When you hear someone say "fuck me sideways" they do not mean that literally, unless you are in the same room as a person and you both for some odd reason have your pants down. The actual meaning of it is "DAMN IT WHAT THE FUCK"
Setting : Imagine you are in a game and your friend kills you.
*Friend kills you
Friend : "haha"
You : "FUCK ME SIDEWAYS"
by IThinkILoveMyCrushXD December 11, 2016
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When something doesn't go as planned
Dude 1: bro my parents said you can't come over
Dude 2: oh fuck me sideways
by StonerDickle April 21, 2019
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being royality screw over. A term used to express an extremely unfortuante situation.
"Shit I think your girlfriend's pregnant"

"Well Fuck me sdeways!"
by MsTr-Z May 15, 2005
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Used when:
a) One is in a difficult situation.
b) Has heard something unbelieveable or shocking.
c) Has hurt themselves.

An extended Australian version: "Fuck me sideways with a Yabbi Pump!" (Yabbi Pump: Suction device used to pump Yabbis from the sand)
Examples:
a) "Fuck me sideways, wrong hole!"
b) "I just won a million dollars!" "Well fuck me sideways!"
c) (*Slams toe into wall*) "Fuck me sideways that hurt!"

"I just rooted a Kangaroo!" "Fuck me sideways with a Yabbi Pump!"
by fun_afta_dark January 14, 2006
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an expression used in times of worry, stress, disgust, shock and happiness. one may use this phrase in a certain situation, such as when a sheep bites you or a man in a green lycra suit does the cha cha slide on your roof.
"slideeeee, to the left, take it back there yo"

"fuck me sideways what the harl"
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Its when your fucked big time.
Ryan Ryenolds in blade trinity after seeing the 2 rotweiler vampire fucks. goes ''fuck me sideways''
by Sobykicksass February 28, 2010
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An expression of shock or surprise at a given situation
Fuck me sideways, its cold outside today
by Montespan July 12, 2011
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