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His Boss XXX Pics / Clips

When This Insolent Office Worker Accidentally Texts His Boss A Picture Of His Ass,

When This Insolent Office Worker Accidentally Texts His Boss A Picture Of His Ass, He Learns That There Are Consequences For Being Bad. Click Photo To Watch Free Video.

Hairy Construction Worker Bends His Boss Over The Truck And Screws His Ass.

Hairy Construction Worker Bends His Boss Over The Truck And Screws His Ass.

Lasergrey:  Dean Had Come In Early To Start Working On Those Reports. He’D

Lasergrey: Dean Had Come In Early To Start Working On Those Reports. He’D Been Stalling Too Long Now And The Deadline Was Approaching Fast. His Boss, Michael, Would Have His Head If He’D Be Forced Into The Stockholders Meeting Without The Necessary

Dancinsatyr:  Cameron Had Booked A Caribbean Cruise For His Vacation, But Mr. Benson,

Dancinsatyr: Cameron Had Booked A Caribbean Cruise For His Vacation, But Mr. Benson, His Boss Made Alternate Arrangements. The Limo That Picked Cameron Up Belonged To The Pupmaker. By The Time He Realized He Wasn’t Headed To The Ship, He Was A Semi-Consc

Dancinsatyr:  Hank Paid Handsomely To Have The Pupmaker Kidnap His Rival Steve And

Dancinsatyr: Hank Paid Handsomely To Have The Pupmaker Kidnap His Rival Steve And Make Him The Perfect Dogslave. Unfortunately For Hank, His Boss Also Paid A Significant Amount For Some Additional Programming For Steve. By The End Of The Week There Will

Once They Had Put Their Children To Bed, His Wife Invited Him To Unwrap A Very Special

Once They Had Put Their Children To Bed, His Wife Invited Him To Unwrap A Very Special Present. She Told Him It Was Also A Present From His Boss, For Which He Had To Thank Him In The Next Morning.

She Knew That If Her Husband Was Wimp Enough To Let His Boss Take Her Bra Off He

She Knew That If Her Husband Was Wimp Enough To Let His Boss Take Her Bra Off He Was Probably Wimp Enough To Let Him Take Her Knickers Off, But Now She Wanted Much More Than This, She Wanted His Cock In Her Pussy, To Give Her Pussy To Another Man.

Cuckolding-And-Female-Allure:  She Knew That If Her Husband Was Wimp Enough To Let

Cuckolding-And-Female-Allure: She Knew That If Her Husband Was Wimp Enough To Let His Boss Take Her Bra Off He Was Probably Wimp Enough To Let Him Take Her Knickers Off, But Now She Wanted Much More Than This, She Wanted His Cock In Her Pussy, To Give

Doesn’t My Good Hubby Want To Lick His Boss Cum Out Of His Wifey’s Pussy?

Doesn’t My Good Hubby Want To Lick His Boss Cum Out Of His Wifey’s Pussy?

When He Told Her That Her Needs Mattered More Than His Selfish Jealousy And That

When He Told Her That Her Needs Mattered More Than His Selfish Jealousy And That If He Wasn&Amp;Rsquo;T Able To Fulfill Her Sexual Needs And Found His Boss Very Sexy She Was Free To Have Sex With Him, Her Smile Said &Amp;Ldquo;I Knew That You&Amp;Rsquo;D Finally

Cuckolding-And-Female-Allure:  When He Told Her That Her Needs Mattered More Than

Cuckolding-And-Female-Allure: When He Told Her That Her Needs Mattered More Than His Selfish Jealousy And That If He Wasn’t Able To Fulfill Her Sexual Needs And Found His Boss Very Sexy She Was Free To Have Sex With Him, Her Smile Said “I Knew That

Gemmgqsprettysissies:  Jeremy Quickly Redid His Make-Up. At Long Last His Boss Had

Gemmgqsprettysissies: Jeremy Quickly Redid His Make-Up. At Long Last His Boss Had Asked Him Out For A Drink After Work.

