Summer student ? by: Jennifer Stewart
Chapter 1 - A Money Making Proposition
Billy Chambers was a 19 year old student in the Department of Physics at
Stanford. He was exceptionally talented and, would begin postgraduate
work at an important national laboratory in two months time. His career
was on track but he was wretchedly poor and had few prospects of raising
his income to the point where he could enjoy some of the comforts of life
that he had enjoyed when living at home.
Billy's sister, Anne, was two years older. She had graduated from the
College of Arts and was expected to do brilliantly as an actor. However,
at this stage of her career she too was desperately poor. Billy and Anne
had received money towards their living and tuition costs from their
mother but she was now dead and, unexpectedly and disappointingly, she
had left debts rather than assets. It was a difficult situation and, on
the afternoon that the will had been disclosed, they sat together in a
small French restaurant finishing a bottle of Chateauneuf du Pape, they
speculated about their financial prospects for the foreseeable future.
"Okay, your scholarship will only take care of tuition, and I can scrape
by on my pay for the next three months run of the play, but what happens
when the run ends?"
"I hate to get a job. The first year at the lab will be really tough. If
I have to sling hamburgers or work in a bar to live I will never be able
to handle the workload. Mother was giving each of us a $1000 a month.
That's a lot to replace. What on earth was she living on herself?"
"I think it's obvious that she was literally starving herself to support
us."
"Poor mom. Well we have to come up with a way of making an extra $1000 a
month each. At least you can sell your body," said Billy, giggling.
"I know. I've thought about it."
"Anne! I was kidding."
"I know you were but it's not such a silly idea. I like sex and I have a
friend who works for an upscale escort agency. I think she could get me
in."
"Anne, I don't think you should do that. It's dangerous."
"Steph' said that this is a well run agency and the clients are very
carefully checked. She has never had any trouble. She says she enjoys the
work and the pay is fabulous. I could help you out until you get
settled."
"Anne! I would be living off the 'wages of sin.' I mean that
metaphorically but still, what kind of a shit would that make me."
"Oh, stuff the morality. We have a serious cash problem and we have to be
pragmatic about it. After a year at the lab you'll start to make some
decent money - but only if you do well. I am sure I can make enough from
the agency to support both of us comfortably."
"I don't know what to say. Ethics aside, I am really touched that you
would do that for me." I leant over the table and kissed her.
"I'll find a way for you to pay me back."
Billy knew that was not intended as a threat.
Three weeks later they met again in the restaurant. Anne was in the
agency and starting to make money.
"I make $600 for every hour I spend with a client and its straight cash.
That means no taxes. I work every other night and, have no more than four
clients. This weekend Steph, me and three other girls are going to LA to
work a convention. I could make over $4000 for a weekend's work."
"Wow! Shit! That's amazing."
Anne smiled happily.
Billy studied her, trying to picture her having sex with all those men.
She was a pretty brunette hardly taller than 5' 2". Her slim, athletic
slim body was bursting with energy and life. Billy worried that working,
as an escort would dissipate that joie de vivre.
"Don't worry. Sex is good exercise for the body and the mind and I really
enjoy it. I have a group of regular clients who I really like and I still
feel excited about meeting someone new. I'm learning some amazing new
ways to do it. Anyway we have talked enough about me. What have you been
doing since school ended."
"Trying to find a job that will pay a huge wage for two months. There's
not many out there. I'm feeling a bit defeated."
"Good."
"Thanks."
"No, I'm glad you have reached this point because I have a proposition
which you would otherwise probably turn down without thinking about it."
"I'm not going to sell my body."
"That's not what I was going to suggest."
"Okay, what then?"
"In the agency I hear about all kinds of unusual things going on out
there in the big wide world that most people never hear about. Well next
week there is going to be a private fashion show at a very exclusive club
in Malibu. The models will be T-girls ..."
"What's a T-girl?"
"It's a transvestite or transsexual. Anyway, as I was saying, there is
this private show and the organizers are looking for three models. Each
model will be paid $3000 and get to spend a weekend at the club, which is
in a fabulous mansion on the beach. There will be a lot of people from
the T-girl magazine and video industry. All of the models will have all
kinds of opportunities to get some very lucrative contracts. It's a great
opportunity to get into the big time in this genre and make some serious
money without spending a lot of time away from your studies."
"And you think I should put on a dress and go spend a weekend with a
bunch of weirdoes? I don't think so."
"Wait. Just think about it. I am talking about making more money in one
weekend than you could make in two months at one of the jobs you have so
far failed to find."
"I am not going to wear a dress."
"For a good chance to make $3000, why not? It's just liked an acting
job."
"Because I'm not a fruitcake."
"Oh god! Here we go. Let's get all the male hang ups out into the open
right now and deal with them, then perhaps we can talk sensibly."
"That's not fair. I don't see why my not wanting to wear a dress should
be called a hang-up."
"Of course it is. When there are people ready and able to pay you a lot
of money to see you dress as a woman and you need the money and the best
you can do is say you don't want to be thought of as a fruitcake ... Well
I think that's just stupid."
Billy hated it when she got mad. He could not think fast enough to answer
her arguments, which meant that he usually lost. He also knew that he was
on shaky ground because she was giving him half the money she was making
from her escort work.
"I just don't want to become known as a sissy."
"No one will know. This is a very private club. They are all men who have
a thing about T-girls. They think they've died and gone to heaven when
they can watch a good-looking guy like you dress up as a woman. Believe
me they will never tell a soul about you."
"What kind of people are they?"
"Mostly businessmen. Many are gay. Others are bored with their wives or
women in general. The world is full of people with unconventional
interests. If I walked into their clubhouse wearing a sexy dress they
would not give me a second glance but if you do they'll give you three
grand. Amazing eh?... But its true."
That was a lot of money and Billy knew he had no right to turn it down
and take her money instead.
"Tell me what I would have to do."
"First you will have to be picked. They are looking for very attractive
males who can look convincingly female. And they have enough money to
cast a wide net for the best."
"What makes you think I would do?"
"You would look beautiful in a dress. You wouldn't even need make-up. I'm
pretty but you have a smoldering, sexy look that will knock people over.
You have classical feminine features ... No, I don't mean that in a
derogatory way ... In male clothes you're just good-looking but in a
dress you'd be gorgeous. You're one of these people that looks great as a
male or female."
She made him feel quite proud of himself. It was true that his nose was
straight and finely chiseled, his cheekbones were high, his eyes were
large, dark and deep, his chin was small and slightly pointed and he had
full red lips. When he smiled dimples formed in his cheeks, which his
mother had always loved.
"With a bit of make-up you would look fabulous."
Billy's defenses crumbled. He found her quick arguments and praise
irresistible.
"Okay, what do I have to do to get picked?"
"Take some lessons. There is a woman at the agency, who trains new girls
how to make themselves attractive to men. She's very good. She taught me
things about being a woman that I did not know about."
