I did this, but it wasn't a blackmail situation. It was just fun for all involved.
My GF and I put up an ad on craigslist looking for a girl. I had done this before with other girls and didn't expect to get any response, really. Craigslist is great if you're a single girl looking for a guy, or a couple. But it sucks for couples of guys looking for girls.
To my surprise we had our first real person respond in less than an hour. She was a self-described butch lesbian who wanted to be with a guy because she never had and was curious. She said it was "on her bucket list".
My girlfriend had never been with a girl, and this girl had never been with a guy.
We all got together that night at a hotel about half way between us. The two girls had some drinks and got high. I had a drink or two. Spent like four hours or so playing around. Lots of oral between the three of us, and finally after an hour or so, I remember her asking me to fuck her.
I asked if she was sure and she certainly was. I asked if she ever played with strap-ons or anything before and she said she did. So I asked her what positions she liked best for that. She said she liked to be taken from behind.
So I got behind her and rubber my cock against her pussy. She was soaking wet. We'd already been playing for a while and I know she came a few times already. But she was also incredibly tight. The tightest I've ever been inside of. Probably because she was so tense and nervous about this...
I still remember sliding into her. Her face was down on the bed with her ass up in the air. Her head was to the side and I could see her face, and the way her expression changed as I slid in was amazing. She let out an "oh my god" sound and some moans, and I think she was just honestly surprised at how good a cock filling her pussy would feel.
I fucked her for a while. And my GF, and we took turns eating the girls... finally they both got the idea that they wanted to finish me off "porn style" and suck me off together so I'd cum on both their faces. I was happy to oblige.
We got together maybe half a dozen times over the next month or two. Finally I think the lesbian started to feel guilty about cheating on her GF and we stopped.
I do have pics and some I think my GF took video of me fucking the lesbian. I'll have to look for those. She's not much to look at, but the scenario is hot.
