Jizz

My girlfriend Vagazzled herself....if you can guess what it is you win. if you can't, you still win

gonewild

So, my 87 year old grandfather handed this to me today. Looks like a win/win to me. Slightly nsfw.

funny

You seem to like my smile, I like to smile. It's a win-win.

ladybonersgw

Lost the weight, kept the girls.. win-win!

gonewildcurvy, BigBoobsGonewild

Cute face and Cute boobies, Win Win

PerfectTits

I felt bad using a card that I thought would be an automatic win. It didn't win the round.

cardsagainsthumanity

When the Red Sox win, everyone wins

jockstraps

XXXXXmore a win is a win right?

photoplunder

Great boobs, great pussy. Win-win

nsfw

A win-win situation. [chastity, femdom, anal, rimjob]

keyholdercaptions, xxxcaptions

Cubs win! We all win!

nsfw, boobs, LegalCollegeGirls

Admittedly, I started going to yoga classes for the butts... I stayed because it turns out I actually enjoy yoga. Win/win scenario!

CuteLittleButts

It's a win, win!

Hotwifecaption

Can we call this a win/win? [f]

gonewild

Me and JackSkellingtonLives. He wins length i win width

cockcompare

Seems like a win-win to me!

jobuds

Seems like a win-win to me

BabeCock

[F] [M] I wanted to play, but my boyfriend wanted to take a nap. Win-win!

BDSMGW

Liza from Sunstone comics cosplay: a win-win (explanation in comments)

SFandFslavegirls

When jerking off onto JLaw, don’t worry if you happen to blast all over your buddy’s cock. He can just use it as lube to unload on her too. Win-win. ?

jobuds, celebJObuds

Friend loves going on vacation and I love stroking to her awesome tits in bathing suits. Win/win

JizzedToThis, BigTitsSmoothPits

Galina Dub and pizza> Win,Win!

CuteLittleButts

If you win, I'll (f)lash you in your office. If I win...

gonewild

Dark hair, tan skin and a pretty face! Win, Win!

sexygirls

[M/S] Have fun and guilt her husband. It was a win-win.

taboocaptions

A win-win

CuckoldPregnancy

I'm trying to win the Manyvids Bush of the Year contest on Manyvids, and my success depends on your wallets ;). Tonight - get a session from me for to help me win that crown :)! KIK me to set up a session - allie_sweetxo - link to vote in comments (free v

shamelesslyunshaven

[M/S] Clearly, a win-win scenario

taboocaptions

Gf [24] would like to do another guy, but we would like to arrange a massage first. She starts to massage you in your underwear and we will see where the night goes. Its a win-win situation for you. We are going to travel across USA next week. Pm us with

WouldYouFuckMyWife

A win-win for Josh. He can move back home.

taboocaptions

It's a win-win for both of us. (Incest, Mom/Son)

xxxcaptions

Heads you win, tails you win :-)

cockheadlovers

In AltBoobWorld a toga is a good way of winning a prize at a costume party. Perhaps this style would win prizes in your world too?

AltBoobWorld, OneBoobFlash

[F] Small asian big ass = Win/Win <3 SC: amyleesexy

CuteLittleButts, ass

A Hot Piece Of Ass and a Cuck To Raise Your Baby? Win Win.

AsianCuckoldCaptions, u_CompileEros, CuckoldPregnancy

It's a win-win all around.

taboocaptions

Melissa Wins! Melissa's poll winning pics (x-post from /r/FlarrowPorn)

DCTVFap

[M/S] A win-win

taboocaptions

Making deals with friends is always a win-win. [implied FFM]

VanillaCaptions, xxxcaptions

Slim waist + HUGE booty = Win/win right? <3

pawg, SlimThick

? onlyfans raffle!! ? at 250 subs: 1 person wins a free YEAR, 4 people win free 6 months! [LINK & INFO IN COMMENTS!!]

melstarr, HotOnlyfans, OnlyFans101, onlyfanschicks, onlyfanshottest, OnlyfansXXX, OnlyFansPromotions, onlyfansgirls101

Was playing KL as V1 Sub-Zero and was fighting against this guys Scorpion. I win first round, then he wins second and starts talking all this sh*t calling me a f*ggot. I take third round and t-bag him and he starts saying how he’s gonna “send me offline”

Mortalkombatleaks

A win-win for everyone.

taboocaptions

C'mon dude you gotta admit this is a great plan! I enter your hot mom's body to experience what a pussy feels like and you get to lose your virginity by fucking her body. It's a win-win situation. So what do you say we take our clothes off?

bodyswap

Min min for the win win (LepyPepy) [ARMS]

rule34

It's a win-win for this busty mom.

taboocaptions

Business majors learn to create win-win scenarios. [implied stripping] [office]

VanillaCaptions

Let’s have a race. If I win.. I get to sit on your face! If you win.. I still get to sit on your face!?

Nude_Selfie, fitgirls, collegesluts

This deal sounds like a win-win!

sissycaptions

Your loving Mom knows she's only allowed to use my pool as long as her juicy holes are kept on display for my enjoyment. "It's a win-win situation, son" she told you, "and nothing more than a sign of respect".

IFYM

A win-win

taboocaptions

What are you waiting for? I know what I'm waiting for. YOU!!! With a 3 months free trial on Onlyfans and an extra free gift when you quote Reddit in a dm its a win win!!. Links in comments .

realSindyDay

I covered him, he covered me. I think we'll consider that a win/win. [OC]

cumfetish

Wearing a fur coat without having to murder 101 dalmatians, it's a win-win

AsiansGoneWild, asians_gif

"I love Dubai! Getting 100k a night to be fucked in every perverted way possible - it's win-win for me!" - Anna Faith

CelebNSFWTalk

B[f] likes me to wear see through tops so he got me this one, win-win

gonewild

2nd win this night!! this hot couple helped me finish. This is my first true win ever

Omeglesex

This lady was sure she would win Best Actress at the awards ceremony. I don't think she did win, do you?

AltBoobWorld

Randy Roleplay - Teacher ~~ I really really like to switch the power roles when it comes to classic dynamics like this. Isn't it way sexier to see a man of authority bent over a desk and getting exactly what he wants? And I get an A, win win! ?

u_ThirstyMiss, gentlefemdom, PeggingArt, pegginghentai, FemgazeHentai, u_yaboinothing7

If you win, you get to grab it. If I win... I guess you still get to grab it ;)

BBW_Chubby, BreedingMaterial, ButtsAndBareFeet, chubby, collegesluts, DemEyesDoe, GirlsInRealUniforms, GoneMild, GoneWildSmiles, GlassesGoneWild, GirlswithGlasses