The Risky Jerk 

The risky jerk is a very dangerous, ballsy move. You must stand next to your parent's bed while they are sleeping, and masterbate. You must complete all the way till release. The riskyness is doing this next the head of your sleeping parents, they could wake at any moment.

DUDE! I tryed to do the risky jerk but my dad woke up half way through and cut it off!

The Risky Jerk by Johnny Donn July 20, 2008

a risky one 

Bringing some excitement and a safe element of incest back into the gentlemanly pass time. Asking your mum to make you a cup of tea when your not even in the racing position, and then getting started, the idea being to finish yourself off before she arrives with your warm, refreshing beverage.
Extra points can be earned if you manage to regain your composure before she comes in, failure obviously carries its own punishment if you're in mid stroke as she comes comes in.
Also known as one of the Risk

Why don't you try a bit of R & R?
What rest and relaxation?
No Wrist and Risk action. Try having a risky one.

wank knockoneoffthewrist one off the wrist risk incest

a risky one by Etherial Moiety February 27, 2011

O.D. Risky

When a situaition is extremly risky and possibly could get you in trouble or hurt.They are best avoided.

Josh:Lets go smoke a bowl in my front yard
Jantzen:Thats O.D. Risky nigga,....your mom is still awake
(pause)
Jantzen:Fuck it,.....i wanna get high
Josh:Haha,OK

O.D. Risky by HighBoyz September 28, 2009

Doing the risky 

Do the risky (verb) When one is playing a game involving a bomb and defusing the bomb even though the enemy is staring directly at you

Why are you sticking the bomb idiot your Doing the Risky

Doing the risky by Snakey818281281 March 13, 2022

frisky risky 

to be amazingly daring while sexy at the same time and to be very good spaids players.

Would you like to play another round of spaids, frisky risky style?

frisky risky by Demetrious Lakrisha July 1, 2009

national risky text day 

National risky text day is may 25th.

Send a risky text to someone special

"Today's national risky text day"

national risky text day by bjasbsksisjdksizhxh May 25, 2021

Going Risky

Originally used for when a man knowingly had sex with a girl, who he knew had some type of std (sexually transmitted disease). He would wear a condom for protection, but the "risk" is that it might fail.
More commonly used when referring to dating (or just having casual sex) with someone you know you will have problems with in the future. The "risk"is the aftermath of the relationship.

"I was going risky with my math tutor class last night, but I think she wants a real relationship. That's gonna be a problem"

Going Risky by YourKngco December 19, 2011