tagTransgender & CrossdressersReceiving her Thanksgiving

Receiving her Thanksgiving


It'd been at least half a year since I'd last seen my parents, when they swung around to catch my twenty-fifth birthday. They'd ask to visit now and then, of course, ask me to come over, but... the drive's a few hours, I'm a busy (yes, busy!) man, and... honestly, what'd I do with my parents? Every week day was a work day, and work days were long days, and the few precious weekends I'd keep to myself were ones I held on to.

But I could do holidays. And I did, so there I was. Thanksgiving morning, standing at the door to my parents' house, rising sun peeking through the towering skyline, wearing a casual t-shirt and pants.

Greetings as usual, after that. I'd planned to exhaust the same stockpile of pleasantries that I kept saved up for occasions such as this. Answers to novel questions such as 'how've you been?' or 'why don't you visit us more often?' Not that I -disliked- them, of course. But how many types of those conversations can you have with your parents?

Still, I hadn't counted on the day being interesting. Comfortable, relaxing, maybe. But interesting? Not a chance, I thought, until I was introduced to her - Claire. A woman, about my age and height, which was odd. One of the first things I noticed was her bronze-colored eyes - piercing, intelligent... flirty... sealed away behind a pair of pink glasses which did nothing to make her look any less confident. She had her black hair tied in a bun behind her head, short bangs comfortably above her medium-thick eyebrows, gorgeously soft lips. Below that she wore casual clothes - very modest and plain. A low cut, white shirt which barely contained her large, shapely breasts, and loose black pants underneath. Absolutely brimming with confident feminity. I didn't try to hide that I was checking her out - I wasn't the shy type, for one, and on top of that she wasn't trying to hide that -she- was checking me out either. I'd been with women before, never bothered settling down. I liked to think I was attractive. To use a cliche term, a womanizer, when I bothered to be. Perhaps a bit overconfident, but... still.

She was polite, punctuating every other sentence to my parents with a misses or mister. Friendly, though, particularly with my dad. I'd have been suspicious if he weren't such an old fart. He hastily introduced her as a co-worker he'd invited over. They were good friends (oddly enough) and she lived alone... not too out of the ordinary, I supposed. We exchanged our greetings, I made small talk for a while, with her and with the parents, and then we ate a (late) breakfast. The day after that was relatively normal save for the hour or two of conversation I managed to have with her. All relatively normal subjects, which took me off guard, as I'd expected her to be a lot more flirty. I could see it in her eyes, and yet she was seemingly almost a model of restraint.

Or so I supposed. Supposed. Our line of conversation having faded away into meaninglessness, she got up and walked past me... I, assuming our conversation over, got up as well, and as she passed me, she whispered into my ear, "How do you feel about a little bit of... thanks-giving, stud?" It took me off guard for a few seconds before I stammered, "No foreplay?" and she chuckled, traced her fingers along the slight bulge in my pants, and I gulped. "There are dicks that need release here, darling," she whisper-purred, "and who am I to deny them the pleasure?"

So she took my hand (with surprising force) and led me upstairs, into the bathroom. Within a half minute the door was shut and we were alone. As close to alone as we could be, at least. And she stepped forward, mashed her massive breasts against me, and gave me a slow kiss on the lips, her deep bronze eyes gazing into mine with pure, unadulterated, feminine lust. My hands reached to her hips, undid her pants as her own hands did the same to mine... and then she pulled back, a trickster's gleam in her eyes as she gently pushed me back onto the counter, until I was half sitting, half lying on its smooth, cold surface. She finished pulling my pants down, slipped my boxers off and let my now fully erect dick spike into the air, bent down and gave it a few tender kisses, her smooth tongue gracing my cockhead with a few slow, gentle licks, before she moved herself up, her face right up to mine, her large breasts blocking my vision entirely. I could feel her hot breath on my face as she stood there, bent over me, and I noted just how obviously submissive my position was. Her left hand moved to my shoulder as I heard her pants audibly drop to the floor, leaned on me as her right hand reached up to my nethers, giving my dick a few gentle strokes before she reached her hand lower and (of -course-) guided her... thick shaft into my ass, pressed it against my virgin hole. I gasped from the surprise, looked up at her with eyes that screamed, 'What the fuck?', but didn't dare actually make anything close to noise. She looked up at me, face still wearing that same, devilish trickiness, brought her right hand up, spit into it, coated her dick in her saliva before slowly, painstakingly so, pushing into my ass, my face flushed crimson as she did so - as I lost my -other- virginity, to a woman, no less.

She kept pushing in, slowly, still. Slowly. I felt her cockhead push into my ass, my ass stretch out to accommodate the invading member, her grip on my shoulder tighten as her right hand moved to my hip, her huge breasts pressing against my chest... "Virgin tight," she said, smugly, "I'm not disappointed." And then her head was in, the stretching sensation subsiding a bit, her spit-slick shaft sliding into me, the warm mass of cockflesh pulsing with energy, her dick thick, possibly thicker than mine. Long to match, probably. Looking down I could see only her cleavage, still locked away behind her shirt as she fucked me. And her shaft pushed into my ass, halfway through, I guessed. I hoped. A tingle of pleasure passed through me, starting at my dick and moving up my spine, the soft, dull pleasure unexpected, but... well, pleasurable, of course. It was... strange... Me, a man - a STRAIGHT man - lying there on the counter, back propped against the wall, a woman my size standing above me, breathing into my face, sliding herself into me. My own dick standing there, mostly erect, grazing against her stomach now and then.