"Will I have to have sex?"
"No way. You don't have to do any thing you don't want to. Probably some
of the models will and there are T-girls who work at the club and do
that."
"What about clothes and jewelry?"
"I'll lend you some of mine and I can loan you some money to get some
things of your own. Once you have been picked the club will supply
everything."
"You seem very sure that I will be picked."
"I am. One of the organizers is a client and I showed him your photo. He
can't wait to see you in a bra." She giggled and putting her hand on his
said, "Just kidding. Don't look so serious. You might have fun. It's only
dressing up. Remember how we used to do it when we were kids? You really
liked wearing that satin bed jacket of mom's."
"He remembered. The satin had felt extraordinarily soft and sensuous. It
gave him his earliest hard-on."
"Alright, I'll do it."
"I knew you would come around. I'll call Jean tonight. Her name is Jean
Waters. She's strict but I guarantee you'll fall in love with her. You'll
have to stay at her apartment for a day or two. The auditions are on
Thursday and on Friday you fly to Malibu. That means you have three days
from tomorrow to get ready."
She phoned Miss Waters when they got back to the house and arranged for
Billy to go over there the next morning.
"She has enough clothes and I will give her some money that you can use.
You can pay me back after your weekend in Malibu."
2 - Miss Waters
Billy arrived punctually at 9 O'clock in the morning. He knocked on the
door of her apartment and it was opened by a tall, beautifully coifed and
dressed woman. She was wearing a sleek button front, navy dress in a soft
crepe. Her hose was nude colored with a silky sheen and on her feet she
wore dress pumps in navy suede. A gold, marine link chain draped around
her slender neck, gold hoops in her ears, a gold bangle on her right
wrist and a gold watch on her left set off the elegant dress. Her make-up
was the absolute minimum required to enhance her beautiful features
without taking away from her soft, luminous complexion. Her face was
framed in rich, shoulder length auburn curls. She was beautiful,
sophisticated, elegant and radiated self-confidence. Billy was
intimidated.
"Hi. I'm Billy Chambers."
She gave him a long, searching look.
"Come in Billy. Let me show you your room and then we can get down to
business. Anne tells me you have to be ready by Thursday. That's not a
lot of time. How do you feel about dressing as a woman?"
"Well I haven't got over the shock yet. I suppose I'll get used to it. I
just can't believe that I'll be very convincing."
"Don't worry. When I've finished with you your mother would be convinced
she must have borne a daughter all along."
"First thing we have to do is get you outfitted in something suitable so
that we can go shopping."
Her apartment was tastefully decorated and spacious with two bedrooms, a
large living room, dining room and kitchen, a large airy bathroom and a
solarium. It was decorated in an art deco style. The floors were highly
polished hardwood with an exquisite Persian rug in the center of the
living room. The two armchairs, a chaise and large sofa were upholstered
in a dark gray antique satin brocade. The dining room furniture was a
Scandinavian style polished teak.
"This is beautiful."
"Thank you. I like it too. Now, while I go and run a bath for you, I want
you to go into your bedroom and get undressed. I'll get you a housecoat
to put on."
She showed him into the spare bedroom which had a double bed covered in a
pink satin bedspread with a matching bed-skirt. There was a dresser and
chest of drawers. On the dresser was a selection of cosmetics, an earring
tree full of earrings and a jewelry box.
As he was removing his sweatshirt, shoes, socks and slacks she came in a
put a mid-thigh length wrap robe in white satin chemise. Billy put it on.
"Take off your briefs. You won't need them for a while. I'm going to put
your clothes in this drawer. From know on you will dress as a woman."
"All the time?"
"All the time, even in bed. Now are you going to take off your briefs?"
She spoke with authority and Billy took off his briefs, blushing as he
did so, because his pathetically small penis was exposed.
"This is going to be much easier than I expected."
"Why?"
"Well, the penis is always a bit of a problem to hide but yours is quite
small."
"I know. I've always hated it."
"Well, you can consider it an advantage for once. I want you to think and
feel like a woman and a big penis will not be help. Think of it as your
clitoris. Now get into the bath and I'll help you shave."
Billy slipped off the robe and stepped into the hot scented water. After
changing into a tracksuit she came into the bathroom and put a couple of
razors on the edge of the tub.
"I have made an appointment for you with a laser specialist to remove all
your body hair but the traditional method will have to do for now."
Most of his body hair was on his legs and there was not much of that.
When she got to his 'pubics' and put lather on he objected.
"Why is that necessary? No one is going to be looking there."
"You can't have unsightly hair showing outside your panty line. I told
you, I want you to act like a woman and feel like a woman. You must be
conscious of your appearance in lingerie as well as in your outer
clothes. Also, you will probably be wearing a swimsuit. Anne said you
were going to be a model at the Janus Club's fashion show."
"Yes, that's the plan."
"Well, you will be wearing some very skimpy lingerie. You definitely need
to shave your pubic hair."
She shaved and trimmed his pubic hair leaving a small, neat oval just
above his penis. He blushed as his penis stiffened when she held it to
shave around the shaft. As she worked she explained the regime she
intended to put him through. As soon as he was dressed she would take him
to a beauty salon to have his hair done and to have a manicure and
pedicure. He was also going to have a facial pack and his ears pierced.
After that she would take him shopping.
"Anne has provided the money. What's your shoe size by the way?"
"I take a seven."
"Oh, that's lucky. You may be able to fit into mine. Now here's a towel.
Let's go into the bedroom."
Billy dried himself and followed her into the bedroom. She had one of the
dresser drawers open and was picking out articles of underwear. On the
bed two breast-forms lay in specially molded containers on the bed. She
picked one up and placed an adhesive tape on the inside and then pressed
the prosthesis onto his chest.
"Hold it while I do the other," she pressed the other into place. "Now
slowly let go and see if it holds ... Good. Now put this on."
She handed him a white satin push-up, under-wired bra. Billy slipped his
arms through the straps and took hold of the two ends. Stretching them
behind his back he fumbled with the hooks and eyes. Eventually, after a
struggle he connected the two parts. She showed him how to adjust the bra
so that his bosom was correctly positioned.
"How does it feel?"
"Stupid."
So far he had accepted that he was to adopt a new role but he was not
reconciled yet. His maleness was not yet subsumed. Putting on the bra and
breast-forms brought out a small impulse to rebel.
"I hate it."
"That's not what I was asking you. I wanted to know if your bra felt
comfortable. I can't help it if you're embarrassed dressing as a woman. I
expect that as a male you will have all kinds of insecurities. But let me
make one thing clear. I don't care about that. I am proud to be a woman
and I have always thanked God that I am not a man. Whether you like it or
not, while you are in my charge you will disguise your feelings and wear
your bra with pride. Now put on these panties."
Her strong personality, which had initially intimidated him, combined
with her passion crushed his rebellion. He blushed and stammered an
apology.