Michelle Went To Marcus’ Office To Tell Him To Stop Blocking Her Husband’s Promotion

Michelle Went To Marcus’ Office To Tell Him To Stop Blocking Her Husband’s Promotion Since She Knew He Was The One That Effecting His Boss. She Knew What Kind Of Pervert He Was Before Going His Place But She Had No Other Option. That Day&Amp;Hellip;Marcus

Buffmensean:  The Business Of Barebacking Part 3 Still Reminiscing About His Hot

Buffmensean: The Business Of Barebacking Part 3 Still Reminiscing About His Hot Bareback Fuck With His Boss Dennis West, Jeremy Spreadums Gets A Surprise Visit From Dennis’ Business Partner Reed Jameson. Reed Convinces Jeremy To Give Him The Same Treatme

Contexxxt:  Most Of The Office Just Called Him A Suck Up.  Most Of Them Laughed

Contexxxt: Most Of The Office Just Called Him A Suck Up.  Most Of Them Laughed Behind His Back And Couldn’t Figure Out Why Someone Who Didn’t Drink, Was Always Out At The Bar With His Boss.  It Was Obvious To Everyone That It Was So He Could Work

Tastefullyoffensive:  Guy Re-Enacts Classic Romantic Movie Scenes With His Boss’s

Tastefullyoffensive: Guy Re-Enacts Classic Romantic Movie Scenes With His Boss’s Dog On His Lunch Breaks [Mmsspp/Via]Previously: Classic Movie Quotes Updated For The Digital Age

Contexxxt:  Most Of The Office Just Called Him A Suck Up.  Most Of Them Laughed

Contexxxt: Most Of The Office Just Called Him A Suck Up.  Most Of Them Laughed Behind His Back And Couldn’t Figure Out Why Someone Who Didn’t Drink, Was Always Out At The Bar With His Boss.  It Was Obvious To Everyone That It Was So He Could Work

Twistedthoughtsofmine:  When The Gardener Didn’t Get Paid Once Again… The Closest

Twistedthoughtsofmine: When The Gardener Didn’t Get Paid Once Again… The Closest Thing That He Could Get His Frustration Out Was…His Boss’ Wife.

Michmemoirs:  “You’re Not His Pal. You’re His Boss. This Only Works When They’re

Michmemoirs: “You’re Not His Pal. You’re His Boss. This Only Works When They’re Scared Of You, Remember?”

One Day An Employee Sent A Letter To His Boss To Increase His Salary...

One Day An Employee Sent A Letter To His Boss To Increase His Salary...

Regularguyz:travis Kept His Job Because He Knew How To Service His Boss.

Regularguyz:travis Kept His Job Because He Knew How To Service His Boss.

  Today&Amp;Rsquo;S The 29Th Of September, So That Means It&Amp;Rsquo;S New Release

Today&Amp;Rsquo;S The 29Th Of September, So That Means It&Amp;Rsquo;S New Release Day!  I&Amp;Rsquo;Ve Just Uploaded A Brand New Caption Story Called &Amp;Ldquo;Execution&Amp;Rdquo; Which Follows A Hitman Who, After Witnessing His Boss Assaulting His Girlfriend, Goes

Gemmgqsprettysissies:  Jeremy Didn’t Realise He Was Sucking His Boss’s Cock.

Gemmgqsprettysissies: Jeremy Didn’t Realise He Was Sucking His Boss’s Cock. He’d Soon Be Swallowing Every Drop Of His Semen Too. I Love Watching My Baby Suck Other Men’s Cocks At The Bookstores &Amp;Hellip;

Coinincident:  He’s Just Having Such A Shitty Day His Boss Is An Ass And He Can’t

Coinincident: He’s Just Having Such A Shitty Day His Boss Is An Ass And He Can’t Seem To Get The Girl Of His Dreams And Then All These Fucking Paper Airplanes Are Stuck To Him And Harrassing Him And He Just Looks So Pissed And That Kid Is Like “U

Contexxxt:  His Wife Could Never Make Him Cum That Hard.  His Boss’s Wife However,

Contexxxt: His Wife Could Never Make Him Cum That Hard.  His Boss’s Wife However, Could Do It Ever Single Time.

