My Very Good Friend

by Wendi Robertson

 

My good friend, Charles Dumont, caught me cross-dressed the other evening. I was so embarrassed! You see, Charles is a very handsome man and very intelligent. In fact, he is a psychiatrist.

Charles and I are both successful men in our early 40s. We are both married. Charles wife is a beautiful, sexually-charged woman who really knows how to dress and strut her stuff, so to speak (I have always envied that lovely woman so!) My wife is sweet, pretty, and quite naive. In fact, she was a virgin when we married or she would have never accepted my small penis and propensity to prematurely ejaculate after only two minutes, at the most, of sexual intercourse.

When Charles caught me I was alone, or so I thought. My wife Mary and Charles' wife Jennifer were on an overnight trip to attend a seminar. Charles was supposed to be tied up at the hospital with some visiting physicians. It was a perfect time, so it seemed, for me to engage in full makeup and dress-up, and goodness knows how I needed to release too many months of built-up sexual and emotional tension from being unable to really cross-dress properly. Oh, there had been my usual quick panty sessions and some private intimacies with "Mr. Dildo," while reading transvestite erotica, but not the rush of going "all the way" into womanhood.

Charles, Jennifer, Mary and I were such good friends we had keys to each others' homes. Charles' hospital session had unexpectedly ended quite early and he figured since we were both alone he would surprise me with a visit for cocktails and a dinner out. That is the how and why of his catching me with my panties up, so to speak.

Charles made me sit down with him and discuss the matter. I requested that I first remove my makeup and change back into my male clothing. Charles insisted that I sit beside him and remain fully made up and cross-dressed. A discussion ensued about my transvestism and my sexual desires. I was so embarrassed and quite uncomfortable as Charles treated me like his new patient rather than his life-long friend.

Charles, "Well, my dear Wendell, at what age did you first cross-dress?" (He called me "dear?" My goodness, did he intend to say that!?)

Blushing intensely, I replied softly, "At age 13 when I wore my sister's sexy one-piece swim suit."

"Did you masturbate while dressed in her swim suit?" he asked in a probing manner.

I looked down and softly replied, "Yes, Charles, I did."

Did you think of being with a man as his girl-like lover at that time, Wendell?"

"Oh, no, Charles, such thoughts did not enter my mind at all!"

"Did you think of screwing a woman as you ejaculated that first time wearing her swim suit?"

"No, Charles, I only focused on how good it felt to first be naked, then wearing only a woman's swim suit as I had my orgasm."

At what age did you first do makeup, lingerie, panties, padded bra, nylon hose, slip, and the dress, my dear Wendell?"

(Oh my goodness, he is calling me his "dear" again!)

"At age 19 Charles, and it felt so good and so natural, yet I also felt I was a pervert of sorts."

"What was your sexual fantasy when you masturbated at age 19 in full drag, my dear?"

I looked down, flush with embarrassment and humiliation. My embarrassment was intensified as I looked down at my pretty skirt, and sheer nylon stockings jutting out from beneath my skirt, my sexy high heel shoes on my feet, my painted false finger nails, and my woman's rings on my fingers. I suddenly became acutely aware of my throbbing hard little erection tightly constrained by my pink satin panties and tight-fitting panty girdle.

"Look at me, Wendell, look me directly in the eyes and answer my question!"

I looked up at him, and at that moment I felt so feminine and womanly and I was overwhelmed with romantic feelings and love for Charles, and wanted so to be his submissive lover! I softly replied, "Back then, Charles, as I beat off with my panties taut about my knees, and my buttocks squirming on the sheets, I suddenly wanted more than anything to have a loving, sexually aroused male atop me, crushing me into the mattress with his primal thrusts! As I ejaculated I could feel his fantasy penis ejaculating inside my nonexistent vagina; I would cry out, 'Oh, fuck, I want so to be a woman! Oh fuck, I need a man so very much!'" I hastened to add, "But as I came down from that orgasm I knew it was a lustful perversion; that I really desired a woman sexually."

"I see, Wendell. That is quite understandable. Did this become a pattern; that is, cross-dressing followed by masturbation 'en femme,' with progressing feelings of wanting a man mounted to your womanly self, and with that plaintive cry of wanting to be a woman at the moment of orgasm, followed by post-orgasmic denial?"

