A sexual position where the lower person (usually a guy) lays on its back and is erect and the person on top has inserted the erect member in her or himself inside themselves and "rides" the lower person. If the insertee is familiar with cowboy culture they can yell out "ride em cowboy!" sometimes wearing a cowboy hat to enhance the rodeo effect. The lower person is usually a male, but lesbian sex is known to have something similar. A woman could conceivably be the lower member if she were to wear a strap-on and hold it in place.
Gee Dale! Ride me cowgirl! I am Roy Rogers, remember?!"
by ArnoldZiffel November 20, 2013
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(I actually found this term in a Craigslist ad)

a) the phrase a gay man will use in a Craigslist ad when he specifically wants anal sex from another gay man

b) what a straight submissive man might say to his yang when he wants her to just sit on his phallic organ and ride herself to orgasm
yo baby, ride me like a rodeo definition b)
by Sexydimma November 23, 2016
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im from the cpt on a robbing spree a muthafuking g bitch - let me ride
by hey what r u eating April 27, 2005
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When clothing is cutting off circulation or is hurting your body.
Damn... is it just me or these undies are riding up on me.
by Mr.Kark September 7, 2019
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When clothing is cutting off circulation or is hurting you. Usually if the clothing is too small.
by Mr.Kark September 7, 2019
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Best song ever. Made by T.I in 2006.
"-Aah shiit did u hear the song made by T.I?? Its called Ride wit me!"
by Gardulf November 13, 2016
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