Detective Story
By Jennifer Stewart
New Assignment
I sat in Geoff's office mulling over the assignment he had
given me. He was not in the room having gone up to finance
to cut me a check for my expenses. He wanted me to go
undercover to investigate a transgender sex slave ring,
which was funneling a lot of young men to India and the
Middle East where they became sex slaves to the degenerate
wealthy. Parents of the disappeared had filed 'missing
persons' information. They were males between 19 and 25,
and all had belonged to three TG clubs in the city.
Obviously, they were cross dressers. Geoff wanted me to
join these clubs and see if I could come up with some
leads.
"Why do I have to do this? I've been making real progress
on those break-ins. Putting on dresses is not my thing."
"I know that. None of the guys likes it. But it's not a
matter of what you like. You have the right size and looks
that make you a cinch to go under cover on something like
this."
I was 5' 4" and very slim. My looks tended to the "cute"
and my hair was shoulder length. I had twice dressed as a
woman in the course of duty to entrap 'Johns'. Everybody
had to take a turn but I had been the most convincing.
"Why don't you use one of the women?"
"Aw, c'mon. These are all guys - trannies. A dame would be
spotted too easily. You're the best we have for this sort
of job. I thought you didn't mind. You always looked at
ease in drag."
Actually, I had found it a bore walking up a down the
streets in the 'entertainment district' in very
uncomfortable clothes and shoes. The police had very bad
taste in women's clothing and there was not a lot of sizes
to chose from. Only a gaudy pair of red high heels fit me
and I hated wearing underwear that other people had worn.
After the first assignment in drag I had bought black
pumps, a bra, panties, hose and a chemise of my own and
hidden them in my locker.
After some complaining and because the assignment would
involve wearing drag for weeks at a time Geoff had agreed
to issue me an expenses check so I could get my own
clothes.
"Don't go over $200."
"Geoff, I need a week's worth of clothes. Two hundred will
get me one cheap outfit! I know for a fact that cross-
dressers like wearing evening gowns. They're expensive."
"I'll get the girls to help out."
"Oh great. That's all I need. The whole precinct to know
that I'm wearing drag."
"Don't worry. I won't say whom the clothes are for. Just
give me your sizes."
I was not worried about finding the clothes I just wanted
to make it difficult for him. My girlfriend, Ginny, would
lend me hers. She found it kinky when I had to go out in
drag. She was a very sexy chick with a fondness for erotic
lingerie. I liked running my hands over the satin slips and
bras she liked to wear. Once, when we were fooling around
in bed she made me wear one of her satin bras while we
fucked. Secretly, I had liked the feel.
"Here's a check. This should be enough. Don't go native on
me."
"Thanks, and very funny. I'll check in tomorrow morning."
"Okay, take care. Put this in your purse."
He gave me a woman's Beretta pistol that fired two shots. I
doubted that I would need it but thanked him anyway.
The station had a small store of clothes and make-up so I
helped myself to a few items of make-up until I had
accumulated my own. The store also had breast forms and I
chose a B cup size with big nipples. My expenses would
cover the cost of some lingerie, nylons and a couple of
outfits. Several female colleagues donated some sweaters,
blouses and skirts. Ginny spent some time giving me tips on
applying make-up. She thought it a riot that I had to go
under cover for a week or more.
"What are you going to do if some handsome hunk comes on to
you?" She giggled.
"Say I have a headache, isn't that what do you do?"
"Oh that never works. You'll just have to lie back and
enjoy it!" She was laughing helplessly.
While I was shopping I saw a pink taffeta evening gown with
a bolero jacket and decided to buy it. The clubs all had
dancing and I suspected that long gowns would be mandatory.
I picked out three bras, one strapless and all in pastel
shades of satin. I chose matching panties and thongs, a
garter belt, two satin slips in black and white, a camisole
and a half-slip. I went back to my flat to change.
I quite liked the feel of the pale blue satin bra. The bra
I had stored in my locker was cotton. This was different,
under-wired, and stiff with newness and with a lustrous
sheen. I couldn't resist running my fingers over the satin
cups after I had popped the breast-forms in and adjusted
the straps. As I looked in the mirror my penis stood out
stiffly signaling my body's appreciation of this
interesting garment. It remained achingly erect as I pulled
up matching pale blue satin panties and slipped the white
satin slip over my head. I felt and saw my pre-cum ooze
into my panties and spread a wet patch over the fabric. Two
folded Kleenex stuffed in the panties took care of that and
I made a mental note to buy some panty-liners.
The lingerie felt absolutely dreamy and exquisitely sexy.
This was unexpected and I put it down to the fact that on
the other two occasions I had worn drag I had dressed
hurriedly in the police locker room and quickly headed out
with my partner. Now I had the time to reflect on what the
clothes felt like and to look at myself in the mirror. I
wanted to 'jack off' but restrained myself, as I was afraid
that might reduce my enjoyment. If the guys at the station
knew how much I liked these clothes they would never let me
live it down. I couldn't believe it myself. No wonder I had
enjoyed the feel of my chick's lingerie. I had thought it
was her body in satin but I was beginning to realize it was
as much the clothes themselves.
I pulled on nude pantyhose and sat down to do my make-up.
The lipstick was a subdued shade of crimson, which
complemented my dark hair. A hint of green eye shadow set
of my hazel eyes. I lined my upper lids and applied mascara
to my conveniently long lashes. After brushing my hair I
tied it up at the back of my head with a two inch wide
black ribbon. I pulled on a straight black skirt and
slipped on a crisp white cotton blouse leaving the top two
buttons unfastened.
I took a cab to the first of the clubs - The Changeling. It
had a boutique store attached where the members could buy
lingerie, jewelry and make-up. I browsed and bought a pink
satin baby doll. The owner had been watching me and when I
brought the delicate garment to the counter he said.
"Hi, that's very pretty. Are you new in town?"
"Yes, I came a week ago from Reno. I'd like to take out a
membership."
"Surely. You'll fit right in. I'll show you around. If you
come back tonight at 7.00 we will be having a 'Meet and
Greet' followed by a dance."
"Great. I'll be there. How often do you have dances?"
"Every night. Monday to Wednesday they are informal. On
Friday it is semi-formal and Saturday and Sunday they are
formal. That way our 'girls' can wear different outfits and
dresses."
The owner was a large man dressed in drag. He had on a long
brown wig, an emerald green dress with a flared skirt and
shirt top. I thought his make-up was a bit heavy but given
his masculine features it was maybe necessary. I felt quite
slender and feminine beside him.
He took me through the building, which was a big old
mansion. There were eight bedrooms, three with en suite
bathrooms. The beds, all king-size, were dressed in satin
sheets and covers. In addition there were three bathrooms,
two sitting rooms and a clubroom with a dance floor. It was
luxuriously furnished.
"This is wonderful."
"We have some very discriminating clients."
"But my fee is only $20. That's not very discriminating."
