Jizz

Handling bitches like a boss. (Found in /r/funny)

beatingwomen

Taking it like a boss (nsfw)

gifs

watching TV like a boss

Tgirls

Tori Black taking it like a Boss

nsfw

reading like a boss

Femdom, smokingfetish

She looks like my boss... I've imagined this so many times...

Pegging

However you like it, Boss!

manlove

{f} Who wants to boss a ragamuffin like me around? ;) (mic)

GoneWildPlus

Dealing with Sharks like a Boss (maybe nsfw)

gifs

Cumberbatch - only 2 1/4 episodes in, I've gone from "okay, I don't get what all the fuss was about" to "oh god, do I get it!" So here is my thank you for fussing until I finally caved and watched. (mild, but NSFW. Unless your boss likes him as much as yo

LadyBoners

Treating You With The Ass, LIKE A BOSS!

curvy

Found this on /dsg/: Bigger images of the achievement trophies of Dark Souls 2. They clearly show what some of the key bosses will look like in the game. I've provided the names of these trophies in the comments section. Needless to say, spoilers ahead.

DarkSouls2

How do you like this, boss?

NSFW_GIF

Fapping like a boss [NSFW]

Unexpected

[SPOILER] The final boss battle be like

splatoon

Since you liked my tits on my boss's desk so much, I figured it needed a piece of ass, too....

workgonewild

I know its been a long week at work and your boss treats you like shit at work, so I want you to take all that anger, (f)rustration, and tension and use it to abuse me sexually until you have reasserted your dominance by using my body.

gonewild

Christina Hendricks: Restraining those monster tits and looking like a boss. Let's help her unzip.

celebJObuds

Khloe Kardashian can fill out a fucking pair of jeans like a boss. I still suspect that Khloe can ride cock harder and longer than any woman in that entire slutty family....she's always had to prove herself, and I bet her craving for dick is insatiable;)

JerkOffToCelebs

My lovely 23yo hotwife sent me selfie from her work. I know that in fact she fucked by her boss in this outfit and I like it.

hotwife_cuckold, wifesharing, WouldYouFuckMyWife, HotWifeLifestyle, AsiansGoneWild

The Boss looks like she's begging for cock ?

WrestleFap

Do you think her boss will like her outfit for work today?

WouldYouFuckMyWife, wifesharing, HotWifeLifestyle

Sexy secretary wants you to punish her like a strict boss [KIK][GFE]

sexting

My White Boss treats my Paki Wife like his Bitch - She loves his white cock and sperms

wifesharing

I want to suck my boss’s cock like a good little slut (19F)

gonewild

Josh likes his dad's boss.

taboocaptions

Bathing like a boss

FitNakedGirls

Last night's MFM has the wife feeling like a boss... Anyone want a private consultation? [F29]

gonewild, slutwife, wifesharing, bestofwives

Her boss likes to keep her late

CheatingCaptions

The day I was supposed to retire, my boss offered me Karin's body, the young and stupid woman who was supposed to take my place. "You're the best secretary I ever had. I can't let you go like that." So, here I am : young again and more beautiful than I ev

bodyswap

As a reward for your hard work, your boss Brooklyn Decker greets you like this and says you can use her body however you want for an hour. What do you do?

JerkOffToCelebs

I like when your big dick boss comes over

cuckoldcaptions, CheatingCaptions

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

your wifes boss, likes to fuck her on his office desk

Censoredforbetas, u_elizabethsissybottom

(Request) Her boss likes her tits

Hotwifecaption

[F]elt like getting a little naughty at work.. what would you do if you were my boss and walked in on me ? ???

petite, booty_queens, rearpussy

Please don't let my boss know I'm taking pics like this at work

GoneWildTrans

Elsa best boss Aromasensei Frozen. Like me ? I'm waiting for you on makefastdate.com

NewAdultComics

The name says its al, this is The Boss. It's strong and girthy and makes you pound your chest with your fist. If you don't like the strong rye then this isn't for you. This is a great drink for an all night crazy sexcapade.

BoobsAndBooze

When my boss leaves I like to take pics of myself in our boudoir studio

altgonewild, BellyButtons, boobs, girlswithtattoos, gothsluts, holdthemoan, Hotchickswithtattoos

40 year old Christina Aguilera looking like a busty boss

JerkOffToCelebs

He sucks like a boss! New videos dropping tomorrow on OnlyFans! Link im my Bio

u_beefyginge, AlphaMalePorn, broslikeus, GaybrosGoneWild, gaygingers, gayporn, gingerdudes, FantaPantsFags

Wished my boss came to work like this

Men2Men

Nothing says boss like a woman in heels.

XXXHeels

?? Horny Call Centre Girl Likes to Suck her Boss & gets a Ride in Return gift ??

DesiIndo, indiannudee, Desinude_daily, xxxycelebs, indianEXnude, Vilen_Collection, Lust_maal, DesiBoners_2, Lustdesii, HotDesiSluts, Desihub, DesiTeen, DesiXvideo, Tharki_boys, sexydesigirls, UkPakiBeauty, u_weekendkiss27, u_despicablehe3996

Working that dick like a boss

Belladonnaxxx

My last boss looked like Jennifer Love hewitt. I wanted to drop a load on her tits soooo bad!

JerkOffToCelebs

I like it when you show me who’s boss

BreedingMaterial