Crossdresser Porn Story 1. free porn video

Ray Hirsch sat at a desk filling out form after form.
It was amazing, the information that an employer
required before you could start working at a new job:
health insurance forms, Social Security, etc., and etc.
He was now filling out a questionnaire on his
background which would be used to conduct a security
investigation, since his work might involve working on
classified government projects. He stopped for a minute
at the question: List any aliases you have used.

“I wonder if I should put down Rachel?” he thought.

Ray quickly dismissed the idea. No one could possibly
know about her; Rachel was his little secret and she
would stay that way. Among his many other
accomplishments, Ray was quite the practiced
transvestite and Rachel was his sobriquet when dressed.

He found himself wishing he could dress up tonight, but
all of his things were packed away on a moving van that
was probably passing through Omaha, while he was
staying in a motel here in San Jose. He told himself
that he would have a place soon enough and then he
could be Rachel every night and on weekends if he
wanted. He turned in the stack of forms.

Mike Murphy took the forms from his latest acquisition.
Mike was a headhunter for MTC Corp., one of the
foremost software publishers in America, and there was
sure to be a bonus for him for signing up Ray Hirsch.
The k*d wasn’t much to look at; about 5’6″ and real
skinny, with rather long and unkempt brown hair,
glasses, dressed in running shoes, a tee-shirt, and
jeans, but he had the potential to be one of the best
software engineers going. Ray was 24, but he didn’t
look old enough to buy a beer.

Mike didn’t feel bad at all about taking advantage of
Ray’s situation to lure him out west. Ray was from
Massachusetts and if nothing had happened he would
probably never have left there. Educated at MIT, he
lived at home with his parents while working for a
little known firm outside Boston. Little known that is
until a data base system Ray had developed for them
became a best-seller and the industry standard. Ray had
felt no need to change employment and stayed with his
old firm, but at a much higher rate of pay.

What had changed everything was the death of his
parents in a car accident. When he had heard of it,
Mike immediately started courting Ray, thinking
correctly that he might like to get away from New
England and all the memories that it held for him. Ray
was financially well off; what with the insurance
settlement, selling his parents house, and his savings
from his salary and bonuses, so Mike had avoided
talking financial incentives and instead emphasized the
reputation of the staff and facilities at MTC. The
result was sitting in front of him.

“Welcome to MTC Ray, I’m sure you’ll be happy here. Why
don’t you get settled and report in next Monday.”

“Thanks Mike, but I’m staying in a motel and don’t know
anyone here. If it’s possible I’d like to see where
I’ll be working and get acquainted with my new co-
workers.”

“Sure thing,” said Mike while thinking, “what a find;
brilliant and a workaholic to boot.”

Ray was finding his way around the work station they’d
given him when someone walked into his cubicle.

“Hi, you must be the fresh meat. I’m Jack Doyle,
welcome.”

Ray shook hands and checked out his greeter. Jack was
slightly taller, by about 2 inches, but except for that
and his blonde hair they could have been related. They
were, but only by membership in that fraternity of what
is sometimes called ‘computer geeks’. Perhaps that was
why they felt an immediate affinity for each other, or
maybe there was something else.

Ray and Jack talked, discovering how much they had in
common. When Jack found out that Ray was staying in a
motel, he insisted that Ray move in with him until he
could find a place of his own. Ray didn’t need much
persuading and soon they were unloading his stuff into
Jack’s secluded three bedroom house. Ray was surprised
at how neat the house was, for a bachelor.

“I forgot to ask. Do you live here by yourself?”

“Right now I do. My sister Janice lived here with me
for awhile after our parents died. She just moved to LA
for a job, but I let her keep some of her stuff here in
her old room.”

That explained to Ray the neatness. A woman’s touch
always shows through. One of his favorite pastimes was
to get dressed up and keep house. Ray loved to clean,
cook, and do laundry as Rachel. His mother had found
his dressing up cute and encouraged him at it, teaching
him the housekeeping skills most men never learn, all
the while hiding Rachel from his father. Ray missed his
mom and he missed Rachel. He couldn’t wait to get his
own place.

Jack showed Ray the room and bath he’d be using and Ray
quickly settled in. That evening, Jack invited Ray to
go out with him to make the rounds of the bars and meet
some people. Ray declined, saying he was too tired from
his flight and first day at MTC, but would gladly take
him up on the invitation some other night.

Alone in the house, Ray inspected his new surroundings.
In the den he turned on the TV, then turned it off when
he found nothing interesting. On the coffee table was
the latest ‘Cosmopolitan’. Ray picked it up and looked
at it; the mailing label said Janice Doyle.

“She mustn’t have changed her address yet,” thought
Ray.

He thumbed through the magazine. Then he remembered
Jack saying that she’d left some stuff in the other
bedroom. Ray knew that he shouldn’t, that he would be
betraying a confidence, but what the hell, it wouldn’t
hurt anyone. So he decided to sneak a peek in her room.

Ray opened the door to Janice’s room and turned on the
light. It was a vision of feminine delight. Decorated
in pastels with lace everywhere, it looked as if she’d
just left that morning. Ray walked past the bed,
covered with a satin quilt, looked at the dressing
table, and opened the closet. There were only a few
dresses hanging in it, but they were all very stylish
and feminine and Ray felt envy and desire rise within
himself. There were several pairs of shoes on the
closet floor; all of them high heels.

“It looks as though she took her work and casual
clothes with her and left the dressy stuff here,”
thought Ray.

He took down a dress of black crepe and held it up
against himself. It was a size 11 and looked as though
it would fit him perfectly. He overcame that thought
and quickly re-hung it in the closet. He opened the
other door. It led to a bathroom, looking in Ray saw
that it connected to Jack’s room, thinking it odd that
brother and sister would share a bath. On his way out
he stopped to open a drawer in the dresser. It was
filled with neatly folded lingerie in all the colors of
the spectrum, made of satin, lace, and nylon. He
fingered a pair of satin panties.

