If you want to stay safe, this conversation is an essential first step, not something to get out of the way. Something all three places-and others like them-have in common is that they’ll probably be able to give you a more nuanced idea of the incredible variety of ways people mitigate the risk of sexually transmittable infections. One last thing: If there’s a Planned Parenthood in your area, or assuming you’re a legal adult, a BDSM or swingers’ organization, you might consider asking for resources from people who want practice navigating these conversations.
Start with something like, “I care about sexual health, and I want to do this as safely as possible.” If you have something to disclose, you can say, “I need to disclose something about my health and give you time to think about it.” Share your boundaries as clearly as possible, and listen to theirs. Have the discussion before things have gotten too hot and heavy.
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In terms of how to actually broach this conversation, pick a time where you’re both sober and can communicate clearly. For one thing, you care enough about it to ask a stranger for advice regarding it, and for another, from what I understand, these kind of toys can be way more pleasurable for women (and their clitorises) than for men (though certainly, they get the extra stiffness that the cock ring component provides). But if you are genuinely curious and hung up on this thing for practical reasons (and not merely the principle of it burning a hole in your underwear drawer), I think it’s up to you to bring it up. If your weekly routine is indeed perfectly enjoyable, surely this added stimulation isn’t needed. Except it’s coming from your underwear drawer and it really is making noise because you knocked it on the last time you were getting dressed. Right now, it sounds less like a fun prospect and more like something that is haunting you like a tell-tale heart under the floorboards. People don’t procrastinate stuff that they actually want to do. I think what it means is that neither of you are that interested in using this toy. Is it wise to bring this up with him, or should I just let it go? Again, I know I am dumb. The other roommates have asked me if I’ve noticed him acting strangely. He’s not hostile, but he won’t really look me in the eye either. A month later, I now hear him having loud sex with women regularly, which I definitely never heard before. I was totally fine with it, and he acted like he was too, but it’s clear he’s not. I am the only gay guy (seemingly!) in a shared house of five guys, and this was very much unplanned. I am the guy who did the stupid thing from a hundred overheated online stories: I slept with my straight roommate when we were both drunk. Send your questions for Stoya and Rich to.
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