My Boyfriend Likes to Play Out Scenarios in Bed. Some of His Latest Ones Have Gotten a Little Personal.

Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!)

Dear How to Do It,

My boyfriend and I have a very satisfying sex life, but lately he has been doing something that really bothers me. I love playing scenarios, and with former partners spent a good amount of time talking about who we’d like to be and what we’d like to do. But my boyfriend prefers improv and just seeing where it takes us.

It has taken us to some unexpected, yet interesting places, and I’ve done things I never would have agreed to had we discussed it ahead of time. I’ve discovered my threshold for pain is greater than I realized, and it has resulted in some of the best orgasms I’ve ever had.

My problem is not what he does to me but why. In the past couple of months, he has repeatedly crossed the line between fantasy and reality, using things that happen in our real lives in our scenarios. Things like “what’s the proper punishment for a girl who doesn’t clean her hair out of the drain cover after she showers” and “digging through the ice cream for the cookie dough chunks is a serious crime.” I told him I don’t like it when he does that, but he just laughs it off and says I must feel guilty if I take it so seriously. But I don’t think it’s funny, and I don’t think it’s fun. Punishing imaginary transgressions of a fictional person is a game; what he is doing feels like assault. Is he right and am I making a big deal out of nothing? Or is he wrong to use our sex play to get back at me for things I do that annoy him?

—I’m Not a Bad Girl

Dear I.N.B.G.,

He’s wrong for not taking you seriously. He owes you more as a partner and as a negotiator. Despite your inclinations, you conceded to role-playing on the fly. Out of appreciation for that, along with the basic respect that healthy relationships require, he should honor your requests. A risk of freestyling is you may wander into uncomfortable territory, and it’s up to both of you to steer yourselves out of it. A common way of doing this is a safe word. If you don’t have one, develop one and use it—it signifies a hard no, and perhaps more importantly, the opportunity to reroute the play into something that is mutually comfortable. His conclusion that you “must feel guilty” if you don’t like his introducing reality into your fantasy is glib and shortsighted. There are any number of reasons why you may not enjoy this particular turn your play is taking. One obvious one is that you want to keep play playful and not be burdened by daytime living while in bed. I don’t think that him referencing real life necessarily constitutes assault in free-for-all improv, but now that he’s aware of your feelings and your lack of consent, he’s certainly pointed in that direction. He should change that. He’s making you feel bad, and the point is to feel good. If this is no big deal, something to laugh off, then why is he so insistent? His attitude is troubling. If he wants to keep in good standing with you—and, as your partner, he should want that—it’s up to him to change things up. Let him know this, and if he doesn’t, find a better, more considerate dom.

—Rich Juzwiak

From: The Things My Boyfriend “Punishes” Me for Have Gotten Really Weird. (June 21st, 2021).

Dear How to Do It,

My husband and I have been happily married for 16 years and together for 17. We have four amazing children. Our sex life has always been amazing, never boring. We have worked to keep things interesting and make intimacy with each other a priority. Within the past year he has revealed to me that he has fantasies about dressing up as a woman in the bedroom. I made sure my reaction wasn’t off-putting and took time to think about it. I decided to give it a go. When the kids were out, he got dressed up in a skirt, underwear, bra, and one of my shirts. We had sex. He loved it a lot. I acted excited, but I was still trying to process it. Over the past few months, it’s gained more and more momentum. He even tried out some of my makeup at one point and now has several pairs of his own high heels, and he bought me a strap-on to use on him. He says he has no interest in dressing like this in public. He is also very adamantly straight.

I am having a really difficult time sorting out my feelings with this. It is not in any way a turn-on for me. It is actually a complete turn-off, but I don’t want him to have to hide a part of himself from me. I want him to be free to be himself with me 100 percent.  I just don’t know what to do to be all right with this. This is causing me a lot of anxiety (I have started taking anxiety medication because of this) and I feel like this could change our relationship whether I say something or not, and I don’t know what to do.

