Maybe I ... Like Small Penises?!

Perhaps I need one in every size.

Jun 28, 2025

A few weeks ago, I went on a first date with a married, ethically non-monogamous artist entrepreneur I met on Tinder. We met for drinks and wandered around the neighborhood. At one point, he said “let’s go for a walk,” and I sensed that he wanted to find a place to sit and make out. I said as much, and he feigned innocence. “We’re just walking,” he insisted. Eventually we wandered past a picturesque bench nestled in a park that was occupied by another couple. He sighed. I laughed. Then we started kissing on the sidewalk.

At first, I wasn’t really sure how I felt about him. I didn’t invite him home with me. I didn’t love his breath and his kissing was a bit robotic and unresponsive. He was also small — short, yes, and I don’t mind that, but also quite thin, and I tend prefer stockier guys. I want something to grab onto. But he had a sexy, quiet, intense way about him. He would look at me, and it felt like he was going to light my insides on fire. He was also genuinely interested in me, asking good questions and remembering details. Over text, he was thoughtful and kind and seemed emotionally intelligent.

So less than a week later, we planned a second date. A sex date. I figured: Why not try it at least once? It was a weekday evening and he came to my house and brought a bottle of good red wine. We sat on my couch sipping it and talking and then boom, we were making out. His breath was better. The kissing was improving. The couch was squeaking. We moved to the bed.

Slowly, we started undressing. First, his shirt. Then, his jeans. I felt him, hard, through his underwear.

And then I realized: Oh. Shit. This guy is tiny.

The disappointment washed over me immediately. I wasn’t sure I’d ever been with a guy this small before. But, hey, we’d come this far…. So we kept going, and I hoped for the best. (Also, silver lining: blowjobs are a breeze when you're working with travel-sized equipment! I could have done that all day.)

Maybe because he has felt the need to make up for his size limitations, he was really good at foreplay. The way he kissed my nipples and around them, the way he touched me…. it was all very hot, and I soon became quite turned on.

He put on a condom and slid inside me, and, yeah, I initially felt underwhelmed. I remember thinking, “this is just so…. superficial.” I couldn’t feel him as deeply as I wanted to. It wasn’t bad; I simply wanted more.

And yet, somehow, I still started enjoying it. I wanted more, yes, but what I was getting was still really good. It felt like his penis was tickling and teasing me rather than overwhelming me, and… well, I kind of appreciated the subtlety. Although I rarely orgasm with the help of my fingers (I typically need a vibrator), I reached down to touch myself, just to see. Suddenly, I was orgasming. We kept going. I touched myself and orgasmed again.

I can’t remember the last time I’ve orgasmed twice in a row with my hand. It’s been at least ten years. I was aghast. And rather thrilled.

And lying on my bed in the throes of pleasure, I had an epiphany.

I have always been easily overstimulated by touch. Too much on my nipples or my clit and I am toast. Was it possible that larger penises also overstimulated my vagina, making it harder for me to orgasm? I do enjoy the intensity of deep penetration, but perhaps when it comes to climaxing, less in my vagina is actually more. Or, maybe, a shorter penis better stimulates my G-spot. I don’t know. All I know is that I haven’t orgasmed during sex this easily in a very long time.

The next time we had sex, a few days later, in the morning after he brought me good coffee, I almost orgasmed without touching myself at all. That hasn’t happened since I was 25.

My friends joke that I need a stable of men to satisfy my sexual needs, and I’m starting to think I require stable of different penises, actually. The more of them I try, the more I learn about myself, and the more I discover that my body has the capacity for many different kinds of pleasure.

This experience also makes me wonder: What else have I wrongly assumed about sex — and about myself? It’s easy to believe that by our mid-40s, we already know everything we need to know about what we like. But that doesn’t seem to be holding true. Bodies and preferences change over time, and they do not conform to the reductive scripts we have been fed throughout our lives. We shouldn’t just be searching for what we think we want, I’m realizing; we should try to stay curious. Pleasure isn’t something we discover once and lock into place. It’s a continually unfolding story that might take us places we don’t expect.