Stuck In The Middle

By: Throne

I guess  you could say I was stuck in the middle at work.  I was a junior
account manager, which doesn't carry much weight.  My boss, Drake
Hasson,
promoted three people over me in the year I was there.  My wife Vicky
wasn't happy about that but at least we didn't have any money worries,
not with her earning twice as much as me, plus hefty bonuses, at her job
as a senior account manager for another company.  Part of my problem was
that I had neither the personality nor the appearance to move up the
corporate ladder.  I'm shy and soft-spoken.  I'm also short and slender.
Not only do I have fine features and smooth skin, but I can't even grow a
proper mustache, so it's impossible for me to look more mature.  At home
I couldn't command my wife's respect, not only because of those
shortcomings but also because of my lack of sexual prowess.  My penis
undersized and when I get aroused I tend to finish too soon.  Way too
soon.  And I get aroused just from being around Vicky.  She is tall,
full-figured, and has thick red hair that falls almost to her waist.
Other men ogle her, making me wildly jealous.

Even before we got married, Vicky established the rules of our sex life.
Mainly I gave her pleasure with my mouth.  She enjoyed teasing me and
then reminding me that I was only allowed to orgasm when and how she
said.  The latter usually involved me playing with myself or, if I was
lucky, being allowed to rub the tip of my little dick against the outside
of her moist warm pussy, while she toyed with my nipples, until I
spurted.  Then I had to clean her up orally, at the same time giving her
a climax.  It worked for both of us.  She got off on controlling me and I
was totally under the spell of her stunning curves, sweet face, and
superior attitude.  Our situation changed, however, after she stopped by
my office, met Drake, decided she liked him, and found he felt the same
about her.  How could he not, with the way she looks?  I didn't even
protest when she told me they were going out on Friday night and that I
should wait up until she got home.  Nervous and restless, I sat and
fidgeted, got up and paced, and then looked out the window, repeating the
cycle over and over until midnight.  That's when my wife returned.  I
watched her get out of a large expensive car and come up our front walk,
accompanied by a tall handsome man.  I scurried further into the house as
the door opened, then peeped out to see them enter and embrace.  He
kissed her hard on the lips and she responded passionately.  That went on
for several minutes before they finally said goodnight and he left.

She called me and told me that she and Drake had decided to make some
changes in my life.  Then she added that I wouldn't find out what they
were until the next day.  In a state of nervous distraction I got ready
for bed.  Vicky put on her most seductive nightie.  The way it showed off
her contours had me shivering with frustrated need.  She told me I would
be sleeping naked.  We got under the covers and there I was, next to my
marvelously attractive wife, buck naked myself, and unable to do anything
about it.  She murmured to me that Drake was delightful and had nearly
charmed the panties off her, but that they had decided to wait for their
second date to go all the way.  I was shaken up but too dominated to say
anything about it.  Instead I just lay there while she mentioned how he
had put his hands on her arms, patted her butt, hugged her tightly, and
whispered suggestive remarks.  But, she reminded me, Saturday's
revelations would have more of an effect on me than any of that.

In the morning, still fully undressed, I ground fresh coffee and brewed
it.  I made her toast and put it on a plate that went onto a serving
tray, along with butter and jam.  I served her in bed, where she sat
upright against an oversized pillow.  That nightie showed off her
magnificent bust.  Her streaming red hair was draped over one white
shoulder.  "Sit over there on the wooden chair," she said, emerald eyes
glinting with mischief.  "I want to be able to see your face while I tell
you what Drake and I have decided to do to keep you in line, now that
I'm
going to be cheating on you."  Keep me in line?  As if she needed to do
anything additional to control me.  She went on, "As your boss, he's
going to give you work that keeps you from interacting with the clients
face-to-face.  You'll be doing more record keeping, file searching, and
routine phone calling.  We're going to have some fun altering the way you
look, dear.  And if you don't behave, we'll let the news out that your
wife has made you a cuckold.  Do you want everybody to know about Drake
and me?"

