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Chastity Lynn is one of the hottest, filthiest and toughest girls we have on Sex and Submission! She is brutally manhandled and fucked by James Deen in one of the most sexually charged and intense scenes on the site. Chastity is also bound in tight, inescapable sex positions and mercilessly dominated and fucked in the ass. She later confesses to having the strongest and longest orgasm in her life. In this fantasy role play, the troubled Chastity Lynn is coerced into having hardcore-BDSM sex with her probation officer. This update is a must see!

DJ wrote me a pathetic letter confessing a deep obsession he has for Mistress Lorelei Lee. I couldn't help myself and decided to use it against him for my own pleasure. DJ is allowed to worship Lorelei for the day but he's indebted as an office slave to me for a month. Mistress Lorelei plays DJ so expertly that I was even turned on behind the camera. She uses the entire day for one big tease and denial extravaganza for the ULTIMATE cock tease! You have NEVER seen Mistress Lorelei Lee so sexy and you have never seen her deny a cock quite like this.

One is left thinking if DJ had wished to just keep his mouth shut. Truth is we all know Mistress Lorelei's power controls him and he couldn't help himself. Boot worship, humiliation, CBT, strap-on ass fucking, ass and pussy worship and wicked tease and denial are all included.

Sunshyne and Parker fuck like crazed wolves in their small cop shop office. Their sexual tension has boiled over as they rip each others clothes off and fuck on the desk and against the one way interrogation mirror.
Sunshyne ravages Parker as she flips him over on the desk, fucking his ass and stroking him off. He shoots his own face with an explosive cum shot while Sunshyne fucks him.

And Sunshyne’s one cock releases a pent up cum shot like a torrential down pore!

Welcome MILF star Anjanette Astoria to WhippedAss.com. In this women in prison role play update Anjanette plays the strict and sexy warden while Bobbi Starr is the trouble making lesbian prisoner with her sexy side kick Asphyxia Noir. The two girls come up with a scheme to steal the wardens keys and take her hostage in her own office. Of course the warden has a few secrets of her own and the prisoners make sure to exploit every single one of them. Anjanette has been wanting to shoot for Kink.com for some time to explore her curiousness with punishment and bondage. Anjanette is tougher than nails and gets flogged, clamped, fist fucked, spanked, made to worship feet and strap-on ass fucked.

In this fantasy role play update, Alysa plays an innocent tourist who is captured by the government and accused of being a Russian spy. Two sex crazed officers, Mark Davis and Mick Blue, try to get information out of her through hard sexual punishment. Alysa’s hidden sexual desires are explored in ecstasy as she is brutally fucked in every hole while in bondage. This shoot has great interaction with intense anal sex and bondage!

The girls decided to surprise Kenna for her birthday. FIrst was the cake and presents. Then came the best present of all. A knock at the door and it was a special police officer looking for Kenna. Turned out to be a stripper that wasted no time taking off her panties and licking her pussy. Kirsten, Bree, and Savannah were all about it and decided to keep the festivities going with their own pussy licking. All these cougar milfs and their great sets of titties and tight pussies was great to watch. Taking turns blowing Michael, the girls really got into it when he started to fuck Kenna. Talk about getting your birthday wish granted. Enjoy .
Cast: Kristen Cameron Talk to This Girl Brianna Ray Talk to This Girl Kenna Savannah Rae Michael Devine
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Enter Kenna – MilfNextDoor – Watch all the videos now!

just looking to get a bite to eat. there was a wait so i had to chill at the bar for a bit. a hottie was just drinkin there all by herfelf. i started a conversation with her and realized she was totally down. we ate and then went back to the office. check out the video to see what happens next!
Cast: Chloe Peter Paul
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Enter Chloe – StreetBlowJobs – Watch all the videos now!

So, Jay wanted to check out this classic car at the local dealership. We found Yeni, a sexy car salesperson who was not going to take no for an answer. She had devious ways of making offers no man could refuse. She took Jay to the back office and began negotiations. Jay was not sure if he wanted to spend that much on a car, but Yeni persuaded him to with a hot deal. She put her pussy on the offer and closed the deal. She got naked, shoved the dick in her mouth, and sucked it on her desk. Then, she got pumped on her desk before she bent over the desk and got fucked from behind. The action continued until, the cream busted all over her juicy ass. Done deal.
Cast: Jay Yeni
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Enter Yeni – 8thStreetLatinas – Watch all the videos now!

