What Pegging My Male Partners Teaches Me About Sex

It wasn’t until I was 21 and working as a sales associate at a sex toy store that I found out about pegging. I had always known that anal play wasn’t gender-specific, but once I learned that women fucking men with a strap-on was an actual thing, and that people enjoyed it, I became totally obsessed. I wanted to try it for myself.

If I was going to broach the subject with someone, I figured I needed some idea of what I was doing. I had a decent amount of experience on the receiving end of anal, so I knew how painful it could be if done wrong. I read several different books which gave me step-by-step instructions on stimulating the prostate. I listened to interviews with a woman named Strap-On Jo, who claimed to be an ass play and pegging specialist. All the experts said that the practice actually wasn’t all that uncommon, and that even more men would probably be into it if not for the social stigma.

A close friend of mine and I had been having playful no-strings-attached sex for a few weeks, and I decided that I trusted him enough to share my newfound obsession. “I … want to put my fingers in your butt … sometime,” I blurted out. He let out a laugh, amused by my fervor, and shared that he already played with his own butt a little, but had never had another person finger him before. The next time he came over, we dedicated a part of our night to his butt.

I put a black nitrile glove on one hand, and accidentally squeezed way too much lube out onto my fingers before inserting them into his butt. The prostate is on the belly side of the anal canal, and usually two to three inches inside. His was at least three inches in, so I had to root around with my finger all the way inside before I was able to find it. I moved slowly the entire time, and took great care to stroke — not poke — his prostate, which was about the size and texture of a walnut, but soft like a ripe peach.

I moved slowly the entire time, and took great care to stroke — not poke — his prostate, which was about the size and texture of a walnut, but soft like a ripe peach.

I tried to recall the specific moves and advice I’d studied up on, desperate to make him orgasm. I rubbed it side to side like a windshield wiper, moved my finger in the notorious "come hither" motion that is so divine on the G-spot, and pressed upwards toward his belly in a firm rocking motion. Moving my arm back and forth with such intensity and precision against the pressure of his butt muscles made me feel like I was playing some strange musical instrument for the very first time. It was nerve-racking. Was this even going anywhere? Was he feigning enjoyment or really into this? He was looking down at me the entire time, very concentrated on what was happening. He nodded me on in encouragement, but also stopped me occasionally when he needed a break.

It ended up being even more enjoyable than either of us expected. He actually came without me even touching anything except his butt. Afterwards, I sat there with a giant grin, massaging my very tired arm.

Rabbit Habit Vibrator, $43, Amazon

Once I had some prostate experience, I confidently asked almost every guy I hooked up with if I could finger his butt. This was met with mixed reactions, but I used any rejections as an opportunity to talk about why it was worth considering in the future. Over the next year, I fingered at least six or seven more butts – I was incredibly eager to experience the wide world of prostates, and to pleasure the masses. When people were into it, I didn't really need to encourage them into letting me stimulate them this way. It seemed as though they had been thinking about it in the back of their heads for a while, just waiting for someone to come along who was also into it.

A year later, I moved to Detroit and met a guy who was just as enthusiastic about butt play as I was, if not more. He was actually more sexually open-minded than anyone I’d ever been with, and was down to try out anything that I was interested in. It wasn’t long before we began dating, and we were already discussing how we could make my pegging dream a reality.

It felt like all my previous experience had led to this moment — a day when I would don a cock of my very own. So I set out to find the perfect harness and dildo. I wanted a toy that wasn’t much bigger than the two fingers I’d been using on my boyfriend, and I had a good idea of what I was looking for from my days working at the sex shop.

Since I was in a new city, I stopped by a shop I had never been to before. When I found my way to the dildo section, I inquired about something on the slimmer side. “What, you don’t think you can even take THIS?” the girl working replied, pointing at what she must have considered to be a “small” dildo. Even though I don’t embarrass easily, I was flushed and quite uncomfortable because of her judgmental remark. “Actually, it’s not for me. I’m about to fuck my boyfriend for the first time … so lay off!” I scurried out the door, and purchased my harness and dildo online instead.

It was one of the most exciting packages I’d ever received in my life. I went with a dildo called the Mistress and a comfy cloth harness called the Joque. I tried them on immediately, posing myself in my bedroom mirror. I lay down on my side, holding the dildo in one hand like I was jerking it off and sent a selfie to my boyfriend. I could hardly contain my excitement.

