingers and tongue to please her – while
she used the same techniques to drive me to distraction. Our lovemaking
– when she allowed it to happen, was spectacular – her being on top as
usual. When we finished, I was lying on my back, while she was propped
up on one elbow, looking down on me with a strange smile on her face.
She fondled some ruffles at my breasts. "My sweet little lesbian lover
– my husband!"
But Pamela was correct. Gloria and Edna continued to feminize me but
as I'd learned to mute my reactions – mostly by becoming more and more
feminine at home, they appeared to get less and less enjoyment from it.
One day, Gloria called me into her office. Edna was there as well.
Both of them were smiling.
"Hi sweetie!" Gloria said. "We've just been talking about you. Finally
decided on your title here."
"I'm not an associate any more?" I asked.
"No. We thought that Office Girl was more appropriate. More in line
with what you've been doing. What do you think?"
I'd been learning to accept what was done to me with equanimity, but
this did shake me. "Office girl?" I mumbled. "But I'm a man."
"Yes, we thought you might say that. Realize that you must get over
that silly mental stumbling block you have. So first thing? We thought
we'd start calling you Carole. Harold is such a masculine name, don't
you think, while Carole is pretty and even sounds a lot like it. On top
of that? Seeing as you're going to be the office girl – and have a name
like Carole? – We're of the opinion that you should get your hair done
properly – in a girl's style of course – and wear nicer clothes. We
won't rush you into that aspect of course – but start wearing a bra
tomorrow, would you? And don't forget – get some nice breast forms to
fit inside it!"
She saw my look of horror. "Just do as you're told dear, and don't you
have some filing to do?"
"Yes Miss Matson.."
" Okay Carole, you can go now. But by the way?"
"Yes Miss?"
"Mrs. Trellis will be coming in shortly. I think you should hide
again, don't you?"
"If Miss Edna doesn't mind?" I said.
"Of course you can hide dear! Sweet of you to ask!" Edna said.
"See? When you don't fuss and act like a girl should? See how
reasonable we are?" Gloria said softly. "Off with you now. I'll call
you when it's time for you to come in."
"Thank you Miss Matson," I said.
She called me in a while later. I was surprised to see that she'd
changed her skirt. Where before it had been a straight sheath in a dark
color to meet her jacket, she was now in a full skirt with the hem well
beneath her knees. She saw me looking. Twirled gracefully. "Like it?"
"It's very pretty Miss Matson," I said.
"Thought you'd like it," she said, giving me a peculiar smile. "Now
into your burrow, bunny Carole. In you go!"
She was talking quite nicely to me now – but her tone was the one you'd
use to a young girl. Blushing, I dropped to my hands and knees and
backed in. She sat down. "Comfy Carole?"
As I replied, "Yes, thank you Miss Matson," she pulled her skirt back
and opened her legs until I was looking directly into her crotch. Okay
Carole, come forward and put your head between my legs and lick me."
"Lick you Miss Matson?" She stretched an arm under the desk and, before
I knew it, she had a hold of my ear! I squealed with pain but moved my
face forward until my nose was practically rubbing against her panties.
Then, she closed her thighs, clamping me in place – then pulled her
long skirt down, over my head so that my head and shoulders were
enclosed in it.
"Now sweetie? Can you hear me alright?" I heard her say.
"Yes Miss Matson, " I said, nodding my head in case she couldn't hear
me.
"Have you ever masturbated Carole?"
I blushed and nodded.
"I just wondered if sissies actually did things like that. So this time
Carole? I'll give you a signal and you can stop licking me, and give me
one of your wonderful 'toe-jobs'" she giggled. But this time? While you
do that, I want you to enjoy yourself too. I want you to caress
yourself until you come into your pretty panties – that way I'll know
you had a good time. Okay?"
"But that will make a mess Miss . ." I never got the chance to finish
as she reached under the desk and rapped my head with her knuckles.
"Just do as you're told!" she snapped – then rang Edna to allow Mrs.
Trellis into the office.
Under her skirt was pungent with a musky scent of a woman in heat and
very warm. She relaxed her thigh muscles which gave me more freedom
of movement, but I knew very well that a retreat was out of the
question – so proceeded to work my tongue. The air under her skirt grew
even more dense and humid as she started to rub herself up against the
bridge of my nose – and then, as her undulations continued, to my
amazement I felt her start to quiver as if an electric shock was
running through her – and her hands stretched down and grabbed my ears
– pulling me into her while the air filled with a strong musky odor and
I knew she had come.
I'm not a hundred percent sure, but there was a definite pause above me
as the older woman seemed to be aware that something sexual was going
on in front of her – but had the sense - or decency – to allow whatever
it was to come to a close. Gloria had signaled she was finished by
widening her thighs to free me, and I pulled back, to start working on
her toes, just as she instructed. I really didn't need any reminding to
then complete what she had ordered. Slowly, luxuriously, I stroked my
erection through my pants as I did so, feeling the satin of my panties
as I slid my erection up and down against them. I felt my eyes close
slowly and came – gushing freely – feeling my whole front become warm
and sticky as I spewed forth.
When I was allowed to come out, Gloria's reasoning became clear. "Look
at that MESS!" she said to Edna. "Can't have Carole walking around
like that." She turned to me. "Have you no sense of office decorum
young lady? I hope you have a change of clothes with you!"
I was well aware that she expected me to say that I was in the mess I
was simply because of what she'd told me. Having no intention of making
more trouble for myself, I simply replied to her question.
"No Miss Matson, I don't have any clothes here. May I go home and
change?"
"No, you may NOT!" Edna said indignantly. "You have work to do here!"
"Didn't that girl – the last office girl leave some clothes in her
locker – Carole's locker now?" Gloria asked. "If she did? I'll bet
there's something that'll fit her in there."
(Somehow? I had the feeling there would be). Later.
"Isn't Carole pretty in her dress? Gloria said semi-seriously as
Edna nodded agreeably. The dress in question was rather new appearing
for a dress that had somehow been left in error – and naturally, it
fitted perfectly – although it was a little large in the bust area. (To
tell the truth, I was surprised that my unknown benefactress hadn't
left me a bra as well). It was a print dress, rather dark background
with orchids. It had a flirty skirt, with a built in slip and puffed
sleeves that Claudia and Edna both swore set off my white weak arms
perfectly.
It fastened in the back and as Edna did the honors, Gloria said, "It'll
probably be too difficult for you to undo those fasteners Carole. Maybe
you can ask Pamela to help you undress when you get home?'
They weren't too happy with how I walked in the dress, despite my best
efforts to imitate the mincing way of walking they were demanding.
Finally, Edna said, "I have an idea that'll speed this up – we don't
have all day to be fooling around teaching this little pansy how to
walk like one. Stand there in front of that chair, Carole!" She went
into the Ladies room and came out with something in her hands. Then she
sat down in the chair and smoothed out her skirt across her lap. "Get
over my knees Carole."
Reluctantly, I laid myself over her knees. "But I haven't done anything
wrong Miss Edna," I said pleadingly.
"Silly girl! I'm not going to spank you!" But as she said this, she
lifted my skirt and gave me a sharp contemptuous slap on my panties.
The quickly slid them down just enough to bare my backside.
"You might want to Relax, Carole," Gloria suggested as I felt Edna's
finger apply some sort of cool gel around and up my backside.
"Oh please – WHAT!" I squealed as something firm and hard was inserted
inside me at the rear! "Oh OH OH!" I whimpered as it was pushed deeper
and deeper inside me. Then, suddenly, the incredible pressure I'd been
feeling disappeared as my backside closed around the alien thing,
accepting it!
"There you go girlie!" Edna said, pulling my panties back into place
and giving me another slap, before adjusting my skirt downwards. "Up
you get!"
I felt as if I had an urgent need to go to the bathroom. Instinctively,
I tightened the muscles around my backside. Stood helplessly. Gloria
gave me a pat on the rear. "It's okay Carole. You have a butt plug in
you – you don't need to go to the bathroom – just walk over to the far
wall and back. Let's see if Edna's idea works."
They were almost in hysterics by the time they finished with me. The
plug did make it nearly impossible to walk in any way but a mincing
fashion, the skirts of my dress literally whipping around as I moved.
But this was not enough for my tormentors – Gloria went out and bought
me some high heeled shoes and thigh high stockings. The shoes were less
of a bother than I would have supposed, but the women had me walk with
my left hand on my hip and my right arm held straight down at a slight
angle to my body, and my hand twisted so that my palm faced forward.
After Edna took her crop out to make SURE that I understood what they
wanted, I learned very quickly.
Then Gloria got the idea that I should help her change back into the
skirt she'd worn originally – and that I should assist her. Edna
suggested that as I was acting in a Ladies maid function? An apron
might be appropriate? Some minutes later, in my dark little dress and a
white apron I was kneeling in front of a woman who at one time had been
my social inferior, undressing her while she reminded me casually of
how I'd once looked down on her – "But you much prefer looking up like
this, don't you Carole?" patting me on the head as one would a pet dog.
As I had learned to do, I smiled up at her subserviently.
"Oh yes Miss Matson."
Early that afternoon, Gloria came to the conclusion that it would be a
good idea for me to notify Pamela that I'd be needing a hairdo as well
as a bra and forms being purchased for me that night. "Give her some
notice you know? Why don't you call her?"
When I did, Pamela's reaction astonished me. "A bra? Breast forms? A
HAIRDO? A WOMAN'S hairdo! Oh, for goodness sake! Have you no pride you
- you simpering little sissy? I mean, you're an Associate in a thriving
law firm, aren't you?"
I wasn't sure if Gloria or Edna were listening in, so had to correct
the impression she was conveying that I'd keep her in ignorance about
my new title. "Actually darling? Gloria thought it would be best if I
got a new title . . ," I paused.
"WELL? Aren't you going to tell me what it is? I don't suppose she's
promoted you to Vice President?" she said, sarcasm dripping from every
word.
She wants me to take the name Carole – and I'm the new office girl!" I
said in a rush.
There was a silence at the other end of the line for a few seconds.
Then Pamela spoke again, in an amused tone. "Ah! I see? You want to
look the part? Of course dear, I understand. But why don't you ask –
nicely now – if you can have the rest of the day off? Suzette, my
hairdresser? She'll be over here today – and she can probably handle
you as well. So go and ask."
"Oh sure Pamela," Gloria's voice broke in on the line. "I was just
listening to make sure Carole didn't forget to ask you properly. She
can be quite forgetful at times. I'll send her home right now. Carole?
Go and tell Miss Edna that I want you to go home! Hurry now – like a
little bunny!"
She HAD been listening in to our conversation after all!
Edna was very nice. "Alright dear. You can go now. No, you can't wear
those nasty yucky clothes you were wearing – that dress is much nicer.
But can I say something?"
"Yes, Miss Edna. Of course," I replied.
"Well? Right now, you look like a man in a dress. With a little work,
you might look a lot more like a girl? Not generate so much notice
while you're getting to your car – or driving home?"
"Will it take long?" I whispered.
"Not at all dear," she said.
She was absolutely correct. Less than ten minutes later she was
escorting me to my car. From somewhere she'd produced a wig, laughingly
stuffed some facial tissues into the front of my dress, than applied
blusher, eyeshadow, eyeliner, mascara, and lipstick. My skirt swishing
about me probably drew more eyes that would otherwise have been
expected – I mean I did look more like a real woman now – but was
certainly not THAT attractive – it was the style of walking that she
demanded from me that drew the stares. The women that saw me looked
scornful – the men, interested. She and I parted – as women do – with
an embrace and a brushing of cheeks.
As I made my way home, I worried. What on earth had got into Pamela?
How would she react to seeing me in a dress, high heels, and makeup?
In our garage, I was surprised to see a brand new Jaguar sitting in her
spot. Wondered who owned it, then let myself into the house embarrassed
by how my heels sounded on the hardwood floors, and ashamed at how I
was walking – even somewhat frightened that I couldn't seem to change
now..
