Caption ThisHot Guys
cowboy hat
February 3, 2014

Caption This: The Cowboy Hat

This one’s pretty simple! A college frat boy reclines outdoors with his arms behind his head, showing off his hairy pits and spreading his legs wide open in a pair of short orange swim trunks. A cowboy hat rests over his crotch, begging us to ask the question—what’s he hiding under there? His beer? His Fleshjack? His pet Mogwai? You get to tell the story in today’s round of Caption This.

If you’re up for the challenge, leave a comment with your wittiest (or sexiest) caption for the image below. We’ll sift through the entries for the best of the bunch and post the winner in next week’s post. Think you have what it takes? Prove it, you cocky motherfucker!

For those of you who aren’t coming up with anything good, we encourage you to click through, check out the current submissions and show some support by “liking” another reader’s caption. Who knows? It might influence our final decision.

– Dewitt

Take a look at today’s image and last week’s winner below:



cowboy hat



one more piece of wood

With a whopping 42 votes, Bleuspecter crushed this round.



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29 Comments - View all

MikeyLikey 4:37pm on February 4, 2014

Tip that hat off to me, let me saddle up, and ride.

  • americanotico

    Whoa pardner, I only said “smoke” not “stroke”!!!

  • ubg469

    Wanna see me pull a rabbit outa my hat? Oops …. wrong hat!

  • xlbutt

    imagining a frat boy challenge … guys lined up on their knees with hands behind their back, having to go up between the guys legs to try and get the cowboy hat on their heads … kind of like bobbing for apples – only better. I don’t know how to caption this scenario however.

  • xlbutt

    if you ride reverse cowboy, you can keep the hat !

  • Graytwin

    This cow poke is from NYC, doesn’t know which head to wear his hat.

  • M Hairy, Love Hairy [Colt Men]

    Every tepee needs a pole, so why not my hat!

  • Gray

    After the Broncos lost the Superbowl, this is wear all bronco fans should wear their hats….

  • CupidsBeau

    “The sales clerk said it was ten gallons. I figured that’d be plenty big for a bukkake.”

  • Rob

    Now…for my NEXT hat trick…;)

  • Ed

    Save a horse, ride a cowboi!!!! How about a 10″ with that 10 gallon?

  • apothos

    THIS cowpoke needs some shade,dislikes getting burned……..

  • Bruce Strine

    That’s a mighty big hat for that size head.

  • Robby

    He must get his salsa from New York City

  • castle101

    I only take my hat off for one thing…

  • MikeGMU2

    Save a horse, ride a cowboy.

  • gcliff

    who wants to rub sunscreen on my cock?

  • blufur

    Texan sunscreen

  • Michael Mario

    “Save a horse, ride ME cowboy!”

  • MikeyLikey

    I think you put that hat on the wrong head…

  • Joey Thomas

    I can fill you up with ten gallons

  • Tye Hogan

    You know what real Scotsmen wear under their kilts….want me to show you what a real cowboy has under his hat?

  • aussie101

    hard hat

  • Seth

    A man left his hat to reserve his seat. I’m still waiting….

  • Kevin

    Looks like something’s Slytherin under the sorting hat

  • SkyRussell

    Save a horse. Ride a cowboy.

  • Joey Thomas

    The magic that’ll come out of this hat…

  • Iain Gardener

    Is that a ten gallon hat or are you just enjoying the show!

  • Dorian

    See what’s really BIGGER in Texas 😉

  • MikeyLikey

    Tip that hat off to me, let me saddle up, and ride.