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The slave master that drove the boat who skipped his ras back out of the West Indies with all his likkle buddy dem.
The Royal family are a bunch of skippers who skipped there ras out of royalty because of there fuckery.
Skipper by FOTB May 30, 2021
I want an ice cream skipper”
Skipper by #thisismydaddddyyyyy November 11, 2022

skipper flipper 

When a woman is bathing or swimming naked and her labia ebbs and flows with the current of the water. Usually occurs in a woman with an above average size labia.
Beth and Tommy decided to go skinny dipping at the lake. They stripped down and entered the cool morning water, wading out until it was up to their waists. From nearby, they heard an old man laughing. They turned and looked real quick and noticed a man on the shore fishing. He said to them, "Holy shit girl, you have some mighty long vagina lips. You got a skipper flipper going on there." Beth screamed, Tommy laughed with man.

skipper boy 

Skipper boy is something you would call someone if they are being a chicken. Like if they refuse to do something like a dare you call them a skipper boy.
Person A: "come get me skipper boy!"

Person B: "No!"
skipper boy by ThineOlConiChi December 17, 2021

Skipper’s Knuckle 

When your ass is being fingered so vigorously and intensely by a partner with fat, sausage fingers that you burst a vessel/hemorrhoid.
I gave Roger a skipper’s knuckle last night.

Skipper Day 

Me and my mates were bored so we decided to make a special day cuz why not - The day is on the 8th of December and its when u can basically do watever u want like kicking boys in the nuts, punching anyone, flooring atleast 2 people, hitting everyone that has a new cut, shouting and being weird and wearing a mask cuz of the corona shit ;)))
'Yo, happy skipper day'

'Wat's that?'
'A special day when i can hit u and be a dumb hoe ;))'
Skipper Day by UrLocalMother;)) December 8, 2020