IT'LL BE FUN
By Persephone © 10/31/16
A tale of an old trunk, an old dress, an idea for a Halloween costume
party, and a job contract that all conspired against Jack to keep him in
skirts and dresses. And if he wins will he lose or if he loses will he
win? Read and find out.
This started out as a short simple Halloween story but it turned into a
monster before I had finished. I hope you like it. Feedback appreciated.
Chapter One
Jack and Casandra (Sandy) met in college at the end of their sophomore
year and dated during their junior year. They moved in together during
the summer break after their junior year. After graduation they rented a
small apartment for a couple of years and then, as Sandy moved up the
corporate ladder and Jack's consulting business grew, they decided to
buy a house together. They found an old house built about 1900 that
suited their needs and taste. Marriage had been mentioned many times but
just didn't seem to be necessary. It was something that they planned to
do "later" when things settled down and they were ready to start a
family. But buying the house seemed to bring out the domestic side in
Sandy and she hinted until Jack finally caught on and popped the
question. They got married in a small civil ceremony with just a few
friends present. Then Sandy continued to pursue her career and Jack
concentrated on growing his business. Kids were not in the formula yet.
They both still enjoyed their freedom for vacations, hobbies, and other
interests.
One of Sandy's hobbies was buying and restoring antique furniture.
Usually the smaller things like end tables, nic-nac shelves and such.
She loved to go to estate sales and rummage through the lifetime
collections of things that families sold off after the passing of a
family member. Jack didn't like picking over "the bones of the dead" as
he called it but he did appreciate the beautiful old solid wood
furniture that she refinished and reupholstered. It made their house
very "homey" and gave him a comfortable feeling. She had even learned
how to crochet doilies to add to the feeling.
Jack was busy in his home office one Saturday cleaning up the last few
things on one of his contracts when Sandy returned from a day of "bone
picking." He heard her car door and then shortly afterwards she poked
her head in his office door. "Can you give me a hand unloading the car?"
she asked.
"Sure. Be right there."
Jack went outside and found Sandy's Ford Explorer backed up to their
detached garage. She was just opening the back when he arrived. "You
won't believe the beautiful old wooden steamer trunk I found. It's
locked up so I have no clue what's in it but I plan to refinish it and
use it as a coffee table in the den."
Jack tugged the large trunk out of the back and set it on the garage
floor while Sandy was rummaging through her tools. "There it is," she
exclaimed as she held up a tool that looked like a bent awl. "This is a
pick that I use for cleaning out carving on furniture. It should work to
open that lock."
"Well I'll leave you to your treasures."
"Aren't you curious what's inside? Stick around for a few minutes."
"Okay. Probably just a bunch of old junk though."
A few moments later Sandy triumphantly announced, "There! That's got it!
Now let's see what treasures we have." Jack let out a small sigh as she
raised the lid.
The top drop in tray was filled with small things. Sandy held up lace
handkerchiefs, silk stockings, garter tabs and other very old bits and
pieces of a female wardrobe. She also found a jewelry box containing
necklaces, rings, bracelets, earrings, and broaches. There was also an
envelope with a letter inside. It was addressed to just, "Augusta."
Sandy pulled out the letter and read aloud, "Dearest Sister Augi. It was
so wonderful of you to visit us for the wedding. We thoroughly enjoyed
having you here. Too bad you couldn't stay longer but your tickets
didn't permit change. Sorry your trunk didn't arrive at the dock on time
for the sailing but Albert arranged for it to go on the next ship
sailing for New York so you should have it a few days after you get
home. All our love, Your sister, Hazel. Kidderminster 1893.
"I wonder why she never unpacked her trunk?" Sandy questioned.
"Who knows," Jack answered. "Maybe she didn't need what was in it."
"I doubt that. She'd have wanted the jewelry at the very least. Let's
see what's in the rest of it," Sandy said enthusiastically. Jack sighed
again as he lifted out the tray.
Sandy started going through the clothes. She pulled out an old whale
bone corset and looked at it. "Check this out. What a torture device but
it's really beautiful. Look at the brocade panels," she said as she held
it up. "Wow! It's huge. She must have been really tall but with a great
figure." She laughed at the next item as she held it up for Jack to see.
"What's that?" He asked.
She stood up and giggled as she wrapped it around her waist. "It's a
small bustle," she said as she turned so he could see it poking out
behind her. "Extra padding to enhance the female caboose."
"I guess nothing really changes. Now women use tight pants and padded
bras," Jack said shaking his head.
"Yeah but it's a lot more comfortable than squishing your waist with a
corset and walking around with this thing poking out behind you. At
least this is a small one. Back around eighteen-seventy or eighty they
were huge and stuck out about a foot. This one was just a bit of an
enhancer," she said as she continued pulling out blouses with mutton
chop sleeves, long skirts, slips, nightgowns and other undergarments;
all of them high quality silk and satin. Then she came to a long formal
evening gown. She stood up and held it in front of her. It was
beautiful. It was all flowing draped folds and layers from the waist of
a pale blue ending at the hem with a wide white ruffle of lace. It was
trimmed everywhere with gorgeous white lace. It had a sort of square cut
neckline that would show ample cleavage with wide lace trimm over the
shoulders. The long sleeves ended with more wide white lace and it had
what looked like an apron around the waist but it was in the back and
hung over rear end with a large blue bow.
"Damn! She was a big girl. Especially for that time period. She must
have been five, nine or ten. About your height Jack. And by the look of
the corset and the bodice of this dress she had tiny waist and an ample
bust too," Sandy said as she moved over to Jack, turned the dress around
and put it up against him. "You know, as thin as you are, I bet this
dress would fit you perfectly if we used the corset."
"Well we'll never know because I'm not about to wear a dress and I
certainly am not going to be wearing a corset," Jack answered smiling.
"Now don't dismiss the idea out of hand, Jack. Halloween is coming up in
a couple weeks and we have to attend the annual executive Halloween
party. This dress would be an absolutely perfect costume. Who knows, it
might even win a prize."
"Fine. You wear it," Jack responded.
"I already have mine, you don't. I'm five foot six. This dress is way
too long for me but it should fit you perfectly."
"What about that "ample bust" thing you mentioned? I certainly don't
have that and I don't want to go out in public in drag. I'm no queer!"
Jack returned.
"Jack. It's a Halloween party. A lot of guys dress as women on
Halloween. I'm going as a high class call girl and you thought I looked
hot in my costume. Does that mean I'm actually a prostitute? Do you
think that's what I really am just because I dress as one for
Halloween?"
Jack knew he was between a rock and a hard place. "No. Of course not.
But I just wouldn't feel right or comfortable in a dress.. Everyone at
the party would laugh at me. A guy in a dress. I'd be embarrassed,
humiliated."
""Hmm. Okay. So it's a fragile male ego thing is it?" she asked.
