I was about 15 when i found a bounty of porn magazines and female lingerie in the park near my parents house. Without thinking at all i grabbed it and took it home. that night after getting horny reading some of the porn magazines I tried on some of the stockings and silky lingerie. it was the sexiest feeling i had ever felt. they seemed like a natural fit for me, as i had a slim and somewhat girlish figure.
Over the next few months i regularly played with myself while dressed up and reading the mags. but after a while, without the magazines, imagining I was a girl, with my legs spread wide and with a big cock entering me. just fantasizing about the feeling of being a girl with that big cock sliding in and out of me... anyway after a while i threw all the stuff away because i thought it was too weird.
when i was 17 i used to mow the lawn for a neighbor, Roger. He was a single man in his 40's. one day i noticed that he had a lot of ladies clothes and panties on his line. i figured it must have been a girlfriend or something.
A few months later i was feeding his cat while he was away, i opened a cabinet below his TV and found a number of Video Cassettes. they were porn. i put one on and started watching. after a few minutes, the penny dropped, it was tranny (shemale) porn. it was the hottest thing i had ever seen in my life. a tranny girl being banged by a big black guy, that big cock sliding in and out of her.. i think i came right then in my pants.
I was watching different videos every time i came back, and also dressing up in some lingerie that was in a box by the video. i figured that roger must like dressing up too. my favourite video rapidly became a tranny getting hammered in a 3sum with two black guys. i fantasised about being that girl, getting spitroasted by this 2 big guys..
Anyway roger came back and everything was back to normal. although i was hungering to see that porn again.. which was hard for me to get. one holidays when my parents were away I sneaked in while I was mowing the lawn and grabbed the video so i could copy it at home. (a difficult and time consuming task back then with VCR's). I copied it but then had to get the video back. I had to wait til the following weekend and while mowing the lawn again, snuck in, opened the cabinet, slid the video back in, closed the cabinet and there was Roger, staring at me.
um i just was wondering what video you had sorry.. umm .. Roger said don't worry, its ok. he walked to the cabinet, opened it up and pulled out the video i had borrowed. This is one of my favorites. I turned bright red, said sorry again, i think i even started crying. he said don't worry its fine, was really nice, offered me a cold beer, and started to talk about how watching porn is ok, and dressing up is ok too. I felt comfortable and confessed to him about dressing up in his gear, he said he had suspected so, and said he was glad to find a friend with a similar interest.
Roger also suggested we dress up one time, i was a bit nervous but the next week I asked him if i could wear some of his lingerie. he was only to kind to share his collection with me, but also applied some makeup to me and gave me a blonde wig and some high heels. I was so nervous and turned on while he was applying the makeup, and as i slipped into the 4 inch stiletto boots. my cock bulging in the lacy panties underneath the miniskirt I had on. when he had finished i stood up in front of a full length mirror. there was the hottest, sluttiest looking girl looking at me. i was so turned on.
Roger seemed to like what he saw too. telling me I was the prettiest girl he had ever seen. after a few drinks my inhibitions went and i told roger of my fantasy for cock in me, even two cocks. Roger told me how this was all normal and that being a pretty tranny i could enjoy those fantasies easily. sitting on the couch together, Roger put his hand on my knee. I knew almost immediately that Roger was going to have me, and i wanted nothing more than to be his little slut. i opened my legs a little and looked at him, half terrified.
Roger was a nice gentle teacher, he started rubbing my legs and then up to my hard cock, straining in the panties. he played a while then went down on me and gave me an amazing blowjob. i must have lasted about 30 seconds before i blew a massive load, Roger greedily gulped down the lot of it.
Roger place my pantied back over my cock, licked his lips then asked me if i would like to learn how to become a girl properly.
while we watched some porn Roger told me all about trans life, how a tranny girl should behave in fornt of a man, and etiquette like leaving your tranny cock in your panties unless the man takes it out.. a tranny is to act as a girl to her man and should offer her pussy to the man. she taught me lots of other stuff like safe sex and stuff.. anyway i started losing track as I was becoming aroused again by the porn and I knew that i wanted to lose my virginity today. I asked Roger and he said he would love to.
Roger leaned back and showed his bulge in his shorts, motioning for me to touch. I rubbed, and Roger took his shorts and his panties (hehe), revealing a 9 inch cut and very hard cock. I remembered Rogers instructions for sex (Head job to warm up, then present yourself). I reached over and took a small lick of his cock head. it was all soft yet firm and silky. I took it in my mouth and stated sucking, as he had to me, after a short time Roger pushed me off.. I dont want to blow yet, he said. I straight away got down on my hands and knees on the carpet and slid the Gstring to one side. Roger kisseed my cheeks and slowly got closer to my rose, finally licking my rose. this was the hottest feeling and i squirmed and giggled.
Roger fingered me for a while then finally rose up behind me, lubed himself up, then offered me a sniff of a little bottle he said would relax my ass for sex. te poppers ran through my body, making me instantly feel 100 times more sexy. know i begged him "Fuck me please". Roger pressed his lubed cock up against my hole. telling me to relax and i played with myself to keep myself hard. he slowly pushed and then suddenly his cockhead was inside me. WOw it hurt a bit. but he told me to expect that a bit. i buried my head down into the carpet as he grabbed my hips and pushed hi 9 inches slowly into me. this was the feeling i had been waiting for, finally my pussy was being used for cock. my own cock strained i was so horny, Roger started fucking me slowly.
before long Roger was fucking me hard, his balls slapping against me, this was more of a turn-on, and without touching myself i started cumming all over the carpet, some of it on my hand, which i quicly licked off. Roger came too, Filling me full of cum.
Now I felt like a real hot slut.