Crossdressing Vignettes True Story
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Crossdressing Porn Story 2. free porn video
Jack let himself in the front door. It had been a long
day at the store. He’d noticed Ray’s Porsche in the
garage.
“Honey, I’m home.”
From the kitchen came a sweet “Hi Janice how was your
day.”
“Pretty rough.”
“Well just sit down on the couch and relax. I’ll have
dinner ready in jiff.”
They had divided up the house chores and Jack was glad
that Ray had taken over the cooking. The meals were
always delicious.
Ray walked in with an apron over his office dress
carrying a tray with glasses and a pitcher of Martinis.
He poured one for Jack.
“Here. This will take the edge off of my poor baby’s
day.”
Jack kicked off his high heels and took the proffered
glass, as he sipped it, Ray pushed Jack’s mass of
blonde curls out of the way and started rubbing his
neck. It wasn’t long before Ray was on his knees
massaging Jacks cramped feet. Pretty soon he had worked
his way up those long legs and pushed Jacks short skirt
up around his hips. Pulling down the pantyhose and
panties revealed Jacks tiny hairless organs.
Neither boy had any hair below his thin, highly arched
brows by now. They had purchased a home electrolysis
kit and loved to examine each others bodies, searching
for and removing any stray hairs. Ray lovingly took
Jack’s tiny cock and balls between his red glistening
lips and sucked him to orgasm as Jack enjoyed his
martini. Ray felt a stirring in his panties as he
thought about how Janice would return his loving after
the dishes were dried and put away.
How could two lovers continue with a contest such as
theirs? They couldn’t, and at a party at their home for
the TV group, Ray announced that the bet was off.
“To prove that we’re not quitting cause we can’t take
it, Janice and I will remain in dresses and keep our
jobs for another year.”
The group applauded loudly. Jack and Ray had become
heroes to all the crossdressers who knew them, living
the life that each of them wished he could.
“Could I ask you guys a favor?” Asked Sally, later in
private.
“Sure,” replied Jack.
“Well since your bet is called off I was wondering if
you still could use a maid for a year?”
“What are you talking about?”
“Well it’s kind of a long story, but I’ve finally
decided to go ahead and become a woman permanently.”
“Congratulations!”
“There’s more to it than that. Before I can get
approval for the surgery I have to live and work for a
year as a woman. I can’t practice medicine as a woman
until I change my licenses, and I can’t change them
until I have the operation. It’s a Catch-22, so I guess
I’ll take a year off. I’ve got plenty of money, but
don’t know what I could do. If you’ll let me work for
you and give me the recommendation I need, then we’ll
all wind up with what we want.”
“Why sure. I guess… What do you think Rachel?”
“It’s fine with me.”
Sally moved in, took over the housekeeping duties, and
became, if you will, a father figure with a figure to
the two young men.
Before they knew it, it was Christmas and Jack and Ray
decided that, since they were the only family each
other had, they would start a tradition and spend every
Christmas together, exchanging gifts on Christmas Eve.
Ray gave Jack a full length mink coat while he received
diamonds; studs for his ears, a tennis bracelet, a
necklace, and a huge ring.
Wearing nothing but his cache-sex, Ray paraded around
the bedroom, modeling his new jewelry.
“Does this ring mean we’re engaged?” He joked, admiring
the big sparkler.
“No. It’s a friendship ring, but if you ever do like
Sally and go all the way, consider yourself engaged.”
“Well that’s not for me, but if you ever do it, I
promise that I’ll make an honest woman of you.”
This couldn’t go on forever and the relationship hit
the rocks shortly into the new year. Ray attended an
office party. He’d worn a revealing little black dress
and delighted in vamping his staid male colleagues. Ray
had too much to drink and wound up being driven home by
Ken Myers, a timid and unassuming law clerk. When they
pulled up Ken stopped the car.
“You know Rachel I’ve always thought you were cute, but
until tonight I had no idea just how beautiful you
really are.”
