Smailing 

The act of ejaculating on a girls' face in the form of a grin.

in the end.. she was smailing

Smailing by Tantif July 6, 2011

smailing

To experience a video game by watching someone else play it, as opposed to playing it directly.

“damn I want to play Half-Life Alyx so much but I’ll never be able to afford a headset”
“have you considered just smailing it”

smailing by Pomi108 November 18, 2025

yard sailing 

A phrase used to describe the art of shopping at large numbers of yard sales, garage sales, and estate sales.

"I can't WAIT to go yard sailing this weekend!"

"Yard sailing is my favorite activity of late."

"There's nothing I would rather do than go yard sailing."

yard sailing by www.babysue.com May 9, 2006

Smiling Bob 

Noun
Pronunciation: Smile-ing Bob

An erect penis in an inappropriate context

Guy 1: Shit, I was smiling bob throughout the entire sermon today in church.
Guy 2: Oh man, me too! I was smiling bob all while watching Barney when I had to babysit last night!

Smiling Bob by psycholilbunny July 9, 2010

sailing with the captain

To drink large quantities of Captain Morgan's Rum, usually with a group, and hopefully to the point of oblivion.

That girl I hooked up with was so fugly that I had to go sailing with the captain before I could bang her.

sailing with the captain by Robb December 24, 2003

One Hundred Million Smiling Little Ones 

Cum, Spoof whatever you people call it...
Potentail babies usually stopped with a latex implement called a condom

One Hundred Million Smiling Little Ones blinking at me from their latex prison...

One Hundred Million Smiling Little Ones by Fucktarded Scarecrow August 1, 2009

Sky Sailing

Sky Sailing is Adam Young's OLD Pre-Owl City project. It consists of mainly laid-back and acoustic songs. It has recently been released to the public. Any Adam Young / Owl City fans should check this out!

Sky Sailing uses NO AUTO-TUNE! It doesn't sound like Owl City. It's much more beautiful.

Me: Oh, I love Adam Young's project, Sky Sailing. Its so relaxing.

Friend: Oh, I prefer his project, Owl City. The auto-tune makes him sound nice.

Friend 2: I think he sounds PERFECT either way!

Sky Sailing by Smile4Music June 21, 2011