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#1
10-29-2007
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Who Took Your Virginity?
If you've been one of the few lucky guys on this forum who have actually been with a shemale and lost there tgirl virginity who was it that took it?
Was she quite famous or not, did you pay or not and what was it like? I'm still a tgirl virgin unfortunately, like most of the guys here.  So if you are too tell us who you'd like to lose your cherry to in this post - http://forum.transladyboy.com/showthread.php?t=426
__________________
Tlover  Give it a go, you never know.
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#4
10-30-2007
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You're free to don't believe me, but i losed my virginity with a paraplegic transexual. She was a pro and a car run over her while she was working. She loved me, but i didn't love her. Her name was Chiara, and she was a very tall blonde.
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#5
10-30-2007
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I lost my virginity to a fine little creole lady named liza.She wasn't all that big,But damn did it feel so good.
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#7
11-02-2007
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My cousin took my virginity when i was 16 or 17 and i took his virginity
 As a shemale, she was a pro and a huge cock 
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#9
11-11-2007
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I lost mine to a freelancer name ammy, in pattaya
She worked on beach Rd. We went out the first night I was there, and picked 2 LB,s from stringfellow's club Went back to my hotel, and had an awesome night!! 
__________________
If she aint got a dick......... she's just a chick!
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#10
09-08-2008
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well as i said in the who will take ur virginity post....
if i could have choosen who it would have been then that would be Areeya.....but i lost my verginity to my maid in india.....when i was around 17 we had this maid who could speak english ....which was very rare anyway at that time i dint know i had a thing for shemales .....all i knew was that i wanted to fuck her brains out....so i made a move on her when parents wernt home she played along till the clothes came off then i saw her bonner and for some reason just went down and sucked it ......then she took control and fucked me ...since then i have loved beeing dominated
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#11
09-08-2008
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I lost my shemale virginity to a worker in Richmond, VA named Amber. She was pretty hung and had a nice rack...
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#12
09-12-2008
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I was ** at the swimming pool when I met a older guy. I went back to his place and he striped me down. He played with me and sucked me until I was ready to come then stopped. I got a little nervious when he reached into the end table drawer and got out some lube and got my bottom ready. When he striped I almost fainted. His cock was quite large with a very big head covered in foreskin. He sat down with me kneeling between his knees. I had never sucked before but I took him in my mouth. He got hard right away and was 8 inches at least. He put me over the arm of his couch and told me to relax. He rubbed my lower back for a while then spread my legs. It was great when he mounted me. I squirmed and squealed until he put me on my back and fucked me till he came. He played with my nipples and jacked me off until I came. Almost every day that summer I went to his house. As soon as I got inside I striped down and let him play with me. It was always a thrill when he reached for the tube of lube and got me ready. But that only happened two or three times a week.
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#13
09-12-2008
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hmmm i'm definitely playing with my cock reading some of these stories. Keep em cumming guys!!!
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#14
09-17-2008
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Quote:
Maybe one of those niche market videos that everyone here would like to be a part of. 
