Poor Michael

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?”