Typically referring to a women of which her posterior is lacking of fat to the point of the bones colliding with ones pelvis when engaging in rear sexual intercourse. This feeling is similar to that of a wheelbarrow getting caught as it is being pushed causing the handles to jab into oneself.
by bigslimer September 12, 2025

When fucking a woman doggystyle, you then grab her ankles, which are positioned on either side of your body, and use them to thrust back and forth deep into her pussy, all while her ass is in the air, her body is slanted downward, and her face in on the ground just like the wheel would be.
This chick thought she was way too good for me and insisted that she'd never ever, under any circumstances, fuck on the first date, yet after only 15 minutes and one 40 oz of Old E, I'm pulling a wheelbarrow on her and I'm seconds from dumping my load!
by HeroH June 11, 2022

An action preformed by two people involved in an especially heinous sexual act, such as being the "gay pair" in a threesome (i.e. two girls , one guy). One of the participants holds the other in a sideways "T" position and walks the route home exposed.
"Dude, the best part is I got them to do a Wheelbarrow of Shame down the sidewalk after the threesome. I rule."
by Chaz McFeeley October 6, 2009

by Harrylong. 1124 May 4, 2021

A position in intercourse among three people, where the person in the middle is giving oral and receiving from behind. The two on either end are suspending the middle person in the air, by their arms and legs.
by DoktorJag March 24, 2024

The sexual position that occurs when your girlfriend or a random girl is in the bathroom puking after having to much to drink. but your still having sex with her in the wheelbarrow position while holding her hair. Thus being a gentleman for holding her hair.
On Saturday, Jessica came over and she had to much to drink. She spent a lot of time in the bathroom puking but her sex drive was still crazy so I performed the Gentleman's Wheelbarrow
by DanAppleLickrTipperOswinNipper April 13, 2020

When you have so much determination, guts and chutzpah, you need a wheelbarrow to transport your balls.
"Everyone told Alex that his case against the government was a sure loser, but thanks to his wheelbarrow balls he went ahead with it anyway. And won."
by gunfreak September 6, 2021