"Oh, Charles, I am so embarrassed…but yes, exactly."

Charles then noticed I was hiding something behind me. He grabbed behind me and wrestled the items away from me: a very realistic rubber penis, a tube of KY Jelly, a gay magazine with many close ups of erect penises, some ejaculating; and a transvestite pornographic magazine with many photos of effeminate transvestites in various sexual encounters with naked men. And, finally, there was a cuckold magazine showing quite explicit photographs of real men having sexual intercourse with the very willing, eager wives of small-dicked transvestites, and with the transvestites in various manner of assisting while dressed in sissified maid's uniforms.

Charles spent several minutes looking all of this over with great interest and care as I sat pulling my skirt down again and again, flush with embarrassment and thoroughly mortified and humiliated.

Presently, Charles commented, "Well, Wendell, the combination of all these items is pretty apparent. You obviously are sexually aroused not only by your cross-dressing but by your very strong desires to be as a woman with a commanding man. That is the case, is it not, Wendell?'

Yes, Charles…yes, it quite certainly is…" I could almost feel his eyes burning through my skirt and blouse directly to my vagina and supple breasts! This caused me to ever so slightly squirm my ass on the couch. I felt I would ejaculate inside my panties without even touching myself there.

"How do you use this artificial penis, Wendell? And, do you get great pleasure from it? Is it exciting to use and look at?"

I responded, "Oh Charles, those are such intimate, probing questions. But, I can't hide any of this from you, my best friend. Charles, I kiss the dildo, I rub it up and down my nylon-clad legs, I press it against my face and false breasts, I perform felleteo on it, and I even apply KY to it and screw my vaginal anus with it. Sometimes, when I screw my anus with it I ejaculate without even touching my small, rigid penis…so there…now you know!"

Soon, Charles diagnosed me as being a submissive, effeminate homosexual with a proclivity towards graceful passivity and with a strong feminine orientation. He characterized my condition as the state, in an informal sense, of that of being a male woman. That sounded both so incongruous and, yet, so exciting!

This was surprisingly followed by Charles taking me in his arms and full-mouth kissing me! Before I knew what was happening he had one arm around me and one hand going up my skirt! Oh, this really was good!

I broke away briefly and said, "But, Charles, you are straight and love your beautiful Jennifer so."

He hugged me and said, "Yes I love her, but I've always wanted you, Wendell. I've had a homosexual crush on you since high school dear boy! Now, that I know you are a homosexual, submissive transvestite I find you absolutely irresistible. Jenny can never thrill me like this, honey! Seeing my homosexual fantasy boy dressed wonderfully in women's clothing and so sweetly made up makes you hotter than Jenny ever could be, my dear transvestite pussy boy!"

I couldn't believe it! Charles led me by the hand to the bedroom. I awkwardly walked in my spiked high heel shoes trying to keep up with him. He deftly pulled down the bed covers making the bed ready for lovemaking! He gently forced me to lie on my back on the bed.

He felt me up all over, and he particularly played with my false breasts by unbuttoning my sexy silk blouse and cupping my satin bra cups with his hands. As he discovered that I was wearing expensive, supple silicon breast pads glued to my chest, he smiled and softly said, "Nice tits, baby, really nice transvestite tits."

Before I knew it my skirt and slip were up, Charles deftly removed my panties and panty girdle and he was fingering my anus with a lot of KY! He gently forced me on my back and he took off his pants and underwear, exposing to my wide eyes a handsome, very erect, very many penis! I swooned with girlish moans. Oh, the indescribably erotic and sensual feelings I felt the first time I got to see a real man's penis that was urgently erect for me!

He instructed me, "Place your legs over my shoulders, Wendell honey. There, there, now don't cry baby. We both need this so, and I will be so gentle honey. With this he slowly pressed his rigid cock head against my anus and I tried to relax as I had done many times with my dildo. I thought my little erection would just spurt right then and there as he slowly entered my anus, inch by inch until his manly balls were resting atop my little sissy balls! I looked him in the eyes and said, "Oh Charles am I your woman now?"

