I Pegged My Boyfriend

This is What I Learned...

Photo Credit: Jan Kopriva

**This post has been further edited to protect anonymity and privacy.

The Ask

“How would you feel about pegging me?” my boyfriend said.

We were lying on my bed after work together, stretched out fully clothed on my comforter. The dampened London sky and fading summer sun lipped across us, over the top of the white-painted house just beyond my window.

We had been in a monogamous relationship for a couple months at that point. We had the burgeoning love. We had the trust. We had the good communication about sex. I just hadn’t expected our communication to be that good all of a sudden. I didn’t know that meant revealing our deepest, darkest fantasies to each other. And that I, as the other person in this partnership, might find myself obliged to fulfill this simply because the words had been spoken. Yet I could tell by his voice. He had been thinking about this for a while.

At some level, I was honored. My boyfriend felt comfortable enough to share this with me. There was something beautiful in the ask alone. The vulnerability in it. But I still wasn’t sure. How did pegging actually work? What was so appealing about it? And, selfishly, would I get anything out of it?

I wasn’t against the idea, necessarily. My mind quickly turned over my self-proclaimed sexual personality. I had told him I was a switch. Sometimes I liked to be more dominant when we were in bed together. Most of the time I like to be submissive. Supposedly I like novelty. Supposedly I like to try new things. How long had he been planning this for? Was this the goal all along, when he’d shown me the small, dark blue butt plug he kept in his sock drawer that he sometimes used on himself? This was not a completely new topic. But pegging? If that’s what I imagined it was, this would take things to an entirely new level.

I handled the situation delicately. I tried to respond how I would want him to respond if I told him my deepest, darkest fantasy. I cared about him a lot. This clearly mattered to him. What was wrong with me? Why wouldn’t I just give it a go? It wasn’t beneath me, surely (although he would be once we got started).

A couple weeks later, we found ourselves in a sex shop in Soho. We bought a thin, purple dildo and a black strap-on harness for me to wear it with.

The Act Itself

Nobody likes a dirty butt. Pegging is no exception. On that fateful Sunday afternoon, my boyfriend was in his bathroom cleaning his butt. Along with the dildo and the harness, he’d bought an enema, which was surprisingly great value because it doubled as a hot water bottle. (By the way, everything I learned about butt sex, I learned from my friend Reece).

I took off my clothes in his bedroom. I first put on the harness over my underwear. The elastic belt parts felt weird against the fading floral cotton. I was worried. Would that rub sideways and become uncomfortable once I started thrusting? My underwear created a barrier between where my boyfriend and I would be touching. The experience would feel even more depersonalized. I quickly took them off.

The harness I wore.

The harness itself was comfortable. As you can see in the picture, it has a flat, round hole in the front, where you slot the dildo in. It’s kind of like shoving something into a tight, draw-string bag. I tucked the dildo into the front and got the lube ready. Water-based is better for me because I’m not allergic to it, as opposed to the silicone-based stuff which I’ve had reactions to. I spread a towel out on the edge of the bed for him to lay on.

Wearing a medium-sized perfectly sculpted purple dildo strap-on was bizarre. It felt ridiculous, and yet at the same time, I wondered if I was supposed to feel something. Some kind of nerve endings or sensation coming out of the tip bobbing in front of me. But instead, the dildo itself was just a lifeless slab of silicone. I didn’t feel powerful. In fact, I felt exposed. There was so much extra surface area protruding from my genital area now. I felt like I was wearing an elastically adjustable bikini with an arrowed sign sticking out of it which said,

“Sit on me.”

Every way I turned, the perfectly sculpted purple dildo turned with me. In its own way, I knew, this was the closest I was ever going to get to physiologically being a dude with a dick. But without any sensations at all coming from my fake penis, I knew this mimicking of it paled in comparison. I missed my vagina. I missed the predictable, curved slope of its front. I missed its inner walls. I missed the fact that all the parts I was using were tucked neatly inside my lower body, like my own little silent secrets. The perfectly sculpted purple dildo felt obnoxious in comparison.

The sculpted purple dildo we used.

My boyfriend returned from the bathroom.

“Just go really slowly,” he said.

“Okay,” I said.

He lay down on the towel and scooted up to the end of the bed. He seemed to hold his breath as I doused the dildo in lube, and gently felt for his butthole. I started off trying to make sure he was comfortable. I went in a teeny, tiny bit at a time.

My boyfriend closed his eyes. His body tensed. I bent down and felt for the opening. The purple dildo was less than an inch inside. He squinted his eyes open a bit. He peered down. Then he glanced back at me, searchingly. What was I going to do to him? Would it be as good as his best friend, who was a gay and a bottom, had raved about? We were on the edge of where his experience stopped and the terrifying unknown began. I felt the almighty weight of complete control seep through my body. I was towering over him. His penis and balls, the most delicate parts of him, were on full display, inches away from my hands that gripped his inner thighs.

