8 XXX : he wins

He bet that the Patriots would win. Now he has to pay up... :)

imgur.com category @IT1990

[HJMO-322] A Husband And Wife Challenge! If The Husband Can Withstand AIKA's Amazing Technique For 20 Minutes He Wins A Cash Prize! If He Cums Then The Wife Gets Creampied! - 1080p HD - H.265

imgur.com category @bamboozlr

[HJMO-296] A Couple Challenge! If The Husband Can Bear 20 Minutes Of Ai Uehara 's Incredible Techniques Without Cumming, They'll Win A Cash Prize! If He Cums Twice, His Wife Has To Have Cuckolding Creampie Sex!! HD - Starring "Ai Uehara"

imgur.com category @PanKing92

[HJMO-320] Couples Take The Challenge! If The Husband Can Withstand Yui Hatano 's Amazing Techniques For 20 Minutes, They Win Cash! If He Cums, His Wife Will Get Fucked And Creampied By Another Man!! SD - Starring "Yui Hatano"

imgur.com category @PanKing92

[HJMO-314] Couples Challenge! If The Husband Can Resist Kurea Hasumi 's Incredible Technique For 20 Minutes He'll Win A Prize! If He Cums, His Wife Will Be Forced To Fuck Another Man And Take His Creampie! HD - Starring "Kurea Hasumi"

imgur.com category @PanKing92

I don't mind daddy wagering me to his golf buddies; I just wish he would win more often.

tumblr.com category @lemauvaisfils

Comparing with my BF, he wins.

imgur.com category @wookieboy92

He Wins

imgur.com category @creative-juices

Being superior is great. Given his superiority, a superior man wouldn't need any superior woman (if she existed), so he only accepts inferior women. So his is like a win-win position: either he feels no desire for a given woman, or she is a worthless piec

tumblr.com category @itispedosthatareNSFW

He wins this standing 69

tumblr.com category @throneawaycrown

He's going for the win

imgur.com category @throneawaycrown

[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]

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

gfycat.com category @incestmeat

This is a Dark Horse <3 he might win

gfycat.com category @keriberry_420

"Whoever wins this fight, gets to fuck the other's wife." you both drunkenly bet downstairs. He really wasnt joking, and he didn't feel like waiting.

gfycat.com category @Nilfgaardian_Leviosa

My bully made a bet with my mom that his dick is bigger than my dad's. If it wasn't, he was going to stop picking on me. If it is, then she has to give him a lap dance. Looks like the alpha wins again. But at least he didn't fuck her, my mom wouldn't go t

gfycat.com category @[deleted]

Heads You Win, Tails He Loses

imgur.com category @CompileEros

Met one of my favorite local guitarist last night and got to party a bit with him. If only he knew what I'd do for him... Also lost my other glasses in such partying... So granny glasses for the win. Would you still cum on them? (f) (image)

imgur.com category @KdoubleDs

I play a game he just can't win - last 20 min and he gets to choose how to cum!

gfycat.com category @velvetveronica