Let me start with some background: My wife and I have stopped having sex due to an ongoing medical issue on her side. Prior to that, our sex life was very active and she was (and in a way, still is) a very sexual person. So, she gave me permission, and even insisted that I find an alternative sexual partner until she feels ready to have sex again.

I started a sexual relationship with a coworker with whom there was lots of preexisting chemistry and sexual tension. We meet once, sometimes twice a week, and have rather satisfying sex. At first we used condoms, but after an open conversation about STIs, and some time getting to know each other, we developed enough trust to go bareback. Since I really want to avoid the possibility of pregnancy, and since we both liked anal play, our sex routine consists of oral and anal sex. The ratio of each act is variable, but there is always an anal finish. Last time however, after a prolonged oral session she got on top of me and mounted my penis. We were both very worked-up and it soon ended with strong mutual orgasm. Only after some time when she got off me, I realized we actually had vaginal sex. I always believed I could differentiate between anus and vagina, but the one time it counted, I felt nothing out of the ordinary. I still don't understand how.

Anyway, I felt really betrayed and we had a massive argument in which she claimed she thought I was aware of the nature of our sex act and even tried to put the blame on me for risking pregnancy by ejaculating inside of her. I thought my anger would subside after going home, but instead it only grew. I feel my trust is completely betrayed to the point where I feel physically violated and it doesn't help that I feel paranoid about possible pregnancy. She acts insulted, rejecting any possibility of her own agency in what happened and refusing to inform me about the measures she took to prevent getting pregnant. I do not discuss my alternative sex life with my wife (at her own request) but this thing is just tearing me apart and I don't know what to do. I have a range of negative emotions that feel overwhelming and I am not sure how much longer I will be able to go through it on my own. Is all this my fault, and what should I do?

No, this isn't your fault. While it is somewhat surprising to read that it was only after the fact that you realized the sex you were having was vaginal, not anal, I'm willing to go along with you here. We have heard from women whose partners have "accidentally" slipped in the backdoor when there was the understanding that they'd be going through the front, and your situation is the inverse of that. Unique, but no less a violation.

Look, if you had an explicit (or even implicit) understanding that your sex would be confined to oral and anal, she had the responsibility to announce that she wanted something different that day. Why does she think that you were aware of what she was doing if she never did it before and didn't signal that she was doing it? She sounds unable to accept accountability -- to do so would be to, at minimum, validate your experience and acknowledge its possibility. Even if she believed what she was doing was obvious, the ethical thing to do now would be to recognize that you perceived it differently. Do you want to keep this up with someone who's behaving unethically?

You feel physically violated because you were. Regardless of her intent or interpretation of your perception, you were in the dark and now you have feelings about it. It seems like you could use an outlet to get your feelings off your chest-consider a therapist or a sex coach to help you work through it. In the meantime, it would be completely understandable if you stopped seeing your co-worker. You had a good thing going until it wasn't. This is the life cycle of many a situationship. Figuring out how to navigate working together after something like this dries up will be tricky, but it was always going to be that way. It's a hard lesson that you set yourself up to learn.

Dear How to Do It,

I've never been able to masturbate to completion. Every time I feel myself getting close, the feeling suddenly becomes "too much," and I have to stop or slow down substantially. It's a very powerful instinct I have not been able to overcome.

Because of that, I have never been able to make myself go all the way. I've tried regularly for years. I'm a trans man, and I've seen other people with the same parts describe having this issue, too, so I know it's not just me. But all the advice I've seen from them has been "get a vibrator" (I have a Magic Wand) or "just don't stop," which is the thing I'm trying to deal with! How can I push through the feeling?

"Just don't stop" is indeed common guidance for when things become "too much." In Come Together, Emily Nagoski writes about the legendary sex educator Betty Dodson's instructional videos, in which she coached women to orgasm:

But naturally, this advice won't work for everyone and what goes for cis women won't necessarily go for trans men. So I reached out to Dr. Damon Constantinides, a queer and trans sex therapist and coach, who runs virtual sexual pleasure groups for trans and queer folks, including the eight-week Trans Masc Sexual Pleasure program. (His Instagram is here and his TikTok is here.) He told me that "just don't stop" isn't bad advice per se, "But if it's not working, then it's like, what else is there to try?"

Your Magic Wand might not be it. Constantinides said that because testosterone can change your anatomy, different stimulation may be more useful -- an up-and-down movement may be preferable to simple vibration. (You didn't mention whether you were on T, but if you are, there you go.) Other toys you might want to try are sleeves (like these), or the type that use air pulsing (like those offered by Satisfyer). Try multiple approaches, too. Hard and fast, a la the Magic Wand, may not be working for you, but how about slow and sensual? You might also want to experiment with sensory deprivation (blindfolds, ear plugs) to hone your focus, and other areas/types of orgasm like nipple and anal.

Constantinides had a lot of questions as a result of the sparse information you shared, so his primary advice was to do more exploring and see what you dig up. A big missing piece is how you feel about your body. "We know that when we're experiencing anxiety, we can't orgasm, right?" said Constantinides. "That turns off that whole process. And so what I found myself really curious about with this person is: What is their experience with their dick? How do they feel about it? What is that like?" You don't mention dysphoria, but if that's playing a role, it may make things harder for you. "Sometimes dysphoria can show up as just numbness or not being able to notice what you're feeling. Sometimes it's not as obvious as, 'Oh, I hate this,' " he explained.

