Top Definition
The act that happens from "spooning". Sex in the spoon position. Very good for cold climates;where blankets are are a must. Very Intimate; no partner is on top of another.
We went to bed, and I cuddled her like a spoon. Soon enough we were aroused and we fornicated "Sidesaddle".
by Al Higdon December 24, 2005
When a guy's pants are so tight you can see which side the boys are sitting.
Oh wow. Check out Mark's side saddle. Crystal's one lucky girl!
by Djinn November 01, 2006
A method of hitting on an elderly woman, but can appropriately be applied to all ages in equestrian circles. Used correctly, it implies an ambiguous but unequivocally certain sexual act.
-"Hey Donna, did you get a new wheelchair? Maybe we can try it out side saddle later *wink wink*"
by PT four Life December 27, 2009
Leaving a turd beside the seat of the toilet.
He left a side saddle at that bitches house
by kobiek June 06, 2010
When your thong moves to one side in your pants
Dude you have to see what's going on in

my pants. I got a sidesaddle happening.
by mememe6969 December 06, 2014
An awkward or unorthodox method of sitting in a chair due to one's hemmerhoids flaring up.
Adam sits side saddle while typing at work
by Bakar April 25, 2004
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