He responded with lust in his voice, "Oh yes, yes, Wendell baby! You are my boy woman, the desire of my life! Oh, fuck, Wendell, you are so tight and feel so fucking good! I've wanted you like this always, darling sissy boy! But even my fondest fantasies never had you all dressed in satin and lace and so pretty and feminine!"

He started small thrusts of his manly cock, so slowly at first, almost like he was teasing me! I whimpered and from out of nowhere I exclaimed, "Oh Charles, darling, I am your satin-panty sissy boy!" I couldn't believe how wonderful his hard penis felt deep inside me! Years of dreaming and fantasy were now our shared reality, and more erotic and fulfilling than I could have ever, ever imagined!

Charles started thrusting inside my vaginal anus a bit faster, "Oh Wendell, oh baby, yes! You are my satin-panty sissy pussy boy! Oh, honey, your boy pussy feels so much better than Jenny's hot pussy!"

I started crying with joy as my Charles told me his thrusting penis was mine, not Jenny's! I also thought about my Mary, and how she needed so a real man to fulfill her just as her homosexual sissy-boy husband was being fulfilled! Oh, the complex erotica of it all, thinking of Jennifer and Mary being fucked and then thinking of Charles and me coupled as man and woman! It was all so exciting!

My small, thin sissy-boy penis was harder than it had ever been before. Charles strong, muscular stomach rubbed against it with each of his sensual thrusts deep inside my girlie boy vagina! I knew I would sissy-cum soon. I tried to hold it back; I cried out, "Fuck me deeper and faster Charles darling!"

With this he became a primal man responding to his urgent instincts to deposit his seed in his effeminate lover! There was no gentleness now; rather I was being pounded into the mattress with rapid, deep thrusts of his rock-hard cock! The sounds of intercourse filled every nook and cranny of the bedroom: my sissy, high-pitched moans of delight; his guttural manly grunts; flesh slapping against flesh, the bedsprings "singing" that wonderful song of sex!

I squirmed my buttocks on the bed sheets, and I instinctively thrust back at my virile man. Oh, my, oh my, his thrusting penis deep inside me felt so, so good! He cried out, "Oh Wendell, oh fuck baby, that is so hot!" He knocked off my wig and began to rub my bald head as he was obviously approaching orgasm. He cried out, "Oh my hot sissy boy is my transvestite piece of hot, hot ass! Take it pussy boy! Take my cum!! Ahhhhh!"

I could feel his cock pulsate and discharge copious amounts of semen deep inside my anal pussy! I could feel a very effeminate climax deep inside my vaginal anus as my little dick spurted all over Charles' stomach and my tummy! I cried out, "Oh, oh, oh, eeeiii! Oh, fuck yes! I am a boy woman fulfilled!" I held tightly onto Charles; I wanted him atop me and his penis inside of me always!

As Charles came down from his orgasmic high, he remained hard, but still, within my vaginal anus. We hugged and kissed for a few moments, and then he looked directly in my eyes and said, "I love you, sissy baby."

I replied, "Oh Charles, I love you so, too. I guess I always have since we were boys. Do you suppose I became a transvestite because of a secret need to please you?"

"That could be, Wendell honey. Then again, you probably needed to be a male woman in any case, because you are such a vaginal, effeminate sissy boy. And, I mean that as the ultimate compliment, my sweet cross-dressing girlie boy! I love seeing you cross-dressed my sweet boy woman. You turn me on so not because you can 'pass,' which you can't, but you turn me on so because you can't pass, nor should you ever try to pass. You should look like what you are, my dear: a very sexy boy woman in women's clothes and makeup!"

"Oh Charles can I be your 'Wendi' instead of your 'Wendell' when we are along together?

"I'll think that over, little one," he softly replied." I then teased him by clamping my anal muscles on his penis and alternately squeezing and letting go, like really hot women do with their vaginas! As I did this, I whimpered, "Oh please, pretty please!" He breathlessly replied, "Oh baby, you are really good…yes, my Wendi…you are one hot boy cunt!"

I loved being coupled to my manly Charles as we lie quietly kissing, hugging, and having romantic pillow talk. I could feel that my small penis was stuck to his manly stomach because of my dried jizz.

As wonderful as all this was, I realized that my femmie butt was sore from our hot session of intercourse. I whined and complained a bit, "Oh Charles, I want you in me but my sissy butt-pussy is sore."