Mistress Dildo, $42, Amazon ; Joque Adjustable Harness, $115, Amazon

When my boyfriend came over that night, we spent a few moments just cuddling while I wore my strap-on. Now we both had penises! We played around a bit; I smacked his dick with mine and he gave me a brief blowjob. It was truly bizarre, but also a sight unlike anything I’ve ever seen before. Then, as he lay on his back, I lubed up the end of the dildo. Right before I took the plunge, we exchanged loving smiles and he said he was ready.

I was quite clumsy at first. The dildo slipped, bent around, and missed his butthole a few times before I could get it into him. I had to hold the base with one hand and guide the tip in with the other in order for it to work, but once I was in, I was in. I only let a couple inches go in at first, but as he relaxed, I was able to go farther. I frantically reapplied lube, and kept asking if he was OK, but he said he loved it. The dildo popped out a couple of times, but I eventually found my rhythm when I stopped overthinking it.

It was like I was in some alternate reality. This guy who had been fucking me was now on his back with his legs up around his ears. I was sitting back on my heels with my thighs outside his hips, rocking my hips back and forth in little humping movements, which made my knees and hip flexors ache. I immediately realized that pegging was totally exhausting, and I felt like I needed to take a break to stand up and stretch.

As he lay on his back, I lubed up the end of the dildo. Right before I took the plunge, we exchanged loving smiles and he said he was ready.

Next, he was on all fours and I was behind him doggy-style. I flipped the dildo upside down so that the curve would still be targeting his prostate, but I was totally caught off-guard by how insanely awesome it looked to see him in this new position. His butt was right there, ready for action, and his penis was dangling just below it. What a sight. I paused, inspired and thankful for the whole experience. This position was much more comfortable for me, but he preferred being on his back. Once we switched back, he suddenly came without any warning.

My mind was blown. I hadn’t come, but watching him come felt just as amazing for me. I had put on a dick, fucked a guy’s butt for the first time, and now he was lying before me in a puddle of melted bliss. He looked so angelic. I ran to the bathroom, carefully took off the harness in order to avoid getting butt juice all over the place, and left it in my bathtub to clean later. I hopped back in bed with him, and we cuddled and recounted the entire experience from start to finish.

I didn’t peg him every time we had sex from then on; we both saw it as a special treat. Sometimes, I pegged him a few days in a row, but we would also go weeks without doing it. I absolutely loved it, though for me, it was definitely more satisfying psychologically and emotionally than it was physically. When I pegged him, I generally wasn't seeking my own orgasm, but that was my choice. Since he would be very tired after having his prostate stimulated, I would usually just masturbate afterwards. I usually liked to keep the focus all on him. Now that we both had the ability to penetrate or be penetrated, it made our sex life feel limitless. It also dramatically changed the way that I saw sex without the strap-on.

Mistress Dildo, $42, Amazon ; Joque Adjustable Harness, $115, Amazon

Having never been the penetrator before, I realized how it’s such a huge misconception that the person with the “cock” is the only one who does the “fucking.” My boyfriend directed the action for a good portion of the time — he had to in order for me to hit all the right spots and angles. It made me realize how silly it is that we describe the receiver as the person who gets “fucked,” when in reality both people are giving and receiving pleasure simultaneously.

It also made me really think about my gender identity. Even though pegging isn’t inherently a role reversal, it reminded me of how fluid gender is. Even though I really love my pussy and am über feminine by a lot of society’s standards, there is also a very “masculine” person in me that I like to express sexually as well. Seeing my partner, who was a big buff "manly man," in such a receptive and somewhat vulnerable sexual state was such a beautiful and liberating experience for both of us.

Seeing my partner, who was a big buff "manly man," in such a receptive and somewhat vulnerable sexual state was such a beautiful and liberating experience for both of us.

Besides my then-boyfriend, I’ve pegged one other person, and it was just as pleasurable and intimate there. While I really enjoy pegging, I know it’s not something that I require sexually. Experiencing something so new and different was truly enlightening, but if I had a partner who didn’t want to do it, that definitely wouldn’t be a dealbreaker. Pegging is exciting and goes against everything we’ve been taught about sex, yet for me, it felt more innocent and intimate than a lot of my other experiences. If you’re even the slightest bit curious, it’s really worth exploring.