I heard her calling "Who's that?" Then she came around a corner and
gasped, putting her hand to her bosom and looking frightened.
"It's me! Harold!" I said.
"Harold?" Then she gave me a dazzling smile! "I didn't recognize you
darling!" Came and gave me a kiss. "You didn't tell me you would be
wearing a dress!" she said accusingly, but with a smile to soften her
words. Then she backed off. "Actually dear? You look quite good! Did I
ever tell you that I loved you?"
"You certainly didn't sound like it when we spoke on the phone!" I
grumbled.
"Oh! You poor thing! You didn't take me seriously, did you?"
I blinked in surprise. "Yes, Kinda."
She looked quite surprised. "But why? I wasn't sure – thought that one
of them might be listening in! And I was right, wasn't I?"
"I never thought of that," I admitted.
"Oh Carole! You little silly! I love you! You didn't think you're
mummy would be so cruel? Surely not!"
"You just called me Carole!" I protested.
"So? Don't you think you should get used to that name? How do you think
they'll react at the office if you don't answer to it when they speak
to you? I only did that for your own good. Don't you see?"
She was getting a hurt look and my heart went out to her. "I'm sorry
Pamela," I said apologetically. Then, I noticed something. "Those are
really striking earrings – and is that a new ring?"
She beamed a smile at me touching her ear with one finger, then
fluttering her hand. "Aren't they beautiful? The ring is a flawless two
carat diamond – and the matching earrings are one carat each."
"But weren't they dreadfully expensive?" I asked. Then added, "That
Jaguar in the garage?"
"Isn't it a dream? I've always wanted one in that shade of red. They
just delivered it this morning!"
"But didn't these things cost a lot of money?" I asked.
"Maybe – but I have lots, don't I?" she said flippantly. "After all,
what's the use of having money if you can't spend it!"
"But are you talking about the money from our account?" I asked,
worried.
"No. I'm spending the money from MY account. It's mine, isn't it?
And there's still tons of it left!"
I looked at her aghast. Yes, we were rich – but it was money my family
– not hers – had accumulated by conservative means over the generations
– and she seemed to be spending like a drunken sailor! I sighed to
myself. After all, I had signed our money over to her – and what she
had spent so far? It was really a drop in the bucket. My musings were
cut short. She had said something.
"What was that darling?" I asked, "Didn't hear what you said."
"We have a new member in our little family!" she whispered excitedly.
Then spoke loudly. "Bridget! You there?"
A large, swarthy, woman appeared immediately, looking admiringly at
Pamela. "Yes Mistress?" she said.
"Bridget! I'd like you to meet my husband! "
"Your husband ma'am?" the woman said, looking appraisingly at me, her
eyes taking in my hair, makeup – and the dress of course. Then she
came over, with her hand out as if to shake hands. Instinctively I held
mine out – and watched it get engulfed in hers. "Hi!" she said.
"Carole? Bridget is our new housekeeper!" Pamela said. "I think I need
some help around here – so it seemed the most sensible thing to do."
"Pleased to meet you Bridget," I said, my voice small. "But my name is
Harold."
"Carole! Please! I told you why I want you to start accepting your new
name! You'll just confuse Bridget! Say that you're sorry – please?"
Pamela was upset – and it showed.
"Oh! He doesn't have to apologize to me. I want Carole and I to be the
best of friends," Bridget said softly, still holding on to my hand. "I
like your dress Carole. Did you pick it yourself? It looks nice on
you."
She was soft spoken and quite deferential, but she scared the hell out
of me. In my recent experiences with women – even my own WIFE for
goodness sake – I'd discovered a trepidation within myself, a feeling
that I was inadequate beside them. Here, with her holding onto my hand?
I literally felt frozen with fear! At the same time? Should I admit
that I was dressed in the fashion I was because I'd been forced into
it? I mumbled something incoherent.
"Oh Carole!" Pamela said sharply. "Your diction is becoming atrocious!
You must learn to speak UP!"
"I was saying that maybe I should change before Suzette gets here?" I
said, managing a little more clarity.
Pamela gave me an impatient grimace. "Whatever for? Honestly Carole,
you're beginning to THINK like a woman! It's most disconcerting!" She
made a tutting sound.
"Mistress?" Bridget said. "May I suggest that Carole and I have a
little chat? Get to know each other?"
"Yes! Good idea. I'm glad that someone can think straight around here!"
Pamela said, obviously aggravated, and left the room. I became even
more fearful. Bridget had never let go of my hand and was staring quite
hard at me now, a glint of amusement in her eyes.
"Carole? I asked you a question a little while ago, and you never
answered. Now, I consider that a very rude way to treat a servant,
don't you?"
"I'm . .I'm . . terribly . .frightfully . .. sorry Bridget. I got
distracted."
She was taking me over to the sofa, sitting down and pulling me down to
sit in her lap! Finally, let my hand go and put an arm around my
shoulders, then pulling me into her embrace, gently chucked me under
the chin! Smiled possessively at me. "That's all right pet. But you
won't be rude to Bridget again, will you? Ever again?"
"Oh no, Bridget !"
"Know something? You're the prettiest master I've ever had! Do you
like dressing up like a girl? And, like I said? That's a very pretty
dress. And mistress tells me that you're going to get a makeover
tonight!"
I started to try and answer her questions, but she put a large finger
on my lips. "That's all right dearie. I don't mean to be so nosy!
Mistress tells me that you're the office girl for a law firm?"
Horrified, I looked at her. Pamela had told her that? Nodded.
"She's very generous you know! Bought you a LOT of nice clothes for you
to wear to the office."
"I didn't know that," I whispered.
"Well, I thought you didn't, because if you had, you'd never have upset
her now, would you?"
"No."
"Of course you wouldn't have – a nice girl like you! But I understand
that you're rather careless with money?"
"What? What do you mean?"
"Didn't your employer ask mistress to keep an eye on your daily
expenditures? And didn't she say she would?"
"Well, yes . . but you see . ."
"Well mistress has asked me to take that function over. Says that
though she's never had to chastise you, the day could come when you'd
need discipline, and she's too fond of you to administer it."
"Discipline?" I croaked.
"Oh nothing much – a spanking would probably be all that would be
required. That's fair, don't you think?"
Stunned, I could only stare at this huge woman. I was to report to HER!
A servant!
"Oh yes. Very fair!" I stammered.
"Wonderful!" she enthused. "Now, go over my knee," she added, starting
to pull me in that direction.
"But I haven't done anything wrong! Please don't spank me. Please?"
She reached into a pocket and pulled out a latex glove, which she put
on her hand. "I'm not going to spank you – you silly little sissy!" she
said, pulling my panties down. "I'm just going to remove your plug! But
keep in mind, if you don't continue to walk properly? I'll have to
replace it! You won't forget, will you?"
"No." I panted, humiliated beyond words.
"Then every morning before work? You can report to me and I'll insert
it for you. Okay?"
"Mmmm – yes. Oh yes!" I gasped as I felt her withdraw the plug.
"Oh! You and I? We're going to be friends, aren't we? Such intimate
friends!" she whispered, now sticking a finger into me and wiggling
it, then slowly extracting it – then forcing it in again!
Naturally, Pamela chose that particular moment to return – and bring
Suzette, her hairdresser with her! She was in the room before she took
in what was going on.. "Oh Carole! I didn't mean to disturb your fun!
But while we're here, why don't you say hello to Suzette?"
With Bridget's hand on the small of my back, and her finger continuing
to rape me, I could only gape upwards a little, so didn't see much of
Suzette's face, though I knew she had come up and was fingering my
hair.
"Pamela? This will be NO problem at all! I'll be able to shape and fix
it for tonight – no sweat!" Then she giggled, "I'm sorry Harold. I'm
usually better mannered – but business always comes first, right? Nice
to meet you!"
I groaned unintelligibly, but she seemed to take it as an appropriate
answer. Then, chatting amicably, the two women left me under Bridget's
care as if nothing was amiss!
Then, finally, Bridget's finger was out of me. I felt her rearrange the
waist band of my panties, then she was sitting me upright again.
"Wasn't that fun?" she asked rhetorically, a sly expression on her
face. "But now Carole? Walk over to the far wall, and back. I want to
make sure that you haven't forgotten how to walk properly!"
Knowing that she was still holding my plug close by – I remembered all
too well how to walk, and delighted her with my mincing effeminacy as I
sauntered to the wall she'd pointed at – and returned.
Suzette seemed to have a good reputation as both a cosmetician and
hairdresser – and working in conjunction with Pamela had me essentially
feminized before dinner time. It was particularly galling to me to
discover how easily she 'converted' me – especially with her going on
and on about my beautiful complexion, my lack of facial hair and, most
upsetting, my eyelashes – which she raved about. She spent most of the
time until then doing 'odds and sods' as she put it. Hair shampooed,
then trussed up in a turban. Eyebrows waxed (That was painful!) and a
quick manicure and pedicure. Ears pierced.
Pamela decided that it was silly for me to have to cook dinner then
have the clean up etcetera, so we ordered pizza – (of which I got one
tiny slice) and salad – which I was allowed to eat as much as I wanted
– but with minimum dressing, I didn't care for rabbit food – memories
of Gloria referring to me as a 'bunny' still fresh in my mind.
After dinner, I was finally allowed to take my dress off – only to
discover that I was now being fitted with breast forms. To tell the
truth, I'd always thought of them as the old fashioned 'falsies' – you
know, something formed to fit inside a bra? But this was quite
different.
Aghast, I discovered that they were going to be adhered to my body –
and for DAYS at a time! I also found out that, as Suzette
enthusiastically reported, they would feel and act 'just like the real
thing!' So after quite a time taken in measuring me, and making tiny
little indexing marks on my chest, I was introduced to the joys of
semi-permanent breast forms with, naturally, a lacy bra to keep them in
place.
Suzette had wanted me to feel them with my hands and they had felt
surprisingly light.. But once they were affixed? It felt strange – as
if my whole center of gravity had changed – and my new style of walking
seemed to accentuate the strangeness considerably. Another thing that
compounded my strange feeling? Pamela's reaction!
Once my 'breasts' were attached and I was having my hair 'done'? She
grew a little distant from me. Still referred to me as her 'hero' and
'macho husband' – but there was an underlying mockery there that was
becoming more and more evident.. Started telling me how 'gorgeous' I
was now – and how I'd be the 'prettiest office girl' in the whole
building when I returned to work the following day. She produced my new
baby dolls – Pink now – while she wore yellow. She smiled when she saw
me walk – then hung over us as Suzette finally finished with my hair
and applied my make up.
Bridget had disappeared by the time that Suzette started packing all
the tools of her trade – with a tiny application of a very expensive
perfume to my wrists, ears, and bosom. In my high heeled slippers –
pink naturally, and a saucy ribbon in my styled hair – also pink? My
makeup, artfully applied? Glistening nails on both fingers and toes?
My bracelets? I was almost a match for my lovely wife, Pamela. Who
seemed excited for some reason now.
Not by me – obviously. I was now nothing more than a girl companion,
someone to discuss makeup, movies, TV, and magazine articles with.
After a few disapproving glances I learned what responses were 'valid'
and what were not. Accordingly, I spent a leisurely half hour talking
'girl talk' with my wife. During this period, I found out that she had
quite a crush on Jenny – the lawyer who'd been advising us – only she
now referred to her as 'Jen'.
"Oh! Wait until you meet her! So strong! So intelligent! So masculine!
You'll love her, just wait and see!"
Then, the doorbell rang. It was normally my job to answer it but,
dressed as I was – and the fact that Pamela raced to answer it – I
suddenly had the premonition as to who it was going to be. Feminine
intuition? I don't know – but it was Jen.
