Her Perspective: How We Started Pegging

Well that’s a story that goes back years…

Initially, I wasn’t open to the idea. I grew up in a rural area where anything outside “the norm” is frowned upon. I also didn’t explore too much outside the vanilla forms of sexuality. I watched porn, but didn’t search out anything super kinky. 

When he first brought it up, I said something crass and insensitive. My reaction, while not my proudest moment, was the result of cultural programming around male anal play. Why was my very heterosexual boyfriend asking for something only homosexual men did?

We were in our mid-20s at the time and pegging was still VERY niche. This was well before the famous Broad City episode and cultural visibility was essentially non-existent. Like many women (and men) at the time, I didn’t know anything about the prostate or its role in male penetrative pleasure. I judged the request in a social context rather than a physiological one.

He was pretty embarrassed and didn’t bring it up again for a while.

As our sex life matured, we explored anal play on me and I began to enjoy it. That made me more comfortable with anal play for him. 

I’m a giver, by nature, and loved how hard he came with a buttplug or nJoy wand. The sounds he made when I gave him a combined penis-plus-prostate orgasm were divine. That power was addicting and scratched my praise kink itch in a wonderful way. But I had a few hangups.

In prior blogs, I wrote about my ADHD and sensory sensitivities. When we first started with anal play, I was very sensitive to smells and the slipperiness of lube on my hands. I was not fully honest about that early on and should’ve been. Maybe I didn’t want to hurt his feelings. He could tell that something was off and interpreted my hesitancy as a judgment of something he really enjoyed vs. a sensory reaction to a few very specific - and fixable - things.

I could tell how much he liked anal play with toys, so I decided to fulfill his pegging fantasy. Our first few attempts were not great. We were both pegging virgins (and really new to anal play in general) and hadn’t figured out the necessary prep work. Things got messy. He, understandably, got embarrassed and my sensory ick was engaged. Those early attempts didn’t provide much positive reinforcement, for either of us, and we didn’t try again for a while.

We’re both in individual therapy in addition to marriage therapy (highly recommended). It sounds cliche, but we learned the importance of open and honest communication, even if the topic is awkward or difficult. Pegging, even without the sensory challenges, was very intimidating to me. What if I was bad at it? My fear kept me from embracing it.

I realized I often avoid trying things if I believe I’ll be bad at them. I can’t be bad at something, and feel bad about that, if I never attempt it in the first place. Over time, I learned to redirect negative self-talk. Instead of saying “but what if I’m bad at it,” I ask “what if it will be really great?”

Chastity and femdom really helped build my sexual confidence. I realized I didn’t need to be perfect to scratch my husband’s submissive itch. I really started to enjoy our dynamic. As I got more confident in my mistress role, I began to feel more naturally curious about pegging again.

My husband never pushed me too hard on pegging, but he did continue to voice his desire to explore more. He really wanted to learn how to cum hands free for me and that challenge helped inspire my own enthusiasm (I’m a competitive former athlete).

We actually did our homework this round. We figured out the proper preparation and cleaning protocol to avoid prior mishaps. I was more honest about my sensory needs and we incorporated that into our play. Now, he always provides a hand towel so I can immediately wipe my hands off. Or, he applies all the lube himself as part of his submissive duties. That relatively basic series of optimizations changed the whole experience. No more lube-y hands.

He did homework on his own, too. He used the Mindgasm app and other mindfulness techniques to help him “let go” in the moment and not feel so awkward or embarrassed about enjoying penetration.

Most importantly, we had a series of deep conversations about my acceptance of his sexual identity. I made it really clear that I wanted to explore every facet of our sexualities together and I was genuinely turned on by chastity and our femdom dynamic.

As those conversations (and the intensity of our chastity dynamic) progressed, so did our pegging frequency and satisfaction levels.

Our non-pegging sex life has always been fantastic and natural. I remember the first time pegging felt like THAT. He totally let go and didn’t censor himself, wrapping his legs around my waist and moaning into my ear as I fucked him missionary. We flipped over and he began riding me, his back arched and eyes closed, moaning even louder. I’d never seen him lost in pleasure like that. 

I thrust into him and grabbed his hips, forcing him to pause.

“Stop. Take your hand and feel how wet the harness is. Feel how much I’m enjoying this.”

He put his hand between my legs. I was dripping. 

“Fuck…” 

Pegging taught me a lot about male bodies. I learned I can literally fuck the cum out of my husband. It’s usually not a full-blown penile-type orgasm, but a highly-pleasurable, uncontrollable release of precum caused by pressure on the prostate. If that happens, a true penile orgasm is moments away… if I allow it.

In this case, I allowed it. I started stroking his cock as he pushed himself back onto my strapon. He made noises I never heard before (and now want to hear every day of my life), before coming violently all over me. 

Since then, the pegging awkwardness is mostly gone. Sometimes he requests it, sometimes I do. We’re still experimenting with different dildos, harnesses, and lube. Sometimes we start and one of us says, “Hey, tonight’s not the night.” And that’s OK. We need to be in the right headspace and sometimes we need to start playing before we realize we’re not. It absolutely takes more planning than “normal” penetrative sex. And it’s not something we just do on a whim, especially with two toddlers. But, after years of communication and practice, it’s a really important part of our sex life. 

I’m happy to report that pegging success unlocked a new sense of dominance. I feel more sassy and bossy and increasingly powerful. 

I’m also more imaginative and curious. I started my own Reddit account and followed all my husband’s communities. A few years ago, I would’ve been intimidated by what I saw.

Now, I take notes.