“Why thank you Ken, that’s very nice of you to say so.”
Ken got out, came around, and opened Ray’s door. Ray’s
dress, short to begin with, had ridden up his thighs,
and Ken could not help but gawk at Ray’s long nylon
covered legs as they swung out the door. Swallowing
hard, Ken escorted Rachel to the door. Once there he
was in obvious discomfort as he blurted out, “Rachel do
you think it would be O.K. if… er, uh, would you go
out with me sometime?”
“I don’t think so Ken.” Ray felt sorry for the shy boy
and decided to give him something to remember.
“But thanks for the ride home.”
Ray put his hands on Ken’s face and drew him closer
where their lips met and Ray gave him a big hug and a
long searching soul kiss. Just then the door opened and
the light went on. Ken and Ray looked up to see Jack
standing in the doorway with a with a shocked
expression on his pretty face.
“Uh, I’d better be leaving. Good night Rachel.” Said
Ken as he backpedaled to his car.
Ray entered the house and shut the door behind him.
“Just what the hell do you think you were doing out
there Ray?”
“Please call me Rachel, Janice.”
“No. I think all this pretending has gotten out of
hand. It’s bothered me at times, but until tonight I
could ignore it. Let’s face reality. I’m Jack and
you’re Ray and do you realize what we have become?
Well, I’ll tell you what we are. A pair of little
faggot cocksuckers. I could overlook the fact that you
aren’t really a girl, but this is too much. How much
longer before you’re seducing men in our house? Why I
bet you’ll even be trying to fix me up before very
long.”
“Oh Janice it wasn’t like that at all.”
“Oh sure it wasn’t. Ever since you moved in with me
you’ve lured me further and further into this mess. All
I wanted was to dress up once and awhile and look where
you’ve taken me; I’m a girl who happens to have a cock.
If I don’t watch my step I’m liable to wind up being
fucked up the ass by one of your boyfriends. Well, I
may have gone too far, but I’m not going any further.”
“Janice. Please…”
Jack turned and ran upstairs to his room.
Ray was on the couch crying when Sally came in to
investigate the noise.
“What’s the matter Rachel?”
“It’s Janice.”
“What about Janice?”
“She doesn’t want to be Janice anymore and I don’t
blame her.”
Sally sat down on the couch, took Ray in her arms, and
hugged him.
“There, there. Tell Aunt Sally all about it.”
Ray tearfully related the entire story, going back as
far as his first meeting with Jack. When he was done he
laughed.
“What’s so funny?”
“I just realized that I’m acting exactly as a girl
would.”
“Rachel, you’ve been living as a woman in a woman’s
environment for quite some time. No psychologist worth
his salt would be surprised to find you responding like
one.”
“That may be, but I guess it’s back to being plain old
Ray again.”
“Now don’t be so fast young lady that you throw the
baby out with the bath water. You’re young, you’re
pretty, and you can pass. Do you know how many of the
old-timers in the group would k**l to be able to live
as you are living. Look, you’ve the rest of your life
to be a man, but this chance will never come again.
Take advantage of it while you can.”
“I’ll think about it.”
“Don’t just think about it. Get away from here for
awhile. I think you and Janice just need to get away
from each other for awhile.”
“I think Janice it getting away from me forever.”
“Oh, I’ll go have a talk with her tomorrow. Don’t worry
about it.”
Ray went to bed and cried himself to sleep and by the
next morning he had decided to take Sally’s advice and
stay as Rachel for the time being, and also to go back
east for awhile. He went to Sally’s room the next
morning.
“Sally tell Janice that I’m going to New York to clear
up some family business. Tell her also that I love her
and will miss her.”
Ray removed the big diamond friendship ring from his
finger.
“Give this to her. Tell her I’ll be back for Christmas
and if she still wants me to have it, I’ll be glad to
take it back.”
“But Rachel it’s only May. Isn’t that too long to be
gone?”
