My First Trans Woman

(Author's note: The following is a short but true story from the mid-2010s. I'm posting here as an initial attempt at self-published erotica, while I work on a longer and more significant story series. Feedback would be welcome.)

****

My personal journey from "straight-only-or-you're-a-poof" to "let's-see-where-this-could-lead" sexuality had only been going for a few years. My non-straight-cis experienced was limited to some voyeurism, stroking a dude's cock, and having mine sucked in adult cinemas and gay saunas. One time, in a glory hole, I'd learned such facilities can be used for more than oral, when a bloke backed himself onto me. The richer warmth of his rectum as it had enfolded my condom-clad member had been the giveaway. It had been outside my boundaries at the time, and I'd pulled back sharply, ignored his frustrated grunt, and peeled the rubber off me as quickly as possible before fleeing.

But now, as I parked on the street outside the apartment building, my heartrate quickening, I realised I was about to take a fairly big leap.

"Do you include French kissing?" I'd asked on the phone an hour earlier when the Thai trans escort had called to confirm my booking.

"Ooh, darlink. I love kissing," she'd purred. Her voice was rich and throaty but not as deep as I'd expected.

"And...and sucking?"

"Oh yes, I suck very good," she'd assured me.

"No...I mean yes, but..."

Her voice lowered in pitch and the slight rumble caused a sympathetic buzzing in my groin. "You can suck my cock too, darlink. It very clean and feel very good."

I'd explained that I'd never been with a transgender woman before and she assured me I would have a good time. Now I was texting her again with slightly trembling fingers to let her know I'd arrived. One minute after that, I found myself at the slightly open door to her apartment, hearing her voice calling me to come in and close it behind me.

I did so, stepping into a neat and surprisingly well-lit abode. On the other side of the room, she was standing, a touch taller than I'd imagined but otherwise looking just like the photos on her ad. Her form was lean and athletic and, as she began to stride towards me, her long gown parted so that I caught bare glimpses of what had only been hinted under the sheer gauze - her black satin bra and panties, her stockings and suspenders, and significant expanse of flawless bronze skin.

I swallowed once, then returned her sultry greeting with a slightly shaky one of my own and, by the time I was done, she'd crossed the room and was crossing her wrists behind my neck.

The kiss came so quickly and naturally, and she was so pretty even close up, that I didn't hesitate. Ignoring the small voice that was trying to remind me I hadn't yet paid her, I returned her embrace, our tongues seeking each other out, swirling, sliding around in and out of each other's mouths. She was gasping slightly and moaning, and the feeling of her warm breath mixing with mine made me a little heady, as well as sending a tingle into my stiffening cock.

I allowed my hands to slide lower from her waist, under the band of her black satin panties and, as I gently kneaded her arse cheeks, she groaned louder and began to press her pelvis forward. I could feel her hardness and, as it rubbed against mine through my pants, felt myself swell even more.

Eventually, my conscience won out and I broke the kiss first. She gave a little cry of frustration and pouted as though I'd robbed her of something she'd been craving. Reaching into my shirt pocket I gave her an apologetic smile.

"I need to give you some cash?"

Her pout dissolved into a warm smile. "You are good man. Nice man. Have shower and I get ready."

She took the cash, then guided me to the bathroom where I quickly stripped and gave myself a swift but thorough wash. I dried myself on a fresh, clean towel and made my way to the bedroom she'd indicated. This room was dimmer, its blinds drawn and only a lamp placed on the floor on the far side of the queen sized bed, illuminated the small space.

In the middle of the bed, she was stretched out; her gown, suspenders and bra gone. She was toying slowly with her breasts which were modestly sized but had the slightly inflated aspect of the augmented and were topped with prominent brown nipples. She flicked one and gave a small gasp, then smiled knowingly and patted the bed in front of her.

"Lie here, nice man," she crooned.

My cock was still partly erect from our initial kiss and, as I moved onto the bed, she wrapped her slender fingers around it, almost as if she was using it as a handle to steer me into the position she wanted. It began to swell in her gentle touch and I gave a soft moan at the pleasurable sensation.