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#16
09-26-2008
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Quote:
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#17
09-28-2008
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no one ,,, i am waiting for a shemale to take it
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#18
10-09-2008
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I was *** when i lost my viginty to a older man he new that i was a very fem boy and a bit of a so he took me home and he made me put a nice skirt
on and a wig and then he got me to suck his cock then three over men came into the room i had to suck each one intern thay then lifted me up and sat me on the smallest on untill they had all fuck me the bigest one was about 9 ing long and realy thick this is wy i have allways got a smile on my face
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#20
10-16-2008
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Back when I was young, bone thin and less than a hundred pounds I was hitch hiking home one evening and a handsome older man picked me up. After a few minutes of pointless questions he put his hand on my knee and asked me if I would like a blow job. I was extremly shy but who could say no to that? We went into the woods and he put a blanket on the ground. I sat down but he stood before me and dropped his pants, his cock was steadily growing larger when he asked me if he could undress me, I didn't object, so he started with my shirt, rubbing and sucking my nipples, then he un-did my pants, I always wore panties and when he saw them he just stared, his cock shot straight up and pre-cum started to leak out. He turned around and we layed side by side and 69ed each other. Thats when I found my love for the taste of pre-cum. I had little idea what to do but he had had lots of practice, I really loved sucking him the little bit that I could but the smell of cock and his pubes tickling my nose was wonderful, I knew I had lots to learn. When he had me hard he rolled me over. As my fresh little round bottom stuck up in the air he laid on top of me. I felt his weight as he whispered in my ear, "Have you ever done this before?. I opened my legs and said no. He entered me slowly, I loved it, on the way home his warm cum seeped into my panties and felt heavenly. He parked a block away from my home and kissed me passionatly goodbye, telling me he would pick me up for another session the next day. I wore those wet cummy panties all night thinking only of him looking forward to seeing him again thinking of all the ways I could pleasure him more.
 Unfortunatly, he never did show,  I have looked for him in every man I have had sex with, I would love to see him again and show him what I have learned.
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#22
10-17-2008
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still virgin, maybe this year in las vagas
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#24
10-20-2008
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I lost my virginity when I was 14 (that was before I started dressing). I was at a friend's house.. Our clothes had gotten muddy, so we went up to his room to change. First our shirts came off, then our pants. We were talking and getting really turned-on. Before he could get his fresh jeans on, I decided to make my move. I reached over and started rubbing his half hard cock through his underwear. I reached in and pulled his beautiful cock and started to tease the tip. He took me over to his bed where I started giving him a blowjob, my first. As I sucked his cock I could clearly tell by his breath and precum that he was enjoying himself.
After sucking his cock for what felt like a blissful eternity. He pulled me off his cock, rolled me over, and drove his cock in my ass. He didn't use any lube, or open me up or anything. IT HURT!!! He fucked me hard for about 10 or 15 minutes before he exploded in my ass. I stood on my wobbly legs and we got dressed. That was my only experience with him. However, it opened a whole new world for me.
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#25
10-20-2008
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Bruna
Back in 2002, I decided to take a vacation and go down to Brazil for carnival. I was already a TGirl lover back then, and I became friends with a brazilian guy in a forum like this one I'm posting now. Well, I met him in person during my stay in the country and he jokingly said he was not going to allow me to go back home without losing my "shemale virginity". I thought it was only that - a joke - but one night he actually took me to an all-shemale carnival party (it is a very famous party in Brazil during carnival - some crazier tv stations even show it live on late-night programs).
Anyways, this place was like TGirl heaven - hot feminine girls all around, flashing their tits and cocks for tease, booze flowing free... My friend kept talking to EVERY girl and pointing at me. I didn't understand much, but basically he was saying I was a foreigner who never had sex with a TGirl before. Pretty much all the girls got wild when they heard that, kissing me and touching my cock or gently slapping my butt - they didn't take it too seriously though. But then my luck changed - one of the girls, a beautiful blonde called Bruna (I only have the attached pics, sorry about the size), decided to make my day, took my by the hand and led me out of the party, into her car. She gave me a wonderful blowjob, and later put my hand on her cock and started moving her hips. I felt her getting hard, and even though I was nervous, I started stroking her dick right there. A few minutes later, we checked in the nearest hotel and I fucked her sweet ass all night long. However, I didn't get to suck her or get fucked - I only masturbated her as I fucked her. It was fucking great. After that, I went out with her every night, always ending up on the bed. On my last day in Brazil, I went to her house for a goodbye fuck, and that was when I finally got past my nerves and sucked her cock. The feeling of it getting hard in my mouth got me so horny that it wasn't long before I was begging her to stick it up my ass. She had a small dick, but that was a good thing since I was still a virgin. Then we switched roles, and finally both came very hard. It was fantastic. PS, sorry about the long post. I got carried away on my memories 
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#26
10-21-2008
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Quote:
__________________
_██_ (ಠ_ృ) I say they seem to be letting all SORTS of riff raff into the internet these days!