“Long enough for the two of us to find ourselves and
make up our minds about what we want.”
Ray didn’t even pack. He put on a dress, made up his
face, and called a cab for the airport. He took only
his checks, his credit cards, and his emergency cash
stash; He’d buy what he needed in New York.
CHAPTER 10
Ray had made up the story about family business in New
York. Melancholy and despondent, he needed to get away
from Jack and get over the quarrel they’d had. After
arriving in New York and staying in a hotel, Ray sublet
a small apartment. He picked a psychologist out of the
yellow pages and made an appointment. He wanted to
extricate himself from the persona of Rachel, with
which he had become so confused that he couldn’t sort
it out on his own.
“Mr. Hirsch, and in all honesty let me say that I feel
uncomfortable addressing you like that dressed as you
are, I do not feel that I have the necessary background
to deal with your case. It is like no other that I am
familiar with. You suffer from a severe identity crises
brought on by having lived as a woman for over two
years. However, I do know of a clinic where they
specialize in cases like yours and I’d like to refer
you to them.”
Ray departed a cab outside the Institute for the
Amelioration of Gender Dysphoria. He looked up for a
moment at the imposing building, smoothed his skirt,
and went in.
Inside a pretty receptionist looked up.
“Hi may I help you?”
“Yes. My name is Ray Hirsch and I have an appointment
for a referral.”
“My name’s Nancy. If you’ll just fill out these forms
we can get started.”
Nancy watched Ray as he took the psychological profile
test.
“Wow If I didn’t know he was a boy I could never have
guessed it. he’s one of the best I’ve seen and I’ve
seen some of the best.” She thought to herself.
Nancy looked at the reason for referral.
“Unable to return to masculine role. Why would he ever
want to?”
Nancy picked up the phone.
“Hello Leslie? You should see the one that just walked
in.”
“O.K.”
Nancy starred the top of Ray’s folder, thinking “He’s
to pretty to be a boy.”
Ray looked up to find a beautiful woman standing in
front of him.
“Hi. Done with the test?”
“Uh, yes ma’am.”
“Oh don’t be so formal. My name’s Leslie.”
“I’m Ray, er Rachel.”
“Around here all us guys use girls.”
Ray was amazed. “Are you a guy too.”
“Sure am. One-hundred per cent all American male.”
Ray found this hard to believe.
“So your from California?”
“Just recently.”
Leslie looked over Ray’s record.
“So… you’re having trouble getting in touch with your
old male self again. I take it you don’t want to live
as a girl any longer?”
“I’m not sure anymore what I want to do.”
“Well, I hope we can help you find what it is you’re
looking for. In the meantime, let me invite you to
dinner to welcome you to New York.”
“I’d like that.”
“Good. Shall we say Saturday at eight.”
Ray rode the elevator up to the penthouse. He’d found
out that Leslie was the director of the Institute and
fantastically wealthy. Wanting to impress his host, Ray
had spent the morning shopping for a dress and the
afternoon in a salon. The dress was shorter than he
usually wore, but this was New York and he had the legs
for it.
Leslie met Mike at the elevator along with another
woman. Both wore evening gowns. Mike was in awe of such
glamour.
“Rachel, may I introduce my wife Amanda.”
They enjoyed cocktails while Ray took in his
surroundings. The penthouse was a dream; a totally
feminine environment. They made small talk about
California and New York until Amanda announced that
dinner was served.
“This is the best meal I’ve had in ages.” Ray
complimented Amanda.
“Why thank you, but it’s nothing at all.”
“You mustn’t say that dear. This is outstanding.”
Leslie told Amanda.
“Amanda’s become quite the cook since I married her.”
He told Ray.
“Rachel I invited you here tonight not only to get to
know you but to show you first hand one of the options
available to you.”
“And what is that.”
“As you know; I am a man. What you do not know is that
my wife used to be a man.”
Ray looked at the beautiful woman across the table from
him.