"I wouldn't put it that way but if it works for you, okay, blame it on
my male ego," Jack responded a bit testily.
"So what you're saying is that you'd do it if no one at the party knew
you were a guy in a dress. Right?"
"I'd know."
"We weren't talking about you. You said 'everyone at the party' would
laugh. But if they didn't know you were a guy in a dress, they wouldn't
laugh, right? And if they didn't laugh at you then you wouldn't have any
reason to feel uncomfortable, embarrassed, or humiliated any more than
any woman wearing that dress would and your male ego would remain
intact. Right?"
Jack was getting a good dose of why Sandy was so successful in her job
as a contracting officer negotiating contracts with the people they did
business with. She was boxing him into a corner. He could feel the walls
getting closer but gave it another shot. "Yes. If they didn't know, that
would be true but there is no way that they wouldn't know. I'm five foot
ten. I have facial hair, a deep voice, no hips or butt, and a flat
chest. If you put me in a dress I would look like a guy in a dress.
There's just no way around that," he said confident that he had
presented insurmountable obstacles for her to overcome.
Sandy had a small smile at the corner of her mouth which gave Jack cause
to wonder if he was right. "First off, your just barely five, nine.
Second you shave once a week and even if you don't all you have for
facial hair is a light downy fuzz. Third, you voice is hardly what I
would call deep. I know women that have a deeper voice. With the right
tones, inflections, and breath, you'd have a beautiful sultry contralto
or alto voice. And fourth, women have been using strategic padding like
forever. Enhancing your figure to add what you lack is the least of the
problems. But let's not debate the fine points. Why don't we get down to
the brass tacks and..."
Her point by point breakdown hurt a bit. "Fine," Jack cut in. "And just
what are those brass tacks? I know you. I recognize your negotiating
voice. You have a proposal so get to it," he said. He had a feeling that
he was almost firmly lodged in the corner now. He'd been there before
and knew the feeling well. In his mind he thought, 'At this point it's
best to just quit arguing and let her present her proposal.' His mind
smiled as he thought, 'Yeah. And then I give her whatever she wants
every time.'
Jack leaned back against Sandy's workbench and waited. "You're right,
of course. What I propose is that you give me this week to make the
plans, put things together, and get you ready. You do as I say without
bitching or griping and then next Saturday we get you dressed up and see
how you look. You will cooperate with every step and when we finish we
will have three judges evaluate your appearance. You choose two and I
choose one. All five of us get one vote. If I'm right, you wear the
dress to the party. If you're right, we find another costume. That
weighs the vote in your favor with yourself and two friends to myself
and a friend. Does that sound fair?"
Jack stared at her thinking, 'Of course it sounds fair. She always
sounds fair but she always has a kicker in the deal somewhere that that
sneaks up and bites me in the ass. But I can't see it. I never can.'
"Okay. I agree that it sounds fair but you're devious and always stack
the deck in your favor. That's one of the things I both love and hate
about you. It seems I hardly ever win, and when I do, I get the feeling
that you planned it that way. Now who the hell am I willing to let see
me in a dress?"
"How about Bill and Todd?" she suggested. They were their neighbors on
either side. "I'll even give you Mary and Louise. You're way closer to
all of them that I am what with you working out of the house and me
being at work or on business trips so often. That gives you five votes
to my two. What the heck, I'll even give up my two votes. How's that for
a deal?"
Now Jack knew he was in trouble. She was seemingly giving him a
guaranteed out. 'How could I possibly lose if I have all the votes,' he
wondered. 'The only way is if she can actually do what she says and they
agree but I'm sure that's impossible.' "Okay. It's a deal."
Sandy held out her hand and he shook it sealing the deal. His gut
turned. He just knew he had been played but had no idea how or to what
extent "Great! Now help me pack everything into the house so I can sort
it out. I'll have to get the dress to the dry cleaners and wash and iron
the rest."
A little later Sandy left to take the dress to the cleaners and do some
shopping.
Chapter Two
Jack was busy in his home office working on another contract when Sandy
finally arrived home from work. She had called at noon and told him she
was leaving work early but would probably still be late because she had
a lot of stops to make on the way home. "I wonder what new torture she
has in store for me now," Jack said aloud smiling. He got up from his
chair to go greet her and wobbled briefly. He cursed under his breath
the high heels that Sandy had bought for him the night before. That
morning she had him put on a pair of knee highs and the black patent
pumps with the two inch heels. She told him he needed the practice
before Halloween.
Jack walked out to meet Sandy with the heels clacking on the hardwood
floor of the hallway. He met her in the entryway as she was hanging up
her coat. "Well, I see you're still wearing the shoes. How's it going
with them? You seem to be doing pretty good." She said as they moved to
the den.
"Oh just dandy. My calves are killing me, my toes are cramped and
smashed, and these damn stockings are pulling the hairs out of my legs.
Other than that, I just love them," he answered sarcastically.
"Well just be glad I started you with only two inch heels. I bought you
some three inch heels tonight for when you master those. The retro style
shoes I ordered for you to wear with the dress have three inch heels so
you'll be the right height. As for the cramps, you'll work through those
as your legs get accustomed to them. And, I told you to shave your legs
so don't whine about pulled hairs if you won't do as I say.
"You said no bitching or griping, so whining is allowed," Jack
responded with a smile. "Now what else have you got in those bags
besides shoes?"
"Just a few other things to help you practice and get used to moving and
functioning while being dressed as a woman."
Jack groaned. He had thought this whole thing was just for Halloween but
it was looking like he was going to spend the next several weeks
"practicing" for his role at the party. "Oh come on Sandy. This is
getting way to serious and complicated. It's just for a couple of hours
at a Halloween party."
"Now hold on Jack. I'm doing this for you. You're the one that said you
didn't want to be laughed at and that you wouldn't be comfortable in a
dress. I've thought a lot about that and realize that you were right. I
don't want you to be laughed at either and the only way to prevent that
is to make you comfortable while impersonating a woman."
"Okay, I can sort of see the shoe thing. I don't want to fall on my ass
at the party but other than these damnable heels, there can't be all
that much more to it. Can there? I mean what more could there be?"
"A lot! You have no idea," She replied. "There's a lot to learn before
you'll be comfortable and at ease. You've never had to manage a long
dress or skirt for starters. You don't know yet how to walk properly in
heels and the dress only complicates matters. Then there's sitting,
turning around with the train, going up and down stairs, going through
doors and getting in and out of the car. And then there's boobs. You
have to learn how to handle boobs..."
Jack cut her off with a lecherous laugh, "Heh, heh, heh. Oh I know how
to handle boobs. I'm really good at handling boobs as you well know."
"Mmmm. Yes I know," Sandy answered smiling. "But you've never handled
them from the other side, Dear. You're going to have quite a pair to
deal with. At least a very full C, maybe a D cup projecting out from
your chest. You aren't used to allowing for them like in tight spaces or
even raising your glass to take a drink. You'll suddenly find an
obstruction in your way."