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#27
10-21-2008
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Quote:
I learned a few lessons on my trips to Brazil. If you know someone in the country, ask these person to guide you around and steer you away from the bad places. The golden rule - do NOT pick up girls or shemales off the streets. Use one of Brazil's two zillion shemale escort sites and call a girl that you have seen before on the Internet and is marked on the site as an english speaker (they usually suck at english, but it's actually quite funny and cute). Find a motel close to the hotel you're staying (any taxi driver can help you with that) and set up the meeting there. Don't take a lot of money, only what you agreed with the girl and a few extra bucks just in case - no jewelry or fancy watches either. Avoid the streets at night. Those tips will keep you out of the more "serious" trouble. Finally, try not to look like a tourist - just blend in as best as you can, or you'll be a sitting duck for muggers, even during the day. Once again, sorry about the off-topic
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#28
10-21-2008
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Quote:
wayyy hottt story
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#29
10-21-2008
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unfortunatly i'm still a tranny virgin, although i have two trips planned for next year which shoould remedy this. but when i lost my virginity it was to an ugly bird who plyed me with alchohol first. it was pathetic, i was paraletic my memorys of it are vague at best but i know i didn't fully enjoy it.
the first time i got a blow job was worse, i picked up this girl in a mcdonalds and brought her back to my house. the whole way there she was telling me how much she wanted to suck my cock. the whole way home i was imagining the perfect blowjob. we got back to my house which was empty, we kissed for a while then i went down on her for about a half an hour while fingering her, some of my best work she came at least twice. then came my turn, i lay back on the sofa smiling as she started sucking, or trying to as it turned out. dry mouth, toothy, lack of use of the tongue, and or hands, refusal to put it in further than an inch. after five minutes i had to tell her to stop. she wouldn't even let me fuck to. this was one of the most disappointing things that have ever happeed to me. it was a further year before i got a good blowjob.
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#30
12-01-2008
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I lost my virginity when i was 22 to a 28 year old hairdresser,(go figure!), he was very well equipped and uncut. I think that might be why i prefer large u/c cocks. I lost my ts virginity to a 35 y/o asian tranny (she was born in the USA though) a few years ago. Lee wasn't anywhere as big as the hairdresser, i'm guessing around 5.5", maybe a little bigger, but WOW she knew how to please me. So far she's the only ts to penitrate me.
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#31
12-01-2008
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My first time as Jennifer was not fun, I meet a guy at a party and he didn't know i wasn't all female and he put the moves on me and stupid me i went back to his apartment where we necked for awhile and he started feeling me up but when he slid his hand up my skirt he found out i was still a male and he wasn't very happy i think you can see where this is going and he smacked me around before he
 up my ass, Needless to say i didn't enjoy it at all  Jennifer
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#32
12-01-2008
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Quote:
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#33
12-01-2008
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I lost my virginity to a gorgeous man; he said I would always dream of it and I do.
I remember shaking as he started to flirt with me and asked me if I wanted to go to his place. I felt the bulge under his pants and I remember how hot and hard it was when I pulled his pants down. I remember looking at his cock through his shorts and feeling it. Pulling his shorts down and kissing the head of his cock, made it easy to start sucking. Once I got started, I did not want to stop. He asked me to give him a lap dance and feeling his cock through my panties made it hard to stand. I sat on his cock and rubbed it between my checks; I was so hot. He put me on my back and got between my legs. Then he asked me if this is what I really wanted. After he told me I would dream of him fucking me for the rest of my life, I felt his cock at my ass pusing in. He pushed a bit faster and harder than expected and I tried slowing him down; he was way to powerful to slow down. I could not push him down or push myself up. I could not close my legs and then I learned what it was like to be a woman. He pushed it in and it hurt. He then waited for me to catch my breath and finished pusing it in all the way. I was in heaven and loved it more than I thought I would. He started to go faster and faster and I learned when a man gets close sometime a girl just needs to take it and know she is in for the ride until he is done. It was one of the best fucks of my life and I still get hard thinking about it.