She (?) Though I'm now used to thinking of her as a 'he' – though
taller than me, was a fairly stocky, muscular woman. Fair hair, bright
blue eyes – a very penetrating stare that she focused on me as she
advanced to be introduced. "You're Carole? Used to be Harold? You're
much prettier than I'd supposed you'd be. Matter of fact! You make a
damn fine looking woman! Come here and give me a kiss."
Meekly, I advanced on her – Pamela walking and smiling alongside me.
"Didn't I SAY that Jen would appeal to you, huh? Isn't she the
greatest?" she said, more than once. And she said to Jen. "Look at how
she's walking. Isn't she CUTE?"
That my wife had referred to me as a 'she' didn't seem to bother me
too much. Jen didn't reply, just stared at me until I minced into her
arms. She took my arms and draped them around her neck and with her
being taller than me, I had to stretch against her. For some reason, I
found this most erotic – especially when she put her hands on my
buttocks to pull me into her. Surprisingly, her kiss was very chaste.
When she disengaged, she smiled at me. 'Nice teeth,' I thought.
"Let's dance?" she said softly. "Pamela? Put on some music, huh?"
I heard Pamela giggle a little. Then the lights dimmed and soft music
surrounded us. Jen felt so strong, and I felt so weak. It seemed
absolutely natural that I played the woman's role. Gradually, I felt my
aversion to femininity disappear – it was if my body were melting into
hers. She was whispering words that were soft and enticing, and I was
nodding my head and making soft mewling noises as she led me over to
sit on a chair.
"I'll be back in a minute. Okay honey?" she whispered. Speechless with
soft lust, I could only nod.
Pamela was taking a hold of my hand and tugging me gently over to sit
beside her at the dressing table bench. I looked at the two women in
the mirror. "My lipstick's all mussed up!" I said, distracted a little
by the fact that one of the women in the mirror was lip syncing what I
was saying.
"Yes! I know! Time to freshen up! Here let me do it for you. Don't want
you all smeared up for Jen, do we?"
"But I thought that Jen was YOUR girlfriend?" I managed to ask trying
valiantly to keep the jealousy out of my voice, when she paused in
making my lips pretty again.
"Oh No! BOYfriend would be more like it – and anyway? Don't you like
her? Isn't she so strong and masculine? I thought you needed to meet
somebody like her. You DO like her! Don't try and pretend to me!"
I saw the girl in the mirror blush. Her lipstick was wet and scarlet
looking now. Saw her lips move again as I answered Pamela. "Yes – I
like her. But it's ME that is masculine . .there's something wrong here
. . ."
She patted my thigh – caressed it actually. "Masculine? Don't be silly!
You may be a male, because of that little thing you have in front of
you – but sweetie? I'M more masculine than you are!"
I opened my mouth to protest, but she over-rode me. "You're sweet,
soft, and girlish. Always were. Now? We're just introducing you to the
joys of being what you should have been all along – a girl! Now stand
up! Lean over this bench, please?"
"What for?" I asked, though I did as she'd said.
"A girl's gotta be ready at all times!" she giggled, lifting up the
back of my baby dolls and pulling down my panties.
"I've been walking properly!" I protested, almost crying as I felt what
she was doing.
"Huh?" she asked, continuing to lubricate my back passage. Then she
laughed. "Oh NO sweetie. It's Bridget's job to put your plugs in and
out now. Just relax." Then, to my surprise, she just pulled my panties
back into position and gave me a tiny slap on the posterior. "That's
it! Remember, just relax!"
I wasn't so stupid that what she was telling me didn't make sense, but
I didn't have any time to react as Jen was back in the room, smiling
dangerously as she came, took me by the hand and led me to the bed. I
didn't make any resistance – couldn't. She lay on one side of me, and
I felt the bed shift, and knew that Pamela was on the other.
Then, in a fog from some forceful necking, I found myself being
positioned into a kneeling position and pulled back until my backside
was hanging over the bed.. Discovered that Pamela was putting a condom
over my erection 'So's you won't mess your nice jammies," she
whispered. I could see the white of her teeth in the darkness as she
smiled.
Within minutes, Jen made me into her woman, entering me from the rear
and whispering pretty words. I still cried but, after a little while of
moving in rhythm with the dildo inside me, felt a pressure growing and,
to my surprise found I was ejaculating into the condom!
"There, there, Carole! Liked that, huh? Now it's time for you to come
and please mummy!"
And, where Pamela had watched me become Jen's woman – Jen now lay
and watched as I became Pamela's lesbian husband!
The following morning it didn't seem so bad, as I laid over Bridget's
knees so that I could have my plug inserted. She used her finger to
tickle me a bit there, but I was sore and asked her, nicely, to stop –
and she smiled understandingly and complied. I didn't quite understand
the clothes I was to wear though.
"Isn't this a maid's uniform?" I asked, fingering the pink, extremely
showy, satin dress with the mass of frilled petticoats – and the
particular lacy panties – also in satin. "I don't know if Miss Matson
or Miss Edna will approve!"
Bridget slid her hand up inside my dress and caressed my backside.
"Don't worry about it sweetheart – just tell them that Bridget dressed
you this morning!"
I left Jen and Pamela necking softly in bed. They both smiled as I
curtseyed (Bridget's 'suggestion') before I left. She (Bridget) then
drove me to work and escorted me to the office, coming in with me.
"Time I met the other ladies in your life Carole," she told me.
Neither Miss Gloria nor Miss Edna seemed put out about my attire – as a
matter of fact, I was surprised to discover that they had a frilled
maid's cap and matching apron that went very well with the dress. I
started feeling uneasy. So many things that didn't make much sense, –
how Pamela was aware of things that went on in the office – and vice
versa. How could Gloria and Edna have had an apron and cap that went
with my dress? How come Bridget knew her way to the office, when she'd
never been there before?
But I wasn't given much time. Had to make coffee and serve it to the
ladies, then Gloria called me into her office – and pointed under the
desk.
"Time for your burrow little bunny. In you go!"
I knew better than to argue – so backed in. She then sat in her chair
and pulled it in enclosing me, and hiking her skirt up and spread her
thighs. Sighed happily as I started to tongue her. Then I heard a
woman's voice – it was familiar, though it took me a few seconds to
realize that it was Dorothy – my old partner.
There was definitely something different about her voice that I
couldn't quite place – and then I realized what it was – she was no
longer speaking in the breathless feminine way she had in the past –
she sounded like a much more mature woman – with lots of confidence.
They spoke for a few minutes, then, to my amazement, Gloria stood up
from her desk and moved away. Then, someone else sat in the chair.
"This the chair that has magical powers?" Dorothy said, hiking her
skirt and slip up to reveal her panties! Then she spread her legs!
I knew what was expected of me now, so moved into her and started
licking and sucking. I could feel her relax – and then she was reaching
under the desk and patting me on the head. "MY! You've finally found
something at which you excel Harold – oh, sorry! Carole! Just keep it
up for a little while, okay? That's a good girl!"
Then, only a few minutes after she'd orgasmed, she was gone – and
someone else was in the chair. But this time? There were no panties
under the skirt – just a large dildo! I knew what I was supposed to do
but there wasn't enough room under that desk – then the chair rolled
back a little and still on my knees I followed it – then just as I
neared it, the chair rolled back some more – and again I neared it and
again it left – and then I was out in the light – and it moved away!
I looked up at Jen smiling at me and she beckoned me with her finger
and, in my pink satin dress, my lacy white apron getting in the way as
I moved along on my knees, my flounced maid's cap bobbing, I followed
her all the way to the center of the office. There, Jen looked down at
me.
"Want to be a good girl, Carole? Give Jen a nice blow job?"
"Yes," I said, near tears, seeing all of the women encircling me.
Pamela, my wife amongst them, smiling proudly and encouragingly.
"Hasn't he turned into the nicest girl?" she boasted as I took the
dildo into my mouth - and with my head bobbing as I moved up and down I
blushed at her praise as all of the women laughed and applauded.
Finally, something was ejaculated into my mouth. I choked, but taken by
surprise as I was, had to swallow!
"Good girl! What a natural!" Pamela said helping me to regain my feet
after Jen removed the dildo. Then, she put her arm around my shoulders
and, turning and making me follow, made a complete turn, making me
face all the women surrounding me.
"Carole? We did this to you today to let you know what you are. Here?
You're the office girl. At home, you're a maid. Here, your desk is that
one over there. At home, you'll have the maid's room adjoining Bridget.
There, you will address her as Miss Bridget, me you'll call Mistress,
and Jen – you will address as Master. Dorothy, Gloria, Jen, and myself
are setting up a new coalition of which you will own nothing . ."
"Though thanks for your money sweetie – we sure needed that!" Dorothy
interrupted.
Pamela smiled. "Very true – but you've been pleasing us four partners
– and as Edna and Bridget are going to be major forces in your life
from here on in and, as it's going to take some time for us to cross
the 'T's' and dot the 'I's' I'd suggest that the three of you go home –
and start becoming friends."
Edna was standing on one side of me, Bridget on the other. As Pamela
finished talking, each of them linked an arm in mine and started
walking me out of the door, with me too dazed to comprehend what I'd
just been told.
"Yeah! Intimate friends!" Bridget said.
"Sounds like a plan to me!" Edna said patting me possessively on the
ass..
"Miss Matson will see you now, Mr. Ellis, but she's asked me to tell
you that she has a busy schedule this morning and will not be able to
spare you much time."
I looked at this perfect example of a modern secretary. Immaculate,
frozen faced, and dressed in a most conservative – but extremely
feminine style. Wanted to put her in her place – SO badly, but knew
that I was in no position to annoy anyone in Gloria Matson's employ, so
smiled as nicely as I could. "Thank you very much," I said humbly. She
looked down her nose at me and flipped her head in a sideways motion to
indicate that I was to go in to Gloria's office. I edged past her into
where Gloria sat making notes on a paper on her desk in front of her.
"Yes? What do you want?" she asked rudely, without even looking up,
before her secretary had enough time to shut the door behind me. I
flushed.
"Gloria? I received your letter this morning. We need to talk. Please?"
She stopped writing and put her pen down. Looked up at me.
"NEED to talk? Harold? Maybe YOU need to talk to me – but I don't see
ME needing to talk to you!"
"Well, some professional courtesy wouldn't be amiss!" I retorted, my
face reddening.
"My goodness! The little bunny has a temper, does he?" she said, openly
sneering.
"Now as I heard Edna tell you, I don't have much time for you. But I
can make some – if you wish?"
Gloria Matson is a high priced attorney with a mind like a steel trap –
absolutely beautiful in a dark Mediterranean way. Always impeccably
dressed, no hair out of place, obviously rich from the custom designed
jewelry she wears – not chunky – but sleek and expensive – like her.
Frankly speaking, she scares and intimidates me normally – and at that
moment, she held my career in her hands – and knew it. Knowing that
retreat was my only viable option, I softened my tone. "That would be
very nice if you could do that Gloria. I'd really appreciate it."
She gave me a predatory smile. "I'll tell you this up front. I'm going
to humiliate you. Really put you down. I've looked forward to doing
something like this to you for a LONG time and I want you to know this
before I start. You understand what I'm saying? Accept this?" I could
see there was no give in her. Nodded.
"Very well. Both of us know why you're here and both of us know that
I'm the one person in this world that can help you. You have been very
naughty Harold so, know what I want you to do for a start?" She paused,
looking at me intently. Pointing at the corner of her office diagonally
across from her desk she told me, "Go over there and stand in the
corner. I'll let you know when you can come out again. Now?" she jerked
her thumb. "GIT!"
I looked at her in amazement. She meant it! Licked my lips. Swallowed.
"You gotta be kidding. Come on Gloria. Stop with this nonsense. Huh?"
A look of unholy glee crossed her face as she saw my weak indecision.