“You’re kidding me”
“I would never do that. Darling?”
Amanda spoke up, “It’s true. My name used to be Michael
Watson. After sex reassignment and a disappointing
experience with another man I fell in love with and
married Leslie.”
“Do you like it?”
“Which; being a woman or being married?”
“Uh, both I guess.”
“Well the answer is the same either way. I have never
been happier and I feel totally fulfilled. I love my
life now and see that this is my proper role. Any other
lifestyle would merely have left me as I was; lonely,
depressed, and unfulfilled.”
Ray considered how that those terms described his
emotional state of late.
“Are there a lot of guys like me around?” Ray asked
Leslie.
“Oh yes, It’s the main reason for the Institute and we
have helped hundreds if not thousands of people like
yourself. In fact, every employee of the Institute is,
or at some time was a man.”
“Everybody?”
“Yes.”
“What about the receptionist Nancy.”
“Especially Nancy. Until quite recently she was Dan.”
“Wow.”
They made small talk throughout dinner. Dessert was
offered, Amanda declined saying that she had to watch
her figure, and when coffee was served she excused
herself. Ray watched the enchanting brunette leave,
still finding it hard to believe that she could ever
have been a man.
Ray and Leslie carried their coffee to the sitting room
where they resumed their discussion.
“So I assume you wanted me to see how you live to show
me that I could stay Rachel, find a girl, and settle
down. Sort of put myself in your shoes.”
“Not really.”
“Then what?”
“I wanted you to meet Amanda. To see that you could
live happily as a woman. As you put it, to have you put
yourself in her shoes.”
“You mean change my sex and get married?”
“Not necessarily to get married, but your psychological
profile shows us that you are much more comfortable in
the female role and that you are still deeply in love
with your former roommate. You indicated that you feel
that he still loves you, but can’t deal with the fact
that you are men, despite your appearances. Now if you
were a woman, I’d bet that he could overcome his
homophobia and that you could subsequently have an
wonderful relationship with him, much as Amanda does
with me.”
“Oh, I don’t think so Leslie.”
“Well I’m not going to push you into anything that you
do not want, and you don’t have to make up your mind
tonight. I just wanted you to see what’s possible.
You’ll meet your counselor Monday and she will cover
all the bases with you. Gail is just the one for you.
She was married when she was a man and now she’s
married again. Be sure to pick her brain, having been
up the aisle in a both a tuxedo and a gown I am sure
that she can give you a good picture of what it’s like
from both sides.”
CHAPTER 11
“Gail I want you to know what a difference you have
made in my life. These past weeks have cleared up so
much. I know now that I’d never be truly happy as Ray
and I wanted you to be the first to know that I have
decided to go all the way and become a whole woman.”
“Oh Rachel, I’m so happy for you. Let’s see, you’ve
already lived as a woman for over a year so we can
waive that requirement. I’ll certify you as mentally
competent and that takes care of the formalities. We do
our own surgery on the premises so all you have to do
is pick a date.”
“All I want is to be healed up by Christmas. Is that
possible?”
“Of course. Recovery takes about six weeks. Give
yourself another four weeks to get your strength back
and become familiar with your new plumbing and you’ll
be ready for anything, and I do mean anything.” Gail
winked at him. “You could wait a couple of months to be
sure and still be done before Christmas.”
“No. I’m sure. I’d like to get this over with as soon
as possible.”
“Great. How about a week from Monday?”
“That’s fine with me.”
“OK it’s a date. By the way do you have those tapes I
lent you?”
“Right here in my purse.”
Ray handed them over the subliminal tapes that had been
responsible for his change of heart concerning his
change of sex.
“I don’t know if they did any good. I took the sleeping
pills you gave me and always fell asleep before I heard
anything.”
“Maybe it’s just as well that you don’t know how much
they helped,” thought Gail to herself as she took the
tapes from the boy. “Can’t have these getting into the
wrong hands.” It was amazing how fast and thorough
those tapes were. Any man exposed to them would soon
beg to be made into a woman, and they hadn’t figured
out how to turn it off once on. Gail thought about how
she had been exposed to them by her ex-wife.
