Gay Porn Flashback: Derrek Diamond’s Garish (Yet Romantic!) Playgirl Spread

Before he got his start with Randy Blue and before he became a Raging Stallion exclusive and wayyyy before he retired and made my life not worth living, Derrek Diamond (a.k.a. “Derrick Diamond” depending on where you’re looking) posed in one of the most horrifically cheesy Playgirl layouts of all time. On the one hand: Ugh. On the other: Awww.

The stylist for this shoot had a thing for RED! I hope this evoked whatever mood it was supposed to evoke at the time (Valentine’s Day? The end of Carrie?), and all the color coordinated props didn’t eclipse the fact that Derrek Diamond, the most perfect person in the world, was sitting there naked. Miss you forever, DD.

The spread inexplicably had just one shot of Derrek’s butt, which isn’t right. So here it is on display, and in Erik Rhodes’ face, in Pledgemaster: The Hazing. Watch in full here.

[Pledgemaster: The Hazing]

 

7 thoughts on “Gay Porn Flashback: Derrek Diamond’s Garish (Yet Romantic!) Playgirl Spread”

  1. Wasn’t it just last year he retired? That’s hardly a long time, although from the interviews he gave, it seems like he most likely won’t be back. Also, his layout was a centerfold and I think he was the last regular centerfold they had in their print edition of the magazine before they went online only. I think “Playgirl” is now doing a handful of special editions per year.

  2. Thanks for the sexy shots of handsome Derrek, you rarely see any good ones of him for some reason that show what a real hottie he indeed was/is. He has not been gone all that long really and as we all can tell he is missed.

  3. That much red reminds me of Bergman’s “Cries and Whispers” which if Zach could prove to me he’s seen, or knows who Bergman is, I’d shell out for him to buy “Derrick” for a Friday night. (Oh they’re all for sale).

  4. Love Derrek, he had a gorgeous face, gorgeous body, gorgeous cock and he always seemed really nice too. I do hope he and his partner are happy together.

  5. not to say derek isn’t a hottie, but he has been out of the biz for what seems like a couple years now. I’m all for joining your quixotic quest to revive his career, but is he even listening?
    don’t we have more recent porn shenanigans to blog about?

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