Caption This: Hit It From The Back 
08 February 2011

We didn’t plan on using another funny porn face for this week’s Caption This contest. However, we quickly changed our minds upon catching this shot of Dean Monroe bent over for Alexsander Freitas. Is he experiencing an intense moment of pleasure? Or is he unable to handle the monstrous uncut cock probing his prostate? It’s impossible to say.

If you’re up for the challenge, leave a comment with your wittiest (or sexiest) caption for this image. We’ll sift through the entries for the best of the bunch and post the winner in next week’s Caption This 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

Photo credit: Butch Dixon

To check out last week’s winning caption, follow the JUMP:

Kudos to Kenny for keeping it simple. Though we appreciated this snarky remark.

  • alaskaman

    sorry mate, I think I got something in my eye!

  • JwithG

    This wasn’t how you explained the prostate exam to me over the phone.

  • Almanzajoe

    Wait my cock… Oh fuck.. fuck it…

  • Dan

    why has Tom Chase changed his name….Dean Monroe looks like his twin brother..! Hot!

  • Pretty Much An A**hole

    I said just the tip to see how it feels.

  • Jason

    E… F…. P…..T…..O…..Z…… How’m I doin’ Doc?

  • Fourunknownreasons

    ” a–ka-ka-ka, WELL BLOWS ME DOWN!”

    his impersonation of Popeye…. lol

  • Jason

    Alexsander found One-Eyed Willie’s treasure.

  • Bottomsupboy

    I said ‘stick it in my hole,’ not make a new one!

  • homegrown84

    OH SHIT! I’m switching to Allstate!

  • cocksrhot

    Grunts… I’m going to feel that in the morning!

  • Sometipsforlife

    In this tender moment, Dean Monroe quietly reflects on his career.

  • frederick

    Ahhhhhhhhhh…..popped it!

  • kickedback78

    Eh, What’s up doc!?!

  • Thomik

    Uhhhhh, I think you took a wrong turn.

  • Thomik

    That’s all for Weekend Update! Thank you & have a pleasant tomorrow.

  • DS

    Oh damn… its 2 o’clock…. Ninja poop time….

  • Anthony

    To the left to the left. All yo’ cock is curved way to far to the left.

  • Caesarromantx

    Thats NOT the area I want Tatooed!

  • Hman

    step back, think I just put my cock in an electrical socket

  • Ahhhhhhhh!

    Now this one is without the condom….

  • Miguel1

    Hey back up on it a little so i ca n get the head in. It won’t hurt one bit.

  • Cuteman43

    Not so hard you are about to poke my eye out.

  • Woody

    Just a little to the right, PLEASE !

  • Hman

    Dam didn’t mean to shoot that far

  • JC

    That’s cold …go faster.

  • Leebaz

    sometimes you feel like a nut, sometimes you don’t…

  • Thomasword

    i actually think your fuckin my brains out of my eye!

  • MS

    Did that tattoo say “Objects in mirror are larger than they appear?”

  • Grant

    Uh oh! Here comes lunch

  • timmy

    Thats for stealing connan obrians hair style!

  • dartcene

    Dude. Are you sure this is the last place you saw your keys? Cuz, I don’t see them…

  • MrLowballs

    Damn! What’s gotten into me?

  • MrLowballs

    Damn! What has gotten into me lately?

  • Kenny

    In the voice of Popeye:
    “Shiver me timbers!”

  • http://pulse.yahoo.com/_RY7XRUC5SIQIN3YUKQISK6S73M Phillip

    Oh, it tickles…

  • rp

    Ough! Fire in the hole!

  • Peterpuffslv

    Right eye out!

  • JC

    That’s the one place I didn’t lose my contact lense!

  • chii

    not a suggestion — just an observation — but shit, Dean Monroe is lookin’ rough.

  • Charley H.

    Is that Ricky Martin behind me?

  • stoudy

    Are you shitting me?

  • stoudy

    “Are you shitting me?”

  • PJ

    “Huh? They said I was getting a Brazilian!”

  • JTC

    Ohhhh Thats gonna leak in the morning.

  • CC

    Where will you be when your laxative kicks in?

  • The Doc

    Watch out for my gerbil

  • Dan

    A little to the left…

  • kickedback78

    Warning! Good sex may sometimes lead to strokes, which can lead to facial paralysis and often f*@cked up facial expressions.

  • http://www.MaleEroticEvolution.com Michael!

    That really doesn’t feel like a tattoo gun you’re using back there.

  • Jayson

    AHH….Splinters!

  • ImJustCheckin

    Damn, shoulda bought some lube..

  • Emmdee

    Is he being fucked by a wall of graffiti?

  • Jason

    I actually thought the same thing but didn’t want to mention it! lol

  • Tshirt501s

    Now let me see …..I’m guessing Alexsander.. am I right!

  • disrespectful dude

    what’s an enema?

  • Anonymous

    *he* thinks I’m moaning because of him… Thanks Fleshlight! *wink*

  • Neil_Anblomi

    Oh Man! His dick is longer than it appears…

  • Justlou

    It burns!

  • Oksoiam12

    More LUBE please

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