At 18, I was a quietly effeminate young guy; people tended to think me shy rather than gay. I lived in a hostel in South London, a place full of transients. JJ was 44, a builder just returned from half a lifetime in Australia.

You couldn't get more transient than JJ...

During meals, he always sat near me and told tall tales that made me smile. And whenever I went out at night, he insisted on accompanying me as far as the nearest tube station.

On the way, he would always make some lame excuse to pat my ass, which made me blush, because under my jeans I wore soft, silky women's panties. I got a tremendous thrill just feeling them against my skin, but whenever JJ's fingers touched my ass, the thrill got even better!

And for a couple of weeks, that's all that happened. JJ flirted with me, but nothing more. Then one night he invited me out for a drink. I went along and got fairly drunk at his expense, listening the whole while to his sob story of the acrimonious divorce that made him decide to quit Australia.

The way JJ told it, he was so straight he could have been a six feet plumb line! It got me confused; I began to wonder whether his tactile interest in my ass was really just in my imagination?

Back at the hostel, he invited me to his room for a coffee. The rooms had no wall sockets, so to plug a kettle in, JJ had to first remove the light bulb.

Sitting side by side on his bed in the dark, waiting for the kettle to boil, I felt his hand rest firmly on my thigh.

"I'm not gay," he explained, "but I want you to masturbate for me!"

Conflicting thoughts began to spin round in my head, almost making me dizzy. If he wasn't gay, why did he want me to masturbate? And would I dare tell him I really wanted to be a girl?

It was all too much for me! I stuttered out some lame excuses and fled to my room. But I just couldn't sleep; all night long I tossed and turned thinking about JJ, who was classically tall, dark and handsome, and fretting whether I'd blown a great opportunity.

Eventually, after several sleepless hours, I wrote him a note and slipped it under his door...

Dear JJ,

I ran away because you confused me! I couldn't figure out whether you are gay or not? But then I thought maybe you are NOT gay, but are attracted to me as a woman, which would make perfect sense, because most of the time I WANT to be a woman! But I am very confused! You asked me to masturbate, and right after I do that, I get guilty feelings and that's the one time I DON'T want to be a woman! Which is why I ran away! If you think you can help me PLEASE do, otherwise just forget about it and burn this note!

C.

I never saw JJ at breakfast because, being a builder, he got up much earlier than me. But at the evening meal, he had a peculiar smile on his face and was friendlier than ever.

"Thanks for your note!" he said, "I think I can help you. Come up to my room later."

Obediently after supper I went to his room. "I've done a little shopping," he explained, "and these things are for you." He handed me a soft package, which I opened on his bed. Inside was a skimpy black bra with matching panties, a pair of black, seamed hold-up stockings and a translucent pink negligee.

"Try them on for me, CAROL," he said, and I blushed to hear my femme name because, even though I'd always identified as Carol, no man had ever before called me by it.

Quaking with nerves and trepidation, I took off my male clothing and stood sheepishly before JJ, naked except for the pretty red panties I was wearing. With a knowing smile, he came up close and rubbed my boy-bits inside the silky panties, causing my tiny cock to grow as big as it was able.

"Hmm!" he whispered, "You really are a girly little sissy, aren't you?! It's almost a pity to make you take those cute panties off! But I really want to see you in the stuff I bought, so off they must come!"

Obediently, I took off my panties and put on the stuff he'd bought, starting with the lacy black bra, which JJ helped me fasten. Then I put on the matching panties and the seamed stockings, while JJ ran his hands up and down my nylon clad thighs, his fingers lingering a long while around my crotch.

"Your legs are so very smooth and feminine," he complimented, "you have waxed them nicely, just like every good little girl should!"

I blushed, too tongue-tied to tell him that I'd never grown any body hair. Indeed, I only needed to shave my face once a week.

Sitting on the bed, he commanded me to come to him, and I sat nervously on his knee, an arm awkwardly round his neck while he gently caressed my nipples through the skimpy bra.

"I told you I'm not gay," he explained, "but my bitch of a wife has cleaned me out, and now I want something different! So I'm going to teach you to be more of a woman than any woman I've ever been with! Would you like that?"

"Oh, yes!" I exclaimed.

"Good girl! You look absolutely stunning! Let me take some pictures."

So saying, he took out a camera and took some photos of me, sitting nervously on the edge of his bed in lacy black lingerie and a translucent pink negligee.

"The first thing we need to do," he explained with a wide grin, "is get you past this awful guilt you experience after you masturbate. So here's what we'll do; you're going to masturbate for me right now, then you're going to stay dressed just as you are and spend the night in this room, doing everything I demand of you, just like the good little hooker I know you yearn to become!"

