Inside the magazine, it’s revealed that the winner of the contest would actually receive a pillowcase with his face on it and the book “Donald Trump: The Man, The Myth, The Scandal.” By Joel Reed. In August 1990, he was publicly dating actress and model Marla Maples after his divorce from Ivana was settled earlier in the year.
Serious_Specter on
I’m more interested in the 69 things I could do with my tongue.
TheDefected on
He doesn’t look too bad there, to be fair.
LevelGrounded on
And nobody entered.
McLuvin1589 on
That must have been the legendary “female gaze” I hear about.
TheKramer89 on
Seems kinda gay…
Sir_Justin on
Seems a little expensive for 1990
No_Barracuda8791 on
Even at his “best” he was a gross fuggo. I can’t imagine anyone decent wanted to do this.
Possibly_A_Person125 on
Ew
Avantasian538 on
Or you could do something more enjoyable like eat broken glass.
atomsmasher66 on
Personal_Comb_6745 on
The twist is that anybody reading Playgirl was already too old for Donald.
HelloThere4123 on
🤢
Old-Custard-5665 on
I remember when Mike Honcho was on the cover
Guy626 on
So was that the prize? Or like what the loser got?
trampus1 on
What do you get if you win?
Lances_Looky_Loo on
Seems more like a punishment.
Oograr on
Second Prize was ‘Sleeping with Donald Trump Twice’
crottesdenez on
That guy has a super underwhelming build.
ImTooSaxy on
Dare how dare that dirty magazine slander Trump’s good Christian name!!
Loo-Hoo-Zuh-Er on
How much did he pay for that advertisement?
Cheeky_Chipmunk75 on
Clever layout – Donald Trump That Prick!
GeorgeStamper on
A contest to get genital herpes.
trollsmurf on
There are women that fawn for imprisoned murderers. Just saying.
R_Larsen86 on
Do the dudes in Playgirl pose with boners, or are they just hanging around? Really don’t feel like looking on Google.
BaseHitToLeft on
He must have been missing Bubba
Kenomachino on
And two years later he was in Home Alone 2. Coincidence?!
Couldnotbehelpd on
Play girl magazine tried really really really really hard to act like their readership wasn’t 96% gay men.
28 Comments
Inside the magazine, it’s revealed that the winner of the contest would actually receive a pillowcase with his face on it and the book “Donald Trump: The Man, The Myth, The Scandal.” By Joel Reed. In August 1990, he was publicly dating actress and model Marla Maples after his divorce from Ivana was settled earlier in the year.
I’m more interested in the 69 things I could do with my tongue.
He doesn’t look too bad there, to be fair.
And nobody entered.
That must have been the legendary “female gaze” I hear about.
Seems kinda gay…
Seems a little expensive for 1990
Even at his “best” he was a gross fuggo. I can’t imagine anyone decent wanted to do this.
Ew
Or you could do something more enjoyable like eat broken glass.
The twist is that anybody reading Playgirl was already too old for Donald.
🤢
I remember when Mike Honcho was on the cover
So was that the prize? Or like what the loser got?
What do you get if you win?
Seems more like a punishment.
Second Prize was ‘Sleeping with Donald Trump Twice’
That guy has a super underwhelming build.
Dare how dare that dirty magazine slander Trump’s good Christian name!!
How much did he pay for that advertisement?
Clever layout – Donald Trump That Prick!
A contest to get genital herpes.
There are women that fawn for imprisoned murderers. Just saying.
Do the dudes in Playgirl pose with boners, or are they just hanging around? Really don’t feel like looking on Google.
He must have been missing Bubba
And two years later he was in Home Alone 2. Coincidence?!
Play girl magazine tried really really really really hard to act like their readership wasn’t 96% gay men.