tagTranssexuals & CrossdressersOne Mad Night Ch. 1

One Mad Night Ch. 1


I'd experienced a great many crazy perverted things in my sexual adventures, but this was a new one on me. The sort of thing you read about, or hear about, or lied about, or just saw on porno videos. Whether it was actually a fantasy, fetish, or obsession was always down to you. But there I was, lying in bed, my hand exploring on my "female" partner's body exactly what hers was on mine. The night had been wonderful up until now, and now it could go in any direction. She was pretty, with a fantastic physique, I mean I like to keep the fat off and the heart and muscles strong but she was in great shape. We'd been talking, bullshitting, and flirting for the last few hours in a seedy downtown bar. I'd actually gone for a quiet beer to be alone with my thoughts, not to pick up any action. I don't know what she was there for.

You see, I'd been an active bisexual for a number of years, but then, almost a year ago to the day, I'd freaked out and decided to go straight. It was good, girls had what it took to satisfy me, and I'd had a short relationship and a couple of flings. Was it what I wanted? I didn't know. Fact was, a girl I'd had a fling with had walked back into my life and we were both talking about why we didn't go steady. We'd had a couple of dates, fucked, and had a big "for real" decider date in a weeks' time. But just 2 nights ago, a guy I knew was gay had come on to me after drinking one too many beers together over at his pad on a Saturday night. He blew me and was fucking good, but it didn't work. I felt actually straight now. No matter how hard I was from his ministrations, or how bad I wanted to return the favour, I just didn't want to do that anymore.

And I'd come to this bar to drink myself stupid and think really seriously about who I was and what I wanted. Because the girl in question was worth it. But on the way to getting drunk. Cristy had helped me. And I'd helped her. We drank, we bullshitted, we flirted. The only girl's I'd met before as forward as her were of two types, the kind that want to get paid, and the kind that are in the same swingers' club as you. But this was just a bar, I was just a guy, she was just a girl.

Curse her apartment for being so close by.

She had a tongue like a preying anaconda, hands and arms like tentacles … when she held me and kissed me I felt woefully inadequate on the return. I remember telling her the story about the girl and the guy without making my past make me sound like too much of a freak. I can't remember what she'd said to me back.

We hadn't wasted more than a single beer and the most basic niceties on the sofa before she'd pulled me into the bedroom, and her silky hands were into my flies and deep into my crotch before I could help it. She had my pants off and on the floor in double time, and I pulled her skirt away down to her bright pink panties as we rolled and kissed. She bit my ears and scratched my back and scrabbled at all my remaining items of clothing until at last I was in my bare boxers, 6 ½" standing proud through the convenience slit, and I had her top off so that just her bra and panties covered her body.

It was as I massaged her buttocks and her clit that I discovered I had a handful of nuts and the base of something far more phallic than any clitoris! I was no stranger to a man's physique and even come acropper with a transvestite at one point, but here I was, being eaten alive by a real transsexual! Shemale, He-Girl, Chick with Dick, whatever you want to call it, she was either once a boy, now a girl, or vice versa, either way not quite there. She was packing a bigger gun than me, nearly 7 ½", I couldn't believe it! She caught my eye as I held her womanhood, slowly massaging it through the material of her pink panties, ever as her fingers gently toyed with my nuts. We lay there in our underwear, playing with each other, and I tried and failed to get across my point that I was juggling with the longterm effects of being this kind of person sexually. We kissed and touched and she told me she wanted me, she wanted me to do it to her, she needed it so badly. It didn't mean I wasn't straight and didn't matter anyway that I was attracted to who I made love to and didn't lose sight of the girl I liked no matter what I did.

Whether or not it made moral or sexual or common sense all became irrelevant as she took me into her mouth and sucked hard on my head. She had slunk down my body without warning, at a part of the conversation that really should have gone on. But all I could do was groan in pleasure and accept my fate as her electric fingertips did something incredible to one nipple and my ballsac as her soft wet tongue licked heavily around my pubic area and ultimately up my shaft slowly but surely to engulf me. There, she sucked, hard, slow, and with an intensity I myself knew all about … the intensity with which you suck off a lover, not to help them finish, but to make them so hard as that they will do anything you ask of them to finally end in climax. The intensity that instead of bringing a swift and satisfying orgasm, brought on a desire to fuck like a rabbit in heat.

The kind of oral skills that bring all sorts of trouble and all sorts of pleasure. She was fucking good, and she was going for gold. My whole body jerked and I almost climaxed on the spot as her tongue pressed into my cock hole, and a well lubricated finger was pushed knuckle deep into my ass. The sanctity of my ass was one of those difficult decisions I'd had to make about being straight, previously a common and exhilarating source of physical pleasure, no lover had invaded my asshole in over a year, and it was a surprise. A painful and exhilarating surprise that I found myself unable to protest.

As she pushed her finger hard into me, finding places that I had decided off limits so long ago, I discovered she had another skill, as she took my whole length into her mouth, my God, she "deep throated" me effortlessly, time and again. Working teeth and tongue on my head and rim the one minute, licking up and down my shaft and teasing my balls the next, then, without warning my pubes were at her nose and my tortured end deep within her oesophagus. Fucking incredible. I amazed myself by not coming, possibly the alien but welcome returned feeling of her finger(s) probing inside me helped give me an additional focus and I held steady.

