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Dear How to Do It,

I’ll be 50 this December, and my sweetheart of two years is a healthy and active 63. Our relationship is fun, supportive, passionate, and the sex is AMAZING. I am lucky to be one of those women who can orgasm over and over, and in our play sessions I often come ten times or more. My problem is him—in two years together, he has NEVER had an orgasm. We just play until I’m exhausted and happy and he gets tired. I don’t know if it’s age-related or what, but he also rarely gets a really rock-hard erection (with me) either. I’ve been with probably 10 men in my life (including two unhappy marriages), and I’m told I’m really good in bed. I’ve never had any problem getting men off orally or of course with vaginal or anal sex. He seems to have VERY specific ideas of what he wants at any given moment and is really good at gently directing me—”press your finger here” or “just rock” when I’m on top, so that’s nice but ultimately not successful. I’ve even tried prostate stimulation in his rectum while giving oral, but I never did feel the “rough, walnut-like” object poking through the walls that they mention in videos, and he never responded with the earth-shattering orgasm I was hoping for.

Sometimes his breathing and the sounds he makes make me think that he has orgasmed, but I find out he didn’t. (I’ve never been able to feel a man ejaculate inside me, so I always just judge by his behavior.) I have a nice enough face and thick hair I’m proud of, but I’m overweight— I weigh about 190 at 5’2”, and he’s very fit. (Trying to get in shape but it’s so hard during menopause.) My weight and the fact that he usually likes to do it in the pitch dark make me wonder if, although he loves my mind/heart, maybe he’s disgusted by my appearance. But his last FWB before me was VERY overweight (and I don’t see her as attractive at all), and he let slip that, as recently as a few weeks before we started dating, she could make him come. He swears he’s not frustrated or upset about it. He doesn’t masturbate after we stop having sex, he just cuddles me and we fall asleep. But it’s driving me insane. I’m doubting myself as a woman and a sexual partner, and I just feel guilty that I’ve had literally hundreds of orgasms with him and I’ve given him ZERO.

— Wild with Frustration and Confusion

Dear Wild,

If you’re having sex with this guy long enough to come 10 times, it’s safe to say he is not disgusted by you. In fact, I think it’s more reasonable to take his behavior as a compliment instead of an insult; if he’s so interested in pleasing you that he does it over and over again with no orgasm of his own, he almost certainly must be enjoying himself. An orgasm is just one thing that’s great about sex, and those who can’t or don’t climax can still have fun. Unless he’s a really good actor or for some reason living in mortal fear of you leaving him, it’s really unlikely that you’ve been having “amazing” sex with someone who really isn’t into it.

Hopefully that framing will help you to not take his performance so personally. The fact is that several factors may be contributing to his lack of orgasms with you. Erectile function tends to deteriorate over time, and maybe his boner has turned a corner during your two years together. Maybe it’s a matter of him not getting the very specific stimulation/pressure on his penis that he typically needs to come, and he’s too bashful to say anything about it. If he’s perfectly content with the way things are, you’re better off not worrying too much about it and taking the orgasms he’s giving you. If it continues to bother you, have a conversation about it—without pressuring him into discomfort, see if he’ll be more specific about his feelings. All I’m getting from you is what he doesn’t feel about his weak erections and lack of orgasms—frustrated and upset. What does he feel? Does he enjoy sex for what it is beyond a means to get off? Is there anything you can do to help facilitate his climax? Has he looked into E.D. treatment?ADVERTISEMENT

It’s understandable that you want to aid your partner in achieving orgasm. Making people feel good feels good. But you should ask yourself what you will do if it simply isn’t possible. Can you adapt to the idea that you’re coming buckets next to a dry guy? If not, this just might not be the right relationship for you.

Dear How to Do It,

Could you recommend any books and resources for exploring ethical non-monogamy as a team activity? I’ve seen a lot of resources on polyamory/open relationships, but that’s not what we’re looking for; we’re really just interested in navigating group sex/swinging as a couple exploring together. I’m a nerd, so anything involving worksheets or practical discussion exercises would be great. (We’re a straight cis woman and a bi cis man, if that has any relevance.)

— Trying to Do It Right

Dear Trying,

It’s hard to prove a negative, but in my research, including checking in with some experts, I’m not sure that exactly what you’re looking for exists, per se. Of course, you can make any book a couple’s book by reading it at the same time as your partner. There are classics of the nonmonogamy genre likeThe Ethical Slut. Tristan Taormino’sOpening Upcontains several exercises and checklists that might scratch your nerd itch. There are also jealousy workbooks that you could, in theory, go through together (I haven’t tried out either of those workbooks, so consider this a heads-up and not a full-hearted recommendation).

Your sign-off makes me think you’re looking to be walked through the process of group sex/swinging, but that’s going to look different for everyone depending on where you are, what you’re looking for, and especially, how the pandemic is affecting whatever scene you’re trying to penetrate. Once you find a group of swingers or likeminded potential partners, the mechanical stuff should unfold pretty straightforwardly—what’s going to be more important is to stay on top of is the emotional stuff, which the poly/open relationship sources you mention that you’re not looking for will help facilitate. However, you might also want to look into the offerings of John and Jackie Melfi, who run lifestyle clubs and publish a lot of open-relationship content on their OpenLove101 website, including a newbie’s guide to swinging and a conversational video series that explores open relationships from various angles. The Melfis have been at it for a long time, and John tells me via email that they also offer online an in-person relationship coaching, in the event that you and your partner need tailored guidance.

Dear How to Do It,

Does a guy know which hole he’s trying to put his penis into? I’ve been sexually assaulted by four different men, all in my late teens through my 20s. I believe I am on the autism spectrum and have a history of trusting the wrong people. I’m 40 now (and remarried to the kindest man I’ve ever met) and am realizing how much that trauma is affecting my physical and mental health. I have a lot of anger about it and a lot of work to do, but I’m stuck on something that I need a man to answer for me.

