‘You have totally changed as a person’

The straight men of NYC are really opening up this summer.

Big Apple bros are leaning into their submissive side — and expanding their sexual repertoires — by attending once-taboo pegging classes.

Pegging — an anal sex act in which a woman penetrates a man’s anus with a strap-on dildo — has been growing in popularity in recent years.

The Taillor Group, a Brooklyn-based kink collective that teaches BDSM practices to the kink curious, revealed that informative pegging gatherings called Pegfest have become some of the collective’s most popular being attended by a breadth of interested participants — mostly cisgender men in their 20s to 60s from a range of backgrounds.

Pegfest has become so in demand that it now runs three times a month. Those who don’t snag a space in time often request private lessons.

Last year, Clips4Sale, the largest online platform for kink and fetish content, named pegging 2023’s “Fetish of the Year,” while the more vanilla Pornhub revealed that “pegging” and “strap-on” were among the highest trending search terms of the year, per the platform’s 2022 Year in Review report. 

And as the sex act has become more mainstream — it was even mentioned in the “Deadpool & Wolverine” Disney movie trailer earlier this year — men in NYC want to make sure they get it right and tight.

The classes hosted by the Taillor Group are led by dominatrixes who go through the group, focusing one-on-one with each attendee to guide them through how to penetrate or receive penetration safely.

Pegging stimulates the prostate, the sensitive bean-sized gland that sits beneath the bladder in the male body, pressing up against the rectum.

If done correctly, it can result in an orgasm that’s similar, physiologically, to the female orgasm. If not performed properly, the act can lead to some undesirable and painful effects.

Many people wrongly associate prostate-play with homosexual interests, but the act is usually conducted by heterosexual couples.

Mistress Red, who leads pegging workshops with the Taillor Group, told The Cut that she’s tired of misconceptions “that you’re gay or weak or not a man if you want to get f-cked in your a–. It’s like, no, it’s just a normal thing to want to feel.”

“There’s this sort of very fun gender switch that happens. It’s crazy, the physical and mental transformation putting in a dildo will do. You have totally changed as a person,” she said.

Experts have attributed the rise of pegging to a long list of cultural changes, including shifting gender identities, relationships and sexual preferences.

“It’s helping break down stigma about sexuality, gender, power, mental health, vulnerability, and the list goes on,” Certified Sex Educator Sunny Megatron, Editor in Chief of Zipper Magazine and co-host of the American Sex Podcast, told Cosmopolitan.

“And that’s not even factoring in the earth-shattering orgasms!”

But Mistress Red warned of jumping right in and highly recommends doing your research and practice. “It’s a muscle you have to work at,” the dominatrix cautioned.

“You can’t just be sticking big things in your a–.”