If you start exploring the world of gay sex, you can’t avoid that moment when a guy starts taking an interest in your anus.
During my previous sexual escapades, I had managed to avoid any anal contact. Guy #4 however wanted to do that thing that gay sex is commonly known for. Even scarier, he wanted to do it to me.
The thing is, while I knew most gay guys like anal sex, the concept never played a role in my secret fantasies my ‘straight self’ felt guilty for having. For a long time I had convinced myself I couldn’t be gay because I had no interest in sodomy. Even in my gay head a vagina seemed way more comfortable, for everyone involved.
Yet I also knew I enjoyed exploring my own sexuality. At 24 years of age it was a much needed exercise. All in all I met four different guys through a paid phone service. The fourth one was by far the nicest, most honest and most experienced. He would be the one to finish this chapter and… well, take my virginity. For real.
Not to offend any gay rights movement, but unless you’re a turkey, an asshole is not made to insert things. It just isn’t. Just because you can, doesn’t mean that’s its function. As I was being definitively devirginilized, I couldn’t imagine how anyone could enjoy anal sex. I tried to ache my way through it for about half a minute and then suggested we’d retreat to doing other stuff.
Guy #4 didn’t mind. And apart from those thirty seconds of horror I actually had a really good time with him. He would become the first person I ever spent a night with.
In retrospect, spending the night with someone was much more relevant than those thirty seconds. Still, for the first time I found myself empathizing with people who consider anal sex a good idea. To inflict joy and pain simultaneously creates an extremely intimate tension. And seeing as relationships are basically about inflicting joy and pain, it did seem natural something like that is reflected in the sex.
But I guess I wasn’t ready to embrace any of that, not yet anyway.
Next morning my sex date woke me up by putting his arm around me. I had never woken up like that, so at first I was surprised, followed by pleasantly surprised. It was nice to be awakened by such a nice gesture.
Guy #4 didn’t rank too high on attractiveness. Nevertheless he was the best sex I had ever had, up till then that is.
Unlike my previous guys, Guy #4 was out of the closet. He seemed okay with being gay. That sense of comfort must have reflected itself in the sex, save for those thirty seconds of course.
But I did feel conflicted. In my head I was still just a bicurious guy doing other guys to get at least some sex. It was supposed to be just about sex, not intimacy. I couldn’t get myself to like the fact I was liking this so much.
Also, as we woke up together Guy #4 told me he had completely fallen in love with me. He said it kiddingly, or at least I think he did. I honestly don’t remember how I reacted, but I imagine it must have been distant. His use of the word ‘love’ was probably the main reason I didn’t see him ever again.
That’s a shame, because Guy #4 had just given me the biggest compliment anyone had ever given me, not to mention the best sex I had ever had. I should have given him credit for that.
Thank you, Guy #4.
Relationship summary
Length: ± 10 hours
Format: A loving sex date
Sex score: (0 being an Oprah moment and 10 being the best sex ever): 5
168guys.com 
I guess it takes getting used to it, my first time was horrible.
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It would seem persistence is the key to any part of a relationship, even the sex;)
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