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A closeted guy told me he wanted to experiment with me. How should I proceed?
by Cait Robinson
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Dear Miss Information,
On New Year's Eve, I met a closeted bisexual guy in his thirties who told me that he wanted to try fucking a guy. As a twenty-something gay guy myself, this is a fantasy realized. What is the best way to navigate the situation? Should we discuss beforehand what he's comfortable doing? I'm quite a sexual person and would love to be able to play out some fantasies on a newbie. But I don't want to get into this situation and have him to freak out when it comes down to having sex. When we kissed on New Year's Eve, it was the first time he'd done anything sexual with another guy, and he was very keen. What to do?
I love that you are taking this guy's sanity into account, even if it's just for the sake of fulfilling your fantasy. It's a responsible and generous approach, and one we should all take with our partners, no matter how experienced.
It's a great idea to talk to him first to get a sense of what he expects/wants. You can also keep your antennas out for any hint of weirdness (i.e. any hesitation, nervousness, Republican senatorial affiliations, etc.). Better plans are laid while the clothes are on. This way, by the time you get into a dark room, you know he wants to be there and he knows you're looking out for him. That kind of trust will reap dividends.
When you're in the moment, keep an eye on him. You don't need to ask if he's okay every ten seconds, but get consent before anything big, and keep communication lines open and light throughout. Also stay tuned in to nonverbal cues. If you are afraid of overstepping bounds, let him take some agency: put yourselves partway into a position, then let him take the initiative on the last bit. You also may want to arrange a "safeword" if you don't think the standard "ow" or "wait, stop" will work.
Before you go in, be clear on how you will react if he panics, backs out, or otherwise seems hesitant. This possibility may be remote, but it is nonetheless a possibility. If he chickens out — explicitly or implicitly — it's game over. Under no circumstances should anybody be wheedled into a sexual act they are not prepared for, period. If you think it will be hard for you to respect this, or that the temptation to whine/beg/plead will be too strong, do both of you a favor and bow out now. Otherwise, you run the risk of being both his first and his last.