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Date: Tue, 30 May 2006 05:43:26 -0700 (PDT)
From: Wendi Robertson <wendi_robertson2003@yahoo.com>
Subject: The Breakup (TG)
I had just had my 25th birthday when Mary, the woman I hoped to marry,
suddenly broke up with me. I was devastated. I thought she loved me as
much as I loved her. But, I soon found out she had been two-timing me.
The first few nights after our breakup I would wake up several times during
the night sexually aroused with my darling Mary on my mind. I would
masturbate every time thinking of us being together and having sexual
intercourse (something that never quite happened when we were going
together). About a week after our breakup I woke up one night with the
hardest erection I had had in perhaps a year. The last time I had been so
sexually aroused was when I still cross dressing in private. Those
thoughts of the past year overwhelmed me and I furiously masturbated to a
quick and very intense orgasm. As I ejaculated, I cried out, "Oh fuck, I
want so to be a woman!"
As I came down from my orgasm I rubbed my semen all over my groin and
tummy. I thought: why would I again involuntarily cry out those words? I
mean, my relationship with Mary had "cured" me of cross dressing and
"proved" that I was a normal young man who wanted to be with a caring
woman. Then, another more repressed thought entered my mind: that of my
first serious cross dressing experience of 6 years ago when I was dressed
so sexy. I masturbated 5 times during that night and never came down from
my feminine high. I was so charged up I did not want to take off my sexy
intimate apparel. My first climax that night I cried out about wanting so
to be a woman. During my second masturbation I began bouncing my ass on
the bed and suddenly realized I wanted a man mounted on me, coupled in
sexual intercourse as man and wife.
But, the next day those 6 years ago I put those thoughts out of my mind
because it was simply too homosexual. I didn't want to be a queer. I
didn't think I was a queer; rather I just had a cross dressing fetish. I
did continue to dress often at night, though, over the years until I met
Mary. Once I started falling for her I trashed all of my women's clothing.
I knew I was cured!
Within two weeks of my breakup with Mary I was shopping here and there
until I suddenly had a very complete woman's wardrobe, including a
transvestite panty girdle with padded hips and buttocks! This time I
bought high heel shoes, a very pretty blonde, Paige-boy wig, and a very
good makeup kit. I really worked at dressing to "the nines." I would not
immediately seek masturbatory relief as I had done when dressing before I
met Mary. Rather, I would sit around the house fully dressed and made up,
reading women's magazines and watching women's shows on television. I
simply loved the feeling and appearance of my wonderfully padded
transvestite girdle!
The typical evening would end with my legs spread as I sensual fucked
myself with my wonderful, very life-like rubber penis. I would often
perform oral sex on the rubber penis, almost worshiping it with my mouth!
The sexual phase of my evening would end with me furiously masturbating my
anus with my rubber cock, and beating off my sissy boy peter with my right
hand. I never fisted by little penis like real man do with their cocks;
rather I would be so dainty in stroking it with my thumb and forefinger. As
I ejaculated all over my tummy, my desire to a strong man's cross-dressed
sissy grew stronger with each passing night.
Over the following weeks I developed a pattern of rushing home from work,
and transforming myself from Jimmy to Wendi. I actually began to feel that
I was more female than male, at least in my thoughts and desires. I would
often look at myself in the mirror for long periods of time, realizing each
time that I was not a woman at all, but a very inadequate man who had found
a very, very wonderful escape into mock womanhood!
One night, after an especially wonderful session of dressing and applying
makeup I decided to delay fixing dinner and, instead, have another
cocktail. I proceeded to get a bit tipsy. I was watching an old romance
movie on television. A particularly sensual scene showed the handsome
leading man embracing the beautiful leading woman. He was feeling her up
as they kissed passionately. Suddenly, I was afire with sexual desire for
a man! I wanted to be a real man's submissive, mock woman! My small,
inadequate penis was rock hard. I worked under my skirt, slip, and
panties, and adjusted my cock so it was flat up against my tummy. I then
lightly rubbed it through my skirt as I watched the man continue to seduce
the woman in the movie.
