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I had a beautiful girlfriend and could have had any girl I wanted. Unbeknown to her and my friends, I was a closet crossdresser, a sissy who fantasised about dressing up and sleeping with guys. It was a confusing time for me, I was almost certain I was straight but part of me craved cock, especially when I was crossdressed. I would dress all sexy in my own underwear and sisters clothes (I was lucky to have an older sister so access to a full wardrobe) and play with myself until my cock was sore and balls empty - I would fantasise about being with a guy and this would drive me to orgasm every time. I always managed to suppress these feelings but when I was horny they would always resurface. I had a large selection of porn, all magazines as it wasn't as easy to get hold of videos back then (no internet and certainly no xhamster!), I had a good mix of magazines, female, tranny and gay but I wanted videos, I needed to see guys having sex, I wanted more gay and tranny porn but videos this. I was scared, more because I didn't want her parents coming home or grandma walking in, the front door was unlocked but you could hear someone opening it from her room so it was whatever. I slipped my penis inside of her and I could tell you how amazing it felt, warm,wet,tight! So erotic. She was laying down on her back with me standing up, crouching over her and slowly fucking her. She said it hurt a little so we took it real slow, slow was good, slow was amazing. We had been fucking for 10 ish minutes, we didn't go position crazy and try a bunch of things, doggy style was majority of the time, and her riding my dick while I was laying down, which honestly that felt the most amazing to me.Now the worst fear for someone is the condom breaking, it did on us our first time.. It ruined the moment Completley and I was so selfish and stupid about it, I didn't stay long after that. I JUST unloaded into her when I thought id check the condom because it didn't feel like my cum stayed within.
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