"Ah, we want to encourage pretty lady boys like you to
join. The heavy fees are paid by wealthy clients who want
to meet people like you."
"I see."
I suspected the 'wealthy clients' were from India and the
Middle East. It seemed that I had picked the right club to
begin my investigation.
"Do all the bedrooms mean that people stay over?"
"Oh yes. We have quite a few out of town clients and many
members like to have some private time in a discrete
environment."
"As tonight is Thursday the dance is semi-formal. Is it all
right if I wear a long dress? I don't have all my clothes
yet."
"Of course. The dress code is a minimum standard. Most of
the 'girls' prefer long gowns."
"Are there a lot of 'girls'?"
"It varies. At the moment there are twenty regulars."
We chatted for another ten minutes then I left. I checked
out the other two clubs but they were seedy and not likely
to be the front for a lucrative sex trade. At 4pm I was
back at my flat, undressed and soaking in the bathtub,
thinking about the evening. I was keen to try on the
taffeta dress as I had never worn a gown before but I was
also a bit nervous about dancing with other guys. It was
going to be an evening of firsts.
I put on the strapless bra, the garter belt and matching
thong. I did not bother to tuck my penis under my groin as
it was small and did not show. Opening the box I had bought
that afternoon I took out a panty-liner and fitted it
inside the front of my thong to catch the pre-cum, which
was already flowing copiously. I was learning fast that
cross-dressing was very erotic, a far cry from wearing a
cotton bra, a tight sweater and hot pants to nab a few
'Johns'. I was literally shaking as I readied myself to
slip into the shimmering taffeta dress. It was cool and
silky against my skin. As I walked in my stiletto heels the
skirt brushed lightly against my nylon sheathed legs and
rustled provocatively. It felt quite delightful. I slipped
on the bolero jacket and sat down to apply my make-up, put
in gold hoop earrings and fix a thin gold chain around my
neck. I constantly moved my legs to enjoy the feel of the
silky fabric against my skin. My panty-liner was already
wet as my stiff little penis oozed pre-cum in response to
this usual stimulation.
By 6 o'clock I was ready for work. I picked up the small
satin evening purse and made sure I had my credit card,
lipstick, eye shadow and mascara, some Kleenex and a spare
panty-liner. Ginny had loaned me a coat. I had told her I
was going out in an evening gown and needed something
suitable. It was a mid-calf length raincoat in a royal
blue, silky shimmering nylon. It rustled sexily against the
taffeta of my dress. I slipped the gold chain of my purse
over my arm and went out to the waiting taxi.
"Where to honey?"
"The corner of Young and First."
"That would be 'The Changeling'?" I had hoped he would not
jump to that conclusion.
"Yes. Very clever of you."
He looked at me through the rear view mirror and I felt
that I was being undressed. I blushed hotly.
"I guess it takes all sorts."
When we arrived he said,
"There you go, fella. Keep your panties on now, y'here?"
I paid him and quickly left the cab blushing hotly with
embarrassment.
I rang the doorbell and the owner, who introduced himself
as Francine, welcomed me. He was wearing a long black satin
gown.
"Come in, sweetie. Let me take your coat. Oh! My! You look
gorgeous."
He took my coat and opened his arms to show me his dress.
"See I wore a long gown so you would not be the only one.
By the way what is your name?"
"Leslie."
"Is that you real name or femme name?"
"My real name."
"Perfect! I always prefer it when real names double as
femme names. Now let's go into the club room and I'll
introduce you."
The room held about 30 people, mostly men. I was the tenth
T girl. The T girls were all young. One was Asian and two
were black. The men were all of Indian and Middle Eastern
extraction and looked smart and wealthy. I was certain I
had found the entry point of the trade.
Francine introduced me to everybody. The T girls were happy
and friendly. They all looked very feminine and pretty.
There was no trace of their maleness. Most wore cocktail
dresses but two were dressed like me in gowns.
The men wore suits or open-necked silk shirts. One had on a
tuxedo. Several seemed to be on friendly terms with the T
girls and flirted with them. The T girls seemed to like it
and there was a lot of touching and hugging.
One who introduced himself as Sully, offered to get me a
glass of wine. The conversation flowed easily and I quickly
relaxed. Sully paid special attention to me, as did another
Arab type called Ahmed. I found that the attention was
enjoyable and soon forgot why I was there. After two more T
girls arrived a DJ began calling every one to dance.
It had been easy to ask about the club and what people did
there. Several of the T girls talked about a training
school they had just graduated from. They referred to it as
'The Institute'. This was a finishing school run by a
Madame Jacqueline Black, who was apparently very strict but
the T girls all loved her. Those who had been there trained
to become 'maids' which was not a maid in the conventional
sense but one who had reached some very high standard of
femininity. Just as the conversation was getting
interesting Sully asked me to dance.
It felt strange dancing with a man. Eventually, my dress
and the heady atmosphere of a collection of pretty boys all
doing the same thing made me forget that I was a police
officer and enjoy being floated expertly across the dance
floor with the skirt of my gown billowing around my legs.
Sully held me close. His hand pressed against my lower back
and slowly slid down over my bottom. I felt his hard cock
through the material of my dress against my stomach. It was
curious to think that I was having this effect on a man. It
was quite erotic.
I placed one hand on his shoulder and he held the other. It
was a standard waltzing stance but when the music played a
slow dance the lights dimmed and he put my arms over his
shoulders and his own slipped around my waist and onto my
bottom. We were close and I began to have some doubts and
wonder why I was not repelled. After all, I had a girl and
was definitely not gay.
The next dance was also slow and Sully began to stroke me
and fondle my buttocks. He was getting very aroused and I
was getting worried. As the dance ended he cupped my face
in his hands and kissed my lips. This was too much. That
morning I was a regular guy and a few hours later I was in
a dress being kissed and fondled.
I broke away as politely as I could and excused myself to
go to the washroom. As I crossed the dance floor several
couples were kissing. There was sex in the air. In the
washroom I found an empty cubicle, pulled the skirts of my
dress up, slipped down my panties and sat on the seat. As I
relieved myself I became aware that there were two people
in the next cubicle and they were obviously having sex.
Effeminate moans and cries mingled with grunts and the
regular slapping sound of two bodies coming together hard.
I sat very still and listened as my cock throbbed. The
cubicle walls rattled and shook violently as the couple
reached orgasm. When they had climaxed I pulled up my
panties over my very stiff little cock, straightened my
dress and left the cubicle.
As I washed my hands and repaired my make-up the couple
came out. The T girl was a very pretty Asian in a short
black cocktail dress with an empire waist. The velvet
bodice was accented under his bosom with a black satin bow.
The skirt in black satin had a deep front pleat. He wore
fishnet stockings and black stiletto pumps. He was a sexy
thing all right. We smiled at each other as I left the
room. His partner had been a large athletic Sikh with a
black beard and immaculate purple turban.