The plane Brandy works on as an air hostess just landed and security wanted to speak to her privately in the office. The security guard told her they had footage of her stealing liquor and cigarettes. He searched her bag and found bottles of liquor and a carton of cigarettes. He then conducted a strip search and found she was wearing a sexy bikini on top of her big beautiful tits and succulent ass that she also stole from the company. The security guard was about to call the police, when Brandy quickly stopped him. She asked if they could work this out another way. The security guard asked if she could suck him dry and she did. She sucked that cock well and got her pussy pounded on the security desk. The security guard wanted to cream all over her feet and she allowed him.
Cast: Jerry Brandy Aniston
Tags: 1on1 bigtits bikini blowjob cameltoe piercings shaved skinny straight tattoo white

Enter Brandy Aniston – BigTitsBoss – Watch all the videos now!

Shay called Cris to her office just to reprimand him for not being a team player, but when he walked in with his shitty attitude she decided to fire him. He begged for his job and promised to be the exemplary employee that she wanted. Shay did not care for the man tears that Cris was shedding and was about to call security, but Cris made her an offer that changed her mind. He offered to lick her pussy everyday, anytime and anywhere in the office. Shay opened her legs and Cris started his new position as a personal office sex slave.
Cast: Cris Commando Shay Fox
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Enter Shay Fox – BigTitsBoss – Watch all the videos now!

I was not feeling so good when my company sent a person to ask me questions about how I spend company money on certain clients. I am just glad she was a smoking hottie. It made the audit a little bit more pleasant. She said she was some certified CPA and the numbers do not lie. She got upset and told me she was going to write a bad report on me which would cause me to lose my job. Before she stormed out of my office, I asked if I could do anything for her, so she would not write me up. She stood there and thought for a second. I was not expecting what she said next at all. She got hooked on this power tripped and demanded I showed her my cock. Since she was so fucking sexy I did not think twice. She grabbed my cock and told me she wanted to cum. My day at the office turned around real quick. Her body was perfect. I made her cum a couple of times just make sure she wrote a good report. She was so caught up in the moment she swallowed my load I blasted into her mouth. I am going to spend more money, so she can cum ask me more questions.
Cast: Ramon Kortney Kane
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Enter Kortney Kane – BigTitsBoss – Watch all the videos now!

It was another day at the job, answering the phone for Manuel. His boss, Nika came back from lunch and she was looking very sexy in that mini skirt, tight blouse, stockings and high heels. Her huge tits were almost popping out of that tight blouse. She went back to her office and called her friend for some phone sex. As she was talking to her friend on the phone, she starting playing with her sweet pussy and pulled out those giant tits. Her legs were spread open, with her colossal cans out, as she was fingering her twat, when Manuel walked in. He asked to be excused to the restroom and he quickly escaped the awkward moment. As he was in the restroom, at the urinal, Nika came in and forced him against the wall. She swiftly went down and started deep throating his cock and titty fucking him with those enormous tits. Then, she dragged him back to the office and made him eat her delicious pussy in order to keep his job. Then, he got full permission to fuck that hot pussy. He bent her over the desk and pounded that pussy as her giant jugs bounced around. She got banged all over her office and got plastered with man juice all over her face.
Cast: Manuel Ferrara Nika Noir
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Enter Nika Noir – BigTitsBoss – Watch all the videos now!

My goodness…Lisa had massive boobs..So big her shirt was almost ripping apart..And with that sexy face to match one cant deny this was one sexy boss..And with my boy bringing her fruits he was sure to fuck..A sexual fantasy explored.Fucking an executive boss on the the executive chair..He might just get lucky and get a little call from the boss herself and drop the fruits for some more office extasy..
Cast: Johnny Sins Lisa Lipps
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Enter Lisa Lipps – BigTitsBoss – Watch all the videos now!

Carolyn had called Johnny into her office to go over some reports he had to finish. He stayed past Five and everything. Upon reviewing his work, Carolyn found it unacceptable. On top of that Johnny was staring at her tits. Her great natural big round tits. She noticed. He got in trouble. The punishment was to lick her pussy and not to talk back. Amazing footage of what NOT to do at work. Tons of blowjob action as Carolyn titty fucked herself with the cock. Johnny even revealed his fantasy of fucking Carolyn on her desk. Made that happen too. Amazing sex scene here. Enjoy it.
Cast: Carolyn Reese Johnny Sins
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Enter Carolyn Reese – BigTitsBoss – Watch all the videos now!

It was another day at the office when my sexy, voluptuous boss, Sarah, called me into her office for some assistance. It seemed she could not get the copying machine to work and needed some help. I quickly resolved the problem when I found it was not plugged in. As I was leaving her office, she caught me staring at her huge tits and she decided to let me get a peek for helping her out. Those jugs were so luscious and I could not stop there. She jumped on the table, opened her legs, and made me do my employee duty to eat that sweet pussy. No complaints here, my fantasies had come true. Then, my boss got on her knees and served me. She stuck my cock in between those tasty melons and titty fucked my dick. Then, I banged her hot twat right on her desk. I pumped that juicy ass until she requested for me to cream all over those succulent tits. After she was done with me, she sent me back to work.
Cast: Tony D Sergio Sarah Jessie
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Enter Sarah Jessie – BigTitsBoss – Watch all the videos now!

