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^Å.well, perhaps on second thought^Å"
"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^Å.you^Åto 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^Åa 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^Åand 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^Åmore 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^Åmy 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