I’ve Been Having Hot Sex With My Boyfriend and His Brother

10 min readMay 18, 2021

I don’t want it to end after lockdown.
Dear How to Do It,

Last year, my boyfriend’s brother lost his job during the pandemic and moved in with us. We spent a lot of time together (I also was out of a job) and started to have sex every once in a while, and then we started to have it a lot. We both felt guilty about doing it secretly so we fessed up and were surprised and happy that it was OK with him. For the first couple of months I just bed hopped, but then they both decided they wanted to try it at the same time. No ick factor because they don’t have sex with each other; they just both have sex with me at the same time. I’ve done it with two guys before, but never when I loved both of them and this has been the best sex and the best relationship I ever had. But now brother got a new job and boyfriend wants him to get his own place. That would be bad enough, but he also wants to go back to us being monogamous with each other. I don’t want to do that. He asked if I was choosing brother over him and I said no, I want them both. He says this was just an arrangement for convenience when we were all thrown together, but there’s no need for it anymore. We haven’t talked to brother about it yet because we want to resolve how we feel about it with each other first. Is there some way this could work out?

Dear T.B.T.B.,

Unlikely! The ick factor here is in the back of the throat of the beholder. Your pandemic hobby was certainly pointed in the general direction of taboo. The threeways you describe weren’t incest, per se, I suppose, just like imitation crab meat isn’t crab meat. Same general idea, but a technically different endeavor if we’re splitting hairs (or exoskeletons, as it were). Therefore, I’m not sure how sleeping with your boyfriend and his brother at the same time could ever be construed as being for the sake of convenience — if nothing else, it seems guaranteed to complicate whatever existing dynamic exists.

As for moving forward, the romantic in me feels that one’s loyalty belongs to your initial partner, especially if you’re going to want to remain in that relationship. The brother dick was just an accouterment. And so, if you want to stay with your man, you should “play to the level of the least comfortable person, if you want to keep everybody happy” (in the words of a semi-anonymous man named Shawn whom Tristan Taormino quotes in her book Opening Up).
Or pick the brother. But you can’t have both. That might be frustrating, but not being able to sleep with a guy and his brother at the same time is actually pretty standard, you’ll find if you look around.

Dear How to Do It,

I started talking to an old crush about a year ago on Facebook. He’s been calling almost every day since Valentine’s Day. We haven’t seen each other in almost 30 years, but have a reunion next month, as we live in different states. I’m thinking sex is in the picture. I’ve been separated and divorced in the last two years. Would it be bad to have sex next month, the first time we see each other in 30 years? And I’m worried about my body acting crazy since I haven’t been physical with anyone in a while. What do I do?

— Hot, Confused, and Nervous

Dear H.C.N.,

Do what feels right when you see him. In our uber-connected world, sex is so often facilitated when bodies are not in the same room. The mind fills in spaces and creates anticipation that the sex cannot live up to. Sometimes the very image you have of this person in your head is betrayed by their actual physical presence, which can only be conveyed completely when they are live and in front of you. Disappointment ensues. In the meantime, do what you can to ensure that your body is ready, and not just figuratively. Get in touch with yourself sexually, if you haven’t been, by, for example, masturbating and/or fantasizing, if those things appeal to you. I’m not sure what your “body acting crazy” might entail, but if you’re going to be penetrated, you can play with a toy by yourself to make sure you aren’t sealed tight, come your reunion. Try to relax and go easy on yourself. The human body can be full of surprises, and a compassionate partner will forgive that which is beyond your control.

Dear How to Do It,

I’m a transmasculine person who’s currently dating a butch, cis lesbian. We met a few months ago and things are going well so far: We care about each other, we laugh a lot together, and we have good chemistry. But there’s one problem: Whenever she talks to me during sex with a softer, more feminine voice than she otherwise uses (“can you touch me there?,” etc.), or whenever I see her in a bra or with bare boobs (i.e., when she doesn’t have a T-shirt on or when we’re not in the dark), I feel … intense, full-body revulsion. Over the past five years or so, I’ve generally dated people with more testosterone-y bodies who either have flat chests or who hide them, and who have relatively deep voices, so this hasn’t come up for me before. (Before that I was dating a lot of cis women but was also pretty messed up about sex, and I’m not really sure how I felt then.)

I have a few theories about why this might be: 1. Maybe I associate these things with femininity and that catalyzes gender dysphoria in me, as I haven’t been able to transition yet but really want to. (Her chest is also a similar size to my chest, which is quite large. Imagining more petite boobs doesn’t squick me out in the same way.) 2. Maybe these things are triggers for my trauma. I was sexually assaulted by a cis woman the first few times I had sex, and that’s led to debilitating PTSD for me that I’m currently working on in therapy. 3. Maybe I’m just … not attracted to people with boobs and “feminine” voices? But also, I do enjoy intimacy with her a lot of the time, so that’s not completely convincing to me either. Telling her about this seems cruel and unnecessary, but not telling her seems kind of dishonest (we make a significant effort to be honest with each other about things, including sex stuff). This doesn’t seem like an important enough reason to end things — we really like each other, and that’s a special and rare thing! — but regularly experiencing this very strong disgust does also affect, and destabilize, me a not-insignificant amount. What should I do?