I seized up inside.  All through my life I've been overly sensitive to
what people think about me.  I could only shake my head.   "Good boy,"
she said before taking a leisurely bite of toast and sip of coffee.  As I
sat there, squirming inside with worry, she went on, "The first thing is
that, under your boring suits and dress shirts, you are going to be
wearing panties Monday morning.  I also want you to have on..."  She
paused, apparently considering options, then decided, "... clear nail
polish.  And of course you'll have to start taking better care of your
nails, using a file, an emery board, and a cuticle stick.  We'll see how
well you do with all that before we decide what's next."  I stared in
disbelief and wanted to know, "But won't people notice?"  She smiled and
told me, "Probably not at first, but we won't be stopping with just the
ends of your fingers."  Vicky snickered at whatever she was thinking and
told me to go and get her a glass of fresh squeezed orange juice.  I
realized that I still hadn't had anything to drink or eat and was about
to say something, but then thought better of it.  Obediently, I hurried
off to fetch what she wanted, my bare bottom visible to her as I rushed
out the door.

Sunday I took care of my nails.  Vicky mentioned the possibility of me
having a manicure at a beauty salon but I assured her, my voice unsteady,
that I would do a good job myself.  Once the clear polish was on and
dry,
it seemed very noticeable to me.  When I said so, my wife just shrugged
and said, "Whatever."  Obviously I wasn't going to have the slightest say
in the matter.  Then she reminded me that I had to try on my new
panties,
which she had gone to the mall with Drake to purchase.  She mentioned
that they had told the salesgirl they were for her non-existent younger
sister.  Something about that lie made me blush.  There were three pair,
pink, orchid, and lime.  She decided I could start with the latter one.
After I got home I would hand wash whichever I wore and put on a fresh
pair to sleep in.  In the morning I would clean the sleep pair and put on
the remaining one.  Wearing only the panties, my nails reflecting light,
I felt like I was on display, which I guess I was.  She reminded me with
an impish smile that Drake would know what I was wearing under my slacks
every day.

Monday morning came too soon.  She sent me off to work with with a swat
on the backside.  At the office I felt sure everyone had their eyes on my
hands.  No one said a word but the thought that they might be privately
discussing it kept me off balance.  Plus, Drake had his assistant, Pearl,
a tall woman with overblown curves like my wife's, introduce me to my
new
duties.  Did Pearl know about the panties?  Was she checking out my
nails?  If so, would she tell any of the other women?  Nothing happened
but by the end of the day I felt exhausted.  I headed home and as soon as
I got there I had to remove and hand launder the panties I had worn and
then put on the next pair.  Dressed in only those, I had to fetch my wife
a glass of red wine.  She made me sit at her feet and tell her about my
day, amused that I had felt so exposed.  "Well," she said, "if you feel
that way now, how will you be as we add more changes to your look?"

"M... more?"

"Naturally, darling.  I told you that.  It's sort of a game we're
playing.  I'll think up new fashion statements for you to make and Drake
will let me know what he thinks of them.  The whole project excites me
and talking about it will make our dates more fun."

The next of those dates came in the middle of the week.  She went for
appetizers with him but they skipped dinner.  He didn't want them to have
full stomachs when they got to his luxury apartment, and especially not
when they reached his bedroom.  I suppose I had been in denial about them
planning to sleep together.  But the full reality of it hit me hard.
There I was in panties and wearing clear nail polish, feeling even less
like a real man than usual, and the wife who denied me sex was about to
grant that privilege to my handsome boss.  As I had before, I spent an
agitated evening until her return.  Vicky wore a happy glow and didn't
hesitate to tell me that it was because she had just had the best sex of
her life.  And part of the reason it had been so good was because they
had chatted during foreplay about what to do to me next.  She figured
Drake was an alpha male who got a kick from dominating another man.  As
for herself, she declared, "I guess I'm just a bit of a bad girl and I
get turned on by messing with your head.  I'll tell you on the weekend
what we have in store for you next week."  She obviously enjoyed making
me wait, as well.  So for several days I had to continue worrying about
what people in work might think, as well as what my wife and her lover
would subject me to next.

Finally, on Sunday evening, Drake stopped by with a package for me.  He
said, "Since this time it's a male item, I did the shopping."  I secretly
felt relief that they hadn't chosen something else feminine.  But when
he
gave me the bag containing his purchase and I looked inside, I saw five
pairs of socks, all of them in garish colors.  Shades of yellow and gold
and one red-bordering-on-hot-pink.  He chuckled and said, "Hey, if you're
careful, they'll hardly be visible."

