Recent Boss Videos

Clean Up This Mess!
9.7K • Sep 18, 2025
Clean Up This Mess!
Kimmy Kimm, Little Puck, Sheena Ryder
Personal Assistant’s Personal Dilemma
9.6K • Sep 8, 2024
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Lady Boss: Personal Package
9.9K • Aug 8, 2024
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Avery Black, Helena Locke
Indoor Picnic
16.2K • Apr 4, 2024
Indoor Picnic
Lilly Bell, Victoria Voxxx
Employee Intervention
10.1K • Aug 13, 2023
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Bridgette B, Katrina Colt, Lulu Chu
Lady Boss: New Boss Goss
10.7K • Nov 20, 2022
Lady Boss: New Boss Goss
Kenzie Taylor, Spencer Bradley, Victoria Voxxx
Lucky Penny
8.7K • Sep 5, 2022
Lucky Penny
Kenna James, Madi Collins
Lady Boss: Performance Reviews
11.5K • May 1, 2022
Lady Boss: Performance Reviews
April Olsen, Kimmy Kimm, Lilly Bell, Vicki Chase
She Needs I.T. Bad
12.9K • Apr 22, 2022
She Needs I.T. Bad
Anna Claire Clouds, Penelope Kay
Cougariffic: What Would Your Parents Think??
9.7K • Feb 3, 2022
Cougariffic: What Would Your Parents Think??
Lyra Lockhart, Silvia Saige
Obsessed Assistant
7.9K • Mar 28, 2021
Obsessed Assistant
Jessica Ryan, Laney Grey
Rival Interns
7.8K • Mar 20, 2020
Rival Interns
Jade Nile, Karlee Grey, Sovereign Syre
True Lesbian – Show Me Your Room
12.7K • Mar 16, 2020
True Lesbian – Show Me Your Room
Angela White, Jay Taylor
How Lesbians Think
5.2K • Mar 6, 2020
How Lesbians Think
Jade Nile, Sovereign Syre
Role Models: Dress For Success
7.7K • Feb 20, 2020
Role Models: Dress For Success
Aidra Fox, Dee Williams
Lady Boss: From Secretary To Mistress
9.2K • Jan 30, 2020
Lady Boss: From Secretary To Mistress
Casey Calvert, Chanel Preston
Interrupted Anniversary
7.6K • Dec 27, 2019
Interrupted Anniversary
Alina Lopez, Shyla Jennings
Seeing Red: Office Hazing
8.1K • Oct 24, 2019
Seeing Red: Office Hazing
Lauren Phillips, Sabina Rouge
The Incompetent Assistant
7.6K • Oct 6, 2019
The Incompetent Assistant
Kendra James, Mackenzie Moss
Showcase: Katie Morgan
8.3K • Oct 5, 2019
Showcase: Katie Morgan
Karla Kush, Katie Morgan
Showcase: Jane Wilde
4.9K • Sep 26, 2019
Showcase: Jane Wilde
Jane Wilde, Paige Owens
Boss’s Bratty Daughter
4.9K • Sep 24, 2019
Boss’s Bratty Daughter
Abigail Mac, Casey Calvert
Rough Day, Sweetie?
3K • Sep 24, 2019
Rough Day, Sweetie?
Adriana Chechik, Judy Jolie
Strip Searching The Maid
3.3K • Sep 21, 2019
Strip Searching The Maid
Aali Kali, Aspen Romanoff
Showcase: Gina Valentina
5.9K • Sep 20, 2019
Showcase: Gina Valentina
Eliza Ibarra, Gina Valentina
Office Mediation
4.3K • Sep 20, 2019
Office Mediation
Abigail Mac, Lindsey Cruz, Sinn Sage
Prove It!
3.7K • Sep 17, 2019
Prove It!
Chanell Heart, Veronica Rodriguez
The Princess and the Porn Star
3K • Sep 10, 2019
The Princess and the Porn Star
Kenna James, Vienna Rose
Too Hot for Teacher: Birthday Surprise
4K • Sep 10, 2019
Too Hot for Teacher: Birthday Surprise
Aidra Fox, Jill Kassidy
Working Late
4.6K • Sep 10, 2019
Working Late
Eliza Ibarra, Whitney Wright
Lady Boss: Company Policy
5.3K • Sep 5, 2019
Lady Boss: Company Policy
April O'Neil, Jade Baker, Victoria Voxxx
Lesbian News Anchors
5.9K • Sep 5, 2019
Lesbian News Anchors
Natasha Nice, Whitney Wright
Lady Boss: The IT Nerd
4.7K • Sep 4, 2019
Lady Boss: The IT Nerd
Alison Rey, Gina Valentina
Lady Boss: Lesbian Interview
4.5K • Sep 3, 2019
Lady Boss: Lesbian Interview
Charlotte Stokely, Elsa Jean
The Toll of Control
2.8K • Aug 31, 2019
The Toll of Control
Ivy Wolfe, Kira Noir
While The Boss is Away
3.7K • Aug 23, 2019
While The Boss is Away
Jenna Sativa, Samantha Hayes, Shyla Jennings
Fashion Victim
2.7K • Aug 22, 2019
Fashion Victim
Bree Daniels, Darcie Dolce
A Friend For Dinner
3.3K • Aug 19, 2019
A Friend For Dinner
Dana DeArmond, Jelena Jensen
Undercover Pleasure – Part One: The Prototype
4.5K • Aug 17, 2019
Undercover Pleasure – Part One: The Prototype
Maddy O'Reilly, Nicole Aniston
Showcases: Brandi Love
4.6K • Aug 17, 2019
Showcases: Brandi Love
Brandi Love, Jenna Sativa, Nicole Aniston
Will Work for Pussy
3.9K • Aug 16, 2019
Will Work for Pussy
Natalia Starr, Whitney Wright
Lady Boss: Caught at the Office
4.1K • Aug 16, 2019
Lady Boss: Caught at the Office
Karlee Grey, Penny Pax, Sinn Sage
Lady Boss: Boom or Bust
7.5K • Aug 15, 2019
Lady Boss: Boom or Bust
Chanel Preston, Sydney Cole
Lady Boss: The Research Assistant
4.7K • Aug 14, 2019
Lady Boss: The Research Assistant
Angela White, Whitney Wright
You’re Fired
4.2K • Aug 12, 2019
You’re Fired
Abigail Mac, Uma Jolie
Strap-On Stories: Strap Trap
7.5K • Aug 12, 2019
Strap-On Stories: Strap Trap
Angela White, Karlee Grey, Maddy O'Reilly
Girlsway’s Newest Makeup Artist
3.3K • Aug 11, 2019
Girlsway’s Newest Makeup Artist
Chloe Cherry, Kristina Rose, Riley Reid
The Busted Burglar
3.4K • Aug 9, 2019
The Busted Burglar
Giselle Palmer, Kristen Scott, Lexi Belle
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