Something else that might be useful: Watch porn featuring trans guys. See what comes up for you emotionally. "What happens if you're watching trans men masturbate? What happens if you're watching trans men having sex?" wondered Constantinides. The overall idea is to collect data to foster a greater understanding of yourself, your sexuality, pleasure, and, ultimately, what will get you off.

Have a nagging (or totally inconsequential) question about sex? It's fun to see your words in this column! Send it in now.

Dear How to Do It,

For most of my life, I've been in sexually satisfying relationships that often involved swinging and non-monogamy. I've been married three times and had many wonderful lovers. My current husband is 74, and when we first got together, things were great. Then I looked at him one winter and saw that he looked sick. I insisted he go to the doctor. He ended up having open heart surgery and survived it.

My problem is he has become bedridden and I now have to change his diapers. Most of the time, he just sleeps and eats. I have lost interest in having sex with him, even though he's still interested, and I'm trying to figure out how to handle that. My therapist asks how we were keeping the affection, but there is now just occasional kissing. After my therapist asked the question, I did ask him if my taking an occasional lover would be a problem. He said his feelings would be hurt. Now I'm looking at the rest of my life condemned to a sexless existence. Suggestions?

It is good and necessary to be sensitive to your partner, but "my feelings would be hurt" sounds like a soft no to me. Your partner's feelings would be hurt if you were to step out, but if you don't, your feelings will be ... what? Frustrated? Resentful? Horny beyond belief? Also hurt? It's his feelings against yours. At minimum, this requires a follow-up conversation. You should impart just how much this means to you -- given your patterns of behavior, it seems that you're inclined toward non-monogamy. Your history makes it somewhat surprising that you settled with someone who is monogamous -- if I were you, I would have gotten this conversation out of the way early on. But live and learn. In the future, go for partners that are more open to being open.

From what you describe, it seems like sex is truly off the table with this man. And yet you are (or at least feel) obligated to care for him. I think you deserve to get yours as well. I'm not telling you to cheat, but isn't he ultimately at your mercy? Don't exploit your power, but also don't take it for granted. I would try to figure out a way to make this ethical -- if knowing you're having sex with someone else would hurt his feelings and you don't want to hurt his feelings, could he be open to a don't-ask-don't-tell arrangement? It just seems totally unfair that you should have to put in the work that you are and also have to give up sex. That's not just free labor -- it's free labor that you have to pay for. It's upstanding of you to stay with someone and take care of him in his condition, but that's enough of a sacrifice. If you can't figure out an agreement with him, consider couples counseling, perhaps via Zoom. In fact, even if you do figure out an agreement, counseling could help with the necessary communication in an open arrangement and just generally keep you on course.

Dear How to Do It,

Over the past few months, I switched over to being more sex-forward in my dating bios on Feeld. It's been great for finding more adventurous hook-ups and friends with benefits -- seriously a lifesaver. But recently, I've started going on more serious dates with guys from the app who are looking for relationships. Our conversations prior to meeting start out very sex-forward, which I appreciate, because the problem I was having on other apps was that I'd go on several dates only to find out we were a terrible sexual match. I'd often wind up feeling like I'd wasted my time.

Now I'm having a different kind of problem. I'll go on these dates -- after having these great sexual chats beforehand -- and then find that we've perhaps built these talks up a little too much. I won't exactly click with them, it'll be a little awkward, and I won't feel the spark, and yet, I'll feel like I'm in too deep and sleep with them on the first date anyway. I've done this a few times now and don't exactly regret it, but it's also not working. I probably shouldn't be having sex I'm not super into! How do I stop giving into this self-inflicted pressure? Do I just need to revert back to putting sex on the back burner in my dating life?

You should definitely not be having sex that you aren't super into. That is a hazard with apps -- imagine what it's like when no date is involved and one person goes to the other's house based on horniness and a dream. When mediocre sex ensues, it's an illustration of how these apps that were designed to make hooking up easier actually come with their own complications. Meeting people virtually is barely meeting them at all -- our brains fill in the spaces that they leave and if we're prone to optimism or are just excited about getting laid, it can build expectations up so high that they just couldn't possibly manifest as perfectly in real life as they play out in our heads.

But I think there's a happy medium here: Don't engage in so much sex talk prior to meeting. Be upfront in your profiles but keep the sexual back-and-forth to a minimum. You can say why: "I've gotten a little carried away in the past, and would rather meet in person to check the vibe." The good news is that you are going on dates, which provide very good buffers. They allow you to check whether whatever sparked your interest on the apps holds water IRL. If not, don't go home with them (or invite them over) after your public hang. Being upfront is going to save everyone time, but if letting someone down to their face is too difficult to you, just make up excuses: "Thanks, that was fun, but I have an early day tomorrow," or whatever. With a bit more space for deliberation, I think this should be pretty easy for you to overcome.

-- Rich

I recently met this woman who told me she was in an open marriage, and we started hooking up. It's been amazing -- I really like her, even though I know we'll never be anything more than lovers. Everything was going great until I accidentally stumbled across her and her husband at a work event. And guess who her husband is: My boss. I am absolutely panicking. What should I do?