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When your scrotal sack sticks to each side of inner thighsl usually due to long term sitting or swass and when you stand up it resembles the full sails of the Black Pearl.
"Man, I was working in the office all day and when I got up my sail sack had me thinking of my next vacation."
Referring to Jhené Aiko's EP "Sail Out", the phrase means to "Be free, go with the wind, like a sailboat."
"It's really important to sail out when it comes to peace... inner peace especially. You can't help anyone else if you don't have it together yourself."
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easy going, an unbumpy ride into the future.
"I've finally got that out of the way". "Well, now it's smooth sailing from here"
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The term one "African" uses to explain a certain cellular telephone (one caucasian male/female may call "portable") inside ones pocket mostly the front pocket to avoid unneeded disastrous situations in which the device becomes smothered by bottom sweat and bleu cheese dressing (conveniently located in the rear pocket of most levi jeans)
nigga yous gots ta gots yo sail fone (nigga!)
...umm sir you spelled "phone" incorrectly
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The sexual act that involves a small person.
If a man inserts his fully-stiffed penis into small person's anus/vagina, he can start to rotate the small person around his penis, thus imitating the act of turning the sailboard wheel - giving him an unique grinding sensual pleasure.
Rotation can be also invoked by slapping the small person really really hard.
Man and his wife fighting: "You bitch, if you were a midget, I'd slap your ugly face so hard, I would be midget sailing till next Tuesday!"
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a term that means looking for girls/pussies.
looking for wiling girls to have sex.
"Man, It's been a rough week."
"Yes, we should go pussy sailing."
"Indeed"
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A rabbit that has been run over on a desert highway and dryed out so much that you can pick it up and throw it like a Frisbee®
They wanted to play disc golf but were without a disc so they used a sail rabbit.