Written by Suzi_sheffield

9 May 2007

Karen the transvestite make-up salesgirl had, I imagined, been employed by my wife Tina both to complete the feminisation of my appearance when dressed, and to humiliate me by seducing me, leading me into my first sexual experience with another man, albeit a gorgeous, sexy man dressed in an immaculate mini-skirted woman’s business suit. After Karen kissed me so sensuously on my newly lipsticked lips for the first time my body was in turmoil.

After so long as a sexually-denied wanker, whose wife had even found ways to reduce my solo spunking sessions to about one a fortnight, I was desperate for real sex with another ‘woman’. Part of me desperately wanted Karen to touch me again, but another part of me was horrified at the thought. It wasn’t just that I had never (despite my finding emotional refuge in wearing knickers, nylons, and suspenders) considered myself to be at all gay, it was also the shame of allowing myself to be intimately kissed and touched by a sissified, effeminate man in front of Tina, my wife.

Little did I suspect that virtually none of the events of the last several months had in fact been my wife’s idea. In a week’s time I would be given the truth by the man who had months ago become, unknown to me, my wife’s master. He had seduced Tina, and come to completely dominate her life, to the point of ordering her to find ways to stop me even daring to ask her for sex, and then to exploit my weaknesses to prepare me to become, like my wife, his slave. In many ways I had already submitted to him, without even realising it, in that I submitted to his degradation of me through Tina. Karen was Master’s latest idea. She was a previous conquest of his. Karen’s wife too had been seduced, dominated and controlled by this wilful, masculine man, allowing and assisting Master to gradually feminise her husband, and eventually change ‘her’ name to Karen.

Karen resolved my conflicting desires to be kissed and to be left alone by demonstrating more of her wares. My birthday treat continued with the beautiful transvestite doing my nails for me, filing them smooth and painting them in a very girly shade of pink to match my new frilly, ruffled panties. While we all waited for my fingernails to dry, Karen told me how attractive they looked, and then gently kissed my fingers, one by one. I didn’t resist. I didn’t want to.

After that she even washed my feet and did my toenails to match my fingernails. Everything she did, she did with feminine grace and tenderness, chatting to me as she cosseted me, wrapping me in a warm, caring cocoon of girly affection. After a while I found myself relaxing and enjoying her attentions. Karen could see she was beginning to win me over, and this made her bolder. Master had given her several very specific lesser targets for today, and one major one. Tina’s job was to witness how many of Master’s targets she would achieve with me. I was later told that Master had been very pleased with Karen: she had achieved every task he had set for her.

Karen’s next task was to get rid of all my nasty man-hair. My nylons were unclipped from their suspenders, and gently pulled down. Depilatory cream was applied to my thighs and calves. After about five minutes Karen used a plastic spatula on me, removing the cream and, I soon saw, all the hair from my legs with it (another of Master’s targets had been met). This did momentarily panic me a bit (what would people think if they saw my smooth legs?), but the realisation that I would be able to experience the feel of nylon stockings on my now soft and velvety legs soon made me feel better. My fore-arms followed. When it came to my under-arms Karen switched to a lady-shaving system, explaining that “Everyone’s different, and you have to find the best system for you, so we’ll try both shaving and cream today, to see which irritates your skin less”.

I don’t know how long Karen spent preparing me to look like a woman, but it must have been at least ninety minutes. Foundation, blusher, eye-shadow and eye-liner, mascara were all applied. Perfume was sprayed on me. Finally I was even given a blonde wig to wear.

After so much effort on her part, I felt I couldn’t turn Karen away the next time she touched her lips to mine. When she showed me my new self in a mirror, and told me I was beautiful, I could feel myself melting. I wanted something new, something exciting. I knew that if I was offered a relationship now with a ‘girl’ like me I would find it hard to resist. I would need to be led, to be shown what to do, but I knew I was ready to respond.

