Referring to Jhenรฉ 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."
1๐ 1๐
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"
59๐ 10๐
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
54๐ 9๐
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!"
14๐ 1๐
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"
43๐ 7๐
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 Frisbeeยฎ
They wanted to play disc golf but were without a disc so they used a sail rabbit.
Accident involving a sailing yacht.
"You look the same age to me."
"I'M FIVE YEARS OLDER AND IN COLLEGE!!!"
SAILING MISHAP!!!!
46๐ 9๐