tootsie rolling 

the act of corn holing your girl friend. then leaving unshowered back home. squirt some hersheys syrup on your frank to mask the smell an get a blowjob from your wife.

my dam wife wanted me to clean the garage so i ended up tootsie rolling her ass.

tootsie rolling by redwood boner March 1, 2012

Tootsie Rolling 

Getting high by eating a pill of ecstasy after failing to successfully go colon rollin' (getting high by using a pill of ecstasy as a suppository).

She was way too fucked up to successfully shove that pill in her ass, but she wanted to get high badly enough to go tootsie rolling.

Tootsie Rolling by ababyinablender July 7, 2009

tootsie rolling 

Leaving a large group of your female friends, to go to another room and talk for prolonged periods of time with a boyfriend or guy you are interested in.

See cupcaking (for males).

Julie stays tootsie rolling with that new guy, Gary. It was supposed to be girl's night out...he is pretty cute though.

tootsie rolling by Threfty March 7, 2010

Tootsie Rollin

The sexual act of passing a solid piece of fecal matter back and forth between two anuses while reaching through each others legs and helping to manually release your parter.

When two people bend over,press their spread asses together, and one shits into the others ass and it is passed back while your jerk and finger each other to orgasm.

Shit girl me and my man was tootsie rollin last night.

So i kidnapped these two sluts and forced them into some tootsie rollin.

Tootsie Rollin by Stubs Magnificent July 6, 2008