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Dear How to Do It,
I’m hoping you can supply me with some guidance, readings, and maybe some comfort. Tonight, my fiancé told me about his main kink. We have been together for six years and are getting married in less than a month. It’s been a huge surprise and is sending me for a loop.
His kink is cross-dressing. But he is incredibly vanilla and has, to my knowledge, a much lower libido than mine. This has been one of the very few points of conflict in our relationship. Generally, I assumed sex once or twice a week at most was because of these discrepancies. I found out tonight that he’s actually cross-dressing while I’m out of the house and jerking off then. This is making me feel incredibly insecure and sad. It turns out that he would rather do that than have sex with me because we definitely aren’t having sex those days.
Also, I have been doing some online research and found that while many men who cross-dress are cis and heterosexual, there are so many horror stories of women whose husbands later come out as trans or gay and leave them. He told me unprompted that he has thought deeply about it and is cis and hetero, but I am terrified that this future we are planning together is going to fall apart and I would love some comfort or reassurance or advice. I am not really attracted to men in women’s clothing. I can appreciate it aesthetically, but it is not a turn-on.
Do you have any tips for getting more comfortable with it? What questions should I ask as I learn more about this and what this means for my partner? Do you have any reading recommendations? I want to make this work. I love him so much. He is the best part of every day. He makes me laugh and we have the best conversations and sex. I am the first person he has ever told and I want to make sure he feels supported and loved. We are not interested in opening the relationship at all, so I want to make sure he can feel his full self in our relationship.
Rich: I want to give our writer tough love here in certain ways. They approached us very kindly, but still, I do think that there is some kind of corrective guidance that is needed.
Stoya: I fully support that on this one. I think we are on the same page here.
Rich: Yes. What leaps out to me first is this paranoia when she asks what does this mean for our relationship? Does this mean I’m going to end up alone? She specifically used the phrase “horror stories,” which is like, OK, one person’s horror story is another person’s tale of liberation. I think that while I understand why such a revelation would cause concern, your partner can leave you at any time for any reason irrespective of their gender identity, sexuality, or the agreed-upon terms of your monogamy.
Stoya: Hey, I’m going to go real morbid here. You could find the straightest, most vanilla guy in the world, and even if you keep him on an entirely vegan diet, and he never smokes cigarettes or does stimulants, he could still have a heart attack on top of you at age 50.
Rich: Totally—he could get hit by a car. I mean, the risk you take when you love, when you connect with somebody on that level, is that they might not be around five minutes from now. We persist because love is worth it. So again, it makes sense that this fear has been stoked by this situation, but a dissolution of the union is always a possibility. Really our writer has it in some ways no different than anyone else just in terms of the stability of their relationship. No relationship is truly stable given the expiring nature of just about every facet of life, including life itself.
Stoya: And I don’t think the 100 percent morbid position that I have is necessarily what our writer should aspire to, but maybe a good 35 percent of understanding that while it might feel really comforting to worry about this one specific way that this partnership could end, the reality is there’s a constellation and many of these possibilities are something that you have no ability to control.
Rich: Exactly. So personally speaking, I don’t think that cross-dressing is inherently an indicator of a terminal relationship. I do think that how one deals with their partner’s cross-dressing and the level to which they accept it could be the predictor. So that is the thing that the letter writer does have control over to some degree.
Stoya: Do they really have to get married in less than a month? That feels like a lot of pressure. And the fiancé disclosed this about a month away from the wedding. That was his choice. This is where we are now, but given all of the details in this letter, I feel it would be least risky if they slowed down before they put the pressure of legal commitment on this sudden new complication.
Rich: It’s definitely a complication. I agree with you. Ideally, that would be the case. Obviously, if this is some kind of big event that’s already been planned and reserved, that’s going to be a lot more difficult to cancel. There’s going to be a lot more explanation. I would understand the urgency behind the letter in a case where it’s like, “We have this venue that we had to reserve over a year before our wedding date. We have all these people invited, people are flying in, etc.” I get it. But ideally speaking, now would be a time to test things out and see where it will go before you just make it even more complicated by binding yourselves legally.
Stoya: Yeah. So if it’s a potluck in your backyard with a few friends and family who live in town, postpone that, please.
Rich: The other thing that really leapt out at me was this idea of sex as a zero-sum. This idea of like, well, he’s doing that, so that means he doesn’t want to have sex with me. Our writer is better off not taking his masturbation habits personally when it’s extremely possible the reason that he is doing the cross-dressing over having sex probably has something to do with the kink. It doesn’t necessarily mean that he’s choosing one over you, but it means that he’s going where he’s most stimulated.