Somehow knew that I would do as she said. Showed her teeth as she bared
her lips. "You weakling! You namby pamby weakling! Go and stand in the
corner! Or leave this office and never come back. NOW!" I had no
choice. Went over to a corner and stood there. "Face INTO the corner!"
she barked. I did.
She actually kept me standing there for almost an hour! An hour in
which she chatted with friends on the telephone, ordered some clothes
the same way – made it very obvious that I was less important to her
than any of these minor chores. Then she called through to her
secretary. "Edna? Do you have a moment please?"
I heard Edna come in to the office. "Yes Miss Matson?" From the way her
voice changed I got the impression she saw me and was enjoying my
discomfiture.
"Grab a chair. Make yourself comfy. Is there any coffee in the
machine?"
"Yes. Would you like me to get you a cup?"
"No. Not yet. Harold?"
I breathed a sigh of relief, my legs were killing me! I turned around.
"Yes Gloria?"
"I did NOT tell you to turn around! Face back into that corner! And
from now on? I'm MISS Matson to you! Understand?"
Shamefaced at allowing myself to be talked to in this manner, I turned
around again. "Yes, Miss Matson." I said meekly. Was sure I heard a
giggle from Edna.
"Very well! Now you can come and stand over here in front of my desk!"
The humiliation was so intense that I felt the tears come into my eyes.
Gloria's keen eyes saw this immediately. "Would you just LOOK at this
pussy, Edna. Crying! Like a goddam woman!"
She pointed to a spot on the floor. "Stand there – and while you're at
it? Clasp your hands in front of you and place them down over your lap.
That's how maids stand when talking to their mistresses. That's how you
will stand when I address you from now on. Good!"
She turned to Edna. "Isn't he just the nicest, softest, marshmallow?
Standing there, just waiting for his mistress to tell him what to do?"
Edna giggled, then Gloria turned her attention back to me. "Tell you
what pussy. Go to the outer office there and get me and Miss Edna a cup
of coffee. You'll find a tray there. Both of us like our coffee black.
Don't dawdle! Off you go!"
I reddened at what I was about to say. "Yes Miss Matson – but is there
a bathroom I can use? Please?"
She smiled gleefully, "Pussy need a wee wee?" I nodded, shame faced.
"Okay – you can use ours. It's a LADIES room. You won't mind using it,
I trust?"
"No, Miss Matson."
"Very well! But if you are going to tinkle in a Ladies? Please sit down
like one. Can I trust you to sit and pee like a good girl?"
"Yes Miss," I said – so desperate that I'd have promised the moon..
She waved her hand in dismissal and I rushed into their private
bathroom – which WAS very feminine in it's set up. Sat down as
requested, and relieved myself. This turned out to be more difficult
than I had anticipated because I had an erection, and it took me some
desperate mental exercises to get it down to where I could pee
satisfactorily.
When I finally came out, I saw the coffee machine and the tray. Set up
the two cups – and saucers and filled them with the aromatic brew that
was in the machine. Took them into the ladies – who regarded my
approach with bright, shining, predatory eyes. Took their coffees from
me with polite 'thank you's', then settled back in their chairs,
waiting for me to return to my servant's stance.
"You were very naughty – stealing all that money from your poor old
clients, weren't you?" Gloria said after taking a sip of her coffee.
I felt my knees almost buckle. "Gloria! You know I wouldn't . . "
"Oh hush, you silly pansy! I know damn well you don't have the smarts
to pull that scam!"
I was thoroughly confused. "Well then, why are you treating me this
way? You have been very mean . ." and to my own outrage, felt the tears
begin to well in my eyes again.
"Dearie? The perception one gets from reading all the documentation is
that you ARE guilty. Your partner – Dorothy? That ditzy blonde that
everyone takes for a lamebrain? It was her. But she's got that audit
trail leading ALL the way back to you – your offshore accounts in the
Cayman
islands – your sweet little partnerships? None of which contain any
money of course. Did you just sign EVERY goddam piece of paper she put
in front of you – you stupid idiot?"
"I trusted her!" I wailed, "But if you KNOW she's the guilty one? Why
are you coming after ME?"
"Because sweetie? You're easy meat, she's not. The way things are? I
can get most of the money from you – but don't have a hope in hell of
getting it from Dorothy unless I get your cooperation. I mean to say,
what jury would ever find someone like her guilty? So listen up. Here's
what is going to happen dearie. I'm buying your share in your
partnership with her. Once I'm in? She'll end up refunding most
everything she's stolen back into the proper places. Then? I'll resell
you your share in the partnership – at a considerable discount of
course, I'll tell you up front."
She smiled at me like a Cheshire cat. Sighed happily and took another
sip of her coffee.
I felt relief surge through me. Okay, my stupidity was going to cost
me, I knew, being fully aware that if money was involved, Gloria was
going to pocket a good percentage of it – but at least my family name
wasn't going to be dragged through the mud. "Okay Gloria. Thanks. I
know I deserve to be. . ."
"MISS MATSON you silly cow!" she snarled loudly, almost spilling her
coffee.
"I'm terribly sorry Miss Matson," I groveled. "I forgot. But may I ask
how long this will take?"
She shrugged, calmer now, "How long? A year – maybe two."
"A YEAR!" I squealed. "But what am I to do in the meantime?"
"Work for me, silly! What do you expect? I'm buying you out – amn't
I?"
"But I'm not a lawyer," I said slowly.
"You're not much of anything!" she said snidely. "But I'll make you my
Associate in the running of the office here."
"That's very kind of you Glo – Miss Matson," I said.
She waved her hand airily, "Don't thank me, sweetie. It's Edna here
you'll be reporting to."
"But doing . . what, exactly?" I asked.
"Whatever she tells you, I'd imagine. I trust her implicitly – and
anything she tells you to do? I want you to see it as word coming
directly from God – namely me." Both women smirked. Gloria sniggered
some more. "Now that I think of it? You DO see me as some sort of
goddess I hope?"
I tried to make light of it. "Of course! How else?"
"Let's see," she said, getting up out of her chair and walking to right
in front of me where she stopped. "Get down on your knees!" she purred.
"Show some respect for your new goddess."
"Please miss Matson. Please don't . . ," I started to say, but she
smiled and put a hand on my shoulders, gently forcing her hand
downwards.. "Down you go! There you are. That's it!" she exulted as I
slowly sank to my knees. "Now? Take my shoes off!" she commanded.
She had very elegant feet and shoes whose glossy perfection and obvious
workmanship indicated a very high price tag. Carefully, I took each of
her silken ankles in turn, lifted them and removed the shoes.
"Now kiss my feet sweetie! Nice big sucky kisses! Take my toes into
your mouth and suck on them real good! I'll enjoy it more if you
slobber a little bit."
She made me perform this subservient act while she stood – and had a
conversation with Edna about some movie she'd seen a few nights before.
Then, she finally patted me on the head as if I were a pet.
"That was very nice sweetheart. Did you enjoy that?"
"Yes Miss," I mumbled.
"But isn't Edna your new boss? Don't want to disrespect her, do you?"
"No ma'am"
"Very good! So why don't you crawl over to her and do the same thing,
huh?"
I did start to cry as I crawled over the office floor and performed the
same act for Edna, the only difference being that she was not quite as
elegantly shod – remaining seated, and constantly wiggling her toes
inside my mouth and sighing with pleasure as I attended to her. To
humiliate me further, Gloria came and sat beside her – and put her feet
up on my back as if I was a footstool!
Finally, I was allowed to leave the office after signing some papers –
which Gloria refused to let me read. "Just sign those sweetie. Please
don't try to read them – they'll just confuse your pretty head! And
when you get here tomorrow – eight o'clock SHARP! Report to Edna.
She'll tell you what to do."
Emotionally exhausted I arrived home about an hour later. Pamela, my
lovely sweet wife, was there to greet me. Looked at me and gave me a
lovely, sympathetic hug. "Oh dear! You've been crying. Was it that
bad? Here, come sit beside mummy and tell her all about it."
"It was awful! Really awful! The way Gloria and Edna humiliated me!" I
started and, as she pulled my head into her shoulder, started to weep
copiously.
"What did she do?" she asked dabbing at my eyes with a dainty,
perfumed, handkerchief after my crying had abated.
I didn't tell her everything of course – I mean, a man has his pride
don't you think? I also may have exaggerated my own responses as well,
but all in all, Pamela was suitably impressed by my revised version of
the actual events. "Oh, you wonderfully brave man! To suffer such
indignities for me! No, NO! I cannot let you go on with this! We'll
tell her to do her worst! Tell her to go to HELL!"
I was SO encouraged by my wife's reaction. Felt it to be somewhat on
the melodramatic side, but was strengthened by it. "No dear!" I said
bravely. "It is a sacrifice I'm making, but with you by my side? I can
make it – and do so willingly!"
She shook her head admiringly. "My MAN!" she said. "You may be small
in stature – but you're a GIANT in my eyes!"
Then she smiled tentatively. "But dear? If you're going to go through
with this? We'll have to do what Jenny suggested, don't you think? I
feel just awful asking it of you. But she's been very accurate in
forecasting what Gloria would do so far."
"Damn lawyers! They're all monsters! Takes one to know one!" I growled.
"Yes dear – but Jenny's my friend – she wouldn't steer us wrong. If
you sign the house and bank accounts over to me? Gloria won't have a
chance of laying her sticky hands on them – and that way, when this is
all over? We can simply reverse the process." A hurt look came into her
eyes. "Of course – if you don't trust me?"
I felt a rush of shame for my attitude towards my loving wife. "Oh
darling! Of course I trust you! Did you get all the paperwork from
Jenny?"
"Yes dear. They're over on the table, but are you REALLY sure you want
to go through with this?" She looked at me coyly, her beautiful eyes
shining.
"Of course, my darling!" I said happily.
I had just finished signing a mess of documents, with Pamela taking up
each one into her hands as I signed it. "Well!" I said, clapping my
hands.
"That's that! Gloria will probably be mad – but ask me if I care!"
"My HERO!" she then said, taking me into her arms and kissing me. Not
for the first time, I was surprised by the strength in her arms. Then
she disengaged her lips from mine. "Oh I forgot! She called when you
were on your way home. Said she'd forgotten to talk salary with you."
"Guess I can discuss it with her tomorrow," I said, shrugging.
"No need darling. She discussed it with me. Actually? Considering that
what you're going to be doing – a sort of assistant to her secretary?
I thought her offer most generous, and accepted it for you. She's going
to make out your paychecks to me – putting them directly into my
account."
"I don't understand that." I said, a little put out with the idea of
her discussing my salary with Gloria.
"What's to understand?" she asked.
"I didn't know you had a separate bank account," I said.
"Well – it WAS our joint account," she said "But didn't you just sign
it over to me?"
"I see. I'm sorry, just didn't think. How much is she going to pay
me?"
"More than enough my dear. And don't worry. I'll make sure that you
get enough pocket money." Then she paused. "But something else about
money I'm afraid? Please don't be angry with me darling?" She was
using her little girl voice now, one that always won me over.
"I never could be angry with you sweetheart!" I assured her.
"Well? Gloria said that I've to take your credit cards away . . and .
. you've got to tell me every cent you spend in a day."
"WHAT!" I yelled.
"Well sweetheart? She thinks that you're silly with money – and now
that you're working for her? She just wants me to keep an eye on you is
all. I mean it sounds reasonable – don't you think?"
"I guess so . . I guess." I stammered, seeing everything that amounted
to my independence being removed, item by item.
"Very good then!" she smiled widely. "Now, would you go and pour us
both drinks? We can drink a toast to our new arrangement!"
"Okay dear . . but won't you even give me a hint about how much I'm to
be paid?"
Her smile dimmed. "Drinks please, pet!"
I could see that she was getting a little aggravated, so took off and
poured the drinks. Then she said she was a mite puckish, so I put a
little tray of munchies together for her, then started making dinner.
