Dear Black Gay Men’s Substack

Dear Black Gay Men’s Substack

The Untrained Hole: What Tops Don't Understand About Bottoming

When you want to bottom but your hole just won't cooperate.

Jai The Gentleman's avatar
Jai The Gentleman
Nov 26, 2025
∙ Paid

Brunch with Bottoms

I went to brunch sitting at a table full of men who identify themselves as bottoms. Some masculine. Some feminine. Some taken. Some single. But all bottoms.

Then there’s me: an aspiring vers top at best. I haven’t taken dick in years. Wouldn’t know the first thing about cleaning out appropriately or when and how or what to breathe through. Yet, for the first time in my life, I want to give my delicate flower to someone.

Vers-ish

Ryan, my boyfriend, is slowly becoming the love of my life. He is domesticating me, so my best friends say. I’m buying flowers just to see his face light up. Holding doors because he means that much to me. Picking him up for dates, and walking on the outside of the sidewalk because I’m a gentleman FOR HIM.

And his dick is big.

It’s pretty and veiny. It’s substantial and girthy. It’s the kind of penis any vers man would be excited to mount.

Problem is, I’m not vers.


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Delayed Gratification

Bottoming is a skill that mere tops could never imagine. It’s a mind-body connectedness that says “a brief discomfort on insertion is worth the pleasure of balls deep”.

It’s delayed gratification personified.

The Pleasure of Topping

But topping isn’t set up like that. Every moment of giving dick is pleasure. Men have more pleasure sensors in the head of the penis than any other part of the body. From the head you give us to get it up, the tap on the hole thing we do before we stick it in, to every moment once we’re inside, everything is pleasure.

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