"Mmm...you have nice big cock," she murmured as I settled in, lying on my right side and facing her. She pulled on it gently and I took the hint, sliding myself closer until I was close enough for her to release me and I could feel the satin of her panties press against my shaft. She reached over my hip with her left hand and pulled herself closer and began gyrating her groin against me as her lips sought mine out again and before long we were making out, clutching each other's arses and enjoying a warm, tingling frot that was only separated by the black satin of her panties.

"God...you feel so good," I moaned as I licked and nibbled her throat. She reached between us and pulled her panties down far enough to release her member and then used her long fingers to enclose it, along with mine, in the one grip.

"You big man cock feel amazing," she moaned as she jerked us simultaneously. She'd added lube to her hand and the slippery feeling of her fingers wrapped around the outside of my shaft, and her thinner cock gliding up and down the underside of mine, sent a wave of pleasure through me.

As incredible as the sensations were, though, there was a boundary I needed to cross. I licked and kissed my way down her chest, taking each of her nipples into my mouth and using my tongue to swirl around her already stiff nipples. But this wasn't the kind of flesh I was really craving, and I slid lower.

Her right hand had now released our cocks and joined her left, slowly and gently rubbing all over my scalp as she pushed my face down towards her groin. It was clear she wanted this too and when I reached my target but bypassed it, licking instead across and down the prominent bulge of her hip bone, she whined in frustration.

Scooting down until I was kneeling between her spread thighs, I took my first really good look at her package. Unlike a lot of Thai men and ladyboys, I would discover later, she was circumcised, and her modest member curved slightly upwards, her cockhead a little larger than expected for the size of her shaft. In her excitement, her ball sack had become tight and smooth and it's hairless skin shone with the lube that had oozed its way down there.

I carefully wrapped my fingers around her cock, holding it at the base, then leaned forward, my tongue extended, until I was softly and slowly bathing her small nut sack with broad licks. The taste was mostly that of the lube, a slight chemical flavour with a hint of strawberry. I allowed my tongue to travel higher, up along the underside of her cock until I was swirling it around her frenulum. Her whine became another groan and, as I slowly began to lower my mouth over her cockhead, she gripped my head harder and began gyrating her hips in a sensuous motion.

Small though her cock was, it still filled my mouth more than adequately and I felt a shudder of pleasure as I drew it deeper, as close to my gullet as I could get without gagging. I would learn more control later, and better technique, but right now, this first time, I was sucking cock and loving it.

I played with her balls and sucked her rock-hard dick in and out of my mouth for several more minutes. Her moans became more frantic and her hip-twisting more frenetic and I wondered if she was preparing to cum. It occurred to me that, among the boundaries I'd mentally prepared, the question of taking someone else's cock juice into my mouth hadn't factored into my thinking.

Before I could come to a decision, however, I felt her using her grip on my head to pull me away from her penis, and I released her. The cock made a slight slurping sound as it exited my mouth, before standing proud and tall, although swaying a little, in all its saliva-shiny, swollen purple glory.

"Sixty-nine!" she declared, reaching down and grasping my shoulders, pulling me up the bed. I followed her guidance and soon found myself on my back, her knees either side of my shoulders, her tight boyish arse centimetres above my face and my own achingly hard cock being drawn into the warm wetness of her mouth and throat.

I'd expected her arse to smell a little but was pleasantly surprised that only the familiar odour of strawberry lube reached my nostrils. Her butt was toned and tight and I enjoyed a moment of running my hands all over it, squeezing and kneading the bronzed globes. She'd pressed her public bone into my sternum and her cock was pressed into my chest, so it was clear she didn't expect me to return the fellatio in our 69, but her next command made it clear what she was hoping for.

"Lick me, darlink!" she moaned, in between fluttering licks of my cockhead.

Oh well, I thought. What's one more boundary?

