How to Orgasm via Prostate Stimulation and Pegging

The first time Cooper Beckett was pegged he had a prostate orgasm that lasted 55 minutes.

Beckett, a writer and host of the podcast "Life on the Swingset," enjoyed the experience while on holiday in Mexico. Long after sex had finished, he said, his orgasms kept washing over him in waves: "We'd actually gone to dinner afterward and it was still happening. I couldn't even hold the tongs at the buffet because my hands were shaking. I had to ask for help."

This type of "p-orgasm" can happen when the prostate gland, which is located in front of the rectum and below the bladder in cisgender men, is stimulated. One way to do this is through pegging, which is when a person uses a dildo to penetrate the anus of their partner.

While anyone can give and receive this style of sexual penetration, pegging is most often described as an act during which a woman enters her male partner while wearing a strap-on dildo. Despite some men reporting this act as extremely pleasurable, there's still a significant stigma and fear around being pegged that prevents many men from even considering it.

What it feels to have a prostate orgasm

Chris, who co-hosts the podcast "Swinging Along" with his wife Karen, decided to try being pegged because he'd heard that it was "one of the best orgasms a guy can have." Now, pegging has become a regular part of his sex life, and he personally confirms the hype.

"Your whole body feels it," he said, adding that it's more of an "inner-body orgasm."

But even though the couple is part of the sex-positive swingers community, they've encountered plenty of resistance and even noted some disgust from men when pegging is suggested.

"I can't tell you how many times I've heard 'Ew,'" Karen said. "Or they say, 'I'm not gay,' and I have to bite my tongue."

Homophobia remains one of the reasons men are quick to dismiss being pegged. This is coupled with the misogynistic perspective that men should most often operate in the dominant role, while the person being penetrated is in the submissive, "lesser" role.

"These are old tropes that have been pushed very strongly in terms of gender roles," said Dominus Eros, a sex educator. But "all of it is BS," he added, because he believes at the end of the day what truly matters is whether or not you're getting pleasure from the experience. Eros teaches an online Introduction to Pegging class and said he addresses some of the fear around the practice by demonstrating it in a safe, inclusive and positive way.

The act of pegging challenges gender roles

For Beckett, being pegged actually increases his empathy and understanding for others.

"The idea of the penis, in general, is about penetration and that of entering another space," he said. "A lot of men really don't like being in that vulnerable emotional spot, especially during sex, where maybe they feel like they need to be the aggressor."

The three men advise starting slowly with a small apparatus, and increasing its size and the intensity of the action once you feel comfortable. It's best to invest in different sizes or to start off with a toy that's specifically geared toward prostate play.

"Choose your apparatus that you may want to go inside of you; have a relationship with it," Eros said.

"And if you have any fears, if you're scared, talk about it, open up to it, and see how (the toy) can be moved and how you can find the pleasure," Eros said. "If you are not on the journey of finding pleasure, then it's a lot harder to get over that hump of fear."