Coinincident:  He’s Just Having Such A Shitty Day His Boss Is An Ass And He Can’t

Coinincident: He’s Just Having Such A Shitty Day His Boss Is An Ass And He Can’t Seem To Get The Girl Of His Dreams And Then All These Fucking Paper Airplanes Are Stuck To Him And Harrassing Him And He Just Looks So Pissed And That Kid Is Like “U

Overlordzeon:  Mina And Her “Boss Clone”. I’ve Been Listening And Watching

Overlordzeon: Mina And Her “Boss Clone”. I’ve Been Listening And Watching Cvs2 Stuff Because Of Ryu And His Boss Version Same With Iori, Akuma And Rugal. 

Vgjunk:  Mega Man X3, Snes.    Blizzard Buffalo Had The Best Music In His Stage,

Vgjunk: Mega Man X3, Snes. Blizzard Buffalo Had The Best Music In His Stage, But His Boss Fight Was Like Punching A Small Child In Its Inquisitive Face,

Outmanned:  Ron Never Thought That After Graduating From Business School The Ascent

Outmanned: Ron Never Thought That After Graduating From Business School The Ascent Up The Corporate Ladder Would Bring Him Here, On His Hands And Knees, With A Face Full Of Gray Pubes And His Mouth Being Raped Three Times Daily By His Boss, Who Often

Outmanned:  Ron Never Thought That After Graduating From Business School The Ascent

Outmanned: Ron Never Thought That After Graduating From Business School The Ascent Up The Corporate Ladder Would Bring Him Hear, On His Hands And Knees, With A Face Full Of Gray Pubes And His Mouth Being Raped Three Times Daily By His Boss, Who Often

 Fluffywhite Replied To Your Photo: Help I Cant Stop Sorry  Lune Getting Molested

Fluffywhite Replied To Your Photo: Help I Cant Stop Sorry Lune Getting Molested By A&Amp;Hellip; Hahahaha Lune Doesn’t Look Too Happy About This Yea Not Really Happy About His Bosses&Amp;Rsquo; 10 Year Old Kid Grabbing At His Dick

Buttocher: Bonfire Putting Up A Show At His Job. Security Gives Him A Nice Paycheck

Buttocher: Bonfire Putting Up A Show At His Job. Security Gives Him A Nice Paycheck And Comfy Life But, Being A Dragon, He Sometimes Gets A Bit Greedy. Makes Quite A Bit Of Money Since He Is An Exotic Breed. All The Attention Makes His Boss And His Wallet

Npr:  A Marine-Turned-Cop Was Fired After He Did Not Shoot A Man Who Had A Gun. His

Npr: A Marine-Turned-Cop Was Fired After He Did Not Shoot A Man Who Had A Gun. His Marine Training Led Him To Believe There Wasn’t Clear Hostile Intent; His Bosses Say He Risked Other Officers’ Lives.military-Trained Police May Be Less Hasty To Shoot,

Ammachete:  Dad Wanted My Gf And I To Be His Toys For A While As Mom And Sis Fucked

Ammachete: Dad Wanted My Gf And I To Be His Toys For A While As Mom And Sis Fucked His Boss

Tastefullyoffensive:  Guy Re-Enacts Classic Romantic Movie Scenes With His Boss’s

Tastefullyoffensive: Guy Re-Enacts Classic Romantic Movie Scenes With His Boss’s Dog On His Lunch Breaks [Mmsspp/Via]Previously: Classic Movie Quotes Updated For The Digital Age

Tastefullyoffensive:  Guy Re-Enacts Classic Romantic Movie Scenes With His Boss’s

Tastefullyoffensive: Guy Re-Enacts Classic Romantic Movie Scenes With His Boss’s Dog On His Lunch Breaks [Mmsspp/Via]Previously: Classic Movie Quotes Updated For The Digital Age

Nappiesandchains:  Jerry Was Too Shy To Ask His Boss If He Could Use The Bathroom.