I extended my tongue and tentatively ran it up between her arse cheeks and onto the small crinkling flesh of her butt hole. She moaned a little, so I licked a little faster, which made her moan again and soon I was swirling my tongue around that hole like it was a girl's clit. Other than the lube flavour, it tasted of nothing. But it was sensitive, and even a small amount of attention seemed to drive her wild.

Her mouth and throat were working overtime on my cock and, as I stiffened my tongue and pushed the tip into her arse, she gave a long, low guttural groan. I felt every vibration of it and a warm glow began to light up my balls and tingle its way up the shaft of my member.

I was groaning too, now and she must have sensed I was close to cumming, so she lifted herself off me, then swivelled around and began French kissing me again as she slowly toyed with my balls. Apart from being highly erotic, the kiss was reassuring, in that the tongue she was now sucking had just been embedded in her anal chute and I reasoned she must have cleaned in there pretty well, if she was now willing to taste it.

After a moment, which gave us both an opportunity to cool down from the edge, she slid a condom onto my cock and added some more lube to her butt. She straddled me again, this time facing me, then reached behind her. After a little fiddling I felt her sit her weight down and, just as it seemed my hard cock might bend too far, I felt it being swallowed, headfirst by her arse. The sensation was warm and close, like someone had wrapped my penis in a heated blanket and was turning it up to seven. She kept going until I felt her tight arse cheeks nestling against my hips and the groan she gave was her longest and deepest yet.

"Oooohhh....nice man...big cock..."

Her eyes were closed and her fingernails were digging lightly into my chest, as she rose slowly, allowing my member to withdraw about halfway, them slamming herself back down. The impact sent am almost painful jolt though my balls and I placed my hands under her arse cheeks. With me taking a little of her weight, she seemed able to hump up and down on me with greater vigour and I felt my cock begin to glow again with pleasure. The tingle that was building in my balls began to shoot up along my shaft and into my cockhead; not enough yet for me to cum but getting close.

Meanwhile, her cock bounced up and down in what looked like a rather uncomfortable violent nodding. I reached out and took it in my hand but she paused, shook her head, and gestured to the lube. I took the hint and soon she was riding me as hard as before, but this time using the same gyrating motion of her hips to fuck her cock in and out of my doubled fists.

"You want me cum?" she gasped the question after a few minutes.

Taking semen in my mouth was outside my boundaries and I nearly said no, but the sight of her purple cock head appearing from and disappearing into my fists made me reconsider.

"Spray me with your hot load, baby!" I told her and, with a few more frenetic thrusts and a long soft wail, she sent thin ropes of cum up my chest and one particularly powerful jet onto my chin.

She leaned forward and I felt my cock released from the clutches of her rectum, at the same time as she used her tongue to scoop up much of the juice she'd decorated me with. When she kissed me, the slightly bitter taste made me realise I was taking her cum in my mouth after all, and decided I didn't mind.

We made out for a while longer. She'd stripped the rubber off me and wiped my cock clean then re-lubed it and began giving me a tortuous hand job. She nestled in beside me and, in between bouts of passionate French kissing, whispered a heady mix of affection and filth into my ear.

"You such nice man, so considerate...you like my hand wanking your hard cock? You explode all in my hand? You deserve it, I like you very much nice man. Cum for me, darlink. Shoot your big man cock..."

Soon the commentary was too much and I began to feel the tingle build again. But this time I didn't resist. Instead, I kissed her and, just as she'd fucked my hands, began driving my cock hard in and out of her palms until I felt her hook one leg over my hip and suck my tongue furiously. The tingle became a buzz, became a glow and finally, an explosion of pleasure that washed all through my body and left me reeling in her arms.

She pulled herself over on top of me and began body sliding against me so that my sensitive cock ached with more pleasure and my hot sticky load was rubbed into both our skin. Eventually she allowed me to rise, then followed me into the shower where she gave me one of the most intimate and thorough bathings I've ever experienced.

Then she dried me, helped me dress, and when she was ready to farewell me, offered me one last, slow, sensual kiss.

"I like you nice man with big man cock. You come see me again?"

"Oh baby," I gasped as I slipped out the door, "without a doubt."

****