I Accidentally Went in the “Backdoor.” My Girlfriend Swears I’m Lying.

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Dear How to Do It,

“Carmen” and I have had six wonderful months of dating and sex. Then one night, while in the spoon position, we started having sex. I remember it felt physically different.

It wasn’t necessarily tight, but more snug than usual. It was a nice, slow jam. We finished, and she said, “Let me get you a cloth to wipe it off.” I didn’t understand. It turns out it was anal sex.

We’d never discussed anal sex. I don’t think it’s a priority for either of us. She said nicely and politely that I could have asked if she wanted to have anal sex. I didn’t know I was going into that hole, and told her so. She became angry and said I must be lying. We mutually started the act, so it’s not like I was hunting. So I told her I was offended that she thinks I would just put it in there, and that I know it would require some prep and a conversation.

She won’t let it go, saying I knew, but she’s not upset and doesn’t think it should change anything. But I’m upset and told her that I saw no need to lie about something like that because if that’s what I wanted to do, I would have asked. It’s been a great time, out of and in bed with her. But I’m feeling like it’s a red flag that she continues to believe I’m not telling the truth. I’m close to ending it while it’s early; am I making too big a deal out of this?

—Never Saw This Coming?

Dear Never Saw This Coming,

Every once in a while, the stars truly align and an unexpected anal penetration happens somewhere on the planet. This is, however, exceedingly rare. I have never in my whole life even heard of a situation where the person doing the penetrating proceeded all the way through that sex without noticing. Carmen shares some of the responsibility for failing to speak up and put a stop to sex she didn’t want, and we’ll get to that later, but the fact that you feeling “physically different” and “more snug than usual” wasn’t a cue to check in more thoroughly is pretty odd.

The combination of the infrequent incidence of genuinely accidental anal, plus your choice to immediately claim ignorance rather than apologizing for neglecting to check in (visually, verbally, or otherwise) when things felt different, is probably why Carmen is assuming you’re lying. We’re stuck in the realm of guesswork, though, because you didn’t ask her more questions and instead went on defense mode.

What’s a red flag for me is Carmen’s lack of self-advocacy during this whole adventure. I feel safe assuming that she was aware, from the moment of penetration, that you were in her rear entry. She chose, for one of many possible reasons, to see it through and then express her discomfort once you’d finished, and to do so in a somewhat soft manner. Why did she choose that path? Whether it was a reluctance to set boundaries stemming from her own personality or history, or something to do with the context of your relationship and the ways you interact, it’s crucial to figure out why and resolve the issue if the two of you are going to keep having sex—much less continue in a significant relationship. Before you approach Carmen and ask for insight, consider whether there are aspects of how you interacted with her before this incident that might have set her up to feel unsafe speaking up for herself. If anything comes to mind, lead with an apology. If nothing does, come to the conversation from a place of wanting to understand what she’s thinking, feeling, and responding to.

I’m working off the assumption that you’d prefer to repair this situation and move forward together. If that’s not the case, do know that at the six-month mark, with no shared living space, finances, or children, I think you’re perfectly within your rights to move on for any reason.

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Dear How to Do It,

My wife rarely had orgasms from penis-in-vagina and detests oral. We tried vibrators with little success. Often, during cowgirl, things would start to get intense, but she’d get a feeling like she needed to pee, pause to use the bathroom, and we couldn’t get back on track. After reading your column, I convinced her the pee sensation might be her getting close and to try riding it out. What’s the worst that could happen? She pees a little? Well, you were right.

I think I found her G-spot, and she said the orgasms are “life-changing.” Cowgirl went from her least favorite position to our go-to, and she finishes almost every time. If I give her a massage first, it’s a ticket to O-town. I’d like to add variety, but we have young kids and she can’t get in the mood if they’re home. So our sex is mostly quickies around the water cooler when we both work from home. There’s not a lot of time to experiment or for foreplay, so we stick with what works. Any suggestions on positions we could try? I’m 8 inches, and it works if I thrust quickly and hard at an angle to the right side of her body. Once I get in the groove, she can’t move; it’s so intense that I’m doing all the movement.

—More Than a Horsie

Dear More Than a Horsie,

Usually, I pitch “explore and experiment” as a leisurely session. In your case, I think it’s better—and could be quite effective—to look for one piece of information at a time. The main point here is to take a small amount of time to try one change, and over time, you’ll slowly get a sense of what might add variety while delivering the same impact.

You know what to angle for. In the interests of time, I’d finish up in cowgirl. Next time, start in a different position and take a couple of minutes to try and find that spot. If you can, great. If not, finish up with what you know works for both of you and try another position at a different time. Missionary seems like the most likely place to start. Spoon also feels like it should be high on the list. Doggy with her waist bent at a 90-degree angle, too.

Remember that your kids will grow older and participate in more outside activities. You’re doing pretty great already. You’re keeping your erotic connection alive, and even finding new ways to increase the enjoyment you’re getting out of it. It won’t be that long before you’re able to go on a romantic weekend without worrying about your family. You’ve got this.

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Dear How to Do It,

Hi guy and gal (am I doing this right?), I’m a 50-year-old cis male, and I haven’t had sex in nine years. The problem is that this entire time, I have been in a relationship with a cis woman who may end up being my forever lady. Just with no sex. For me, this is an issue, because I am the sort of man who has no trouble getting dates, and has always had a girlfriend (all of them still my dear friends) with whom I enjoyed a vigorous sex life.

But I have reached a point in life where 50 is not really the new 30, and I would still like to get laid before the light turns off completely in the bedroom. I cannot imagine doing the cruel thing and just tossing my girlfriend aside simply because she appears to be asexual, but I also cannot imagine doing the cruel thing to myself and settling for a sexless quasi-marriage out of pure kindness.

BTW, she fits my silly kink: She always keeps me learning. I like that. Our platonic relationship is a good one, even though I never imagined I’d be in one like this. It’s maddening. Is there therapy for this? Should I break up now and just move on, so that we don’t have to keep doing this?

Dear Sexless Late Summer,

“Guy and gal” is an adequate form of address for Rich and me, yes. You do only get the “gal” portion of the team today, but I think I can help.

When you ask whether there’s therapy for “this,” if you mean for navigating libido discordance or the ways our relationships to sex and our bodies change with age, there are loads of therapists, counselors, and coaches in the world who have expertise in either area. If you’re asking whether there’s therapy to change your girlfriend’s interest level in sex, the most important factor is whether she wants to try to change that. If so, she’s free to write in, and, depending on the details of her relationship to sex, there might be. But that’s a decision for her to make, and that’s not a question I can give potential answers to without more context.

I’d start by asking your girlfriend how she feels about sex and whether she’s interested in having any form of sexual contact. If she’s open to it, follow up with inquiries about what she wants and might need to support that. If she isn’t, let her know—with kindness—that you love her company so much (and do include a few brief specifics about what you love) but that you do want to be having sex, and ask whether she’s open to working together to find a compromise.

Sometimes the partner with the lower libido holds the other while they masturbate, other times people try out a version of an open relationship, and sometimes the partner with the higher libido learns how to appreciate erotic activities that are outside the script we usually see in media. What’s possible for the two of you is going to need to come from gentle conversations about what both of you need and want, and looking for areas of overlap.

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My wife and I are a young-at-heart couple in our mid-50s but presenting measurably younger. I, for example, have managed to keep all my own teeth, my hair in nearly the same color as my youth, and I can see all my toes when I stand up. By the standards of straight middle-aged men in the U.S., I’m a 10! Our sex life as a couple can be characterized in a word as “ecstatic.” Our problem/query: We don’t find ourselves invited to any group sex encounters?