when the man is on his side, and the woman is laying next to him on her back with the penis inside the vagina and their legs intertwined.
Oh baby, i love it when you fuck me sideways.
by whatever you want it to be April 20, 2005
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referring to someone who is really screwed. just a bigger emphasis on how fucked they are.

this is far from a good thing, if you couldn't tell by the name.
mother; "we're going to visit your grandparents tomorrow! yay!"
daughter; "fuck me sideways with a chainsaw."
by josie minus the pussycats June 26, 2011
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Used to describe a situation where you are underappreciated. Not given the credit you deserve.

In shock due to utter disrespect.
" man you didnt do to well that time"
"Well fuck me sideways with a lunchbox, i made it to the last level man."

"Finally, I would like to comment on an unlikely topic, my pass coverage ratings. I see that I am a better at man-to-man coverage (31) than zone (21). Fuck me sideways with a lunchbox. Where did these scores even come from?" -- Ethan Albright to John Madden regarding him beong the lowest rated player in madden.
by kws53 April 22, 2011
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to tell someone to hurt themselves, very badly; a curse.
When the ginormous corporation's troll fires you, you can say "go fuck yourself sideways".
by Pinkie_Flamingo November 1, 2010
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An exclamation used when things are completely screwed, or to express surprise at something.
Staff member: Dude, the fryers are on fire.
Manager: Oh fuck me sideways with a spoon!!

Boy: I have herpes.
Girl: Oh fuck me sideways with a spoon!!
Boy: I'll have to from now on ...
by Scutha January 18, 2008
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When being fucked sideways just isn't enough
Doctor: Sorry But you have Herpes
John: Fuck me sideways on toast!
by TMB94squared October 11, 2009
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a phrase used when agitated.

like a more frustrated version of fuck me sideways.
Alec Daugherty: I would date you, but I fear my girlfriend might get mad.

Ashley Gregg: Well fuck me sideways in church!
by braglesnarples May 9, 2010
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