Closet tranny first time sex. Transsexuals & Crossdressers Stories.



Closet tranny first time sex

Closet tranny first time sex

I was all dressed up, looking for my first taste of cock. I'd done myself up pretty well, great make-up, hair looking good, scarlet blouse it was warm enough not to need a jacket , black skirt finishing about 3" above the knee, matching black lacy bra, thong and suspender belt, plain black stockings but I always carried a spare pair or 2 with me , 3" black strappy mules to finish off. It was a large community park, but a no-go area after 10pm unless you were looking for something special.

I'd heard it had its usual population of drunks and hobo's on any particular night, but they weren't a real problem. I parked my car in the adjoining car park and drew a deep breath, checked myself in the rear view mirror, grabbed my handbag and stepped out of the car.

The night air was still warm, but a cool ish breeze was picking up, sending a shiver down my spine. I strolled towards the park entrance, trying not to walk too tarty, but still trying to make anyone interested know why I was there!!! The park itself was reasonably well lit, some of it quite open, some of it quite sheltered. I walked on for a couple of minutes before finding a bench to sit down on slightly off, but facing, the main path.

I sat down and pulled a cigarette from my bag, lighting it and inhaling that nerve-numbing first drag. I felt myself sit back slightly, easing into the relatively hard wooden bench; I was certainly more at ease and crossed my legs. They continued passed on up the path, a couple of them looking back for a longer look, obviously with a stirring in their loins. I finally finished my cigarette, dropping it to the floor, stubbing it out under my shoe, I was about to get up and move further into the park when one of the young lads came up to me, quite handsome, I guess, blondish streaky hair, about 20 years old I suppose.

He was well spoken, polite, obviously attached to the university that was close by; he explained that he was actually on his way back to his campus room as he'd forgotten his wallet, the guys he was with gave him a little dig, suggesting that he was simply going back to try and pick me up!!!! I didn't mind, he was certainly good looking enough to make me blush!! His name was Jon. No problem I thought. We headed off across the park, westwards I think, finally coming to a different exit from where I parked, right next to the campus residence.

Despite his request to go up to his room, I remained just outside the residence entrance waiting for him. He wasn't long, and we strolled back into the park, striking up polite conversation. That is when I dropped the killer line I was quite embarrassed, I'd expected him to kick my fucking head in or something or at least tell me to fuck off!!! But no, he was quite charming. But I was here now, and Jon's sheer kindness kinda hinted that I would be okay with this one. Jon's meagre attempt at resistance was futile, I wanted him, he wanted me!!

In the relative seclusion of the bushes I slowly ran my hand over Jon's chest, clad in his light denim shirt, he was no J C van Damme, but firm ish. We kissed, tongues lashing, but I was in no mood for foreplay. I moved my hand over his groin, feeling his rock hard little man, straining to get free, I had to do what it commanded of me.

Undoing Jon's belt and unzipping Jon's fly, I reached inside his plain white boxers, wrapping my hand around his hot, throbbing member. Slowly I started to wank him off, his groans clear in the still night air. I stood back from him, looking him deep in the eyes, a grin on my face, I started to strip. The look on his face was incredible. I peeled off my scarlet blouse, and dropped it to the floor, then began pulling down my skirt, revealing my lacy suspender belt and black stocking tops; Jon's cock just swelled, agonising awaiting to release its gift.

Finally I kicked off my shoes, leaving me in just my underwear. He gestured to come to him, I started, but he stopped me, no he wanted me to crawl. Getting onto my hand and knees I crawled across the damp ground, littered with dead leaves, broken twigs, this was turning me on. I came to where Jon was standing, I looked up to see his cock still erect, still throbbing.

Getting to my knees I gave him a quick wink then took him deep into my mouth. He tasted so good, he'd obviously given his cock a good clean before going out. I licked the pre-cum soaked tend tasting its unusual flavour, and took him deeper and deeper, sucking him, caressing his shaft with my tongue.

Jon moved faster, his rhythm matching mine, finally I felt him buck, he let out a glorious cry, splattering the back of my throat with him cum, I pulled back, lay on my back and brought my feet up to take the rest of his gift over my black stockinged feet. His cum kept flowing, I loved the feel of it soaking into my stockings, I pumped for more and got what I asked for.

But it soon got better, Jon slipped in and out very nicely, bringing me very close to climax. My cock was as stiff as it had ever been, I started to stroke it, but then Jon moved his hand over and did the job for me; I orgasmed like never before, while Jon kept driving his lush cock deep into my ass. It was three guys, big guys, bikers by the look of it. With that Jon pulled his cock out of my ass, grabbed his stuff and scarpered!!! I thought about just grabbing my handbag and making a dash for the car, but it was too close to one of the men.