I lost track of time, but soon we were kissing hard again and I could taste my own precum on her tongue. She played with my balls and inner thighs and stuck her tongue in my ear and told me she wanted me to fuck her. Oh she needed to be fucked, please, baby, fuck me in the ass, fuck me.

I applied Vaseline generously to my member even as she did her asshole, on her hands and knees in front of me. She squealed slightly as I pushed a finger against her tiny pink hole, and she beat off her own cock feverishly. I tried not to think about what a magnificent size she had, what an awesome and beautiful hardness. I gripped her buttocks hard and got into a good position. I released one ass cheek to use the hand to guide myself in. Oh God, fuck me baby, she moaned. With a grunt and a push I entered her, forcing my head against her puckered sphincter. It didn't put up much of a fight, and I pushed past an initial sandpaper resistence with the Vaseline helping us slide together. I'm aware that I moaned significantly as my head became part of her, swallowed by her sphinctal reaction, and she squealed in pain and pleasure, my God, I'd forgotten how good anal penetration could feel … and how it was so much better for her, on the receiving end. I felt so alive.

Slow and hard I forced my way into her and she began to scream and moan all sorts of unprintables, passionately working her own cock hard and raw, bringing herself to the edge as I pushed in. Her ass was beautiful, hotter than Hades, tight, but far from inexperienced, and I felt no remorse and heard no cry for mercy as I began a rhythm, pumping hard, pushing her face into the bed and lifting myself so that I could push down as well as in.

The hand not pleasuring herself suddenly finding its way to my testicles and her pinching and fiddling them gently told me that I was giving her what she wanted. She wanted a good hard fuck, she wanted to be fucked hard in the ass, and I gave her my greased up length to the hilt, slow or hard, fast or deep, I went solely by her cries. These alone told me what my shaft could do for her.

What she was doing to my shaft was something different indeed, what with her cries of yes and fuck me and everything else, what with her fingers playing with my nuts, and what with her fine butt cheeks in my hands, and what with her awesome rectal passage clinging so hard and hot to my intrusive member, I could not hold back. I fucked her as hard and for as long as I could, but for sure I came before I could bring her to climax, and with that sudden feeling I knew was the point of no return I pulled her hard back to me, pushing in as deep as I could, and with her butt crack wide open, cheeks to my hips, and asshole almost gripping my pubic hair I had a most wonderful orgasm, and my cock opened up, feeding a veritable wave of white hot cum deep, deep inside her, plastering her internal organs in wet sticky love. I felt my body jerk and my cock jet several times, and I didn't, couldn't let her go as I filled her ass with an awesome volume of pure liquid lust and desire. It felt so sticky and hot and wet and wonderful as my juices flowed within her, my own cock shrinking in its own spew in that awesome spunky place.

Finally I withdrew, exhausted, disgusted, excited, confused, but most of all spent, and I collapsed onto my back on the soft welcoming bed. She leapt on top of me and I could feel the heat emanating wetly from her ass. She ran her fingers through my hair and stared into my eyes, it was an incredibly defining moment for me, for as natural as it would otherwise feel, the moment was dominated by her 7 ½" member, which bounced on my neck and chin. At last she fed it into my mouth, and flung her head back in pleasure as it passed my lips.

I had not felt the sensation or tasted the musky taste of a warm, wet phallus in my mouth for an awful long time, and it was as welcome as it was alien. I didn't beat myself up with crazy thoughts of what I had been missing and instead took pleasure in that massive thing suddenly and awesomely between my lips.

God how I enjoyed the moment … probably made more easy by the feminine sighs of pleasure she uttered feeling the welcoming warmth of my mouth rather than the guttural animal grunts a male lover would made. As such, the cock, never unenjoyable, did not feel at all "gay", and I sucked longingly and lustfully on its damp stiffness. Her fingers roughly made fists with my hair as she gyrated atop my chest, and I held an ample buttock with one hand, a full breast in the other as I licked up and down her shaft, kissed the sweaty flesh, suckled on the head and lapped up her precum. She held my ears and fucked my mouth as her sighs got shorter and faster, she began panting, and breathing oh yea, oh yea baby, do it.

An instant was all it took, without warning my senses overloaded with the sudden tart explosion of flavour and sensation as she flooded my mouth with a mighty yell. I was both shocked and delighted as she reached climax and her cock jerked, spitting a hot blast of thick and salty cum all over my tongue and into the back of my throat. She held my head tight, giving me no escape as her orgasm flowed hard and true. I was excited, exhilarated, ecstatic all at the same time, then a mere instant later I felt depraved, diabolic, disgusted as her pale white love filled my mouth, warmly overflowing, and I found myself half swallowing and half dribbling the wonderful stuff out past my lips and down my chin like a base and filthy slut as she fired again and again, feeding me a load any full blooded male would be envious of.

At last we came apart, both spent and softening, and I licked my lips and gulped embarrassedly before crawling up the bed to lie beside her. She ruffled my hair and kissed me lightly on the lips, breathing sweet thank yous and that was incredible, your beautiful baby, do you like my cock, you know how to fuck an ass God my world moved and other meaningless nothings. At length we kissed and drifted, half hard into sleep, fitful and filled with crazy dreams for me, probably conquest and triumph for her. What did fucking a shemale and liking it mean about me, what did my pleasure in sucking her cock mean, and I surprised myself with my awesome cum-lust. What did it all mean … could mere women ever be enough again?

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