Jizz

Made a deal with the lady interest. I post myself here, she posts herself on gw. We're seeing whose the most attractive (We're each betting the other person will be)

ladybonersgw

My bet for the next part of this scene of the finale. [POSSIBLE SPOILERS (OF THE COMMERCIAL FOR THE FINALE)]

TheLastAirbender

I may not be the the most muscular guy here, but I bet I'm one of the best cuddlers. Would you like to come and see if I'm right? ;)

ladybonersgw

Bet money, this is how the show ends. [NSFW]

TrueDetective

The dance i just did in game 2 of dk vs vg was beautiful!!!! Dem bets be making this intense... What a game

DotA2

Bet you can't find the part of this image I retouched.

pics

My sister bet me I wouldn't last more than 30 seconds - I won that bet, and by the smile on her face, sis did too

DirtyFamilyPhotos

You can bet I'd be the first guy to the office, and the last to leave

ThickChixxx, bigasses

I bet she makes the sexiest noises when she's like this. Too bad she can't scream the safeword loud enough through the ballgag

hentaibondage

My BF lost a bet... Any Bi guys out there willing to jack off online with him? I will get naked in the background and touch myself too, as incentive for helping me make him pay up on his bet!! (F)

gonewild

Bet you can't make it to the end without blowing it ;)

feet

My sister just wanted to bet a pizza that the Patriots would make the Super Bowl. I upped the ante.

IncestGifs, SauceforNSFWads

In poor countries prostitution is the way the Patriarchy mistreats women. In First World countries women are smarter and prostitution is the way women feministly and happily degrade and mistreat themselves to the Patriarchy's amusement. First World is bet

maledom

I bet a friend that the Vikings would win the Super Bowl. Here are the conditions (NSFW)

minnesotavikings

Forgot to lock the door when the cleaner at the hostel came in. Bet he got a boner?

twinks

I bet that peak in the graph to the right was the Mushroom War

adventuretime

We made a bet. The loser strips for the winner. After she stripped down to her thong, I fucked my neighbors wife on his pool table in the basement.

Bbwmilf

We made a bet: the one with the biggest cock would fuck the other's ass... it still hurts (gif)

ShemalesParadise, shemale_gifs

betting on the races!

thanksgravity

I bet the blokes in the pub I could put the bottom of a pint glass on the tip of my cock and carry it from one end of the bar to the other. Do you think I won?

sizecomparison, gonewild, GWAustralia, MassiveCock

"Haha! Bet you won't bet on the Cowboys again! Right, little bro?"

GayWincest

Kinda a dare / lost bet. USF lost to UCF last year (lost bet) so I had to do body paint to support my team this year. Photo is the result. (Also lost same bet this year and result is in comment below)

TruthOrDareMe

[M] Pink panty bet I made a bet with a friend that if BJP wins this election I will wear pink panties for days equal to the upvotes and post a picture on reddit. Can I post such a picture on this subreddit? Let me know your thoughts. P.S. no political deb

IndiansGoneWild, IndianFetish

My wife lost a bet to one of my buddies. She learned to never bet against the St. Louis Blues when a bj is on the line

slutwife

My wife was disappointed that her Bruins didn't win the cup. Now she is fulfilling her bet with our friend. Best bet he ever made. [F32]

slutwife

Curvy bridesmaid definitely stole the show at the wedding. I bet even the groom beat off to her that night.

jobuds

Sorry for the blur but the guy had never used a selfie stick before. I also bet that the camera kept moving on him for some reason. Feel free to guess why

slutwife, GWCouples, couplesgonewild, BehindGonewild

I bet all of Alex Morgan's teammates made her into the team bitch behind the scenes. They keep her tied up in the locker room and take turns with her.

JerkOffToCelebs

Bet you wish you could see the rest ;)

boobs

Bet you wish you could see the rest ;)

funsized

In town just now: @omgdixie goes "I bet you wouldn't flash your tits in the middle of town, in the middle of the day" Me: Boy, you forget who you're dealing with Also me: (From Twitter)

messyjessie58

You're girlfriend bet everything she had at the Casino, at my table. She didn't think she was betting her Body too (RP)

bodyswap

I bet a nice, hard gangbang by all the soldiers in the barracks would've been just the thing to soften Peggy Carter up. (Hayley Atwell)

JerkOffToCelebs

I made a bet with my Italian friend that the US would crush corona before we got to Italy's numbers. I didn't really pay attention to what his terms were... I was so sure of myself. Well now, on the upside, I'm in a beautiful country. On the downside, I'm

bodyswap

I bet the Disney producers play strip poker with the Marvel actresses behind the scenes. [Scarjo, Liz Olsen, Brie Larson, Hayley Atwell].

JerkOffToCelebs, u_xboxbingpornor

I love how Brie Larson has whored herself out to not only being the hottest babe at Marvel but one of the hottest women in the industry. I bet she can suck dick for days on end!

JerkOffToCelebs

Betting for the next half hour... Kik me @RambleOnRos

Cuckbetchallenge

Wow. Signing divorce papers while desperately seeking validation in a Gone Wild subreddit. Taking bets on who initiated this divorce. (Do NOT go looking for the OP, comment on the OP, or post links to the OP. Don't even ask for a link.)

WhereAreAllTheGoodMen

Johnnyb16 had the option before our bet to keep things private, but he went with the risky option and paid the price

Cuckbetchallenge

I had a lot of fun with this one ? I bet you’d have more fun if you saw the rest of the pictures ??? link in the comments ⬇️

onlyfansgirls101

Losing magic bets is just the worst, right? Man, I sure hope I don't lose any magical bets [Anthro Dragon/Dragoness Post-MTF/TGTF] - Watsup

transformation

Bet you guys love this! Sharing the struggle

Turfmanagement

Bets on how soon Boris is going to finish the new illustrations?

Fire_Emblem_R34

Bet you like me doing this on the trail [GIF]

Simulingus

This nigga stuck his head inside of an empty Hawaiian Punch jug and used it for a mask! HAHAHAHA! Yall Louisiana niggas dumb as hell! I bet that shit was cutting the shit out the back of his neck! And he had a OTF chain on! I was the only one in the store

DogHoes

?The sun feels nice, but I bet you'd feel better ?

ModelsGoneMild, adorableporn, GoneMild, Slut, ThickChixxx, curvy, happygirls, LingerieGW, PublicFlashing, chubby, Amateurs_Only, thickwhitegirls, TotalBabes