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1. To ride in the front passenger seat. The phrase is a direct allusion to the armed guard who sat beside the stagecoach driver
2. To keep a watchful eye on something or someone
Jon gets sick during long trips so he always prefers to ride shotgun
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Earning the right to ride in the front passenger seat of someone's car. This is also the direct opposite of "riding bitch," where you are sitting center-backseat, sandwiched by your friends (aka: riding gay, riding whore). It is "shotgun"'s responsibility for controlling car temperature, changing radio stations, calling out landmarks, and flagging down hot girls.
Variations to "calling shotgun" can include paper/rock/scisors, coin flip, or being the first to yell "shotgun" when the driver pulls their car keys out of their pocket. Seniority rarely means anything when calling shotgun.
Steve was riding shotgun because he won the coin flip in the mall.
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Having cowboy/cowgirl sex with a girl whose "paw" would likely make you marry her at da barrel of a thirty-aught-six side-by-side if he found out.
Hey, if you wanna risk having a roll in da hay with a hot-bodied farmer's daughter, knock yourself out, but just bear in mind dat you might likely be "riding shotgun", especially if you get said lovely damsel preggo --- remember, da cuter/sweeter da angelic-faced girl is, da more fiercely-protective her "paw" is likely to be.
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When a woman climbs on top of a guy just before he blows it. Any variation of girl on top applies - cowgirl, reverse cowgirl, etc.
She was riding shotgun for all of 5 seconds before he filled her with a hot blast of dick sauce
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Where you hang out a window doing a drive-by
In Grand Theft Auto San Andreas you can be Riding Shotgun
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A sexual act in which one person sits on the face of another and is penetrated by nose (Anally or Vaginally).
Person A: “My nose is stuffy as hell!”
Person B: “You sick?”
Person A: “Nah, my girl was just riding shotgun.”
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