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Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and jacked-off over other men. So when my girlfriend told me that she wanted to fuck my ass with a strap on, I was interested. I was at university at the time but was home for the holidays. I only come home during the holidays, so at first both me and my girlfriend were super horny for each other. We'd have sex all the time but after a while we both got a bit bored of normal sex. She seemed to notice that I wasn't that keen on it, partly because I had been jacking off over gay porn behind her back. She therefore thought it would be a good idea that we try something new."What would you be into?" I asked her, not really sure where this was leading. "Well, there is this one thing I read about online... It kinda excited me but really not sure if you'll want to do it." I told her to just say it, so blushing she asked me "have you ever heard of pegging?" No, what's that?" I replied.. We sat in the front seats for a while, while we nerved ourselves up. I assured her I would just eat her out, and this didn't constitute a new relationship, it was just two horny people taking care of each other's problem. She suggested going downtown for some pot, but not being a smoker, and not having any cash for pot, I didn't want to do that.After quite a while of talking, Leslie made a comment about being uncomfortable, and took her bra off, from under her tee shirt. A more experienced man would have realized that was the turning point, but I was still trying to figure out how, or if I was going to get lucky. Who knew?An agonizing period of time passed, and she finally said, "Okay, lets do this." and moved into the back of the van. My van, I should mention, used to be a utility van for the phone company. It was not a passenger van.I found a scrap of cardboard for Leslie to lay on and flattened it. We slowly stripped, we were both too gun shy to just strip while the other was.
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