side-saddler

An effeminate (often homosexual) man.

From the habit of certain women riding a horse not by straddling it, but by riding side-on with legs to one side, in order not to break the bottle neck. Hence, to ride side-saddle, i.e. to be effeminate.

Man: Craig hasn't ever had a girlfriend. I reckon he must be a side-saddler.
Another man: Haven't you heard? He's been riding side-saddle since he was seventeen.

by Tama Boyle February 2, 2007

CT Side Saddle

While hittin' it from the back, subtly plop the hand onto the lower back/upper right butt cheek. As you are reaming her fuck tunnel, slowly insert your thumb into her butthole. Make an inward to outward motion until you are knuckle deep and massage.

CT: "I just executed the CT side saddle."
?: "Knuckle deep?!"
CT: "Knuckle deep!"

by Speedracer19 April 21, 2010

ride side-saddle

1. To be an effeminate (often homosexual) man; hence, side-saddler.
2 a. To engage in effeminate equitation.
2 b. To engage in effeminate sex.

Jeremy isn't really into girls, women, ladies, whatever; he likes to ride side-saddle, if you know what I mean. Eye-ee, he is a gay.

by Tama Boyle January 20, 2007

Side Saddle Typing

Sitting with your legs crossed or un-crossed with your body perpendicular to the keyboard while typing.

Jim was side saddle typing a lust letter to Glenn Beck to hide his small hate boner.

by JWeebs March 3, 2010

side saddle

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 2, 2006

Side Saddle

Leaving a turd beside the seat of the toilet.

He left a side saddle at that bitches house

by kobiek June 6, 2010

Side Saddle

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