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Simon

Age when it happend: 21
Where it happened: My former house
Langauge: English
Sex: Male
Rating: 5
Category: Straight

I had never had a girlfriend before Sam. I’m not the most social of characters, though I have lots of friends. I’m the type of bloke who falls deeply and madly in love with girls, completely and utterly, and ends up being the “just-good-friend.” Which is great, I have some really close female friends and I wouldn’t change it for the world.

But I’d always wanted something more. For all of my apparent confidence at parties and social occasions and the like, I’m not at all confident when it comes to women. I noticed this at 16, the age of consent here in England, when everyone in school were shagging like rabbits. The older I got the harder it was – purely because I knew that the girls would be experienced, and I wasn’t.

I have this thing, in certain aspects I’m really not selfish at all. And sex is one; my main worry wasn’t that I wouldn’t be able to do it or anything like that, it was simply that I would be a disappointment in bed.

I met Sam through a friend. She was everything I wanted – cute, artistic, played guitar. I loved her eyes. We went for a day trip somewhere and we kissed over a couple of tequilas. From her conversations I got the impression that she was fairly experienced with sex, and this got me worried. I eventually told her of my virginity, and she was surprised, because I “didn’t act like a virgin.” Whatever that meant.

One night, we had the house to ourselves. We started kissing passionately on the living room sofa, and as was usual up to then, our hands started wandering. She caressed the bulge in my jeans, and I was stroking her nipples through her shirt – this always turned her on, she was very sensitive. I moved my hands down to her clitoris and she changed. She took off her shirt, and took off mine. She took a cock ring out of her bag, and put it on, telling me it would prolong the time it took for me to cum.

She slipped the condom on and pushed me back onto the sofa. She took off her panties and straddled me, tentatively slipping my penis inside her. All the while I was kissing and sucking her nipples, and even using my fingers to stimulate her clit whilst she was straddling me. I don’t know whether it was that, the cock ring, or just our combined horniness, but we came simultaneously around 10 minutes later.

As far as first time goes, I’d say that wasn’t a bad one. We broke up 4 months later.

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