Karen knew it too. She was about to make sure that all her hard work came to fruition. She raised my hands to her lips and kissed them, then gently drew me to her and kissed me again. Now I wanted her lips, and kissed her back hungrily. When she thrust her probing tongue into my receptive mouth it seemed the most natural thing in the world, and I french-kissed her back.

This was not just like kissing a woman thought; it was better. I realised, even as my lips were flooded with sensation, that I could feel Karen’s cock expanding against my leg, under her skirt. This was the moment of truth for me, I knew. Would this shock of sensing another man’s cock growing with lust for me stun me, force me back to my old reality when even the thought of such a thing would have horrified me? A wave of relief swept through me as I realised that wasn’t happening. I was enjoying feeling Karen’s cock through out skirts, and I wanted to rub my ‘cockette’ against hers.

My wife watched us – two sissy, effeminate perverts touching each other up. I knew she must have wanted this to happen, but in any case I was beyond caring about what my cold, uncaring wife thought. I only wanted Karen now; she was conquering me.

Over the next half hour of blissful love-making our skirts and tops were removed. We fondled each other’s bras, ran our fingers down our lover’s tingling thighs, and kissed gently, roughly, passionately, imploringly.

Eventually Karen stroked my balls through my panties and I was in heaven. Seeing my reaction she cupped by ball sac in her hand, and manipulated me, twisting and squeezing my smooth, hairless, balls ever so slightly, then rubbing my balls first against my body, then against hers.

Our cocks touched through our knickers and I thought I might cum then and there, but didn’t want too, not yet. I wanted it to go on and on. But Karen had Master’s major target for the day to meet, and now she was able to move in for the kill. It was just a strange whim of his, but my wife was there to see it happen, and report back on my seductress’s efficiency. Karen pulled down my knickers, exposing a hard cock, rampant despite the constricting gold wedding ring behind its purple head. Then she exposed her own magnificent weapon. From somewhere she produced a condom, and unrolled it over her penis, before taking my hand, and placing it on her rubberised cock. This still felt new and strange to me, but Karen indicated that I should wank her, so I did.

I found I was enjoying wanking Karen’s cock. It was big and firm. The movements were sort of in reverse compared to when I wanked myself, as I was facing her, but I wanted to please my lover. She had a foreskin, which I liked. I masturbated her as lovingly as I could, trying to keep my hand around her knob and shaft as effectively as possible. It would have been easier without the condom, but I was loving every minute now, and almost didn’t notice when she was going to cum. Karen groaned and almost screamed something incomprehensible.

I looked at her knob head, and saw the first creamy white spurt of lovely spunk jet into the teat of her condom. I had done that, I was making her cum! I held her cock tightly and another pulse of ejaculation filled her rubber, and then two more. I was transfixed. I squeezed her gorgeous cock, and a fifth and final thick string of spunk shot from her, making quite a pool of liquid stretching the end of her condom. I wondered whether I should fall to my knees, rip the condom off Karen, and suck her into my grateful mouth, but after a brief rest Karen indicated something else.

My transvestite lover reached down to her own cock, and carefully removed her condom. Then she grasped my penis, and began to slide the slippery, used, spunk-lined latex over my own expanded knob head. The sensation was out of this world. Karen’s thick, sticky cum lubricated my knob, and her used condom slid easily over me. I knew I would spurt uncontrollably at any moment, mixing my cum with hers, joining us together. If she wanked me now I would ejaculate on touch.

Karen didn’t wank me though, but held me to her and, looking into my eyes, kissed me slowly and sensuously, sliding her lipstick against mine. That was it. I came as she held me, staring in ecstasy into her eyes as I exploded helplessly, my rubberised cock covered in her cum and rubbing against Karen’s now semi-soft penis. Spunk leapt from my balls, again and again, mixing my sperm with hers. I came for Karen, and almost cried with relief and joy and sheer sexual ecstasy. I had found someone like me, and we had come together.

To be continued in Part Seven.