Too have sex with jaye Robbo after she has played Russian roulette with her pill and sugar pills. You either get a baby and $5000 baby bonus or win and escape baby entrapment!!
by Lime3&4 August 19, 2014

by brobroseriouslynotme March 13, 2016

When you blow your load before you know who you are having sex with, similarly to a sheriff in the Old West shooting a man before he knows whether he is friend or foe. A high risk gamble indeed.
Jack: "It's a good thing it was my girlfriend I took into the closet, I was a real risky sheriff last night."
Joe: "That's fucked up, dude."
Joe: "That's fucked up, dude."
by tsmagraw February 19, 2015

The act of when a man has sexual intercourse with a partner next to his or her sleeping father and busts a fat nut on his face
Kyle: Dude i just got my ass beat cause i pulled the risky jizzky last night at my girls house
Chad: Ah no way Bro
Chad: Ah no way Bro
by Xx_Pornhub_xX July 2, 2020

by Johnbernthal March 25, 2022

John: Dude last night i had sex with this total slutbag and she had herpes, AIDS, Gonorrhea, Syphilis and Swine Flu.
Jim: Thats some risky biz right there bro.
Mother: Did you atleast where a condom?
John: Nope im a beast, what can I say?
Mother: That really is some super risky biz.
Jim: Thats some risky biz right there bro.
Mother: Did you atleast where a condom?
John: Nope im a beast, what can I say?
Mother: That really is some super risky biz.
by Beasterface July 31, 2009

Jonny and his girlfriend were broke and horny, so they jumped in the backseat of his car for some Risky Business
by XSTUTCHX March 9, 2009
