Jizz

My 2006 roommate and I were Bosses. This is our self portrait. (NSFW)

funny

My boss sent out an email to not spend to much on halloween costumes...a fellow coworker replied with this.

funny

My boss just put up a folding screen in our office. Do I have a dirty mind, or...yeah. [NSFW]

pics

My boss came in with his foot looking like this. Bad Poison Ivy maybe? Reaction to a cleaning product?

pics

MFW my boss plays the boss card in an argument

SRSWomen

My former boss at the club

burstingout

My brother's boss showers at their shop every morning before work, so he decided to give his wash cloth a little extra flavor

funny

My boss told me to get this candle out of his car and light it. I don't think he realized how long it had been sitting in the heat. [NSFW]

funny

My very milf boss

randomsexiness

My milf boss

randomsexiness

My boss, staying true to the trade.

funny

My EPIC 3rd boss fight :/

starbound

My hope for Kingdom Hearts 3, even if he is just a bonus boss.

gaming

My boss is an up and coming artist

funny

My boss has only one eye. This is how we do porn. (nsfw)

pics

My boss just wanted "some art" on the wall. This is what we painted in the back.

pics

My boss has 100 pairs of panties

Pantyfetish

This one is for my boss...and for all the bosses out there who want their assistants to suck their cocks deep and good. Happy cumming

TributeMe, PetiteGoneWild

My boss almost lost his finger at work yesterday. NSFW

pics

My boss asked me to post this on reddit. Enjoy!

pics

My 4 year old drew me a heart (slightly NSFW if your boss has a filthy mind)

funny

My boss wife just asked me to run to the store and get her so(m)ething to eat i asked her if she wanted some tube steak she just smiled hope shes on gw :-)

gonewild

Not sure if this fits here, but my boss wanted me to go around the scales when she knows the truck is overloaded and chp already gave me a warning and said they are watching us. They said its not my ticket. Dad confirmed it is. Fuck you, boss.

OSHA

My boss just sent me this. NSFW

funny

My boss put up a new sign at the liquor store.

pics

My car's mileage made me giggle (NSFW if your boss has never owned a calculator)

mildlyinteresting

[GDHH-053]A Miraculous Creampie Threesome With My Big Tits Boss! I Was A Timid And Shy Guy And Now I Had This One In A Million Chance!! We Were On A Business Trip And The Inn Made A Mistake By Placing Me And My 2 Big Tits Bosses In The Same Room Together!

NSFW_Hentai_n_Jav, bestof_gangbangs, NSFW_JAVPorn, japanpornstars, juicyasians, nsfw_Best_Porn_Gif, AsianNSFW

My old boss is a chode

ImGoingToHellForThis

I want to send this to my boss. What would you do if you were my boss?

gonewild

Wish I could smother my boss at work with these and become his boss ;) (PMs open)

Femdom

26[f] Someone told my boss about my reddit account, so here's a pic my boss took

stockings, lingerie, gonewild

[F, 26] Hey! I am spending the weekend away from home. This was supposed to be a very serious office trip. Turned out my boss has hots for me and he follows me on reddit. A lot of you wanted to see my ass. So here is a photo my boss too right now.

IndiansGoneWild, AsiansGoneWild, IndianBabes

My asian milf boss

NSFW_Tributes, cumtributes, jobuds

My boss letting you know where to cum

jobuds

So my daughter received an "anonymous" tribute (it was from my bosse's boss) and now i want to see more things like that, anyone willing to do more? pm me to share kik

NSFW_Tributes

Ordered to work late I receive this picture from my wife(Hayley Atwell) of her, my boss, and her boss with caption "I won't be home tonight. Happy Anniversary"

CelebCucking

Sometimes if I dream about someone, I wake up in their body. Last week my boss’s sexy little wife came to work looking gorgeous. It was only a matter of time before I woke up in her body. What I didn’t expect was to feel my boss’s cum slowly dripping out

bodyswap

My old boss's wife was a real asset to the company

SoFuckable

I send this img my boss! Becose i see how look my. Today i [f]uck him in back office. Do you want video? And what you think aboit my ass how you fuck me? Give my idea for my boss ???

gonewild

My mom swapped our bodies because thought I should walk a mile in her shoes, so to get back at her I went home with her boss who’s been flirting with me all day. Wow red wine makes her horny...

bodyswap

In the middle of the weekend of Youth Days, I see my boss's car arrive at my house and... my boss in a sexy bikini. When she gets out of her car, she says to me "What happens during Youth Days...".

OldAgeRegression

My boss told me only lesbians like tomboys prove him wrong. I'm looking for a partner, follow the instructions on makefastdate.com to contact me!

tomboyNSFW