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An unfortunate genital mismatch. Either the woman's vagina is too loose or the man's penis is too small/thin, hence 'It didn't touch the sides'. Also used to disparage a woman by suggesting she has been too promiscuous.
I really liked him but when we had sex it didn't touch the sides.
by CalSouth March 11, 2015
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Switch Sides

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After Joan divorced her husband, she decided to switch sides and be with another woman.
by kanaan316 April 9, 2022
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sideswipe

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the process of masturbating by rubbing the penis on the inside of the left or right thigh with the opposite hand
Dude, i had a super-satisfying sideswipe session yesterday.
by rinkle123 January 5, 2011
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Riding Sidesaddle

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A term applying to men who have recently been to the Snip Doctor to have their plums done.
He's currently "riding sidesaddle" but I'm sure he'll back to normal when they've healed up.
by Luciano Lovelace February 4, 2004
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sideshot

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when your taking a whizz and it slighty flies to the side
Damn this is my 5th sideshot this week
by Adonis Rosalle May 19, 2005
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Sideswiped

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When a guy feels like he was just hit by a car because his girlfriend that he thought was just a casual relationship wants him to tell her he loves her, and or she tells him that she wants to get married.
Bob really got sideswiped last night when Tina told him that she wanted to get married. I feel bad for the guy, but oh well he's pussy whipped anyway.
by Soaren Nidabroht December 2, 2010
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Sidestep

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When someone who owes you money completely changes the subject of conversation when asked about the debt in order to avoid said debt.
Chad completely sidestepped me today when I asked him for the money he owes me.

Me.. Hey you got that 20 you owe me?

Chad... Did you hear about Danny going to jail last night?
by JohnnyTrapp77 April 17, 2019
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