“I wonder if she’d miss one pair?” he mused.

He quickly gave up on the idea, shut the drawer, turned
out the light, and left; determined to get his own
place and start dressing up again as soon as possible.

The next day Jack dropped off Ray at a car rental
agency on his way to work. Jack had convinced him that,
being in California now he needed a car and should rent
one, until he decided on which model to buy, instead of
relying on public transportation. Ray took off in the
rental car and went house hunting.

Ray arrived home in the early afternoon. He’d found a
couple of places that looked promising, but he wanted
Jack’s advice on the neighborhoods and traffic, as well
as if he would be better off buying or renting. Driving
up, Ray noticed that the flag was up on the mailbox.
Jack wouldn’t be home for hours and Ray thought he’d do
him a favor and bring the mail in. Something in the
pile of letters caught his eye; an envelope in an odd
shade of green. He’d seen that odd colored envelope
before. Ray pulled it out of the pile and was shocked
to see the return address: Empathy Press, Seattle.
Being a long-time fan of TV fiction, he was only too
familiar with what they sold. The envelope was
addressed to John Doyle.

“Holy cow!” he thought. “Is Jack a crossdresser?”

Then a lot of what had seemed to be merely coincidence
fell into place. Ray dropped the pile of letters on the
hall table and went up to Janice’s room. He went
through the dresser and in the bottom drawer found what
he had thought might be there; falsies. Not your
everyday falsies though, rather they were custom made
breast prothesis.

Looking through the lingerie drawer, Ray found what he
recognized as a cache-sex; he used one himself to
compress and hide his genitals when dressed. He also
saw some really stiff boned corsets that you couldn’t
expect to find in a young ladies wardrobe in this day
and age. These things didn’t convince Ray beyond a
shadow of a doubt. What did were the hat boxes in the
closet. There were lots of them, but they didn’t hold
any hats. Rather they held an array of dressed wigs on
stands in various shades of blonde.

“Well I’ll be damned, Jack is a TV. No wonder we hit it
off so well. There is no sister, Janice is to him what
Rachel is to me.” Ray said to himself.

Ray wanted to let Jack know that he was also a TV, but
couldn’t think of a discreet way to do it. Finally he
decided that the only way to do it was to be up front
and forthright about it.

That evening Jack stayed home and was reading in the
den, when Ray decided to broach the subject.

“Have you got a minute Jack?”

“Yeah sure. What’s on your mind?”

“Well, I wanted to ask your advice on houses, but
something else has turned up that I wanted to talk to
you about.”

“What’s that?”

“I hope you won’t be upset with me. I have never shared
this with anyone but my mother, but I think you can
understand. I am a crossdresser.”

Jack didn’t say a word, but by the way he blushed Ray
could tell that he’d hit a nerve.

“What do you mean, you think I’d understand?”

“I saw the letter you received from Empathy Press. I’ve
read their books for years and thought you might be a
crossdresser also.”

Jack sputtered, “… er… I don’t…”

“Don’t worry Jack. Let’s drop it and I’ll forget all
about it.”

Jack got his voice back. “No, let’s talk Ray. Yes I’m a
TV, but I’ve never shared it with anyone and you kind
of caught me by surprise.”

The boys continued talking long into the night. Ray
discovered that his suspicions were correct; there was
no sister Janice, just Jack. After a long talk, they
decided they could trust one another and at Jack’s
invitation, Ray decided to move in and share the house
with him.

CHAPTER 3

Ray moved in and bought a car. Eventually his
belongings arrived and he settled in. Things were going
great at work, the only problem was that each seemed
reluctant to appear before the other ‘en femme’. One
evening they were talking when the discussion turned to
dressing up. Ray learned that Jack had never gone out
dressed.

“You’re kidding me, surely you can pass.”

“I’m not so sure, and even if I could, where would I
go?”

“Out for a drive, a walk, shopping, or to a bar.”

“Look I’m not gay so I wouldn’t go to a gay bar and I
wouldn’t know how to handle it if some guy tried to
pick me up in a straight bar.”

“I’m not gay either, but going out dressed as a woman
and passing in public can be the biggest thrill of all.
You simply must try it.”

“I don’t know Ray, what if someone recognized me?”

“Come on. Don’t give me any lame excuses. I’ll show you
how easy it is. You take me out as Rachel, see how easy
it is, then I’ll take you out as Janice. That is if
you’re not too much of a wimp.”

“I’m no wimp, you’re on.”

Ray took off from work at noon that Friday to prepare
for his ‘date’ with Jack. Soaking in a tub full of
bubble bath, Ray shaved his body clean of the hair
which had regrown since his last appearance as Rachel.
He dried off, rubbed himself down with lotion, put on a
robe, and went to his room. There he applied long false
fingernails and painted them bright red. Then it was
time to dress.

Ray carefully pushed his balls and cock up inside
himself and put on a tight cache-sex to hold them
there. He had to do this first because if he didn’t and
then got turned on, as he always did when dressing,
he’d never get them hidden away. Ray got out what he
called his ‘boobies’. These were a pair of silicon and
latex falsies that looked, felt, and bounced like the
real thing. He smeared surgical adhesive on them, laid
down on the bed, and positioned them properly. In
several minutes they were set and would remain there
until he applied the solvent. By dint of much effort,
Ray was able to get a tight waist-cinch on and buckled.
He could hardly breath. Padded panties followed to give
him the hips and ass he lacked. Looking in the mirror,
Ray saw that his skinny male body now sported a
voluptuously feminine outline.

Ray put on a bra and panty set of white satin and lace.
Sheer, smoke colored panty-hose sheathed his hairless
legs. A slip which matched the rest of his lingerie
flowed over every contour of his new curves. Deciding
to not be too extreme, Ray stepped into a clingy red
knit dress, pulled it on, and zipped it up. He buckled
on a wide black patent leather belt, which served to
emphasize his nipped in waist, and stepped into some
black patent high-heeled pumps. A ladies watch went on
his wrist and gold hoop earrings went into his pierced
ears.

