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shake the tree 

To masturbate, spank the monkey, ejaculate and evacuate, jack off, jizz, or otherwise relive oneself via excretion of sperm from the bologna pony, especially when one's bologna pony is hairy as Honey Boo Boo's mom's back.

ejaculate and evacuate spank the monkey jizz jack off masturbate bologna pony
I can't wait to go home and shake the tree!
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shake the tree until they all cum out. 

A sex phrase that involves masturbation or sex with a woman.

it means you stroke your dick until all the semen shoots out.
12 year old: I cannot cum, but why?

Sex obsessed person: Well, you gotta shake the tree until they all cum out.

Shake the money tree in a wine cave 

Fancy political fundraisers for rich donors. In 2019 photos surfaced in which Pete Buttigieg, mayor of South Bend, IN was seated with rich donors in a Napa valley wine cave for a fundraising event. During Dec. 2019 debate, Elizabeth Warren attacked Buttigieg for appealing to rich donors instead of grassroots supporters by using this imagery. A few minute later, Andrew Yang stated his campaign reform policy would increase women and minority elected to offices around the country because "they don't have to shake the money tree in a wine cave", gesturing to Buttigieg.
You will have many many more women run for office because they don't have to shake the money tree in a wine cave.

hit the shade tree 

Usually means you're fired from your job.
Joe: Sorry I'm late again, I had a flat tire.
BossMan: Hit the shade tree!!!!!
Joe: "sits under tree"
hit the shade tree by Jojwjwjejej December 27, 2013