A ridiculously enthusiastic personage. Convinced that everything's going to come up roses. Incapable of touching anything that will not, inevitably, fuck up. Completely unaware that the world will fall around his ankels once agin.
"Oh, well done, Guesty, that's worked a fucking treat, hasn't it"
"Yeah, Guesty, I'll put my money on that next ime, you chump"
"Yeah, Guesty, I'll put my money on that next ime, you chump"
by james November 16, 2003
someone who is critically acclaimed by fellow classmates for being unequivocally individual for his/her actions.
a boy walked into class one morning wearing nothing but a pair of claret and blue y-fronts. The boy in the front row of the class exclaimed, "he's a real guesty, that one!"
by George J.G March 6, 2007
When you're giving it to her hard doggy style and spanking that ass, then when you're about to cum pull it out quickly and stick it in her ass and blow your load!
She thought I was going to cum in that pussy but instead I surprise slipped it in her ass and shot my load!! I gave her a Dirty Guesty!
by BigGuesty August 20, 2021
by ItsJKCoolGuy May 4, 2021