Sailboating 

Same concept as a motorboating (where you bury your face between a pair of boobs and vigorously shake your head from side to side) except sailboating is slower so you can take it the view.

I wanted to motorboat the girl, but her bazongas were so nice that I opted to slow down and ended up sailboating her instead.

Sailboating by Lake Partiers May 4, 2021

Sailboating 

The tender act of gently laying one's face against another's breasts. Akin to motorboating, but without the noise of the motorboat. Rather than revving your emotional engine, you're drifting peacefully upon emotional waters.

"After the week I had, all I wanted to do was go sailboating and forget my responsibilities."

Sailboating by dAni5742 April 15, 2025

Sailboatin 

When you talk about someone coming over and talkin to yo dime piece then they do

I was chillin with this bitch and i saw a dude creepin so i started sailboatin and said this nigs gonna come over here and talk to you, and he did.

Sailboatin by young co September 16, 2010