My new boyfriend is into cuckolding. Some previous boyfriends have expressed interest in seeing me with other men, but not to this degree. Also, I’ve thought about being in this sort of sexual situation, but never really felt as though the others were truly OK with it. But this guy has detailed fantasy scenarios, such as my going on dates with other guys then coming home and telling him about it; he even fantasizes about my becoming pregnant for another man. I’ve told him I am willing to have sex with other men, but it must be with protection. He says he’s thought about this for over 5 years but never fully acted on it, except for watching one of his exes perform oral sex on another man. I’m not afraid to participate, but I just don’t know how to go about doing it so as to make it really good for him; how should I act and what should I say during the scenes?
Since you haven’t been with this guy for a long time yet, it’s important that you feel him out so you can get a good sense of how seriously he’s committed to living this fantasy. What I mean is, some men have desires that excite them very much when they’re horny, but then once they climax they feel very ashamed and guilty. Does he talk about the fantasy even when he’s not really aroused, like after sex? Because if he does, that’s a good sign it’s not something he’s ambivalent about. The reason that’s important is that you don’t want to get involved with this kind of thing if he’s going to be excited by it at first, but then use it to attack you whenever you have an argument. I suggest taking it slowly; talk about the fantasy and find out exactly what he wants, then go in gradually. I think it’s very important that the first few times y’all do it should be 3-way situations, with him present; if he seems to really enjoy it and he’s glad that it happened once your “date” leaves, then you can move on to the more adventurous things like seeing guys on your own and telling him about it. I think you’re very wise to insist on protection for the other men; guys often don’t consider practical things like that when they’re all excited by a fantasy. And that’s exponentially more true with the idea of getting pregnant for someone else: in these days of DNA testing, that would be a spectacularly bad idea for reasons I’m sure you don’t need me to explain.
I wouldn’t worry too much about the mechanics of the role-playing if I were you; he’ll probably make it clear what he likes, and I’m confident you’ll pick it up as you go along. Just take it slow, enjoy the experiences, don’t let him push you into doing things you feel are unsafe or that you aren’t quite ready for yet, and make sure you reserve the right to turn down any specific person he might suggest that you don’t want to go to bed with for whatever reason. That way, this will be fun and exciting for you as well, and will minimize the chances of building up resentments (in either of you) that could harm your relationship in the long run.
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