—Not Into Cross-Dressing

Dear Cross-Dressing,

Kinks, particularly when they’re newly explored or indulged, can result in a fairly selfish zeal. His experience might go something like “Oh! I’m finally able to talk about this. My wife is willing to participate in my desire. Exciting! Let’s do all the things! Fun, fun, fun!” without space to consider whether you are enjoying yourself, too. This is where you have to advocate for yourself. Your desires and satisfaction are of equal importance to his. And you’re taking anxiety medication to cope with your feelings, so your relationship has already changed, in a way that is detrimental to your mental health.

You’ll want to begin addressing this sooner rather than later. Whoever is prescribing the anxiety medication seems like a good place to start. If they offer therapy, can you afford a few sessions with them to talk through your feelings? If not, is there a sex-positive therapist you could speak with? If the cost is prohibitive, journaling, walks, showers—whatever helps you think—can be useful. The better organized your thoughts are, and the better you understand your feelings, the more productive the conversations with your husband are likely to be.

You’ll want to choose your time wisely and tread carefully. If you bring up your turn-off response in the middle of a sexual interaction, or even when he’s hinting at cross-dressing play, there’s a higher likelihood of him receiving your communication as judgment or rejection, or feeling shame, which can make clear thinking and discussion difficult. Directly after sex is also likely to be problematic. And you’ll want privacy and enough time to have a full discussion.

Start with your appreciation of him and your desire to support him in living his fullest sexual life. What you’ve written here is great—you want him to be able to be open with you and be himself 100 percent. Then move into your own experience: You aren’t aroused by him in women’s clothing and are engaging in this with him because, presumably, you love him and want him to be satisfied. Ask for his help in figuring out solutions that work for both of you. This might mean catering to his desires sometimes and to yours at other times. This might mean agreeing to open up your marriage to professional or recreational partners who do enjoy cross-dressed sex. This might mean that the two of you are no longer a sexual match. You don’t have to come up with answers immediately, and give yourself and your husband plenty of space and time to process. You might find that something you think will work doesn’t when you actually implement it, or you might find an unexpected compromise. Good luck.

—Jessica Stoya

From: My Husband Finally Revealed His Deepest Sexual Desire—and I’m Losing It. (April 13th, 2021).

Dear How to Do It,

I just got to have a sexual experience with a guy I’ve been desiring for a long time, and it was such a disappointment. He could not penetrate me. We tried all kinds of positions. We are both big but not obese, and he has a big “beer” belly. He kept telling me to relax, but I was relaxed. I wanted him. I was well-lubricated—my panties were soaked. I am in my early 50s and never had children. The few sexual partners I have had never had a problem like this. I have used dildos without problems. My overall impression was that he was “short,” but he left me feeling like I was the problem, that I was too tight. I have not been having a lot of sex but masturbate regularly and enjoy the “penetration” part of it. This is definitely a sexual relationship, and I don’t see it going on if the encounters continue in this manner. Is there something I could do to not be so tight?

—Desperate Girl

Dear Desperate,

He left you feeling like you were the problem? That’s concerning, and I’m not sure you ought to pursue this liaison. Surely there are other people in the world who you find attractive—people who won’t blame you when things don’t go as expected. It can feel sad to learn that someone you’ve desired for a long time isn’t who you thought he was, but it’s always better to have that information sooner rather than later.

If you decide to persist with this partner, jessica drake has an explicit educational video on plus-size sex that might help you troubleshoot. You also can stretch out beforehand with a short, thick dildo. And you can experiment with positions that present your vulva with as little flesh preventing penetration as possible—knees up, on your side bent at the waist, and face down with a stack of pillows under your hips. But the best thing in this situation still might be to mourn this crush and move on.

—J.S.

From: I Finally Had Sex With My Crush, and It Was … Not What I Expected. (January 12th, 2021).

More Sex Advice From Slate

I’m a 33-year-old man. I realized/admitted to myself that I was bi after I first started dating my now-wife (also 33) seven years ago. We took a break early in our relationship for about a year because of unrelated life events, but because of the circumstances, I wasn’t really able to explore my newly realized sexuality. I only hooked up with one guy during that period and it wasn’t super great, honestly.