Later, I saw the T girl dancing very closely with a good-
looking Arab. As I returned to the clubroom I saw Sully
move towards me but Ahmed intervened and asked me to dance.
I felt a little twinge of pleasure at the look of
disappointment on Sully's face.
Ahmed danced well and swung me expertly around the floor,
which was less crowded. Several couples had disappeared.
After three dances I saw the pretty Asian go up to the
bedrooms with the Sikh and the Arab. Ahmed was starting to
get amorous. I could feel his stiff cock against my stomach
as he crushed me against his athletic body. His hands
squeezed and mashed my buttocks and he began to nuzzle my
neck and ear lobes with his lips. It was time for me to
split. Ahmed tried to guide me up the stairs towards the
bedrooms but I said,
"I have to go now, Ahmed."
"Aw come on. Its too early."
"No really, I have to get a 6 O'clock flight." Just then he
kissed me on the lips and I had to push hard to break away.
"No, please Ahmed. I've had a lovely evening. Please don't
spoil it."
He let me go.
"Give me your phone number. I want to meet you again. I
gave him it. "But I shall be away for a week." I figured by
then he would have forgotten me and my investigation would
have been over.
I retrieved my coat from Francine.
"You're leaving early. Didn't you enjoy yourself?"
"Oh it was lovely, but I have to catch an early flight."
"I saw you with two of our wealthiest clients. You
obviously made a big impression."
"Francine, tell me about 'The Institute'."
"It's a training school for maids. Madame Jacqueline takes
pretty young men like you and turns them into very feminine
T girls. She teaches them all the feminine arts and they
learn to be demure and submissive. Many of our prettiest T
girls go on to interesting jobs that allow them to develop
a fully feminine lifestyle."
"What kind of jobs?"
"A variety. If you enroll in the Institute you will learn
all about it."
"Sounds interesting. I think I would like to enroll. How do
I do that?"
"Nothing could be simpler. She takes a new class every
month. The course lasts two weeks followed by a two-week
practicum. The next class starts on Monday. Call me
tomorrow and I will be able to tell you if she has an
opening."
"What does it cost?"
"$2000 but most of that is refundable under certain
conditions."
"Oh, such as?"
"You'll find out once your there."
"What is the practicum?"
"You'll find that out too?"
"Okay. I'll come and see you tomorrow. Bye."
"Bye, sweetie."
That night, as I lay in bed distilling the images and
sensations of the day I decided that it was not such a bad
assignment. Cross-dressing was surprisingly pleasant and
dancing with the two guys had been fun until they started
getting fresh. Women had to put up with that all the time.
It was interesting that I was able to turn men on. In
retrospect I decided I did not mind being kissed and fell
asleep thinking about what might have happened if I had
stayed.
The Institute
The following morning I put on a kilt in a beige and black
tartan. I wore the new black slip over my bra and panties.
Admiring the luster of the fabric as it flowed over the
curves of my body I ran my hands over my buttocks loving
the silky feel. I adjusted the straps so that the lace
bodice fitted neatly over the cups of my bra. My blouse was
a crisp black cotton, which I tucked into the waistband of
the kilt. Black pantyhose, black low-heeled shoes, and gold
costume jewelry completed my ensemble.
I had woken up feeling very horny after a restless night
thinking about the dance and my plans to enroll in The
Institute. It was going to be difficult to persuade Geoff
to advance me the $2000 but, if he would not, then I would
take it out of my savings. The prospect of two weeks of
exploring this new interest in my femininity was too
enticing to pass up. Anyway it was quite obvious to me that
the Institute was an important factor in the sex trade.
I slipped on the silky raincoat, smoothing the soft folds
and feeling the mounds of my bosom through the material. I
made a mental note to buy a coat like it for myself.
Even though I was nervous about showing myself at the
police station I had decided to wear drag to my interview
with Geoff so he would know that I was serious about
enrolling in the school.
Geoff did not recognize me at first.
"Holy shit! You look incredible."
"Down boy. This girl is not available." I laughed.
"So how's it going? Have you got anything for me?"
I briefed him on my investigation so far and told him that
I needed a $2000 advance to enroll in 'The Institute'.
"Are you shitting me?"
"I can pay you back. It's mostly refundable. I am sure the
school is an important link."
"What do you mean it's refundable? How does that work?"
"Well, I imagine that if I pass or do well it will be
refunded."
"What do you have to do to pass?"
"I don't know. But that's my problem."
"No its not. Its mine... till that money is returned."
"Hey, Geoff... I didn't want this assignment. Wearing drag
is not my idea of fun." I lied. I was finding an incredible
turn-on but he did not need to know that. I told him about
Francine's comments about the Institute and repeated how
important I thought it was to the trade.
"Yeah, well, I guess you're right. But make sure you get
the money back!"
He cut the check and I folded it and cheekily tucked it
into my bra.
"Jesus! Get out'er here before I forget you're a guy."
I left his office feeling pleased with myself. On my way
out I got several appreciative looks from colleagues who
did not recognize me. Instinctively, I wiggled my bottom,
and sashayed out of the building enjoying the feel of my
kilt swishing against my legs.
I returned to 'The Changeling" and Francine told me there
was room for one more student. He handed me the long
application form and I paid over the money. The form asked
for all my vital stats, details of my interests, my sex
life and sexual preferences, whether I had a current
girlfriend or boyfriend. I wanted to make sure that I was
accepted so I answered as if I were the most committed
transvestite, even going so far as to say I dreamt of
having a sex change. I was accepted after Francine had
faxed my application to Madame Jacqueline. She called him
back and, as I browsed through the boutique picking out a
pretty satin bra made by 'Caress', which I decided I
needed, I overheard him saying,
"He's gorgeous! Girls would die for his legs and tush,
which I noticed both Sully and Ahmed could not keep their
paws off... Yes, he seemed to like it... He kissed like a
teenage girl out on her first date... Ahmed spoke to me
afterwards and said to make sure I got Leslie into the
Institute... No you won't regret it... Tony can go next
time... Okay darling, love and kisses."
I paid for the bra and Francine told me to be at the store
by 2pm on Sunday. He was taking myself and three other new
entrants out to the school in a mini-van. He gave me a list
of clothes, accessories, toiletries and make-up to bring
along.
I spent the afternoon shopping for the items I needed. I
made a big hole in my savings but I was hooked and there
were just too many exciting clothes. It did not help that
some of the shop assistants easily made me believe how
pretty I would look in a certain dress. Except for two
dresses the clothes I bought were all lingerie and
sleepwear. Apparently, the school also had an extensive
wardrobe for outerwear and a wide selection of specialized
underwear.
Despite myself I was excited and that night I jacked off
twice as I mulled over the events of the last two days,
always coming back to dancing and kissing with Sully and
Ahmed. Obviously, that did not repel me and my fantasies
about those two were becoming bolder. I figured this was
part of the process of rationalizing and accepting my new
persona and the novel experience of cross-dressing. I was
to do a lot of that in the next few days.
