Dear Dan: 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 wit’s 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
Dear DEFEAT: “Anxiety and fear can definitely make those muscles tighten up. And unfortunately, worrying about pain during sex makes it worse,” says 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,” Glickman says. “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,” Glickman says, “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 @charlieglickman.
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