It was then that I remembered that my boyfriend was far less used to having dick-shaped things shoved inside of him than I was. The point of this exercise was not simply to put the purple dildo inside of him. He was perfectly capable of doing that himself. No, this went much further. The point of this was to peg him. To fuck the shit out of him. For him to learn exactly what it was like to have someone carve their entire body weight into him. As his dutiful girlfriend, too curious in my own right, too ready to test my strength, I vowed to myself that I would do just that.

I grabbed him by the outside of both of his legs. I scouted up his entire body weight off the edge of the bed, as I repositioned myself on one knee, one foot pushing up off the floor. I thrust deeper into him, and deeper still. I thrust deeper into him like I wanted it, just like I had wanted more than one male partner in the past to fuck me senseless without coming or a moment’s breath to break. I bent down further on my knees at the edge of his bed.

“Ah,” he gasped. He closed his eyes. His mouth gaped open. He grabbed the edge of the mattress with both hands. With each thrust, he gave a little cry.

“Oh!” He took a deep, quick breath out, like the wind was being knocked out of him. His eyes opened wide between thrusts. I angled my body into his body smoothly, seamlessly, like I was rolling out dough with a rolling pin. Consistent, unidirectional, and back, without pulling out. At the end of each thrust, as I pushed in deeper, I flicked my hips upwards, plowing against his prostate.

“Oof,” he cried even louder. He gasped for breath. His eyes seemed to roll into the back of his head. He looked like he was about to choke and cry at the same time.

I used every fiber of strength in my body, and my twistable, flexible hips. His face was growing pink and heaving. A blotchy, red patch was spreading on the skin beneath his chest hair. His breaths were quickening still. His gasps became small, squeaky moans. I thought he might shed a tear. I thought about the experience I was giving him. The rising tension in his body was far more than he had bargained for.  

I kept hold of one of his legs, as I reached for his penis. I took it gently, firmly, with my left, dominant hand. I massaged it up and down.

“ARGH,” he choked in an instant. His eyes shot to the back of his head. He scrunched up his face, wincing with all his might. His whole body shook. He clenched the bedding tight in his fists. Warm, silvery liquid squirted in spurts onto my hand, onto his front, onto the harness. 5 then 6 then 7 seconds. He struggled for a huge inhale of breath. He brought his hands up to his temples as if he was trying to regain a sense of consciousness. He looked at me, his brow confused. I smiled at him. He smiled back half with relief, and half with the gut-wrenching fear that I was still towering over him, still inside of him, still in control.

I pulled out slowly. My boyfriend winced, breathing deeply, staring up at the ceiling. Once I was out all the way, he lay on his side. His balls peeked out from the back, between his closed legs. I looked down at his quivering body. It convinced me of one thing: men could have pure buttgasms (a term I came up with, which I’m sure already exists, referring to an orgasm from stimulating the prostate without touching the penis). We hadn’t quite gotten that far. But it was completely in the realm of possibility.

I wiped the sweat off of him with the towel. I took off the harness. My boyfriend left for the bathroom to wash the dildo. As he did so, I thought of all the butt-phobic straight men out there. I wondered. Did they know? Did they know that they were the prisoners staring at the shadows on the wall of Plato’s cave? That they had a giant pleasure dome inside their own butthole? And if they did know of its existence, would they ever have the balls to enter it?

Reflections

Pegging my boyfriend brought me to an interesting realization that I hadn’t expected. He had been in a very vulnerable and compromised position for our entire encounter. It was the opposite of what I as a female, and we as a society, have told men that they have to be: tall, muscular, aggressive, and “protective” at all times. It called into question the deepest roots of toxic masculinity. I finally saw how I, as a female, had been inadvertently perpetuating them.

I remembered a time when my boyfriend had stubbed his toe when we were walking down the street.

“Ouch,” he had said, recoiling in pain. At the time, I had been dismissive. I had pretended not to notice. I just kept walking.

I remembered another time when he wanted me to be big spoon after a long, hard day at work. As I cradled him in my arms, I grumbled to myself. Who was I? His Mother? I found the whole experience so unattractive.

I began to realize that before pegging him, I had rejected my boyfriend’s feelings and vulnerabilities so many times. For some reason, I felt uncomfortable when he expressed emotion or that he was hurt. What was so wrong about this? Why did I expect him to protect me all the time? And why had I ignored him the few moments when he didn’t do that?

Pegging my boyfriend changed all that for me. I realized that I now wanted to try to be more loving, supportive, and open to his expressions of emotions and pain. I wanted to be open to his emotional side because I now truly understood that all human beings, men included, need to feel a strong sense of acceptance and belonging in order to be happy. Men have feelings. Men have vulnerabilities. And men deserve to have a space where they can safely express these, especially in their close romantic relationships. Men deserve to be cuddled too. We, as females and as a society, can still love them for it. And we should do more to provide them with that.