On Saturday I stayed mostly in my apartment trying out
various combinations of outfits and trying not to 'jack
off' too much. I went out in the afternoon and bought two
more tubes of lipstick and an eye shadow pencil. I also
added another $300 to my visa buying a second evening gown
so that I could attend the dance at the club in something
different. This was a full skirt in scarlet satin with a
black lace long-sleeved top over a black satin camisole.
The waistband was a wide black satin cummerbund finished in
a large bow at the tummy.
The stiff, heavy couture satin skirt felt thrilling and I
was in a high state of anticipation when I arrived at the
club. Francine, in a dark blue taffeta shift, welcomed me
with a big hug. Many of the same people were in attendance
including Sully and the Asian T girl with a new partner, a
good looking black guy. Sully booked me for the first few
dances but I was also waltzed around the floor by the tall
Sikh who I had caught banging the Asian T girl and, a very
macho, light blonde, Scandinavian guy.
It was an exciting evening and there were several times
when I had to defend my virginity. Sully, of course, kissed
me several times and I had an opportunity to test the
soundness of my fantasies. Maybe it was the dress but I
enjoyed being kissed, so much so that I let him sit me on
his knees in an armchair while we petted open-mouthed. He
twisted around and pushed me against the back of the chair
and tried to put his hand up the skirt of my dress but I
did not allow that. Even so for 30 minutes we engaged in
some very hot petting and I was very horny.
We were not the only ones engaged in intimacies. It was
that kind of party where couples paired off and danced
suggestively, necked and disappeared into a bedroom. Few
people remained with the same partner. I had at least one
dance with all of the guys. I got to know Lei, the Asian T
girl. We went to the bathroom together to repair our make-
up and I learned that he was an escort attached to an
agency that catered to specialized tastes. Many of the
other T girls were moonlighting as escorts. This accounted
for the trips to the bedrooms. T girls like me were usually
left alone unless we wanted to go all the way.
The Sikh danced very suggestively keeping our bodies
pressed together and grinding his crotch with its erection
against mine. We reclined on a sofa for twenty minutes of
heavy petting. But it was the Scandinavian, Karl, who was
the boldest. He accosted me outside the bathroom and kissed
me hungrily. We had danced together three times, all slow
sensual dances before I had gone off to the bathroom. He
followed and embraced me as I came out of the room.
Naturally, I kissed him because he was very attractive and
I was now very much into kissing.
As we kissed he ground his stiff cock against my groin. I
could feel it through the folds of my dress. I liked that.
It kind of validated my femininity. But I resisted when he
took my hand and rubbed it against his groin. I pulled it
back but not before feeling the unmistakable shape of an
erect penis. He responded by hitching up my skirt and
stroking my upper thighs, clasping the bulge in my panties
caused by my much smaller hard penis. He squeezed and
stroked it slowly.
I was shocked and tried in vain to pull away his hand. All
the while I could not make a noise as his mouth covered my
lips and his tongue filled my mouth. Other guests walked by
us as we were locked in this sexual struggle but nobody
interfered. He was very strong and I realized that I could
not prevent him from having his way. Well, that was not
exactly true. I was proficient in self-defense and could
have had him on his back in seconds but that would have
blown my cover. So I tried to mitigate the damage and
resisted without stopping his exploration.
Despite trying to stop him I still found the situation
erotic so that when he forced my hand back onto his crotch
I felt a tremor of desire shoot through me. He rubbed my
hand over the bulge in his pants and I felt the thick hard
cock and the softer testicles. It was very intimate and my
resistance weakened. Accordingly, even through I was firmly
trying to restrain his hand, which clasped my crotch he was
easily able to pull down my panties, and continue to fondle
my penis and testicles.
Never had anyone ever touched my genitals and so to have it
done to me while in a dress and being kissed was extremely
erotic. It was a delicate moment. My legs felt weak and I
knew that I was approaching an important threshold. My
resistance diminished as his hand slowly moved up and down
against my groin. He moved his lips off mine and kissed my
neck. I no longer wanted to cry out. He suddenly turned me
and bending me forward raised my skirt up to my waist. I
felt his hand fumbling wetly between my buttocks at the
same time as he held my hips firmly with one arm.
I was incapable of stopping whatever he had planned but
Sully interrupted him by coming between us and carrying me
away onto the dance floor. As we danced I realized that I
had come very close to being penetrated. I was grateful to
Sully and held him close. I did not realize it at the time
but he had already decided that I was to be his property. I
took the opportunity to make my exit. We had two more
dances and then I used the old feminine standby of the
headache.
When I got back to the apartment I felt very pleased
myself. Obviously, Karl had taken my enthusiastic kissing
as encouragement so I could not blame him for coming onto
me so strongly. I found it exciting that I was so
desirable. The attention had reinforced my femininity. The
dress had felt gorgeous and was the perfect costume for all
the dancing and kissing. My fantasies ran riot as I tried
to sleep.
On Sunday, I put on a long crossover summer dress in olive
silk with floral details, nude pantyhose and olive mules. A
string of pearls around my neck and pearl studs in my ears
and I was ready to go. I lugged my two suitcases down the
stairs to the waiting cab.
Two others had already arrived. Patsy (otherwise known as
Patrick) and Frances, like me, with a dual-purpose name.
They were both very pretty and very excited. Frances was
black with skin like velvet and a gorgeous figure. Patsy
was Asian, very petite and vulnerable looking. The fourth
member of our troupe arrived five minutes later. Staci, an
attractive blonde with sensuous lips and lovely 'doe' eyes,
bustled in apologizing for being late.
Francine helped us load our things into the mini van and we
set off. We chatted excitedly about the school. The other
three knew more than I and Francine filled in some of the
gaps in our knowledge. The course was in two parts. The
first week was devoted to learning how to do a whole range
of feminine things - mixing and matching clothes, putting
on make-up, jewelry, personal hygiene, walking in high
heels. Then there were crafts like sewing, flower
arranging, tying scarves, etc. While this was going on we
were expected to keep our rooms and clothes clean and tidy,
share in chores around the school, act as ladies maids for
Madame and her helpers (who were all TGs). That included
bathing them and helping them dress. Above all we would
learn to be submissive and feminine.
They were quite vague about the second week. The consensus
was that there was to be more of the first week only
stricter and more intense.
We arrived punctually. The school was in a beautiful
country mansion set in its own grounds and surrounded by a
high wooden fence. The furnishings were luxurious and, like
the house in the city, there were many bedrooms. Obviously
this operation was making money.
The car stopped at the front entrance and three attractive
T girls in tight fitted taffeta skirts and silk tops came
sashaying out of the building on what looked like four-inch
stiletto heels. They wore little hats with veils and white
satin gloves. They were the epitome of femininity.
