Do You Remember Seeing Your First Playboy?

One hump day after Hugh Hefner died of large, natural causes, six gentlemen share the first time they laid eyes on a Playboy magazine. Names are displayed in porn name form (middle name, first childhood street) to encourage more titillating detail.


I encountered my first two issues at the same time–both poorly hidden under my brother’s bed. One of them had Sharon Stone on the cover, which some googling tells me was the July 1990 issue. The other, I don’t remember who was on the cover but I do remember someone made the bold editorial choice to publish a photo of John Bobbitt’s severed penis. That image is still pretty fresh, but I can’t seem to recall any of the snaps from the Sharon Stone issue. So, you know … a real good news/bad news intro to sex. A song of fire and ice, if you will.

– Joseph Millview

When asked to wax nostalgic about my first Playboy magazine experience, I look back fondly and count my lucky stars I didn’t go blind.

After stumbling upon a secret stash of smut in the woods near my house (apparently a common phenomenon), the tantalizing cover of an early ’90s Playboy stopped me in my tracks. Like many, all it took was a few page turns and I was hooked.

As I settled in under a majestic cottonwood tree that still stands today, my eyes danced across each page in delight.

I got lost in dense, meaty content that stimulated me like never before. My mind mesmerized by otherworldly material as I furiously flipped through pages of hairy adventures and titillating tales with great anticipation of what came next.

Hours later, I left those woods forever changed. A whole new world had open for me, one spread far and wide that consumed me for years to come.

So when I look back, it was the immaculate Playboy writing that got me hooked. The articles and interviews made me the intellectual man I am today.

And for that, I am lucky to have never gone blind.

– Butler O’Brien

I was 12 years old out at our hunting camp property (middle of nowhere). My uncle had a deer blind that was close to the house and I wandered in there by myself and found a stack of like 20 playboys. My curiosity got the best of me so I had to see take a quick preview. Looked for about 2 minutes, got nervous and ran out but still felt like a bad ass.

– Louis Hardwood (best first childhood street name ever)

Not really a story, but I somehow came in possession of a magazine or 2 in the early middle school years I believe? Kept them stored in a small gapped slot in the backing of this old TV in the basement (my grandma’s old one, used for gaming, from the 1950’s likely) – right next to my VHS recorded copy of the movie, “Wild Things,” starring Matt Dillon, and Kevin Bacon….. Oh and I think Denise Richards might have been in that or something idk. Gotta take advantage of that free HBO, ya know.

– Clint Esther

I remember going over to a buddy’s house who dad was a ‘collector’. The Jenny McCarthy cover sticks out in my mind as an exceptional edition. I can’t really remember the jokes though ?

 – Jerome Oak

I was at a high school friend’s house for a sleepover with three buddies. (A charming, cozy lake house where the parents didn’t hover but we still always felt safe.) My friend had somehow secured three different editions, the first of which I believe had the Dahm triplets on the cover, but the pages of of my memory may be sticking together. I had so many questions. Triplets?! Was there any jealousy involved? Did one of them not want to do this? Where does their dad go from here? After quickly jumping over those hurdles, my brain was quickly spread eagle to a wondrous new world. Who were these amazing women? Were they at college? (The application process just took on a whole new meaning.) And the articles! They were a little graphic compared to the romantic novel excerpts I’d seen previously in Cosmo, but they were so interesting. This stuff actually happened to people?! The stories in Playboy unfortunately led to my friends and I sharing a few stories of our own, which inevitably got back to the girls at our school (who weren’t as open-minded about sharing them as everyone in the magazines seemed to be). Needless to say this didn’t go over well, and we all ended up needing the Playboys a lot more than we ever thought we would.

– Jeffrey Glenwood


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