Nothing gets tolerated less than sexual harrassment in the workplace. So when Nikki called Billy into her office to ask her about some serious allegations, it was nothing to be taken lightly. Billy had nothing to say. Nikki wanted a demo of what went down. So her huge big titties were played with. Nothing like a play by play to paint the picture. This led to her shaved pussy being eaten and her playing with Billy and his big cock. Intense blowjob fun followed by dick stiffening fucking. I would love to be an employee at this office. Nikki rode the dick and let her bubble butt ass bounce all up and down. Amazing. Good stuff here. Enjoy.
Cast: Nikki Benz Billy Glide
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Enter Nikki Benz – BigTitsBoss – Watch all the videos now!

I guess I am a sucker for a girl with an accent. This paticular girl happened to be my superior from our internantional office in Germany. Im guessing she hadnt had any in a while or maybe it was the long flight over…but I could sense the sex in the air when our eyes met. Yet dont ask me what color her eyes were cuz I immediately started staring at her huge perfect breasts. A little jibber jabber here and there and sense of interest from me and she was game to get down. A little pussy licking a little ass licking and then BAM…all out anal action. Including some ass to mouth. It was the best work day of my life.
Cast: Reno Ana Nova
Tags: 1on1 anal asslick bigtits blonde blowjob mature piercings shaved straight tattoo tittyfuck white

Enter Ana Nova – BigTitsBoss – Watch all the videos now!

My sexy ass boss called me into her office to reprimand me for not filling out some papers correctly. While she was giving me instructions on how to do my job i zoned out and she caught me staring at her beautiful caramel tits. I told her she distracts me from my duties so as a solution to the problem she shoved my face on her huge juggs and then told me that if i did not fuck her good that i was going to get fired. Lets just say that i still have a job.
Cast: Rachel Starr Talk to This Girl Johnny Sins
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Enter Rachel Starr – BigTitsBoss – Watch all the videos now!

The mailman made such an impression on me last time…that I secretly sent a package to myself. And since I am not the greedy type I made sure the assistant manager and the secretary were also involved. Besides I needed to make sure he was the real thing and not just a fluke the last time we encountered. I invited the secretary to see if she would agree with the things that go down in my office. At first she was just watching and said that she had a boyfriend and didnt want to participate. I wanted to fire her on the spot. But as time went on she started masturbating and then ended up participating full on. It was one of the best meetings we have had in this office in a while. Group sex at its finest.
Cast: Jerry Trina Michaels Sienna Mikayla
Tags: bigtits blonde blowjob brunette groupsex handjob lesbian lingerie masturbation mature piercings stockings straight tattoo white

Enter Sienna – BigTitsBoss – Watch all the videos now!

Nicole has been at this job for a relatively short period of time when the two guys who are veterans there started harassing her in a sexual manner. As Nicole was coming into the office today, she had her ass smacked by one of the guys in the hall way. Having reached her boiling point she decided to take this matter to the powers higher up. Well come to find out the boss couldnt make them stop either, but she had another plan of her own. She and Nicole were gonna go in there make the guys strip and humiliate them in the process. And that they did, these girls stripped them down butt naked and then made the guys bang the them. If only you were one of these guys huh, keep dreaming! A classic one for your records. Enjoy!
Cast: Jewels Jade Voodoo Xander Corvus Nicole Aniston
Tags: bigass blonde blowjob facial groupsex mature piercings shaved short straight tanlines tattoo white

Enter Jewels Jade – CFNM Secret – Watch all the videos now!

Today Ramon and his friend went into the bathroom on school campus to smoke a little joint when somehow two lady officers came in and busted them. Before you knew it the ladies had them in custody and were pulling up there records to see who these guys really were. To the ladies surprise no records were found and they were gonna have to write hours of paperwork for practically nothing. So the women came up with a plan. They decided to give the guys two options, One go to jail or Two let the ladies have there way with them for an hour or two! You know the guys picked the second option and I bet they were glad they did. This is an update you cannot miss! Definitely one for your records. Enjoy!
Cast: Dana Dearmond Francesca Le Chris Johnson Ramon
Tags: anal asslick bigtits blowjob brunette deepthroat facial groupsex piercings shaved straight tanlines white

Enter Dana Dearmond – CFNM Secret – Watch all the videos now!