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My gay boyfriend had actually been in a few situations with other men in his younger years. He also experimented with a lot of drugs during those years and he claimed that the two were linked, that the whole thing was one huge exploration/rebellion and he always knew he could never have satisfactory relationship with a guy.
But yeah, he was like your guy, case--couldn't get it up, couldn't keep it up, couldn't come. We only tried maybe once a month, and were only successful maybe once every 3 months. It got a lot worse after we had a talk about it at some point and I told him that "the sex wasn't important to me," meaning that it wasn't how I judged the relationship, trying to make him feel less insecure about it--but he must have decided it meant I didn't like sex or didn't find him attractive or something, because things just went downhill from there.
The other really awkward thing was that he had never been broken up with, ever. He had always been the one to end his relationships--and he brought this up, to me and in front me, all the freaking time. He was proud of it. I actually felt bad for his ego, and gave him plenty of time to take the hint and break up with me first, but it never happened. When I finally broke up with him, he wrote it off as a nervous breakdown on my part (a role I admit I played up a bit because, like I said, he had self-esteem problems and I genuinely felt bad for him) which he of course was very understanding about because he had had them before.
Looking back, I don't really regret the relationship, I certainly had worse ones... the whole thing is just kind of sad to me.
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