https://jerkwell.com/categories/office-boss/ Sat 24 Oct 2026 21:45:28 +0200 https://jerkwell.com/videos/8260/menage-a-trans-10-aubrey-kate-austin-rex-charlie-forde-charlie-forde-aubrey-kate-austin-rex/
Aubrey Kate invited her coworker Charlie Forde over for a BBQ with her husband Austin Rex. Things got tense when Austin caught Charlie checking out his wife's cock, leading to a playful reveal. Before she could explain, Austin started sucking Aubrey's cock and pulled Charlie in for a wild threesome on devilstgirls. She definitely didn't see that coming. ]]> Fri 09 Oct 2026 21:13:46 +0200 https://jerkwell.com/videos/8260/menage-a-trans-10-aubrey-kate-austin-rex-charlie-forde-charlie-forde-aubrey-kate-austin-rex/ https://jerkwell.com/videos/8249/send-him-to-hentai-hospital-sarah-arabic-juan-loco/
Juan Loco has an embarrassing problem, but sexy Dr. Sarah Arabic assures him he's in good hands. Juan's got a blockage in his penis, so busty Dr. Sarah gloves up and starts with a massage. She moves on to an advanced paizuri titty-fuck technique, and tells Juan not to hold back. Her treatment nearly works, but his condition is more serious than she thought, so she gives it everything she's got... and Juan blasts the office with jizz! She can't let him leave until he's completely drained, so she evaluates him with her mouth and rides his cock, taking load after load. This time when Juan fucks Dr. Sarah's tits, he busts all over them! ]]> Fri 09 Oct 2026 02:41:49 +0200 https://jerkwell.com/videos/8249/send-him-to-hentai-hospital-sarah-arabic-juan-loco/ https://jerkwell.com/videos/8159/submissive-assistant-worked-hard-ryan-reid-vince-karter/
Ryan Reid’s new job as a personal assistant to a no-nonsense businessman is HARD. She lacks experience, and he is working her harder than she’s ever been worked before. Her boss, Vince Karter, sees this as positive; he can mold her into the perfect freaky assistant. Someone just for him! Ryan thinks it’s unusual that her boss is all over her and talking about his dick and stuff, but whatever, she’s getting paid! And she can get used to spanking, crawling, and serving. ]]> Thu 08 Oct 2026 02:08:34 +0200 https://jerkwell.com/videos/8159/submissive-assistant-worked-hard-ryan-reid-vince-karter/ https://jerkwell.com/videos/8235/take-your-step-daughter-to-work-day-cory-chase-kay-kay-madelynn-may/
Madelynn May goes to her mom Cory Chase's office for an internship tryout, but Cory leaves her alone for a bit. That's when Madelynn's girlfriend Kay Kay sneaks in, and they start having sneaky sex. They almost get caught a few times, but when Cory finally walks in on them, she's actually into it. She joins in for a threesome, saying they've got what it takes for the corporate world. It's all part of mommysgirl's fun twist on office life. ]]> Wed 07 Oct 2026 20:57:58 +0200 https://jerkwell.com/videos/8235/take-your-step-daughter-to-work-day-cory-chase-kay-kay-madelynn-may/ https://jerkwell.com/videos/8207/blowing-the-babysitter-millie-morgan-tyler-cruise/
Millie Morgan is the kind of MILF who doesn't mess around. She interviews Tyler Cruise for the babysitter job, and the whole thing ends with her on her knees. No surprises there. The setup is simple, the tension builds fast, and the payoff is exactly what you'd expect from a Blowpass scene. She's in charge, he's getting the real test, and it's all caught on camera. ]]> Wed 07 Oct 2026 06:59:25 +0200 https://jerkwell.com/videos/8207/blowing-the-babysitter-millie-morgan-tyler-cruise/ https://jerkwell.com/videos/8132/how-s-the-view-octavia-red-little-puck/
Octavia Red and Little Puck are coworkers setting up a retirement party. Octavia climbs a ladder to hang decorations, and Little Puck can't help but peek up her skirt. Octavia notices, leans over to give her a better view, and they start making out before getting it on. Girlsway nails the office tension and payoff. ]]> Tue 06 Oct 2026 22:57:47 +0200 https://jerkwell.com/videos/8132/how-s-the-view-octavia-red-little-puck/ https://jerkwell.com/videos/8106/free-use-send-off-ivy-ireland-maddie-wren/
Maddie Wren is giving Ivy Ireland a massage in an All Girl Massage session, but things take a turn when Maddie reveals she's moving away. A coworker walks in, stays, and just goes with it as Maddie's massage gets more erotic. Before long, the three of them are into free-use sex without any awkwardness, like it's just a normal day at work. ]]> Tue 06 Oct 2026 14:36:10 +0200 https://jerkwell.com/videos/8106/free-use-send-off-ivy-ireland-maddie-wren/ https://jerkwell.com/videos/8099/an-unexpected-applicant-kylie-rocket-hime-marie/
Kylie Rocket walks into an interview for a job, and the hiring manager, Hime Marie, recognizes her from a dating app. The girl ghosted her months ago, but after some awkward tension, they end up fucking right there in the office. Girlsway knows how to turn a bad date into a good time. ]]> Tue 06 Oct 2026 11:18:10 +0200 https://jerkwell.com/videos/8099/an-unexpected-applicant-kylie-rocket-hime-marie/ https://jerkwell.com/videos/8022/dick-print-discipline-ana-foxxx-lola-morena/
Ana Foxxx plays a boss who scolds her employee, Lola Morena, for a visible cockprint in her tight slacks. Instead of getting angry, Ana teases Lola, hinting at discipline if she dresses even bolder. Lola returns in a trenchcoat, completely nude underneath, and Ana wastes no time 'disciplining' her right on the desk. The Transfixed series makes it clear this workplace 'correction' gets very hands-on. ]]> Mon 05 Oct 2026 14:40:59 +0200 https://jerkwell.com/videos/8022/dick-print-discipline-ana-foxxx-lola-morena/ https://jerkwell.com/videos/8014/boss-s-free-use-birthday-brittney-kade-cliff-jensen/
Brittney Kade knows how to make her boss Cliff Jensen's birthday special. She drops by his office to wish him a happy birthday and ends up giving him free-use sex right there, with employees walking in and out like it's no big deal. The whole office seems used to this annual tradition, and Cliff gets exactly what he wants. It's a birthday he'll never forget. ]]> Mon 05 Oct 2026 14:35:30 +0200 https://jerkwell.com/videos/8014/boss-s-free-use-birthday-brittney-kade-cliff-jensen/ https://jerkwell.com/videos/8006/lawyer-client-drillage-charlotte-sins-millie-morgan/
Charlotte Sins plays a client whose divorce just got finalized. She meets with her lawyer, Millie Morgan, at home and the flirting in Lez Be Bad's setup turns into 69ing. The professional vibe drops fast once the papers are signed, and they go for it right there in the office. ]]> Mon 05 Oct 2026 14:28:36 +0200 https://jerkwell.com/videos/8006/lawyer-client-drillage-charlotte-sins-millie-morgan/ https://jerkwell.com/videos/8004/getting-behind-at-work-leya-desantis-francis-x/
Leya Desantis feels bad for Francis X after her boss humiliated him in front of the whole office. She gets revenge by letting him fuck her right in the boss's office, giving him the upper hand. The Asshole Fever series delivers this workplace revenge fantasy with a satisfying payoff. ]]> Mon 05 Oct 2026 14:26:25 +0200 https://jerkwell.com/videos/8004/getting-behind-at-work-leya-desantis-francis-x/