When the length of a male's pubic hair surpasses the length of said male's penis.
"Hey man, do you think Charles is riding dirty?"
by Rotag McNeily August 30, 2006
Driving a car that is unclean, has a messed up paint job, has dents, doesn't have nice rims, or is just a hooptie. Riding dirty is the opposite of riding clean.
His '82 Cut Supreme was primer gray and half of the fender scraped the ground. He was riding dirty.
by Athena Pappas October 22, 2006
Slang term regarding a semi-legitimate business of contraband. Contraband being an act that bridges the gap between economies because though you may arrest people, others will rise up and some will make up new words for the industry like "riding dirty"....which is really jsut a cheap attempt at a rapper with no talent and alot of funding to "rise" to the top, if you will.

You know Run DMC??? they were IT.....they were good...or Sir Mixalot....see, that's classic, but this bullshit...it just sounds bad. Plus i mean what the hell, if you really want to make money without working hard and get women....you get a PhD.....it's actually not too hard.....gullable women will admire you and most of the work is on your own timing......you show up at work at 2pm.....or not at all if you dont feel like it. Then when your done you will likely get promoted and work alot less then a gangster and make maybe 6X as much. And women will want to fuck you, because your a "Dr." and they think that it's the shit.

That's where it's at FOOL!
Riding dirty is for pussies....the real playa's get the "Dr." then they get the women and the moolah....sucka.
by Dr. bullshit October 08, 2006
* Refers to a game played between friends where points are earned for succefully having sexual intercourse with extremely obese women without being caught by one's friends. If a participant is caught during this horrific act points are taken away and added to the finders point total. These women only qualify if their obesity is comperable to the fat women featured in Spencer's gag cards.

* The Chamillionaire song "Ridin'" was created to commemorate a specific instance where the artist won this game by sexually pleasuring a morbidly rotund transvestite. This event led to additional (bonus) points for Chamillionare which gave him a solid lead and eventuallty a win in a game between him and his friends.

My friends caught me riding dirty. Now I need too sleep with six fat bitches in order to win.
by John Ben August 23, 2006
1.driving with drugs or other illegal shit in your car
2.anal sex
3.sex with a filthy whore
Dylan: hey guys i had sex with mikes sister last night, then i shat on her chest

Kyle: thats fucking sick, you were riding dirty, and get away from me, you smell like shit.
by Super Cool Ben May 31, 2006
Galavanting about the beautiful countryside while having feces residing in one's own undergarments.
"what did i tell you about riding dirty in this household young man, I taught you better than that."

"Dude, this chick and I were totally making out, then i found out she was riding dirty. I left."
by The Ryder July 05, 2006
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