A Round Peg in a Small Hole

Welcome to The Frisky Feminist, Persephone Magazine’s resident sexpert couple’s advice column answering all your sexuality related questions with honesty, enthusiasm and humor.   Content below the cut may be considered NSFW, so proceed at your own risk.  ~ed

Q: What is the best way to broach pegging with a new guy? Do you wait for him to bring it up? What can I say that won’t freak him out?

Before we answer – you’re not reading this at work, are you? Because, fair warning, there will be a picture of a dildo.
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What a perfect first question to get. We’re both huge fans of pegging, which, for readers unfamiliar with it,  is the term coined by Dan Savage for the practice of a woman fucking a man with a strap-on. While it’s a very (very) enjoyable practice for us both, it certainly took some working up to.
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Have you and your partner explored any other kind of anal play together? Going from no contact at all to strap-on sex may be a little sudden for him, both physically and mentally. If you haven’t, it’s a subject to bring up gradually, especially since he may not think he would (or should) enjoy it. We both feel strongly that, to put it bluntly, you shouldn’t stick things up someone’s ass without permission, but you could let your fingers drift to his ass during other activities and see if he reacts positively to very gentle touching or stroking. If he does, you can venture further with some sort of verbal confirmation – ask if he likes it, and if you get a yes, proceed to apply a little more direct pressure and stimulation. (Make sure your nails are trimmed – Mr.)
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It’s that first foray into anal play that’s the most difficult step; after that, you will be able to broach the subject of pegging a little more directly. You can ask him flat-out if he’d like you to fuck him in the ass; if you think he’d be hesitant, there are plenty of other anal activities you can explore together first, like fingering (Lots of lube, and a condom over your fingers can help keep things smooth for him and make you feel better if you’re concerned about poo, which I was at the beginning – Ms.) and other toys, like a small butt plug or a vibrator.
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See, we told you.
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If you’re both enjoying yourselves, you could bring it up while you’re doing one of these other things – he’ll be very aware of how much pleasure he gets from similar activities and may feel less inhibited than if you bring it up before or after sex. (You may also try playfully humping him from behind in the shower or while you’re snuggling and see what happens – that’s how I first became interested in the possibility of pegging and based on his very positive reaction I knew he’d almost certainly be into it too. – Ms.)
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It may also be helpful to think about exactly what about it makes you think it might freak him out. Hygiene? (Poo?) Pain? Some men get a bit squeamish about anal play because they think that only gay men are interested in receiving it; remind him that it’s not the activity but the person doing it that might say anything about his orientation. There’s a woman on the other end of that cock, after all. If he tends to be more dominant in bed, there are plenty of positions that will allow him to take the lead and be in charge of things; if he tends towards the submissive side, pegging certainly provides ample opportunity for you to be in the position of power.
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Once you’re both past any hesitation and ready to begin, the same rules apply as for anal sex with an actual penis doing the penetrating. Start with a single finger until he feels relaxed enough for more, use a condom, and use plenty of lube. (If you think you’ve got enough on there, you don’t. Add more. – Mr.) Position and angle are everything. Small changes, like if he bends his legs and where he holds them, can make a big difference. And don’t expect to immediately be great at it – like with any new sexual activity, it gets better with practice and will likely be a bit awkward the first few times. (I thought that I’d immediately be able to go at it like a porn star, but it took some figuring out what were good positions for him and what kinds of movement for me worked well – thrusting is hard work. – Ms.)
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Got a question you’d like us to discuss? You can e-mail us at FriskyFeminist@persephonemagazine.com, and we’ve also set up a Tumblr for the sole purpose of receiving completely anonymous questions at paperispatientsexqanda.tumblr.com.

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paperispatient

I recently earned my MA in women’s studies. I enjoy reading, working out, playing Scrabble, watching cheesy movies, and cooking yummy vegetarian meals with my partner and Frisky Feminist co-author, Future Mr. paperispatient.

2 thoughts on “A Round Peg in a Small Hole”

  1. >>>Make sure your nails are trimmed — Mr.

    Dear sweet God yes. I was on the receiving end of some anal fingering once and the lady friend that was doing it didn’t trim those bad boys. It felt like I was getting boned by a knife.

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