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#35
12-12-2008
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back when i was 14!
i was just a boy at that time and was going for these tutorials after school cause mom and dad always wanted me to be the best at everything, but i was in my own world doing my own thing, sex wasnt on my mind that much. so anyway one week i decided not to go to my tutorials and chill at a friends place instead......mom and dad couldnt find out they would think i am at the tutorials. anyway next week when i went to my tutorial my professor told me that my parents called last week and asked how i was doing....i panicked but he said he covered up for me i said i was doing great......i was so happy and greatfull thanked him soo manytimes.....but then he said that if i dont do what he wants me to do he will complain to my parents....so innocent me thinking that he was talking about school work so i said ok.... and he slowly put his hand on my thigh and strated rubbing it....i dint resist i was sort of shocked and also liked it a bit.....then as soon as i got hard he slowly took my pants of and kissed my 14 yearold dick.....he licked the tips delicately while his hands cupped my ass i really started to like it.....so i tapped him and said that i want to taste his dick ......he smiled and took me to his bed.....placed me on top of him in a 69 position and asked me to do to his cock what he is doing to mine so i did! thats when i fell in love with the taste of cock and pre cum and cum ohh my hard just thinking about this
i finally came and so did he right into my mouth he asked me not to spit (in a muffled voice since there was cum in his mouth too) instead he asked me to come and kiss him.....so i did swapping each others cum oh its was sooo good.....after that i never missed a tutorial i am still in touch with him.....you know the occasional fuck
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#36
12-12-2008
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Quote:
How old are you now? Piece, TAL
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#38
12-12-2008
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Hi, Cutie
Quote:
INDY: Sorry, my curiosity about your age was related to how cute you are in that middle photo. Where can I French kiss you to receive your pardon? Double wink to you, sweetie. Piece, TAL
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#39
12-12-2008
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True story - every word :)
It was in the small hours of the morning when I'd been visiting some bars on my last night in Bangkok... I was strolling down the sidewalk when I saw a sultry beauty sitting along at a table sipping on a drink. Soft, round feminine face, long hair tumbling over her shoulders, a breathtaking short beige dress with a plunging neckline and no bra. When she smiled at me, her perfect white teeth shone and her thick shiny lip gloss sparkled on soft, petite lips.
So I took the empty seat opposite her and the moment I sat down I knew we'd be going somewhere together. She easily broke into a chat, eyes darting about coquettishly, long slender fingers clutching her drink. Every time she moved forward I could see the smooth curves of her breasts and the edge of her plunging neckline seemed to keep catching on her bare nipple. I'd seen a lot of really rough women on the streets of Bangkok at this time of the morning, but this one was an absolute stunner, a complete honey! I ordered a beer, but only had two mouthfuls before I'd agreed to go with her to a short time hotel she knew for a very small price. We jumped into a cab and she took my hand and snuggled into me.. Which was just as well because I was having a great deal of difficulty keeping my hands to myself at this point. Into the room, she locked the door, put her handbag on the table, turned to me and slid the straps of the slinky little cocktail dress over her shoulders. It fell to the floor and there she was: a stunningly beautiful creation with firm breasts, slim hips, smooth tan skin and long slender legs. She stood there for a second on her high heels while I took in the view, her head cocked to one side, a sultry smile on her face and just a pair of tight black French knickers on - with a distinctive bulge where her slender thighs met. "Shower now," she said, kicking off her heels, turning towards the bathroom door and stripping off her knickers in one quick, well-practised move, giving me a glimpse of a surprisingly curvy feminine ass. But I still hadn't seen her dick. I stripped off as quickly as possible and climbed into the shower with her, whereupon she started soaping me all over. By this time I was totally committed to whatever would happen that night, my only fear that I'd awake in guilt the