Dick Diaries: “Last hole you entered, where, when and who?” 🕳️

We will never back down from asking the hard hitting questions.

Happy Friday,

In this edition of the ‘Best of Dick Diaries’ we look back at some answers to the age old question: what was the last hole you entered?

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It’s something that simply MUST be asked, and trust we aren’t afraid to ask it.

Please enjoy some of the most revealing responses to this pressing and important question below:

Gabe

I’m really more of a bottom for the most part, but I’ve been enjoying topping more and more. Entering my vers era I suppose. I think the last time I topped was on Fire Island at the end of the summer. I slipped a cock ring on and worked this daddy’s hole for a while as a party was happening outside the bedroom door. He had a mirror over the bed and seeing his face in the mirror as I pounded him from behind had me rock hard. READ MORE

David & Little Beef

My boyfriend’s, at this hotel called The Gaythering in Miami, which also happens to be the first place we hooked up 3 years ago. Full circle! READ MORE

Quinn & his Ramming Rod'

Last hole I entered was last weekend and it was an acquaintance at his place and we flip fucked the whole night. It was very hot. I definitely want to do it again with him. READ MORE

Jack & Lil Rockard

@Jaxonvers on twitter, we fucked in my dungeon studio in Manchester for a movie we were making. READ MORE

Mark & Bo

Face down, ass up scenario a couple weeks ago. No idea who it was but their hole was dreamy and they seemed to like what I was laying down. READ MORE

Troy Ladstrong