"Right," my wife seconded, "so it's either spend all your time hiding
them or have everyone see how flashy they are."  I looked at my shiny,
well-kept fingernails and then pictured myself wearing those socks as
well.  What kind of message would that send?  Plus, at the office Pearl
had been bossing me around, not blatantly but enough that others could
pick up on it in small ways.  Everything was making me so self-conscious.
Then my wife said, "Well, aren't you going to thank Drake for getting
you
those pretty socks?"  I took a deep breath, wanting to say something in
my defense, but then answered impotently, "Thank you, Drake.  I...
appreciate it.  Thank you, Sir."  He answered, "No problem, buddy."
Then, I guess because it excited them to put me in that situation and
keep me there, he took her in his arms.  She turned her face up to him so
they could share a long kiss.  His hands caressed her back and they
ground their bodies together.

Then he announced, in his deep authoritative voice, "You can try all
those cute socks on for us.  Go strip down to just your panties and then
come into the bedroom and show us each pair as you put them on.  I've
been waiting to see the guy whose wife I stole when he's the way she
makes him dress.  This'll be fun."  I tried not to let my humiliation
show.  Instead I did as I was told.  When I returned, looking quite
unmanly, they were undressing each other and enjoying foreplay but
stopped long enough to snicker at me and make a few comments.  "That
really brings out the sissy in you."

"I'm sure the socks will be a big hit at the office.  Maybe this'll start
some people wondering what you wear UNDER your business clothes."  The
next time I appeared they had started having sex and so only spared me a
glance.  On the third pair they were at a bed-shaking peak.  By the
fourth their orgasms had subsided and they were lying alongside each
other, enjoying the sweet aftermath.  When I appeared wearing the final
ones -- bright unmissable orchid -- she was cuddled up against him,
stroking his broad chest.  She had a pleasure-sodden look on her face as
she observed me and said, "We need something to call him.  A name that
will fit his new look."  He said, "Well, I don't think it should be too
girly, because we haven't made him dress all the way.  He's still got his
crossdressing cherry."

"Hey, that's it," exclaimed my wife.  "What?  We'll call him
Crossdressing Cherry?"  She gave his thick bicep a playful swat.  "No,
lover.  We'll call him Cherry.  I like keeping him a CD virgin.  Stuck in
the middle, with everyone at the office wondering why he's making these
fashion choices.  We can keep this going for a long time."

And that's what they did.  Next came several sweater vests, both
pullovers and button-ups, all guaranteed to draw the wrong kind of
attention.  Those were followed by louder neckties.  After that was lip
balm, just a light coating.  It was clear but noticeable.  I was given a
'week off' then, time to let my co-workers get used to all that.  Time,
also, for me to dwell on their veiled reactions and worry more about what
they were thinking and if they would guess, or if the lovers would
reveal, what else I had on, unseen.  I got myself somewhat calmed down
with lots of rationalization and a little denial.  But then they added
stockings to my wardrobe.  Some days I was allowed to wear my bright
socks over them, and others I had a glimpse of nylon showing at my
ankles.  I can't tell you how upsetting those latter times were.  How
could anyone mistake what they were seeing?  I always felt someone was
noticing and that there was a whispering network of speculations.  Soon I
was instructed to place my hands in a more feminine manner, whatever I
was doing.  I definitely spied others taking note of that.  Along with
having to keep my knees together, it sent a strong signal.  The specter
of exposure hovered near every minute of the workday.  Pearl made
comments that might have been neutral but to me they seemed to be
secretly conveying knowledge of my situation.  That I found her so sexy
made it that much more distressing.

More changes of wardrobe followed.  I was given pants that were cut
differently, a hint tighter across my bottom and in the crotch.  And my
shirts, while not flamboyant, had fuller sleeves and longer collars,
which made them, at least to my eyes, seem more like blouses.  Then there
was a narrow gold bracelet, cleverly selected because it could be worn
by
either a man or woman.  With everything new I had after several months it
was uncomfortable for me just to get into the elevator.  At each floor
more people might get on, many of them furrowing their brows or raising
their eyebrows at my look.  A few young men who I imagined were gay even
gave me sly smiles.  And one older executive, in a three-piece suit,
winked at me -- I think.  Or maybe my imagination we getting the better
of me.  Vicky and Drake had put me in a relentlessly upsetting position.
As my wife had said, I was 'stuck in the middle'.  But they weren't done
yet.  Friday became bra day.  I had to wear a pale-colored training bra
under a shirt that was barely dark enough to hide it.  There was still a
chance, I knew, of being detected.  What if someone got a peek of the
undergarment through the spaces between my shirt buttons?  I spent every
Friday even more concerned that usual.  And the rest of the week I
dreaded Bra Day.