Jack took a step back. "Now wait just a minute. You're not planning on
me wearing a long dress and falsies for the next two weeks, are you?"
"Very astute, Jack. That's exactly what I have planned plus a bit more.
Ever since we met I begged you to let that gorgeous hair of yours grow
out and you have but you always wear it in that darn low ponytail. I
want you to let it loose and learn to deal with long flowing hair about
your face, down your back and over your shoulders and chest. You have an
appointment for a trim, style and body perm tomorrow afternoon. After
the party you can go back to your ponytail with not much noticeable
difference."
"Whoa there. A perm? Are you serious? I don't want kinky, curly hair.
How will that not be noticeable?"
"A body perm, Jack. It just gives your hair more body and a bit of a
wave. Not curls. It'll be fine."
"I suppose there's more?" Jack asked worriedly.
"Just a few small things I have in mind," Sandy answered and Jack
groaned again. "Oh hush! It's nothing big but still you need to learn to
deal with it. While you're at the salon they will wax your legs, do a
manicure and pedicure and give you a nice set of acrylic nails. They're
also going to give you a complete make over and teach you a bit about
makeup and what colors you should wear. You'll need to practice doing
your makeup for the party so you can do touchups."
Jack backed up again and fell into his easy chair. "A few small things?
You call long fingernails, having my legs waxed and a makeover a few
small things? That's not small. None of this is small. By the time
you're done I won't know myself in the mirror. You're trying to make me
look totally like a woman."
"Exactly!" Sandy responded
"And how is this not going to embarrass the hell out of me at the
salon?"
:Well you know Janice that owns the salon, right? I talked to her and
told her everything and she understands what we're doing. She also
understands you don't want to be embarrassed so we're going tomorrow
because she is closed on Monday and Tuesday. It'll be totally private.
Isn't that perfect?"
"Look Honey, I love you dearly but this is getting out of hand. I don't
want to spend the next two weeks in drag learning how to be a female.
It's just a Halloween party. I went last year as a pirate. We can find a
different costume. Seriously Dear, I really, really don't want to do
this."
"But you agreed and we shook on it. That's like a promise," she pouted.
'Oh god! I hate it when she does that!' Jack thought. "But I really
don't want to do this." He repeted.
"Okay, Dear. I know you don't want to so I'll release you and let you go
back on your word," she said sullenly and still pouting. "We'll think of
something else."
At this point Jack felt like a shit. He knew he had shook on the deal
and he never went back on his word. His discomfort was turning his
stomach sour and he knew he wouldn't be able to live with this. Seeing
her like this and knowing he had let her down was killing him.
Sandy saw his discomfort and knew her words and actions were having the
desired effect. 'He's going to break. I know he's going to give in,' she
was thinking and she slumped her shoulders and turned to walk away.
"I'll go start dinner," she said and took a step.
"Oh jeeeze! Okay, okay! I'll do it! You're right! I gave my word and
I'll follow through."
Sandy straightened up and smiled. She had won again. "Yippee! Thank you
Dear. I know I can always count on you doing the right thing but
seriously, I will let you out of it if you really want me to." She threw
that in as an added guarantee. She knew he would reject it.
"No, no. I said I would do it and I will. Just do me one favor please?"
Jack asked.
"Sure. What?" Sandy responded.
Don't make a complete fool of me."
"I'd never do that Honey. Not a complete fool." She answered smiling.
"Now let's get dinner and then I'll tell you all about what I got for
you on the way home"
Jack and Sandy sat at the kitchen table eating dinner and discussing her
plans for the next few weeks and the party. Sandy itemized each of her
purchases and enthusiastically explained to a completely unconvinced
Jack why each one was necessary and would help him. He was not buying
it. "I know I said I would do this but I also think you are going way
overboard for a simple Halloween party."
"Okay Jack. I'll be completely honest with you. As you already know,
since I was promoted to the executive offices I have had to vastly
improve the quality of my wardrobe and upgrade my appearance. Last year
was the first time we were invited to the annual Halloween party and I
didn't realize just how much the quality of the costumes mattered. Our
"over the counter" pirate and barmaid costumes were far less than
acceptable and I was informed several times after the party to "up my
game" for next year. I've also been reminded several times over the last
few weeks."
"Damn! I'm sorry. I thought you looked great as an eighteenth century
barmaid. I guess my pirate outfit was a little cheesy compared to other
costumes I saw but I didn't realize it mattered."
"At the lower executive level 'Everything' matters. It's not just job
performance but also appearance, what clubs and organizations you belong
to, who you know and who knows you. There's a lot of pressure on stuff
like that. That's why when I saw that dress I was so excited. It's
unique and very high quality. It will be a standout at the party. And
that's why you have to be a perfect looking debutant from the eighteen
nineties, or at least as perfect as we can make you. I don't want you to
be a caricature of a woman in that beautiful gown."
"Okay. I understand. I promise to do my best and make you proud of your
husband, or wife, or sister, or whatever I am in that dress."
Sandy laughed, "After the hard time you gave me I should introduce you
as my sister or sister-in-law! It would serve you right. But seriously,
you'll be my husband and we'll amaze everyone at midnight. Now come and
see all the neat things that I picked up for you on the way home," she
said picking up the bags and heading for the bedroom.
When Jack finished clearing the table he went to their bedroom. Sandy
had everything spread out on the bed ready for him. "Now, because you
weren't with me and couldn't try everything on, you'll have to do it
now. I can return anything that doesn't fit. We'll start at the skin and
work out so strip."
"Naked?" Jack asked as he started taking off his shirt and kicking off
the heels.
"Yep. Now first, here are some CDs that I found online today. They had a
local supplier so I picked them up on the way home. They are
instructions on how to impersonate a woman's voice. tonal inflections
and mannerisms. There's five of them double sided and if you do one CD a
day you should be pretty fair by Halloween. You can even listen to them
while you sleep or work. At least that's what the sales literature
says."
As she looked up at Jack he was just dropping his boxers. "You always
could undress fast in the bedroom," she giggled. "Now put these on.
They're strategically padded panty briefs to give you a little help in
the hip and butt area. Oh, you also have to tuck little Jack back out of
the way between your legs. And I read online that his buddies should
tuck up into your groin and then the brief will hold it all in place."
As Jack struggled a but getting them on he said, "You read how to hide a
guys package online?"
"Yeah. You'd be amazed how much information there is about crossdressing
on line. That's good. Now stand up straight and let me put this around
your waist. It's a waist cincher and will give you a bit more curve."
"Damn, Sandy. That's tight!" he complained as she pulled the laces again
then tied them off.
She grabbed a tape off her dresser and wrapped it around his waist.
"Great! Twenty-five inches. We need twenty-four for the dress but the
full corset should do that easy. It's a good thing you're so skinny.
Your twenty-eight inch waist was easy to reduce. I was hoping to get
twenty-six tonight."
