A women (or man) who ride 7 or more dicks at once.
Regina is a proud Rough Rider.
by CookAfRoginmyVanEverydayReal January 23, 2018
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You're doing a girl from behind, and you pull her hair back to your pubs. Then you braid her hair into your pubs and slap her ass so she yanks her head forward which will pull your pubs out. It is a little bit of pain and pleasure mixed. (French Braid for the best results!)
by Andrew-Micheal December 2, 2006
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A group of bad ass individuals who roam the streets of middle town with there auto mobiles, they most likely don't give a fuck and can down a bottle of vodka within 3 seconds they know how to handle a gun but rarely use it, they rather use there fists and a broken bottle of jack Daniels to teach a bitch whats up.
Danny- did you hear what happened to drew?
Anthony- no what?
Danny- he got mugged and shoved down a sewage drain with only 1 sock on his foot.
Anthony- damn "Middletown Rough Riders" rided another bitch.
by The Game 2.0 November 4, 2011
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high school aged rednecks who like to tailgate at sheetz gas station parking lots; most sheetz rough riders drive lifted pickup trucks or rice burners
the sheetz rough riders were revving their sick truck and ricer engines at 1 am in the sheetz parking lot
by 69anonymous6969 March 8, 2013
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First, slather your johnson with freshly ground ginger and add cayenne pepper to taste. Next, find a sturdy young stallion and gently mount him. While he is grazing, suddenly and powerfully penetrate him from behind while keeping a firm grip on his buttocks. He should be off like a shot. Hang on for the ride of your life.
Steve: The other day I saw this horse so I had myself a good old rotterdam rough rider
Dan: Holy hell man, is your dick alright?
Steve: Still recovering bro
by P3RV-E November 6, 2014
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The act of using maple syrup as lubrication. Makes some sticky sweet love making.
Yeah last night we did the Canadian rough rider... made her ass taste much better
by Ddubs September 30, 2014
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