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Let Us Sex-plain: How do I introduce my boyfriend to butt stuff?

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York

Written by
Jillian Anthony
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I get it—being single in the city can be tough, and the ways New Yorkers are having sex these days can be surprising. But whatever your dating conundrum might be, I'm here to help. Consider me (Jillian Anthony, Time Out New York's Senior Things to Do editor) your personal wingwoman, guiding you through dating and doing it in New York in our weekly "Let Us Sex-plain" column. Check out my answers to all your questions online and in the magazine every Wednesday, and submit your own coitus queries below!

How do I introduce my straight boyfriend to butt stuff? He’s never done it before and is a little resistant.
—Alyssa, Industry City, Brooklyn
Straight men of the world, say this with me: “Masculinity is a prison!” It’s 2016—time to let go of any last threads of homophobia and gender norms you’re holding on to! Everyone has an asshole, and we can all enjoy them to the fullest, regardless of sexual orientation. (Guys, if you’re having anal sex with your girlfriend, it’s only fair that you keep an open mind if she wants to switch roles.) Men have the most to gain from anal action because they have a prostate gland, the male equivalent of the G-spot. Enjoying a finger or a dildo back there now and then won’t turn you gay (literally nothing will—sexual orientation is something you’re born with, like brown hair). In fact, it might take your orgasm to a level you’ve never experienced. Alyssa, tell your boyfriend a variation of the above, then start small; rub a nicely lubed finger around the edge of his anus, and once he relaxes, explore inserting your finger inside, slowly. If this is a hit (I bet it will be), try a rim job (your tongue, his anus) next. And if you’re ready for the boss level, try pegging: Use a strap-on to bone your boyfriend. You’ll likely find that it really is as fun as the ladies of Broad City make it out to be.

I’ve been hooking up with a married guy who says he’s in an open relationship, but I’m worried that he’s lying. How do I know if I’m the “other woman”?
—Brian, Soho
An open relationship doesn’t usually involve bringing your trysts home to meet your husband. Every open relationship comes with its own set of rules—“Don’t ask, don’t tell” and “No boning other people when I’m in the house” might be a couple of them. If something about the situation isn’t sitting right with you, voice your concerns and ask what the deal is.

My boyfriend prides himself on being an open book, but all too often that book is open to a page about the details of our sex life. I’m much more private when it comes to telling friends about our intimacy. How can I politely tell him to shut the fuck up?
—Cameron, Tribeca
We all know this guy—you’re having a beer and discussing the new season of House of Cards, when out of nowhere Chatty Chandler says, “So Cameron and I tried [insert kink here] for the first time last week. Let me tell you about it in shocking detail.” I’m all for talking openly about sex—I don’t think my friends and I talk about much else, besides RuPaul’s Drag Race—but if your boyfriend is sharing things you’re not comfortable with, he needs to cut it out. Sit him down and say, “When you talk about our sex life with other people, it makes me very uncomfortable.” Then lay down some ground rules so he understands what your boundaries are, like “Don’t bring up my body parts unless I do.” You should only have to tell him once.

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