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A Canadian Cowboy Hat is when you when you wear some who just gave birth's placenta as a hat.
I did a Canadian Cowboy Hat when my wife gave birth to out first-born.
Sex on a jet ski in cowgirl position while on the ocean
After I rolled her from her starboard side, she rode me in the nautical cowboy till the seals came home
When the time right, but time month is wrong. One must remove the tampon, holster it is as a lasso, and swing it around flinging blood everywhere, while yelling yeehaww ,thus resembling a cowboy lassoing a bull.
Omg Finley, no way you got with that trany last night
Finley: Dude I went bloody cowboy with her/ her all night
One whose eye is known to oogle in the direction of a wayward breast, particularly when displayed on the skype window in the upper corner of a screen.
Look at the glimmer in the trash cowboy's eye. Looks like he's caught a glimpse of some nubile young flesh.
When you think he's going to grab his saddle but he grabs your balls instead
I though we'were going to take the the horses out and Gary went for a cowboy reach around
Uncertain; my guess: slang term to bypass YouTube filters? A red light district? Perhaps a particularly named district or night market?
Title on a YouTube thumbnail: soi cowboy (walkthrough)