Hi Dan, huge fan. I'm a straight male in my late 20s. I've found myself in a situation that I never would have even considered before I started reading your column. I met a girl on Tinder and after arranging our first date, she admitted that she's gay and is in an LTR with a woman. She's a college student in her early 20s and has never slept with a guy before. She says she's gotten permission from her girlfriend to have sex with a man because she's curious what she may be missing out on. I'm open to this. It's a good arrangement for me, but I don't want her to get into something she'll regret later. Honestly, I've always been attracted to women who look "butch" so this is pretty hot to me (maybe that's clouding my judgment?). I don't have any plans to turn her straight, but I do want to make sure everyone has a good time. Is this even a good idea? If so, what can I do to make the experience as comfortable and as fun as possible?
Wanted A Date Didn't Anticipate A Proposition
A straight boy sleeping with a curious-about-cock lesbian on a hall pass?
This is the sort of thing we hear about when things go spectacularly wrong—when the "curious" "lesbian" winds up dumping her girlfriend for the dude she hooked up with on that hall pass, when it turns out the girlfriend didn't give her SO permission to sleep with some dude (and the girlfriend finds out), when the lesbian gets pregnant or contracts some other sexually transmitted infection, when the dude
catches feelings for goes full stalker on the lesbian who, curiosity satisfied, just wants to be with her girlfriend now, thanks, but the dude refuses to fuck off and then there are cops and restraining orders and self-defense classes.
Yeah. When something like this generates drama, breakups, heartbreak, infants, and court orders, we hear about it.
But when something like this goes right—when the lesbian doesn't run off with the dude, when the girlfriend back home did give her permission (or never finds out*), when the dude doesn't
catch feelings for go full stalker on the lesbian, etc.—we don't hear about it. Butch lesbian meets up with game straight boy, they have some mutually pleasurable/mutually transgressive sex, and then part ways, grateful to have found each other but neither feeling a need to seek each other out again. And while they'll always remember each other (and the hot sex) fondly, they won't speak of each other much, if at all. The lesbian, not wanting to have her lesbian bona fides challenged, isn't going to tell her lesbian pals about that one time she sat on a cock had PIV intercourse with a cool and respectful straight boy; the straight boy, being the cool and respectful type, isn't going to run around bragging to anyone who'll listen about the hot college dyke he nailed that one time.
So, yeah, when something like this goes very, very wrong, we hear about it; when something like this goes very, very right, we don't hear about it. Consequently, WADDAAP, our frame of reference is warped—we believe a sexual adventure like the one you're contemplating is fated to end badly because the ones we've heard about all ended badly.
I think you should go for it—if you can be cool and respectful, if she can articulate her desires and interests, if her girlfriend is really on board (and you'll probably have to her word for it), this could go spectacularly right.
Some practical pointers...
To make sure the experience is as comfortable and as fun as possible—and to make sure it's fully/enthusiastically consensual and mutually pleasurable—you're gonna need to have a couple of long convos with this woman about what she wants out of this experience. (Protip: have these convos right after you've masturbated, WADDAAP, when horniness is less likely to cloud your judgement.) Your desires and fantasies should be part of the convo too—you're not a sexbot—but since she's the one stepping outside her comfort zone here, WADDAAP, her desires and interests need to take priority. Remember: just sleeping with a dude is a reach for her. She's fantasized about it, but sometimes reality dredges up unexpected feels—you don't want to risk complicating things further by asking her to do something for you that isn't on her list. So ask her what she wants to try, identify the things she wants to try that overlap with your own desires, and commit to doing only those things.
You're also gonna need to talk about birth control before the hookup, of course, and you're gonna need to check in regularly during the hookup. She might want to take the lead or her fantasy could involve being taken by an aggressive man. If that's the case, WADDAAP, only "take" her in the ways she wants to be taken—no improvising, no introducing something that wasn't negotiated in advance. And agree in advance that either of you can call for a timeout, when needed, or call the whole thing off with no hard feelings.
Finally, WADDAAP, if she can't freely converse with you over the phone or over coffee or over email about what she wants, if she can't clearly articulate her desires, don't go through with this. Going into this flying blind—going into her flying blind—all but guarantees that this'll be one of those straight-boy-sleeps-with-curious-lesbian-on-a-hall-pass hookups that we all get to hear about.
* Cheating shouldn't be filed under "goes right," I realize. I'm rounding up here.