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from #thread (https://reddit.com/r/SissyCensoredPorn/comments/4s55uz/just_cant_win/) by @little-anon

Guaranteeing her win tomorrow

imgur.com category @pepsi_next

"yea Mr.Win the new intern is kind of distracting to the other employees."

imgur.com category @THROUGHFAILUREIWIN

"Skin to Win" Wet t-shirt shenanigans

gfycat.com category @DS_Lite

Delotta Brown for the win

gfycat.com category @ttrest

An easy win for him. Got her in the full-nelson.

imgur.com category @throneawaycrown

(m) I suggest you let the Wookie win.

imgur.com category @coxinator88

Twins are always win-win: Anna & Lisa Heyse Playmates from German Playboy 02-2012

imgur.com category @Addon207

How to win any argument

gfycat.com category @Niciforka

Please vote for me! Help me win! :)

imgur.com category @Sweet_BunnyXxx

These boobs would win a prize (more pics in comments)

imgur.com category @sarpu3

Low tops for the win

gfycat.com category @dedalus003

Squidward's victory cumshot for the win

gfycat.com category @onenightst