8 XXX : win-win

(Caption) You didnt intend to win the bet anyway [x-post /r/futadomworld]

imgur.com category @whateverisntchosen

“Pull that shaft and see if ya win” (dentol)

gfycat.com category @sickguyintoweirdshit

I lost a contest. Master enjoyed winning.

imgur.com category @palpascal

I didn't do my tasks two days in a row...sir is leaving it up to you guys to pick how I am punished. Top comment wins [F] [M]

imgur.com category @RopeBaby96

His reward for winning

imgur.com category @pepsi_next

So much win here

imgur.com category @nope_nope_yep

Let me check...yeah I win

imgur.com category @[deleted]

My sister has a winning personality.

imgur.com category @SrcPRNLuvr

Denim and flannel is a winning combination

imgur.com category @pepsi_next

Who's winning? The Underbuns

imgur.com category @Wiskoenig

Definitely a win

imgur.com category @Lobo2ffs

Twin Buns Win Tons! Rosa Album!

imgur.com category @-Tsareena-

As voted by the readers of r/SluttyStrangers, the award for Best "Win" of 2016 goes to…

gfycat.com category @pen_fifteen_

My best win evar (VIC with full chat and penis cam)

imgur.com category @noam_chomskys_ta

One of my best 2016 Wins

gfycat.com category @3year-stranger

First Win with the SluttyStrangers Tag (VIC)

gfycat.com category @MYNSFW56

Any of you want to claim this "win"? (xpost from r/biggerthanyouthought)

imgur.com category @pen_fifteen_

First time sharing one of my omegle wins

imgur.com category @jackyculp

I might have to retire from Omegle after not getting the win on this one

gfycat.com category @parttime811

A small album with some WINS and a question about GIFs/Vids

imgur.com category @pm-me-anything-NSFW

Hnnng... my greatest non-win

imgur.com category @omeglegui

My first win i've recorded

gfycat.com category @snowboardbum3

Here we go r/SluttyStrangers fam - it's time to vote for the Best "Win" of 2016!

imgur.com category @pen_fifteen_

As we approach the end of the year, would anyone be interested in voting on the best "win" of 2016? Comment with your thoughts!

imgur.com category @pen_fifteen_

A nice litte win (with sound)

gfycat.com category @ziplo94

My Omegle "Wins" - Part 1 (videos in comments)

gfycat.com category @KenAddams

First Omegle Win

imgur.com category @ImSice

My best win for the evening. This is what I finished to.

imgur.com category @tossaway8679309

Today's Wins

imgur.com category @omegle_strnger

Mileena wins [via /r/popcult]

imgur.com category @chandacenteno

Losing but also winning

gfycat.com category @Okutupus

In it to win it

tumblr.com category @giblefog

22 F, no longer underweight; proud of winning with multiple EDs but unhappy about saggy, unattractive breasts, considering breast lift

imgur.com category @skewedmind

[45M] 210, 5' 9". Best exercises for a 45 year old to shed some pounds? My son bet me if I could lose 20 pounds by Christmas he'd get a haircut. I need to win...can I possibly do this without cutting out beer? How many pounds is realistic?

imgur.com category @[deleted]

I don't know who is winning

gfycat.com category @Gosufree

[FB] A few wins

imgur.com category @jakefratelli

crop top and low jeans is a winning combo

imgur.com category @Canyonerooo

Beauty takes on a big cock and wins

imgur.com category @macduck71

Giusy Buscemi, Miss Italia 2012 after winning her beauty queen title (x-post /r/BeautyQueens)

imgur.com category @[deleted]

Brunette for the win

imgur.com category @toss666666

A few wins

imgur.com category @jakefratelli

We know who is winning at beer pong

imgur.com category @pepsi_next

pre-vacation. guess where I'm going, win a prize!

imgur.com category @opiomorph

His reward for winning

imgur.com category @pepsi_next

Daddy and I love to wrestle. I put up a good fight, but he usually wins.

gfycat.com category @incestmeat

Hairband, For the Win!

gfycat.com category @CityofIs

Time's running out, my raffle and video sale is almost over! ŭ off all videos, and each video = 1 raffle ticket for a chance to win a 10 minute custom [vid]eo. See comments for details. :)

gfycat.com category @pm_your_pokemon_team

I'm having a super special [vid]eo sale and raffle! Each video purchase comes with a free ticket for a chance to win a free 10 minute custom video. Check the comments for details. :)

gfycat.com category @pm_your_pokemon_team

Fit cutie with lots of premades! Check out my raffle and get your own custom video if you win, along with other nice stuff! [vid]

imgur.com category @eliza_cs

[vid] 3 days until my premade video raffle is ending! get a ticket and you can win great stuff, info in comments!

imgur.com category @eliza_cs