In the last year or so, I have started to seriously entertain the notion of having sex with men. I am primarily interested in anonymous, safe encounters with older men. Recently through craigslist, I found a man named John who is 52 (I'm 25), D&D free, single, and apparently very well versed in the gay casual sex scene. I've since contacted him via email and phone, and he seems sane. This would be my first gay encounter, and, as you might imagine, I am having some doubts.
John is adamant about making out, while I'm not sure that I'd be able to do it. The thought does not revolt me but does not especially appeal to me either. Am I making too much out of this?
As to my interests, I would like to be fucked aggressively while I lay on my stomach. John is 7" and thick. How feasible would it be for my virgin butthole to take him?
I want to do this but guess I am looking for a bit of reassurance. What, in your opinion, would be the most awkward part of this encounter?
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