Stoya: Compartmentalization happens when people feel like they have to keep one part of themselves separate. Say, maybe when they have a fetish for cross-dressing and are worried that their partner is going to reject them over this. So I imagine that’s causing him some psychological discomfort and may be causing him to feel awkward about approaching his partner for sexual interaction after he’s been cross-dressing. For instance, maybe he’s afraid of being asked why he’s in such an amorous mood before he’s ready to talk about that. So I think there’s a very good chance that were he able to bring this sexual interest of his into sex with his partner, it would become less separate.
Rich: Yes. Although they’re still having sex once or twice a week. Our writer reports that it’s the best. So let’s imagine a worst-case scenario for our writer where she never gets into his cross-dressing and he always has this thing he does by himself. They’re still having great sex once or twice a week. That sounds like a compromise to me. That sounds like working it out. It seems like they’re already doing it in a way, so it can only get better from here.
Stoya: And her libido is higher than his, so I would imagine that she masturbates without him. So to her point of getting more comfortable with it—and I’m unsure whether this is a fairly widespread experience or if I’m kind of unique here—most of the time, a partner’s joy in a particular facet of sexuality makes that facet hot for me.
Rich: Totally.
Stoya: It’s the hottest thing in the world.
Rich: It is. I’ll give you an example that might even sound a little bit fucked up. One of my fuck buddies loves to stick his dick in me without lubing it first. That’s always how he wants to start. And because he does it like that and because I can see in his eyes how much he’s into that, as uncomfortable as it is, it’s like, I’m going to let you do that because you’re so into it. Eventually, we’re going to have to grab the lube, but you can start this way because you’re so into it. This is something that actually is uncomfortable for me, but I’m able to override that discomfort because he’s so into it, and then that makes me into it. I’m not advocating for this, mind you. It’s just a situation I’ve found myself in.
Stoya: Yes. Or the discomfort of a few hard thrusts just before someone orgasms, or the hand cramp.
Rich: Exactly. So you can adapt I think through exposure, and it might just take understanding the degree to which he’s eroticizing this for you to get into that. Or maybe you don’t. I mean, there are definitely people who are in mixed-fetish partnerships. That happens. And then again, compartmentalization is possible. There’s nothing wrong with that. Referring back to the fact that they basically already have that scenario now. They’re already having good sex by her estimation. I would also wonder whether he considers their sex good or not, by the way.
Stoya: That’s a very good point. I imagine our writer didn’t have much detail when they wrote this, but looking at this cross-dressing kink in detail is I think really worthwhile. There might be some angle on how he approaches it and what he appreciates about it that might really work for her. And when she describes him as incredibly vanilla, that makes me curious about whether she does have kinks of her own that do not on the surface align with cross-dressing. But if it’s about being decorated for him, there are lots of ways to meet in the middle on that.
Rich: In terms of reading recommendations, I think Perv is always a go-to for getting into benign sexual variation. There’s also a kind of case study to look into. This story blew up I think in the mid-2000s because people found a bunch of snapshots of this Catskills area haven for straight guys who were into cross-dressing together—I think in the 50s or 60s. They’d drive up to this place called Casa Susanna and Harvey Fierstein wrote a play about it called Casa Valentina. You can buy that play and it at the very least, culturally kind of gets at a lot of what’s going on in straight guys who do this.
Again, our writer acknowledges this. Straight guys are into this. It’s a really popular fetish. In fact, when I did some research, straight guys cross-dressing is really, really high on the list of popular kinks. And so at least through this fictionalized version of this culture, maybe she could get a bit closer to what it looks like to do it, and maybe even some emotional truths.
Stoya: She definitely needs to have conversations with her fiancé about what he enjoys about cross-dressing and think through ways that they might be able to interact in scenarios that cater to both of their interests.
Rich: If she really wants to hold onto this relationship and she says she does, that is going to be impossible without some level of acceptance of this. So I appreciate her letter because it is very much oriented toward that. It seems like she’s already pointed in the right direction. Then it’s just a matter of time and getting used to it.
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My husband and I have been married for 15 years, together for 20. He’s a wonderful husband and father and a great match for me in many ways. I love him very much. However, our sex has always been a little less than satisfying. It’s lovely and comforting and connecting, and not infrequent, but it doesn’t get me off.
