Jizz

"Should I call your wife and let her know you'll be working it late tonight?"

ass

You have been caught trespassing in my royal woods. Either pay the fine and go to prison, or you will give me pleasure, here in the open field repeatedly and afterward i shall release you. Should i catch you again the punishment will be the same.

nsfw, nsfwcosplay

Should be studying, but I thought this would be more fun. What else do you ladies want to see?

ladybonersgw

You should probably (f)risk me, I might be hiding something (x gwp)

BBWGW, GoneWildPlus

You should't be in here...

ladybonersgw

Should be studying, but decided to take a picture for you instead

ladybonersgw

You should really be checking out this awesome series called "Da Vinci's Demons", and not because the story is so good...

GayDaddiesPics

You should not be in the pool! That is not a bathing suit!

nsfw

Should be working, but I find myself wondering. . . just what exactly do you call that gap between shoe and arch? It looks so snug.

feet

Should you really be wearing those sandals with your ankles looking like that?

CandidFashionPolice

Should be asleep. Browsing reddit sure does get you horny! :D

ladybonersgw

Should be slick and wet from punishing you from behind...

MassiveCock, Hotwife

Should be you instead [f]

gonewild

Be respectful guys, just cause you can find person info doesn't mean you should ruin it (f)or everyone for your own pleasure. Period. <3

gonewild

You should always love what you do. It's just too bad that this can't be my full time job ;)

GoneWildPlusSize

Should be you...

GoneWildPlus, BBWGW, gonewild

Be careful when cleaning your chain (Or why you should never put your fingers where you wouldn't put your dick) NSFW

motorcycles

Should you really be doing that outside?

hentiny

Should be doing aerodynamics homework...maybe you can lift my spirits? Don't be a drag.

ladybonersgw

Should be sleeping, let me know if you can help me get some rest.

MassiveCock

You should already be reading Oglaf, here's a sample

BDSM_Artwork

"You should really be flossing more." [F]

guro

Should be you looking up [f]

altgonewild, LabiaGW

Should be getting ready for a weekend away but I don't feel like riding a plane. Would someone like to ride me instead? Face or cock, I'll let you decide.

ladybonersgw

You find me fucking around like this in dry storage when I should be working.. how do you punish me Che[f]?

gonewild, workgonewild, BigBoobsGW, gwpublic

Being extra doesn't mean you should feel uncom[f]ortable about your body..

phgonewild

Should be studying for finals but instead I'm bending over for you guys ;)

GoneMild

Should be studying for [f]inals but instead I'm bending over for you guys ;)

gonewild

Should be studying for finals but instead I'm bending over for you guys ;)

RealGirls, GonewildPlug

You're Sure We Should Be Recording This? ?

ecchi, AnimeBooty

You should your carrots and be a good girl like me [23f]

gonewild

You see this body? This is a body of a Goddess and should be worshipped justly. I have no time for small talk, empty your wallets or fuck off pig!

findom

Should be working...would rather be here with you. I[m] home alone, who can keep me from getting my work done?

gonewild

Should be studying, but I'[m] hard Hope you are all proud of what you did ?

gonewild, bigonewild

You Already Had Dinner--Now--Which Of These [2] Should Be Dessert...?

PickOne, DolcettKingdom

You think I should be spanked? ? [oc]

assinthong, asstastic, feet, nsfwbuys, sugardaddywebsite, sextrade, Kiksnapsales

You guys should be able to flair your posts now so be sure to do that!!

skindentation, insanporn

You know where your tongue should be. [f]

gonewild, u_andynxpills

You should try to be a little more worried. Do you understand the situation you’re in, human?

IrinaSabetskaya, CosplayLewd, cosplaybabes, rule34, cosplaygirls, Impliednude, TheCoverUp

Should be leaking cum, don’t you think? (21f)

gonewild

You really should be more careful.

keyholdercaptions

Should be looking up at you while you slide on in... oh well. Dm me instead.

GaybrosGoneWild

You're like that even though this should be a punishment

HelplessHentai

You Americans should be asleep but thought I'd say hi (oc)

Hotchickswithtattoos, Hottestredditors

You've been a naughty boy, now what do you think your punishment should be? [F]

gonewild, slutwife, bigareolas, dykesgonewild

You can tell by my nipples that I should be putting clothes on instead of taking mine o[f]f. Oups!

gonewild, VerticalGifs, nude_snapchat

Should be pretty easy for you to rip this off of me

ftmspunished, FtMPorn

"You should add landscapes to your smut, Cap--" they said "--it will be fun!" they said.

u_cpt_popcorn_official, CptPopcorn

You should really be careful what you ask for...

keyholdercaptions, femdomcaptions

Should be studying but I rather be posting nudes for you ❤️

collegesluts, gonewild

You shouldn't compare yourself against me, you should worship my superior cock and accept that you're a little beta bitch and be happy.

sph

You should get some rest which pillow will you be using tonight. I'm looking for a partner, follow the instructions on datingfindlove.com to contact me!

ShionUtsunomiya

You should turn down the volume, I can’t help being so loud while riding that cock ??‍♀️

LipsThatGrip, u_YourDreamCouple

should be getting ready for a work meeting... but I’m stalling by taking pics [f]or you. let’s make me even more late?

gonewild

Should be petite enough for you (OC)

petite, DadWouldBeProud, 18nsfw, funsized

You should let me be your nurse. I have quite the healing touch

RealGirls

Should be choking on my cock while I drive with one hand in your pocket. Who’s up for this challenge? 22 M seeking subs. You know your place

gayslaves

You should not be allowed to be this hot!

lexiluna, WedgesNSFW

You should always be nice to your waitress. Or she may have to teach you a lesson in manners.

BallBusting

Being outdoors and soaking up the sun is helping me feel better! Thank you for all the caring messages the past few days, that has helped also. I should be back to posting sexy new content soon ??

u_miss_violette_