They made a fuss about trying to help us with our luggage
but their heels and tight skirts made help impracticable.
There was a lot of giggling and squealing but a very well
built man, who I learned later was called Joe, did all the
work. He hefted our suitcases as though they were filled
with feathers. We followed the T girls into the house to
meet Madame Jacqueline.
Madame was an attractive woman in her 40s. She was smartly
dressed in a tight navy satin skirt, black patent pumps
with tall polished brass stiletto heels, a white satin
blouse and a black satin hat with a veil. She carried a
cane wrapped in a black ribbon. Later we learned that she
used this when a student required severe correction.
Madame welcomed us and introduced the T girls as her
helpers and our trainers, Jackie, Tiffany and Nicola.
"Girls take the students up to their rooms and help them
unpack. Then they can change into something formal and we
will all gather for supper and have a nice talk. Off you
go."
We were placed two to a room and the rooms were on either
side of a large bedroom which one of the T girls who helped
Madame used. I shared a room and a double bed with Frances.
The room was a girl's room. Pink and gray antique satin
curtains, ruffles and frills decorating the dresser skirt
and the satin bedspread. The bed sheets were pale blue
satin. The wallpaper was flowered and there were two
pictures of Victorian girls in long dresses picking
flowers. There were teddy bears and dolls in frilly dresses
set on shelves under the window.
We unpacked, hanging our dresses, skirts and blouses neatly
in the closet. Tiffany showed us were the iron was so that
we could restore our outfits to a pristine smoothness. We
each took a drawer for our lingerie and another drawer each
for sweaters and tops. We chattered the whole time admiring
each other's choice in clothes.
We were kept so busy at the Institute that there was only
time to make friends with one's roommate. Even though I
would see Staci and Patsy around it was only Frances that I
became truly a friend of. We were both virgins and nervous
but excited about the course. Like me Frances had not been
cross-dressing for long but once begun had fallen in love
with feminine clothes.
After arranging our clothes and settling into the room we
showered and changed for the supper. We were both shy about
undressing in front of each other. The bathroom was down
the hall and I went first having taken off my kilt and
blouse and slipped on a red satin housecoat, which was one
of several items that the Institute supplied. I went into
the bathroom undressed and showered than putting the
housecoat over my naked body I went back to the bedroom.
Frances was not in so I perfumed my body and brushed my
hair before picking out a pretty bra in flesh colored nylon
spandex embroidered with blue satin. I had decided to wear
the peacock taffeta gown with the bolero jacket to supper
and this gave me the right amount of lift to show some
cleavage above the bodice of my dress. I was adjusting the
straps when Frances walked in and saw me completely naked
except for my bra. I quickly covered my sex with a hand. It
was stiff as always and I blushed with embarrassment.
"Oh sorry, Leslie. I didn't mean to surprise you."
"That's alright Frances. I suppose we should get used to
seeing each other undressed as we are going to be changing
in here a lot."
"You're right." He quickly undressed to reduce my
discomfort. His body was slender and shapely. His black
skin was somewhere between velvet and satin. The only non-
feminine attributes were his flat chest and a penis that
was twice as big as mine.
"You have a lovely set of buttocks Leslie and I wish my
thing was small like yours. I hate my big ugly one."
"Oh Frances, don't worry about that. You have gorgeous
skin. It's just like satin."
This was the beginning of a mutually supportive
relationship.
I finished dressing while Frances showered and when he
returned he said how beautiful I looked in my gown. I
helped him dress in black satin body shaper and a dreamy
black satin strapless gown with an A line skirt.
"Frances, you look simply divine! Oh I could kiss you!"
Frances held out his arms and we kissed. It was lovely
holding him in his satin dress our bosoms pressed together.
Of course, it was not a sexual kiss. We were just two
sissies, our hearts bursting with the excitement of wearing
lovely gowns, and showing our affection.
At the supper table Joe and two other men who turned out to
be Derek and Jake served us. They were all big, muscular
men, built like Greek gods, who oozed masculinity. They
wore black pants, white shirts and black bow ties. Staci
and Patsy became quite distracted when we were introduced
to them. All were over 6' 2" with very muscular bodies. We,
on the contrary were between 5' 2" and 5' 5" and very
skinny. Besides intimidating us with their physical size
they literally oozed masculinity. Even I who was
uninterested in them as sex objects found them attractive.
Staci and Patsy could not keep their eyes off them and
often found opportunities to touch them. I could not tell
what Frances thought as he was so shy. I soon realized that
they were part of the program. Their masculine presence
served to remind us that we could not compete, if we wanted
to, in the maleness department.
We talked till 10pm with Madame and her helpers explaining
the rules and the course.
Each day would begin at 5.30am with a five-kilometer run
with Jake, the resident Phys Ed instructor. Madame insisted
on all her T girls having very fit and trim bodies. This
was not a problem for me as the police training kept me in
good shape. We also had to do a strenuous series of
stretching exercises. Staci said that was so we could do
all of the Karma Sutra positions. I thought he was kidding.
After the run there was a shower, change into our maid's
dresses, put on make-up and have a light breakfast. By
7.00am we were supposed to be ready to assist Madame and
her helpers to bathe and dress.
Madame was very strict and any sign of maleness would be
punished with a spanking. Sloppiness and untidiness were
also severely punished. Body hair was absolutely forbidden.
Again I was lucky as I had very little and had not started
to shave. We all had to shave off our pubic hair. Madame
said this was so we could wear high cut panties and
swimsuits.
Sex of any kind including masturbation was strictly
forbidden. We could give each other chaste kisses and hugs
but nothing more. Staci and Patsy both groaned at this.
They were both sexually active and said they would not be
able to sleep at night without a man beside them.
The best student after two days would become Madame's maid.
Students were ranked by uniform. We would all start out in
gingham maid's dresses and graduate to taffeta. Only
Madame's maid would wear a satin uniform.
This was exciting stuff and we all found ourselves
determined to win the satin dress. At the end of the week,
on Saturday night, we would 'come out'. There would be a
wedding ceremony at which we would each be attached to a
partner. Madame would select our partners. The next day we
would spend at a secret honeymoon hotel and return to the
Institute on the Monday to begin the second part of the
course. This was thrilling news. Wearing a wedding gown is
every cross-dresser's dream. The Institute had a large
selection of gowns and honeymoon outfits and we would be
able to help in the planning.
Before the wedding, on the Friday, we would select a stream
to go into for the following week. There were four - the
'spinster', for the T girl who just wanted to be a woman,
the 'maid' for the T girl who wanted to become attached to
a mistress, the 'wife' for those who wanted to find a male
partner and the 'courtesan' for those who wanted to become
escorts. Patsy and Staci wanted to be courtesans, Frances
wanted to be a wife and I said I would be the spinster.
Madame said that most students chose to become escorts and
a few became wives. I would be the first spinster. The
others all laughed.
