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Dear Ashley, a weekly sex column in which sex expert Ashley Cobb answers your most intimate questions. Nothing is off-limits!  Have a sex question, Ashley, “Your Favorite Friend In Filth,” has an answer. For questions on sex, email Ashley at ashley@sexwithashley.com

 

Dear Ashley,

I want to peg my boyfriend. I became interested in pegging after my sister told me she pegs her husband. I was really surprised because her husband does not seem like the type who would be into taking it in the ass! I always thought only bisexual men would be into pegging.

My sister said women pegging their men with strapons is more common than I think. She also said most men are embarrassed to bring it up and that I would probably have to bring it up first. She told her husband she wanted to fuck him and that it was a fantasy of hers, then added that she would understand if he didn’t want to let her. The trick, she said, is to make it your idea so he will go along with it because it’s something you want. A few weeks ago, I took my sister’s advice and told my boyfriend I thought pegging him would be an incredibly erotic and intimate experience. he chuckled and said, “maybe in the future.”  Since then, I’ve occasionally joked about it, and even tried to stimulate his perineum–the area between the anus and the balls,  but he seems apprehensive about going all the way.

What are some ways I can make him feel more comfortable? How do I get him to go all the way? Any advice would be appreciated.

 

Hey Girl Hey,

Your sister was right about one thing. Quiet as it’s kept, women are indeed out here fucking men in the ass.  Pegging, according to Health.com is an sex act in which a female partner penetrates her male partner’s ass with a strap-on. Like you, there  are still a lot of people who think men who enjoy a dildo in the booty must be gay. This is false. Wanting to be pegged doesn’t have anything to do with being gay at all. In order for sex to be categorized as “gay” or a homosexual act it needs to include two people of the same gender. Any sexual act performed between a man and a women is heterosexual. That includes pegging. 

I’ve never pegged anyone a day in my life, but my friend has. My friend, who I’ll call Tasha, once told me she experienced one of the best orgasms of her life, pegging her then boyfriend. She said the power exchange was exhilarating, and hearing her man moan with pleasure from her thrust made her pussy wetter. I won’t lie. After she told me this, I was like damn, I gotta find a man to peg because I need to experience what Tasha felt. Unfortunately, I haven’t been so lucky, but it’s still on my bucket list.

Though I have no personal pegging experience, I have experience with men. I have had sex with men my whole adult life, so I’ve learned a thing or two along the way about how to approach men on non-vanilla sexual topics. How patient are you sis?

You’re going to have to slow walk this thing. Men tend not to be as “adventurous” in the bedroom as women. I had men tell me they were freaks only to discover that their definition of freaky included eating pussy and putting a finger in my ass. Some men can be very conventional and quite boring in the bedroom. Society has taught them that they can’t explore their sexuality in the same way women might be able to. So, the apprehension you are getting from your boyfriend is completely typical. He doesn’t feel comfortable and being pegged will require a level of vulnerability on his part. The best advice I can give you to help your boyfriend be more open is to communicate. You’ve shared your reasons for wanting to peg, but what are his thoughts on it? Ask him his thoughts on being pegged. I mean it is his ass.  His response will give you better insight. More importantly, whatever his reasoning, it’s imperative to respect his boundaries. He could just not be into pegging, and that’s okay too, respect that. It isn’t our job as partners to convince or force our lovers into any sexual act they don’t want to perform. After you two talk, he may need time to think. Respect that and give him space and time to gather his own thoughts. Some of his apprehension could stem from the myths associated with pegging. If so, you guys can debunk those together. Talk, listen and then let him assess if pegging is truly for him or not. 


Ashley Cobb is the millennial microphone that brings the conversation of Black women’s pleasure to the forefront. Creator of digital platform Gossip And Gasms, her work and words have been featured in Cosmopolitan, Men’s Health, Shape Magazine, Business Insider, and Huffington Post. Follow her on Instagram and Twitter via @sexwithashley

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