“Holy smoke!” said Ray to himself. He’d gotten into the
dressing so much that he hadn’t thought about make-up.
He put a towel over his shoulders to cover his dress
and quickly spread on the foundation, applied mascara,
eye-liner, and eye-shadow. Powder and blush were put on
and he was outlining his lips in a bright red which
matched his nails when he heard Jack come in.

“Rachel?”

They had agreed that they would always use a girls name
whenever one of them was dressed.

“I’m still getting ready Jack. I’ll be out in a
minute.”

Ray quickly colored in his lips and sprayed on some
expensive perfume. He got out a black leather purse and
into it he put lipstick, a powder compact, and an
atomizer filled with perfume. Taking a ladies billfold
from the purse, he transferred to it, from his wallet,
all his credit cards and identification.

“What else?” he thought.

He answered himself by putting on a thick gold link
necklace and getting out a ring. It wasn’t just any
ring; it had been a gift from his mother and he
treasured it. It was a class ring from MIT but in a
girls style, set with his birthstone, and engraved “to
Rachel, love Mom.” He slipped it on his right ring
finger and was dressed.

One more thing remained. Ray shook out a long brunette
wig, pulled it over his head, tucked his own hair up
under the cap, secured it with bobby pins, and brushed
it out so that curls tumbled over his shoulders and
down his back. Ray tossed the brush into his purse and
grabbed what for him was an indispensable item; glasses
in a fashionable women’s style. He’d be blind without
them or contacts. He went out to meet Jack.

Jack was dumbfounded. He stared at the girl who walked
into the den. It wasn’t that she was beautiful,
although she was, but rather that she revealed
absolutely no hint as to her true identity. From the
long curly hair down to the tips of his high heels, Ray
appeared totally feminine and entirely at ease.

“Ray, is that really you?”

“Yes Jack, but please, call me Rachel.”

“Sure thing Rachel. Wow, you even talk like girl. How
were you able to learn how to do that?”

“It’s not hard, it just takes lots of practice.”

They talked for a while and then left, looking for all
the world like a young couple out on a date. In the
driveway, Ray waited for Jack to get the car door for
him.

“Sorry Rachel, I forgot my manners there for a minute.”
Jack said as he rushed around to open the door.

“Don’t worry about it, but you should be careful to
always think of me, and treat me, as Rachel and not
your roommate Ray. I also should let you know that,
before you go out, you’d better practice getting in and
out of a car in a dress. It’s not as easy as it looks.”

And so Jack and Ray departed for their first evening
out. It wasn’t very memorable. Ray got asked for proof
of age, which naturally he didn’t dare provide, at
several nightclubs before they found one that they
could get into. They sipped their drinks, talked, and
at Ray’s instigation, and with great reluctance on
Jack’s part, they danced to some disco numbers. They
didn’t stay out late, but returned home rather early.

“See how easy that was?” Asked Ray after he had
returned to a masculine visage.

“Sure, but you’ve had lots of practice.”

“Not that much, and remember; I had to start somewhere.
So when do I get to take Janice out?”

“I don’t know. We’ll see.”

A couple of weeks went by with Jack showing no
inclination to uphold his end of the deal. Finally, Ray
pressed the issue.

“Jack, it’s Friday and we are going out tonight. By we
I mean Janice and me. That is if not you’re a total
wimp.”

“OK, OK I’ll do it.”

Ray arrived home about six, wondering what he would
find there. Jack was still in his room getting ready so
Ray went in and put on a jacket and tie. He had decided
to go all out and make sure that Jack enjoyed his first
public appearance as Janice.

Ray was sitting in the den when he heard steps on the
stairs. He looked up to see Jack enter and could tell
immediately that Jack was scared and very tense.

“Why Janice, how nice you look tonight,” said Ray.

“Do you really think so?”

“Oh yes.” And he meant it.

Jack had on the black crepe cocktail dress that Ray had
seen in the closet on his first night in the house and
it fell to just above his knees. He wore a long curly
blonde wig and while his make up was perhaps a trifle
heavy, and he didn’t use as much padding as Ray, the
overall effect was quite pleasing. Ray decided that
Jack’s best feature was his legs. They were long and
quite shapely, giving Jack a coltish look. Jack
clutched a small black bag nervously in fingers tipped
with long red nails. Ray looked him over and noticed
that something was missing.

“Do you have any jewelry to put on Janice?”

“No. I never thought about that.”

“Well every girl wears some, no matter how small. Let’s
see if I have some you can borrow.”

Jack followed Ray to his room with jittery steps,
unaccustomed as he was to the high heels he had on. He
was intensely aware of his legs; shaven and on display
in sheer black hosiery.

“I don’t have all that much myself, but these should go
well with your black dress.”

Ray handed Jack a silver necklace and bracelet which he
put on.

“Here put these earrings on.”

Ray handed Jack some silver hoops.

“Ray my ears aren’t pierced.”

“What? Every girl has pierced ears these days. We’ll
just have to get that taken care of, but for now here’s
a pair with clips. While we’re at it let’s get some
scent on you. I see you’ve got a lot to learn about
going out as a girl.”

“That’s what I tried to tell you.”

Ray held the door open for Jack as he entered the car.
He didn’t show too much thigh and it was obvious he’d
been practicing.

“Where are we going Ray?”

“Just relax Janice.”

“I’d like to but I’m terrified.”

“I understand how you feel, but take my word for it,
you look great. Just sit back and enjoy the ride.”

The boys arrived at their destination; a rather
exclusive restaurant.

“I can’t go in there.” Whined Jack.

“Don’t worry. Just let me do all the talking.”

Ray noticed heads turn as they entered. Jack was
several inches taller than Ray in his heels, and no
doubt some of the onlookers were wondering what such a
babe was doing with a nerd. Which was precisely why Ray
had avoided the club scene.