"I'm not skinny. I'm slim. And this thing is cutting me in half. Do I
have to wear it?" Jack asked with a grimace on his face.
"Yes. It's the only way to fit you in the dress."
"So now what?" Jack asked fearing the answer.
"Put your arms out," Sandy said as she picked up a bra and slid it up
his arms. He groaned again as she fastened it behind his back. She
picked up a box and opened it and as Jack watched, she pulled out... a
breast! And then from another box, another breast. She carefully
inserted them into each cup of the baa and stood back to have a look.
"They look great. Perfect fit. They can be attached to your chest with
adhesive but not now. Maybe after Janice is done with you tomorrow."
"Attached? To my chest? I can't go around for two weeks with these
things stuck to me. Let's forget about the glue."
"Okay Honey. For now. Here, put on this slip." She watched as he put it
over his head and let it fall down to his ankles. She smoothed it and
adjusted it around his waist as Jack ran his hands over the smooth nylon
material and smiled. "Feels nice, huh?" Sandy remarked smiling. "Here,
put this on now." She said as she handed him a long sleeved white silk
blouse. "I tried to get things that were close in type and style as what
was in the trunk. All of them are at the cleaners but you should be able
to wear them after I pick them up."
Sandy watched and smiled as Jack fumbled with the small pearlescent
buttons. "Here. Let me do that. You're not used to such small buttons
and on the opposite side too. Okay. Now for the skirt," she said as she
finished the four buttons on each cuff. "Put your hands up and slide the
skirt down to your waist."
Jack did as she said and Sandy fastened the hook and button at the back
and then zipped it up. "A perfect fit," she proclaimed as she checked
the length and waist. Then she wrapped a wide leather belt around his
waist and kneeled on the floor to help him with his shoes. She slipped
on some stocking material booties and then the shoes. "These are called
peds. They're for when you're not wearing pantyhose or stockings. You
still need something on your foot. I'm trying the new three inch heels
to see how you do with them. Alright. Now sit on my vanity stool while I
brush out your hair."
When she finished with his hair she removed the small studs that he
usually wore in his ears and put on a pair of inch and a half gold
hoops. "Okay. Now stand up and do a slow turn and let me check you out."
Jack stood up carefully and walked a few steps into the middle of the
room and did a slow turn. Sandy smiled. "I think this is going to work
out just fine. You look fantastic and we haven't used makeup or done
your hair yet. Take a look at yourself," she instructed as she pointed
towards their mirrored closet doors.
Jack turned and looked. He was stunned for a moment then took a few
steps closer. He stared at his reflection for a bit and then turned from
side to side. He finally turned around and looked over his shoulder. "My
god Sandy. Except for my face I look like a woman. I have curves. You
were right about that strategic padding. Holy shit! This is scary."
What Jack saw was a woman with a great figure dressed in a a classic
styled long sleeved white silk blouse that draped her ample breasts. She
wore a dark blue floor length A-line skirt with a wide leather belt that
emphasized her small waist and wide hips. Her long flowing hair fell
over her shoulders and came to rest atop her breasts. Even his face
seemed to take on a somewhat feminine appearance.
"You do look good Dear, and don't worry about your face. Janice will
take care of that tomorrow. We'll dress you the same way tomorrow
morning. I'm taking off at noon again so be ready to leave here by one
o'clock."
"I'm not going there dressed like this am I?"
"Of course you are. You just said you look like a woman and when you
leave the salon you will definitely look like a woman from head to toe,
literally. You wouldn't want to leave there in your male clothing, would
you?"
"No. I guess not."
"Right. Now let's go watch TV for a bit before bedtime."
Chapter Three
The next morning Jack took a shower and used Sandy's shampoo and
conditioner as instructed, Sandy blow dried his hair back brushing it
while he was bent over. "This will give your hair a lot more fullness
and body and it will flow better. You need to get used to dealing with
it loose." She explained.
She dressed him in the same outfit as the night before and reminded him
that she would be back early to take him to the salon to see Janice.
When Jack saw himself in the mirror with his hair full and flowing over
his shoulders and down his back he came to really believe that she could
pull his off. His face had become only a minor distraction on an
otherwise totally feminine appearance.
They had breakfast together and Jack began to realize what Sandy meant
when she spoke about learning to deal with his hair being loose. He was
annoyed that he had to keep brushing back over his shoulder th keep it
out of his face and his food. Sandy laughed and told him, "You'll get
used to it Dear. Just watch me and other women and copy their actions.
Soon you won't even notice yourself doing it."
Jack spent the morning working on some of his contracts and dealing with
his hair, the long skirt, the heels, and the boobs. When Sandy got home
she asked him how his morning went. You don't really want to know," he
replied.
"Of course I do. I want to help you work through all of your problems.
After all, I have a lifetime of experience to share with you."
"Okay fine. You asked for it. The hair is a pain in the ass. It's always
falling in my face as I work at the computer. These tits get in my way
and block my view of the keyboard. This skirt is a pain too. It gets
hung up on everything as I walk and when I sit the chair wheels roll
over it plus it gets all bunched up under my ass. And speaking of my
ass, I feel like I'm sitting on a pillow and it pokes out and hits the
back of the chair. And that brings me to another point, namely my hips.
They barely fit in my office chair. So, is that enough?
Sandy was laughing almost uncontrollably. "Oh you poor dear. You've had
a female life thrust upon you without the advantage of a lifetime to
grow into it. But don't worry. We all deal with those things every day
and I'll teach you how. Just a couple of pointers for now and then we
have to get going. I've seen you at your desk. You're always hunched
over your keyboard so naturally your hair will fall in your face and of
course your breasts will block your view. That's why women sit up
straighter. Try it. You'll see the difference. Okay, so lesson one
complete. Grab the purse I gave you this morning and let's get out to
the car. It's best if I drive or you be having another new experience;
driving in heels." At the car, Sandy had to instruct jack on the fine
points of entering and leaving a car in a skirt.
They arrived at the salon on time for Jacks appointment and Janice
greeted them at the door. Once inside she locked the door and turned to
look at Jack. "Damn Sandy. You said he looked good and you weren't
kidding. Okay Jack. Into the back and remove everything but your
panties. We'll start with the waxing and get the bad part out of the way
first."
In the back room, Jack stripped down with Sandy's help and then Janice
did a once over. She checked his face, back, chest and abdomen,
underarms, and legs. Jack was totally embarrassed and could feel his
face getting hot. "Well this is going to be easy. This isn't meant as an
insult Jack, but you're almost as hairless as a ten year old. I have a
facial depilatory that will take care of that fuzz. It should last about
a month. If you keep using it the hair will quit growing back after
three or four months. Then you'd never have to shave. Okay, now get up
on the table face down."
During the next half hour, Jack had what little hair he had on his legs
ripped out and had the downy fuzz on his face removed and his pits
denuded after which Janice told him put on a robe and move to a chair at
the back of the main salon.
