saddling 

The act of having sex on a horse.

Yo, did you see Mark and Jen saddling last night? Poor Clover.

saddling by SaddleMaster September 26, 2013

Saddling the ass 

v. to reason poorly

n. (Ass-saddler) one who reasons poorly.

P1: If we ride the donkey then we will have a great time. We are having a great time, therefore we are riding the donkey.
P2: Stop saddling the ass you ass-saddler.

Saddling the ass by AbbaJoe April 11, 2018

Saddling a dead horse 

Originally meant for when someone put a condom on a limp penis. Currently used for safe rigging practices.

For a safe set, saddling a dead horse is NEVER safe.

Saddling a dead horse by Stagecrewboi777 February 20, 2018

Sack Saddling 

-verb

Triple Penetration. One gent is entering her ass, while a second gent is in her vagina. Then third gent stands over the second gents cock so his sack hangs with a testicle on both sides.

Hey Bro, I love the way it feels when you're Sack Saddling with me.

Sack Saddling by BoronIdentity August 10, 2014

Swaddling

When two lovers fall asleep or cuddle whilst one is penetrating the other. No thrusting is involved.

Originates from the Yahoo Answers question featured on My Brother My Brother and Me (9-12-2011).

It is impossible to perform swaddling for more than 30 seconds. If you can, you might be with the wrong gender or person.

Swaddling by Stocky Gentleman September 12, 2011

Swaddling

A sex act when the man puts his penis into the woman's vagina and then they simply fall asleep for the remainder of the night.
Popularized by Griffin Mcelroy from MyBrotherMyBrotherAndMe

"I had the strangest dream, then I remembered Griffin and I were swaddling last night."

Swaddling by GriffinMcelroyLover September 13, 2011

Swaddling

The act of a man falling a sleep with his dick in a woman's vagina. Swaddling has become a sexual sensation, as well as cultural, largely in, though not limited to, countries on the northern hemisphere.

Twas a swaddling porn.

Swaddling by ThGy007 September 13, 2011