Ray noticed that Jack neglected to smooth his skirt
under him as a girl would when he sat down.

“He does need some work on the fine points,” Ray
thought.

Ray ordered wine which they sipped, helping Jack to
relax a little. Ray then ordered dinner for the both of
them, after which Jack felt somewhat more composed.
That is, until Ray asked him to dance to the music of a
small combo which had started playing.

“I don’t know how to dance.”

“That’s good, it will be easier for you to follow my
lead instead of trying to lead yourself.”

“I don’t want to dance.”

“I think you’re afraid.”

After some discussion, Ray found himself with Jack in
his arms, guiding him around the dance floor. When it
was over Ray thanked him for the dance.

“Can we get out of here now?”

“Sure.”

During the ride home Jack was elated, barely believing
that he had been able to pass successfully in public.

It was a while before Janice was out in public again.
In the meantime, under Ray’s tutelage, Jack practiced
speaking like a woman and perfecting the persona of
Janice. He made noticeable progress and to celebrate,
Ray took Jack to get his ears pierced and bought him a
pair of gold hoops as a present. As Jack grew more
experienced in passing and gained confidence in
himself, the only disagreement the boys had was about
who got to dress up; they each wanted to don their
finery and go out as girl. They eventually agreed to
take turns escorting the other on alternate Fridays.

It also wasn’t long before Rachel met Janice; Ray
dressed up one Saturday to do housework and Jack
decided to join him. Thus began what would become a
kind of routine; one of them would dress up Friday and
be escorted out on the town by the other. The next day
the escort would join the other as a girl and there
they would stay for the weekend.

Something else was happening to the boys relationship
with each other. They were comfortable with, and
trusted each other more than they ever had anyone
before, except for Ray and his mother. The complexity
arose because not only did Ray and Jack feel that way
about each other, but Janice and Ray did, Rachel and
Jack did, and Rachel and Janice did. You don’t have to
be a brilliant to see the potential complications in
this relationship.

CHAPTER 4

Just as Jack and Ray were progressing in crossdressing
they were also taking great strides at work. They
became a team, much like they were at home, and the
results for MTC were nothing short of amazing. New
software applications, developed mostly by Jack and
Ray, practically flew off of dealers shelves. The boys
were showered with money and treated like royalty. They
sensed that they could get away with anything and,
naturally, they started getting outrageous. It started
with Jack wearing his diamond studs to work and daring
Ray to top that. Ray did and their competition
escalated from there.

One day before work Jack came down to breakfast.

“Guess what Ray?”

“What?”

“I’m going to work dressed completely in girls clothing
today.”

“Oh yeah. Just what are you going to wear?”

“What I have on.”

“What?”

Ray looked closely at Jack. Sure enough the shirt
buttoned up the wrong side and an examination revealed
that the trousers were misses, even though cut in a
masculine style.

“These are women’s loafers and it looks like I’m not
wearing any socks, but actually I have on sheer nude
panty-hose,” boasted Jack, “and underneath it all I
have on the most delicious teddy.”

“So?”

“So how you gonna top this Ray?”

It took Ray awhile to figure out how to pull it off.
One Friday he asked Jack to meet him in the employee
cafeteria for lunch as he had something important he
wanted to discuss with him. Jack complained about the
quality of the food, but nevertheless agreed to be
there. Imagine his surprise when in walked Rachel,
looking very much the businesswoman in a smartly
tailored suit.

Ray walked over, with his red lips in a big smile, and
greeted Jack. Jack was flabbergasted.

“Just what do you think you’re doing?” He hissed under
his breath.

“Eating lunch. What else would I be doing here?”

“But… what if someone sees you?”

“Plenty of people have already seen me. Relax no one
will ever know. I’ve got this visitors pass.” He
pointed a long red fingernail to the badge clipped to
his blouse. “I liberated it a couple of weeks ago.
After lunch I’ll walk out of here, turn in it. I’ll bet
you that the guards are looking at me and not the
badge. By the time they figure out something is fishy,
if they ever do, this girl will be long gone.”

“Wow.”

“Yes indeed. You had better start thinking hard about
how you’re gonna top this.”

“Is that why you wanted me to meet you here, to tell me
this?”

“Partially. You know, we are a pretty good team; as
software engineers I mean. How would you feel about
going into business for ourselves?”

“What do you mean?”

“I mean we could work for ourselves, at home if we
like. We write our applications and hire someone to
market them for us.”

“Can we do that?”

“Sure we can. In fact, I have been approached by a firm
that would like to do just that, it would also give me
the opportunity to do something I’ve been thinking
about for awhile.”

“What’s that?”

“I’ll tell you later.”

“Say Rachel, you’d better go home and change, or have
you forgotten that it’s Janice’s turn out tonight.”

“No I haven’t forgotten, but I have decided that
tonight is going to be girl’s night out; Rachel is
going to take Janice out.”

“What? But what if you get pulled over or something?”

“So what? Just be ready by seven.”

At seven-thirty that evening Ray’s car was headed north
on 101. The boys both wore stylish cocktail dresses.

“So where are we headed Rachel?” asked Jack.

“I thought we’d go bar hopping in San Francisco and try
and pick up some guys.”

“WHAT! Are you crazy?”

“Relax. I was only kidding. Actually we are going to
San Francisco, but for a meeting of crossdressers.”

“What?”

“Don’t worry, it’s a group called ETVC and I’ve been to
their meetings a couple of times already. It’ll be fun
and you’ll meet lots of interesting people.”

Jack rode on in silence until he remembered what Ray
had told him at lunch. “By the way Rachel. What is this
big secret you were going to tell me about?”

“Well. I was thinking. Isn’t dressing up the greatest
thrill, and don’t you treasure every minute you get to
spend as Janice?”

“Yeah. I guess so.”

“Well the longest I’ve ever gotten to spend as Rachel
was a long weekend. If I can work at home I may do it
as Rachel, at least some of the time. Do you think
you’d like to join me?”