And she was in, all the way, her smooth crotch pressing against my ass. It was a strange sensation. There was warmth, fullness, a slight tingling of pleasure with every throb of her easily above average dick, and... there was the oddity of the sensation all-in-all, the uncomfortableness of being stretched out for the first time, but that was easily dulled out in the heat of the moment. Even more so as she pulled out, faster now. I looked into her eyes, saw that flirty, intelligent dominance in them, looked away and shut my eyes, cheeks flaring redder from the shame of it. She pulled out, the friction sending a more intense, but still gentle, pulse of pleasure through me. It was, well, not that bad, honestly. Not something I'd talk about... ever... but not unenjoyable. Honestly? I liked it. I bent upwards, puckered up for a kiss, hesitated, opened my eyes for a split moment to look into hers. She pulled her dick out of me almost entirely, then pushed it in again, faster now, me moaning ever so slightly from the stimulation, her grunting a bit, and as she did so, she reached a hand up to my jaw, and pressed her lips against mine. Startling my eyes open as her tongue shot between my lips, as she kissed me, passionately. Forcefully. Her dick bottomed out in me once more and she slid out, faster now, me gasping into her mouth as she kissed me, her virtually face-fucking me with her tongue, as she rammed her cock into me once more, drawing out another moan, muted, but louder. She pulled out, thrust in, thrust in again, the last tinges of discomfort drowned with the intensity of each thrust, the fullness becoming almost pleasurable in and of itself.

Her hands pushed me into the wall, resting her weight on my shoulders as she fucked me, working the rhythm up to an actual thrusting, my oversensitive, virgin prostate buckling with overstimulation, my legs and arms weak, me gently holding onto her sides as she rammed into me, each thrust bringing me closer to the edge. I moaned into her mouth, barely able to hold myself back, feeling comparable exhalations of pleasure coming from her. Then she drew back, licking my lips playfully before she drew her head back, biting her lip as she slammed into me again. Electric shocks of pleasure shot through my spine with every thrust - one, two, every brush past prostate better than the last... three, four, and my ass clenched around her, a line of cum shooting against her belly, and again, my seed dripping back down onto me, liquid masculinity shooting, then drooling down as it leaked out of my dick, every ounce of cum squeezed out by my abused prostate.

My own orgasm didn't stop her, and she kept fucking me, railing me, her own dick pulsing and twitching inside me, inches of girthy masculinity riding in and out of my hole as she worked towards her own climax. I could feel her grunting, mutedly, barely containing herself, and I could see the mounting lust in her eyes as I stared into them. She decked out in me again, and this time, she didn't pull out. A second, half-second later, her dick throbbed and I felt a line of cum shoot into my bowels, seed splattering my insides as I half-moaned, my body still rocking from post-orgasmic bliss, that now-comfortable fullness accentuated by the feeling of semen - a woman's semen - shooting into me. One line, then another filled me as she stood there, gently rocking her hips, riding out her climax, dicked tucked away inside of me. She leaned down, kissed me again, dick spurting one last shot of cum into me before drying up, us standing there, me filled with her cum and us both covered in my own... her warm, massive breasts still pressing into me...

She pulled out, let some seed trickle out of me, suckled my dick for a few moments, licked at the head, then stood up, and I looked up into her eyes, barely handling the aftersex, ass still pulsing with raw sensitivity. "That was..." I stammered, unable to finish my own sentence. She smirked a bit, looked at me, "That was? ... Well, you were a ride, cowboy." And I looked down at her still erect, cum-slick dick and noted that she really -was- longer than me. Damn.

We cleaned up, after that. Obviously. Well, too, because I didn't intend to show up for a meal smelling like semen.

We stayed the rest of the day, neither of us bringing up the 'festivities' that had taken place, me out of embarrassment and her, presumably, because she enjoyed watching me squirm under her gaze. The day passed uneventfully, though Claire kept making casual jabs at me once dinner rolled around. Most of them were subtle enough that I wasn't sure if she meant anything at all, but then she'd glance my way and wink, or not wink at all, and I knew she -did- mean it.

When I left, I promised my parents that I'd visit again, I said a muted goodbye to her, and I went on my way. A little after arriving, I got a text. From her, naturally.

"Hey, cowboy, feel like another ride on the bull?"

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byPENISADVENTURELAND© 8 comments/ 34759 views/ 59 favorites
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by Anonymous

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by Gordon113505/13/19


Wonderful little rape job with some fine description accompanying. Now you could write a sequel where they can get together and she can get him into her bed and give him a really good working over, bothmore...

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