...concerned that all this ass play is not healthy. As a friend, I want him to seek help for his sexual compulsion, his low self-esteem, and his social isolation. As a roommate, I am tired of all these strange men coming into my home and the high water bill.

Frequent Insertions Sincerely Trouble Someone

“Fisting is a healthy and safe sexual activity so long as the participants are sober,” said Dr. Peter Shalit, a physician and author who works with many gay men. “There is a misconception that fisting damages the anal sphincter, loosens it, and causes a loss of bowel control over time. This is absolutely false.”

Devin Franco, a gay porn star who’s been getting fisted on a weekly basis for many years, backs up Dr. Shalit. “People who are only used to vanilla intercourse are sometimes shocked,” said Franco. “People will leave comments on my videos asking if I was in pain, even though I’m clearly always enjoying it. Fisting is actually the most pleasurable sexual act I’ve ever experienced—and seven years in, no negative health consequences and everything down there works just fine, thanks.”

But exactly how does that work? How does someone like Franco get a fist and/or a ridiculously large sex toy in his butt?

“A skilled fisting bottom can voluntarily relax the anal sphincter in order to accommodate a hand up to the wrist or further,” explained Dr. Shalit. “A skilled fisting top knows how to insert their hand—it’s actually fingertips first, not a clenched fist—and how to do it gently, taking their time, and using lots of lube. And, again, after the session is over, the sphincter returns to its normal state.”

Which is not to say that people haven’t injured themselves or others engaging in anal play with large sex toys, fists, or even perfectly average cocks—people most certainly have. That’s why it’s crucial to take things slow, use lots of lube, and go at it sober.

“Fisting isn’t for everyone,” said Dr. Shalit. “In fact, most people are unable to relax their sphincter in this fashion.”

But to figure out whether fisting is for you—to determine whether you’re one of those people who can relax their sphincter—first you gotta wanna, and then you gotta try.

“It actually took about two years for me,” said Franco. “That’s from the first time I did anal play thinking, ‘Maybe I can get his whole fist in there,’ to the first time I actually got a fist in my ass. Two years.”

And while fisting isn’t for everyone, FISTS, like Dr. Shalit said, it’s very clearly for your roommate. But enjoying the hell out of a particular sexual activity—even one that seems extreme to those who don’t enjoy it—isn’t by itself evidence of low self-esteem or sexual compulsion.

“If FISTS thinks his roommate has low self-esteem,” said Dr. Shalit, “he’s done the right thing by telling him he should seek help. But that’s the end of his responsibility. Whether or not his roommate seeks help is up to his roommate. And it’s hard for me to agree that his roommate is being sexually compulsive based on what’s in the letter. Many men have sex every day, and the roommate’s sex life doesn’t seem to have any negative consequences except that FISTS doesn’t like it.”

While Franco also doesn’t think getting fisted daily is proof that your roommate is out of control, fisting isn’t something he does every day. “Doing it daily sounds exhausting,” he said. “The act requires a lot of physical exertion. I personally need a little recovery time between sessions. But I do know guys who do it every day—maybe not a fist every day, but they play with large toys every day. But I couldn’t and I don’t.”

All that said, FISTS, two of your cited reasons for not liking what your roommate is up to—strange men in and out of your apartment (and your roommate) and all that douching driving up your water bill—are legitimate complaints that you shouldn’t be shy about addressing.

“To not have a lot of strangers in and out of the apartment is a reasonable ask of a roommate,” said Dr. Shalit. “But if the roommate sees a steady stream of FISTS’s hookups coming over, it could seem like a double standard. And I suppose he could ask for extra help with the water bill, but I’m skeptical that ‘cleaning out’ for fisting would actually cause a significant increase in the bill.”

Dr. Shalit recommends Anal Pleasure & Health by Jack Morin to anyone who wants to learn more about anal intercourse, fisting, and other forms of anal play. “It’s the Bible of anal sexuality,” said Dr. Shalit.

Follow Devin Franco on Twitter @devinfrancoxxx, and check out his work at justfor.fans/devinfrancoxxx.

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My husband of nearly 20 years came out to me as bisexual about two months ago. He assured me he has no intention of looking outside our marriage for other sex partners. We’ve always had a kind of barrier sexually, and it seemed to fall away after he came out. We’ve since done all manner of things, including my using a dildo on him. (Thanks for all the tips over the years about anal!) It has been a fun and empowering experience overall. There is one thing I am having trouble with. He mentioned that he’d like me to peg him using a strap-on. I mean, of course he would, right? He’d like to actually feel my body against his. That would doubtless make the whole experience better for him. But I’m having a hard time wrapping my head around it. Does this require me, even if temporarily, to change my body? I’m feeling really vulnerable and insecure about it, like it means there’s something wrong with my body. I get panicky just thinking about it. (My husband has not done or said anything to make me feel bad about my body.) Using the dildo is no big thing, and I don’t understand why this feels so different and difficult.

Pegging Feels Different

You don’t have to do anything about this right now, PFD. Your husband only came out to you as bisexual two months ago! Your husband’s honesty pulled down that barrier you’d always sensed but could never name, and that’s wonderful and exciting. And you’re already exploring anal penetration with him on the receiving end, which is something many straight men also enjoy. If covering your genitals temporarily with a strap-on makes you feel awkward or unwanted, you don’t have to do it—not now, not ever. But I can’t imagine you think there’s something wrong with the bodies of lesbians who use strap-ons with their female partners, just as you don’t seem to think holding a dildo means there’s something wrong with (or inadequate about) your hands. If covering your vulva with a strap-on makes you feel negated or undesirable, there are dildo harnesses that strap on to your thigh, not your crotch, and could provide your husband with body-to-body closeness during penetration while still leaving your vulva and clit accessible for digital stimulation.