A little after 8 p.m. on a Monday night in June, I find myself running down a quiet street in Prospect–Lefferts Gardens looking for the dungeon where Mistress Red says men turn into sluts. The heat dome has briefly let up, and outside a neighboring townhouse, three men in cotton shirts drink flat beers and watch me fuss with Google Maps. “Down there,” one says, pointing to a set of ivy-lined concrete steps. I follow an alien-shaped fuschia sign downstairs and wait on a wooden bench alongside two eager subs and somebody’s pet’s Chewy box. Pegfest is about to begin.
Founded in 2016 by sex-workers’ rights activist and dominatrix Charlotte Taillor, the Taillor Group is a Brooklyn-based kink collective that teaches BDSM practices to the kink curious. After short-lived stints in a number of other neighborhoods, the collective moved to a basement apartment last September and offers workshops exploring every niche fetish, from good-old foot worship to bondage and roleplay.
But one of the collective’s most popular offerings is the pegging workshops, one-hour sessions in which experienced dommes teach and facilitate the penetration of newbie submissives. The workshop is so in demand that it runs three times a month, and couples and single men frequently request private classes. Pegfest is usually attended by women looking to hone their skills with a strap-on, straight men looking to dip their toes in, and repeat customers with fully realized kinks. Some subs enjoy the exhibitionism of group classes; others wear masks to obscure their identity. For many attendees, pegging is a novel way to subvert gendered dynamics in the bedroom. Whether you’re into BDSM or just want to explore dildos, pegfest is a safe space to learn how to do it comfortably.
“Pegging is a dick’s day off,” says Taillor, dressed in a “Ceasefire” T-shirt and denim shorts, to a few subs as they take their seats on the dungeon’s black velvet couch. The dimly lit living room spills over into a kitchen where a few other subs stand or sit on stools around an island. Four subs would like to be used as bottoms, the other two are here to watch and learn. I eye the cart of colorful curved dildos next to Taillor. “You can relax and be a hole,” she tells us.
This time, no other dommes have signed up to learn, and Taillor and two other collective-affiliated dommes are here to help Mistress Red, a leather-clad dominatrix with waist-length red hair who’s heading up the workshop. Mistress Red has taught here for the past two years, and while pegging isn’t her favorite workshop to lead — it’s not as kinky or creative as the straight men doing it may like to think, she tells me — she enjoys helping them dispel their shame about enjoying penetration. She’s tired of taboos suggesting “that you’re gay or weak or not a man if you want to get fucked in your ass. It’s like, no, it’s just a normal thing to want to feel,” she says. “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.”
Mistress Red sits opposite the sofa on an ornate wooden throne backed by a red curtain, a few paces away from a fridge covered in tiny yellow magnets, each plastered with the words “hot girl shit.” Taillor grabs a grape Poppi from the fridge while the crowd of mostly cis-het male newbies go around the room to share what brought them here. Agewise, the subs range from their 20s to their 60s. There’s a college student who “loves to be filled up”; a regular submissive who loves the collective so much he cleans the dungeon and has a fresh tattoo of a dominatrix on his back; two divorced men who arrive wearing butt plugs and say they discovered pegging after leaving their vanilla relationships behind; a 29-year-old finance guy curious to see traditional male-female roles reversed; and a married-with-adult-kids 60-something kinkster from the Midwest who had a painful experience with pegging and wants to correct that. “A man is never more submissive than when getting pegged,” he tells me. “It’s pure giving up of control and power. Plus it just looks so sexy, a cock on a woman,” he says, adding that he would kneel for me anytime.
After a brief on anal hygiene and how to locate your prostate, Mistress Red starts looking for a wicker basket. “Where’s the picnic basket of dildos?” she asks Taillor, but it’s missing today so she straps on a modest member, sliding a condom over it and slipping her fingers into a pair of black gloves. She’ll peg the regular first. Is he fine with slap marks on his ass? Yes, Mistress. Any injuries or conditions to take note of? Any anal fissures? IBS? No, Mistress. Triggers or traumas? No slurs, Mistress, though bitch, slut, and dumb anal slut are all fine. He strips down under faint green neon lights and apologizes as he tosses his underwear on my sandal; it’s a tight space. Then he’s down on all fours, the dominatrix tattoo raw and pink around the edges. “I won’t spank or scratch that,” Mistress Red assures him. She inserts one gloved finger inside his anus, then another. It’s awkward to penetrate in silence, so a domme turns on instrumental dance music. “See, he’s loose,” Mistress Red tells the room, and switches to using the strap-on. “Now I have my hand on his hip.”
We need different music. “Let’s play Britney Spears. I’m old,” Taillor says. Another domme puts on “Soda Pop,” which I haven’t heard since 1999. Mistress Red pegs the regular to the bubblegum beat. To my left, the finance spectator asks me how my article is coming and invites me to cover an art show.
When Mistress Red decides she’s finished with the regular, he’s on cleanup duty, wiping the mat for the next participant. After cleaning himself up, he sits back down on his stool as the two divorcés head to the bathroom and remove their plugs. We’re strapped for time so they take to the mat together, facing in different directions, and Taillor and Mistress Red repeat the process with both of them, chatting with each other as their fingers assess the laxity of the opposing anuses. The men are disappointed — they’re not ready for dildos — but having an expert assess the muscle is part of the experience. “This is literally why people do anal training,” Mistress Red explains. “It’s a muscle you have to work at. You can’t just be sticking big things in your ass.”
Last up is the college student, who appears to have been scrolling on his cell phone for the majority of the pegging demonstrations. He too isn’t ready for a dildo, but the dommes think up an alternative proposition.
“Want to Eiffel Tower?” Taillor asks him, strapping on an extremely girthy cherry-red member covered in a banana-split-scented condom. Mistress Red’s finger is one side of the tower equation; Taillor’s strap-on is the other. “Have you ever sucked a dildo?” Taillor asks the student. He hasn’t, but this space is so nonjudgmental he’ll try it. The dommes praise his finesse and enthusiasm. “A prodigy,” one says.
After class, we go around the room with our reflections and revelations. Many of the men thank the dommes. The college student says he never realized how much he likes sucking dick. When we catch up over email later, he’s more expansive: Choking on the dildo reminded him of a girlfriend he used to deep-throat with. “I never knew it was choking her like that,” he says. “I’m feeling more vague about the barrier between males and females.” The blurring, he says, helps him allow himself to be more open to love and vulnerability. He’ll definitely be back.
The regular, meanwhile, never left. “He stayed afterwards for hours and cleaned the whole dungeon,” says Mistress Red.
Pegging Class Is in Session
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