"I think what he is saying is that you'll probably change
your mind." Said Patsy.
"No I won't, you'll see. I'm not gay. I like girls but I
also like dressing as one."
"I saw the way you kissed Sully last night." said Madame.
"Well, that's all we did... and... maybe I liked it a
little."
"What happens to the escorts when they have finished the
course?"
"Some stay in the city and join agencies but most go
overseas."
"Really, why is that?" This was getting interesting. I was
surprised Madame was admitting it so easily.
"There's a big demand for T girls. In some cultures men
prefer males to females for fun sex."
"Do the T girls want to go to another country?"
"Certainly, nobody is forced to go... or to be an escort
for that matter."
This was not what I expected to hear and I doubted the
truth of it.
The course would end with a gala ball and we would be the
stars in white satin ball gowns. Ex-graduates and
'suitable' male partners would attend. The best student of
all would win a little prize.
It had been a long day full of excitement. By ten o'clock
we were getting tired and Madame reminded us that we had to
be up early for our first run. We went up to our bedrooms.
Frances and I said good night to Staci and Patsy and closed
the bedroom door. We slipped out of out dresses and while
Frances put on a pretty pale blue chiffon baby doll I
slipped into a new red satin chemise. After brushing each
other's hair we snuggled between the lovely satin sheets,
whispered good night and quickly fell into a happy sleep.
Training
We were all up at the sound of Jake's whistle. We all
quickly pulled on cotton exerciser bras, cotton briefs, T-
shirts and blue satin hot pants and followed Jake along
five kilometers of country lanes. Staci and Patsy kept up a
steady stream of superlatives about Jake's body until they
were too puffed to talk.
After showers we dressed in gingham maid's outfits with
white organza aprons and caps. Under the dresses we wore
crinolines and corsets laced very tightly. When we were
first dressed in the uniforms there was a little ceremony
when our genitals were tied into bags made of satin and
trimmed with lace and little bows. The message was that
these remaining signs of maleness were being retired.
We spent the day cleaning and studying make-up and hair
design plus waiting on tables. We also bathed and dressed
our T girl helpers twice. We were all spanked several times
for clumsiness and forgetting our femininity. It was not a
frightening experience. We would have to bend over our
helper's knees and have our skirts and petticoats raised
and panties pulled down. Our helper would then spank our
bottoms with a paddle. It hurt but in the circumstances the
stinging sensation was pleasantly erotic. We all misbehaved
deliberately and the helpers enjoyed spanking us. Bending
over Jackie's knees I would hold his nylon-sheathed legs to
steady myself - and enjoy the feel of his silky legs.
The school was perfect for me. I was hooked on cross-
dressing, indeed, I had moved beyond it and, as I was to
learn during the week in many discussions about
'transgenderism', I was quickly acquiring most of the
characteristics of a committed transsexual. As we only had
to wear our maid's uniform while we were doing our chores
for the rest of the time we could raid the Institute's
large closets and try on a wide range of gorgeous dresses,
skirts and blouses, suits and, of course, lingerie. This
was perfect for me. I had no sooner become used to one
outfit than I found myself planning what I would wear next.
Male clothes had never interested me and it was rare for me
to change more than once a day. But I now changed five or
six times a day and each change was an erotic adventure.
We were all young and at our sexual peak. Underneath our
lingerie we were biological males with enough testosterone
in our systems to give each of us a strong and promiscuous
appetite for sex, although in Frances and I it was
repressed. I was constantly horny but frightened of sex.
The memory of Sully, Ahmed and Karl had faded.
Living in an environment where we were expected to act like
women merely heightened our sexual curiosity and provided
an almost constant source of stimulation. Part of our
feminization training was to encourage us to express our
feelings more. When we were happy we were taught to show it
by squealing or giggling and by hugging and kissing. If we
were spanked or otherwise made unhappy we let ourselves cry
freely and comforted each other with more hugs and kisses.
The helpers were our trainers and delivered praise and
spankings. They were graduates of 'The Institute' who had
worn the satin uniform and been Madame's personal maids as
students. They were all courtesans and very pretty and
feminine. As maids we had to bath and dress the helper who
had been assigned to us. Jackie was assigned to me and I
quickly came to adore him. His dark skin was like
Frances's, as soft and smooth as satin. He had long wavy
hair, dark eyes and thick red, kissable lips.
Bathing and dressing him was fun. He loved to fool around
and for me it was the first time I had been so close to a
naked male. His body was slim and lithe. He was not on
hormones so he had no breasts (like Tiffany and Nicola) but
his buttocks were plump and rounded like a girl's. His
penis was much larger than mine, which, I discovered in
that first week, was unusually small. When I washed his
penis it quickly became erect. He liked me to spend a lot
of time on his genitals but he made it so much fun that I
quickly overcame my reserve about touching another man's
sex.
"Umm, that's nice honey... Oooo, you have a nice touch...
Ummm, that's it don't forget my love entrance."
"What's that?" I naively asked the first time I bathed him.
"My asshole sweetie, make sure it's clean. Its gonna be
having some visitors."
"What do you mean?"
I was soaping the long thick shaft of his stiff ebony penis
and spreading the soap over his testicles. He guided my
hand to his anus and made me insert my finger. As I did it
he cupped my face and kissed me.
"Honey, don't you know anything? How do you think us T
girls get banged up?"
I remembered how Karl had bent me over from behind and
pulled up my skirt.
"You know you look especially nice when you blush."
I told him about my encounter with Karl.
"Eew, that sounds like you were about to get plugged
honey." I blushed again and he kissed me again.
"Don't worry honey, you'll like it!"
"Oh no I won't. I'll never do that. I have a girlfriend."
"Sure honey."
I would dry him and then help him dress. He had a big
collection of dresses and gowns and a bigger one of
lingerie. As we were the same size he would let me borrow
his clothes. Usually, as I picked out a bra or slip for him
to wear, I would find some article of clothing that would
appeal to me. So these sessions became dress up time for
both of us and I would take off my maid's uniform and try
on one of his dresses. This became the pattern until I won
the satin dress on Thursday and became Madame's maid.
Because of the intimacy, a lot of sexual tension built up
between our helpers and us. I was amazed at how quickly I
wanted to embrace and be kissed by Jackie. By the second
day I had fallen in love with him. The others had done the
same with Tiffany and Nicola. We were all in love with
Madame. Consequently, we worked hard to please them. They
would use kisses as rewards. As the week progressed and we
improved there were more and more kisses. As long as they
were feminine expressions of affection they were permitted.
Sometimes it went beyond that as the helpers were, like us,
young horny males and all were pretty. When Madame caught
us kissing our trainers in a sexual way, she would make
them spank us till we cried.
Not that I ever did - kiss in a sexual way, that is. I was
reserved towards the men and drew a firm line between
affectionate kisses with the other sissies and the
blatantly sexual necking that I often caught Staci and
Patsy engaged in with Derek, Joe and Jake, who lurked
around the place and showed up at suspiciously convenient
moments to throw out temptation. Staci and Patsy were quite
shameless.