We chatted quite a long time, then I was stupid and asked her about my
salary again. Her eyes got cold. "Don't you trust me darling?
Frightened I'll steal your money from you?"
"Oh no! It's not that at all! It's just . ."
"Don't you have dishes to do dear?" she said this with a considerable
amount of ice in her tone.
Later on, she wandered into the kitchen when I was just about finished.
She was nice enough to put some dishes away though she was somewhat
distant in her manner. But after I apologized for bugging her about
my wages, she returned to her normal sweet demeanor. "Wonderful! Thank
you dear. We don't need to mention this distasteful subject again, do
we?"
"Not if you don't want to darling." I said, grateful to see myself back
in my wife's good books. Was even more grateful when she took me in her
arms again and kissed me.
The following morning I had to wait outside Gloria's office door until
Edna appeared. She opened the door, and ushered me in. Good morning
Harold," she said, pleasantly enough. "You can go and put a pot of
coffee on. Miss Matson likes that special mix in the cupboard there –
put six heaped measures and make a full pot. But here, before you
start? I have a little present for you to wear while your doing chores
here," and she pulled out a frilly, dainty little half apron of some
filmy material. "Here. get this on. After you've made the coffee, I
want you to dust and vacuum Miss Matson's office – so look sharp!"
"I don't really need that apron though, do I?" I replied.
She just stared at me for a second without replying, then handed it to
me. "Put a nice bow in the back. Think you can do that?"
"Yes," I whispered.
It took me some time to get over wearing such a feminine garment but I
had made coffee and dusted Miss Matson's office by the time she came
in. I was just beginning to vacuum when she entered. "Very good. That
apron looks nice on you. But you can vacuum later. I'm expecting a
client shortly. So put your vacuum away and go and get my coffee."
"Yes Miss Matson," I said and was just about to leave her office when I
heard Edna's voice on the intercom. Gloria? You have a Mrs. Trellis
here to see you. You ready for her?"
Gloria was obviously about to say yes, but stopped when she saw my
expression. "Something wrong?" she asked. "She's a good friend of
Pamela's" I said "and please, I don't want her to see me like this?
Can I take the apron off?"
"Yes – but only if Edna okays it."
"But Edna's out there with Mrs. Trellis. Please let me take it off?"
"No! Find yourself somewhere to hide if it bothers you that much!" She
snapped.
I looked around the office. Okay, I'm very small, but there was
nowhere that I could use. "But there's nowhere . ." I started. She
pursed her lips impatiently and beckoned me around to her side of the
desk, then rolled her chair back to reveal the depth of the well. Go in
there!" she said. Lots of room for a tiny thing like you! Just think of
yourself as a bunny in her burrow. In you go now – quick!"
Seconds later, she was telling Edna to let Mrs. Trellis in, as I
crouched under her desk on my knees.
Gloria did get up to greet her client, but then came back and sat down.
As she did, she hiked her skirt up to reveal a gorgeous black satin
slip, with ultra delicate lace around the hem. Then, after they had
discussed what was going on, she asked Mrs. Trellis to define what she
saw as the problem in her own words.
Mrs. Trellis being a real chatterbox was only too happy and started in
talking. As soon as she did so, Gloria kicked off one of her shoes –
and started probing at my face with it. What she wanted was immediately
clear. Obediently, I took her toes into my mouth and started to lick
and suck them through her nylons. To my amazement and chagrin, her
right hand dropped under the desk, and hiked up her dress and slip to
reveal matching black panties. Slowly, she began to finger herself.
Right in front of me!
When Mrs. Trellis gave signs of slowing down, Gloria let out a small
sigh of contentment before getting back down to work again. Altogether
I was under her desk for over twenty minutes and, once I heard Mrs.
Trellis leave I slowly uncorked myself from my hiding space – legs
cramping - and immediately found myself in an entirely different form
of trouble – Edna!
Her face was a little blotchy and her breathing a little fast and, to
my dismay, she was holding a riding crop in one hand – smacking it into
the palm of the other – a most disconcerting sight to see. "Where WERE
you!" The words formed a question, but it was a statement more than a
question.
"I was hiding from Mrs. Trellis. She's a friend of ours and . . ."
"Did you ASK for my permission to hide?" she snapped.
I felt my knees start to shake. "No Miss Edna. I didn't have time –
and I got permission from Miss Gloria. It was her that suggested it!"
"But you know that you report directly to me?" she was now speaking in
a silky smooth voice.
"Yes Miss Edna."
"Okay? Just to remind you for next time? Drop your pants and bend
over!"
I paused in obeying her, just enough to infuriate her all the more. "If
you don't hurry up?" she hissed, "I'll give you SUCH a hiding!" With
that, she swished the crop venomously through the air! Terrified, I
undid my belt buckle and the fasteners that held my pants.
"Let them fall! And bend over!"
As I obeyed her, from the corner of my eye I saw Gloria return from the
Ladies room. "What's all this then?" she asked at the same time as the
crop whistled through the air and seared my buttocks.
I had not anticipated such a pain. Let out a shriek and jumped about
six inches straight up into the air! Scared both women for a second,
then they started laughing so hard because when I landed, I had a
problem keeping my balance and with my pants down about my ankles was
hopping about the office like an offended kangaroo, rubbing my
posterior and weeping with the pain.
"Oh dear Oh dear!" Gloria was hiccupping, "Thank god I just had a pee!
But why are you punishing him Edna? He just gave me a dreamy toesuck!
Wonderful!"
"He hadn't told me he was going to hide, and anyway? I just felt like
giving him a whipping!" Edna said, the color mounting on her face
again. She whistled the crop through the air again. "C'mere you damn
pansy! I want to give you another couple!"
I wept and pleaded but she just pointed to a spot in front of her. "I'm
not coming to you, dearie! Better get your ass over here! I was just
gonna give you two more. Now? It's three. Keep fooling around, and I'm
gonna raise the count some more!"
They both giggled as I shuffled and hopped to where she pointed,
because she wouldn't let me pull my pants up. Then I was in front of
her, my backside in the air – weeping still and pleading, when Gloria –
of all people – saved me! "Edna? That's a pretty good welt you've
raised on his buttocks. Very unsightly, don't you think?"
"Can't make an omelet without breaking eggs, huh?" Edna replied, then
started to take her stance again.
"It must be very painful – that crop really whistles Edna. Harold?
Does it hurt?"
"Oh YES! Miss Matson, it really DOES!" I whimpered.
I saw her nodding sagely. "Yes, I thought so. Tell me sweetie, would
you rather be hit with the crop or put over her knee and spanked?" she
asked me.
"A spanking! Oh YES!" I answered promptly.
"Aw Gloria! That sounds okay – but I think he's more humiliated this
way!" Edna grumbled.
"Well, maybe we could even it up a little?" Gloria commented. "Harold?
Suppose I told you that if you come in tomorrow, dressed as you are,
you'd get your punishment with the crop?" She paused for a second as if
waiting for an answer. Then, getting none from me. "Or? If you were
wearing nice, satiny, panties – you'd get a spanking instead? Just by
hand?"
"They'd have to be PINK!" Edna stated firmly.
"I think we should leave it up to Harold," Gloria said. "See Harold?
Wear nice panties – pink panties, you simply get a spanking. Don't?
Edna practices her crop technique on you. That simple. Your choice.
That okay by you Edna?"
"I guess!" Edna said grudgingly.
I looked at it this way. I could argue the point – and get whipped by
the crop. Or? Just tell them I'd wear panties tomorrow – give myself
time to think? If she whipped me tomorrow because I wasn't wearing
panties? I'd be no worse off, would I? Eager to defer the punishment
any way I could, I nodded, eagerly.
Edna kept me busy filing and cleaning out the Ladies room and didn't
punish me any more. But by the time the end of the day came, I'd
reconsidered. Hey, I'd told them I'd wear panties – and god knows what
Edna would do to me if I didn't. And who was to know anyway - other
than her and Gloria? Sure, it might be difficult to sneak them past
Pamela – but I did the laundry anyway, so I could probably get away
with it. I wasn't too keen on the idea of buying panties – but I could
always tell the salesgirl that they were for my wife, huh? No problem.
I don't know what possessed me to look in my wallet at quitting time.
I nearly fainted! There was about two dollars there – and my credit
cards were all gone! Pamela must have taken them without telling me!
My delectable wife greeted me with a big hug. "Hi sweetie! I've been
waiting and waiting for you to tell me all about your day! Why don't
you pour us drinks, then you can tell me all about it before you make
dinner."
"Pamela darling? You didn't leave me very much money – and you took
my credit cards. May I have some money?"
"Certainly darling! But what do you need money for? And how much?"
I had absolutely no idea of what panties cost – and it suddenly dawned
on me that I'd no idea where to buy satin panties either!
"I lost a bet," I said, grabbing for the only explanation I could think
of.
"Who do you owe the money to?" she said, knitting her brows with
disapproval. "I can see why Gloria had this idea to control your fiscal
activities! Harold? That is disgraceful behavior!"
"Edna." I quavered – everything was going wrong!
"Well, I shall have a nice long chat with Edna tomorrow! Taking
advantage of her position like that!"
I felt my face begin to crumple, felt tears well in my eyes. "Please
Pamela. Please?"
"No! Harold? I'm not being mean! This is for your own good!" She
suddenly looked at me shrewdly."I have the feeling that you're telling
mummy big fibs. Am I right?"
"Yes Pamela," I mumbled, and the humiliations of the day overcame me
again, and I started to cry.
"Well, come and tell me all about it," she said kindly then took me
over to the sofa. Like the previous evening she embraced me and patted
my eyes with her perfumed handkerchief – but this time, it finally
dawned on me that I was sitting on her lap! Telling her all about my
day – this time a little more honestly.
Her response surprised me. Yes, she was as supporting as ever – but
where I'd expected nothing but scorn from her with regard to the
panties, she was as pragmatic as could be. "I don't know why you're
making so much fuss about wearing panties," was the first thing she
said. "You are simply playing into their hands by reacting this way!"
"I don't understand Pamela. What do you mean?"
"Harold! You knew yesterday that Gloria was going to humiliate you. She
told you that for goodness sake! Right?" I couldn't remember telling
Pamela this, but nodded in agreement. "So now they spank you – and you
act all humiliated – and tell you to wear panties – and you act
humiliated all over again! They're just acting like bullies the world
over. Do something - and get a reaction from you, so think that it was
fun – let's do it some more! And you're humiliated! Just a vicious
circle!"
"But what are you suggesting? That I act like I'm NOT humiliated?"
"EXACTLY! Wear the panties – but not just tomorrow – EVERY day! I've
got lots of pretty ones and can give you all that you need. Let's go
and look you out some right now!"
"You mean that by doing that, they'll stop?"
"Oh, they'll think up something else, I'm sure – but if you still want
to keep the promises you made last night and put up with it? All you
have to do is go along with what they tell you to do – but don't let
out a single PEEP about how embarrassed or humiliated you feel!
Understand?"
It made sense, in a convoluted sort of way – but I was so relieved to
have escaped the scorn I'd thought I'd get from Pamela that I accepted
her ideas enthusiastically. She went to our bedroom while I made the
drinks. When I got there with them, she had about a dozen pair of
panties laid out on the bed. Happy and smiling, she kept pressing one
pair after another into my hands making me say how nice they felt – and
admire the lace, etc. Actually? They did feel very nice to the touch.
"You're blushing!" she accused me.
"Well? It IS kinda embarrassing, you know!" I replied.
"Can't have you acting like this at work tomorrow! Let's get you used
to them!" she said. "Get your shoes, socks, and pants off. Let's see.
Those pink ones are lovely – and just a little shade pinker than that
other pair – these you can wear tomorrow. Okay sweetie! Panty time!"
