WIN IT: The First Four Issues of Headmaster

Headmaster magazine

Today for Reader Appreciation Month, we’ll be choosing ONE lucky winner to receive the first four issues of Headmaster for free. Headmaster is, in their own words, “the biannual print magazine for the sophisticated man-lover who appreciates smart writing and thought-provoking art”, so this giveaway is quite the departure from our previous porn, lube and t-shirt contests.

The rules are also very different!

For starters, we won’t technically be choosing that ONE lucky winner. Headmaster has brought in a guest judge, erotic fiction publisher and writer Johnny Murdoc. He’ll be analyzing your responses to the following assignment:

“Write a story of EXACTLY five sentences about an imaginary encounter involving you and a famous person whom you find attractive. Creativity is encouraged. Smut is not discouraged (but also not required). If it helps, remember that fame is a relative concept. Also, the famous person need not be currently alive, though stories about real famous people are preferred over stories about fictional famous people.”

Your story should be sent to before noon on Friday, November 30. Please include a pen-name in your e-mail, as there’s a possibility that the best entries will be published on Headmaster‘s site.

Speaking of which, did I mention that Headmaster relaunched their site today? They’re having a holiday sale!

– Dewitt

Click through for images from all four issues and last Friday’s winners:

Jason Tranchida & Jorge Urena (Issue 1)


Jesse Burke, designs by Joseph Segal & House of Cach (Issue 2):


Matthew Lawrence, featuring Steve Cruz and various porn stars (Issue 3):


House of Cach (Issue 4):





To get a free membership to Parole Him, we asked you all: “In your cop-related fantasies, would you fuck the police, get fucked by the police or play the role of the officer himself?” These were the four winning responses…

1) polecatjohnny: “Since the police do all the fucking, I would definately turn the tables. And some things go without saying, the nightstick would be involved. I consider fucking a cop to be on every gay man’s checklist, like a priest. I know some cute cops peronally, but not intimately. But they are the good ones. If I met a nice cute corrupt one, like Quinn on Dexter, how easy would that be to get him to spread ’em? Just gotta put a little money in the bag. But I don’t wanna part with my money, so I d just blackmail him and take charge. And to boot, we’d do it in his cop car, hopefully with the blue and red lights flashing, lol.”

2) DieSeL_jock: “Man…I have a few cop fantasies. I’d have to say the hottest would be to get to fucked by a beefy cop (in uniform) on the hood/trunk of his car. As he’s pounding me, a backup officer would show up, and they’d manhandle me from both ends. I’d shoot hands-free a couple of times from their deep-dicking, then they’d cover my face with two massive cumloads. After they finish with me, they’d suit up and leave me there drenched.”


3) brettp99: “In my fantasy, I’m not doing any of the fucking at the beginning. This big burly cop is questioning me and a friend about why we were having sex in public and has both of us in handcuffs. He comes over and undoes my friend, then asks us if we “finished” before he came and took us away. He says no, and then the cop asks if we want to! I’m still in handcuffs and the cop starts rubbing my friend. They start making out, and my friend strips. The cop keeps his clothes on and just unzips his pants. My friend pulls out his dick and starts blowing him. I’m still in handcuffs, fully clothed with a raging hard-on watching this happen. He bends my friend over and rims him, all while he’s looking at me. Once he’s all wet, he starts fucking him. I’m still watching, the hardest my dick’s ever been. The cop asks me what I want him to do to my friend… I tell him to use his nightstick on his hole and make him suck me off finally. My friend’s mouth never felt so good. The cop makes my friend shoot his load without even touching his dick. I shoot mine in his mouth while he’s blowing me. The cop pulls out and shoots his load all over my dick and makes my friend lick me clean.”

4) BrainySmurf83: “Four words, one hot scenario: good cop, bad cop. I’d be the bad cop. Some sexy bottom, let’s say Dean Monroe, would be good cop. Another hot top, let’s say Austin Wilde, would be the criminal. At first Dean and I would be interrogating Austin, but then as the bad cop, I get tired of Dean’s weak questioning, and then Austin and I take turns going to town on Dean (not to mention, my ultimate fantasy in this situation: fucking Dean Monroe while sucking Austin’s nice dick!). It ends with Dean covered in my cum, Austin’s and his own.”

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