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I was about 25 at the time and wasn't really getting much sex. My wife was away and my sister in law that I was fucking was with her so I was left with not a lot of options.
I had been on a night out after a day at the races where I was about £300 up from gambling. We were in a nightclub and I got talking to a lass that just wasn't really that interested. She was a pretty little thing, she had a young daughter and was on a rare night out.
As the night went on I got drunker and hornier and made a joke saying well if you don't fancy me how about you make some money out of it. She joked and said a grand. I replied sorry only got £300. She laughed and said OK. I said but I want the while night. She said fine saves me a taxi ride.
She came back to my place and I got her to do a strip for me. Throwing tenners at her as she took her clothes off. We had a few more drinks and she loosened up a bit, we kissed but it just wasn't great so I pushed her to her knees and she took the initiative and started sucking me. She was awful at it so after a few minutes I pulled her back up. She made me put on a condom and I bent her over the arm of the chair. She had a cute little ass and I put a big red hand print on it as I fucked her from behind. Didn't take me long to cum as I was drunk and she was quite tight.
I said I wanna fuck your ass without a condom. After a lot of convincing she let me and told me I was the first guy to fuck her ass. I took it gentle and spent a lot of time eating her into it. Eventually I was right inside her and proceeded to finish myself off inside her ass. It was so hot watching my cum drip out of her ass and she got so worried it was gonna end up in her pussy.
I let her clean herself up and over the next few hours we fucked a few more times and I took some photos of her. I never got the film in the camera developed but still have it. I doubt it would be OK now anyway.
Later that morning j called her a taxi and she took her money and went home. Saw her out a few times and she kind of just looked the other way. It wasn't great sex but it was what I needed in that moment and cost me nothing because I won the money.
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