"I'm sorry I did not mean to criticize you."
"You don't have to apologize to me but I don't want to have to deal with
any of your silly machismo. While you are with me I expect you to
constantly strive to be a beautiful, well turned out woman."
Billy stepped into the panties, which were made from a white stretch
satin. They were high cut briefs and it was immediately obvious that if
she had not shaved his pubic hair they would not have covered it.
In spite of his embarrassment he was beginning to find the experience
quite erotic. As he stood in front of her in his bra and panties he felt
a frisson of arousal. The bra and breasts felt so unusual and
unexpectedly appealing that his penis had stiffened and produced a very
unfeminine bulge in his panties. Worse, a small wet patch appeared in the
front of the panties as pre-cum began to ooze from the tip. Jean went
into the bathroom and brought back a box of panty-liners.
"Well, you obviously find the clothes a little bit interesting - No?
You're going to have to remember to put one of these inside your panties
or you will soil your clothes. Always keep a couple in your purse too."
"Its weird. I have never put on women's clothes in my life, nor had any
inclination to. But this is a real turn on."
"Possibly as many as one in ten males are secret or overt cross-dressers.
For some it's a fetish that may be confined to particular articles of
clothing like panties or high heels. I think it's partly the excitement
of exploring the unknown and the fact that cross-dressing is such a
taboo. In many cases lots of men have strong feminine characteristics,
which their stereotypical upbringings force them to repress. It's very
common so I shouldn't worry about it. Okay, put on this slip."
She was so sure of herself and took for granted that she would turn him
into a woman that he gradually ceased being embarrassed. She handed him a
white satin slip with lace appliqu? at the bust and hem. He slipped it
over his head and smoothed the shiny fabric over his body. He had never
worn anything satin before and this simply took his breath away. It was
soft and smooth. It caressed his skin. It felt delightfully sexy. His
penis was now throbbing stiff. He kept running his hands over the
delicious fabric especially over his bosom.
"Doesn't that feel nice?"
"I have never felt anything like it. It's wonderful!"
"Of course. See what you have been missing by being a male. All right,
now its time to put on your stockings. Most women today wear pantyhose
but I think stockings are much sexier and I think you will enjoy wearing
them."
She handed him a lace garter belt and helped put it on. Then she opened a
package of black nylons.
"You're going to wear a straight black, knee length skirt and a white
ruffle blouse. You could wear nude or some similar shade but black is
more assertive and much sexier."
He pulled on the stockings and fastened the tops to the garters carefully
straightening the ribbon on each clasp. She was right. Billy liked the
way the garters stretched over his buttocks and the gentle restraining
feel of the nylons sheathing his legs.. They were very sexy.
His mood had changed. Gone were his feelings of doubt and embarrassment.
When she handed him the white silk, ruffled blouse he put it on eagerly
and his fingers trembled slightly as he did up the buttons. It was a very
feminine piece of clothing. Again he noticed the soft tough of the
material on his skin.
He stepped into the skirt, which was lined and had a front pleated slit.
It made a nice rustling sound as he slid it up his legs. He reached
behind and drew up the back zip and closed the button fastener. Finally,
she gave him a three-inch wide elastic belt with a big gold buckle, which
drew in his waist and gave him and hourglass figure.
"There, how do the clothes feel?"
Billy paused and thought about it then said.
"Sexy, definitely sexy but comfortable too. I like the silky feel and the
way the skirt brushes my legs. The blouse feels wonderful."
"What about your bra. Is it comfortable?"
"Oh yes. I like it ... I like it a lot! It feels so neat and ... Er ...
liberating."
"Liberating? That's interesting. What do you mean?"
"It's difficult to describe. I feel like I don't have to put on an act
... The clothes somehow feel right ... I don't know ... It's hard to
explain."
"Umm! This is going to be easier than I had expected. I can see we're
going to have fun shopping. Now, we have to do you make-up."
Billy sat at the dresser while she put on a light skin cream and brushed
in some blue highlights on his eyelids. Carefully she applied a little
eyeliner, mascara and lipstick, her own lips very close to his. He could
feel the warm breeze of her breathe brush against his cheek. A surge of
desire swept over him. He raised his hand and stroked it across her
breast. She straightened up and quickly gave him a stinging blow across
his face with the palm of her hand. It was so fast that he heard the
crack before he felt the pain. He sat still in shock.
"You dammed sissy! Don't you dare come on to me! I told you to act and
feel like a woman. If there is any sex between us it will be you getting
fucked. Do you understand?"
Tears of humiliation and embarrassment welled up into his eyes as she
spoke.
"I'm s ...orry. Its just that you're ... so beautiful and ..."
"I know why you did it but you're supposed to think like a woman. It's
quite possible that a man will come onto you. It will be a giveaway if
you react like a man. You must try to think like a woman."
"Did you have to hit me?"
"Are you feeling hurt and humiliated?"
"Yes I am!" Tears still flowed.
"Good. Welcome to the woman's world. Get used to put downs, petty snubs,
and humiliations."
As she talked she repaired the damage done by his tears. She was right,
of course. He still burned with humiliation, which was compounded by the
fact of wearing a bra. At the same time he accepted without question her
dominance. As she removed the evidence of his tears with the make up
brush his humiliation was replaced by a renewed interest in the
transformation that he could see taking place in the dresser mirror. Jean
finished his make up and styled his hair in a more feminine way.
"I'll spend a lot of time with you showing you how to put on your make-up
and when I've finished you'll be better at it than most women. What do
you think?"
He looked in the mirror and a very attractive 'woman' looked back.
"Its very good. I look like a woman."
"No. You are beginning to look like a beautiful woman. There's much more
to do but it's a start. Try on these shoes."
She handed him a pair of black dress pumps with two-inch heels. They fit
comfortably.
"They fit perfectly." Billy walked around the room, wobbling at first but
after a couple of hints from Jean he soon walked steadily.
"How do you feel?"
"Feminine."
"Good, but you look like a man trying to walk in high heels. Short swings
when you move your arms ... hands spread out rather than clenched ...
that's it. Move your bottom as you walk ... good.
Billy spent an hour walking up and down until she was satisfied. We went
into the living room and he learned how to sit on a sofa, an armchair and
a dinning chair. He practiced feminine mannerisms like resting his hand
on his bosom, brushing his hair back with his fingers, and a hundred
others. When he made mistakes she snapped at him and when he slipped into
his male persona she slapped his face hard, making him cry. She was
merciless and he was constantly in tears. Each time he cried she would
send him into the bedroom to fix his make-up. After three hours the
lesson ended.
"Alright, its time to have some lunch and then go to your hair
appointment." She handed him a black leather shoulder bag. "Now what do
you need to put in your handbag?"
"Lipstick and gloss, mascara, eyeliner, eyebrow pencil, cream, and a
compact?"