next day with all sorts of difficult questions about my sexuality. She soaped me all over, with extra attention, of course, to my balls, ass and cock - which immediately started its ascension. Finally I snuck a glimpse between her legs to see a perfect little cock at half mast, and not a thread of hair anywhere near it. Still too shy to touch it, I started stroking the smooth, soapy cheeks of her ass and suddenly felt an electrifying tingle through my body as our half erect cocks touched. Clearly we were ready for bed and we dried quickly and lay down on the large round bed - in Bangkok there are short time hotels designed for such liaisons - it was kitschy, but clean. And the bed was comfortable, but I wouldn't have cared if it was a tatami mat on the floor! Shit, I thought. What do I do now? There was this gorgeous shapely beauty beside me with body parts unlike any of the dozens of lithe young Asian girls I'd bonked over years of doing business in Asia... And I didn't really know what to do next. Was I ready to touch a cock for the first time? Was I really ready to put one in my mouth? No, I wasn't having doubts: but after many visits to ladyboy bars in Singapore and Bangkok, none of which ended with an orgasm, this was the moment I'd been both fantasising about and putting off for two years! I need not have worried. She knew what she was doing! After several tender, highly arousing kisses from her soft lips she turned around so we were positioned in a sideways 69 and took my now very hard erection in her mouth. It felt heavenly. I'm not exaggerating when I say there were tingles racing all through my body, like no experience I'd ever had with woman with a pussy. Of course there, not too far before my face, was this beautifully shaped dark erection, circumcised and shaped with a curve so it resembled a small banana. I didn't have time to hesitate because she took my hand and gently placed it on her. So I started to stroke it as if it was my own. After a short time she shuffled her hips so her cock was closer to my face. It truly looked beautiful and was so hard it sprung like it was made of rubber. It smelt of soap. So I took it in my mouth. She moaned, squealed almost. And I got to work, savouring the novel experiences, surprising myself by loving the feel of the smooth helmet rubbing against the roof of my mouth, nudging the top of my throat. I took it out, ran my tongue around the rim, up and down the shaft, took her tight shaven sack in my mouth, licking the curves of her balls like they were gobstoppers. Then took her cock in my mouth again and pumped it with my mouth remembering from being on the receiving end to take care with my teeth and move my tongue around as much as possible. Suddenly she pulled out. Shit, have I done something wrong. Then she relaxed a little and I rolled over so I was above her, driving my cock into her mouth and taking hers in mine again, this time from above. She started murmuring making a noise which must have been a Thai word, something think "oooi". Then she gently rolled my over on my side. "Do you mind if I cum?" she asked. Do I mind? My God, I've got her off! "Of course not." She knew full well it was my first time. Maybe she sensed that I might not be ready for the full experience just yet. So instead of putting it back in my mouth she took it in her hand and right before my face stroked her erection for what seemed like just a few seconds before sighing and shooting her thick cum across her thigh. For the first time in my life I had seen real life (not on a TV or computer screen) cum shoot from a cock that was not my own! She caught her breath for a moment then lay back down and resumed sucking my cock. Touching her cum with my fingertips and spreading around her thigh broke the seal. I warned her I was coming and instead of taking my cock out of her mouth she took it deeper and cupping my balls in her soft hand, sped up! I exploded and she took my full load in her mouth. While I lay there panting she took off to the bathroom to spit it all out and rinse her mouth out. Then she was back lying behind me, her still half erect cock pushed into the small of my back. Her arm encircled me, her hand gently teasing the last little drops from my softening cock. Not long later I kissed her on the lips outside the hotel as she climbed into a taxi and sped off into dawn light. I walked back to the hotel alone, a smile on my face the whole way and not a shred of doubt or guilt about what I'd done. My only regret was that I was flying home later that day...If I'd had another night I would have hooked up with another one and lost the next level of virginity - but pumping a beautiful young woman with a cock in her tight arse would have to wait for another day... In fact at the time of writing it remains a dream, alas.....