"I d-don't think I c-could!" I stammered.

"Well, if you don't then these photos are going to get seen by everyone in this hostel, to say nothing of your employer and your parents!"

"Oh, n-no!" I cried, "You wouldn't dare!"

"Just try me! But remember Carol, this is for your own good! Now lie back on the bed and masturbate!"

I did as he'd ordered, stroking my modest boy-bits as well as I could manage with trembling fingers. As I jerked off he took some more pictures, telling me these were the ones that would greet my boss first thing in the morning unless I played ball.

Although I hated JJ for what he was doing to me just then, I was strangely aroused nevertheless. But this didn't surprise me; I'd often fantasized about being humiliated and forced to submit to the whims of a powerful guy, and JJ was ticking all those boxes.

Still I knew that, once my wank was over, I'd immediately be overwhelmed by guilt and repulsed by the sexy women's clothing I was wearing. I'd be desperate to get back into my daywear so I could kid myself I was a regular, heterosexual guy for the half hour or so before my feminine feelings came flooding back.

I'd lived with this paradox since puberty and it had prevented me from having any kind of sexual relationship, either with a man or a woman.

In no time at all, my modest little cock began spurting cum onto my belly and my desires went into reverse gear. I urgently wanted to be a man again.

But JJ was firm...

"Good girl! Now I'm going to teach you how to suck cock properly. So get down on your knees!"

It was against every instinct. Just then, I wanted to be Carl not Carol; to throw off the women's clothes and ape a regular dude. But JJ was having none of it.

"I said down on your knees, sissy!" he commanded, and through fear of the consequences

should I disobey and particularly from the thought of what my boss would do if he ever saw photos of me dressed as a slut and jerking off, I did as JJ commanded, and soon found him standing upright with his bulging crotch pressed tightly into my quivering face.

He unzipped, revealing a throbbing manhood that dwarfed my paltry appendage. Before my eyes lay eight solid inches of thick, pulsating meat, streaked with bulging veins. So this was what a woman expected to see when a real man dropped his trousers? Immediately I realized I was altogether something else.

The realization brought my feminine feelings back much sooner than I would have thought possible, and I began to feel glad of the ordeal JJ was putting me through. Tentatively, I took his throbbing cherry in my mouth and began to suck.

"Not bad for a beginner, sissy, but use your tongue more and blow a little!" he barked.

I did as my master had commanded, and began to roll my tongue around, grateful to feel his cherry pressing back in appreciation and to hear his gentle groans. Placing his hands on the back of my head, he forced me down onto his full length, and I felt for the first time the hot trickle of pre-cum dripping down my throat.

Having nothing for comparison besides my own swift and rather pathetic wanks, I anticipated an early explosion of warm, salty cum into the back of my throat. But JJ had other ideas! He was a real man with self control and plenty of experience. The pre-cum was all I would taste of him that first night; instead, he pulled out and ordered me to stand up and bend over the bed.

I did just as he demanded, spreading my quivering legs as far apart as possible at his further instruction. Then he gently stroked the back of my nylon clad thighs till my butt cheeks quivered like jelly, when I suddenly felt a cold, greasy finger rimming my boy-pussy.

"Just a bit of lube," he explained, "nothing to worry your pretty little head over!"

An instant later and he was inside of me. At the first thrust I gasped and let out a little squeal. Knowing it wouldn't be the last, I buried my face deep in a pillow to smother my groans as he thrust his powerful ramrod up and down inside my tight little hole while my every sinew shuddered violently.

"This should cure you of your guilt!" he sneered. "Your name is Carol and you're a girly sissy, and if ever you forget it, just remember what happened tonight!"

So saying, he thrust harder than ever and, grabbing my hair and pulling me even closer, exploded a full load inside me till his copious warm cum filled every inner crevice of my aching boy-pussy.

It was the first of many nights I spent in JJ's room; indeed, I didn't once sleep in my own bed till he left the hostel for another job in another town, some three weeks later.

Every night after supper, I'd dress for him then masturbate while he told me how he boasted to his workmates of the fun he was having with a dirty slut called Carol. It turned me on like there was no tomorrow, and I could hardly wait to finish my wank so I could set about the business of satisfying JJ as his girl.

We did it every which way he could think of, and by the time he left, my boy-pussy had grown lips and was so slack it could comfortably take a fist.

Above all, for the first time in my life I was happy just being me! I'm a cock loving, girly sissy, and I'm proud of it. And just as I've never needed to remember that night to know what I am, so I've never once forgotten it.

And nor have I ever forgotten JJ!
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Pub: 19 Mar 2021 00:52 UTC
Views: 70