It was bad enough wearing the panties, but my embarrassment was made
worst a hundredfold and she compounded that by not letting me put my
other clothes on, tying me into a frilled opaque half apron that I'd
never seen before, with a large bow at the back – then made me make,
serve, and eat dinner – then clean up, with nothing but the panties and
apron underneath my waist. Teasing me of course, she caressed and
patted my backside often, commenting on how pretty I was. We had very
good sex that night – although I found her to be a little more
aggressive than she was normally.
When Edna spanked me the following day, it wasn't sore at all. She did
sting my buttocks with the first slap – which was STILL a lot less
painful than the crop – but then said that if I kicked my feet prettily
and squealed, she would take things easy on me. Later, she and Gloria
both commented on how well I'd emulated a girl being spanked – but
they'd noticed some hair on the backs of my thighs – told me to borrow
a depilatory from Pamela and get rid of all my body hair that night –
except to have my pubic hair formed into a heart shape – and dyed pink!
What could I do? I asked Pamela to help me – and she was ecstatic about
the results! Helped me to apply the depilatory – even shaped and dyed
the hair around my privates! Raved about how wonderful my buttocks felt
under my panties afterwards! Then after we'd almost settled in for the
evening, she started to giggle and, saying she had a great idea, ran
off to the bedroom. When she returned, I almost fainted with desire –
she was dressed in a beautiful set of pink baby dolls and a shortie
peignoir!
"WOW!" I gasped as she sauntered up to me in a sexy provocative
manner.
"You like, sailor?" she said in a fair imitation of Marlene Dietrich.
"Here! Touch me here!"
"You bet doll! Wow! Do you feel nice!" I said.
"You want to feel nice too?" she purred playfully.
"Oh Yeah!" I replied.
A little while later, she had me parading around our bedroom together –
me in my pale blue baby dolls, her in her pink ( The blue looks so
masculine on you darling!" she sniggered).
I'd objected of course, but she persuaded me with a very logical
argument.
"Look! Edna and Gloria are still embarrassing you, right? Dressing you
in girl's clothes! Spanking you on your panties – and when you act like
a little girl? Taking it easy on you!" Her voice was quite scornful.
"They're wanting you to act like a sissy! Making you more girly every
day!"
"But you said . . ," I wailed.
"Oh Tush! They're introducing you to all the girlish things! But what
would it be like if you actually got ahead of them? Then your reaction
will be that much less, won't it?" her voice got firmer, a little
angry.
"Why don't you stop arguing with me! Trust me, I know I'm right! And
anyway? This is also for ME! I want to feel how pretty you feel with
nice clothes on! Now, let's get these baby dolls on you!"
That night she taught me a lot of things I didn't know about pleasing
her – where to stroke her body and face gently – where to caress
firmly. How to use my lips, fingers and tongue to please her – while
she used the same techniques to drive me to distraction. Our lovemaking
– when she allowed it to happen, was spectacular – her being on top as
usual. When we finished, I was lying on my back, while she was propped
up on one elbow, looking down on me with a strange smile on her face.
She fondled some ruffles at my breasts. "My sweet little lesbian lover
– my husband!"
But Pamela was correct. Gloria and Edna continued to feminize me but
as I'd learned to mute my reactions – mostly by becoming more and more
feminine at home, they appeared to get less and less enjoyment from it.
One day, Gloria called me into her office. Edna was there as well.
Both of them were smiling.
"Hi sweetie!" Gloria said. "We've just been talking about you. Finally
decided on your title here."
"I'm not an associate any more?" I asked.
"No. We thought that Office Girl was more appropriate. More in line
with what you've been doing. What do you think?"
I'd been learning to accept what was done to me with equanimity, but
this did shake me. "Office girl?" I mumbled. "But I'm a man."
"Yes, we thought you might say that. Realize that you must get over
that silly mental stumbling block you have. So first thing? We thought
we'd start calling you Carole. Harold is such a masculine name, don't
you think, while Carole is pretty and even sounds a lot like it. On top
of that? Seeing as you're going to be the office girl – and have a name
like Carole? – We're of the opinion that you should get your hair done
properly – in a girl's style of course – and wear nicer clothes. We
won't rush you into that aspect of course – but start wearing a bra
tomorrow, would you? And don't forget – get some nice breast forms to
fit inside it!"
She saw my look of horror. "Just do as you're told dear, and don't you
have some filing to do?"
"Yes Miss Matson.."
" Okay Carole, you can go now. But by the way?"
"Yes Miss?"
"Mrs. Trellis will be coming in shortly. I think you should hide
again, don't you?"
"If Miss Edna doesn't mind?" I said.
"Of course you can hide dear! Sweet of you to ask!" Edna said.
"See? When you don't fuss and act like a girl should? See how
reasonable we are?" Gloria said softly. "Off with you now. I'll call
you when it's time for you to come in."
"Thank you Miss Matson," I said.
She called me in a while later. I was surprised to see that she'd
changed her skirt. Where before it had been a straight sheath in a dark
color to meet her jacket, she was now in a full skirt with the hem well
beneath her knees. She saw me looking. Twirled gracefully. "Like it?"
"It's very pretty Miss Matson," I said.
"Thought you'd like it," she said, giving me a peculiar smile. "Now
into your burrow, bunny Carole. In you go!"
She was talking quite nicely to me now – but her tone was the one you'd
use to a young girl. Blushing, I dropped to my hands and knees and
backed in. She sat down. "Comfy Carole?"
As I replied, "Yes, thank you Miss Matson," she pulled her skirt back
and opened her legs until I was looking directly into her crotch. Okay
Carole, come forward and put your head between my legs and lick me."
"Lick you Miss Matson?" She stretched an arm under the desk and, before
I knew it, she had a hold of my ear! I squealed with pain but moved my
face forward until my nose was practically rubbing against her panties.
Then, she closed her thighs, clamping me in place – then pulled her
long skirt down, over my head so that my head and shoulders were
enclosed in it.
"Now sweetie? Can you hear me alright?" I heard her say.
"Yes Miss Matson, " I said, nodding my head in case she couldn't hear
me.
"Have you ever masturbated Carole?"
I blushed and nodded.
"I just wondered if sissies actually did things like that. So this time
Carole? I'll give you a signal and you can stop licking me, and give me
one of your wonderful 'toe-jobs'" she giggled. But this time? While you
do that, I want you to enjoy yourself too. I want you to caress
yourself until you come into your pretty panties – that way I'll know
you had a good time. Okay?"
"But that will make a mess Miss . ." I never got the chance to finish
as she reached under the desk and rapped my head with her knuckles.
"Just do as you're told!" she snapped – then rang Edna to allow Mrs.
Trellis into the office.
Under her skirt was pungent with a musky scent of a woman in heat and
very warm. She relaxed her thigh muscles which gave me more freedom
of movement, but I knew very well that a retreat was out of the
question – so proceeded to work my tongue. The air under her skirt grew
even more dense and humid as she started to rub herself up against the
bridge of my nose – and then, as her undulations continued, to my
amazement I felt her start to quiver as if an electric shock was
running through her – and her hands stretched down and grabbed my ears
– pulling me into her while the air filled with a strong musky odor and
I knew she had come.
I'm not a hundred percent sure, but there was a definite pause above me
as the older woman seemed to be aware that something sexual was going
on in front of her – but had the sense - or decency – to allow whatever
it was to come to a close. Gloria had signaled she was finished by
widening her thighs to free me, and I pulled back, to start working on
her toes, just as she instructed. I really didn't need any reminding to
then complete what she had ordered. Slowly, luxuriously, I stroked my
erection through my pants as I did so, feeling the satin of my panties
as I slid my erection up and down against them. I felt my eyes close
slowly and came – gushing freely – feeling my whole front become warm
and sticky as I spewed forth.
When I was allowed to come out, Gloria's reasoning became clear. "Look
at that MESS!" she said to Edna. "Can't have Carole walking around
like that." She turned to me. "Have you no sense of office decorum
young lady? I hope you have a change of clothes with you!"
I was well aware that she expected me to say that I was in the mess I
was simply because of what she'd told me. Having no intention of making
more trouble for myself, I simply replied to her question.
"No Miss Matson, I don't have any clothes here. May I go home and
change?"
"No, you may NOT!" Edna said indignantly. "You have work to do here!"
"Didn't that girl – the last office girl leave some clothes in her
locker – Carole's locker now?" Gloria asked. "If she did? I'll bet
there's something that'll fit her in there."
(Somehow? I had the feeling there would be). Later.
"Isn't Carole pretty in her dress? Gloria said semi-seriously as
Edna nodded agreeably. The dress in question was rather new appearing
for a dress that had somehow been left in error – and naturally, it
fitted perfectly – although it was a little large in the bust area. (To
tell the truth, I was surprised that my unknown benefactress hadn't
left me a bra as well). It was a print dress, rather dark background
with orchids. It had a flirty skirt, with a built in slip and puffed
sleeves that Claudia and Edna both swore set off my white weak arms
perfectly.
It fastened in the back and as Edna did the honors, Gloria said, "It'll
probably be too difficult for you to undo those fasteners Carole. Maybe
you can ask Pamela to help you undress when you get home?'
They weren't too happy with how I walked in the dress, despite my best
efforts to imitate the mincing way of walking they were demanding.
Finally, Edna said, "I have an idea that'll speed this up – we don't
have all day to be fooling around teaching this little pansy how to
walk like one. Stand there in front of that chair, Carole!" She went
into the Ladies room and came out with something in her hands. Then she
sat down in the chair and smoothed out her skirt across her lap. "Get
over my knees Carole."
Reluctantly, I laid myself over her knees. "But I haven't done anything
wrong Miss Edna," I said pleadingly.
"Silly girl! I'm not going to spank you!" But as she said this, she
lifted my skirt and gave me a sharp contemptuous slap on my panties.
The quickly slid them down just enough to bare my backside.
"You might want to Relax, Carole," Gloria suggested as I felt Edna's
finger apply some sort of cool gel around and up my backside.
"Oh please – WHAT!" I squealed as something firm and hard was inserted
inside me at the rear! "Oh OH OH!" I whimpered as it was pushed deeper
and deeper inside me. Then, suddenly, the incredible pressure I'd been
feeling disappeared as my backside closed around the alien thing,
accepting it!
"There you go girlie!" Edna said, pulling my panties back into place
and giving me another slap, before adjusting my skirt downwards. "Up
you get!"
I felt as if I had an urgent need to go to the bathroom. Instinctively,
I tightened the muscles around my backside. Stood helplessly. Gloria
gave me a pat on the rear. "It's okay Carole. You have a butt plug in
you – you don't need to go to the bathroom – just walk over to the far
wall and back. Let's see if Edna's idea works."
They were almost in hysterics by the time they finished with me. The
plug did make it nearly impossible to walk in any way but a mincing
fashion, the skirts of my dress literally whipping around as I moved.
But this was not enough for my tormentors – Gloria went out and bought
me some high heeled shoes and thigh high stockings. The shoes were less
of a bother than I would have supposed, but the women had me walk with
my left hand on my hip and my right arm held straight down at a slight
angle to my body, and my hand twisted so that my palm faced forward.
After Edna took her crop out to make SURE that I understood what they
wanted, I learned very quickly.
Then Gloria got the idea that I should help her change back into the
skirt she'd worn originally – and that I should assist her. Edna
suggested that as I was acting in a Ladies maid function? An apron
might be appropriate? Some minutes later, in my dark little dress and a
white apron I was kneeling in front of a woman who at one time had been
my social inferior, undressing her while she reminded me casually of
how I'd once looked down on her – "But you much prefer looking up like
this, don't you Carole?" patting me on the head as one would a pet dog.
As I had learned to do, I smiled up at her subserviently.
"Oh yes Miss Matson."
Early that afternoon, Gloria came to the conclusion that it would be a
good idea for me to notify Pamela that I'd be needing a hairdo as well
as a bra and forms being purchased for me that night. "Give her some
notice you know? Why don't you call her?"