“Gee… I uh don’t know for sure.”

“Well, think about it.”

“I will.”

The boys went on to their meeting and it was a great
success. They enjoyed themselves and were pleased to
meet with many of the other crossdressers, including
many professional people. They were especially taken
with a beautiful blonde, who called herself Sally and
told them that he was an M.D. in the real world. Jack
and Ray each left with their handbags full of business
cards.

CHAPTER 5

Jack and Ray left MTC and formed their own company, but
things didn’t turn out exactly as Ray had planned. The
boys spent so much of their time on projects that
Rachel and Janice were consigned to the closet. The
dedication paid off in the long run. Ray produced a
word processing program that was revolutionary; he
named it ‘Flawless’ because that’s the kind of document
it turned out. You didn’t have to know what you were
doing, it practically wrote everything for you. Jack
meanwhile had developed a spreadsheet that any idiot
could use. These products were the subject of a visit
by the lawyers for their marketers.

“Here is the deal gentlemen. My principals have
instructed me to offer you the sum of 2.5 million
dollars for all rights to the aforementioned programs.”

Jack and Ray looked at each other astonished.

“If this sum seems excessive it is because the contract
contains an agreement not to complete. The persons
tendering this offer believe that they can corner the
market with your programs. The only thing they are
afraid of is that a year or two down the line you guys
come out with something better. Accordingly you agree
not to participate in any software development for a
period of six years after the signing of the contract.
What do you think?”

Ray looked at Jack, who grinned, then turned to the
lawyer.

“Where do we sign?”

When the lawyers had departed Jack asked Ray, “So what
do we do now?”

“We celebrate.”

“That’s cool, lets go.”

“Not so fast dude. We really have neglected Janice and
Rachel shamefully. I’ve been so busy that I haven’t
shaved my legs in months. Why don’t we let the girls go
out and celebrate.”

“Yeah, great idea. Let’s go get dressed.”

“Hey not so fast, it’s only lunchtime. Let’s do this
right. Remember, we’re rich now.”

“So what do we do?”

“First thing, we hire a limo for the evening.”

“Wow!”

“Then we go shopping for some evening gowns.”

“Yeah, right on.”

“Then we get dressed.”

Many men looked with longing at the two young women who
passed through the best restaurant and the top bars in
San Francisco that evening obviously celebrating. They
were sexy, dressed to the nines, and obviously loaded,
with money as well as booze.

Early the next morning they were riding back to San
Jose in the limo with the drivers screen up. At Jack’s
suggestion they were drinking champagne out of their
high heels. They’d already had a lot to drink.

“Here’s to ush,” said Ray lifting a sequined pump to
his lips. He swallowed, but more of the bubbly ran out
the sides of his mouth than down his throat.”

“Shit, my new dresh . I paid four thousand dollars
for thish dresh. Ish by a famoush designer. I don’t
remember who zackly but he’s famoush.”

“I love thish,” said Jack, “I love being Janish and I
love you Rachel. Les be them for awhile.”

“ I loves you too Janish.” Ray said as he leaned
over and kissed Jack on the lips. “Les do keep the
girls around.”

Neither of them thought the kiss out of line. In fact,
they didn’t even remember it.

Ray woke up the next morning with the worst hangover of
his life. He and Jack had drunk some more after they
got home and it looked as though he had barely made it
to bed. Looking at his pillows he knew he hadn’t
removed his makeup before he crashed. His wig had been
thrown on the bureau, and his expensive new dress was
in a pile on the floor along with his hose; he’d slept
in his lingerie. He wondered where the new shoes he’d
bought were, until he remembered drinking champagne out
of them the night before.

Ray got up and took off his bra, panties, padded
panties, and gaff. The adhesive holding his boobies on
was good for days so he left them on while he showered.
Afterwards he decided to remain as he was and put on
panties, a negligee, and a robe and went down to get
something to eat. He was munching on toast and drinking
coffee when Jack came down. Jack had removed all traces
of Janice and was wearing an old bathrobe.

“Wow dude! That was some night.” Jack said.

“You’re not kidding. I don’t think I can handle one of
those more than once a year.”

“So who are you this morning; Rachel or Ray? You look
like half and half.”

“I’m not sure yet. Let me get over this hangover and
I’ll let you know.”

Jack and Ray started rearranging their affairs, in this
they were guided by some of the people they met in the
TV club they belonged to. A lawyer and a banker helped
them set up their investments, then arranged it so that
Jack and Ray could access their money as Janice and
Rachel and even got them credit cards in those names.
Jack and Ray also started seeing Sally, or Walter as he
was known as a man, for their medical needs.

One night Ray was driving himself and Jack home from
their TV clubs annual dinner.

“Don’t let that award go to your head Janice. You’ve
still got a ways to go before you can compete on my
level.”

Jack had won an award as most improved TV while Ray had
taken first place in the evening gown event.

“You’re just lucky I didn’t enter the evening gown
competition.”

“Oh yeah. Don’t get too uppity. Remember, I taught you
everything you know.”

“That may have been the case, but these days I can pass
as well if not better than you.”

“In your wet dreams you can!”

“I can see we’re gonna have to settle this.”

“Definitely. Got any suggestions.”

“No, but I’m thinking on it.”

The next day Jack presented his challenge.

“You once said that you wanted to live as Rachel for
awhile. So here’s the wager. We each live as a girl for
one year. Whoever give up before then looses. If we
both make it then we let the members of the club decide
which one of us is more convincing as a woman, and the
majority decision will be binding.”

“Sounds good to me, but what will we bet?”

“That’s the fun part. We’re living off the interest on
our money now and I guess that works out to a little
over $100,000 a year right?”

“I guess.”

“O.K. The loser has to turn over his income for one
year to the winner.”

“That’s a pretty big hunk of change.”

“And that’s not all. The loser has to work for the
winner as a servant for the following year.”

“What do you mean.”

“I mean personal maid.”

“I think you’ve been reading too many of those TV
Queens Fiction Digests.”

