Straight Male / 30
Best Friends Sister
First confession, I've got a few but this is a fond one in some respects.
Growing up I had a really good mate of mine in school, both our parents divorced around a smililar time so we related a lot and I'd spend more time chilling round his than at my own home, we played football. play video games at his, chat about girls, get beers for the weekend. The usual teenage guy shit.
He had a younger sister who was my younger brothers age, they even dated when they were young (pretty innocent shit at the time) - I was really tight with their whole family, him, his mum, his brothers and sister, I used to give her books and chat about literature, history, philosophy, she was quite intellectual which I liked as I'm quite a nerdy guy.
But him and his sister didn't really get on at the time and he was super protective of her. As we all got older towards late teens, she got inreasingly hotter, she was thick, in a good way and her best asset was her ass. I used to look at it and jack off thinking about it at times, but just a fantasy. Things changed when my mate had me and his friends round and she wore increasingly revealing shit, or hot pants with a thong or g string on display. He understandably hated it. None of us as his friends every said anything, but we were all thinking the same thing.
It was always just a thought, never actively seeked out, till one night she started texting me. She only lived up the road about 20 minutes from me, texting turned to flirting "I've always thought you were hot" type shit from both of us. We decide we want to have a drink and get high, so I invite her over, its coming up to midnight.
We drink, we smoke, then we fuck. People always say "we went all night" but this is one of those few occassions of non stop sex all night long i've had, pure lustful teenage stamina I guess. I came 4 times across 7 hours with some joints in between. She loved it from behind, fine by me, a perfect view of that ass. I can still visualise sitting back with a joint as she rode me reverse cowgirl, having cum twice already, then pumping her doggy with another load. - We both skipped 6th form & work the next day, had a sleep in, then over to hers all afternoon for another 3 hours of fun in the empty house.
This continued at every chance we had for about a month, their mum worked nights and my mate happened to be doing a work placement so was out of town several nights a week. It got to the point she was missing so much college that she got pulled up on it, her mum turned up round my house asking my mum if she had seen us and shit. Then the night after a party one of the older brothers walked in to find me asleep in her bed. Understandably shit went down.
I wasn't welcome round anymore, got completely cut off and not allowed to see her. About 3-6 months later (I forget the timeframes) was the night I left town and moved away over 10 years ago now, I visit fam but haven't lived there since. She came over to say goodbye and we had one last night of forbidden fun togther.
I still think about her sometimes and maybe if I had gone about it differently it could have been something more, maybe I'd have been part of the family that took me in. But such is life, feelings were there, and I also felt bad for fucking over my mate, it looks worse than it was. We both wanted it. But it was a forbidden thing. Maybe thats why it was the hottest fuck buddy experience I've had. And damn. I still miss that ass.
Growing up I had a really good mate of mine in school, both our parents divorced around a smililar time so we related a lot and I'd spend more time chilling round his than at my own home, we played football. play video games at his, chat about girls, get beers for the weekend. The usual teenage guy shit.
He had a younger sister who was my younger brothers age, they even dated when they were young (pretty innocent shit at the time) - I was really tight with their whole family, him, his mum, his brothers and sister, I used to give her books and chat about literature, history, philosophy, she was quite intellectual which I liked as I'm quite a nerdy guy.
But him and his sister didn't really get on at the time and he was super protective of her. As we all got older towards late teens, she got inreasingly hotter, she was thick, in a good way and her best asset was her ass. I used to look at it and jack off thinking about it at times, but just a fantasy. Things changed when my mate had me and his friends round and she wore increasingly revealing shit, or hot pants with a thong or g string on display. He understandably hated it. None of us as his friends every said anything, but we were all thinking the same thing.
It was always just a thought, never actively seeked out, till one night she started texting me. She only lived up the road about 20 minutes from me, texting turned to flirting "I've always thought you were hot" type shit from both of us. We decide we want to have a drink and get high, so I invite her over, its coming up to midnight.
We drink, we smoke, then we fuck. People always say "we went all night" but this is one of those few occassions of non stop sex all night long i've had, pure lustful teenage stamina I guess. I came 4 times across 7 hours with some joints in between. She loved it from behind, fine by me, a perfect view of that ass. I can still visualise sitting back with a joint as she rode me reverse cowgirl, having cum twice already, then pumping her doggy with another load. - We both skipped 6th form & work the next day, had a sleep in, then over to hers all afternoon for another 3 hours of fun in the empty house.
This continued at every chance we had for about a month, their mum worked nights and my mate happened to be doing a work placement so was out of town several nights a week. It got to the point she was missing so much college that she got pulled up on it, her mum turned up round my house asking my mum if she had seen us and shit. Then the night after a party one of the older brothers walked in to find me asleep in her bed. Understandably shit went down.
I wasn't welcome round anymore, got completely cut off and not allowed to see her. About 3-6 months later (I forget the timeframes) was the night I left town and moved away over 10 years ago now, I visit fam but haven't lived there since. She came over to say goodbye and we had one last night of forbidden fun togther.
I still think about her sometimes and maybe if I had gone about it differently it could have been something more, maybe I'd have been part of the family that took me in. But such is life, feelings were there, and I also felt bad for fucking over my mate, it looks worse than it was. We both wanted it. But it was a forbidden thing. Maybe thats why it was the hottest fuck buddy experience I've had. And damn. I still miss that ass.
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