When I did, Pamela's reaction astonished me. "A bra? Breast forms? A
HAIRDO? A WOMAN'S hairdo! Oh, for goodness sake! Have you no pride you
- you simpering little sissy? I mean, you're an Associate in a thriving
law firm, aren't you?"
I wasn't sure if Gloria or Edna were listening in, so had to correct
the impression she was conveying that I'd keep her in ignorance about
my new title. "Actually darling? Gloria thought it would be best if I
got a new title . . ," I paused.
"WELL? Aren't you going to tell me what it is? I don't suppose she's
promoted you to Vice President?" she said, sarcasm dripping from every
word.
She wants me to take the name Carole – and I'm the new office girl!" I
said in a rush.
There was a silence at the other end of the line for a few seconds.
Then Pamela spoke again, in an amused tone. "Ah! I see? You want to
look the part? Of course dear, I understand. But why don't you ask –
nicely now – if you can have the rest of the day off? Suzette, my
hairdresser? She'll be over here today – and she can probably handle
you as well. So go and ask."
"Oh sure Pamela," Gloria's voice broke in on the line. "I was just
listening to make sure Carole didn't forget to ask you properly. She
can be quite forgetful at times. I'll send her home right now. Carole?
Go and tell Miss Edna that I want you to go home! Hurry now – like a
little bunny!"
She HAD been listening in to our conversation after all!
Edna was very nice. "Alright dear. You can go now. No, you can't wear
those nasty yucky clothes you were wearing – that dress is much nicer.
But can I say something?"
"Yes, Miss Edna. Of course," I replied.
"Well? Right now, you look like a man in a dress. With a little work,
you might look a lot more like a girl? Not generate so much notice
while you're getting to your car – or driving home?"
"Will it take long?" I whispered.
"Not at all dear," she said.
She was absolutely correct. Less than ten minutes later she was
escorting me to my car. From somewhere she'd produced a wig, laughingly
stuffed some facial tissues into the front of my dress, than applied
blusher, eyeshadow, eyeliner, mascara, and lipstick. My skirt swishing
about me probably drew more eyes that would otherwise have been
expected – I mean I did look more like a real woman now – but was
certainly not THAT attractive – it was the style of walking that she
demanded from me that drew the stares. The women that saw me looked
scornful – the men, interested. She and I parted – as women do – with
an embrace and a brushing of cheeks.
As I made my way home, I worried. What on earth had got into Pamela?
How would she react to seeing me in a dress, high heels, and makeup?
In our garage, I was surprised to see a brand new Jaguar sitting in her
spot. Wondered who owned it, then let myself into the house embarrassed
by how my heels sounded on the hardwood floors, and ashamed at how I
was walking – even somewhat frightened that I couldn't seem to change
now..
I heard her calling "Who's that?" Then she came around a corner and
gasped, putting her hand to her bosom and looking frightened.
"It's me! Harold!" I said.
"Harold?" Then she gave me a dazzling smile! "I didn't recognize you
darling!" Came and gave me a kiss. "You didn't tell me you would be
wearing a dress!" she said accusingly, but with a smile to soften her
words. Then she backed off. "Actually dear? You look quite good! Did I
ever tell you that I loved you?"
"You certainly didn't sound like it when we spoke on the phone!" I
grumbled.
"Oh! You poor thing! You didn't take me seriously, did you?"
I blinked in surprise. "Yes, Kinda."
She looked quite surprised. "But why? I wasn't sure – thought that one
of them might be listening in! And I was right, wasn't I?"
"I never thought of that," I admitted.
"Oh Carole! You little silly! I love you! You didn't think you're
mummy would be so cruel? Surely not!"
"You just called me Carole!" I protested.
"So? Don't you think you should get used to that name? How do you think
they'll react at the office if you don't answer to it when they speak
to you? I only did that for your own good. Don't you see?"
She was getting a hurt look and my heart went out to her. "I'm sorry
Pamela," I said apologetically. Then, I noticed something. "Those are
really striking earrings – and is that a new ring?"
She beamed a smile at me touching her ear with one finger, then
fluttering her hand. "Aren't they beautiful? The ring is a flawless two
carat diamond – and the matching earrings are one carat each."
"But weren't they dreadfully expensive?" I asked. Then added, "That
Jaguar in the garage?"
"Isn't it a dream? I've always wanted one in that shade of red. They
just delivered it this morning!"
"But didn't these things cost a lot of money?" I asked.
"Maybe – but I have lots, don't I?" she said flippantly. "After all,
what's the use of having money if you can't spend it!"
"But are you talking about the money from our account?" I asked,
worried.
"No. I'm spending the money from MY account. It's mine, isn't it?
And there's still tons of it left!"
I looked at her aghast. Yes, we were rich – but it was money my family
– not hers – had accumulated by conservative means over the generations
– and she seemed to be spending like a drunken sailor! I sighed to
myself. After all, I had signed our money over to her – and what she
had spent so far? It was really a drop in the bucket. My musings were
cut short. She had said something.
"What was that darling?" I asked, "Didn't hear what you said."
"We have a new member in our little family!" she whispered excitedly.
Then spoke loudly. "Bridget! You there?"
A large, swarthy, woman appeared immediately, looking admiringly at
Pamela. "Yes Mistress?" she said.
"Bridget! I'd like you to meet my husband! "
"Your husband ma'am?" the woman said, looking appraisingly at me, her
eyes taking in my hair, makeup – and the dress of course. Then she
came over, with her hand out as if to shake hands. Instinctively I held
mine out – and watched it get engulfed in hers. "Hi!" she said.
"Carole? Bridget is our new housekeeper!" Pamela said. "I think I need
some help around here – so it seemed the most sensible thing to do."
"Pleased to meet you Bridget," I said, my voice small. "But my name is
Harold."
"Carole! Please! I told you why I want you to start accepting your new
name! You'll just confuse Bridget! Say that you're sorry – please?"
Pamela was upset – and it showed.
"Oh! He doesn't have to apologize to me. I want Carole and I to be the
best of friends," Bridget said softly, still holding on to my hand. "I
like your dress Carole. Did you pick it yourself? It looks nice on
you."
She was soft spoken and quite deferential, but she scared the hell out
of me. In my recent experiences with women – even my own WIFE for
goodness sake – I'd discovered a trepidation within myself, a feeling
that I was inadequate beside them. Here, with her holding onto my hand?
I literally felt frozen with fear! At the same time? Should I admit
that I was dressed in the fashion I was because I'd been forced into
it? I mumbled something incoherent.
"Oh Carole!" Pamela said sharply. "Your diction is becoming atrocious!
You must learn to speak UP!"
"I was saying that maybe I should change before Suzette gets here?" I
said, managing a little more clarity.
Pamela gave me an impatient grimace. "Whatever for? Honestly Carole,
you're beginning to THINK like a woman! It's most disconcerting!" She
made a tutting sound.
"Mistress?" Bridget said. "May I suggest that Carole and I have a
little chat? Get to know each other?"
"Yes! Good idea. I'm glad that someone can think straight around here!"
Pamela said, obviously aggravated, and left the room. I became even
more fearful. Bridget had never let go of my hand and was staring quite
hard at me now, a glint of amusement in her eyes.
"Carole? I asked you a question a little while ago, and you never
answered. Now, I consider that a very rude way to treat a servant,
don't you?"
"I'm . .I'm . . terribly . .frightfully . .. sorry Bridget. I got
distracted."
She was taking me over to the sofa, sitting down and pulling me down to
sit in her lap! Finally, let my hand go and put an arm around my
shoulders, then pulling me into her embrace, gently chucked me under
the chin! Smiled possessively at me. "That's all right pet. But you
won't be rude to Bridget again, will you? Ever again?"
"Oh no, Bridget !"
"Know something? You're the prettiest master I've ever had! Do you
like dressing up like a girl? And, like I said? That's a very pretty
dress. And mistress tells me that you're going to get a makeover
tonight!"
I started to try and answer her questions, but she put a large finger
on my lips. "That's all right dearie. I don't mean to be so nosy!
Mistress tells me that you're the office girl for a law firm?"
Horrified, I looked at her. Pamela had told her that? Nodded.
"She's very generous you know! Bought you a LOT of nice clothes for you
to wear to the office."
"I didn't know that," I whispered.
"Well, I thought you didn't, because if you had, you'd never have upset
her now, would you?"
"No."
"Of course you wouldn't have – a nice girl like you! But I understand
that you're rather careless with money?"
"What? What do you mean?"
"Didn't your employer ask mistress to keep an eye on your daily
expenditures? And didn't she say she would?"
"Well, yes . . but you see . ."
"Well mistress has asked me to take that function over. Says that
though she's never had to chastise you, the day could come when you'd
need discipline, and she's too fond of you to administer it."
"Discipline?" I croaked.
"Oh nothing much – a spanking would probably be all that would be
required. That's fair, don't you think?"
Stunned, I could only stare at this huge woman. I was to report to HER!
A servant!
"Oh yes. Very fair!" I stammered.
"Wonderful!" she enthused. "Now, go over my knee," she added, starting
to pull me in that direction.
"But I haven't done anything wrong! Please don't spank me. Please?"
She reached into a pocket and pulled out a latex glove, which she put
on her hand. "I'm not going to spank you – you silly little sissy!" she
said, pulling my panties down. "I'm just going to remove your plug! But
keep in mind, if you don't continue to walk properly? I'll have to
replace it! You won't forget, will you?"
"No." I panted, humiliated beyond words.
"Then every morning before work? You can report to me and I'll insert
it for you. Okay?"
"Mmmm – yes. Oh yes!" I gasped as I felt her withdraw the plug.
"Oh! You and I? We're going to be friends, aren't we? Such intimate
friends!" she whispered, now sticking a finger into me and wiggling
it, then slowly extracting it – then forcing it in again!
Naturally, Pamela chose that particular moment to return – and bring
Suzette, her hairdresser with her! She was in the room before she took
in what was going on.. "Oh Carole! I didn't mean to disturb your fun!
But while we're here, why don't you say hello to Suzette?"
With Bridget's hand on the small of my back, and her finger continuing
to rape me, I could only gape upwards a little, so didn't see much of
Suzette's face, though I knew she had come up and was fingering my
hair.
"Pamela? This will be NO problem at all! I'll be able to shape and fix
it for tonight – no sweat!" Then she giggled, "I'm sorry Harold. I'm
usually better mannered – but business always comes first, right? Nice
to meet you!"
I groaned unintelligibly, but she seemed to take it as an appropriate
answer. Then, chatting amicably, the two women left me under Bridget's
care as if nothing was amiss!
Then, finally, Bridget's finger was out of me. I felt her rearrange the
waist band of my panties, then she was sitting me upright again.
"Wasn't that fun?" she asked rhetorically, a sly expression on her
face. "But now Carole? Walk over to the far wall, and back. I want to
make sure that you haven't forgotten how to walk properly!"
Knowing that she was still holding my plug close by – I remembered all
too well how to walk, and delighted her with my mincing effeminacy as I
sauntered to the wall she'd pointed at – and returned.
Suzette seemed to have a good reputation as both a cosmetician and
hairdresser – and working in conjunction with Pamela had me essentially
feminized before dinner time. It was particularly galling to me to
discover how easily she 'converted' me – especially with her going on
and on about my beautiful complexion, my lack of facial hair and, most
upsetting, my eyelashes – which she raved about. She spent most of the
time until then doing 'odds and sods' as she put it. Hair shampooed,
then trussed up in a turban. Eyebrows waxed (That was painful!) and a
quick manicure and pedicure. Ears pierced.
Pamela decided that it was silly for me to have to cook dinner then
have the clean up etcetera, so we ordered pizza – (of which I got one
tiny slice) and salad – which I was allowed to eat as much as I wanted
– but with minimum dressing, I didn't care for rabbit food – memories
of Gloria referring to me as a 'bunny' still fresh in my mind.
