BoyButt Cherry-Bustin' Delight

Dear Leah,
I'm almost too shy to admit this, but I am a guy who is interested in anal sex. But not the kind where my penis is inside someone else. I'd like to be penetrated. I haven't approached my girlfriend with this yet, I'm not sure if she'll be interested. What do you think is the best way to bring it up?
Edmonton, AB


Dear Excited,
Congratulations for acknowledging your desire for anal pleasure. The anus is one of the most sensitive erogenous zones we have. And contrary to the stereotype men aren't interested in it, the truth is many men are. And not just queer dudes, either!.
So why don't they just ask for what they want? It's often some combination of homophobia (particularly for straight men), a concern that wanting anal attention is inherently deviant, and good-old fashioned fear about raising one's deepest sexual fantasies.
Sex workers who provide back-door action as part of their services will tell you this is their most-requested service—the one that takes clients longest to work up the nerve to ask for, and that they are most unwilling to ask of their wives or lovers. While that might be good for an escort's bank account, many urge their clients to be open with partners about what they want, as many men feel guilty about their infidelity. After all, if you're considering spending the rest of your life with someone, doesn't it make sense to at least ask if they're into it? Sadly, most are too afraid to take the risk.
In a situation like yours, there are two questions to consider. First, are you ready to talk about your fantasies. Second, is your partner ready to hear them.
If this was a desire that came up once in a while, but wasn't particularly urgent, it would be fine to keep it to yourself—but it seems more important than that. I would prepare for your discussion by considering how it would feel for you if she reacts badly, particularly if it reinforces something you're already strugging with (e.g. that it means you're queer, or is immoral).

Have you had conversations before about fantasies? How have they gone? If she's reacted negatively in the past, she may now, too, so you need to take that into account. Quite frankly, if she's consistently reacted in dismissive ways to suggestions of sexual exploration, it's unlikely she'll react differently now. In that case, you may want to consider whether you are well matched. While there is more to a relationship than sex, if exploring this form of sexuality is a 'must-have' for you instead of a 'would-be-nice', you need to consider this seriously.
If you're the one who has been shy about raising it, despite openness to adventures on her part, test the waters by letting her know there is something you're interested in exploring, but you're afraid she might judge or reject you. Pick a time to talk when you're both relaxed and free of external demands and when you're not in bed. That way she's less likely to feel you expect her to explore it immediately, and more like it's truly something you want to discuss before actually trying it.
Take time beforehand to think through where you're at, too. There are a lot of ways to have anal sex, including rimming (anal–oral sex), external and internal fingering, vibrator, butt plug and dildo play and finally, use of a strap-on harness and dildo. Keep in mind it's cool if you're not certain until you try it—just be honest about what you do know.
If she is interested enough to spend more time talking about what turns you on about it, be prepared to share what you're ready to explore now versus what you'd like to check out once you know more. Depending on where she's at, her reaction could range from an enthusiastic "Hell, yeah!" to needing some time to think it through. Remember, it's fine to remind her this is new for you, too, and you'd love it if you could explore it as a couple, together. In fact, you could check out The Ultimate Guide to Strap-On Sex or The Expert Guide to Anal Pleasure for Men for some high-quality tips'n'tricks from the experts.
Excited, I wish you all the the best in raising this with your gal. I'm crossing my fingers and toes that all goes well, and that the two of you find yourself floating on a wonderful cloud of boybutt-cherry-bustin' delight!

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