“Maybe, but you have to admit, it’s an interesting
challenge.”

“Yes it is. I can see you now in a maid’s uniform,
tottering about on six inch heels, serving my guests
while I act as hostess for the club.”

“You seem pretty sure of yourself.”

“You’re damn right I am. Let’s formalize this bet in
front of witnesses and make it official.”

In due time the formalities were taken care of and Jack
and Ray embarked on their year in dresses, well two
years for one of them.

One morning Jack came down to breakfast in a robe and
Ray could see that something was different. Then he
realized that Jack didn’t have his falsies on.

“What’s the matter Jack? You giving up so soon?”

“I thought you’d say something like that,” replied
Jack, “and I want you to know that nothing could be
further from the truth.”

Jack opened his robe.

“Take a look. I’ve been taking hormones and thought I’d
surprise you when I win our bet by having real breasts,
but they were getting too big with the falsies over
them.”

Ray stared at Jack’s chest. Sure enough, there was some
development there; the nipples were bigger and the
aureoles had expanded and were swelling out. Ray asked
him, “Where did you get hormones from?”

“Well Sally told me she was taking them and recommended
it, so I got her to set me up.”

Later on, Ray thought about Jack and the hormones. He
stood to lose a significant amount of money, not to
mention being Jack’s maid for a year. He called up
Sally and made an appointment to see her as Walter, on
business.

Jack sat on the edge of an examining table as Walter
explained his options to him.

“Sure you could go on hormones, but let me tell you it
takes a long time before you see any changes and by the
time you do, Jack will be way out in front, if you’ll
excuse the pun. No, for you we need something better,
something dramatic… I know, I have just the thing for
you, implants.”

“I don’t want my chest pumped up with silicon.” Said
Ray.

“Silicon? That was the dark ages. Let me show you what
we can do. We implant a little pouch under each breast.
This is done under the arm and it is empty at that time
so it leaves no scar. It settles in and then it has we
fill the individual cells in it with saline solution.
It’s comfortable, the size increases as fast or as slow
as you want, and you get as big as you want. We control
which cells fill and create a perfectly normal
appearing breast.

“If you also take hormones, as I recommend, to make
your skin soft, we can remove some of the saline
solution to keep the breast size constant so you don’t
become a ‘tit queen’. When you’ve had enough of living
as a woman it’s a simple matter to empty the sacks out
and remove them.”

“Wow. I can do all that and it’s not permanent.”

“That’s right.”

“O.K. let’s do it.”

“Well let’s talk about something else first Rachel. I
think you’re very sweet, so I want to help you win your
little contest. I believe you should also have some
cosmetic liposuction done.”

“Some what.”

“Liposuction. That’s what they call it when they remove
fat from under the skin. It was developed as a way for
grossly obese persons to lose some weight quickly, but
now is used to give a person whatever shape they want.”

“Yeah, but then I’m stuck like that right?”

“Wrong. You diet, exercise, and take hormones to keep
the shape, but when you’ve had enough, stop the
hormones, eat a lot and work out and your body will
return to a male form.”

“Just how good is this process?”

“Well from some of the cases I’ve seen firsthand; they
could make Bo Jackson look like Whitney Houston.”

“Really?”

“Yeah!”

“Where do I sign up?”

“Let’s see. How about in two weeks?”

“Great. I’m there.”

“Why don’t you let me start you on hormones today?”

“Sure, why not?”

Ray, on his stomach on the examining table, felt the
needle enter his left buttock. He was on his way.
“Let’s see Jack top this”, he thought.

Ray returned home with his newfound curves. A little
sore, but none the worse for wear and tear. He didn’t
see any change in his breasts, but what a waistline!

After the implants had settled in and stopped itching
he returned to Walter who started the slow process of
filling them up. It wasn’t long before Ray discarded
his falsies too. Naturally when Jack saw the changes
Ray had wrought to his body he couldn’t give up and not
respond in kind. It was like an arms race, or if you
prefer, a boobs race. Jack went to see Sally and it
wasn’t long before he was looking like a centerfold
also.

Ray noticed that Jack seemed to stand and carry himself
differently. He wondered what was going on, until one
night when both of them were in the den, wearing baby
doll nightgowns, and watching television. Ray noticed
that Jack had something on under his.

“What’s that you have on Janice?”

“Just my corset.”

“A corset! Why are you wearing a corset now?”

“I always wear a corset Rachel. Even when I’m
sleeping.”

“Really.”

“Yes. It’s for figure training.”

“I just don’t understand it Sally”, said Ray. “Janice
is really getting quite a figure. Can wearing a corset
all the time do that?”

“I’m sure it helps, but I know that’s not the only
thing. Janice asked me not to tell you, but I feel I
must. You know those sacks in your breasts? Well Janice
had me implant a slightly different variant in her hips
and buttocks.”

“I guess I had better try them too.”

“It wouldn’t hurt.”

Ray wondered to himself if maybe all of this was
getting out of hand. He was slowly getting used to the
corset he wore all the time now, but it was still a
major pain in the ass. Still he had to admit it did
make a difference. He walked straighter and held his
chest out. And what a chest it was!

The tiny nipped in waist only served to highlight the
enlargement of his breasts, hips, and ass. Even with
his increased dimensions Ray noticed that a lot of his
clothes seemed too large. Like Jack he was eating less
due to the constant restriction of the corsets. He was
glad he hadn’t invested too much in dresses. He might
go down a size before this was over.

CHAPTER 6

Time passed and as is often the case, too much money
and no work time led to extreme boredom. One afternoon
the boys sat by the pool in bikinis. Although they
could have passed on the beach at this point in their
development, they preferred working on their tans in
the privacy of their own yard. Jack picked up the paper
he had put down earlier and idly read through the
classified ads.

“Lately I feel like I’m going crazy. You know, what I
need is something to occupy my time; like a job.” He
said to Ray.

“Ha! What are you gonna do? Get a job as Janice?”

