I'm a 40-year-old cis gay man who has generally lived his life as a bottom. I have topped from time to time in my life, it's something I can do, but it isn't very fulfilling. I soften up after five or ten minutes (even with ED meds) and I never ever come from topping. The big revelation came this weekend at a leather event. In the week before, I developed a fissure, so bottoming would be off the menu, and for the first time, I'd present myself as a top. (I seem to be the only gay man who doesn't at all enjoy oral sex, so let's put that aside for now.) It was astounding how different things were, how much more attention and action I got: more that weekend than in all of 2019 put together. And yes, I know quality is more important than quantity, but also, if you eat ten apples you're more likely to find a really good one than if you only eat two, right?

I would like to live that life every time I go to an event, and probably at home too. But, even though I greatly enjoyed how I felt inside, I didn't really get much pleasure from how I felt outside. I would inevitably soften up after ten minutes or so (even while fucking a guy I'd fantasized about for years!), and the only time I came was when I pulled out, closed my eyes and tried really really hard to imagine what the bottom was feeling, and jacked myself off. I've bottomed enough to know that's not especially desirable top behavior.

Also, as I age, I'm starting to look more and more like a daddy bear, a physical type that most people (myself included) prefer to fantasize about in the top role. So everything is telling me that I should be more and more of a top. But how do I rewire my brain or my body to start to enjoy it physically?

Changing Roles Is Super Promising

Have you tried topping with a butt plug in? — Dan

GOOD TIP! Lemme give that a try! Thank you! — CRISP