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#41
01-29-2009
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A sweet guy in a nightclub dark room fucked my ass for the first time: he sat while sipping his wine on a couch while I embraced his boner with my very lubricated ass...I wore a red leather miniskirt and boots. He kept my panties. I did not cum until I drove away in my car, rubbing my cock against the seat.
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#42
01-30-2009
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I lost my virginity about 2 month's ago:$ to my home buddie that was really turned on by me as a girl.
I dind;t lost my real virginty yet I never fucked anyone (no guy , no girl , nothing) p.s. but it can't be better than being fuck, could it ?
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#43
06-20-2011
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How I Popped My Cherry
I'd been dressing since I was young but I was down at a convention with the family at a uk holiday resort.
Being an only child I'd made friends with another group of teenagers. Getting near the end of the week I'd been round at there accomodation having a bit of a party. Walking back I'd bumped into one of holiday reps, who was obviously gay but we'd chatted to and joked around with over the week. As it was late he was finished his shift and heading back to his on site appartment. We were chatting away and he explained his female flatmate was off on leave, so he invited me back. We got back to his and after a few drinks and a laugh the chat got a bit flirty. I jokingly made a remark about one of us needing to be the girl for that to work. Slowly one thing led to another and with his flatmate being away we had a wardrobe full of clothes and a bathroom full of cosmetics at my disposal. My younger slender self meant most of her clothes fitted me. Being a wannabe rocker my shoulder length hair didnt need to much work to glam up and even my very amateur attempt at make up looked quite good. We had dolled me up into a sexy little femboy. I felt great, it was such a thrill. I'd found a red dress and stockings. Although I was nervous and my arms trembled a little we began to kiss and fell back on the couch. Pulling the lace knickers aside he began to suck my cock. That was all I needed, nerves and inhibitions aside I was all over him. Straddling and kissing on the sofa soon led on to fun in the bedroom. I bent over on the bed so horny and desperate to be fucked. Id parted my knees wider and spread open my fishnet clad legs as he pulled the red dress up exposing my eager hole. He was considerate and after some anal play with lube he slowly eased his cock in. He was around 6.5 but had thick girth. My make up smeared all over the pillow as I had to bury my head. As he penetrated it was painful, I moaned and sunk my head in the covers. As my ass eased off on his full length I began to enjoy it. By the time late morning came the next day and I'd left to pack for the trip home. we had done it four times! Experimented with different outfits and loved every minute of it!
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#44
06-20-2011
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the first time i was sexually with a ts, i was 30, blind drunk, she was a hooker and i payed her $50 to suck her. but i wouldnt really call that popping the cheery.
a year later and i met a ts from dating site, we went out on a few dates, then one night, we did the deed. it was amazing, ahah we were a little unprepared, we didnt have any lube so used baby oil, needless to say it got a little warm for her. it was amazing and we ended up being together for just over another year.
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#46
06-20-2011
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My first time getting fucked as a girl was with a guy I met online. I won't go into all the details but let's just say I got seriously ploughed. ouch.
__________________
 My lips, your asshole... A match made in heaven.
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#48
06-22-2011
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In London, early autumn 2002. London is an ocean full of tranny talent, so one day I took the plunge and have never regretted it.
It was an escort near Tottenham Court Road, at the northern most end of the street. She was small in cock size, maybe only four inches or so, but it remains one of my greatest sexual times ever. the feeling of her cock in my arse, and more to the point, the feeling of her cock on my prostate, sent me over the edge and I was in my element. I'm sure the maid probably heard me moaning, as the apartment was not so large, but I didn't care.
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#49
06-25-2011
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Quote:
Last edited by aussie ben; 06-25-2011 at 07:32 AM.
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