Sleeping Around

By | October 31, 2011

I’ve never thought of myself as a thrill-seeker. I’ve never gravitated towards dangerous sports or deliberately sought out risky situations. At least I used to think that.

Thinking back now I believe I have identified four occasions where I deliberately put myself in risky situations. The common theme is that they all involved women. Two of those were where the respective girl’s father’s didn’t approve, in both instances not because of my reputation – sadly I didn’t have one LOL – but for other less valid reasons.

The other two cases were because the girls I went after were already involved. There may have been more but I don’t remember them. What I do remember was that around the same time as my pursuit of the girl I’m going to write about another girl was absolutely throwing herself at me and I really wasn’t interested. More fool me, because she was a very nice girl. Perhaps I just wasn’t attracted to nice girls.

And that is why I’ve titled this post “Fucking His Girlfriend”. One final thing, I’ve just remembered a third occasion where I went after someone else’s girlfriend … Ooh I’m a bad boy.

It was late summer, early autumn. We were both in the upper sixth and her name was Mandy. Well it is for the purposes of this account. I went to school in a large village. The comprehensive school I attended still felt like a grammar school despite the influx of new and idealistic teachers. It had a large catchment so you tended to mix with girls from villages that you’d never meet otherwise, from villages miles away.

Mandy and I were out after school. We’d been rehearsing for a school production and were walking home together in a round-about way. We enjoyed each other’s company but as friends. I thought that was all she wanted, though I had different ideas. Not surprising, teenage boy, bright, bubbly, friendly girl with a lose perm and nice tits. There’s only one place my mind headed every time I thought about her …

Because I thought she wasn’t interested and knew she was already involved I kept things at a platonic level. Except I hadn’t. It was probably a combination of the lingering looks I kept giving her the pregnant pauses that seemed to become increasingly apparent in our conversations as things were left unsaid and the occasional joking sexual remarks I made that made it plain to her I was horny as hell for her.

It happened when we were sitting on the dry stone wall behind the church. She caught me staring at her and for once I didn’t pretend I hadn’t been. I kept looking at her grey eyes. She put her hand on top of mine and leant forward, eyes shut, lips expectant. It was very, very innocent.

I hesitated. This wasn’t supposed to happen, she was already with someone, she had never been interested in me. Yes I admit it I was naïve she had been thinking about me for a long time but not likely to deliberately two-time her boyfriend. Quite how long she had thought about me or how much she had wanted me I never found out because despite of what happened next we never talked about it. And until this post the only person I ever told about it was Suze.

The kiss told me all I needed to know about her feelings. We slid off the wall and hidden from view got involved in a long and grope-filled clinch. She didn’t mind my wandering hands, in fact she seemed to welcome them. Maybe it was the waiting that made both of us abandon caution.

Before I knew it she was struggling to sit up and removed her bra, which she did in that magic, without talking her sweater off sort of way that men find so amazing. She slid it out of the left arm of her grey pullover and dropped it on the ground. She lay back down beside me where I resumed my fondling of her breast, unhindered.

Her nipples where hard, almost as hard as my cock. She held it through the black denim of my jeans, gently rubbing, her nails scrapping against the fabric.

Her fingers started to scrabble at the button on my waistband. I helped her out, it was after all the gentlemanly thing to do. Then, in a very un-ladylike fashion she yanked at my trousers and underwear until they were round my ankles.

“Please screw me.” She asked. I smiled, not at the thought of the totally unexpected and much longed-for shag, but the fact she referred to it as screwing. She always did refer to sex as screwing, not sex, or shagging, or fucking. Screwing.

I helped her peel back her tight blue jeans and pink panties. She removed them both completely. Then she straddled me. She rubbed herself along the length of my cock, not to arouse me but in an effort to guide me into her pussy. I was incredibly aroused, but inexperience on both our parts meant the angle was wrong and she had to reach down and guide me inside her.

Mandy bounced up and down for a few minutes, enjoying my hands cupping and squeezing her breasts under her sweater. We both wanted to feel me fucking her, that was obvious, glorious though it was with her riding my cock, curly hair catching the late afternoon sunshine. We both needed to feel me fucking her.

We rolled over, managing to keep my cock inside her, just. The screwing began in earnest. Until I started to think about this I had forgotten how innocent it was. Almost devoid of technique but full of enthusiasm I pumped away, encouraged by the appreciative moans and squeals she emitted. I remember her hair spread behind her head on the grass, eyes closed, mouth open.

I felt her pussy tighten on me and simultaneously become suddenly wet. Her moans got louder, had I not been approaching orgasm myself I would have probably worried about someone hearing us. But I was cumming and did so with a sense of such immense satisfaction that I was probably grinning from ear to ear as I rolled onto the grass beside her.

About a week later I was stopped in the street by three guys, all around my age. They blocked my way on the pavement and made it plain they had something to tell me. I can’t remember the words they used but the meaning was “Stay away from Mandy. Or else!”. She had obviously hadn’t told her boyfriend exactly what had happened, but must have mentioned me a little too often. I brushed them off with a “Yeah whatever” type of attitude, which seemed to disarm the situation more than perhaps a flat denial of any wrong-doing would have done.

Looking back it could have gone a lot worse, or maybe a lot better. I wonder what she’s doing now?