©2012 LaRae Lobdell

I’m a gay man who is ready to start cheating on my boyfriend. We’ve had a wonderful 3.5-year-long relationship full of respect, affection, support, and fun. I love everything about our relationship, and our sex life was great… until he moved in eight months into the relationship. At that point, he lost all interest. I’ve tried everything: asking what I can do differently, being more aggressive, being more passive, suggesting couples therapy, getting angry, crying, and breaking up twice. (Both breakups lasted only a few hours because I honestly don’t want to leave him.) When I bring up an open relationship, he just goes quiet. I’ve moved past most of the anger, frustration, hurt, embarrassment, and sadness. But I won’t accept a life of celibacy. I would like to get some discreet play on the side. My boyfriend is very perceptive, and I’m a bad liar. I don’t want to get caught—but how should the conversation go if (when) I do? I’m leaning toward something like this: “I’m sorry it came to this and I know we agreed on monogamy, and I gave you monogamy for 3.5 years, but part of agreeing to monogamy is the implicit promise to meet your partner’s sexual needs. Everything else about our relationship is wonderful, but we couldn’t fix this one thing, so instead of continuing to push the issue, this is what I decided to do.” Good enough?

Can’t Help Exploring Another Tush


The speech you’re planning to give after you get caught is lovely, CHEAT, but you should give it before you get caught. Tell your boyfriend you love him—you would have to, considering what you’ve put up with for nearly three years—and that you have no desire to leave him. But while your relationship is wonderful in many ways, it’s not sexual in any way. And while you’re willing to settle for a companionate relationship, you’re not willing to settle for a sexless existence.

Rather than being threatened by your occasional, discreet, and safe sexual adventures, CHEAT, your boyfriend should be grateful for them. Because those sexual adventures, and your boyfriend’s acceptance of them, will make it possible for you to stay together. Hopefully he’ll see that the men you’ll be fucking on the side aren’t a threat to your relationship but its salvation.


If your boyfriend can’t see that, if he insists that your relationship remain monogamous and sexless (wouldn’t that technically mean he’s the only person you don’t have sex with?), give breaking up another try. The third time might be the charm.

I’m a woman in a hetero marriage. My husband and I enjoy skimming the Craigslist “casual encounters” section. It’s like people-watching, but NSFW. We recently stumbled on an ad posted by a male friend. The ad was soliciting gay mutual BJ/HJ, with the stipulation that the first one to come (the loser?) gets fucked in the ass by the other (the winner?). Other than the concept of winners and losers during sex, I’ve got no issues. The thing that gnaws at my conscience is this: Our friend is a young guy, bi-curious, and impulsive. Once I got over the giggles of glimpsing a dick pic that was not intended for my eyes, I began to worry about our friend’s risky behavior. Do I say something? I care about this guy, but I don’t want to come off as “mommy” or “creepy.”

Dude’s Extremely Risky Plan Elevates Stress


My first impulse was to tell you to mind your own business—or MYOB, as the late, great Ann Landers used to say (Google her, kids)—because you don’t actually know if your friend is taking foolish risks. He could be using condoms, taking Truvada, and carefully vetting his play partners. But if I spotted a friend’s dick on Craigslist in an ad that left me the least bit concerned for his safety, I would say something. I don’t mind coming off as “mommy” (meddling mommy impulses are a requirement for this gig), and if looking out for your friends is “creepy,” then I’m a creep.

I’d go with something like this: “I spotted your ad—and your cock—on CL. What you’re looking for sounds hot. But I hope you’re being safe: using condoms, being choosy, taking Truvada. And speaking from experience, getting fucked right after you come sounds sexy in theory, but it’s not much fun in reality. So I hope you’re taking a refractory-period-length break—maybe for ice cream?—before the loser gets fucked.”


I’m a gay man in my late 20s, and I can’t get fucked. I have tried to train my ass, but the largest thing I can place inside remains a small butt plug. If I try anything bigger, the pain is unbearable. I’ve always been a very anxious person, and it’s clear my anxiety goes right to that area. Sometimes, after trying to place something larger inside me (using tons of lube, of course), I will get a hemorrhoid. Since those are horrible to deal with, I think my mind has started to associate any type of anal play with getting hemorrhoids. The problem is that I feel like I’m a bottom. Yes, I will top guys, and I don’t mind it, but I find that the men to whom I’m most attracted want to fuck me, which is something I would like. I’m at my wits’ end because I feel like my relationships/hookups/FWB situations are all negatively affected by my inability to get fucked.

Determined Efforts Fully Enrage Anal Tissues


“Anxiety and fear can definitely make those muscles tighten up. And unfortunately, worrying about pain during sex makes it worse,” said Charlie Glickman, sexuality educator and author of The Ultimate Guide To Prostate Pleasure (www.makesexeasy.com). “His hemorrhoids are probably caused by the anus squeezing really hard and trapping blood in the arteries inside the anus.”

So what can you do to alleviate your anxiety, fear, and squeezing? “The first thing for him to do is use a salve on the skin around and inside the anus,” said Glickman. “Apply it after washing, and it doesn’t take much. It’s like putting lip balm on dry lips. Cocoa butter or coconut oil work well. I also like the golden seal and myrrh formula by Country Comfort. Apply it twice a day.”


Give those balms some time to work before you start exploring again. And once you start: breathe deeply, take it slow, and play with your cock too. “Arousal helps,” said Glickman, “so he should be sure to include cock pleasure before going near his anus. It’ll also help if he explores external anal massage without going inside. That can help his body unwind the tension and let go of the flinch response. There are lots of great external massage moves that can feel amazing on their own or as part of foreplay. Look for the anal massage how-to videos on eroticmassage.com.”

Enjoying a few dozen—or a few hundred—orgasms with your ass in play but not the focus, i.e., your ass is being stimulated but not penetrated, DEFEAT, and you’ll begin to associate anal stimulation with pleasure and victory, not pain and hemorrhoids. Then you can give penetration another go: taking time to warm up, using lots of lube, pivoting to something else if it’s too painful.


Follow Charlie Glickman on Twitter at @charlieglickman.

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