I have a friend who's 30 and only just coming out of the closet. I'm eighteen and I've been openly gay for a few years now, so I've been helping him along the way. There's one thing I can't help him with: he reckons he's a top and wants to try fucking me. I'm more than happy to let him try, and indeed we have tried, but as soon as he gets close to penetration he goes soft. He's very insecure in his identity as a gay man, and I'm almost certain this is an anxiety-induced performance issue. But what can we do? I've never topped so I can't help him.
New Gay Friend
Get your newly out gay friend one of these to practice on.
I'm completely serious, NGF. Your 30-year-old buddy might have an easier time building up to partnered sex—he might be more confident in his abilities/erections—if he went for a few rides in what amounts to an assfucking version of a flight simulator. (But do a little digging around online and see if you can't find a silicone one.)
What's his issue? I dunno. He may be distracted by concerns about your pleasure, NGF; he looks in your eyes, he sees expectation and excitement in them, he starts to worry about whether he'll be able to do it this time, he starts thinking about the last time he failed and... pfffft. His dick deflates. Or he may have some hangups about assholes and cleanliness. Or he may be worried about hurting you. Or he may have some other concern(s). Blowing a few loads in something that looks like ass but isn't—a couple of sessions with a partner (or a part of a partner) he doesn't have to worry about disappointing—may help him keep focused, cool, and boned the next time he's getting close to penetrating you.
And for the record: It's awfully nice of you to help your newly-out, much-older gay friend in this way, NGF, but letting a guy practice on your ass is... well, it's both a little dehumanizing (which can be hot) and a little above and beyond the call of duty/friendship (which can be nice). If you're into the guy, or into the sex, and you wouldn't mind getting off with him, well, okay then. You can keep playing Mother Bottom Theresa. But if you're not into him, if you're only letting him take these practice runs at your ass because you pity him, stop letting him fuck attempt to fuck you and share this link with him instead.
You can also direct him to this column about ass play for Beginner Gays. And the next time you two hook up (if there is a next time), NGF, tell him the sex continues whether or not he loses his erection. Because M/M mutual masturbation and oral sex aren't tragic consolation prizes, they're hot, hot, hot gay sex. And a few successful JO and/or oral sessions should help build his confidence too.
Also, maybe the friend only says he's a top because he sees that as less gay than being a bottom, which he fundamentally is but can't bring himself to accept just yet. I'd say he's still a few steps away from being totally at ease with his desires.
For some guys, being a top is perceived as more masculine and less gay. They can tell themselves that at least they aren't a swishy bottom, they are a macho top. A newly-out insecure gay may be very tempted by this logic.
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