Jizz

Wielding her white cock like a boss

Pegging

Sex, like a boss (NSFW ish).

funny

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

beatingwomen

Taking it like a boss (nsfw)

gifs

peeing like a boss[NSFW]

pics

Showing Chest Like A Boss... (Semi-NSFW)

pics

My definition of: 'Like a Boss'

pics

Arsenal's young player Conor Henderson handles a rape assault from a Man U fan like A BOSS!

soccer

Rarity taking it to the face. LIKE A BOSS. artist:Cupcake34

ClopClop

In the check out aisle: Like a boss 2nd in comments

downblouse

My friend and I shared a large cock on vacation. She had trouble riding it, but I took it like a boss.

funny

Irish fan like a boss (Euro 2012) [NSFW]

pics

i am working like a boss, dont you think?

gonewild

Snorting cum like a boss !!!

cumsluts

Sucking that cock like a boss !!!

Blowjobs

Do you wish you could make your wife come like your boss does?

Cuckold

Priorities. (Redditing like a BOSS)

pics

Jenni Lee - stockings....like a boss

stockings

photobombing like a boss

funny

"At least I took that like a boss, man"

facepalm

"Child, you gotta vape like a boss..."

vape_memes

Working it like a Boss

NSFW_GIF

Fapping like a boss [NSFW]

Unexpected

Squirting like a boss...

nsfw_gifs

Her Prize (F)or Taking It Like A Boss

gonewild

Licking the D like a boss

nsfw_gifs

Cheating like a boss

funny

(F)eeling like a boss

GoneMild

Hmmm.. Do I want a longer lasting happy high but a horrible comedown that lasts a week? Or do I wanna feel like a boss but top that feeling up every 10 minutes but feel great the morning after?

cocaine

Doing my reign like a boss

bbwselfies

[KHUX] Sign if you were able to complete the Mission 314 bonus objectives like a boss. If not, share strats here!

KingdomHearts

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

celebJObuds

Cake like a boss

SexyAtHome

Nina Dobrev rocking her bikini body like a boss. What a tall babe!

JerkOffToCelebs

Redditing like a boss on my last day off... :P

u_-AOC-

Rocking That Bikini Like A Boss

Babes4u

[baby violet] like a boss ? (f20)

PremiumSnapchat

Emily lookin like a boss in her glasses...

KneesUpFeetDown

Hope everyone is surviving quarantine like a boss!! 33F - girls, hit me up! ?

QuarantineGoneWild

Daddy fuckin' my throat like a boss!

FemBoys, Shemales, Sissiesinaction, SissyInspiration, SexyShemales, traps, CDporn, sissyplace, BBCsissies, tsexual, u_SissyMikahDoll, sissydressing, BimboSissyDolls, SissyHeaven, sexytgirls, StraightToSissy, u_ImSluttyontheInside

Feeling like a boss but also bored on vacation...which girl would join?? Dm me?

chesthairporn, u_funkysurprise, ladybonersgw

Getting it done like a boss! [41f][oc]???

nsfw_gifs, 40plusGoneWild, BBWGW, GoneWildPlus, BBWHardcore

My wife on biz casual Friday like a boss!

Wife, HotMoms, amateur_milfs, cougars_and_milfs_sfw

When I'm Feeling Like A Boss

SensualFemdom

AOC looking like a boss

Politically_NSFW

These heels make me feel like a boss

LanaLatex, pantyhose

Wearin' 'em like a Boss

SexyGirlsInBoots, tightdresses

Finishing the work week off like a boss!

maturemompics, OnlyFansPromotions