Nappiesandchains: Jerry Was Too Shy To Ask His Boss If He Could Use The Bathroom. He Thought He Could Hold Out Till His Shift Ended. Now He Has Been Totally Humiliated By Having An Accident In Front Of All His Coworkers. He Is Going To Have To Wear A

Mansurfer:  French Lads - Diego De La Vega &Amp;Amp; Sunny Blue - Working Man’s

Mansurfer: French Lads - Diego De La Vega &Amp;Amp; Sunny Blue - Working Man’s Fuckslut Hole: Workshop Ass: Buffed And Bronzed Diego De La Vega Is Horned Up In His Overalls In The Workshop, And His Aching Balls Demand Some Deepthroat Action. His Boss,

Bobbysussman:  Toy Shelf: Han Stops At The Millennium Falcon Where Chewbacca Is Welding

Bobbysussman: Toy Shelf: Han Stops At The Millennium Falcon Where Chewbacca Is Welding On A Central Lifter. Chewie Stops His Work And Lifts His Face Shield, Growling An Irritated Greeting To His Boss. Han: “Chewie!” #Starwars (Taken With Instagram)

Trapcellar:  Bobby Found Out His Boss Greg Was Having An Affair With His Wife. As

Trapcellar: Bobby Found Out His Boss Greg Was Having An Affair With His Wife. As Soon As He Confronted Greg, He Got Slapped With A Sexual Harassment Claim, Forcing Bobby To Resign And Sign All Of His Liquid And Solid Assets Over To Greg. Now That Bobby’s

Deancasheadcanons:  Florist!Cas Sort Of Based On This Headcanon Castiel Forgot His

Deancasheadcanons: Florist!Cas Sort Of Based On This Headcanon Castiel Forgot His Umbrella. His Phone Battery Is At 12 Percent, And He’s Been Driving Around Looking For Mrs. Peters’ House For The Past 20 Minutes. His Boss Is Going To Kill Him For

Embracealphamale:  Hotshirtboy:  Wish He Was My Boss  Even Better, Be His Boss.

Embracealphamale: Hotshirtboy: Wish He Was My Boss Even Better, Be His Boss.

Impregfetish:  Everyone In The Company Hated The Quarterly Dinners At The Boss’

Impregfetish: Everyone In The Company Hated The Quarterly Dinners At The Boss’ House. Steve Was The Only One Who Looked Forward To Them. Each Time, Without Fail, His Boss’ Daughter Would Wait Until Everyone Was Busily Drinking And Take Him To A Dark

Biggshot:  Black-Cuntdoll:  Look At Her Pathetic Nigger Husband Sitting In The Corner

Biggshot: Black-Cuntdoll: Look At Her Pathetic Nigger Husband Sitting In The Corner Lol Othello Was A New In Real Estate And He Took His Wife Louise With Him On A Showing. His Boss Had Told Him His Wife Was Very Attractive Black Woman And With Her

Dionnespet:  He Thought He Had Gotten Away With It - The Flash Of The Lacy Bra Under

Dionnespet: He Thought He Had Gotten Away With It - The Flash Of The Lacy Bra Under His Work Suit, But His Boss Had Seen It And Was Now Enjoying A Night Of Staff Training. His Pay Rises Now Depended On The Amount Of Cum He Consumed.

Impregfetish:  Everyone In The Company Hated The Quarterly Dinners At The Boss’

Impregfetish: Everyone In The Company Hated The Quarterly Dinners At The Boss’ House. Steve Was The Only One Who Looked Forward To Them. Each Time, Without Fail, His Boss’ Daughter Would Wait Until Everyone Was Busily Drinking And Take Him To A Dark

Trapcellar:  Bobby Found Out His Boss Greg Was Having An Affair With His Wife. As

Trapcellar: Bobby Found Out His Boss Greg Was Having An Affair With His Wife. As Soon As He Confronted Greg, He Got Slapped With A Sexual Harassment Claim, Forcing Bobby To Resign And Sign All Of His Liquid And Solid Assets Over To Greg. Now That Bobby’s

Biggshot:  Hattie Mai Got The Call From Lamont’s Boss, She Is Going To Be In The

Biggshot: Hattie Mai Got The Call From Lamont’s Boss, She Is Going To Be In The Entertainment Section Of His Boss’s Presentation. She Also Must Be Ready To Serve As The Convention Fuck Whore.