The passage from masculinity to femininity was a
painful one for Ray, but when it was over, the fact
that he had been a man seemed like ancient history to
him. After recovering from surgery, he did what any
girl in New York with unlimited funds would do; he went
shopping. He had lost still more weight, and his body
appeared to have stabilized at a size 7.
Ray went to the best stores and filled out his
wardrobe, or as he began to think of it; his trousseau.
Remembering Jacks proposition, he considered himself
engaged. One day on impulse he walked into a jewelry
store and tried on engagement rings and wedding bands.
He wished he hadn’t returned the ring to Jack.
Inspired, he went on from there to venture into a
bridal salon and try on wedding gowns.
Ray admired himself in the mirror; he was captivated by
the way he looked in the long ivory satin gown.
“I’m going to be the best wife to Jack that there is,”
he thought to himself.
Then he spoke aloud what would someday be his name.
“Mrs. Jack Doyle.”
Ray liked it. It seemed to roll off of his tongue just
right.
CHAPTER 12
The house seemed like an old friend to Ray as he let
himself in the front door.
“Janice? Sally?”
“I guess they’re out.”
Sally had kept in touch and had let Ray know that Jack
was home and looking forward to his return. Ray went up
to his room; it looked like he’d only been gone a day.
Looking at the closet, ray wondered where he’d put all
the dresses he’d brought back from New York. Ray took
off for his appointment at the salon.
The next day was Christmas Eve and by previous mutual
agreement dinner was a formal affair and no effort was
spared. Sally had known that the boys would be back and
had cleaned the house until it shone, cooked for two
days, and would serve them their Christmas meal in her
formal uniform.
For their part, Jack and Ray each purchased new gowns,
their long manes had been styled into elaborate
coiffures, their fingernails were filed to long points
and polished to a ruby gleam, and each had been
expertly made over by his favorite beautician.
Ray and Jack saw each other for the first time when
they came down to dinner and each was immediately
captivated by the stunningly beautiful woman across the
table.
Ray saw the look in Jacks eyes and recognizing it as
desire thought. “Great. He still wants me.”
Jack had obviously lost some weight, but seeing the
cleavage visible in the decolletage of his strapless
gown Ray thought, “Jack must still be taking hormones
to look like that, but I don’t care; I love him as he
is, no matter what he looks like.”
Ray thought about what it would be like to satisfy Jack
as a woman. What would it be like to have his newly
created womanhood penetrated by Jack’s cock? To have
his insides filled with pumping come? Would he enjoy
it? His speculations were interrupted by Sally.
“I’m glad you guys are back because I have some good
news. I underwent my surgery while you were both away
and I’m a girl now.”
Jack and Ray applauded and congratulated her loudly.
Ray wanted to share with her that he was also, but he
was saving that revelation as a surprise for Jack. It
would be his Christmas present.
“Hold it, hold it. There’s more. You remember Ben from
the group? Well he’s asked me to marry him and I’ve
accepted. I want you guys to be my bridesmaids. Will
you?”
They both agreed enthusiastically. Ray had wanted to
ask her if she would do the same for him, but kept his
mouth shut.
The boys made idle chitchat during dinner. Sally
cleared the remains away and left them sipping eggnog.
“You guys don’t mind if I take off?” Asked Sally. “I
have a date with my fiancee.”
“So do I” Thought Ray.
“No by all means go,” said Jack, “and give our regards
to Ben.”
“So how was New York Rachel?”
“Full of changes. You just wouldn’t believe it. How was
your summer?”
“Oh I went to Colorado and spent time hiking the
mountains and rafting the rivers among other things.”
“Well it looks as though it agreed with you.”
“Oh I’m positive it did. It changed my whole outlook on
life.”
