I Got Pegged by My Girlfriend, Then Dumped. And It Left Me Wanting More.

Most men won’t admit to wanting anything near their ass—much less inside it. For that reason, pegging, a sexual practice where one partner penetrates the other anally with a strap-on, is sometimes treated as taboo. The term pegging entered common usage nearly a quarter of a century ago, after the sex columnist Dan Savage held a contest in 2001 to name the act.

For the latest installment in our series on the Secret Lives of Men, we interviewed David*, who had long been intrigued by the idea of getting pegged by a sexual partner. When he finally had the experience he was seeking, the forty-year-old professor found that he was cracked open—not just by the sex, but by heartbreak, submission, and the unnerving thrill of surrender.

*Names and identifying details of the subjects have been changed to protect their anonymity.

I’d been curious about anal play since my early twenties. Alone in my apartment, I ordered a small butt plug online; it was made of hard plastic, bullet-shaped, not particularly forgiving. Trying it wasn’t about wanting men; it was about exploring a part of my own body that most men ignore. With enough lube and patience, I learned to enjoy the pressure against my prostate, lighting up nerves I didn’t know I had, and unlocked a different kind of orgasm. Still, I kept it private.

Years later, in my early thirties, I finally tried pegging with a partner—Julia. It didn’t go well. She had experience with women, and when she saw my rigid toy, she immediately dismissed it: “That’s not what you want.” She suggested something softer, silicone with some give.

The problem wasn’t just the toy, though. We rushed in. One night, a few months into dating, she strapped into a black harness with a dildo and moved in behind me. I hadn’t been warmed up enough. She pushed too quickly. My body locked up. Within minutes I was in pain; ripped, bleeding, humiliated. For days afterward I had her checking the damage I couldn’t see myself. Hemorrhoids, fissures, embarrassment. It was enough to shelve pegging as a fantasy I might never realize.

I’m forty now—six-foot-four, a university professor on the East Coast—and I still think about that first failure. But I also think about what came after with someone else.

A little over two years ago, I met Mara. She was five-foot-three, married and working on her divorce—shy at first, but bolder as we grew closer. We explored everything together: spitting in each other’s mouths, power dynamics, her first squirting orgasm. She learned new things with me; I learned new things with her.

Our connection was almost unsustainable in its intensity. But unlike with Julia, anal play with Mara started small; no harness, no toys at first, just her fingers, trust, and nuance. She discovered how to touch me in ways that made me make sounds I didn’t know I had in me. She made me feel not just aroused, but expansive, like I was discovering new parts of myself through her.

By then I’d already upgraded from that cheap plastic plug to a pair of glass ones: smooth and weighty, one shaped like a teardrop, the other a skinny translucent shaft. But Mara didn’t need them. She was confident with her hands, and she could take me to places the toys never did.

Pegging became the unspoken next step. We both knew it.

When it finally happened, it was during a fragile period. I’d been away on a pair of artist residencies, long stints where we kept in touch only by text or the occasional call. By the time I came home, something in her had shifted. She was seeing someone new. The air between us was different; still charged, but less certain. I felt her slipping away, and my instinct was to hold tighter.

That Sunday afternoon, pegging became the way I tried to pull her back.

The toy was a strapless strap-on, cobalt blue silicone, and curved so that one bulb anchored inside her while the shaft pointed toward me. I was on all fours on her low bed, bracing against the mattress, while she stood at the edge in platform shoes to make up for our height difference. She took her time, working me open with her fingers, spit, and steady patience before easing the first inch in.

For a moment, panic jolted through me. I flashed back to Julia, to tearing, to failure. My body tensed.

But Mara held still, patient, waiting for me to breathe through it. Slowly, I relaxed. Inch by inch, she eased deeper until the blue silicone was buried inside me.

The sensation was overwhelming. When she began thrusting, slow at first, then harder, I felt something shift in me. It wasn’t just anal pleasure. It was submission, the loss of control, the shock of realizing I was being fucked. Not playing, not experimenting, but fucked. My voice dropped into guttural sounds I’d never made. After a while I pulled her back in front of me, and that’s when I came; still charged from the pounding inside me. The orgasm didn’t hit like a peak; it stretched out, long and rolling, pulled from deep in my body, almost more wave than climax. It felt like losing a kind of virginity.

The contrast with my first failed attempt years earlier was stark. With Julia, the sex had been painful, but she stayed afterward; checking the damage, making sure I was okay. With Mara, it was the reverse. The act itself finally felt transformative, but afterward, when I was raw and reaching for her, she was already half-gone. Women know that feeling too well—the first time that leaves you more exposed than held. I don’t pretend the experiences are the same, but pegging gave me a glimpse of that imbalance, of what it means when vulnerability isn’t met with care.

But as I lay there, wide open, Mara picked up her phone. Messages from someone else lit the screen. When I reached for her, I could feel her half-elsewhere already.

In the weeks that followed, our relationship collapsed. I’ve wondered about that timing ever since. Was pegging the desperate attempt I made to keep her close, to prove there was still new ground for us to break together? Or was it her way of saying goodbye, of giving me the intimacy I’d wanted before she moved on?

I don’t think it was either, not entirely. We weren’t sealing the past. We weren’t ending. It felt more like we were checking boxes, proving to ourselves that the relationship still had the capacity to surprise us, even as it unraveled.

What I do know is that the experience left me changed. It was the first time I felt truly submissive; properly fucked. Not just aroused, but overwhelmed and out of control.

With Mara, I learned how intoxicating it is to meet someone who feels like your opposite half, someone who flips your world. But I also learned that not every relationship can survive that fire. Sometimes the people who open you the widest are the same ones who can’t stay.

The irony is that while pegging got tangled up with heartbreak, it didn’t scare me off. If anything, it made me hungrier. Most men never make it here; too spooked by the idea that anything in their ass cancels out their masculinity. But that’s bullshit. Anal play doesn’t take your manhood; it rewires it. Submission isn’t weakness. It’s another kind of strength.

So yes, pegging split me wide open. And the truth is, I want more.