With that all three guys, unzipped their jeans and pulled out their cocks. The ring leader went behind me, flipped me over on my back and shoved his cock straight up my fuck-hole, luckily he wasn't very well endowed and slipped in quite easily, I tried hard not to snigger. The other guys brought their cocks to bear by my mouth, instructing me to lick and suck, while they tugged vigorously at their pricks. It wasn't long before the first explosion of cum hit my face, shortly the second, then finally the fat brute that so eloquently bum-fucked me with his measly prick, pulled out and literally jet-washed my belly, chest and bra with cum, it seemed like fucking gallons!!!!

He undid my left suspender straps and proceeded to wipe his cum soaked cock in my stocking top, smiling he pushed his finger through the delicate nylon material, "won't need these again, will you doll!!! With that he moved me onto all fours and beckoned the other 2 over.

With three standing behind me, I didn't know what to do. Suddenly I felt their hands all over my legs, caressing me, my cock grew stiff again, no matter how hard I tried to stop it. Next the sound of tearing nylon as they proceeded to rip my stockings off me, rolling me back onto my back, they pulled at my suspender belt, breaking one of the clasps, ripping my stockings to shreds, I struggled to undo the back fastening, managing to do so, as they pulled a conquest trophy clean off me!!!

Laughing, all three stood up, one of them picking up my panties and taking that too. I sat there for about two minutes, composing myself. I was covered in dirt and cum, my underwear had been ripped clean off, I was sobbing and my stockings were not even recognisable as stockings.

Finally I got up, took off what remained of my stockings, got dressed and went back to the car. I was glad to get home, once inside I cleaned myself up, slipped into a red negligee, panties and red hold-up stockings, sat down and poured a large glass of red wine. I looked at the clock, it was gone 1am. I thought about Jon, nice, sexy, chicken-shit, and I thought of my sexual-blitzkrieg by three horny bikers -- in all, it wasn't that bad a night!!!

My next trip to the park was even better, but you'll have to wait!!!

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I SUCKED HIM ON THE FIRST DATE



Closet tranny first time sex

I was all dressed up, looking for my first taste of cock. I'd done myself up pretty well, great make-up, hair looking good, scarlet blouse it was warm enough not to need a jacket , black skirt finishing about 3" above the knee, matching black lacy bra, thong and suspender belt, plain black stockings but I always carried a spare pair or 2 with me , 3" black strappy mules to finish off. It was a large community park, but a no-go area after 10pm unless you were looking for something special. I'd heard it had its usual population of drunks and hobo's on any particular night, but they weren't a real problem.

I parked my car in the adjoining car park and drew a deep breath, checked myself in the rear view mirror, grabbed my handbag and stepped out of the car. The night air was still warm, but a cool ish breeze was picking up, sending a shiver down my spine. I strolled towards the park entrance, trying not to walk too tarty, but still trying to make anyone interested know why I was there!!!

The park itself was reasonably well lit, some of it quite open, some of it quite sheltered. I walked on for a couple of minutes before finding a bench to sit down on slightly off, but facing, the main path.

I sat down and pulled a cigarette from my bag, lighting it and inhaling that nerve-numbing first drag. I felt myself sit back slightly, easing into the relatively hard wooden bench; I was certainly more at ease and crossed my legs.

They continued passed on up the path, a couple of them looking back for a longer look, obviously with a stirring in their loins. I finally finished my cigarette, dropping it to the floor, stubbing it out under my shoe, I was about to get up and move further into the park when one of the young lads came up to me, quite handsome, I guess, blondish streaky hair, about 20 years old I suppose.

He was well spoken, polite, obviously attached to the university that was close by; he explained that he was actually on his way back to his campus room as he'd forgotten his wallet, the guys he was with gave him a little dig, suggesting that he was simply going back to try and pick me up!!!! I didn't mind, he was certainly good looking enough to make me blush!! His name was Jon. No problem I thought. We headed off across the park, westwards I think, finally coming to a different exit from where I parked, right next to the campus residence.

Despite his request to go up to his room, I remained just outside the residence entrance waiting for him. He wasn't long, and we strolled back into the park, striking up polite conversation. That is when I dropped the killer line I was quite embarrassed, I'd expected him to kick my fucking head in or something or at least tell me to fuck off!!!

But no, he was quite charming. But I was here now, and Jon's sheer kindness kinda hinted that I would be okay with this one. Jon's meagre attempt at resistance was futile, I wanted him, he wanted me!! In the relative seclusion of the bushes I slowly ran my hand over Jon's chest, clad in his light denim shirt, he was no J C van Damme, but firm ish.