“Am I correct in assuming that your being here tonight
signifies that you have at least some interest in
resuming our relationship?”
Jack gave a high-pitched giggle and licked the rim of
his cup seductively.
“Well things can never be exactly like they were
before, but to answer your question; Yes. I would like
very much to resume our relationship.”
Ray felt Jack’s stockinged foot caress his inner calf,
and as Jack played footsie with him, Ray’s spirits
soared.
“Well then, in keeping with our tradition, if one time
can establish a tradition, I would like to exchange
gifts tonight. If you’ll come up to my room later, I
will have yours ready for you.”
“Excellent,” replied Jack. “I’ll give you yours then
also.”
Ray excitedly stripped off his evening wear and attired
himself in a lingerie set made of red satin. He stuffed
his breasts into a bra with no cups, then wrapped a
garter belt around his tiny waist. After pulling smoky
nylons up his shapely legs he hooked them up and
slipped his feet into silver lame spike heels. He then
stepped into and pulled up a pair of crotchless panties
to complete his look.
Ray laid on the bed in a provocative posture and
positioned a silk coverlet so that it discreetly
covered his altered genitals. There was a soft knock at
the door which connected his room to the bathroom.
“Come in, my side is open.”
Jack entered through their connecting door and looked
at Ray. He had a provocative look on his pretty face,
and Ray could tell by the way that Jack’s plump nipples
were standing at attention under the thin silk robe,
which he wore tied with a sash, that he was hot and
ready for anything.
“Well Jack. Do you mind if I call you Jack? I really do
want to start thinking think of you like that. Here’s
my present. My panties are crotchless.”
Ray threw off the coverlet.
“And so am I.”
Ray’s conversion was exposed to Jack’s gaze.
“I am all woman now Jack and I am all yours.”
Jack froze and seemed to blanch. He gawked at Ray and
there was an look in his eyes that Ray had never seen
before and it alarmed him. It wasn’t astonishment,
rejection, condemnation, revulsion, or any of the other
reactions that Ray had steeled himself to receive.
Instead Jack just stared at him in an odd manner.
Ray got up off the bed, and ran to Jack, embracing him.
“Jack, darling,” he cried, “don’t look at me like that.
You said that Rachel was the girl you wanted to marry.
While I was away I found out that I love you so much
that I couldn’t live without you, so I became Rachel.
For you Jack. Say you still love me and let’s be
happy.”
Jack looked about as if he did not know where he was.
He slowly came out of shock and hugged Ray.
“I’m sorry about what I said about being us being
faggots and all that. I want you to know that I love
you deeply and that nothing can make me love you any
less, but right now I think that we should go
downstairs and have a drink.”
“Oh Jack. Don’t be so serious. It’s Christmas Eve and
I’m your present. I’ve been dreaming about this day
ever since I had my surgery… Or is it that you don’t
want me like this?’
“Oh no, never. It’s just that…”
Jack was sniffling.
“Oh what the hell! Merry Christmas!”
With tears welling up in his eyes, the now sobbing Jack
let go of Ray, stepped back, and untied the belt of his
robe, letting it fall open. He wore nothing underneath,
which revealed… nothing! Instead of the manhood that
Ray longed for, there was only a furry patch of blonde
pubic hair.
“Ray, I went to Colorado and became Janice for you. I
knew I loved you and that there had to be a change and
I thought that I’d have to be the one to make it.”
Jack cried out loud.
“I wanted to take you up on your offer to make an
honest woman out of me, but…”
They hugged each other and cried for awhile and then
the two girls, who had once been Jack and Ray, but were
now irreversibly Janice and Rachel, went looking for
some booze.
And so concludes the fable of these two foolhardy young
men who so recklessly sacrificed for each other the
most fundamental component of their personality. Now
every fable must have a moral and this one is no
exception: When you’re giving someone a present, make
sure that it can be exchanged in case of duplication.
Latisha
- 09.02.2022
- 8
- 0