"Very good. Go and get them." Billy sashayed into the bedroom and put the
cosmetics into the bag.
"What else will you need?"
"A purse for my ID, money and credit cards."
"Good. Use this one." She gave me a slim black leather purse.
"Anything else?"
"I don't think so."
"You need a small package of tissues, a couple of extra panty-liners, and
put a little bottle of scent in." When his handbag was complete she said.
"Now come and watch me get ready."
Billy followed her into her bedroom. This was a large airy room in a
granite pink and pale gray damask. The furniture was a spare modern style
in ivory. There were few feminine touches except for the cosmetics neatly
arranged on the dresser. Her large walk-in closet was full of expensive
suits, skirts and blouses but not many dresses.
She quickly took off her tracksuit and microfibre bra and thong. Billy
watched intently as she opened the dresser drawer and took out a black
satin and lace bra and matching brief. She quickly slipped her arms
through the straps and reached behind her back to fasten the garment. She
expertly arranged each of her firm breasts with large brown nipples into
the cups of her bra. Next she stepped into the silky briefs and pulled
them up her long slender legs and over her buttocks. Billy noticed that
her pubic her was completely removed leaving the lips of her vagina
visible. He covered up a surge of desire by concentrating on smoothing
his skirt.
She sat at the dresser in her bra and panties and pulled on charcoal gray
panty hose. She had the body of an athlete and radiated an absolute self-
assurance. Billy watched as she quickly applied just a hint of lipstick,
eye shadow and mascara. She went into the closet and selected a burgundy
silk striped blouse and immaculately tailored dark gray leather pants.
On her feet she wore gray suede pumps and, completed her look with gold
hoops in her ears and a thin gold chain necklace. She put on a black
leather thigh length coat and handed Billy a black silky, nylon jacket.
"Are you ready to face the world?"
"Yes, I think so."
As they walked to the car she said, "Men are going to come onto you in
droves. During the week I will teach you how to deal with that problem
but for today I want you to ignore any stares, whistles or any approach
of any kind. Act as though men don't even exist for you."
We drove into the shopping district and stopped at a restaurant. Billy
was utterly self-conscious as they entered and felt that everyone in the
room was staring at him. As the waitress took them to a table Jean
quietly told him to relax.
"You look every inch a woman. No one has a suspicion about the real you."
She insisted that he only eat a salad even though he was starving. "You
will have to get used to smaller portions. Being a beautiful woman means
always being hungry."
The novelty of being in public dressed as a woman made him uptight and
excited. "Relax. Try to look like you do this every day."
"It's the clothes. I don't wear a bra every day."
"How does it feel?"
"I like it. This whole thing is a blast. I think I could dress as a woman
all the time. Skirts are much more comfortable than pants and I really
like the silky feel of this blouse."
They chatted about feminine things and by the time they left the
restaurant he was much less self-conscious.
The beauty salon was across the street. Jean took him in and told
'Jerome' what he needed. Jean had told Jerome that Billy was a
transvestite, which horrified Billy and brought all his embarrassment
flooding back. But Jerome was familiar with the sensitivities of cross-
dressers just 'coming out' for the first time and quickly relaxed him.
Jean left him in his care and went off on some other business. Billy
spent the next two hours being pampered while Jerome he gave him lots of
advice about being TV. He explained that he too cross-dressed. He was
wearing a blue silk blouse and tailored slacks and Billy realized that
with a bosom he would look quite feminine.
"I've cross-dressed for years and I would be wearing a dress right now
except that most of our clients wouldn't like that."
3 - The backdoor
Jean returned after three hours and chatted with Jerome about Billy's
hair and nails. Billy's hair was relatively long for a male but not for a
woman. He had shaped it into a cute 'bob' that had a nice 'bounce' as he
turned his head. His ears were now pierced and sported two diamond studs
in each lobe. His nails on his toes and fingers had been shaped, painted
hot pink, and polished. Jerome had re-done Billy's make-up and was
putting the finishing touches to the lip-gloss as Jean had returned to
the beauty parlor.
"You will need a more feminine name. What would you like to call
yourself?"
"Umm. I don't know. I like 'Claire' or 'Cynthia' or ..."
"Why not Billie ... with an 'i.e.'? Then you won't have to remember
anything."
"That's very clever of you, Jerome. What do you think, Billie?"
"I like it."
Jerome took the cape off Billie's shoulders and said.
"What do you think?"
"Amazing! I look completely female."
"Do you like yourself?"
"Oh yes. This is neat. What do you think Jean?"
"You've done an excellent job, Jerome. You look very pretty Billie."
"Beware of men, Billie!" said Jerome as he patted Billie's bottom.
Billie giggled and thought Jerome was joking but as he and Jean headed
for the mall he was aware of many appreciative stares from men as they
passed by. Billie found it intriguing and not unpleasant. He walked
confidently and pushed his bosom forward.
They looked for dresses first and Billie enjoyed trying on various
styles. He was the center of attention and, unlike when he used to buy
his male clothes, style and look were now very important. He even tried
on a satin ball gown, which took his breath away. He knew that he looked
stunning.
After two hours they settled on a navy Jacquard dress with a mid-calf
length flared skirt and long sleeves, a short-sleeved crepe dress with
satin scalloped detail, and a sleeveless red georgette dress, which fell
to just above his knees.
"You'll need something for evenings," Jean said after they had purchased
all the necessary accessories for the three dresses, which included a
pair of black patent dress pumps with 3-1/2 inch heels and a pair of
silver, 'strappy' sandals with 4 inch heels accented with rhinestones and
some pieces of costume jewelry.
They went to Jean's favorite formal wear boutique and after trying on
three gowns they settled on a burgundy taffeta skirt with a strapless,
taffeta corset top and a taffeta shawl. This dress was the beginning of
his love affair with taffeta. He adored the stiff silky feel and the
sensuous rustling sound of the fabric as he moved. They bought a pair of
black ankle strap sandals with a velvet finish and a black satin evening
bag.
After a break for supper they finished off the shopping trip with a quick
breeze through a department store beginning in the lingerie department to
buy two bras, six pair of panties, an ivory satin slip, six pair of panty
hose, two pair of stockings and a garter belt. Finally, on their way out
they passed through the cosmetics department and bought lipstick,
mascara, eye shadow, eyebrow pencil, nail polish and facial cream.
Billie was exhausted when they got back to Jean's apartment.
"God, we've spent a fortune. How much did Anne give you?"
"Enough, but it will take you a while to pay her back. Tomorrow, we'll
get you some skirts and blouses and you'll need some special underwear
for the gown and your georgette dress."
Jean lent Billie a satin nightgown and after a relaxing cup of tea he
went to bed and snuggled between the satin sheets and folding his arms
protectively over his bosom.
As he drifted into sleep he reflected on how much he had enjoyed the day.
