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My boyfriend and I both spent a lot of time masturbating when we were young, and pretty much trained our brains to come only one way. He can only come from masturbating furiously, or sometimes from a marathon of jackhammer sex. A few years before I met him, I toned down the masturbating to retrain my brain and pussy and tried a bunch of new things, and I can now come from different acts and positions. It wasn’t easy, but I am so happy with this versatility. I’m starting to get annoyed that he isn’t working harder to overcome this jackhammering reliance. It hurts, it’s super boring, and it makes me feel like I might as well be an inflatable doll. We’ve talked about it, and he says he’ll masturbate less, and that does help (read: Now it’s a half hour of jackhammering instead of hours), but I’m still eager for more variety—and to be able to walk after sex and ride a bike the next day. For what it’s worth, about half the time he just lets me come buckets and then gives up on himself. Can you recommend anything that would help him? Since I know firsthand this can be overcome and I accommodate him as much as possible, I think I’m being reasonable, but I’m sure you’ll tell me if I’m not. —Hoping A Massive Masturbator Eventually Retrains Exacting Dick
Here’s how you retrain his dick: Your boyfriend stops doing what he’s always done—no more masturbating or fucking in the style to which his dick has become accustomed—but he keeps on having sex and he keeps on masturbating. But he is not allowed to revert to jackhammering away at your pussy or his fist if he doesn’t get off. If he doesn’t come, he doesn’t come. Eventually his dick, in desperation, will adjust to newer, subtler sensations, and he’ll be able to get off without jackhammering.
Some guys can retrain their dicks—and some women can retrain their pussies—but some people have carved too deep a groove into themselves and their junk. Other people really do require intense stimulation—jackhammers and death grips and powerful vibrators—to get off, and they have to figure out how to incorporate that intense stimulation into partnered sex without destroying their partners’ orifices. But the only way to find out if your boyfriend’s dick can be retrained is to try and retrain it. The fact that masturbating less cut his jackhammering down from hours to half an hour is a positive sign. —Dan Savage
Oh god, Dan! Help! How do I get over my jealousy over my bisexual boyfriend, who now wants to act on his urges for women? We’ve been together and had a happy gay life for 15 years, open with men for only three of those years. He has integrity, and he says he would never cheat on me, but he’s getting to the point where he is gonna hook up with women, whether I am okay with it or not. There’s more to it, though. He is perfect in every facet of his life. A perfect person and a gift to the world, so any woman would be crazy not to want him for herself. We are deeply in love, but I’m afraid of a woman’s ultimate intention for a guy like my partner. —Jealousy Annoys Gay Guy
Gay and bi men are just as interested in having partners who are perfect in every facet of life, JAGG, and yet you trust your boyfriend to fuck other guys and come home to you. You’ll just have to trust your gift-to-the-world boyfriend to do the same with women: fuck a woman now and then but come home to you after. The “ultimate intention” of whatever woman your boyfriend fucks should concern you less than your boyfriend’s ultimate intention. Does he ultimately intend to stay with you? Or would he ultimately prefer to be with someone else? If he wants to stay with you—and he’s likelier to wanna stay if being with you doesn’t mean he never gets to have sex with a woman ever again—then you’ll have to trust that your same-sex relationship is strong enough to withstand a little opposite-sex hooking up. —Dan
I’m a 25-year-old heterosexual female, and I’ve been in a long-term friends-with-benefits relationship for a little more than four years. My FWB partner and I have recently decided to move from being FWB to actually dating. The issue is that we’ve both become so accustomed to the late-night sexting-and-hookup routine that going on dates seems awkward and forced. It doesn’t help that neither of us has been in a relationship before, so we both feel a little in the dark on how to navigate this. I really do like the guy (and our sex life is amazing), but I’m not sure how to move past the in-between phase we’ve found ourselves in. Have we been in FWB-land too long to come back? —Lost In Datingland
Dating is what people do before entering into a relationship—or it’s what most people used to do—and you two are already in a relationship. It was a FWB relationship, yes, but it was still a relationship. And people in relationships don’t typically go out on dates. So, yeah, the reason going out on a date with your boyfriend feels awkward is because you’re not dating, LID, not at this stage. You’re together. So be together: Go places, do things, have dinner, see friends, go home, sex amazingly. Spend more time together, build on what you’ve already established, (i.e., the emotional and sexual connection that carried you through the last four years), and stop stressing about performing the roles of “boyfriend” and “girlfriend.” —Dan
Recently, while masturbating, as I was approaching climax, I had a sharp pain in my abdomen. It felt like my intestine wanted to burst though my abdomen, kind of like a hernia. It really sucked and it ruined my orgasm. This has happened a handful of times in the past. I mentioned it to my doctor once, and I tested negative for a hernia. I’m a 52-year-old male in reasonably good shape; I’ve been going to the gym on the reg for the past few months. This sucks in that when my wife and I play, part of it involves my wife putting me in four-point restraint, masturbating me, then tickling me post-orgasm. It would really suck for this to happen while tied up and has me concerned about our sex play. Advice, an explanation, or a good theory would be welcome. —Gut Ruins Orgasms, Addling Nerves
I would advise you to speak to your doctor, GROAN, but I don’t think you should worry about this too much. And I would theorize that you tense a particular muscle or set of muscles when you masturbate and every once in a great while this muscle group revolts and spasms painfully; your return to gym-going may have contributed to your most recent spasm.
So long as your doctor gives you the all clear, GROAN, I don’t think you should stop going to the gym—or masturbating or letting your wife tie you to the bed. Risking the occasional spasm, however painful, seems a reasonable price to pay for regular orgasms and adventurous sex. —Dan