Jizz

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

gonewild

Sent this to my girlfriend after a recent "late night" argument. She laughed, so I guess I love her. [very mildly NSFW]

pics

Girlfriend sent me this on her break. I think it has front page potential but she doesn't. What does GW think. Oh and can you guess where she works?

gonewild

Girlfriend broke up with me today. Guess I can go back to my Ex...

pics

Girlfriend dumped [M]e at 4:20 A.m.... Guess it's just Mary and I. She never fails me.

treesgonewild

The girlfriend didn't want to come play video games with me, guess she is missing out :p

dykesgonewild

My girlfriend and I play games with our neighbor all the time, this time he has to guess who was working his balls and who was working his shaft

Bisexy

My girlfriend surprised me with this picture this morning. I wish they would have taken more, but I guess he was too busy fucking her ass to mess with the camera.

wifesharing, Hotwife

EX girlfriend always said I should post here. guess I will now

MassiveCock

My girlfriend rather play with her phone than with me, I guess I'm all yours LBGW

ladybonersgw

Girlfriend broke up with me. I guess I'll share

ladybonersgw

Used the Live Sketch feature in Couple with my girlfriend... Guess which color is who...

LongDistance

Girlfriend broke up with me yesterday, guess she's missing out

ladybonersgw

Girlfriends Big Tits Guess The Size? :D

boobs

Broke up with the girlfriend. Guess I'll just have to take care of myself now

ladybonersgw

Ashley and Gwen excitedly waiting to play "guess which of your girlfriends is sucking your cock". Best part is, everyone wins.

boltedondicks, jobuds, TheJarlsPornBasement

You guessed it, that's his girlfriend in the picture

trashy

Guess who found a girlfriend today!

funny

My girlfriend was working in the backyard of a house where they also shoot adult movies. The director sent her this picture from the dailies. I guess I'm dating a porn star now?

funny, NSFWFunny, TopSexyPosts

My girlfriend's an attention whore for reddit... I guess I am too

ratemycock

My little penis vs my girlfriends toys... I guess that's why I'm not allowed to fuck her

Humiliation, tinydicks

Visiting my girlfriend in a week and got a new toy to show off. Can you guess my favorite color?

dykesgonewild

Girlfriend yet broke up with me.. Guess she's missing out

ratemycock

I guess it's good that she was trying to help him celebrate, but she really has no clue about Jewish culture. [Age Gap] [Ditzy Girlfriend]

xxxcaptions, u_dude_1911

Girlfriend broke up with me before my birthday, guess i'm not getting birthday sex this year.

ladybonersgw

I guess I'm not fucking my girlfriend tonight.

wifesharing, WouldYouFuckMyWife, TinyTits, cheatingwives, PetiteGoneWild, AsianCuckoldCaptions, Cuckold, BBCSluts

She said yes! Guess who has the cutest girlfriend ever <3

dykesgonewild

(F) I'm your girlfriends nightmare, but your parents favorite. Guess just how dirty I've gone?

gonewild

You had been unsure whether or not begging your Dad to fuck your girlfriend had been a good idea.. I guess you got your answer? [Gf/Father/Cheating]

BrotherCucker

Girlfriend picked this one out for for our bi Grindr foursome the other night... It didn't last long onmy body... I guess that's a good thing?

GayThong

I used a spell to permanently possess my friend's crush. I didn't know who I'd become, so guess my surprise when I became the bitchy girlfriend to the neighborhood bully! I took her over just as she was sexting her man! What have I gotten myself into?!

bodyswap

He just wanted to lay on the beaches all day, but his girlfriend wanted to absorb some local culture. Guess who got their way? [naked]

VanillaCaptions

Your girlfriend keeps teasing your Dad, you know she won't let up until she gets what she wants. Wanna guess what that is? [Gf/Father]

BrotherCucker

Freshly waxed girlfriend. Guess where my cock is going tonight.

ass

Haven't had a girlfriend since October. Guess they're missing out

MassiveCock

Caught my Asian girlfriend using a pregnancy test after she left my dad's room.. I guess he wasn't kidding about showing her who the man of the house really was.

FatherCuck

Your girlfriend was VERY kinky. [naked] [implied exhibitionism, I guess]

VanillaCaptions

Guess mom overheard my girlfriend and me

traps, MonsterGirl, ShinyPorn, NotADildo, SweNsfw, BoredIgnored

"I walked in on my girlfriend having sex with her personal trainer. I guess our relationship wasn't working out..."

TrueFMK

you already guessing im sluttier than your girlfriend arent you

Slut

Guess how many cocks my girlfriend had? :)

NaughtyWives, slutwife, cuck, DegradingHoles

Guess who bought some clothes for "his girlfriend" at H&M today

FemBoys

I want to masturbate looking at your girlfriend. I guess I want to cuck you. [F22]

gonewild

Guess my baby bro has good taste in bitches after all. [Brother's Girlfriend] [Gif]

BrotherCucker

Got my GIRLFRIEND to watch Dynamite and woke up to this... Guess you could say she's ALL ELITE! ?

SCJerk

Your favourite big titty goth girlfriend wants to talk to you about wrestling and pop culture. Chris Jericho knows 1004 submission holds, guess how many I do xo

boobs, naughtychicks, onlynudechicks, SluttyOnlyfans

Just came home to quite a surprise. Apparently my girlfriend decided to transfer her mind into my mother's feet. And not only was my mom okay with it, it turns out it was her idea! So I guess I'm... dating my mom's feet now?

bodyswapfeet