It wasn't bad being a woman. He liked the feel of the clothes, the
concern with his 'look' and the pleasant 'restrictions' placed on his
body by his bra and the high heels of his shoes. He loved the clingy feel
of his stockings and the way his skirt brushed against his legs. He had
discovered a real interest in experimenting with make-up and liked the
feel of lipstick on his lips. But most of all he has found the way men
looked at him very stimulating.
He spent the next morning learning more about make-up and trying
different looks with some of Jean's skirts and tops. The time flew by as
he became completely absorbed in how he could so drastically change his
appearance. Jean found him a very quick study and gave him 'his head' to
experiment. She had a selection of wigs and he had fun teasing the long
hair into various styles with ribbons and clasps.
That afternoon they shopped again and when they stopped into a cocktail
lounge for a drink, he was thrilled when Jean went to the ladies and a
man tried to 'pick him up'. It started him thinking about what it might
be like to be kissed by a man. He told Jean what had happened.
"What did you say?"
"I just shook my head and he left but it set me wondering what it might
be like to be kissed by a man," he giggled self-consciously.
"Umm! I find it hard to believe that you haven't experimented with
women's clothes before."
"Why?"
"Because you've taken to it so easily. You seem to have an almost
permanent erection ..."
"Oh God! Is it that noticeable?"
"Only when you're undressed but I'm making an assumption."
"Well, you're right. I can't help it. The clothes feel so sexy. For the
first time in my life I'm glad I have a small penis."
Jean laughed.
"Have you ever had sex with a man?"
"No. I haven't even done it with a woman."
"Have you ever fantasized about doing it with a man?"
"A few times ... Yes, actually, a lot. It has always bothered me. I never
did until one time I saw Anne doing it."
"Oh. Tell me about it."
"Well, it was a couple of years ago. She was home for the weekend and had
bought her latest boyfriend, a big black guy called Jess. He was on the
football team. He just towered over her. Any way, I was out in the garden
helping mother and went inside to get something. I heard Anne crying so I
ran up the stairs and to her bedroom. The door was open and I could see
her on her knees on the bed with Jess behind her. I was appalled at
first. I could see his huge cock thrusting into her vagina. As his cock
moved inside her I could hear a squishy sound as though she was wet
inside.
He was thrusting so fast and hard that his body made a slapping noise as
his pelvis hit her bottom. I was fascinated by the way her buttocks
bounced and her breasts swayed. And I noticed that she had big nipples. I
quickly realized that her cries were not from pain. In fact, as I watched
he pulled out of her and she moaned with disappointment but as he pushed
his cock into her anus she gasped with a big smile on her face. The size
of his penis just floored me. After my own, this was the first penis I
had seen and it was three times as big as mine. For the first time, I
felt inadequate as a male."
"Umm, that's interesting ... Go on."
"He fucked her anally for about five minutes then quickly pulled out of
her. He flipped her on her back and put his penis into her mouth and
came. I didn't see his cum but it was obvious she was swallowing it. I
could not think of anything else all weekend. I never saw them do it
again but I noticed the way she touched him and I heard them at night."
"Did you imagine yourself doing to a girl?"
"No. I just thought about what it would be like to be Anne."
"That's interesting. Well, I think you will find out soon enough."
"What do you mean?"
"Well, you're going to Malibu, aren't you?"
"If I'm selected but ...?"
"You'll be selected and you'll be one of three beautiful young males
wearing provocative lingerie and flaunting yourselves in front of twelve
men who find women either unattractive or dull. And you'll be alone with
them for a weekend. You're not being paid $3000 just for wearing a bra."
Billie stared at her open-mouthed.
"Don't tell me you didn't think of that?" she laughed helplessly. "Oh
dear, oh my ... that sister of yours is quite the little minx."
"She said that I would go for the afternoon and when the show was over I
could leave. She said that I would not have to do anything I did not want
to do."
"Well ... I guess that's true. It's just that I can't imagine you not
wanting to. You're such a sexy thing. Oh well, we'll see." She shrugged
her shoulders.
When they got back to the apartment, Jean decided he was ready for some
more intimate feminization. She told him to put away the new purchases
and then to come into her bedroom. When he had done as he was told he
went into her bedroom. Jean unbuttoned Billie's blouse and slipped it off
his shoulders bringing her lips close to his as the silky fabric slid
down his arms.
"You're trembling. That's good. I don't want you to let your male
instincts get in the way. Be submissive and accepting."
There was no fear of his male instincts taking over. He was completely
intimidated by her. The bra, garter-belt and stockings he was wearing
effectively kept his maleness thoroughly subdued.
Her lips pressed onto his as she unfastened his belt and unzipped his
skirt letting if fall around his ankles. She raised the lace hem of his
chemise and cupped his genitals in her hand. His achingly erect penis
strained against the restraining nylon spandex of his thong as she
squeezed and stroked the bulge gently. Her lips moved to his neck and
shoulders while her other hand cupped his buttock and squeezed it firmly.
Billie moaned and sighed and placed his hands on her back stroking the
soft satin of her blouse and tracing the outline of the back of her bra.
"That's very good. You sigh like a girl being kissed. Now take off my
blouse and slacks."
Jean enjoyed the sensation of holding his slender, effeminate body, which
trembled as his desire soared. Billie was only the second lady-boy she
had worked. They were both so horny. She suspected that Billie would have
a voracious appetite for sex once it was released. Certainly, his sister
did. She was the agency's leading escort. Jean had done a few conventions
with Anne and found her eager to try anything. Jean was hoping that the
weekend in Malibu would show Billie to be like his sister. The agency
desperately needed another lady-boy. The demand for them was huge. Billie
was very beautiful and emanated a torrid sexuality that would drive the
clients wild.
With shaking hands Billie unfastened the buttons of her blouse as she
kissed his lips and flicked her tongue into his mouth. With mounting
excitement he felt the smooth, warmth of her breasts inside the white
cups of her bra. His breathing was heavy and coming in uneven gasps. He
fumbled with the button and zip of her slacks and eventually loosened it
and guided the garment down her thighs.
"Now take off my panties, Billie," she said between wet open-mouth
kisses. He slipped them over her bottom but something was preventing them
coming down. He moved his hands to her front and found to his shock that
she had a strapped on dildo. He paused and she took over pulling her
panties down and at the same time pushing him back on to the bed. He lay
back passively as she spread his nylon sheathed legs and stood between
them. She looked feminine but also masterful with the black rubber dildo
jutting aggressively from her groin. It was about eight inches long and a
perfect replica of a penis and testicles. There was an open pot of cream
on the night table and she spread this on the dildo.
"Now you're going to have an important feminine experience. She pulled
aside the crotch of his panties and pushed the tip of the dildo against
his anus. He felt it spread his opening wide and he gasped, scared that
it was going to hurt. He gripped her arms as his anus stretched and cried
out as the tip suddenly overcame the resistance of his tight entrance and
thrust into him. Impaled on the dildo he had a feeling of utter helpless.
