Four lessons for next time from my less-than-ideal strap-on experience

Lustery POV writer Anne Shark shares all the details of her very first strap-on experience and the four lessons she is taking with her for next time

What I Learned From My First Strap-On Dildo Experience

I Tried a Strap-On Dildo, but It Was Better as a Fantasy

The fantasy of having a penis started in college. I was in my early 20s, lying behind my boyfriend in bed, my body molded to his. 

Maybe it was morning — I remember a soft and languid sensation throughout my body. Or maybe it was just us, the comfort and ease I felt being with him. 

I remember a slow, lovely build-up of sexual energy as I held him in my arms for a while, just breathing, before I allowed my hand to slide down his stomach to hold his penis, which was slightly hard and hardened even more in my hand. 

I kept breathing slowly as our bodies began moving together slowly, subtly at first. 

We grew more and more connected. As I kept my hand on his cock, it felt almost as if it were mine. In giving him pleasure, I was giving myself pleasure — I was that connected with him, it was like I was inside of him. 

As I kept my hand on his cock, it felt almost as if it were mine.

Is this what it’s like to have sex with a penis? I wondered.

This is where my fantasy of having a penis and penetrating a lover was born. 

A couple of years ago, my friend, a woman in her late thirties, told me about her first experience 

. She shared that the act of pegging her partner was the first time she’d had an orgasm. 

…the first time EVER that she had an orgasm… 

This conversation did a couple of things for me: 

For one, I just felt a wave of compersion (happiness at her happiness) for my friend, who’d just discovered this exciting doorway into her own pleasure. 

Secondly, it normalized the act of wearing a strap-on dildo for me, making me realize that this was something that I might have the opportunity to try myself. 

Third, it reminded me that there are people who want to be on the receiving end of penetration from a woman. 

When I finally had the opportunity to wear one, however, it wasn’t quite what I’d envisioned. 

I’d been dating Evan for a couple of months when I shared my fantasy of wearing a strap-on over drinks with them one evening. 

“I have been leaning into my bottoming energy,” they said, giving me a seductive look that achieved just that… I was seduced. 

We’d talked about it before. They’d shared that they had previously only felt comfortable topping (giving), and that bottoming (receiving) was challenging for them. It felt so vulnerable, they explained. And as t

 points out, “Vulnerability in general, and sexual vulnerability in particular, is a key element of great sex.” 

I felt honored and close to them by their willingness to lean into vulnerability with me. We decided to try it that very night — I’d wear a strap-on, and they’d be my bottom. 

As Evan and I left the restaurant and walked back to their place, I felt jittery and excited. When we arrived, Evan opened a drawer and announced, “I keep my cocks in a drawer.” 

I laughed, impressed by their confidence. 

They took out a few items and tossed them onto the bed for me to choose from. I stood there for a moment, studying the collection, feeling a bit overwhelmed. 

There was a large, rainbow dildo, a small black dildo, and a tan one with a slight curve that reminded me of my college boyfriend’s cock, and several others of various shapes, colors, and sizes. 

There were black leather harnesses, with and without studs, and a pair of underwear with a hole in the front. 

I started reaching for one of the harnesses, but Evan said, “Actually, I don’t think that’ll fit your thighs.” 

I pulled my hand back quickly, feeling my face flush. 

They picked up the underwear, the item I had found the least sexy and the least like something I would want to wear after someone else had. 

“This might be the only one that’ll fit you,” Evan said, so I took it. 

“Which of these do you like?” they asked, gesturing to the dildos and looking at me expectantly. Awkwardly, I picked up the tan one. 

The excitement I’d felt while talking about it at dinner was morphing into nervousness. Still, I continued, eager to live out my fantasy and not wanting to disappoint Evan. Before long, I was standing, naked but for the underwear and erection extending from my body. 

Seeing a Penis on my Body for the First Time 

It was strange. Good-strange? Not bad-strange, just strange. It certainly didn’t feel like part of my body, but it felt like it could be… I just needed some time with it. 

“How does it feel?” Evan asked, kneeling at the end of the bed, facing me. 

“Interesting,” I said touching it tentatively. 

When I didn’t respond, Evan added, “Some people like cock-worship.” 

Evan began playing with the dildo while I watched, willing myself to feel something through it, but failing. After a few moments, they rose up and began kissing me. I relaxed and began to feel again — I knew how to kiss. 

But that didn’t last long before they pushed me to my back and took the cock (the cock, still not feeling like my cock) and moved it inside of them. I lay on my back while they rode it. 

When Evan orgasmed, I felt the chaos of orgasm with none of the connected sensations, none of the pleasure. 

Is this what having sex with a penis is like? I found myself wondering for the second time in a decade, but this time, there was a very different emotion attached. 

Is this what having sex with a penis is like?

While this experience wasn’t ideal, the fantasy is still alive in me, and I’d like to eventually try it again. 

Next time though, I will do things differently. 

1. I’ll wait until I’m more comfortable with my partner. 

My relationship with Evan was pretty new, and, as close as I sometimes felt with them, it was far from the closeness I felt with my long-term boyfriend many years ago in college. I should have listened to the signals coming from my brain and body to slow down, stop, and check in, but I felt nervous and struggled to articulate it. If I try wearing a strap-on again, I’ll make sure I feel fully comfortable with my partner. 

2. I will be sober and intentional about the decision. 

While I hadn’t been drunk that night with Evan, we had been drinking a bit, and the decision to try this had been spontaneous. In the future, I will make sure it is a conscious decision, not one made over drinks, twenty minutes before doing it. 

3. I’ll select what I’ll be wearing, and not just from someone else’s collection. 

I didn’t like the feeling of picking out a toy for something that would be an extension of my body from someone else’s collection. Therefore, I’d like to purchase my own and empower myself to foster a relationship with this physical representation of what I’ve come to call my “energetic cock.” 

4. I’ll wear it alone for a little while before using it with a partner. 

I want to give myself time to really feel it as a part of my body, an extension of my energy, without the distraction of sharing it was someone else. 

“With Great Power Comes Great Responsibility” 

It may be cheesy to quote Spiderman, but I just quoted Spiderman. 

Having a part of your body that becomes hard (or is purchased hard) and can penetrate another person’s soft, vulnerable spaces is powerful. The human attached to it must take responsibility for it. 

I wasn’t prepared for the responsibility of wearing a strap-on, but in the future, I plan to be ready. 