"Ya know guys, I think I've had enough. This is beginning to seriously
impinge on my manhood. I mean, in my teens I was embarrassed by my lack
of body hair and now in a short time you've removed what I spent a
lifetime growing."
"Oh sweety. It'll grow back. Besides, do you know how ridiculous that
sounds? You saying that you're upset because becoming a woman is
impinging on your manhood? Of course it is. Now just sit down and let
Janice do her thing."
Jack sat and the chair was leaned back and his neck was fitted into a
cutout space in the sink and Janice washed his hair. He immediately
relaxed as the warm water and her long nails massaged his scalp. "Now
this I could get used to," he told her. When she finished she wrapped a
towel around his head and raised the chir back.
"Okay. Now come with me to my station and let's get started on you."
Jack sat in her chair and she draped a cape over him and fastened the
Velcro tab around his neck. She removed the towel from his head and
started to comb out his hair. "Sandy said you had nice hair and she was
right. It should be truly beautiful when we're done. Now just hold still
while I fit this cap on your head."
"What's that for?" Jack asked.
"Well, your hair is a beautiful chestnut brown but is rather monotone.
I'll pull a few strands of your hair through these holes and then use a
some medium blonde color on them. Then when your hair is done you will
have what looks like natural blonde highlights. It's totally natural
looking unlike the ones done with the foil strips which leave wide
blonde streaks in your hair."
"Blonde highlights? I don't know about that. Can we just skip this part?
Where's Sandy?"
"Sandy had some shopping to do and no, we can't skip it unless you want
to explain to her why. Besides, after Halloween I can always dye the
highlights back to your regular coor if you want."
Jack thought about it for a bit as she started to pull strands of hair
through the holes. He decided that as long as she could undo it
afterwards, it was better to just go along than to have to explain his
reluctance to Sandy. "Okay. Go ahead," he said.
"I thought so," Janice said smiling. "Trust me. You'll love it Jack."
And she continued until she had hair pulled through all the holes and
then she applied the blonde coloring to his hair. After it finished
working she rinsed it out and removed the cap and then fixed the color.
Afterwards she put his hair in rollers and added the perming solution.
Then she wrapped his head and led him to the dryer. "With that head of
hair you have, this is going to take a while so I'll do your nails. Just
lean back, close your eyes and relax while I work." Jack did just that
and had soon dozed off into a half sleep.
When the timer went off, Janice lifted the drywer hood and checked his
hair. "Good. Looks like your done. Let's go over to the wash chair and
I'll rinse the solution out." She rinsed and neutralized the solution
and then took out the curlers and tok him back to her station.
As he sat down he noticed a strangeness in his fingers. His nails
specifically. He pulled his right hand from under the cape and looked at
the long nails on his hand. They all extened a quarter inch past his
fingertips and were a super high gloss dark red. "Holy shit! What'd you
do to my nails?
"It's the latest in acrylic nail technology. They are virtually
unbreakable and are bonded to your natural nails so there's no chance of
fungus or infection between the acrylic and your nails."
"How do I get them off?"
"You don't. They're permanent. You have to wait for them to grow out but
after Halloween I can remove the polish and file them back to your
normal length so don't worry. Now relax while I put the larger curlers
in your hair."
"Sandy said it wouldn't be a kinky curly. It won't, will it?" Jack
asked.
"No. This is just a body perm not the heavy duty perm you're thinking
about. This will just give your hair more body and a soft natural wave."
When she finished she said, "Okay Jack. Time for the dryer again. This
time I'll do a pedicure so just go ahead and relax again."
Some time later she shut down the dryer again and tested his hair.
"Great Jack! Back to the other chair."
"This is like musical chairs," Jack said as he glanced down at his feet
and saw the ten dark red toenails. He let out a sigh and thought, 'Well
at least they're not longer.'
He sat at her station again and she told him, "I'm going to work on your
face while your hair cools down so I'm going to lean the chair back a
bit. I'm going to explain every step and show you what I'm using so you
can practice between now and Halloween. Sandy wanted you to be able to
do this pretty much by yourself so you can do touchups alone at the
party but first I'm going to clean up and neaten you brows."
Janice started plucking his brows and he got worried again. "Hey! Take
it easy there. You can't fix them if you take off too much."
"Relax Jack. I;m just cleaning up stray hairs and shaping them a bit."
When she finished she said, "Okay Jack. Listen carefully and try to
remember as much as you can. What you forget, Sandy can help you with
but you need to know this. I'm using colors to compliment your skin
tones and will give you everything I use to take home with you."
She then carefully explained every step from blemish cover to foundation
and blush. Then lip liner and lipstick and on to his eye shadow,
mascara, and eyeliner finishing with the eyebrow pencil. Jack was
completely confused. "I'll never remember all that," He said.
"Don't worry. Sandy will be teaching you every morning and on the
weekends. You'll be good enough to hold your own at the party. Now we'll
sit you up for one last thing before we take your hair down."
"There's more?" Jack asked.
"Yes. One more thing. Sandy wants me to pierce your ears."
"My ears are already pierced. She conned me into doing it when we were
in college."
"Well now she wants them pierced again for the party. She said that you
can just take them out afterwards and they'll heal up but for the party
she wanted them pierced again."
Jack let out a large sigh and groaned, "What the hell! With all the rest
you both are doing to me what's two more holes in my ears," but he
wasn't prepared for the second sting in his right earlobe. "Hey! How
many are you doing?" he asked.
"Just two more in each ear." She said as she did the same to his left
earlobe. "There. That's done. Now we'll get those curlers out of your
hair."
After removing the curlers she brushed out his hair and trimmed a few
places and declared him complete and removed the cape. Just as he was
about to get up and look in the mirror, Sandy came through the back door
carrying several bags. "Don't look yet Honey. I want to get you
completely dressed before you see the finished product. Come into the
back room."
Jack swore under his breath but followed her into the back wondering
what she had in the bags. He tried to get a quick glance in some of the
other mirrors in the salon but they were all at the wrong angle.
In the back room Sandy explained, "Alright Jack. First thing is to lay
face up on the table again."
"No more waxing! I've had it with that."
"No dear. Janice is going to attach the breast forms with adhesive and
use makeup to hide the seams. That way you can get used to the feel and
weight on your chest."
"Glued on? For how long?"
"Until you see Jenny, my daughter, on the day of the party. She is going
to make you an appliance that will look totally realistic for
Halloween," Janice said as she removed his robe and guided Jack to the
table."
"Your daughter is in on this now? Pretty soon the whole town will know.
Why does she have to know?" Jack asked.
Sandy smiled and said, "Jenny is a professional makeup artist for TV and
the movies. She specializes in making appliances to make the actors look
like monsters and zombies and such. She's going to measure you this
weekend and then make an appliance that will make your breasts look so
totally real that even you won't be able to tell they aren't real. These
forms are good but hey won't bear close scrutiny and I guarantee that
the guys at the party will be giving them a lot of close scrutiny."