The sensation increased as she began thrusting the stiff phallus deeper
into him. He closed his eyes and relaxed his legs. She hooked one arm
under his right leg and bent it back against his abdomen. When she had
fully penetrated him, he felt her abdomen slap against his buttocks with
each thrust.
"Uugghh! ... Mmm ... Oh God!" he moaned and cried out. His own penis was
stiff and rubbed against the fabric of his panties. He was quickly coming
to a climax. Three more deep thrusts and two days of incredibly arousing
cross-dressing and his penis exploded.
"Oh! I'm coming ... Oh ... Oooh!!" Semen gushed into his panties. As he
came she thrust hard driving the dildo deep into him. The pressure of
their bodies squeezed the "testicles" attached to the dildo and squirted
fluid into his rectum. She grunted like a man having an orgasm and
collapsed on top of him jerking and thrusting. It was a very credible
performance and as sticky fluid oozed from his stretched anus onto the
inside of his thigh he felt he had been fucked.
"That was great ... Ummm. Do it again!"
"Go and clean up and change into something sexy then you can try to get
me aroused again."
He went into the bathroom and sat on the toilet releasing the fluid from
his rectum and cleaned himself. He took off his bra, garter belt and
stockings, and panties and went into his bedroom. He slipped into a pink
baby doll in a thin satin and trimmed with a marabou fur at the hem. He
pulled on a matching thong and slipped on a pair of pink satin mules with
four-inch heels. After putting on fresh mascara and a bright red lipstick
dabbing perfume onto various erogenous zones of his body he returned to
Jean's bedroom. She was in the bed in men's satin pajamas. The dildo was
still strapped on her crotch.
Billie slipped into bed bedside her and just as he had seen the woman in
porn videos he began stroking her and kissing her lightly. Slowly he
worked his way down her abdomen and proceeded to suck the dildo, moaning
and sighing. After a few minutes of this, while she stroked his hair, she
pushed him back on the bed and went down on his anus probing with her
tongue. She avoided touched his very stiff penis which was safely tucked
inside his thong.
He desperately wanted her to fuck him again and found himself encouraging
her to use his body. Her tongue felt wonderful and he wiggled and
squealed happily as her mouth sucked on his anus and her tongue moved
inside him. Things felt deliciously warm and wet down there.
"Ooh that feels lovely ... Uuumph! ... Mmmm ... Oh ye ...es! Oh fuck me
... Unnnn I want you!" Two days of intensive feminization had done its
work. He wanted to be penetrated.
As she entered him he clasped his legs around her waist and pushed up
against her thrusting pelvis, moaning and begging her to fuck him harder.
She roughly swung him over onto his knees and drove the dildo into him
from behind. She fucked him hard for 15 minutes and then unleashed the
fluid spurting it into his expectant rectum. He screamed as she spurted.
"You are a hot little thing, just like your sister," she said this as she
slowly moved the dildo in his flooded rectum keeping him in an inflamed
state.
4 - Work
After one more day of Jean's tuition Billie was ready to audition for the
fashion show. So absorbed had he become in developing his feminine side
and transforming himself into as feminine a person as was possible that
he had not given any more thought to the implications of going out to a
private club to exhibit his feminine charms to twelve men who took a
sexual interest in males with such charms. His natural competitiveness
had risen to the surface and he simply wanted to be selected to prove he
could do it.
Jean's 'sexual' instruction had also had an effect. He had never had sex
or any intimate relation with a female before Jean. She was the first and
he was infatuated with her. He had slept with her for the last two nights
and she had fucked him several times during the previous day. He was
completely in her power - her sex slave.
All the previous day she had worn the dildo under her slacks. On more
than eleven different occasions, whatever he happened to be doing, she
would seize him, fondle and kiss his body roughly, pull up his skirt and
pull down (and three times tear off) his panties and fuck him usually
from behind. Twice while they were out shopping she took him into a
cubicle in a ladies toilet and fucked him. He loved it. He loved the way
she handled him roughly, just taking him when and where she wanted. Each
time she approached him his anus dilated expectantly.
The result of all this was that he became conscious not just of his
feminine bent for pretty things and a desire to look pretty but also of a
certain female sexuality. Significantly, these initial sexual experiences
caused him always to associate penetration with sexual fulfillment.
Jean took him to the offices of a T-girl magazine and he was conducted
into a photographic studio. Billie had dressed for the occasion in a gold
satin sleeveless dress with a fringe hemline, gold sandals and his
sexiest underwear, a flesh colored satin bra, matching panties and nude
stay up stockings.
The photographer introduced himself.
"Hi. I'm Dan."
"Hi Dan, I'm Billie."
"That's a stunning dress - or maybe it's the body inside it?"
"Thank you."
The studio was dominated by a king size bed covered in black satin
bedding. Two klieg lights stood at the foot and to one side. Video and
still cameras on stands were directed at the bed. Dan picked up a third
camera and began photographing Billie giving him rapid fire instructions
to walk, turn, bend, swing, pout and so on. After 20 minutes he told him
to remove his dress and get onto the bed. Billie had a glorious time
rolling and vamping on the satin sheets.
A hitherto unsuspected exhibitionist streak kicked in. He found it erotic
to recline on the bed in a bra and panties, spread his legs and display
his buttocks lewdly in front of a stranger. When he was told to take off
his panties his penis stood out stiffly. He took off his bra and false
breasts and pinched his nipples as he knelt on the bed wearing only
garter belt, nylons and shoes. Later when Billie saw the prints he was
pleased at how feminine he still looked despite the absence of a bosom
and a cock standing up like a flagpole.
Of course, he was chosen to be one of the models and on Friday afternoon
he boarded the flight for Malibu. His ticket showed him returning late in
the evening. Whatever Jean thought, he was taking Anne at her word and
assuming that he was not expected to stay for the weekend. But once he
was on the plane he began to wonder whether he would stay. His mind
flipped back to Jean's dildo. He already missed it. What would the real
thing be like?
He had dressed in a white silk, long sleeved blouse with ruffles, a
short, above the knee kilt in the Stewart tartan, a black velvet vest,
black stockings and black pumps. Jean had picked out the outfit and
thought he looked cute. He felt cute and sexy. He looked down at his
legs. They were crossed at the ankles and bent sideways in the elegant
pose, which Jean had taught him. He recognized that they were beautiful.
He stretched out his hands and admired the manicurist's work. He had long
false nails painted bright red and shining with polish. He was now used
to the 'clinging' of the false nail glued to his real nails. Jean had
assured him that he was very desirable and that pleased him. If he stayed
he would find out how desirable he was.
He did not meet the other two models until he found the chauffeur holding
up the Club's sign in the arrivals lounge. They were standing beside the
man looking nervous but very pretty. They were the same build as Billie
but one was Asian with long shiny black hair and the other was Afro-
American with ebony skin and a shaved head. They introduced themselves.
