PEGSTRESS PEGGIN THA Stallion, 44, flashes their wide smile at me through Zoom, their yellow and pink braids draping over their latex bodysuit as they explain how they became a professional pegging instructor—or, if you want to be fancy, a Pegstress and Peg-preneur—who shares their knowledge of the art of anal pleasure far and wide.
They are devoted to spreading the gospel of pegging, a sex act in which a person (typically a woman) uses a strap-on dildo to penetrate their (typically male) partner’s anus. Pegstress makes a living through OnlyFans and hosting in-person workshops, Zoom training sessions, and pegging pop-ups. For those looking to be pegged, and with $499 to spend, their two-month long “Sphincter School” (link NSFW) teaches students “how to stimulate the nerves of your pelvic floor to achieve that wonderful A or P spot orgasm,” according to their website.
The Pegstress’ mission is to educate the world about pegging, which has become less taboo in recent years, as more men embrace the pleasure of anal and prostate play. “Pegging” was among Pornhub’s highest trending search terms of the year, according to the porn site’s 2022 Year in Review stats.
More From Men’s Health
Men’s Health spoke to Pegstress Peggin Tha Stallion about the pleasures of pegging, why pegging can be a liberating act, and how pegging can improve your relationships.
This interview has been edited and condensed for clarity.
Men’s Health: How did you get into pegging?
Pegstress Peggin Tha Stallion: Well, everything began while I was a professional dominatrix. This one submissive asked me, “Mistress, I want to be pegged.” Now, I had been using dildos and butt plugs and butt toys, and doing butt play and anal play with different slaves already, but I wasn’t familiar with that term, and then I looked it up and I’m like, oh, strap-on play. And when we did it, we decided to do it on webcam because I had already discovered I was an exhibitionist. Watching myself on the monitor pegging him, I just knew, this is it. It triggered several things in my brain and mind and heart. I think that was the moment that it just became polarized in my fetish, career, work, lifestyle.
Can you tell me a little bit about your different pegging services?
I offer one-on-one, couple, virtual, as well as in-person [sessions].
My first in-person experience was with a couple. They were young, like 24 and 25. And she’s like, I want to peg him. I don’t know how. I don’t have the confidence. He’s into this. He watches your porn. And basically, I took her through step by step; I’m explaining everything that I’m doing and why I’m doing it. When I have my gloves on, when I’m spreading his ass, and playing in his ass, I’m like, “Okay, I want you to pay attention, hold the other cheek.” For her to be facing him and holding him and comforting him, it wasn’t even a sexual thing that was happening. It was so nurturing. And I was just like, “Whoa, this was not what I thought it was gonna be.” But in that moment, it was really about educating and nurturing him through his first time while she was there, so she can deliver all the next times.
Based on your experience, why are some men hesitant to peg?
They feel like women are the only ones that should be penetrated. This is what they were taught from their parents and their church and in their culture.
How do you make your clients feel comfortable being pegged?
I help cis males reconcile feelings of guilt and shame associated with the interest and desire to want to explore anal activity. We live in this heteronormative, colonialized, patriarchal society, and these things impact our responses and our reactions, and how we express ourselves. To even have the pegging conversation, I end up having to counter these obstacles beforehand so people can feel comfortable to allow me to engage in dialogue with them about my passion.
It seems like you’re doing a lot of therapy before you get to pegging.
I’m doing a lot more dialogue. I have to introduce [the fact that] this doesn’t undermine your manhood, or masculinity, or change your orientation or gender identity. I have to explain what gender identity is versus sexual orientation. [Sometimes,] I’m talking to someone about pegging, and I meet resistance because they’ve had a traumatic event. It could be something as simple as, “I had a prostate exam when I was 18, and nothing’s ever going my ass again.” So now I’m ending up having to help them lower their guard and feel comfortable and safe, and providing a space for them so they can enjoy it. Then I meet someone who just even had a bad partner, and they’re like, no, never again. It’s like, ‘Whoa calm down.’ There’s a whole lot of things that feel good down there. Your whole pelvic floor is lined with nerves that can make you feel good.
What kind of feedback do you get from your clients?
I am meeting people [who are like], “Oh my god, you helped save my marriage!” Or, “Now, my wife loves pegging me. We peg every Friday night.” I love hearing shit like that.
What is the gender breakdown of people who take your pegging classes?
I’m not just speaking to hetero cis males or hetero cis females, and I’m not just speaking to queer people; I’m just speaking to individuals. That’s probably the first thing that I break down. Let’s take sexuality out of this, and take gender out of it. [Let’s say] pegger, peggee. It simplifies things and allows people to approach me from those two aspects, versus, “I’m male. I’m not gay, but I like this.”
Do you have any clients who identify as gay?
Yes. So, I identify as two-spirit. There is a duality in my sexuality. I have some part Native, and what we believe is that there are certain individuals in our culture that possess the duality of both male and female spirit. I think, because I possess both, I attract all. When I take away the gender and then I am both energies, and it’s like, well, I could be Daddy, I can be mistress. I was born with a vagina, but I’ve always felt I should have a dick, and I wear a dick when I can.
I wish I had a penis. I’ve been obsessed with penises since I was a little kid.
Me too. I was six years old, and I’m teaching myself how to pee standing up. Now as a 44-year-old woman, I [realize] there was always a desire, a feeling of an absence of something that I should have had down there.
Why do you think men could benefit from at least trying pegging?
This is the only opportunity where you’re actually able to receive, and you’re actually able to allow yourself to experience what your partner experiences. I think that is so healthy, because it will make you more appreciative of your partner.
How has your view on pegging changed since becoming a professional?
Now it’s about expression, and causing no to as little trauma as possible. When I started pegging at first, I was out there destroying buttholes. I was no mercy. I was like, “Oh, I got a dick, and you’re all gonna feel it.” Because when you get that dick, it’s so empowering, and you want to just get the biggest one. You want to get a hammer. But the reality is, that is not what the average [person] can take. You got to start small, and you have to work up to it. I’ve had a lot of experience with damaging booties. But I know for a fact that because of that experience, I now know how to pleasure booties and not cause damage. So I’m hoping to pay it forward.
What did you learn about sex from pegging?
I only thought that my power was in the reception of dick and how I handled that reception of dick. Everything that I created about my sexual identity was around that, like being able to prepare to take that dick and suck that dick. But when you become a pegger and you get on the other side of it, you understand sex from not having to present in a way that is pleasing for the penis, because you’re the penis.
Is there anything we haven’t gone over that you think it’s important for me to know?
Just recently in New Jersey, I had this Black guy come up to me, and he was like, “What you do is white people shit.” I want to say there’s no such thing as “white people shit” when it comes to sex. When it comes to sexual freedom, there’s no such thing; that is your oppressors’ voice coming through. I have to let my people know this is for us. It is okay to enjoy and express yourself any way you want.
Contributor
Hallie Lieberman is a historian and journalist. She’s the author of Buzz: A Stimulating History of the Sex Toy, and is currently working on a book on the history of gigolos. Her writing has appeared in BuzzFeed News, The New York Times, Washington Post, Vice, and other publications.
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