How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I’m a 48-year-old man who’s been married for 19 years with two kids. A few years ago, I lost interest in sex, and we went through a patch where I was quite nonresponsive, but I did not withdraw my affection or engagement. We laughed, we talked, we traveled—we just didn’t have sex. That hurt my wife, and we discussed it often. While she never indicated overall dissatisfaction with our lovemaking, I have always felt that I never really measured up. She would frequently orgasm, and I am definitely in the “she comes first” crowd, but there were times when she did not, and even some of those times came with totally legitimate frustration directed toward me. We have often spoke about her desire to, in her words, “get railed.” I’ve been able to accomplish that a few times, but it is inconsistent, and even to this day, I feel like there’s disappointment.
I engaged in therapy, and for the last two years we have been rebuilding trust and intimacy, and it has been fantastic. We have been slowly building up in frequency. I still have doubts about my performance and ability to give her what she wants (more vigorous thrusting for a longer period of time). She wants me to not be in my head worrying about it and to just screw her more. Let the stamina build. If I want to come, I should just do so and not worry about her. When she wants to come, she will let me know. But I am to just get practicing and build up my strength and stamina.
I’m reasonably fit, vasectomized, not overweight, and don’t have a problem getting and maintaining an erection. So will this work? What else can I be doing? Would cock rings help? I just want to rail my wife.
—I’ve Been Working on the Railroad
Your solution seems functional—the more you exercise the muscles used in sex, the more stamina for longer and harder thrusting you’ll develop. You can also do general aerobic exercise at the gym or by running, biking, or swimming. You might feel awkward asking, but a trainer can probably show you specific exercises to do several times a week, too. And since you don’t have a problem getting and maintaining an erection, I’m not sure what a cock ring would do for you, other than look aggressively sexual.
You’ll want to experiment with positioning. Mainstream hardcore porn videos are useful here—they tend to rely on positions that are good for grabbing and vigorously thrusting into the receptive partner. Generally, doggy, spoon, and missionary with the receptive partner’s legs up are all conducive to high-energy penetration. Holding the hips seems to help. And remember to have fun with it.
Dear How to Do It,
I am a 30-year-old married mother of two. My husband works, and I stay home and manage the house and family. Most of my time is devoted to that. The only real time I get to myself is at the gym a few days a week. I love my family, and they are my world.
A few weeks ago when I was at the gym, a woman asked me out. I didn’t know what to say and just told her I had to think about it. Honestly, I am curious. I had been kinda dating a woman in college, “Jess,” before I got pregnant and married my husband 12 years ago, and I often wonder how it would have gone if I had been able to continue on with Jess. Those thoughts have been on my mind for a few years now.
I am honestly thinking about taking this woman up on her offer. She is very attractive, and we have been flirting the few times we have run into each other at the gym. She is five years younger than me and single. I do like her and think of her a lot.
I am at the point in life where I don’t want to live with regrets. I do sometimes wish things had been different with Jess and feel like I don’t want to make that mistake again. But I know my husband will not be OK with it. I do love him and don’t want to end our marriage. I think I just want to explore this side of my life more. I know something like this will affect the kids too, so I am worried about that. How do I explore this part of me and not hurt the ones I love?
Dear Hard Situation,
You say you know your husband wouldn’t be OK with you having a sexual relationship with a woman. Unless you’ve already asked in a direct, clear manner, you should do that to make sure. If you’re correct and you don’t want to hurt him, much less end your marriage, you don’t get to explore this side of your life. Sometimes, we don’t get to have everything. If you decide to explore anyway, your husband will be hurt, and your marriage may end.
You have a difficult decision, and I can’t make it for you. Which do you value more: stability or adventure? Known partnership or exploration of your sexuality? In your case, it really is a binary choice. Make some lists of pros and cons for each path—somewhere private, like a password-protected phone—and consider talking with a therapist for a few weeks before you make any large changes. Good luck.
Dear How to Do It,
I’m a bisexual man who is happily and monogamously married to an amazing, open-minded woman. She knew I was bi (and mostly dating men) when we started dating, so it’s not an issue (and honestly I think it’s something she likes about me). Recently, though, I’ve been craving a good ol’ fashioned ass-pounding, so I’ve been curious about introducing pegging into our repertoire. She has minimal hangups, so I don’t anticipate pushback, but she’s never seemed very comfortable being anything other than a pure bottom. How do I make this little feminine creature feel sexy on top? Also am I naïve thinking this experience can be a close enough approximation to being with boys to scratch my itch, or am I better off adapting to life without it?
Dear Nostalgic Bottom,
Dildos might be close enough to penises, and they’re easy and low-cost enough to try. Worst-case scenario you’ve got a flared-base dong and a harness to dispose of. Note that I said flared, so that it can sit securely in a harness and not slide through. A decent harness is crucial, too. I’m partial to the SpareParts Tomboi, though I’m not the world’s most frequent strap-on user. It’s very snug, so the wearer has greater control over and connection to the cock. Read some reviews, pay attention to measurements, and visit a sex shop to try harnesses on if possible.
Unless submission is part of your ass-pounding craving, she can bottom from behind. You can verbally direct her, praise her, even demand of her, depending on your interaction patterns and her preferences. You can also have a conversation about topping. Is there anything she’s curious about? Is there any piece or thread of it that feels interesting to her? That’s something to build on. Even if you don’t turn up any points of entry, it’s still nice to have these talks.
Dear How to Do It,
My girlfriend and I are both women in our late 20s and have been together about a year. A few months ago, we discovered the euphoria of having simultaneous orgasms. We first got it while kissing during mutual fingering and later, with practice, have been able to do it while scissoring as well. Maintaining eye contact helps us to talk and read each other while doing it and adjust our pace to get there together. It’s a fantastic feeling, and now we are getting it consistently in these positions.
However, we still haven’t been able to achieve this during 69, which is quite frustrating, as we very much enjoy doing it that way. Either she or I will orgasm first, which breaks the rhythm for the other. We’ve tried talking or giving directions while doing it, but hearing a voice from the crotch was quite a turn-off. We’d love to have that feeling of coming together in a 69. Any thoughts or ideas?
—Trying to Sync
Dear Trying to Sync,
This is great and beautiful, and I’m thrilled for both of you. I’m thinking the eye contact might be a crucial part of your ability to synchronize, and you may be asking for more than is possible. A metronome might be worth a shot? It isn’t 69ing, but you might enjoy doing breathwork together and it may help develop the awareness and synchronization that I suspect are allowing you to come together. Barbara Carrellas’ Urban Tantra is a great place to start for that. Enjoy!
More How to Do It
I have a wonderful boyfriend who is very sexually generous (goes down on me, asks what I like during sex, etc.) but for one thing: He totally avoids me during my period. We don’t touch, kiss, and he doesn’t allow me to go down on him because he says he doesn’t want to be selfish. I’ve asked him what I can do to make him more comfortable and he says he just needs time because he’s always been “grossed out” by the blood and has never engaged in period sex with anyone. Because of the pill, I barely have a flow, and the little there is is still too much for him. For context, we are in our 30s and talking about marriage, and I am a little impatient at thinking of a future with 25 percent of the month off the table for sex. I don’t want to nag him or pressure him, but is there anything I can do to make him more comfortable with some (any!) contact during this time? It makes me feel self-conscious and undesirable.