“I bet you I could. I could even write my own
reference.”

“No way dude! And if you could, I bet you wouldn’t be
working very long before they find out you are a guy
and fire you.”

“I betcha I could last longer working as a girl than
you could.”

“Oh yeah?”

“Yeah!”

“You’re on.”

“Fine. How much?”

“Say ten-thousand?”

“Sure that won’t break you?”

“Fuck you. Let’s shake on it.”

“How about a grand to the first one with a job?”

“Fine with me.”

They shook on it and each grabbed part of the
classifieds and started reading.

“Look,” said Ray, “here’s an ad for a receptionist for
a law firm. It says familiarity with Flawless desired.
I wonder what they would say if they knew that I wrote
the program?”

Jack found one that had potential. It said: RETAIL –
clothing & costuming. Self-starting & reliable.
Experience not necessary. Fashion Warehouse 555-1212.

“You know Janice, I don’t know the first thing about
job interviewing as a girl.”

“Either do I, but I do know that we can’t go looking
for job looking like this.

While each of the boys now had a nice feminine cast to
their bodies, their hair had grown in long and thick
and was too bulky to wear a wig with. It just hung
there, lifeless in clumps and tangles.

“What we need is a trip to a beauty salon.”

“No way Janice. We’d be found out for sure, and we
don’t know the first thing about going in one.”

“What do you mean we. I think I know how to handle
this. I remember a girlfriend in college who was in the
same boat. Just wear girls jeans and a sweatshirt and
we’ll head up to Berkeley.”

CHAPTER 7

“Hello girls. May I help you?” Asked the beauty store
operator.

Jack and Ray stood there looking at each other and
trying very hard not to giggle. Ray elbowed Jack
whispering, “You got us into this. Say something.”

Jack spoke up. “It’s like this… you see we…”

“Let me guess. You’re graduating and haven’t worried
about your appearance since you entered college, but
now you’re going job hunting and need to look your
best. Am I right?”

Jack breathed a sigh of relief. “Er… exactly. How did
you know?”

“It’s not very hard. Every year we get a new crop of
you gals. We’re old hands at this. Come on who’s gonna
be first?”

The boys looked at each other again. Not waiting for an
answer the lady grabbed Jack by the arm. “Sweetie,
you’ve got to get used to this sometime and now’s as
good as any.”

She handed Ray a book of hairstyles. “You can wait here
until Betsy is ready for you. Meanwhile, look through
this and see if anything strikes your fancy.”

Jack and his guide vanished behind a screen into this
unfamiliar domain of women.

The boys put themselves into experienced hands and took
the whole treatment; wash, cut, perm, facial, manicure,
make-over. The beauticians worked their magic and
educated them in the use of cosmetics at the same time.

Ray stared at his roommate, in awe of the delicately
beautiful girl that Jack had become. They left the
salon, each toting the bagful of cosmetics and hair
care products he had purchased. On the way to the car,
Ray wanted to express his feelings, but his
inexperience and shyness around girls showed as he
groped for words. All he could get out was: “You’re
very pretty.”

To which Jack replied. “Thank you Rachel. You don’t
look so bad yourself.”

It was on to the mall after that, where the boys spent
the afternoon purchasing wardrobes appropriate for
young working women.

They were both hired the next day, so by agreement the
$10,000 went into the big pot.

Each of the boys discovered his changed reality for
himself; it was one thing to have breasts that could be
unglued Sunday evening before work on Monday, but it
was quite another to realize that come Monday morning
you’d better have a clean bra ready to go.

They met for lunch their first day on the job.

“So how’s the fashion business Janice?”

“It’s great except I’m on my feet all the time and they
insist that I wear high heels as well as fashions from
the store, but I get a super discount. How do you like
my this?”

Jack stood up and twirled, showing off the black
leather miniskirt he’d been outfitted in. It seemed to
be painted on his pert little butt.

“I’d never get away with that at the law firm. They’re
so stodgy there. It was made clear to me that I had
better appear conservative and feminine at all times.
In dresses only, I might add. Suits are only allowed
for women lawyers. Anyway I noticed a couple of the
younger lawyers giving me the eye. The only difficulty
is typing with these long nails. It’s one thing I never
had to cope with before now.”

CHAPTER 8

Jack and Ray both excelled in their new occupations.
Not only were they accepted as girls by all who met
them, but they were also highly valued by their
respective employers. Ray had taught himself shorthand
and stenography and had been promoted to executive
secretary at the law firm, while Jack had risen to the
position of buyer at the clothing store and was doing a
little modeling on the side for them. The boys had been
successfully living and working as women for over six
months, when Jack received an invitation for the two of
them to go to a costume ball on Halloween.

“What shall we go as?” He asked Ray.

“I don’t know. What do you think?”

“I don’t have any ideas.”

They sat in silence for awhile when Ray said, “I know
let’s go as ourselves.”

“No silly. We are supposed to go in costume and
everyone knows Janice and Rachel.”

“That’s not what I meant. Let’s call off the bet for
one night and go as Jack and Ray.”

“Not a bad idea. Do you still have some men’s
clothing?”

“Yes. Don’t you?”

“No. I gave it all to Goodwill.”

Ray hadn’t known that Jack had taken so drastic a step.
“I’ve got mine in a box in the basement. I’ll go get
it.

Ray stared at his reflection while Jack looked on. The
pair of men’s shorts he had on definitely weren’t made
to fit his body the way it was now shaped. The cotton
briefs were stretched tight across his plump derriere
while the elastic band hung loosely around his tiny
waist.

“What can I do with these boobs?” he asked Jack. The
size of his ample breasts was not at all reduced by the
tight tee shirt and fat nipples were obvious as they
pushed against the thin cotton.

“I know,” said Jack, running from the room. He returned
with an elastic bandage which the two of them wrapped
tightly around Ray’s chest.

“This isn’t going to work” said Ray.

