4 definitions by Jay Shepherd
The next level of the Milwaukee Tootsie Pop. Instead of stopping at just shitting inside your Pink Sock, you have your friend or lover ejaculate on the feces filled prolapsed anus.
"I was going to just have a Milwaukee Tootsie Pop, but then Victor sneezed and accidentally jizzed on it. Now its a Cream City Tootsie Pop."
by Jay Shepherd May 27, 2023
The reverse of the Milwaukee Tootsie Pop. Instead of shitting inside of your Pink Sock, you have your friend or lover shit ON your prolapsed anus. The feces-covered pink mass dangling out of your ass thus resembles a chocolate strawberry.
"Ricky thought it be funny to shit on my Pink Sock. This is one gnarly Milwaukee Chocolate Strawberry."
by Jay Shepherd May 27, 2023
"Ah man, I should not have eaten all that Mexican Food before I got anally plundered. I'm not going to be able to hold my shit in much longer and my Pink Sock is going to become a Milwaukee Tootsie Pop."
by Jay Shepherd May 26, 2023
Just like the Milwaukee Chocolate Strawberry, except you don't have your friend or lover stop at shitting on your Pink Sock. You then go on to have a friend or lover ejaculate on the feces covered prolapsed anus. Its important to note that it can be the same individual or different individuals who shit and jizz on the pink mass dangling out of your asshole. It can also be multiple individuals doing the shitting and cumming. Also, it does not matter what comes first. It can be the steaming wet shit or the white hot load that gets blown on your prolapsed anus first.
"I already was dealing with a Milwaukee Chocolate Strawberry when Carl had a big wet poop on my Pink Sock. But then of course Ronnie, Tee and Corey thought it would be funny to jizz on it too. Now I'm stuck with one hell of a Cream City Chocolate Strawberry."
by Jay Shepherd May 27, 2023