"Hi, I'm Billie."
"Hi, Billie. I'm Frances."
Billie shook the hand of the black model.
"And I'm Suzie."
The three lady-boys followed the chauffeur to the limousine pulling their
wheeled overnight cases, their stiletto heels clicking on the pavement.
They had been instructed to bring one change of clothing, their make-up
and some toiletries. All the clothes would be supplied.
Shyness and tension ensured that the 40-minute drive was silent.
Eventually, the limousine pulled into a long driveway, which took them to
a huge mansion on the waterfront. Inside a T-girl in a black taffeta
maid's dress, high heels and fishnet stockings met them.
They were each shown to a bedroom. The pink and slate blue d?cor of
Billie's room was bright and cheerful. The huge bed was upholstered in a
matching pink satin. The drapes were made from the same material. Billie
unpacked his overnight bag arranging his make-up on the dresser, hanging
the blouse and skirt that he intended to wear on the way back in the
closet and putting his lingerie into one of the dresser draws. In doing
so he discovered a closet full of gorgeous clothes and drawers brimming
with heavenly lingerie. It was a cross-dressers dream. When he checked he
found that the clothes were all his size. He forgot that he was leaving
that evening and wondered if there was enough time in the weekend to try
everything on.
A new T-girl maid in a yellow satin maid's dress interrupted his reverie.
"Hi, Billie. I'm Nancy. Is the room suitable?"
"Oh yes. It's gorgeous."
"Good. Well the guests will be here in an hour. Could you come with me
and we'll have a meeting about the show."
Billie followed Nancy down the stairs into a large room dominated by
three racks on which hung some dresses, gowns and lingerie. Beside each
rack was a large table with open boxes filled with jewelry, bras,
panties, nylons, and a wide range of accessories.
Frances and Suzie joined Billie. They looked at Nancy.
"Welcome to the Janus Club girls. The fashion show will start in 90
minutes. This is the changing area and you will each be assigned a
dresser. They will be along in a moment. Now through here is the lounge
area where the guests will be sitting.
They followed Nancy through some heavy drapes into a comfortable lounge
with several circular mahogany coffee tables with armchairs and couches
around them. One wall was made up of large French windows, which looked
out onto the ocean.
"Oh! This is beautiful!" said Suzie. There was a boyish quality about the
pretty Asian, which came through despite his white satin blouse, black
dirndl skirt, and patent high-heeled pumps.
"Yes, isn't it. Now see the different colored arrows on the carpet?"
"Oh yes." We chorused.
"Well, you follow the pink arrows Billie, You're blue Suzie and you're
yellow Frances. You will all go out together and if you stick to your
colors you will pass by the largest number of guests at the same time
without bumping into each other."
Nancy made them do a practice walk. Frances bumped into Billie and they
giggled. Frances was wearing a long, navy skirt and a white mohair
sweater with a silk scarf. He was almost indistinguishable from a girl.
They did the walk three times.
"Good. Now girls, this is a relaxed social event so I would like you to
take your time at each table, introduce yourself to the guests and talk
to them. Be friendly and get to know them. Any questions so far?"
"What if they want to do more than talk?" asked Frances with a smirk on
his pretty face.
"I don't think I need to tell you what to do, sweetie. Follow your
instincts. Yes, Suzie?"
"How many changes of clothes do we do?"
"First you will all wear a gown in the color of your floor arrow. After
that you will wear two lingerie outfits."
"Then what happens?"
"All the members have paid to have private showings. They will chose
which of you they would like to be their model and you will go with them
to a private room for the sessions."
"Do we have to do that?" Billie was getting worried.
"No. After the session in the lounge you can let me know that you don't
want to do a private show. Of course, you will not get paid the full
$3000 and you will have to return tonight. But I noticed that you were
booked on a flight."
"Yes. I'm not really sure what I want to do. I've never done this
before."
"Jean told me you were new. Don't worry. You don't have to decide now."
"Now follow me and I'll give you a tour of the house." They sashayed
after Nancy on their stiletto heels vying with each other in trying to
look excessively feminine. There was a lot of 'Ooos' and 'Aaahs' as they
went from one splendid room to another. Each guest had a large bedroom
and en suite bathroom. The beds all had satin sheets.
"This is what we call the 'playroom'"
This was a large comfortable but dimly lit room with a fireplace. Heavy
drapes were pulled across the windows. There were a couple of armchairs
and a sofa but mostly just large satin upholstered cushions scattered
around. Billie did not see any games. There was however a TV projector
and a large screen in one corner.
"Well, its time to get dressed. I'd like you all to go back to your
rooms, shower and shave, if necessary, and put on your favorite perfume.
You'll find a housecoat in your closets. Put that on then come down to
the changing area. You won't need your breast forms. You're just wearing
padded bras. Off you go."
Full of excitement they hurried to their rooms. On the way Frances and
Suzie said they hoped he would stay.
"It will be fun. I was here six months ago and it was wonderful."
"But did you have to have sex?"
"Of course! I didn't have to its just they could not have stopped me.
With your looks these guys will go crazy about you, won't they Frances?"
"Definitely!"
"I wouldn't know what to do."
"You don't have to know. Just relax and let them do the work. You just
enjoy yourself."
Billie was the first into the changing area. There he found his dresser,
Sherri, an attractive but quite obviously male T-girl. He was wearing
maid's dress in a pink taffeta. It had a multi-layered, white ruffled
petticoat and a fitted bodice with puffy sleeves. He was very effeminate.
"I'm Billie."
"Hi Billie, I'm Sherri. Ooh! You are a pretty sissy."
He slipped Billie's black satin housecoat off his shoulders and hung it
on the clothes rack. Standing in front of him he clasped Billie's
buttocks gently.
"Ummm! What a lovely tush you have, sweetheart."
Billie did not move away from the touch. He liked the soft silkiness of
Sherri's dress against his abdomen and crotch. His small penis stiffened
and rose up into the organza folds of Sherri's petticoats. Sherri kept
his hand on Billie's soft ivory globes causing our hero to blush.
"Oh, I just adore working on pretty boys and you are very sensual ... Umm
... and your skin is so soft."
Billie shivered, less from being naked than in response to the blatantly
sexual fondling of his bottom. Instinctively he moved closer to Sherri
crushing the stiff folds of Sherri's dress. His penis touched Sherri's
ruffled knickers. As Sherri's lips touched his Billie closed his eyes.
They kissed lightly and slowly with open mouths. Although, clearly not a
woman, Sherri's lips, scarlet with lipstick felt like a woman's. Billie
felt the telltale dilation of his anus and a familiar weakness in his
legs. He embraced Sherri enjoying the feel of Sherri's satin dress.
As they broke their kiss Billie heard whistling and clapping. He turned
to see Frances and Suzie, already in their bras smiling at him. Sherri
whispered.