I impulsively picked up the telephone and called my good friend Raymond,
who lived four apartments down the hall from mine. Ray was 5 years older
than me and was divorced. He was everything I was not; tall, handsome,
athletic, and women seemed to fall at his feet.
"Hello," said Raymond as he answered the phone.
"How are you doing Ray?"
"Fine, Jimmy, it's good to hear from you."
I said in a somewhat coy tone of voice, "Ray, may I tell you something if
you promise not to laugh too much?"
"Sure Jimmy. We are best of friends. What is it?"
"I am sitting here wearing women's clothing, makeup and a wig and I can no
longer keep it a secret."
There was a long pause, then Ray said, in a slower, more deliberate,
serious even, tone, "Jimmy, I would have never expected that of you^�.well,
perhaps on second thought^�"
"Oh, Ray, am I being silly? Have I ruined our friendship?"
"Not at all, Jimmy. In fact I want to see you `en femme' as they call it
in Hollywood."
"Oh, Ray, I was hoping you would want to see me and not be mad at me."
"I'll be right over Miss Jimmy."
Soon Ray was at the door. I was so nervous. I opened the door, blushing
deeply as he came in and really looked me over.
"Wow, Jimmy, you can't pass but you really do look good!"
"Oh, Ray, thank you! You don't find it all too silly?"
He suddenly took me in his strong arms and said, "To the contrary, I find
this^�.you^�to be very exciting! I know all about transvestites, dear."
Ray suddenly French kissed me as he cupped my buttocks and pulled our
groins together. It was so romantic. He broke off the kiss and whispered
in my ear, "You know that wearing the dress means you must learn to take
the dick!"
I hung my head and blushed profusely, softly saying, "I kind of figured
that, Ray. But, hearing you say it removes any doubts I may have had about
it. I now know beyond any doubt that I am queer."
"Yes, you are quite queer, my dear Jimmy, "Ray said softly and with
kindness and passion in his voice as he kneaded my ass cheeks, with our
groins rubbing together. "You know you must suck my cock now that you have
let me see you in the dress."
As Ray said this, he placed his hands on my shoulders, gently forcing me to
my knees. Once there he unbuckled his belt, then unzipped his fly. The
sound of his zipper opening, right in front of my face, caused me to have
sexual feelings more intense than I had ever felt when with a woman. Ray
dropped his pants and shorts, exposing to my wide eyes a very sensual, very
manly, and very erect penis. It was about 7 inches long, cut, and utterly
delicious looking. I instinctively kissed my first cock, then licked up
and down the shaft and kissed his balls as he held the top of my head and
made manly moans.
I then swirled my tongue about Ray's cock head. I took special care to
tongue the slit, which caused him to say in a low, guttural voice, "Oh
Jimmy baby! You are a natural, honey^�a real womanly cocksucker!"
His saucy words caused me to squeeze my legs tightly together and I felt
contractions deep in my anus. I instinctively made soft, high-pitched
sissy moans as I began to work my mouth, tongue and lips and down the rigid
shaft of his dick. Suddenly, he pulled out of my mouth and began to
playfully slap my face with his cock!
"Do you have any lubricant, baby?"
I looked up into his eyes and softly confessed, "Yes, Ray, a tube of K-Y I
use to finger myself with^�and for my dildo, too."
"Get up sissy baby, and let's get the K-Y and then go to bed as man and
woman!"
I went to the bathroom and got the tube of K-Y and handed it to him. He
then led me by the hand to my bedroom.
"Pull down the covers, girl, and take off your shoes. Lie on your back, my
sissy cunt-boy!"
"Sissy cunt-boy" shot through me like a bullet! I was flush with
embarrassment and humiliation, yet so, so sexually excited. Ray mounted me
and pulled up my skirt and slip. He felt up and down my nylon-clad legs
and snapped gently at the garters of my garter belt.
"I love your real nylon stockings, sexy garter belt and black silk panties,
Jimmy. Only a true womanly queer would attend to such sexy, provocative
details. And, your padded transvestite panty girdle is absolutely
stunning!"