"Oh joy. Now I'm going to have guys ogling my boobs. Wonderful."
"Welcome to our world, Jack," Janice said giggling. "Now up on the table
and lay down." She then carefully cleaned his chest and then located and
marked the placement of the form and glued them in place while working
the edges down. After they had set she applied a long lasting theatrical
makeup. "This stuff wil last for several weeks and you can shower, swim,
or hot tub with no problem. Okay, you're done. Now Sandy can get you
dressed."
Sandy got up from her chair as Janice left the room. Okay Honey. I heard
you loud and clear earlier about your clothes, hair, boobs an so on. I
already told you that if you stand and sit straight, it will minimize
those problems but I can also tell you that with boobs your size, forget
about ever seeing you feet other than in a mirror," she said with a long
giggle. Then continuing, "As for the long skirt, I did some shopping and
bought you some knee length skirts and a couple nice dresses. I hope
they fit okay. I think you'll like them. You'll still have to practice
with the long skirt but these will give you a break now and then."
"The liking is all relative. Frankly I don't 'like' any of this but
you've got my word until after Halloween so let's see what you have."
She handed him a pair of pantyhose and instructed him on putting them
on. He was surprised at the different feel now that his legs had been
waxed and moisturized. "Wow. Now that feels different."
"Kinda nice, huh? Try running your hand over your legs and then rubbing
your legs together," Sandy suggested.
"Mmmmm. Yeah that's nice too. So now where?" Jack asked.
"The waist cincher."
Jack groaned. "Do we have to? Couldn't you have bought larger stuff so I
wouldn't have to wear that damn thing?"
"Nope. We need to train your waist and you need to get used to the
restriction. Now turn around while I tighten it." She pulled and Jack
grunted and groaned until she tied off the laces. "Now you can handle
the rest. Put on the bra, blouse and then your skirt and shoes that I
have laid out over there. The skirt is lined so you don't need a slip."
Jack was struggling with the bra until Sandy stepped in and helped him.
"Thamks. I'm not used to these things being attached and my arms don't
bend around my back like yours do."
"That's okay Honey. You'll get used to it pretty quick. And they're not
"things." They're your breasts. Okay, now here's your blouse."
Soon Jack had the white cotton long sleeved blouse on and stepped into
the knee length black pleated full skirt. Then he slipped his fet into
the pair of black pumps with a three inch medium heel. "Is that it? Or
do you have more surprises in store for me?" Jack asked.
"Oh there are definitely more surprises for you but that's it for
clothing right now," Sandy said as she stepped closer to Jack and
fluffed his hair a bit and smoothed his skirt. "There. You look
fantastic! I think it's time you got a look at yourself." She took his
hand and led him back into the salon. "Okay. Close your eyes and I'll
guide you. I want this to be a complete surprise when you first see
yourself."
Sandy guided Jack over to a triple paned full length mirror and Janice
stood next to it with her camera at the ready. Sandy positioned Jack and
said, "Alright Honey. Open your eyes."
Jack opened his eyes and his first reaction was to look around for his
reflection. (flash) That was when it hit him that the woman in the
mirror was mimicking his movements. Her head was twisting from side to
side and her long waves of hair were flowing back and forth in time with
his motions. (flash) That's when he stopped searching and just stared.
He looked at what she was wearing and confirmed that it was his
reflection and his mouth dropped open. (flash) "Oh my god! What have you
done to me!?" he asked. And Janice's camera flashed again.
"You're a knockout Honey. You have an amazing figure. You're going to
look amazing in that dress on Halloween.," Sandy enthused.
Janice stepped closer and said, "You really do look good Jack, or should
we call you Jackie now? Your facial features are a tiny bit broad but
they still fall within the normal bounds for a woman. With a nose job,
brow lift, cheek and chin work you would be gorgeous. But with makeup I
was able to compensate for most of that and Sandy can show you how to do
it."
"Ah, yeah, thanks... I think. And it's still Jack and always will be.
This is just until Halloween."
"Well I have one more gift for you. Actually it's from my daughter.
Close your eyes and open your mouth. Okay, now take a deep breath in
through your mouth," Janice instructed. As Jack breathed in she sprayed
into his mouth from a small canister like a breath freshener. Jack
choked and gagged and was about to speak when she put her hand gently
over his mouth and said, "Don't say a word until I tell you. This spray
will temporarily raise the pitch of your voice by tightening you vocal
chords. It lasts about eight to twelve hours and then you can use it
again. I gave Sandy six more for you. Okay, give it a try. Say
something."
Jack cleared his throat and said, "That tastes like... Holy shit! My
voice! I sound like a girl! You're sure this is temporary, right?"
"Absolutely. And with those voice CDs Sandy told me about to help with
your inflection and vocabulary, you should sound about perfect by
Halloween."
"Oh Honey you sound wonderful. No one will ever guess you're anything
other than a genuine woman. Now we have to get going. Thank Janice and
I'll help you on with your new coat."
Jack turned to Janice and said, "Thanks, Janice... I think," and turned
to see Sandy holding up a long coat for him. He sliped into the coat and
Sandy told him to put his hands behind his neck and pull his hair out
from under the collar as she demonstrated the action. He did and she
buttoned the coat and did up the belt around his waist and then handed
him his purse.
"Okay. Now hook your thumb under the strap and hold your fingers up like
this," she instructed demonstrating with her own purse. "Now put the
strap over your shoulder while sweeping your hair out of the way with
your fingers. See? That keeps you from getting your hair caught under
the strap."
Jack followed her instructions and the turned to the mirror again to
stare at the young woman standing there in her coat with her purse slung
over her shoulder. He was impressed with his appearance but scared at
the same time. Between the two of them, Sandy and Janice had made all
vestiges of his male self disappear and created this good looking woman.
A thought ran through his mind, 'If it was that easy to make me look
totally like a woman, how much did I look like a man to begin with?'
Sandy broke him out of his thoughts when she took his arm and said,
Alright Jackie. It's time we got going and let Janice go home." She
turned to Janice and said, "Thank you so much. You did a fantastic job
on Jackie."
"It was a pleasure. I'll see you both again on Halloween when we do your
makeovers for the party. And don't forget, Jenny will be at your place
this Saturday to measure and mold Jackie for her appliances so she can
have them ready for the party. Good luck you two."
Chapter Four
Jack and Sandy left the salon but instead of going to their car parked
in front, Sandy steered Jack down the sidewalk. "What are you doing? The
car's right there."
"It's dinner time. We're going to Guido's. I feel like some Italian. My
treat."
:Are you nuts? I can't go in there like this."
"Like what?"
"Like this!" he said indicating his clothing. "Dressed like this. Like a
woman."