The year dragged on, each day feeling like a week, each week like months.
I was always squirming inside.  Waiting for someone's sentence to end
with '... and are those panty lines I see under your tight pants?'  I
also kept imagining someone would use my other name, Cherry.  At the same
time, my wife and her boyfriend loved to remind me that I was being
cuckolded.  They would make jokes, send me text messages on my phone and
e-mails to my work address, even mail me items like a lace hanky, with a
note that I was to stuff it down into the breast pocket of my shirt, but
not too far.  To them it was a game but all I could think about was the
ever increasing chance of being discovered as a sissy fashion plate.  On
top of everything else, the fact that I wasn't getting sexual relief
added to my nervousness.  That was resolved somewhat when I began to have
wet dreams.  Vicky discovered cum in my panties one morning and
confronted me.  I desperately insisted that I hadn't played with myself.
I was so upset that she believed me, called Drake, and had a good time
telling him about my latest embarrassment.  I was shamed beyond words.
It kept happening, about once a month.  Eventually, my a full year of
being forced into this bizarre gender limbo was drawing to a close.  They
wanted to do something special as a 'treat' for me.  I dreaded finding
out what that was.  It turned out that, while Drake relaxed at our house
and watched football, Vicky took me to a unisex salon and had a fey young
man consider my hair, which is normally a dull brown.  He recommended a
shampoo and conditioner.  I dared to hope that was the end of it but then
he added, "Have you considered getting him some highlights?"  I silently
prayed that she would veto that suggestion but then I saw the wicked
light in her eyes.  She laughed merrily and said, "Tell me more."

That was a Friday.  He gave me bright highlights in front, done some
cutting, and used gel to make fuller.  There were also less obvious
highlights on the sides.  The end result was something that, in
combination with all the other 'improvements', as they liked to call
them, made me look unquestionably un-masculine, if that's not some kind
of double-negative.  That was the roughest week yet, especially Bra Day
Friday.  There followed another 'vacation' week, going to work with no
additional changes.  That brought us to the end of the year.  With only
days remaining, I was directed to speak more softly and punctuate my
sentences with breathy inhalations that sounded like sighs.  Can you hear
me?  "I'm sorry (sign), Pearl.  I'll have those records in your in-box
right (sigh) away."  Or even worse, "Certainly (sigh), Mr. Jepson.  I
don't mind getting coffee for you (sigh)."  Yes, I had become the 'coffee
bitch' for several of the people above me.  And when I answered the
phone
some callers addressed me as 'Miss'.  Then it was New Year's Eve.  Drake
was taking Vicky out for a special evening.  I could see that their
feelings for each other had deepened.  In my seriously sissified state I
had no leverage to win her back.  She would go on cheating with him, her
libido elevated by the way they treated me.

Before they left for their night out she did two things.  First she
perched a little maid's cap atop my highlighted hair and gave me a list
of housework to do while they were gone.  Then she announced my New
Year's Surprise.  "For the next twelve months you won't have anymore
changes made to your look.  We wanted to get at least one of your ears
pierced but we decided it can wait.  How do you feel about that?"

"You mean I won't have to wear panties or those... odd... clothes
anymore?  Or the lip balm or...?"

"No, silly," she interrupted.  "I don't mean that at all.  I'm just
saying that we're going to keep you the way you are for the next year.
Won't that be fun?"  I'm sure my expression revealed what I was really
thinking as I said, in my softest voice, "(sigh) Yes, dear.  Thank you
both."  They sniggered at me and left, calling back, "Have a lovely time,
Cherry."  I did my housework and contemplated another year of enforced
androgyny.  Of being constantly under the scrutiny of the rest of the
staff, as well as everyone else in the building and on the street.  And
of having my wife continue with her infidelity.  And, maybe the worst of
it, having to agonize over what waited for me after my year long
'sabbatical'.  What changes would they make to me THEN?