My ex-husband was generally a manipulative, selfish asshole who left me when I was diagnosed with a chronic medical condition that left me unable to financially support his video game-playing/weed-smoking/binge-drinking lifestyle. Basically, I did everything for him, but it was never good enough, from how I folded his socks and how I cooked chicken to my hairstyle and what cut of jeans I wore. But the worst memories I have are from having sex with him. He was my first and I’ve still only been with three others (consensually). I have always drawn a hard line at anal penetration. It just doesn’t sound good to me and I’ve never wanted to try it. I made this clear to him on a regular basis. He would often joke that I would change my mind or give in eventually. At some point during our two-year marriage, he started to let it slip down to the “wrong hole” and I would stop him, but it would happen repeatedly in the same act, to the point where I would sometimes start to cry. He would laugh it off and say that he “didn’t know it was down there.”

I told my counselor at the time about it, and she said that what he was doing was technically rape. When I confronted him about this, he got very quiet and promised it would never happen again. And it didn’t. So did he really not know and was just more careful after that conversation, or did he know when it was happening and just not care? It seems to me like he stopped because he was afraid of getting in trouble, not because he actually cared about my feelings. I am trying to process my anger about all of this, but this issue is creating a block for me.
Any insight you can give me will be helpful. Thank you for reading this.

— Hurt and Angry, but Finally Getting Help

Dear Hurt,

Some men are so clueless that they don’t know their ass from a hole in the wall, but I think the vast majority know the difference between other people’s anuses and vaginas. We don’t even have to do guessing in your case. Your ex expressed interest in anal, attempted to coerce you, penetrated your butt without your consent, and then he stopped when you rightly pointed out to him that he was raping you. By your account, he knew, and I think you know that as well. His ability to distort your reality and have you doubt that which you actually know is a sign of rather intense manipulation. It’s heartbreaking to read you spell things out to this extent while still questioning yourself. You were right, he was wrong, and it sounds like your life is way better without this guy. I’m glad you’re getting help, too. You have every right to be angry about this, but I hope your therapist is working with you to get to a place where you can let go. I also hope you’re working on trusting your own senses/intuition. It’s great that you have found love with a kind man—you deserve it.ADVERTISEMENT

Did you write this or another letter we answered? Tell us what happened at howtodoit@slate.com.

Dear How to Do It,

I’m a young guy, early 20s, not quite old enough to be a “grownup,” but definitely older than the kids I live around (on a college campus). And just old enough, apparently, to have actually fully followed lockdown orders and lost my entire social life to COVID, which I can see most of the freshmen on campus this year didn’t, because they stayed in school and kept going to high school parties like normal and continue to party here. My problem is that I had many dating mishaps pre-pandemic, slept and went out with people of all genders, tried a lot of different things at various parties, even identified as non-binary at one point.

Well, COVID changed a lot for me, the first thing being that I was extremely lucky to find a real partner for the first time on a dating app within the first week of lockdowns. Our relationship was pretty wild, but about seven months ago we broke up (she had terrible depression and totally lost her libido, and the anxiety it was giving me basically destroyed the relationship). After, I went out with a few more women on rebounds and hookups, but eventually I just got sick of the whole thing and stopped dating for a while. About a month ago, I was back on the apps again, furiously swiping trying to get a match, but everyone I talked to I found very boring, and after reading some very disheartening online statistics about 80 percent of dating app users being men, and seeing the profiles of friends of mine who are women, and realizing that my insecurities were being exploited for profit, I quit them entirely.

If it wasn’t already clear, I did go from being high-femme non-binary queer pre-pandemic to becoming basically a cishet man again after, and I’m experiencing all the difficulties and anxieties men have about dating women, and a whole other set of anxieties about my body—but at least I feel safer walking around at night (didn’t realize the level of discrimination until I started presenting masc again). And to top all of that off, now that I’ve quit dating apps, and don’t go to parties on campus (or even leave my dorm room very often), I have no idea how to meet people, and I’ve started to get pretty lonely sometimes since it’s not like I can just ask someone out after class or DM them on Insta (also quit social media for similar reasons) or even get someone’s Insta. I feel stuck, I don’t have “options.”

— Stuck

Dear Stuck,

You feel stuck because you are. The pandemic has put us in a limbo, and those who have made healthy connections in the past year have luck on their side. You’ll have options very soon, as things to start to re-open and people begin to reconvene. And even then, you might still have problems connecting. People do! Dating wouldn’t be the industry that it is (to some degree, it has facilitated the existence of this very column) if everything went smoothly all the time. After the initial connection is made, the probability of issues only increases from there. There’s moving the casual dating into something more serious. Then there’s figuring out whether marriage is on the table. Assuming that it is, then you will have to worry about enjoining your life to another person’s, staying connected with that person, and maintaining mutual sexual interest. The issues never stop bombarding you. If life were easy, we might have solved global warming or at least have started colonizing other planets.

But anxiety, complaining, and heartache takes up so much of our time because this shit is hard. Get used to it. You’ll grow from it. If dating apps aren’t for you, consider yourself lucky for discovering that early. (And with the time you would have been spending swiping now freed, would it kill you to look into solving global warming? We’re gonna need your generation to do that.) But if you happen to find yourself back on them, don’t think of that as a moral failure and take it all with a grain of salt. Finding and keeping love can really suck, but we keep trying because it’s worth it and even if it doesn’t seem like it, most of us are optimists when you cut right down to the bone. So chin up. You’ll be OK, and then when we can all rub on each other again, you’ll be even better.

— Rich

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May 6, 2021 / silverostrich894