"Jackie. You saw yourself in the mirror. You heard your voice. If it
looks like a woman, walks like a woman, and talks like a woman, what
will people think it is? Now relax. You need the exposure so you act and
feel natural on Halloween."
"Argggg! You're killing me here, Sandy! Okay. Fine. Let's go."
"Just remember to do the things I've told you. Small steps, smooth your
skirt when you sit, smile, speak softly and watch me. Try to copy my
actions."
Halfway down the block they reached Guido's. As they entered the lobby,
Sandy removed her coat and draped it over her arm. Jack followed suit
switching his purse from one hand to the other just as she had done. The
hostess greeted them and Sandy asked for a table for two and they
followed her to the table. He watched Sandy's every move like a hawk and
did his best to imitate her movements. "You're doing great Honey but try
to not stare at me so hard. Be more relaxed and casual. You'll draw less
attention," she said quietly.
"Relaxed and casual!" Jack said in a strained whisper. "I'm a guy
sitting here in a restaurant with a bazillion people all around me while
dressed in a skirt and blouse and wearing makeup and you say to relax?
I'll be lucky if I don't have a heart attack!"
"Calm down! Or do I need to slap you like the hysterical woman your
acting. Take a deep breath and look at the menu. The waitress will be
here soon and you need to order."
Jack took that deep breath and several others and did eventually calm
down a bit and by the end of desert he was actually beginning to enjoy
himself. Sandy's casual banter about their plans and the meal helped to
distract him. He was even able to follow her to the ladies room to
freshen up after the meal. The fact that no one seemed to notice
anything out of place did a great deal to bolster his confidence and it
showed in his more relaxed demeanor. He realized that Sandy had been
right and that he did look good enough to pass in public. But he still
didn't like it. Not one bit.
Back at home he spent the rest of the day dressed and tried to do a
little catch up work for his time lost that afternoon. The long nails
drove him crazy when he used the keyboard but Sandy helped when she told
him to use the tips of his nails. It worked but was still a bit awkward.
"You'll adjust to it, Daer."
After dinner, Sandy led him to the bedroom where she revealed some more
of her shopping purchases. "I thought that you might like this. It will
sort of keep you in the right frame of mind all night," She said as she
held up a baby blue satin nightgown with white lace everywhere.
Then she pointed to the bed saying, "I also bought you some nice satin
panties to sleep in and a robe and some mules with a short two inch heel
that match the robe. Aren't they beautiful?"
"Yeah. Beautiful. But you're getting way too carried away with this
whole thing. You must have spent a small fortune buying all this stuff
today not to mention the salon trip and just exactly what is Janice's
daughter going to cost? For crying out loud, Honey. It's a freaking
Halloween party! Even if it is an executive competition thing. All this
money for what? Clothes and shit that I'll never use or wear again."
Jack complained.
"I really haven't spent that much. Not when you consider that some of
the other costumes at the party will cost upward of a thousand dollars
or more and we got the dress for free. And who says you'll never wear
them again? I really enjoyed lunch with my girlfriend today. Maybe we
could do it again every once in a while," Sandy said with a big smile.
"Oh no. Not happenin'.My promise ends when we get home after the
Halloween party and I can guarantee you that I will never let you wangle
me into anything like this again. Ever!"
"We'll see what the future brings. But for now, strip and put everything
on. Then we'll get that makeup off your face and have a nice night
drinking some wine and watching a movie I picked up. And then, who knows
what might happen."
The rest of the week went as well as can be expected. Sandy went to work
and Jack worked on his contracts, albeit rather uncomfortably. Even
though Sandy had bought him shorter skirts, she insisted that he wear
the long ones during the day as 'practice' for the party. Plus he was
still dealing with the long hair and breasts, although more
successfully, and with the long fingernails. He was also having to deal
with the restriction of his waist, which Sandy had tightened down to
twenty-four inches by the end of the week.
On Saturday just after lunch, the doorbell rang, and without thinking,
Jack answered it. By the time he was standing with the door wide open it
was too late so he just said, "Can I help you?" to the young lady
standing on the porch.
She smiled and put out her hand and replied, "You must be Sandy. I'm
Jenny. My mom told me about your husband and I'm here to get
measurements to make his appliance for the Halloween party."
Jack was a little flustered that she thought he was Sandy but let it
slide and said, "Oh, yes. Please come in." After she was in he guided
her to the kitchen as she requested and then he called out for Sandy.
"Honey. Janice's daughter is here. We're in the kitchen."
When Sandy walked in and introduced herself, Jenny was visibly confused.
"You, you're Jack? That's amazing. I'd never have guessed and I spend my
days making people look like somebody or something else. Wow! You're a
natural."
Jack wasn't sure whether to be pleased or upset so just responded with,
"Thanks," and a smile.
"Well. I best get started," Jenny said. "You should strip to the waist
so I can get a look at what I'm dealing with. I'll get my stuff set up
here on the table." Jack reluctantly unbuttoned his blouse, removed it
and stood there for a bit. Jenny looked up and said, "Bra too honey. I
can't make a form with it on." After he removed his bra she checked him
out and held up some color swatches to match his skin color then said,
"Great. We can leave the forms on. Mom did a great job. You can go to
the bedroom while I mix up a few things here. Spread this plastic sheet
on the bed and lay down. No pillow. I'll be right there." Jack nodded
and she handed him a large plastic sheet.
Jack grabed his clothes and the sheet and went into the bedroom to wait.
Jenny was soon there with a large pail. She rubbed something all over
his chest she called a release agent and the started to put plaster in a
thick layer all over his chest and up over his shoulders and the front
of his neck. She then laid a layer of what looked like a gauze cloth on
it and started in again with the plaster type stuff. When she finished,
Jack had over an inch of the stuff on his chest.
"This won't take long. It sets up hard as a rock in about ten minutes.
Then I'll lift it off and you can clean up and get dressed. I'll use
this as a form to make your chest appliance that I'll put on you on
Halloween. No one will ever know it's not all you," She said smiling.
After Jenny left, Jack was cleaning up when Sandy came in and said, "I
laid out some clothes on the bed for you to put on when you get finished
there."
"A different outfit? What for?" he asked.
"We're going out to dinner."
"Do we have to? I don't relly feel all that comfortable going out like
this."
"My point exactly. You need to get comfortable before the party so get
dressed. And if you're a good girl I'll let you take me to a movie too."
When Jack glanced at the bed he saw a black dress and it didn't look to
him like there was very much to it. "Isn't that a little bit ahh... Well
it doesn't look big enough. I mean like there's not much to it."
"Every girl need an LBD Dear. A little black dress. And this is yours.
Can you believe I found it in Goodwill and it still had the sales tags
on it! It's brand new and in your size for only six dollars!"
"Okay. That's it. I know I promised and said I would go along with your
crazy scheme but that didn't include a little black dress. I'll go out
tonight but in a normal skirt and blouse. Okay?"
