Go Ask Alex: Straight guy here—how do I prep for pegging?

OK, so my best friend wants to peg me. Now, at first, it was all a joke, but now I’m actually down for her being my dom. I just want to know how to get ready for it mentally and physically.

Thanks,
Nervous Straight Guy

Hey NSG,

Many of your fellow straight dudes will never experience the fun you’re about to have. I’ve been pegged (by men and women) and assure you, it’s worth the work.

I don’t know if one can fully mentally prepare for receptive anal play, especially if it’s your first time. You will feel nervous, vulnerable, and awkward. Receptive ass play, bottoming — whatever you want to call it — is hard. The right playmate makes all the difference: If you trust her and can be vulnerable with her; if you believe she’ll slow down when you ask her to slow down and stop if you say stop, you’re gold. You got it.

You will need to tell her if something hurts or feels great. Go slow! She must be attentive to your body and breathing, be patient with you, and let you adjust to the feeling; she will not be able to fully take control and dominate your sexy butt the first time you try this.

As for physical preparation: Read my post in The Advocate about happy, healthy bottoming and its follow-up post in Out. Together, these amount to a good bottoming guide — for all bottoms, including straight pegging subs.

Unless you’re vegan or vegetarian and have those miracle poops that leave your butt spotless after a bowel movement, you might want to try some gentle douching, which is explained in the posts mentioned above. Douching is not required for enjoyable butt play, but it often makes bottoms feel more comfortable.

When I top, I don’t care about a hole that isn’t perfectly douched — most tops don’t. Exploring my top side has made me realize bottoms are the only ones who care so much about being super clean — it’s for their own comfort. That comfort is important, but to ease your mind a bit: Your friend knows she’s pegging a straight boy’s butthole and is not expecting the pristine, irrigated rectum of a pro fisting bottom. But a little poop might make you feel uncomfortable during an awkward first-time experience, so to make it easier, I recommend some light, gentle douching beforehand with a small, handheld bulb. (Read those bottoming posts for more details.)

Bottoming is a mental journey, not a physical one. I can’t bottom well until I surrender, relax my body, and slow my breathing. To help me do this, I mentally picture my butthole opening and draw the focus of my body to it. If it were a meditation exercise (secret: it is), when I’m on all fours, I imagine a sense of warmth and gentle focus flowing from the tips of my body — my head, hands, feet — to my hole and picture it getting bigger. That may sound silly, but it gives me something to focus on when my mind would otherwise spin; it takes me out of my head into my sensations.

Since, like you, I’m also a sub, that “focus” I’m talking about is not active. I’m not moving my hips, riding it (unless told to), pushing out (clenching), or pushing back. I’m focusing on letting it be soft, open, and stretched. I mentally decide: Okay, I’m going to experience whatever they do to this part of my body, and my only job is to feel it.

If something feels good, make sounds. Be loud. Tops need reinforcement that they are pleasing you, and the noises you make — pleasure moans or those “pressure grunts” (when something doesn’t hurt but doesn’t feel great) — tell tops which movements feel better. Remember: she wants to make you feel good. Let your sounds and body guide her.

Anal play — whether it involves pegging, a penis, or using toys and prostate stimulators — is something no one does well on their first try. Keep trying. Don’t quit after the first time.

I don’t mean to boast, but I’m a very skilled bottom. I earned my butt from years of lackluster sex, communication errors, impatient tops, and getting poop on someone’s sheets. The mishaps and failures are part of the process. It’s a journey of a lifetime.

Why do it? Because there is no orgasm like an anal orgasm from getting pegged with a huge strap-on dildo. Welcome to Valhalla.

Hey there! I’m Alexander Cheves. I’m a sex writer and former sex worker—I worked in the business for over 12 years. You can read my sex-and-culture column Last Call in Out and my book My Love Is a Beast: Confessions, from Unbound Edition Press. But be warned: Kirkus Reviews says the book is "not for squeamish readers.”

In the past, I directed (ahem) adult videos and sold adult products. I have spoken about subjects like cruising, sexual health, and HIV at the International AIDS Conference, SXSW, the Icahn School of Medicine at Mount Sinai, and elsewhere, and appeared on dozens of podcasts.

Here, I’m offering sex and relationship advice to Out’s readers. Send your question to askbeastly@gmail.com — it may get answered in a future post.