First Time Sex
January 17, 2022

In 2021, I Lost My Virginity For The Second Time

Pegging wasn’t a kink thing for me. It was gender-affirming, though I don’t identify as trans.
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January 17, 2022
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In 2021, I lost my virginity for the second time. After years of identifying and passing as a cishet woman dating cishet men, I had a queer sexual awakening when I finally used a strap-on with a man I was dating. Some might call this pegging, but for me, it just felt natural, like I was having the sex I’d always thought about. It helped affirm my gender in a way I hadn’t previously allowed for.

For as far back as I can remember, I fantasized about having a cock. However, I couldn't imagine a scenario where this could play out, so I came to terms with it staying exactly that: A fantasy. 

Going back to my earliest sexual memories, they almost entirely involved picturing myself as a man with other men. I remember stuffing my underwear with socks early in elementary school, and when I started masturbating I imagined myself having a penis. When I discovered porn, I almost exclusively watched videos of men with men. I didn’t exactly experience full-on gender-dysphoria as I felt mostly comfortable living as a woman in my day-to-day life. The fantasies of having a penis were, instead, confined to my sexual life. For that reason, the label trans never quite fit, but I didn’t have a name for my experience, making it all the more confusing. 

Even once I became sexually active, I remember thinking that the cishet men I was dating didn't need to know that, sometimes, I pictured myself as a man while we hooked up. When I was 19, I convinced my mom and doctors that I needed a breast reduction. What I really wanted was top surgery, but without the words for it, all I knew to ask for was smaller boobs. “I want them as small as possible,” I had said to my mom. For years after the surgery, I continued to tell myself and others that I had the reduction to alleviate back pain. I was much happier after the surgery. The large F-size breasts were now a small C and much easier to hide. I started feeling better about how I looked and, once again, pushed down all the other thoughts, keeping them to myself.

But then, two things happened that started to chip away at my decision to stop hiding my fantasy of having a penis during sex. 

  • I bought a dick. 
  • I had incredible sex with someone where we rarely had PIV sex.

The first dick I bought was a small cheap packer. I wore it around a few times, but I wasn’t really sure what I wanted from it, and eventually, I threw it out. A few years later, a friend sent me a comic about something called a Feeldoe. It was a strapless strap-on with an insertable bulb that both kept it attached to me without a harness, but also let me directly feel any movement on the shaft. While I had always thought of strap-ons for sex, this comic illustrated it as being a great tool for masturbating, since you could jack off the cock and actually feel the movement transferring to your body. Masturbating with it was great — it felt like part of my body, and was very affirming to have what I saw and felt match up with what was inside my head. Purchasing the Feeldoe, I assumed it would just be for me, and that I’d never use it with a partner. But owning the Feeldoe meant I could at least have the option for partnered play. 

The next thing that happened was very subtle and small, but was probably the biggest catalyst for my sexual awakening. I dated a guy for a few months where sex for us mostly looked like me giving him oral, and him fingering me while I masturbated. I don’t think there was ever any discussion about what we each were into that got us to that point, but it was the first time I realized sex didn’t need to involve me being penetrated by a penis. When that ended, I decided I wouldn’t date again until I could better articulate what I wanted in bed and confidently communicate that to a partner.

During this pause from dating, I started to tell friends about the great sex I had just been having. I also started bashfully telling friends that, sometimes, I fantasize about having a penis. The more I talked about it and the more positive and encouraging reactions I got, the more normal it began to feel. Eventually, I decided to get back on dating sites (Tinder, Hinge, Feeld) — this time, also including “kink-friendly” in my profile.

At this point, I still wasn’t sure if I wanted to use my cock with someone else. I didn’t know if it would feel like what I had always been missing, or if it would be overwhelming and I wouldn't know what to do with it. But by using kink as a starting point, I found I was able to have open dialogues about exploration of new things. Kink and BDSM also allowed for lots of check-ins and communication about everyone's wants, needs, and feelings before, during, and after sex. 

This is what led me to “pegging.” I began talking to a few men that were looking for a femdom and had either been pegged before or were interested in trying it for the first time. Despite having considered myself to be submissive, I found myself to be surprisingly excited by this, and realized this would be the perfect opportunity to incorporate my cock. I ended up connecting with a guy who identified as straight but who also thought dicks were hot, and loved his butt being played with. A few weeks later, we had a date set, and I was frantically looking for a harness to make sure my strap-on would stay in during penetration. (While you don’t need a harness for solo play with the Feeldoe, I had heard they made partnered sex way easier.) That day, I was both nervous and excited. I still couldn't believe it was actually going to happen. But as soon as we met up and started to relax and talk more, I felt more and more comfortable. When we started to have sex using my strap-on, it felt natural and easy. We went slow, and kept checking in with each other, but I was surprised at how, despite having years of sex where I was the one being penetrated, I pretty quickly and seamlessly fell into the role of topping. I was also surprised at how much pleasure I got from it. Just seeing my cock, coming off from my body and going into someone else's made my mind believe I could feel everything that was happening, too. After the first time, I felt so giddy, like I wanted to tell everyone about this new experience. It felt similar to how I’d felt years earlier, when I lost my virginity for the first time. It felt like the person I was before was different from the person I was after.

This began my “Hot Girl Summer” full of mind blowing sex using my cock. Though we had found each other through kink, it didn’t always feel kinky, and more than anything, it just felt immensely validating for my gender and sexuality. This guy saw my cock as a real part of me and not just a strap-on, and we rarely used the term pegging. It just became our version of “normal sex.” There were other toys I bought that also added more fun to the mix. I purchased a dildo with a small hole running through it that, when sucked, mimicked the feeling of a blowjob by transmitting suction to my clit. I also got another packer to have a soft dick to start with, instead of going right to the fully hard Feeldoe. 

All of this allowed me to reprogram my version of what sex was and needed to be, both for myself and with partners. My partner and I left that relationship identifying as queer, feeling like we had awoken a new part of each other. After that, I could more easily tell others what I was into and what sex with me would entail. 

Though the term pegging hasn’t always felt right for me, it has created space for me, a mostly cishet woman, to have sex with a mostly cishet man while wearing a strap-on dildo we agree to believe is a real penis. I’m not sure if that’s what pegging looks like for others. I used to assume it was more about some kind of power exchange with specifically a woman penetrating a man, or it could be a kink thing, with the man submitting. I just found it to be a lovely way to validate and affirm a part of me I had been wondering about my whole life.

Reviewed for Medical Accuracy

Ally is a woodworker and carpenter living in Vermont. She spends her time carving wood, building houses, camping, hiking, and talking about sex!

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