He placed his finger over my mouth and softly said, "Quiet, little one. That is to be expected. You will grow to accept me with no soreness at all. As we grow together in the coming days and weeks as a couple, honey, your butt-pussy will adjust fully to having my penis where it belongs; where we both want it to be, right my little sex pot?"

"Oh, Charles, I know you are right. I must learn to stop being such a whining girl and act like a grown male woman." The thought of what he had just said was so erotic and romantic. That, with the feeling of his still hard penis quiet inside me caused me to reach down and gently caress his manly balls. He softly moaned and, in turn, he gently fondled my little sissy balls and rubbed my little penis, freeing it from the sticky jizz. He then cupped and gently squeezed my little penis and I could feel him grow harder inside my anal vagina.

Charles began to breathe harder again and, oh my gosh, he started screwing me for a second time. Faster and faster until the sounds of sexual intercourse once again filled the bedroom! I thrust my ass back at him with more finesse than my virginal first attempt at being his transvestite girlfriend! We were truly a sexual team now, man and boy-woman truly and thoroughly coupled and locked together in, by far, the best sexual intercourse that bed had ever seen! (Before it had only been my wife Mary and me!)

This time his hands cupped my buttocks as he repeatedly and rapidly drove his hard penis home deep inside me. The feeling of his strong hands kneading my ass as he gave me the hard, fast dick caused me to once again orgasm from my small penis and deep inside my vaginal anus. I swooned and cried out, "I am so glad we found each other, Charles! I am so glad I love to wear women's clothes and sexy lingerie!"

We again cuddled from our mutual post-orgasmic high. This time Charles oh so magnificent, manly penis grew soft inside me. He whispered in my ear, "After we rest for a bit, sweet satin-panty sissy, we will take a shower together. You will learn how to wash and clean my penis while on your knees then I will instruct you on becoming my very private cocksucker!"

"Oh Charles, yes, darling," I breathlessly replied, "Sucking your cock is another girlish duty I need to perfect!" Once again, I was so excited at the prospect of fulfilling another absolutely exciting and very erotic aspect of my long suppressed femininity!

As I cuddled with my darling Charles, I rubbed my smooth nylon-clad left leg on his manly legs. An impish, quite mischievous thought entered my mind: Wouldn't it be so fitting for both our wives to walk in on us while Charles and I are approaching climax during intercourse!

An hour later found Charles and me taking a very long shower together. He was naked and so commanding. I still wore my silicon bra pads and a sexy one-piece swim suit. Charles pressed me against the wet tile and kneaded my buttocks as he pressed his hard cock against my groin. My little dick was throbbing hard and up flat against my tummy. Soon I was on my knees taking Charles' rigid penis into my cunted sissy boy mouth. I loved it! I squirmed by ass and made little sissy cocksucking sounds as I serviced my sex master's urgent needs. I rubbed my little dick through my swimsuit as I serviced my darling. The thought suddenly entered my highly aroused mind of my Mary, naked, on her knees, eagerly eating a naked Jennifer's moist vagina. I pulled my throbbing hard little dick out the pant leg of my swimsuit and began to beat off really fast thinking of my wife eating Charles' hot wife's moist pussy. With that I shot my sissy load onto the shower floor! Within seconds Charles' cock erupted inside my cunted mouth. I eagerly swallowed his manseed!

 

Epilogue

Today neither Charles' wife or mine, nor our circle of friends, suspect that Charles and I have bonded our lifelong friendship by becoming homosexual lovers. No one knows that I am always underdressed in satin panties, open cup satin bra, waist chincher, and sheer nylon stockings whenever Charles and I are together in public.

Mary realizes I can no longer obtain an erection when in bed with her, but this doesn't seem to bother her much at all. (I have woken up several times late at night and have seen her finger fucking herself as she quietly says, "Oh Jennie, oh my Jennie.") Charles is so virile and manly he has intercourse with Jennie just often enough to keep her satisfied.

I have taken to enjoying doggy style intercourse with Charles immensely. I love it when he jacks me off during doggy style intercourse and tells me that my little dick will never enter a woman again! Feeling his strong, masterful, loving hand stroking and gently squeezing my little dick feels so much better than any woman's vagina can on such a small dick.

  

  

  

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