In addition to our intimacy with the trainers there was a
growing sexual tension between Frances and I. We shared
rooms and slept in double beds between satin sheets in sexy
baby doll nighties. A growing intimacy was impossible to
avoid.
To add to the temptation of the shared bed and sexy
lingerie was the fact that our room and that of Staci and
Patsy were on either side of Tiffany's bedroom. Tiffany was
a gorgeous Asian with long, black, silky hair. Every night,
except for the first, Tiffany, Nicola and Jackie would
entertain clients until one or two in the morning. The
walls were thin and allowed even whispers to be heard.
Thus, after going to bed the second night both Frances and
I were woken up by noises from the middle room.
"Oh! Yee...es. Oh that's soo good... Ummph! Fuck me...
uuuugh... Uuummm!"
Tiffany's falsetto voice cried out. We could hear the
grunts and low pitched gasps of Tiffany's partner. On the
fourth night there were two male voices and on the sixth
there were at least three. The bed shook and creaked. We
could hear sucking and squishy sounds and the smacking of
bodies coming together. This would typically last an hour.
Then the door would open and close as they left the room.
Thirty minutes later more voices would return and
lovemaking resumed. It made both Frances and I unbearably
horny. When we went to the bathroom we could hear similar
activity from Nicola and Jackie's bedrooms across the hall.
On Wednesday night when I got up to go to the bathroom I
received a surprise. I was dressed in a pink organza, baby
doll trimmed with a satin ruffle and a large satin bow at
the cleavage. The panty was little more than a G-string.
Jackie had lent it me and I thought it was adorable. As I
came out I bumped into a naked man who I supposed was a
client of one of our trainers. His penis was semi-erect and
glistened slightly from lubricant. I could not help myself
looking at it as we faced each other. I blushed and tried
to pass him but he blocked my way.
"Well, aren't you a sexy little piece."
He clasped me in his arms and drew me tightly against his
body kissing me hard on the mouth. His hand slid over my
bottom and his finger pressed between my buttocks and
against my anus as he raised me off my feet and pressed me
back against the wall. We wrestled for a long minute as I,
frightened by the aggressive come on, pushed hard against
his chest. I could feel his penis against my leg, cool from
the remnants of the lubricant on it and, as it stiffened,
the shaft scraped up the inside of my thigh until I could
feel it pressing against my testicles. I could not make a
sound while his mouth covered mine. He was trying to push
his tongue between my lips but I kept them firmly closed.
It was when he raised one of my legs by hooking his arm
under it and tearing at my G-string that he broke the kiss
and I cried out.
"No! No! Stop it... Please... Nooo!"
The tip of his penis was pushing between my buttocks when I
heard Jackie call out sharply.
"Get your ass in here shit-face. I'm the one you're
supposed to be fucking."
He dropped me and I ran into my bedroom as Jackie, looking
resplendent in a white silk chemise and no panty held his
client's cock and dragged him back into the room.
Trembling, I slipped back into the bed. I learned that as a
pretty, lady boy I was vulnerable and my male instincts
were no protection. I would need to develop some feminine
defenses. Frances snuggled up to me and we held each other
as I told him what had happened. He was as frightened as
me.
Baby-dolls were de rigueur sleepwear for the students. They
were feminine and sexy, adorned with ruffles, ribbons and
bows. If we wandered around in them we had to wear high-
heeled marabou mules on our feet. Those of us with long
hair tied it back with a ribbon at night. We were also
encouraged to wear ribbons in our hair during the day. I
liked tying my silky locks back with a large satin ribbon
tied in a big floppy bow when I had on my uniform. This was
acceptable as an alternative to a maid's cap.
After the first day of feminization training we all felt
sexy, horny and deliciously feminine. We remained in that
aroused state for the rest of the week. By Thursday, it was
so intense that we were almost feverish. Masturbation
hardly helped. We all did that - usually at night to the
accompaniment of Tiffany's cries from the middle room. The
first night we suffered in silence but the next night
Frances and I hugged each other. Soon we were kissing and
rubbing our bodies together to the sounds of one of Tiffany
being fucked hard. In the midst of our petting Madame
walked in and gave us both a spanking for breaking to rule
against sex.
After that we would wait until Madame had inspected and
then snuggle up together. As the cries and moans and the
heavy slapping and shaking sounds came through the thin
wall we kissed passionately, rubbing our unbearably stiff
penises till they spurted warm slippery cum into our hands.
It never went beyond masturbation but we came three,
sometimes four times each night. We were two pretty,
oversexed lady boys and this nightly petting forged a close
and tender friendship.
Staci and Patsy were more advanced. They dressed to attract
men and they made no bones about their intentions to get
laid. Braver than Francis and I, they were adorably
mischievous and frequently got spankings for throwing
themselves at the three resident studs. They were always
caught and never completed the sex act but they kept
trying. At most they engaged in oral sex. I found that out
when I was alone with Staci.
We were picking flowers to practice our arranging skills.
It was the third day of the course and we had graduated to
taffeta uniform dresses. Mine was pale yellow and Staci's
was pink. As we chatted and fussed over the flowers our
dresses, flared out stiffly by taffeta crinolines, rustled
sexily. Our aprons were stiff, white organza. Underneath we
wore satin and lace lingerie that was a transvestite's
dream. We were discussing our underwear.
"Nicola lent me an adorable lace demi-bra that doesn't
quite cover my nipples. I love the effect under a silk see
through top."
"It sounds yummy. Jackie has this gorgeous pink teddy in
satin and lace. I tried it on this morning. I think teddy's
were invented by the devil because it made me feel
incredibly horny."
"Umm, me too. Have you got it on?"
"I did until lunch time when I changed into a satin shelf
bra, matching G-string and garter-belt and a divine satin
chemise."
"Oh that sounds gorgeous. I haven't tried a shelf bra yet.
Talking about horny, I think I will burst if I don't soon
get laid. Do you ever think about having a man?"
"Oh no. I love dressing as a woman but men are not my
thing."
"They're definitely my thing. Look here comes Derek. Isn't
he gorgeous? Just look at the muscles under his T-shirt
and... OH! That bulge in his crotch. He kissed me
yesterday, you know."
"No?"
"Umm. I was out here waiting for Nicola to come up for his
bath. Derek was spraying some flowers. I asked him if I
could try it. Naturally, I pretended to be clumsy so he got
behind me and helped hold the hose. His other hand, having
nothing to do, explored under my skirts..." We both
giggled. "I helped by guiding his hand to all the
interesting parts. I soon dropped the hose and turned to
kiss him. We kissed until Nicola came out and separated us.
I got a good feel of the bulge."
"Staci! You're so naughty! Did you get a spanking?"