"At least try it on. You'll see it's a very modest LBD. The hem is only
a few inches above your knees and the top has cap sleeves and shows very
little cleavage. It's quite modest and proper for a night out to dinner.
Please?"
"Alright. I'll put it on but I'm not going out," Jack said as he removed
what he had on and started to get dressed. He put on the black lace
trimmed panties over his padded brief and then rolled the shear black
stockings up his legs. Sandy helped him with the garter belt and to
attach the tabs to the stockings. Then he put on the waist cincher and
she tightened the laces. Then came the black lacy bra that matched his
panties and then he let Sandy help him into the dress.
She zipped it up the back and handed him a pair of patent leather
stilettos with a four inch heels an ankle straps. "Here. Put these on
and then we'll do your hair and makeup."
After jack put the shoes on he sat at the vanity, Sandy draped a cape
over his shoulders and pulled his hair back. She removed his makeup and
then started to reapply a much more dramatic look with dark eye shadow,
heavy mascara, and full red lips. Then she did his hair in a semi-updo
with strands strategically left loose and hanging down that she used her
curling iron on. A pendant necklace, dangling earrings, a bracelet and
several rings and he was finished.
"Alright Honey. Stand up and take a look in the mirror."
Jack walked a bit unsteadily in the new heels but made it to the
mirrored closet doors and stared at himself. He turned from side to side
and smoothed the skirt of his dress. He played with the curled strands
of hair and checked out the exposed portion of his breasts. "Damn! This
is amazing... and scary as hell."
"why scary? I think you look wonderful. Very pretty. That dress shows
off your figure and legs beautifully."
"That's it. That's exactly what's scary. God Sandy, I look in the mirror
and I can't tell that I'm not a woman. With the other clothes they
covered enough that it never really... well I never really looked so
totally..."
"Like a beautiful woman?" Sandy finished for him. "That's what I wanted
you to see Dear. You have no need to worry about going out and you can
see that the dress does not over expose you and the skirt is flirty but
plenty long enough for modesty. I dressed while Jenny was working on you
so grab the clutch purse on the bed and we'll get going. I made
reservations."
It was at that point that Jack first noticed that Sandy was dressed
similarly and was looking totally hot. He was defeated and outmaneuvered
again so he silently picked up the purse and followed her to the front
door but when they reached the living room he was shocked when a group
of voices all shouted out, "Surprise!" It was their neighbors, Todd,
Louise, Bill and Mary. Jack was dumbstruck.
Bill was the first to speak. Looking at Sandy he said, "Is that Jack or
did we ust blow the surprise? Cause if it is Jack, he just lost the bet
big time."
"Oh it's Jack alright. Or maybe Jackie until Halloween. Depending on
your votes," Sandy answered with a smile.
"Damn dude. You look so fuckin' hot. I'm afraid you just lost my vote,"
Todd said
Bill spoke up again, "Hell yeah. Shit man, I came here to vote for you
but there's no fuckin way I could get away with it. You're one hot piece
of..."
"Enough Bill!" Mary cut him off. "Watch your mouth! There's four ladies
present and we don't need to hear your foul language." She turned to
Jack, Sandy and Louise, "Sorry girls, and especially you Jackie, but you
know Bills mouth."
Jack knew Sandy had set him up with the makeup, hairstyle and especially
the dress and heels. He knew he had lost any chance of getting out of
wearing the old dress to the party so he gave up gracefully. He smiled
and said, "I guess I'm going to te Halloween party in a dress."
"Damn! You even sound like a chick," Todd said and everyone laughed.
They all talked for a while and then Sandy announced that they had
reservations. "We'll be late if we don't get going. See you all there."
"Everyone's going?" Jack asked surprised.
"Yep. It's Jackie's birthday," Sandy answered.
"Oh well. They say misery loves company. Let's go," Jack said smiling.
They put on their coats. Jack remembered to remove his hair from under
the collar and check himself in the mirror. He just shook his head and
followed Sandy out to the car. He found that the four inch heels weren't
all that bad after wearing the three inch ones the last three days.
They had a pleasant evening for the most part. Jack did feel a bit
uncomfortable with his buddies and some of the guys in the restaurant
giving him the once over but reasoned that in their shoes, he would be
doing the same thing. He decided that this was just something that women
learned to live with and he thought, 'And what the hell, as long as they
are leering and not yelling about a man in a dress, I guess I look
pretty good.' It was a definite boost to his confidence, if not his male
ego, which was Sandy's plan all along. She knew that if all went well
and she could make him feel comfortable, it would make her plans for
Halloween work out perfectly.
After dinner their friends left for home and Sandy and Jack went to the
movie which was anticlimactic after everything else that happened. Sandy
was very pleased when Mary and Louise had confided in her that Jack was
amazing and that his voice and mannerisms were almost perfect.
So, after the surprise party and their night out it was very little
problem for Sandy to get Jack to go out shopping at several outlet malls
and stores on Sunday and during the rest of the week. She even convinced
him to do the grocery shopping and do a few errands like picking up the
dress at the cleaners. It all provided more training and she was sure he
would do great on Halloween.
On Saturday he went to an appointment at the salon and Janice touched up
his hair, hails and another waxing, just to be sure," and more beard
removal cream. She generally checked him out completely o make sure he
was ready for Monday night. Sandy took Monday off to prepare and to be
there when Jenny showed up to do the final fitting of his appliance for
the party that night.
The house was awhirl with activity. The dress and all accessories were
brought out. Jack took a long hot bubble bath with sweet smelling bath
salts and Sandy powdered him with similarly scented talc and had him put
on his padded panty briefs, robe, and mules. He was declared ready just
as Jenny rang the doorbell.
They went to the bedroom where Jenny once again laid out the plastic
sheet on the bed and had Jack remove his robe and lay down. She removed
the forms and cleaned his chest, sides and back with alcohol wipes and
then laid the appliance on his chest. She carefully marked the boundary
and then removed it and applied an adhesive. After a few minutes it
dried and she had him roll over and marked his back and applied more
adhesive.
She explained that the appliance already had adhesive on it as she
pulled a thin plastic sheet from the back. Then carefully, starting at
the marks on his side, she worked her way across his hips over his
waist, up his chest and over his shoulders and then around his neck.
Jenny then had him roll over and worked across his back at his waist and
up to mid back. After that she pushed and poked all over until she was
satisfied and then worked the edges. After sealing the seams and
blending in the edges with makeup she declared him finished and had him
sit up.
As Jack sat on the edge of the bed he glanced in the mirrors and was
shocked once again. The forms had looked okay but this was unreal. The
skin tone was a perfect match and the breasts looked totally real. As he
sat there he began to feel a tightening sensation around his waist. It
was like the waist cincher crushing his middle. He put his hands to his
sides and looked up at Jenny questioningly.
"Getting a bit tighter?" she asked grinning.
" No shit! It feels l