That much was obvious. Even with the bandage crushing
his breasts he couldn’t button up his shirt over the
remaining bulge. And his pants… Well they were
stretched so tight that if he bent over they’d surely
tear.

“I look like a girl dressed as a boy.”

Giving up on the idea they rented costumes and went as
two southern belles. Ray also gave away his remaining
male clothes, abandoning the notion of getting into
them again any time soon.

It was the night of the ball that Jack and Rays
relationship took a dramatic turn. They had been much
sought after as dance partners by all the single men in
attendance, but had still managed to imbibe quite a few
drinks. Quite tipsy, they were driven home by Jack’s
co-workers. They were sitting in the living room having
a nightcap.

“Say Janice help me undo this dress will you?”

The costumes were true antebellum period pieces and
even with each others help had been difficult to get
into properly. There was no way that they were going to
get them off alone.

“Sure thing.”

Jack’s petticoats rustled as he moved over beside Ray
in the green satin brocade gown he wore. Ray’s was made
of red velvet and white lace. Ray turned away and
lifted up his hair as Jack worked on undoing the row of
tiny buttons down his back.

“Boy I just don’t see how women lived in these things a
hundred years ago.” Said Jack.

“Well they had maids to help them dress and undress.
Sort of like I will. Say you’d better get used to doing
things like this.”

“First let’s see how you do at it.”

The boys shifted and Ray undid Jack’s buttons. They
both stood up and slipped off the heavy gowns.

“Whew. It’s a relief to get out of that.” Said Jack
standing there in his petticoats. “I’m thankful
Halloween only comes once a year.”

“Well there’s still Mardi Gras.”

“I think I’ll be a bunny for that.”

“That is if I don’t have you go as Fifi the French
maid. Parlez Vous?”

“Just shut up and undo this corset.”

Jack had lowered his petticoats and was standing there
in satin pantaloons and an old-fashioned corset that
tied in back. The boys had been sticklers for
authenticity this evening. Jack breathed a sigh of
relief as he was released from its vise-like grip. He
pulled the down the top which had f****d his breasts up
into the dramatic cleavage which had been flaunted by
his gowns low cut bodice.

Ray felt a stirring in his loins and it dawned on him
that he was getting aroused on watching his roommate
undress. Ray released his breasts from the corsets
restraint and noticed that his nipples were stiff.
Sally had told him that sexual excitement might
manifest itself like that. He was a little embarrassed,
but with his senses dulled by alcohol, getting turned
on watching Jack undress his now resplendently feminine
body, somehow didn’t seem wrong or unnatural at all.

Jack sat back down on the couch.

“That’s better, but these damned shoes.”

They had of course worn buttoned-up high heeled shoes.

“Let me get them off for you.” Said Ray.

Ray left the room and returned with tool to undo the
buttons and finally got one off. Jack moaned as
circulation reestablished itself in his foot. Not fully
aware that he was entering dangerous territory, Ray
said “Here, let me rub it for you.”

Ray picked up Jacks right foot, noticing how cute it
looked with its red toenails inside sheer hosiery, and
started to massage it.

“Oh Rachel, that’s tremendous.” Whispered Jack.

“Just sit back and enjoy it Janice.”

Ray got the other shoe off and massaged Jacks feet.

“It’s your turn Rachel.”

Ray lay back on the floor and let Jack get his shoes
off and work on his feet. It did feel wonderful. Jack
stopped and Ray just lied there. Ray was shocked to
feel a hand on his breast. He opened his eyes to see
Jack alongside him on the floor.

“What the…?” Ray started to say, but as he looked
into those deep blue eyes he realized beyond a shadow
of a doubt that he truly loved Janice. Their lips met
in a lingering lipstick smearing kiss, each one of them
ignoring the fact that he was just as pretty and
desirable as the make-believe woman he was kissing.
They didn’t go any further, but lust lay in each others
arms sharing their closest secrets, and enjoying the
intimacy. They continued to drink and cuddle.”

Ray woke up the next morning shocked to discover where
he was. In Jack’s satin sheeted king-size bed, naked
except for his cache-sex, with Jack’s pretty blonde
head in his arms, cradled to his breasts. Looking down
Ray saw that Jack still had his cache-sex on.

“Well at least nothing happened.” He thought to himself
relieved.

Ray’s attempts to extricate himself woke Jack up. Jack
opened his eyes and saw him.

“Hi Rachel.”

“Er… what went on her last night.”

“Just a little smooching is all I can recall.”

Ray looked at Jack and felt himself overcome with the
infatuation he had experienced the night before. He
moved closer to Jack and Jack wiggled up beside him.
Once again they were in a lip-lock.

“What’s happened to us?” Thought Ray as Jack’s tongue
investigated his mouth. He didn’t get an answer as this
time their cuddling led to caresses.

Ray was in seventh heaven as Jack sucked first one
plump nipple then the other, but he felt ready to bust.

“Excuse me Janice”, Ray said and got up and ran to his
room. Once there he stripped off his cache-sex letting
his cock free. Not having had any sexual stimulation
for some time, Ray was distressed at what had become of
his cock. What had been a proud specimen of manhood was
now just an atrophied little thing. He grabbed it
anyway and proceeded to jerk off. As he came the image
in his head was that of Janice.

“We’ll just keep it at this level.” Thought Ray.

Good intentions can only take you so far though, and it
wasn’t long before the boys didn’t bother to leave the
bed before masturbating. Then one night Jack reached
down and grabbed a pair of satin panties. He wrapped
them around Ray’s cock saying, “Just sit back and relax
Rachel”, then pumped Ray to orgasm. The progress of
this affair was predictable. Soon Ray had moved into
the other bedroom off of the bath.

After that, they would usually spend the night together
in one or the other’s bed. Due to their hormone
regimens, neither of them could attain a hard enough
erection to accomplish penetration, but they were soon
lovers, each pretending to himself that he was in love
with a beautiful girl while delighting in the sex
available to two boy-girls. Their make believe romance
continued to grow unabated.