Jill Kassidy Updates Her Office Skills With Her Boss

Her boss tests her other skills so she can keep her job

Jill Kassidy padded her resume, but her boss will let it slide if she shows him alternative skills. At Naughty America, Jill is meeting with her boss and hoping not to get fired. The cute blonde is having trouble with software that she claimed to be skilled in. She is certain that she can learn and get her job done, but her boss is not so sure. Will doesn't want her lack of skills to reflect badly on him with his boss as everyone is expected to be good from the get-go. She wants the chance to prove that she can do it, but Will doesn't know if he can take that chance without getting something in return. She offers assurances, but Will tells her, "I'm sure that's not all you have to offer. You have plenty to offer in exchange for my generosity." Her boss gets closer and rubs her shoulders, letting her figure out what kind of deal they can arrange. He offers to teach her himself if she shows him the other skills that she omitted from her resume.

Click here to watch now!

Jill's boss wants a sexy dance and Jill demurely agrees as long as it is kept a secret and she keeps her job. She shows off her lean body in her baby blue lingerie, letting Will fondle his new protegee. She gets into it more and more, enjoying his big hands on her tits and pussy. "You should be at work, but you're doing bad things with your boss," he says. Jill is willing to be punished for being bad and lets him spank her tight ass. Will isn't going to take all of the perks, licking her pussy ardently as she watches intently. Her boss is good with his tongue as well as a computer, and he will have her ready in no time with those skills.

Jill stays on his desk with her legs open so that her boss can plunge inside of her tight pussy. This is the kind of discreet deal that will work out for both of them. Jill loves the way that big dick feels inside of her. They lock eyes and she pleads with him for more as he rubs her clit and fucks her well. Turning her on the corner, she perches and points her toes so she can accept his pencil in her ink well and forget all about her lack of computer skills. Jill and her boss enjoy their office relations with some doggy over the desk before Will just picks his employee up into a reverse stand and carry. She likes being carted around by a man in authority and services him promptly with extra spit on her knees to thank him for the opportunity. Jill's boss knows that she has the right skills with her mouth and that is more important than the skills listed on her resume. She gives him a ride and shows him what else she can do despite the hard wood of the desk under her knees. Squatting is better, so she perches on her tippy toes to sit hard and deep on his big cock. They get so crazy that they almost knock down the hardware they need to do their jobs. Will catches the monitor and turns it as they get comfortable and close all over the desk. Jill isn't afraid to show her boss her true skills when she spins high and goes hard in reverse. She takes quite a drilling up on her feet, getting louder and more exuberant than when she started. Will takes her back in missionary and she begs her boss to keep fucking her until he can cum all over her. After her boss paints her tight body, she tastes it and smiles wondering if he will start teaching her the program now. He decides the lessons can wait and she can take the day off to regroup for tomorrow. Office sex is a good way to make work something to look forward to!

Jill Kassidy looks like a pageant queen but fucks like a bad girl. She starts off demure and coy, but once she heats up, she is all about it. Her BJ is especially nasty and enthusiastic but her legs are strong and sit her on cock nicely, too. Watch her make a deal to keep her job, updating her office fucking skills along the way.

CLICK HERE FOR THE EXCLUSIVE VIDEO!