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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