"Oh yes, but Nicola and I both enjoyed it. I bent over his
knees while Derek held my skirts up and Nicola got him to
pull down my panties. I think he spanked me too. It was
nice."
Derek approached us.
"Hi Derek, I'm very disappointed in you."
"Why is that Staci?"
"Because you helped Nicola spank me yesterday. I thought
after we had kissed you were on my side."
"I am on you side Staci but you know the rules. I have to
help the trainers. Will a kiss make it better?"
"Maybe."
They kissed passionately and noisily for about five
minutes. He was a big man and Staci looked diminutive in
his arms. I saw Staci unfasten Derek's belt and pull down
his slacks. Derek was wearing a silky, blue nylon thong,
which accentuated the bulge in his crotch. Staci's fingers
fondled this mound and slipped inside the waistband,
pulling out Derek's soft but very big penis. It was much
bigger than Jackie's. I gasped when I saw it. Staci knelt
down and sucked this phallus quickly bringing it erect so
that it stood out a good eight inches. The shaft was very
straight and stiff and his large testicles hung from the
base.
Derek stroked Staci's hair and guided the pretty boy's head
as the full red lips slid along the length of his shaft.
Staci took the whole length down his throat, opening his
mouth and making a funny swallowing sound as the big penis
entered him and stopped when Derek's testicles bunched
against his chin. As Staci performed this fellatio on him
Derek beckoned to me to join them. I could not move being
transfixed by this novel and extremely erotic sight. As
Staci pulled back drawing the shaft out of his throat and
mouth he pressed the cock back against Derek's stomach and
sucked the testicles into his mouth and rubbed them with
his tongue, then licked the length of the shaft before
taking it down his throat again.
Derek looked at me with a faraway look in his eyes.
"This is how you suck cock, Leslie. Watch carefully. Let
Staci be your teacher... Uughh! That's good, babe... Ohhh
yee...es."
Staci was really sucking hard and fast. I heard the sound
of high heels approaching and saw Tiffany. Derek heard too
and motioned to Tiffany not to interrupt. Tiffany paused
and pretended to examine some flowers. Staci masturbated
the slick head of Derek's cock as he sucked the testicles
then deep-throated him twice more.
"Okay baby, this is what you want... open your mouth
wide... that's it... Ugh! Uuughhh!... Ummph."
Staci had his mouth wide open and his tongue stuck out as
he quickly sucked then rubbed the cock head. A spurt of cum
shot onto his cheek and left eye before he brought the tip
of Derek's cock onto his tongue and ten more spurts of
thick, yellowish cum spurted and gushed over his lip into
his mouth. As Derek finished Staci took his cock into his
mouth and sucked and licked it clean swallowing the puddle
of semen on his tongue.
Now Tiffany approached and pulled Staci off Derek who
strolled away tucking his big cock into his pants. Staci
had to bend over Tiffany's knees while his white, satin tap
panties were pulled down. The ivory globes of his tush were
framed prettily in the ruffles of his dress and petticoat
and the white satin of his garters tightly stretched over
his buttocks. The pretty little sissy squealed and wiggled,
as his soft globes turn pink under the impact of Tiffany's
hand.
It was just another in an increasing number of erotic
scenes and incidents that kept me in a nervous state of
arousal. I sensed that these sexual encounters were
orchestrated and were building towards some climax. Even
the shy Francis was becoming bolder. Our nightly trysts
were more passionate. On Wednesday afternoon, I caught the
pretty, black sissy helping Jake polish the car. Jake stood
behind Francis with one arm around his slender waist while
his other 'guided' Frances' hand as it rubbed the chamois
over the hood of the car.
Frances was wearing a mid-thigh length dress with a flared
skirt, nude stockings and white stiletto sandals. The white
against his soft black skin was devastatingly attractive.
As I watched them Jake's 'guiding hand' slipped under the
skirt of his dress and moved up Frances' thigh raising the
skirt and exposing the tops of his stockings attached to
his yellow lace garters. Frances pressed against the phys-
ed instructor's hard body and bent his head back as Jake
pressed his lips into the nape of Frances' neck. Jake's
hand continued up Frances' thigh and over the front of his
panties, cupping the mound containing the sissy's sex.
Frances twisted his head to kiss Jake and I saw his lips
part and Jake's tongue push between them.
That was the moment when Nicola came out and stopped the
petting, giving Frances a little light spanking on his
plump bottom making his buttocks bounce enticingly. That
night as we kissed and cuddled I told him I had seen him
with Jake. He signed and said that Jake could have done
anything with him.
On the Thursday, because the weather was hot, Jake had us
all in the pool swimming lengths. Physical exercise was
always mandatory, quite rigorous and, in addition to the
morning run, Jake could order some workout at any time he
chose. Then we would have to drop what we were doing and
change into shorts and T-shirts or swimsuits. Our thin
bodies were our most valuable assets. We were weighed every
day and five extra pounds were grounds for expulsion from
the Institute.
On this occasion we wore skimpy bikinis with under-wired
'A' cups (so that we could dispense with our breast forms).
After we had completed 50 lengths we were allowed to play.
Staci and Patsy flirted shamelessly with Jake and
frequently touched him. The two bold sissies splashed him
until he chased them. After easily catching them Jake
picked them both up in his arms as they squealed with
delight and hugged him in mock fear. He ducked them several
times causing them to hug him harder. Frances and I watched
with interest as the play became increasingly sexual.
The three of them eventually got out of the pool and lay on
a towel. Jake reclined on his back contentedly, his hands
inside their bikini bottoms, as Staci and Patsy moaned and
kissed him madly.
Francis and I looked at each other feeling very aroused as
Staci pulled down Jake's thong and popped out his penis.
Patsy and Staci grasped this enormous phallus and ran their
fingers along its length paying particular attention to the
spongy tip and the testicles. It quickly hardened and
pressed back stiffly against his flat stomach.
Once again my battered masculinity shrank as I compared the
equipment of a real man with my tiny penis, a mere two
inches long erect and with testicles no bigger than grapes
growing like unformed buds from the base of my shaft. I
wondered if I really should have been female. My long brown
hair tied back with a wide, red taffeta ribbon, my slender
body with plump, rounded buttocks and shapely legs, my
feminine features with full, sensuous lips and eyes like
deep dark pools were the attributes of an attractive femme
body. My maleness increasingly stood for inadequacy and
embarrassment. My femininity on the other hand placed
desirability at the center of my self-image.
Frances took my hand.
"I know what you're thinking. You and I were never meant to
be men and we shouldn't try to be. Let's enjoy the bodies
we have been given." I smiled.
"You're absolutely right but no girl is ever going to want
us now."
"That's true but I bet lot's of men will. Don't you have a
girlfriend?"
"Yes, but I haven't thought about her since coming here.
Sex with her was so easy but men scare me. I'm not sure I
will like doing it with them. Men never interested me at
all but as a 'woman'... you know what I mean?... I think
I'm getting interested. They