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Swimming on your back while having a massive erection.
"Dude, did you see Jenny in her new bikini at the pool?"
"Yeah man, I saw her while I was practicing my backstrokes. She had me Sail Boating."
The act of farting against the scrotum during Anal sex, turning it into a spinnaker sail.
After a delicious taco Tuesday meal, she took me sail boating
Chantal: I thought gentlemen never sail to windward.
Rodriguez: I'm no gentleman, baby.
The act of going from one garage sale to the next, to the next, to the next, and so on and so forth. Taking a day or a weekend or a few hours to desperately search for other people’s junk.
Me and Fred are going garage sailing this weekend you should join us, we’re too broke to go to the store....
What a horny dude would hope dat da hot female skippers of a schooner-tours company would offer.
When booking an outing with a seaside shop offering “sails and cervix” package-tours, one should make sure to ask if their standard price includes having your gorgeous guide spread her legs for you, or if said delightful “extra” actually COSTS “extra”!
While getting a handie from your girlfriend while laying on your back inverted (like being on a decline bench at the gym) and she has you edged to the point of cumming but immediately water boards you and you don't know if you are gonna cum or die.
Last night was amazing. Angie ship sailed me to the point of climax. I didn't think I was gonna survive.
To finger/caress/play with a partner's body while receiving nothing back.
I heard that Tom was going to sail the ocean with Stacy.