Dear T.T.,

For specialized insight, I shared your question with Nick Marzo, licensed professional counselor, certified sex therapist, and director of the Modern Path mental health service. Not incidentally, Marzo is a transmasculine genderqueer person. In an email, he noted your sensitivity and self-awareness, and wrote that he suspects that your first two theories may play a role in what you’re experiencing. “Dysphoria and trauma can show up in many ways, including a visual or verbal cue from an outside source, even from those we love and trust,” wrote Marzo.

He suggested performing an exercise (with the support of your therapist) to help you process:

Imagine a time when you heard her soft femme voice, saw her breasts and felt that sense of repulsion in your body. Breathe, ask yourself what is this repulsion? What does it look like? smell like? If it could talk what is it saying to you? Notice your breath and remind yourself two things: First, you are not with the woman who harmed you, this is your partner and name positive qualities of the relationship and your intimacy together. Second, this is her body and her asking for pleasure.

Something adjacent to this last point struck me when I read your letter. It is possible that you’re still learning about your own attraction, but broadly speaking, new partners sometimes do things that turn us off. These things can be as deep as insights regarding how they see the world, and they can be as simple as indications of their humanity. When your partner talks to you in a softer, more feminine voice than that which you are used to, she is showing you more of herself. Part of getting to know someone is understanding that they are more than what they present publicly. This is part of any relationship; the question here is: Can you handle the more complete picture of her humanity?

Marzo recommended discussing your feelings with your partner, perhaps avoiding words like “revulsion” while articulating the emotional experience you described in your letter. Marzo suggested something like: “When we have sex with the lights on and I see your breasts or hear your soft femme voice, I think I experience dysphoria and possibly some impacts from my PTSD. I am wondering if we could try some things a bit differently while I continue to work through these things with my therapist.”

Additionally, Marzo wrote that if your therapist is not well-versed in issues around trauma and/or gender identity, you should consider seeking an AASECT-certified sex therapist with a background in both fields. Good luck!

Dear How to Do It,

A while ago I discovered that my husband was spending hundreds of dollars a month on adult webcam sites. Our sex life has been sporadic during our marriage, and I never could understand why, so after this discovery I assumed that his interest in pornography was beyond using the medium as a masturbation aid and started to wonder if sex with me was actually the odd occurrence that interrupted his preferred routine. I have tried desperately to be understanding, work through the issue, and seek therapy to sort out my own feelings about the situation. He’s told me that he has stopped going to the site he had been using, but bank transactions tell a different story (we have separate accounts). We are not wealthy, but firmly middle class. His use of this site has not just impacted the emotional side of the marriage, but it has bled over into our parenting also because he is reluctant to contribute to the financial needs of our child. He gets angry with me when I try to talk to him about how much of a problem this is and refuses to seek therapy or any help from a professional. Regardless of if the marriage lasts or not, I’m concerned about him being able to be a present father in our child’s life because his pornography use has become such an issue. He says that he feels ashamed of his actions, but he doesn’t seem to be able to stop on his own. Is there any tactic that can be used to help him see the bigger picture? This isn’t just impacting two adults any longer, but a child as well. My sexual needs have been thoroughly neglected by him, and I have no interest in porn.

— Losing Optimism Daily

Dear L.O.D.,

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In the name of nonviolent communication, it’s important to frame things in terms of how you feel, without accusation. I think shaming your husband could prompt him to retreat further. Saying, “I fear for our relationship’s future and our child’s financial stability,” is probably going to be more constructive than, “Holy shit, you’re blowing up our lives a little more every time you blow a load.” Godspeed, though — I don’t know if I would have the patience required to work through this. It is outrageous that your husband isn’t contributing to your child’s financial needs. Your letter has pointed to something worse than an estranged deadbeat dad: a deadbeat dad who still lives at home. That’s a big wow for me. At the very least, I can see the toxic logic in someone who deprives their child for being out of sight and mind. Your husband gets to look at what he refuses to support every day.

Unfortunately, you can’t help someone who won’t help themselves, and if there’s a compulsive component to his porn use, he’ll be even harder to convince. You seem resigned to the ultimate dissolution of this marriage. If and when you lose your patience, you can certainly lay out what he’ll be giving up by squirreling his money away for cam play. Some perspective in the form of an ultimatum may work if he isn’t completely lost to internet porn, which he may well be.

— Rich

More How to Do It
If a straight man receives oral from a trans or gay man does that make the straight man gay? Asking for … a friend.

I’ve Been Having Hot Sex With My Boyfriend and His Brother

Written by Philipmatthews

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