Go Ask Alex: My younger partner won't bottom. How do we save our sex life?

I enjoy your column, and I have a situation.

I’m in a committed, monogamous relationship with a man 14 years younger. I recently came out after a 25-year marriage to a woman. Following my divorce, my partner and I found each other online, long-distance.

We started slowly, as friends learning about each other’s lives, building trust and a foundation. We shortly exited the apps and turned the relationship romantic.

We now live together; my children and my mom get along with my partner very well, and he’s become a part of our family; I love him and tell him that often. He is super loving, caring, and concerned about me.

We lack penetrative sex and, in particular, me topping him. We used to have sex once or more a week, but in the last several months, that’s dwindled to once a month. At the point I’m writing this, from a vacation, we’re now going on five weeks without anything other than handjobs or blowies, and with both, we ultimately are getting ourselves off with the other participating alongside, not penetrative sex.

Sex with my partner is a bit laborious. I am large to him (8”), so it’s an undertaking, let’s say, to get him ready. There’s also pain; I sense he doesn’t like to bottom because of the discomfort, though once I’m fully inside, hoping my erection lasts, he seems to enjoy it, but he won’t let me go wild on him because it hurts. He doesn’t do anything really about the pain or getting ready, such as stretching, poppers, etc.

So, more often than not, I end up bottoming, as it’s easier to get sex going that way, and because I also want to make him happy, and I enjoy bottoming. Plus, he likes me in that position; he enjoys the domination, though afterwards he also tries to persuade me that I’m “the bottom” in the sexual relationship. No, I’m really not.

I’ve racked my brain to try to figure out how to deal with this issue, maintain the relationship, and not hurt his fragile ego. I’ve considered ultimatums, asking for hall passes, suggesting finding a third or another couple, and even reentering the apps to talk to other guys about the issue. The solutions involving others concern me because I feel they could erode trust and end up breaking us up. I also think it would hurt his heart for me to suggest that.

Bottom line: I came out of a sexless 25-year heteronormative marriage to be authentic and settle for nothing less than personal and sexual fulfillment. How can I maintain a relationship with my partner, who I love so much, and I don’t want to lose, without frequent, penetrative sex being involved in our relationship? How do I even broach suggestions about sexual fulfillment from others with him, if that’s what I am to do?

Sincerely,

Frustrated.

Hey Frustrated,

Yeah, that’s frustrating. I wonder if, in all the time you spent chatting online, you talked at length about sex?

Based on your question, I’d say your partner just isn’t into bottoming. In fact, he seems opposed to it and seems to prefer being dominant in bed.

He may not have been aware of this when you were chatting over long distance, so he might not have communicated these desires so well. But he’s giving you every sign that he’s not into it — he’s even trying to designate you as “the bottom” in your relationship.

Waving aside the (false) assumption that every gay relationship needs a bottom and a top, he’s all but explicitly stated what he wants you to be — and that, paired with his obvious discomfort and displeasure in receptive anal sex, makes me think you’re dating a top who is willing on rare occasions to bottom for you because he cares about you, but not because he wants to. And it sounds like you’re the same.

Your message makes it clear that some great aspects of this relationship make it worth preserving. He’s a loving partner. Your family likes him. He’s attentive and caring. If your relationship is solid, it sounds like you’re able to talk about things and communicate well — that is the core, necessary ingredient of all happy couples — so why are you nervous to share these feelings and frustrations with him? If he’s a good partner, he’ll be willing to talk, patiently and kindly, about all this — as, indeed, he must. You should be bringing these concerns to him.

I know many gay romantic pairings of men who both prefer to top. None are monogamous. Sorry, but that’s how it is. If neither of you desires bottoming, you have limited options: 1) every time you want to have penetrative sex, one of you must reluctantly bottom, and without this being the desired option, it makes sense that the amount of penetrative sex you’re having would decrease over time; 2) you can rock a total bottom’s world by sharing and gang-banging the shit out of him all night, together; or 3) you can both have sex with others who satisfy your respective desires and go home to each other every night to enjoy all the closeness and intimacy you already have, with your sex needs met elsewhere.

Sure, there’s a fourth option, too: You can break up. But that seems needless when you have a great relationship! You might just have to join the countless gay couples that aren’t totally, 100 percent sexually exclusive.

And, yes, that means communicating well — talking about feelings of jealousy when they arise (they will) without screaming and slamming doors — and being patient and understanding with each other. But these are the exact requirements of all happy, successful relationships.

Do not re-enter the apps. Don’t do anything without talking to him first about all this. If he does not listen, hear you out, and respond kindly, that’s a red flag that he might be unable to have this kind of mature, adult conversation — and that doesn’t bode well for any relationship, gay or straight, monogamous or otherwise.

I’m fully with you in the last paragraph of your message. I feel that. Do not settle for anything less than sexual and personal fulfillment — that is what we all deserve.

He deserves it too. You both deserve the sex you want — not the reluctant, “only if I have to,” take-one-for-the-team sex, but the sex you fantasize about. What are his fantasies? Have you asked him?

You guys need to talk about sex — honestly, transparently, patiently. To answer your final question, you broach this conversation by saying something like: “Hey, we don’t need to have this conversation now, but can we schedule a time to sit down and talk about sex? I want to hear your thoughts on it, and I want to share my thoughts too. I don’t want this to be rushed, so let’s choose a time when we’re both free for the evening.” That’s it.

If that sounds serious to him, that’s fine — it is serious. The stakes are high. Yes, he might respond with insecurity and anger at the mere suggestion of sex with others, and that could end your relationship. But in its current state, your relationship is likely to end anyway — you’re so sexually dissatisfied that you’re considering ultimatums and going on sex apps to talk to random strangers “about the issue” (please).

You’re at the point where something needs to happen. This conversation is it.

Hey there! I’m Alexander Cheves. I’m a sex writer and former sex worker—I worked in the business for over 12 years. You can read my sex-and-culture column Last Call in Out and my book My Love Is a Beast: Confessions, from Unbound Edition Press. But be warned: Kirkus Reviews says the book is "not for squeamish readers.”

In the past, I directed (ahem) adult videos and sold adult products. I have spoken about subjects like cruising, sexual health, and HIV at the International AIDS Conference, SXSW, the Icahn School of Medicine at Mount Sinai, and elsewhere, and appeared on dozens of podcasts.

Here, I’m offering sex and relationship advice to Out’s readers. Send your question to askbeastly@gmail.com — it may get answered in a future post.