Jizz

that moment when you realize the boss just got buffed by the channeler you left alive during your run.

darksouls

Just 25 things? [NSFW (It's not porn but your female boss wouldn't be happy about seeing it)]

Naruto

You are on your knees. Good boy. I like to see you know who the boss is around here.

bigdickgirl

Oh boss man, you're going to have your hands full with me this week...

gonewildcurvy

What would you do for that promotion, hmm...? [An entry for the Halloween contest as your naughty boss!]

BBWGW

"If your parents catch you just stare them in the eyes and finish up like a boss" - Matt [NMH1]

TwoBestFriendsPlay

When you die after finishing an intense boss fight and you realize you forgot to save your game

stevenuniverse

What do you think of this angle? And message me your kik user if you wanna boss me around a bit... ?

twinks

Harry, Your the boss !

nsfw_gifs

(Spoiler) If Asriel is was just your normal RPG boss...

Undertale

I didn't know bring your son to work day was just to get my dad's boss some ass.

GayWincest

Sorry, Boss....I know your mouth is watering, but I ran out of sauce....can you lend me any?

TributeMe

trolling your fam like #boss

ComedyCemetery

You know she is fucking her boss when you find cum stained panties in your gf's nicest pair of work pants.

Hotwife, happycuckold

Jiz Lee is your new boss

shorthairchicks

Fluffer for your girls boss.

BabeCock

Emma Outfits - Lunch with Boyfriend, Dinner with Boss and 'you do trust me with your mates whilst you are at the Football?' :) Louise x

3DPorncraft

My White Boss uses, fucks & fills up my Paki Wife, now he wants her and she wants him regularly, whats your take?

wifesharing

You asked your wife to send a picture of what she was wearing to her boss's pool party

Bbwmilf

After an argument your wife stormed out of the house. A few hours later you got a text from her boss

Bbwmilf

My Paki Wife sent me this with a text "Waiting for your White Boss, I'm ovulating, he knows it and want to cover my fertile eggs very badly, I love his white cock and thick Sperms"

wifesharing

Any white man wants to boss around a little submissive asian boy? Make her obey, listen to your orders, and do as told, and break her to full submission.

asianboyswhitecocks, Tgirls, Ladyboys, traps, Sissies, FemBoys

Ivanka looking like your hot boss who calls you in whenever she needs a fuck toy

Politically_NSFW, u_sparetime0, u_Veronika_W

Here is Your New Boss...

thighhighs

[F] you were concerned when you accidentally sent a dick pic to your married boss.

workgonewild

[verification] Meet your new boss...

TributeMe

If you ever wonder if your [f]emale boss is a slut, try walking into her office without knocking;)

workgonewild

I’m Waiting for your instructions Boss, I'll give you my best❤️ [f]

gonewild

When your wife's boss and his client send you pics of her while she's at a business conference with them.

jobuds

Bully: I love bossing your mom around. I remember when she ratted me out for bullying you, now I bully her. I make her wear these ridiculous schoolgirl outfits and then plummet all her holes over and over again.

bangmybully, mommybully

How was lunch with your new boss?

taboocaptions

You received a message from your wife's boss on their business trip.

AsianCuckoldCaptions

PSA: You can choose some boss icons for your bank tags if you type their names in rather than items they drop (RuneLite)

2007scape

Megan Fox is the trophy wife of your asshole boss. You catch her cheating on him and she offers to let you fuck her if you keep quiet. What do you do with this cheating slut?

JerkOffToCelebs

The boss wants to inspect your assets

officelady

Shutting down the office like a BOSS [M]...Enjoy your weekend all!

workgonewild

I like when your big dick boss comes over

cuckoldcaptions, CheatingCaptions

Make this the day you admit your desire to be bossed around by me.

footfetishnation, FootFetish, FeetToesAndSocks, KyliesFeetttPosts

let me boss you around a bit first then I'm all yours?

PetiteGoneWild, RealGirls, slutsofsnapchat

It looks like your wife is no longer interested in what you have to offer. She's much more into her new boss.

MsStealYourGirl, u_pitchardg

Do you like my application picture? Please let me be your bimbo secretary! I will do anything to make you happy, boss ?

bimbofetish, OnlyFans101

LF Mono Source: All sense of reason is going straight out the door "I'm your mommy, remember?" black hair, sitting, handjob, boss, office worker, mother fetish

HentaiSource, HentaiCity

Everytime you see a girl, I want you to imagine them joining your bullies' or boss's harem. Too many impure thoughts will give him quite the selection, and he wont be gentle...

Censoredforbetas

The boss knows how to catch your attention

officelady

I could be your mean boss! ? Behave or else...

girlsinhoods

The boss said it's time for you to learn your place. I'm just here to help

MissLofn, u_BlaBlaBla1913

My boss warned me his daughter was a wild one, but was determined to get her into the business. I just never expected Charli xcx waiting in my hotel room on her first business trip. She made the offer simply "anything your wife won't do." On second though

CelebrityDaughter

Beat the boss and unlock your award ?

CollegeAmateurs

[f] Do u want to cum in your new slut secretary, boss?

GirlswithGlasses, GlassesGoneWild, GlassesNSFW, Keeptheglasseson, Ahegaos, gonewildahegao, Ahegao_IRL, AhegaoGirls, AhegaoBabes, smilers, MouthWideOpen, AwaitingCum, hertonguesout, Lewd, braandpanties, clothedwomen, nsfwoutfits, Innocent18, UnderwearGW, PastelSluts

Would you do this to your annoying boss??

nsfw_gifs, cumsluts, u_mr-satyr, u_nimblybimbly436