Impregfetish:  Everyone In The Company Hated The Quarterly Dinners At The Boss’

Impregfetish: Everyone In The Company Hated The Quarterly Dinners At The Boss’ House. Steve Was The Only One Who Looked Forward To Them. Each Time, Without Fail, His Boss’ Daughter Would Wait Until Everyone Was Busily Drinking And Take Him To A Dark

Ffistthepup:  Ffist The Pup Showing Off His New Boots That His Boss Bought Him For

Ffistthepup: Ffist The Pup Showing Off His New Boots That His Boss Bought Him For His Birthday.

Squambie:  My Hubby Is So Silly. He Has No Idea That I Just Got Fucked For Hours

Squambie: My Hubby Is So Silly. He Has No Idea That I Just Got Fucked For Hours By His Boss. That Guy Filled Me Up Three Times With His Big Fat Cock. I Wonder If My Hubby Can Taste His Cum.

The-Ejaculatorium:  It Was So Confusing For Tristan… He Knew That This Shouldn’t

The-Ejaculatorium: It Was So Confusing For Tristan… He Knew That This Shouldn’t Be Happening With His Boss From His Fast-Food Job, Yet His Body Was Telling Him Otherwise.  The Inner Conflict Didn’t Get In The Way Of Him Taking The Older Dude’s

Jake2Bb:  Rumors Of The Layoffs Were Getting More Shrill So Tommy Took Matters Into

Jake2Bb: Rumors Of The Layoffs Were Getting More Shrill So Tommy Took Matters Into His Own ‘Hands’ And Decided To Cull His Boss’s Favor To Make Sure His Wife And Kids Were Not Affected. A Little Nervy, A Little Pervy. Follow At Www.jake2Bb.tumblr.com

Jake2Bb:  Rumors Of The Layoffs Were Getting More Shrill So Tommy Took Matters Into

Jake2Bb: Rumors Of The Layoffs Were Getting More Shrill So Tommy Took Matters Into His Own ‘Hands’ And Decided To Cull His Boss’s Favor To Make Sure His Wife And Kids Were Not Affected. A Little Nervy, A Little Pervy. Follow At Www.jake2Bb.tumblr.com

Loudchill:wolves Are Proud Creatures And This One Didn’t Take It Too Well When

Loudchill:wolves Are Proud Creatures And This One Didn’t Take It Too Well When He Got Fired. So On His Last Day He Drank Plenty Of Coffee, Waited For His Boss To Leave For Lunch And Snuck Into His Office. Once Inside He Waltzed Through The Office,

Impregfetish:  Everyone In The Company Hated The Quarterly Dinners At The Boss’

Impregfetish: Everyone In The Company Hated The Quarterly Dinners At The Boss’ House. Steve Was The Only One Who Looked Forward To Them. Each Time, Without Fail, His Boss’ Daughter Would Wait Until Everyone Was Busily Drinking And Take Him To A Dark

Nastyoldman:  Albert Had Been Ordered To Stand In The Corner And Watch As His Boss

Nastyoldman: Albert Had Been Ordered To Stand In The Corner And Watch As His Boss Used His Pretty Wife And Precious Daughters As His Personal Fuck Meat.

Jake2Bb:  Rumors Of The Layoffs Were Getting More Shrill So Tommy Took Matters Into

Jake2Bb: Rumors Of The Layoffs Were Getting More Shrill So Tommy Took Matters Into His Own ‘Hands’ And Decided To Cull His Boss’s Favor To Make Sure His Wife And Kids Were Not Affected. A Little Nervy, A Little Pervy. Follow At Www.jake2Bb.tumblr.com

Charmingfamilyaffair:  Daddy’s Co Worker, Boss And His Boss’ Girlfriend Thought

Charmingfamilyaffair: Daddy’s Co Worker, Boss And His Boss’ Girlfriend Thought It Was Crazy When They Found Out We Have Sex. Until I Pulled Daddy’s Cock Out And Started To Rub My Tits Against It, They Were Horny In No Time. Daddy Even Got A Promotion 

Hometownhorror:  My Friend Jay Recently Decided To Take Out His Boss Who Had Been

Hometownhorror: My Friend Jay Recently Decided To Take Out His Boss Who Had Been A Thorn In His Side For Years. Inspired By His Actions, I Decided To Get Rid Of A Co-Worker Of Mine Named Julia. I Wish I Could Say Something Like She’d Taken My Promotion