"You are a hot little number."
"I couldn't help myself."
"I could tell, Sweetheart."
He handed Billie a white satin, under-wired bra and a thong.
"Put these on. Now you are all going to wear the same style of dress for
the first go round."
He held up a pink satin dress with a long straight skirt, an empire
waist, a square neck and short sleeves. A satin bow accented the center
of the bodice from which hung two long satin ribbons.
"What do you think?"
"It's lovely. I can't wait to put it on," Billie smiled.
"Stockings first and make-up."
Billie pulled on nude stay-up stockings with lace tops and slipped on his
housecoat and sat at the dresser. Sherri handed him a pair of silver,
ankle strap sandals with four-inch stiletto heels. After helping him
fasten the straps Sherri did his make-up and kept Billie feeling very
aroused by stoking his neck and ears.
"You're lucky to have short a small penis. Is it always erect?"
They both laughed.
"It usually has been since I started cross-dressing and right now I think
it likes what you are doing to my neck and ears."
"Umm! Well see how it likes this."
Sherri kissed Billie's ear and nibbled at his ear lobe. It touched a
funny nerve and Billie squealed helplessly causing the others in the room
to look at them.
"Oh God ... That was too much."
Sherri kissed Billie's lips with some intensity.
"You and I are going to need some private time together, sweetheart. Give
me your hand."
He took Billie's hand and brought it under his petticoats and, pulling
down his knickers, he guided Billie's hand onto his rigid cock. It was
far bigger than his own penis and Sherri's testicles felt huge. Billie
grasped the shaft. It was the first cock he had ever held other than his
own poor excuse. He felt the sexual potential as the blood pumped causing
it to throb slightly in his hand.
"Oh! Its big."
"Wouldn't you like to sit on that? Ummh! ... Feel it thrusting inside
you? How about that?"
Sherri raised his skirts so that Billie could see the very big phallus in
his hand. Billie was speechless and transfixed by the size of Sherri's
member, the intimacy of holding another man's penis, and the enormity
Sherri's suggestion.
"Put it in your mouth."
Sherri pushed Billie's head down to his cock. Billie was drawn towards it
and afraid. He was saved by Felicity, a T-girl maid in a red satin
uniform.
"Hey guys, let's go. We have five minutes."
Sherri kissed Billie's lips and said, "later honey."
Billie breathed a sigh of relief as Sherri helped him on with his dress,
zipped up the back, gave some last minute flicks to his hair and handed
Billie a posy of pink carnations tied with a satin ribbon.
Billie forgot about the dangerous moment with Sherri as he became fully
absorbed in the feel of his dress. He adored the way the satin flowed
around his body as he moved. Felicity gathered all three sissies together
for a little pep talk before they sashayed out into the guest room.
Frances and Suzie looked cute in the same style of dress that Billie had
on except they were respectively in blue and yellow satin with a posy of
flowers to match.
"Off you go girls. Remember to be friendly."
Billie walked into the guest room and saw two men in tuxedos sitting in
armchairs at each of the six coffee tables. Following the pink arrows he
walked to the first at which sat two good-looking middle-aged men, one of
whom was black. Billie said his rehearsed introductory speech.
"Hi, my name is Billie. I'm 19 years old and a college student. I've been
cross-dressing for two weeks."
"Hi Billie," said the black man, "that's a very pretty dress. Come and
sit on my knee."
Billie had been told this might happen and so very demurely he sat
carefully on the man's knees. Immediately he felt the man's hands roam
over his body feeling his curves under the satin dress. The man's fingers
touched a sensitive point in the small of Billie's back making him jump
nervously.
"Umm! You're a frisky little filly. His hands explored Billie's buttocks
and thighs. Billie squirmed. Being felt like this was very erotic and
Billie felt surges of desire pulse through his body but he was also
unsure what to do.
"Check this babe, Jerry."
The man lifted Billie off his knees and set him on Jerry's knees. Jerry's
hands felt Billie's body and he kissed and nuzzled Billie's neck. Billie
felt Jerry's handclasp his genitals making him gasp. Billie squirmed as
his body responded to the squeezing and stroking and his dress rustled
and swished as he moved. He was becoming very horny and reckless.
As he got up off Jerry's knees to go to the next table he saw Suzie and
Frances being felt and kissed. Frances was laid back across one man's
knees while the other man was kissing him full on the lips. Suzie's guest
had his hand up under Suzie's dress. Both sissies seem to be enjoying the
attention so Billie decided to relax and enjoy it too. It was at this
moment that, barring something unpleasant happening, he decided to stay
At the next table he sat on one of the men's knees without being asked .
Before he could finish his introductory speech he was pulled backwards
and kissed on his lips. Four hands explored his body, this time under his
dress. His sex was squeezed and stroked and his anus probed with fingers.
As each man in the room felt, probed and kissed him he became more and
more horny.
It took 30 minutes to complete the circuit before he returned to the
changing area with Frances and Suzie.
"Oh! God! I'm so ready to be fucked," sighed Suzie.
"There's some gorgeous meat out there. I don't think the weekend is long
enough," said Frances.
"I saw you really getting into it with that Hispanic stud, Billie. You
were really squealing."
Billie remembere . The man had managed to insert two fingers into
Billie's anus and Billie had wiggled on the intrusion gasping and crying.
"Yes, I know. I was shocked at what he was doing."
"You sounded as though you had gone to heaven."
"Have you decided whether to stay?"
"Yes, I think I will"
"Oh good!" said Frances, "I can guarantee you will have fun."
They went to their separate dressers and changed. Sherri helped Billie
out of his dress and into a blue satin corset, black fishnet stockings
and black patent pumps with four-inch brass spiked heels. He did not wear
any panties so his small penis stuck out stiffly from beneath the frilly
lace hem of his corset. Sherri fondled and kissed Billie as he helped him
repair his make-up. Sherri was extremely aroused and Billie sensed that
he could easily unleash a storm of passion if he gave Sherri half an
excuse.
He looked at himself in the mirror. The corset looked and felt incredibly
sexy. He ran his hands over the satin panels.
"What do you think?"
"Sexy!"
"You look very fuckable. Are you going to stay?"
"Yes."
5 - Pleasure
As the three sissies went around the room a second time Billie was
acutely conscious of his role as sex object. The twelve men wanted his
body. This knowledge gave him a strange feeling of power. He felt the
sexual need in their bodies as they kissed him. He kissed them back more
actively, opening his mouth and letting them explore with their tongues.
Billie fondled their ears and necked as they kissed encouraging them.
With his penis exposed each man fondled and stroked the hard spear of
desire. Several men kissed and sucked it causing Billie to moan with
pleasure.
Billie held and stroked all of their cocks. Most were between six and
seven inches long but two where very long, at least nine inches. The
black man had the longest. It was straight and hard. Some were curved up
and three were too thick to get his fingers arou