He pulled my padded girdle panty and satin panties off. He sniffed and
licked the crotch of my pretty panties. He then threw the panty girdle on
the floor and placed the satin panties on the pillow, under my head. He
gently squeezed my throbbing hard little cock, saying, "My goodness, Jimmy,
you do have a small cock^�more of a cockette, actually."
I whimpered, "Is it too small for you Ray?"
"Oh no, Jimmy baby! Not at all. It makes it impossible for you to be a
man, but it is delightful as a clitty cockette for a sissy who wears
women's clothes. You are my sissy, now. Put your legs over my shoulders,
baby!"
I followed my man's bedroom instructions. He took gobs of K-Y and coated
his throbbing hard cock. Then, he fingered more K-Y into my ass pussy. I
thought I would climax in my ass as he began to slowly finger my anus. My
cockette twitched and felt so, so good as he continued to finger my ass.
In a begging, whimpering, high-pitched tone I said, "Oh Ray, fuck me now,
please darling, fuck me and make me your girlfriend!"
He pressed his cock head against my anus, looking me intently in the eyes,
asking, "What is your girl name, sweet sissy boy?"
Breathlessly, I softly replied, "Wendi."
"Take my cock, Wendi, baby. Take my hard cock!"
He slowly pushed his cock into my ass as I pushed back to eagerly accept
his manhood inside my sissy boy's mock vagina! Oh fuck, it felt so good.
I realized at this moment that Mary was quite right in rejecting me. I
knew now that I needed to take the cock just as much as she did!
As he slowly enter me he said, "Oh fuck, Wendi! Your ass pussy feels so
fucking good, honey! You are my hot fuck babe!"
Once Ray's 7 hard inches were fully inside me we were both quiet and still
for a few moments. I could feel his balls resting on my balls. I felt so
utterly homosexual and yet so womanly, too. This is where I was always
meant to be! I now knew my true place.
"Okay, Wendi, baby, this is your completion. Take my thrusting hard cock,
sissy boy^�my sissy boy in the skirt, my sissy boy taking the hard dick
like a real woman!"
With this Ray began thrusting inside me, slowly at first then building up
speed. I moaned and rolled my eyes, while licking my lipstick covered
lips. I wrapped my legs tightly about him. I felt so loved and
protected!!
"Oh Ray, yes! Yes, Ray honey, this is it! Fuck me like the woman I have
always wanted to be! I am a sissy boy woman! I am a dirty little panty
faggot!"
"Oh fuck baby, yes! You have such a dirty sissy's mouth and such a hot ass
cunt! Take my cock, baby!"
Ray and I become as one in the age-old rhythm of sexual intercourse. I was
being screwed by a real man; a sissy boy impersonating a woman by
submitting my ass to my real man! My darling Ray's thrusting was so
sensual, so masculine and powerful, and oh so incessant! I thrust back as
best as I could, like the weak sissy I was. I was truly experiencing what
hot, real women take for granted!
I cried out, "Give it to me, darling man. Give me your seed!"
Ray began those tell-tale short strokes, which I understood completely.
The room was filled with the music of bedsprings singing that erotic sound
of a couple having sexual intercourse! I felt my climax building in my
groin and anus. We both cried out in unison, "Oh fuck yes!"
With that I felt Ray's ejaculation filling me as he pushed his rigid,
ejaculating penis even deeper into me. He held it still as it shot copious
amounts of man seed into my sissy boy's vagina. Ray grabbed my little
erection and gave me some rapid strokes, which caused me to spurt sissy cum
onto his stomach. I also felt a radiant, feminine climax in my sissy ass!
We cuddled and kissed in our mutual after-glow of sexual intercourse. Ray
confessed to me that he had always been a latent homosexual at heart,
although he loved women, but nowhere with the sexual excitement and desire
had his first cross-dressed sissy brought him. He further confessed that
he had frequented homosexual bars frequented by drag queens and
transvestites but he had never gotten up the nerve to date a male woman, or
boy girl.
Raymond and I bought a nice home together and lived as man and wife for
many years. I would appear in public or with our friends as my male self,
but I was always cross dressed when home alone or with my darling Raymond.
Author's note: I'd love to hear from like-minded friends:
wendi_robertson2003@yahoo.com