My First Time Pegging Taught Me An Unforgettable Lesson

Pegging had been on my mind since Broad City featured it in Season 2 Episode 4 in 2015, but until recently, I still hadn't found the right opening (pun very much intended). As curious as I was, I was nervous to bring it up with any of my sexual partners, so I didn't know if and when it would happen for me. Little did I know that last November, I'd soon hear Katy Perry's voice in my head singing, " I tried pegging and I didn't like it."

I had been sleeping with a guy on-and-off for about six months. I felt like the relationship was going nowhere because we wanted different things (he wanted to date casually, and I wanted to get married and have children, so we compromised and dated casually). I like to try new things in bed with people I'm only casually dating because the stakes feel lower. I know this is confusing — ideally, I'd trust someone more if we were in a relationship, but I can get a little anxious when trying new things sexually with those who know me well. So this time, I thought I'd take advantage of our "situationship" and test the waters of something I'd always wanted to try: pegging. And he was down.

What is pegging? According to a spokeperson for Wild Flower, a sexual wellness boutique, Pegging can be defined as, "one partner (usually female) stimulating another partner (usually male) anally using a strap-on dildo". However, using a strap-on to anally penetrate someone isn't gender-specific — anyone can peg!

Pegging has long held great appeal for me because I associate the act with sexiness, domination, and the excuse to buy something on Amazon. As a cisgender, heterosexual woman, I had only ever been penetrated, never the penetrator. I had never felt like I was in total control of my sexual experiences (not to say that women can't be — just that I personally had not been). In the past, I had always felt like my partners had been able to set the pace during sex, and I wondered if being the one doing the penetrating would make me feel more in control.

The night of, I felt excited but nervous. I was worried I'd somehow "mess it up," or perhaps even uncover some secret part of the male anatomy I never knew anything about (I went to an all-girl's Catholic school — our sex-ed was far from comprehensive).

Before the pegging began, he and I covered all the basics: what type of dildo to use, what positions we should try, how he’d let me know if he were uncomfortable, and what fake name I'd use for him in the article I wrote post-pegging (communication is key, you guys). We also discussed what we thought it would be like: I thought I'd feel like a cowgirl, and he thought I'd feel nothing and he'd feel amazing. I was a little worried he'd be right (it's always bad when the guys I'm seeing are right, in my opinion), but I wouldn't know until we tried. It was go-time.

He lay on his stomach. I mounted him from behind and inserted my finger into his anus. I massaged it and kept asking him if he liked the way it felt or if I should go deeper. I was using my right index finger because it felt like the easiest choice. BTW — no poop! I was overjoyed. I had also purchased anal beads, so we could work our way up to the dildo, but he didn't want to try them because he felt sufficiently ready to be penetrated.

I was ready, too — I’d been strapped in all evening, rearing to get to it. I really enjoyed having it on — it was different, and it felt like I was taking charge of my sexuality for the first time. I had chosen to use a sex toy, which I rarely do, and this particular sex toy was modeled on genitalia I don't have, so I felt like I was really experimenting in a new way. Much like many of the men I've dated, I opted to leave the penis on all day (I've been working from home for years).

I rubbed lube on the dildo (a key part of the process), and got to work. At first, I could only get the tip in. I was terrified — what if this is as far as it went? Would I still be able to write about it? But no, he wanted more. So I forced the dildo all the way inside by slowly pushing it forward, stopping every few seconds to ask if it had gone too far. He kept asking me to push it in further (it did not go gently into that good night — I did have to do some pushing) until I could only see about 20% of the dildo sticking out.

Eventually, he told me he liked the amount that it was in, and asked me to stop pushing it in further. I had achieved penetration! In a matter of minutes I had done what took my high school boyfriend over four hours to figure out.

Here’s the thing no one tells you about pegging: You’re not actually inside them. You’re attached to a dildo, which gets to have all the fun, and, sadly, all the credit. This is where I really expected to feel a rush of power, but once the dildo had been inserted, I couldn’t really move around (I had bought a huge one. It's who I am), so there wasn’t a lot of room to throw my hands in the air. Instead, I just kind of lay there like a beached whale. He was lying on his stomach with his head turned to one side, and I was lying on top of him. I had imagined I'd be up at a 90 -degree angle, but that wouldn't have allowed the dildo to be inside him (this might be true because of the dildo and belt I had used, not because of his anatomy). I had expected to dominate this sexual experience a bit more, so I did once whisper, “you’re a little b*tch” in his ear (which I do not advise people do unprompted), but mostly just for comedic purposes. He didn't find it very funny.

While the dildo was inside, he did moan softly. I wasn't used to it, so I asked him if everything was OK, and he said yes. After about 10 minutes, I asked if he was ready for me to come out. Honestly, I was a little bit bored — I hadn't been moving it around at all. I was lying on top of him, moving my hips up and down slightly so that the dildo moved a little, but not very much. He said yes, so I suppose in that sense, I was in charge of the timing of the sexual experience. I pulled it out slowly, stopping at small increments to make sure it didn't hurt. Again, no poop. A joy.

Afterward, he wanted to penetrate me using my strap-on on. Can you believe that? He already has a penis! I have zero penises! Why would he want the fake one I bought for $16.99 on Amazon? But after properly cleaning it (with whatever supplies are recommended in the instructions — it's different for all sex toys), we tried it anyway. He also felt nothing, because he was also penetrating me with rubber, not a penis with nerve endings. We agreed to get rid of the dildo and just have penetrative sex in the missionary position.

I've since learned that asserting myself during sex and taking control doesn't have to do with who penetrates whom — it's about asking for what you want. Since I hadn't done or requested anything to make the pegging more arousing, I still didn't feel like I was in control. I had chosen to try something that wasn't very stimulating, and that meant I wasn't prioritizing my sexual pleasure during the experience. If I were to try pegging again, I'd try incorporating a vibrator on myself.

While I don't feel as if I gained any insight into the cis-male psyche or what it means to penetrate a partner, I don't regret pegging. Experimenting is fun, and I was happy to try something I'd been wanting to do for a while. At the end of the day, I can count pegging as an educational experience. While my partner said he enjoyed it, we stopped seeing each other shortly thereafter (it was already on the tail-end — if anything, the promise of pegging kept it alive another two weeks).

If you're curious about pegging, I definitely encourage you to try it out for yourself in a safe and consensual way. But in my experience, it doesn't really "up" the romance. Alas, the whole encounter ended the same way as most of my sexual experiences: the next day, I accused him of stealing my charger