Asking for a Friend is a weekly sex and relationships column hosted by Arts and Culture writer Dana Sparks and fueled by your curiosities. Click here to anonymously submit questions regarding sex, relationships and sex education. 

Question: “I’m not homosexual, but how do I tell my significant other that I want to be pegged?” — Peggy

Answer:

Dear Peggy,

First things first, I need to explain what pegging is for all the folks out there who don’t know.

Pegging is when a woman anally penetrates a man using a strap-on dildo. Now, this is very gendered language, and I would imagine the definition adjusts itself accordingly to one’s identity as long as the key ingredients are involved.

But I want to address the first part of your question because — pegging or no pegging — there is a huge misconception happening and I think that it really holds a lot of people back from chasing after their best pleasure.
Anal sex is not just for gay men and wanting anal sex as a man does not make you gay.

I recently heard on Dan Savage’s “Savage Lovecast” that 25 to 30 percent of gay men don’t even have anal sex. Isn’t it wild how wrong our culture’s sexual narrative is sometimes? We don’t have to allow our gender to dictate our sexual behaviors and vice versa.

What makes someone a gay man is when he himself decides he is gay — that’s true even in a scenario where he only has sex with other dudes for his whole life.

Our sexual identity is something that we should use as a language to express ourselves and explore others with — not limit ourselves. If you engage with your need to disclose that you aren’t homosexual, you might find yourself confronting what you’re really avoiding in the process.

With that being said, I’m really psyched that you reached out to me about wanting to get pegged. I’ve been eagerly awaiting an opportunity to talk about this because it opens up a whole world of excitement, especially if you and your significant other are both new to the possibility.

What the second half of your question boils down to is you wanting to push the boundaries of your sexual experience; you’re asking someone to take on a new responsibility with a sensitive part of your body, and there’s emotion involved.

The reason I brought up your distinct disclosure about not being gay is because it signaled to me a potential worry of yours that someone will think that you are — and if you are perceived that way, there’s something wrong with you. Or you’re less of a man. If anyone thinks that wanting to experience anal stimulation makes you gay or affects your masculinity, I would recommend cutting that person out of your life.

This includes your girlfriend. By asking her to peg you, you’re putting yourself out there — you’re stepping out of the conventions of hetero sex — and by that you’re risking rejection. If she rejects you, tells you that’s gay or anything that makes you feel shame for your sexual pleasure, you might want to reevaluate your relationship with her.

That’s nerve wracking, so step one is the emotional set-up. Relax; have faith in your relationship and confidence in yourself. Remember that allowing yourself to be vulnerable is one of your greatest powers in a relationship.

You might think of this next part like this: if you want to receive, you might have to give a little first.

Start the talk by checking in with her about her own sexual pleasure. Is there a way that you can make her more fulfilled? Is she longing to try something new?

When your significant other answers, really listen to her. Ask her to explain how you can be an active player in her pleasure.

Hopefully through her sharing with you, you can begin sharing with her. It could be as simple as saying, “I would like to experience a prostate orgasm with you.”

This gives you the opportunity to explain more and for her to ask questions (How do you want to do that? When do you want to do that?). Just like sex, a conversation is a process of sharing.

Explain to her that it feels amazing because the prostate is the g-spot of the typical male anatomy. Tell her that experiencing that with her would be exciting. Tell the truth.

If this is something that you want from her, you need to support her in that learning process — hype her up! I don’t know what her sexperience is like, but consider that she might not have used, or even worn, a strap-on before. She’s not going to be feeling physical sensations through the dildo like a person with a penis would, but rather by her own movements that are creating your pleasure. That could be a very sexy and empowering experience for her.

Together you can pace learning the proper foreplay — because you’ll both need it — and learn how to use your new toys. You might want to share with your partner that there are special strap-ons and dildos out there that were created especially for women and female-bodied people. For example, some strap-ons have pockets for vibrators and there are dildos that have a specially designed base that provides clitoral stimulation for the person wearing the harness.

I am so excited for you, and I hope that this opens up new, sexy opportunities for you both.

Yours truly,

Dana

P.S. You are not the only person writing to me about anal sex — hopefully more content related to your question will follow!