After dinner, I was finally allowed to take my dress off – only to
discover that I was now being fitted with breast forms. To tell the
truth, I'd always thought of them as the old fashioned 'falsies' – you
know, something formed to fit inside a bra? But this was quite
different.
Aghast, I discovered that they were going to be adhered to my body –
and for DAYS at a time! I also found out that, as Suzette
enthusiastically reported, they would feel and act 'just like the real
thing!' So after quite a time taken in measuring me, and making tiny
little indexing marks on my chest, I was introduced to the joys of
semi-permanent breast forms with, naturally, a lacy bra to keep them in
place.
Suzette had wanted me to feel them with my hands and they had felt
surprisingly light.. But once they were affixed? It felt strange – as
if my whole center of gravity had changed – and my new style of walking
seemed to accentuate the strangeness considerably. Another thing that
compounded my strange feeling? Pamela's reaction!
Once my 'breasts' were attached and I was having my hair 'done'? She
grew a little distant from me. Still referred to me as her 'hero' and
'macho husband' – but there was an underlying mockery there that was
becoming more and more evident.. Started telling me how 'gorgeous' I
was now – and how I'd be the 'prettiest office girl' in the whole
building when I returned to work the following day. She produced my new
baby dolls – Pink now – while she wore yellow. She smiled when she saw
me walk – then hung over us as Suzette finally finished with my hair
and applied my make up.
Bridget had disappeared by the time that Suzette started packing all
the tools of her trade – with a tiny application of a very expensive
perfume to my wrists, ears, and bosom. In my high heeled slippers –
pink naturally, and a saucy ribbon in my styled hair – also pink? My
makeup, artfully applied? Glistening nails on both fingers and toes?
My bracelets? I was almost a match for my lovely wife, Pamela. Who
seemed excited for some reason now.
Not by me – obviously. I was now nothing more than a girl companion,
someone to discuss makeup, movies, TV, and magazine articles with.
After a few disapproving glances I learned what responses were 'valid'
and what were not. Accordingly, I spent a leisurely half hour talking
'girl talk' with my wife. During this period, I found out that she had
quite a crush on Jenny – the lawyer who'd been advising us – only she
now referred to her as 'Jen'.
"Oh! Wait until you meet her! So strong! So intelligent! So masculine!
You'll love her, just wait and see!"
Then, the doorbell rang. It was normally my job to answer it but,
dressed as I was – and the fact that Pamela raced to answer it – I
suddenly had the premonition as to who it was going to be. Feminine
intuition? I don't know – but it was Jen.
She (?) Though I'm now used to thinking of her as a 'he' – though
taller than me, was a fairly stocky, muscular woman. Fair hair, bright
blue eyes – a very penetrating stare that she focused on me as she
advanced to be introduced. "You're Carole? Used to be Harold? You're
much prettier than I'd supposed you'd be. Matter of fact! You make a
damn fine looking woman! Come here and give me a kiss."
Meekly, I advanced on her – Pamela walking and smiling alongside me.
"Didn't I SAY that Jen would appeal to you, huh? Isn't she the
greatest?" she said, more than once. And she said to Jen. "Look at how
she's walking. Isn't she CUTE?"
That my wife had referred to me as a 'she' didn't seem to bother me
too much. Jen didn't reply, just stared at me until I minced into her
arms. She took my arms and draped them around her neck and with her
being taller than me, I had to stretch against her. For some reason, I
found this most erotic – especially when she put her hands on my
buttocks to pull me into her. Surprisingly, her kiss was very chaste.
When she disengaged, she smiled at me. 'Nice teeth,' I thought.
"Let's dance?" she said softly. "Pamela? Put on some music, huh?"
I heard Pamela giggle a little. Then the lights dimmed and soft music
surrounded us. Jen felt so strong, and I felt so weak. It seemed
absolutely natural that I played the woman's role. Gradually, I felt my
aversion to femininity disappear – it was if my body were melting into
hers. She was whispering words that were soft and enticing, and I was
nodding my head and making soft mewling noises as she led me over to
sit on a chair.
"I'll be back in a minute. Okay honey?" she whispered. Speechless with
soft lust, I could only nod.
Pamela was taking a hold of my hand and tugging me gently over to sit
beside her at the dressing table bench. I looked at the two women in
the mirror. "My lipstick's all mussed up!" I said, distracted a little
by the fact that one of the women in the mirror was lip syncing what I
was saying.
"Yes! I know! Time to freshen up! Here let me do it for you. Don't want
you all smeared up for Jen, do we?"
"But I thought that Jen was YOUR girlfriend?" I managed to ask trying
valiantly to keep the jealousy out of my voice, when she paused in
making my lips pretty again.
"Oh No! BOYfriend would be more like it – and anyway? Don't you like
her? Isn't she so strong and masculine? I thought you needed to meet
somebody like her. You DO like her! Don't try and pretend to me!"
I saw the girl in the mirror blush. Her lipstick was wet and scarlet
looking now. Saw her lips move again as I answered Pamela. "Yes – I
like her. But it's ME that is masculine . .there's something wrong here
. . ."
She patted my thigh – caressed it actually. "Masculine? Don't be silly!
You may be a male, because of that little thing you have in front of
you – but sweetie? I'M more masculine than you are!"
I opened my mouth to protest, but she over-rode me. "You're sweet,
soft, and girlish. Always were. Now? We're just introducing you to the
joys of being what you should have been all along – a girl! Now stand
up! Lean over this bench, please?"
"What for?" I asked, though I did as she'd said.
"A girl's gotta be ready at all times!" she giggled, lifting up the
back of my baby dolls and pulling down my panties.
"I've been walking properly!" I protested, almost crying as I felt what
she was doing.
"Huh?" she asked, continuing to lubricate my back passage. Then she
laughed. "Oh NO sweetie. It's Bridget's job to put your plugs in and
out now. Just relax." Then, to my surprise, she just pulled my panties
back into position and gave me a tiny slap on the posterior. "That's
it! Remember, just relax!"
I wasn't so stupid that what she was telling me didn't make sense, but
I didn't have any time to react as Jen was back in the room, smiling
dangerously as she came, took me by the hand and led me to the bed. I
didn't make any resistance – couldn't. She lay on one side of me, and
I felt the bed shift, and knew that Pamela was on the other.
Then, in a fog from some forceful necking, I found myself being
positioned into a kneeling position and pulled back until my backside
was hanging over the bed.. Discovered that Pamela was putting a condom
over my erection 'So's you won't mess your nice jammies," she
whispered. I could see the white of her teeth in the darkness as she
smiled.
Within minutes, Jen made me into her woman, entering me from the rear
and whispering pretty words. I still cried but, after a little while of
moving in rhythm with the dildo inside me, felt a pressure growing and,
to my surprise found I was ejaculating into the condom!
"There, there, Carole! Liked that, huh? Now it's time for you to come
and please mummy!"
And, where Pamela had watched me become Jen's woman – Jen now lay
and watched as I became Pamela's lesbian husband!
The following morning it didn't seem so bad, as I laid over Bridget's
knees so that I could have my plug inserted. She used her finger to
tickle me a bit there, but I was sore and asked her, nicely, to stop –
and she smiled understandingly and complied. I didn't quite understand
the clothes I was to wear though.
"Isn't this a maid's uniform?" I asked, fingering the pink, extremely
showy, satin dress with the mass of frilled petticoats – and the
particular lacy panties – also in satin. "I don't know if Miss Matson
or Miss Edna will approve!"
Bridget slid her hand up inside my dress and caressed my backside.
"Don't worry about it sweetheart – just tell them that Bridget dressed
you this morning!"
I left Jen and Pamela necking softly in bed. They both smiled as I
curtseyed (Bridget's 'suggestion') before I left. She (Bridget) then
drove me to work and escorted me to the office, coming in with me.
"Time I met the other ladies in your life Carole," she told me.
Neither Miss Gloria nor Miss Edna seemed put out about my attire – as a
matter of fact, I was surprised to discover that they had a frilled
maid's cap and matching apron that went very well with the dress. I
started feeling uneasy. So many things that didn't make much sense, –
how Pamela was aware of things that went on in the office – and vice
versa. How could Gloria and Edna have had an apron and cap that went
with my dress? How come Bridget knew her way to the office, when she'd
never been there before?
But I wasn't given much time. Had to make coffee and serve it to the
ladies, then Gloria called me into her office – and pointed under the
desk.
"Time for your burrow little bunny. In you go!"
I knew better than to argue – so backed in. She then sat in her chair
and pulled it in enclosing me, and hiking her skirt up and spread her
thighs. Sighed happily as I started to tongue her. Then I heard a
woman's voice – it was familiar, though it took me a few seconds to
realize that it was Dorothy – my old partner.
There was definitely something different about her voice that I
couldn't quite place – and then I realized what it was – she was no
longer speaking in the breathless feminine way she had in the past –
she sounded like a much more mature woman – with lots of confidence.
They spoke for a few minutes, then, to my amazement, Gloria stood up
from her desk and moved away. Then, someone else sat in the chair.
"This the chair that has magical powers?" Dorothy said, hiking her
skirt and slip up to reveal her panties! Then she spread her legs!
I knew what was expected of me now, so moved into her and started
licking and sucking. I could feel her relax – and then she was reaching
under the desk and patting me on the head. "MY! You've finally found
something at which you excel Harold – oh, sorry! Carole! Just keep it
up for a little while, okay? That's a good girl!"
Then, only a few minutes after she'd orgasmed, she was gone – and
someone else was in the chair. But this time? There were no panties
under the skirt – just a large dildo! I knew what I was supposed to do
but there wasn't enough room under that desk – then the chair rolled
back a little and still on my knees I followed it – then just as I
neared it, the chair rolled back some more – and again I neared it and
again it left – and then I was out in the light – and it moved away!
I looked up at Jen smiling at me and she beckoned me with her finger
and, in my pink satin dress, my lacy white apron getting in the way as
I moved along on my knees, my flounced maid's cap bobbing, I followed
her all the way to the center of the office. There, Jen looked down at
me.
"Want to be a good girl, Carole? Give Jen a nice blow job?"
"Yes," I said, near tears, seeing all of the women encircling me.
Pamela, my wife amongst them, smiling proudly and encouragingly.
"Hasn't he turned into the nicest girl?" she boasted as I took the
dildo into my mouth - and with my head bobbing as I moved up and down I
blushed at her praise as all of the women laughed and applauded.
Finally, something was ejaculated into my mouth. I choked, but taken by
surprise as I was, had to swallow!
"Good girl! What a natural!" Pamela said helping me to regain my feet
after Jen removed the dildo. Then, she put her arm around my shoulders
and, turning and making me follow, made a complete turn, making me
face all the women surrounding me.
"Carole? We did this to you today to let you know what you are. Here?
You're the office girl. At home, you're a maid. Here, your desk is that
one over there. At home, you'll have the maid's room adjoining Bridget.
There, you will address her as Miss Bridget, me you'll call Mistress,
and Jen – you will address as Master. Dorothy, Gloria, Jen, and myself
are setting up a new coalition of which you will own nothing . ."
"Though thanks for your money sweetie – we sure needed that!" Dorothy
interrupted.
Pamela smiled. "Very true – but you've been pleasing us four partners
– and as Edna and Bridget are going to be major forces in your life
from here on in and, as it's going to take some time for us to cross
the 'T's' and dot the 'I's' I'd suggest that the three of you go home –
and start becoming friends."
Edna was standing on one side of me, Bridget on the other. As Pamela
finished talking, each of them linked an arm in mine and started
walking me out of the door, with me too dazed to comprehend what I'd
just been told.
"Yeah! Intimate friends!" Bridget said.
"Sounds like a plan to me!" Edna said patting me possessively on the
ass..
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