How i became a Transexual Tart.

This is my true story of how i became a Ladyboy. I grew up in a small town in the UK, Where i lived there wasnt many females in the same age group as me and my friends most of the girls were much older than us which left the boys sexually frustrated alot of the time. My best friend Alan was always frustrated and would always find an excuse to touch me or show me his cock. One day when we had the house to ourselves we had some alcohol to drink and we watched a porno together, Alan got very hard and started to stroke his cock in front of me, i told him to put it away but he had other ideas. He came over to where i was sitting and started to rub his hard cock all over my face, i didnt say anything except giggle nervously. He took this as a sign that i was enjoying his cock being rubbed against me and started to push his cock into my mouth, it was the first time i tasted cock and i liked its salty taste and sweaty smell, i started to lick all around the hard bell end and dipped my tongue into his pee hole. He was moaning quite loud by now and grabbing at my hair quite roughly, i told him to please go easy, he then asked me to go to the bedroom with him which i did, He told me to get naked and get on all fours which i nervously did but i was also excited because i knew what he wanted. He got behind me and started to finger my arsehole with a wet finger then two and three fingers went into my arse, i felt so bad and a bit embarrased that i was on display to Alan so easily. It was then that he asked me to go to my mums room and put her clothes on, i was quite shocked at his request but i got up and went into my mums room and opend her cabinat, Alan was beside me and told me to put on her knickers which i did, then he asked me to put a pair of tights on which he found in the drawer, i put the dark tights on and i felt quite good and i wanted to please him, next he had me put on a black dress which he got from the wardrobe, i put it on over the tights and knickers that i had put on for him, he then told me to put her makeup on which i did quite well as it was my first time. Alan then grabbed my bum and told me to get back on all fours on the bed which i did. He took some fotos of me first then he got behind me and lifted my dress up to my back, then he grabbed at the tights and knickers and pulled them down to my knees, i heard his zip come down then i felt him nudge his cock between my bum cheeks, next i felt my arsehole being spread open by his cock and a very sharp burning pain and Alan was inside of me pounding at my arse. he reached around and started gropeing at my nipples as he fucked me really hard, i heard him shout something snd he tensed up and i felt Alan shoot a massive losd into my arsehole. We lay there for a while then i got dressed back into my boy clothes but ever since that day i always dressed up for Alan, i was his cum dump Tranny and i loved it. I think i may have loved him too until he had to move away....
10% (6/55)
 
Categories: AnalFetishShemales
Posted by cinderella88
4 years ago    Views: 3,077
Comments (12)
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2 years ago
Great first time
thanks
Jay
3 years ago
nice
3 years ago
mmmm great story
3 years ago
great story
3 years ago
nice
csng69
retired
4 years ago
hot
rafael0058
retired
4 years ago
Great story hope you keeped that relationship going for a long time thanks
4 years ago
Almost the same as with me...
Kisses from Paula
4 years ago
really good story I hope you write more
4 years ago
very horny,you little slut.
4 years ago
nice story
4 years ago
Great Story