Reporter reveals seedy underground world of NYC's 'pegging' craze

You might expect a busy New Yorker would turn to cocktails or workout classes to relieve their stress. 

But there's a new, unconventional hobby that some young city dwellers are turning to: lessons in a sex act known as pegging.

An increasingly popular collective in Brooklyn is offering workshops for people who are intrigued by the experience, but don't know where to start. 

For those unfamiliar with the term, pegging involves a man being penetrated by a woman using a prosthetic penis for sexual pleasure.

And one writer has immersed herself in the trend, attending a lesson aptly named 'pegfest' and quizzing the heterosexual men who attended on their passion for the sex act.  

Charlotte Taillor, the founder of the Taillor Group, a Brooklyn-based 'kink-collective' which hosts classes for people curious about sexual experiences, like pegging

Charlotte Taillor, the founder of the Taillor Group, a Brooklyn-based 'kink-collective' which hosts classes for people curious about sexual experiences, like pegging 

Learning: Charlotte uses her dungeon to hold 'classes' that are aimed toward teaching women more about their sexuality

Learning: Charlotte uses her dungeon to hold 'classes' that are aimed toward teaching women more about their sexuality 

Bindu Banasinath, a writer for The Cut who covers relationships, attended an hour-long class run by collective The Taillor Group, where six men aged between 20 and 60 practiced pegging.

Their lifestyles ranged widely — some were finance professionals, others were students and others were doting fathers. 

Attendees also had a range of experiences, with some seasoned and others first-timers. 

The classes are led by dominatrixes, who also teach other workshops about bondage, foot fetishes and role play. 

For one hour only, these women show their pupils, or 'submissives', the ins and outs of sex acts involving the rear end. 

Ms Banasinath watched as Mistress Red, the dominatrix leading the night, explained how to safely clean the anus and locate the prostate.

Next, Mistress Red entered into the tutorial phase of the night, in which participants learned whether or not their sphincters were relaxed enough to accommodate a sex toy, or whether they were still in the training phase. 

Then one by one, the dominatrixes assessed their pupils' muscles using their fingers — protected by latex gloves and condoms. 

Though Mistress Red said pegging nights weren't her favorite to instruct, she had some positive things to say. 

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

Ms Taillor, the founder of the group, said that the practice allows men to 'relax and be a hole.'

It's difficult to know how common pegging is, since what happens in the bedroom often stays in the bedroom. 

But searches for the term have increased steadily over the past 20 years, peaking in July of 2022, according to Google data

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

Penetrating the anus can therefore result in an orgasm that's similar, physiologically, to the female orgasm.

Though many people associate prostate-play with homosexual relationships, pegging is usually a heterosexual act.

The dungeon has been open for visitors in the Prospect-Lefferts Gardens neighborhood of Brooklyn since September 2023. 

Ms Taillor's group was previously pushed out of a different Brooklyn neighborhood in 2019, after neighbors complained the collective brought, 'weirdos and perverts' to the area.