We kissed, tongues lashing, but I was in no mood for foreplay. I moved my hand over his groin, feeling his rock hard little man, straining to get free, I had to do what it commanded of me. Undoing Jon's belt and unzipping Jon's fly, I reached inside his plain white boxers, wrapping my hand around his hot, throbbing member. Slowly I started to wank him off, his groans clear in the still night air.

I stood back from him, looking him deep in the eyes, a grin on my face, I started to strip. The look on his face was incredible. I peeled off my scarlet blouse, and dropped it to the floor, then began pulling down my skirt, revealing my lacy suspender belt and black stocking tops; Jon's cock just swelled, agonising awaiting to release its gift. Finally I kicked off my shoes, leaving me in just my underwear.

He gestured to come to him, I started, but he stopped me, no he wanted me to crawl. Getting onto my hand and knees I crawled across the damp ground, littered with dead leaves, broken twigs, this was turning me on. I came to where Jon was standing, I looked up to see his cock still erect, still throbbing. Getting to my knees I gave him a quick wink then took him deep into my mouth.

He tasted so good, he'd obviously given his cock a good clean before going out. I licked the pre-cum soaked tend tasting its unusual flavour, and took him deeper and deeper, sucking him, caressing his shaft with my tongue.

Jon moved faster, his rhythm matching mine, finally I felt him buck, he let out a glorious cry, splattering the back of my throat with him cum, I pulled back, lay on my back and brought my feet up to take the rest of his gift over my black stockinged feet. His cum kept flowing, I loved the feel of it soaking into my stockings, I pumped for more and got what I asked for. But it soon got better, Jon slipped in and out very nicely, bringing me very close to climax. My cock was as stiff as it had ever been, I started to stroke it, but then Jon moved his hand over and did the job for me; I orgasmed like never before, while Jon kept driving his lush cock deep into my ass.

It was three guys, big guys, bikers by the look of it. With that Jon pulled his cock out of my ass, grabbed his stuff and scarpered!!! I thought about just grabbing my handbag and making a dash for the car, but it was too close to one of the men. With that all three guys, unzipped their jeans and pulled out their cocks. The ring leader went behind me, flipped me over on my back and shoved his cock straight up my fuck-hole, luckily he wasn't very well endowed and slipped in quite easily, I tried hard not to snigger.

The other guys brought their cocks to bear by my mouth, instructing me to lick and suck, while they tugged vigorously at their pricks. It wasn't long before the first explosion of cum hit my face, shortly the second, then finally the fat brute that so eloquently bum-fucked me with his measly prick, pulled out and literally jet-washed my belly, chest and bra with cum, it seemed like fucking gallons!!!!

He undid my left suspender straps and proceeded to wipe his cum soaked cock in my stocking top, smiling he pushed his finger through the delicate nylon material, "won't need these again, will you doll!!! With that he moved me onto all fours and beckoned the other 2 over. With three standing behind me, I didn't know what to do. Suddenly I felt their hands all over my legs, caressing me, my cock grew stiff again, no matter how hard I tried to stop it. Next the sound of tearing nylon as they proceeded to rip my stockings off me, rolling me back onto my back, they pulled at my suspender belt, breaking one of the clasps, ripping my stockings to shreds, I struggled to undo the back fastening, managing to do so, as they pulled a conquest trophy clean off me!!!

Laughing, all three stood up, one of them picking up my panties and taking that too. I sat there for about two minutes, composing myself. I was covered in dirt and cum, my underwear had been ripped clean off, I was sobbing and my stockings were not even recognisable as stockings. Finally I got up, took off what remained of my stockings, got dressed and went back to the car.

I was glad to get home, once inside I cleaned myself up, slipped into a red negligee, panties and red hold-up stockings, sat down and poured a large glass of red wine. I looked at the clock, it was gone 1am.

I thought about Jon, nice, sexy, chicken-shit, and I thought of my sexual-blitzkrieg by three horny bikers -- in all, it wasn't that bad a night!!! My next trip to the park was even better, but you'll have to wait!!!

Closet tranny first time sex

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3 Comments

  1. His cum kept flowing, I loved the feel of it soaking into my stockings, I pumped for more and got what I asked for. Crossdresser for first time. In the relative seclusion of the bushes I slowly ran my hand over Jon's chest, clad in his light denim shirt, he was no J C van Damme, but firm ish.

  2. He wasn't long, and we strolled back into the park, striking up polite conversation. I was covered in dirt and cum, my underwear had been ripped clean off, I was sobbing and my stockings were not even recognisable as stockings. They continued passed on up the path, a couple of them looking back for a longer look, obviously with a stirring in their loins.

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