To nail someone 

To have sex with someone.

I really need to nail someone tonight, it's been so long my balls are the size of oranges!

or

Yes! I finally nailed Jane last night!

To nail someone by Saffer77 April 13, 2014

like trying to nail jello to a cat 

A merging of two popular phrases, each meant to reflect attempting something very difficult: “like nailing jello to a tree” and “like herding cats”. This version simply implies, humorously and a bit gruesomely, that one is, in fact, attempting the impossible.

John’s attempt to get this three kids to bed after they each ate a bag of Halloween candy is like trying to nail jello to a cat.

like trying to nail jello to a cat by Brett’s Brain April 23, 2018

Nail me to the cross 

To put a beat down on a woman’s vagina usually happens during missionary

Im so horny i want him to nail me to the cross tonight.

Nail me to the cross by OTAJay December 27, 2020

nail jello to a tree 

the act of attempting something impossible.

Getting my girlfriend to give me head ,is like trying to nail jello to a tree.

nail jello to a tree by wslngy December 2, 2015

I'd rather nail my penis to a burning building 

An expression of extreme disgust over a proposed course of action. First uttered in the movie, "The Fan," by John Leguizamo.

"Baby, let's go antiques shopping this weekend."

"I'd rather nail my penis to a burning building."

I'd rather nail my penis to a burning building by Artie D. May 1, 2006

Nail my feet to the floor 

Nail my feet to the floor... is a statement of intent. A commitment to "stay" when one's response might be to "leave."

(Lyrics by Amie Rankin) I hear the call of an open road, telling me it's time to go, oh please, nail my feet to the floor.

Nail my feet to the floor by AR2018 January 4, 2018

nail Jell-O to a tree 

to do something difficult or impossible, especially when there is no real point in doing so

To eat a spoon full of cinnamon by itself would amount to nailing Jell-O to a tree. (example of nail Jell-O to a tree)

nail Jell-O to a tree by The Return of Light Joker August 25, 2011