WWJDD: “My Boyfriend Wants Me To Peg Him! Got Any Tips?”

Editor’s Note

After multiple women accused James Deen of rape and sexual assault in November 2015, The Frisky made the immediate decision to end our affiliation with the porn star and to cancel his sex advice column with the site. In addition to believing it would be inappropriate to continue publishing sex advice from someone facing such serious allegations, The Frisky is firm in its commitment to believing and standing in solidarity with victims/survivors when they come forward. After serious consideration and input, we decided to leave the previously published columns up on The Frisky with this disclaimer, as we believe the glaring divide between Deen’s consent-focused advice and the rape allegations against him should be part of the public record. For a more thorough explanation on our decision to end this column, click here.


JAMES DEEN. You magnificent beast. My boyfriend wants me to peg him. I am nervous and was a bit apprehensive, but I want to give him max pleasure. What Would James Deen Do???

The benefit of butt-fucking someone when you have a penis is that the penis has nerve endings that allow you to feel what that asshole is doing in order create a pleasurable experience for your partner. So, before you peg your boyfriend with a strap-on, I recommend that you use something that does have nerve endings – your finger? maybe a tongue? – so you can feel what your boyfriend’s rectum and inner and outer sphincters are doing. Speaking of the sphincters, it’s really important that you also learn the anatomical structure of the anus so you know that there IS both an inner and outer sphincter and that the first one is actually really easy to get by. Anal sex hurts for a lot of people because their partner thinks that just because the outer sphincter opened they can just shove whatever in there. But about a knuckle deep in, there’s the inner sphincter, which is much tighter and much stronger than the outer sphincter, and, like all muscles, you can’t just expect it to go, you have to warm it up. So, before shoving anything into anyone’s ass, learn what buttholes do and how they do it, and then feel it for yourself by playing with your partner’s ass using your fingers or a tongue before breaking out the butt plug or strap-on and lube.

Of course, as with anything involving sex, you must have communication, communication, communication. You need to be able to talk to your partner,  read your partner, understand your partner, and you need to pay attention to different things in your partner beyond just verbal communication. Sex is an awkward thing and getting something shoved in your butt, especially for the first time, might be a really awkward thing. Your partner might need some coaxing to discuss how it feels.

Fucking someone – being the one doing the penetrating – requires a different skill set than you might be used to. (I imagine if I was getting fucked, I would be completely confused about what to do with my hips, because I’m used to thrusting.) Think about what you like when you’re being fucked and try to replicate the thrusts and rhythm, checking in with your partner about whether he’s into them too. There might be a bit of learning curve, but practice makes perfect and communication helps you grow!

Last but not least, it’s a butthole! All pegging participants should be comfortable with the fact that assholes are made to dispose of human waste and expel it from the human body. You’re going into poop’s house, get ready to encounter poop. Understanding and accepting that an asshole is not usually completely clean should be the STANDARD. If I’m going to fuck somebody’s ass, the last thing I’m going to be worried about is if their asshole is going to be squeaky clean.  There are things the peg-ee can do to make sure that their asshole is as clean as can be, if that is what they want. Some people can have a regular bowel movement and a thorough shower, and have an easy, fun, buttfuckin’ time. Others feel they need to have rigorous enemas beforehand and prepare as if they’re going to go get a colonoscopy, like not eating for a day before and drinking nothing but water. But I can’t emphasize this enough: If you’re going to be playing around with assholes, be prepared to be in poop’s house.


Already known as a porn star, actor, director, producer, sex symbol, and star of our masturbatory fantasies, James Deen can now add Frisky advice columnist to his resume. Each week in his new column, What Would James Deen Do?, he’ll be offering his straight up, rock solid, no bullshit advice to YOUR questions. Want to know what James would do? Email your questions to [email protected]!