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Topping the Teasing Bottom


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Many years back I had a friend with benefits and he'd buy the weed and I the booze. We'd lay back, listen to music, talk shit and eventually when he was ready we'd have sex. This was back in the days when HIV would become AIDS, there were no good and/or inexpensive medications and it wasn't clear if HIV was a long term manageable disease or something that might be fatal within a relatively short time. So, we would both usually use condoms with each other; it's just how things were.

Anyway, if he got high enough on weed he'd beg to be fucked. In those days I didn't top that often (and he was one of the first I topped) and condoms generally killed my erection. But he'd get me so turned on that I'd be able to top him anyway. That said, the ass hole - pun intended - would often let me get in and then complain it felt like I was stabbing him and usually I'd stop, we'd drink and smoke more, fall asleep and I'd wake him up by fucking him rubbered.

This night, though, I'd gotten in and he started complaining and I just took my dick out, took the rubber off and then stuck myself back in. "What are you doing?" he asks, and I just say, "Fucking you." And I did. Did I mention I rarely cum if I have someone's legs over my shoulders? Well, this time I could and I didn't last long. His ass always felt great wrapped around my dick and he was obviously enjoying himself; I still wank to the memory to this day.

Afterwards he complains he doesn't usually take risks; I fall asleep.

I let him bareback me in the morning and as far as I know neither of us caught anything that night & day at least.

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I had a friend who was like that - he usually topped me, but the bottom urges were strong in him and he would often beg me to top him. I only managed to fuck him twice, the other times he complained and said my dick was too big and he couldn't take it. 

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