Jizz

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

funny

It's a win-win I have a hot boy AND he brought Ni No Kuni

gaymers

I like girls in socks too. Win win.

futanari

Cute face and Cute boobies, Win Win

PerfectTits

I love flowers and glitter and hubby loves nail art. Win-win!

feet

Vacation and feeling sexy ? That's a win win i[f] you ask me ;)

RealGirls

Hourglass figure. Big ass. Win, win.

ass

I guess it's a win-win situation

AdviceAnimals, TrollXChromosomes

Great boobs, great pussy. Win-win

nsfw

It's a Win-Win with Twins

Ifyouhadtopickone

It's the classic case of is that dress too short, or did forget her drawers? It's a win - win answer!

nsfw, gor

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

CuteLittleButts

Either way its a win win, but blonde or brunette?

Ifyouhadtopickone

It's a win, win!

Hotwifecaption

[B/S] Working out is a win/win situation for both of us ;) -ELLA

wincest, u_Bad_Porno

Thigh-highs + thigh-high boots is always a win-win

thighdeology

[F] If ALL of you cum in me, we won't know who the father is. Win/win?

TributeMe, gonewild, IndiansGoneWild, AsiansGoneWild

He wanted to browse reddit, I wanted to suck dick. Win win. [Amature, self]

Blowjobs

Seems like a win-win to me!

jobuds

[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

Stop complaining. Your friends are happy and my cum-loving cuckold has more left for him to clean up. Win-win!

cuckoldcaptions, CEIcaptions

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

JizzedToThis, BigTitsSmoothPits

At first I was worried someone would recognize me... Then I realized it's a win-win if they do!

twinks

A win-win

CuckoldPregnancy

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

taboocaptions

Microbikini booty and some tattoos in the same pictures. Win, win!

altgonewild

I like this naked picture of me and I like that you’re looking. Win/win. (F)43

BustyPetite

[M/S] It's a win-win for both of us.

wincest

A win-win situation

cuckoldcaptions

Of course, she was happy when his team won...but somehow, it was a lot more fun when he lost. [relationship] [implied] [win-win]

xxxcaptions, VanillaCaptions

She enjoys performing for you, and you enjoy watching her demonstrate her skills. It's a win-win.

Cuckold

[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

ilovesluts

Long socks make me feel cozy, matching underwear makes me feel sexy. Win win

EdmontonGoneWild

Not really free use pussy's, but cheap enough for a quick fuck. Your mother and sister get used like the bitches they are and your bully gets some cash. It's a win win.

bangmybully

[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

It's a win-win

cuckoldcaptions, Hotwifecaption

Do you like my Feet? Do you like JOI? Then cum to my cute feet while I give you JOI! It's a WIN WIN! My Onlyfans is only $5 right now, and I just posted a 6min JOI with my feet in your face. I never use PPV, so you will immediately unlock TONs of content

u_bluebirdhouse69

It's A Win-Win Situation

HomoSensuality

A win-win for everyone.

taboocaptions

NSFW Found this gem on eBay for a pretty penny. Proceeds when to charity. A win win for everyone!

vinyl

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

rule34

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

taboocaptions

If you breed with me I get bigger boobs. Its a win win for both of us

BreedingMaterial

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

VanillaCaptions

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 believe this was a Win-Win situation ;)

Omeglesex

"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

I'm so glad I found this sub! Just beautiful women and not an 'OF' in sight! Win Win! [52F]

WomenWhoDontSell

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