🏷 Most Popular Boss Videos

Indoor Picnic
15.9K • Apr 4, 2024
Indoor Picnic
Lilly Bell, Victoria Voxxx
She Needs I.T. Bad
12.7K • Apr 22, 2022
She Needs I.T. Bad
Anna Claire Clouds, Penelope Kay
True Lesbian – Show Me Your Room
12.3K • Mar 16, 2020
True Lesbian – Show Me Your Room
Angela White, Jay Taylor
Lady Boss: Performance Reviews
11.3K • May 1, 2022
Lady Boss: Performance Reviews
April Olsen, Kimmy Kimm, Lilly Bell, Vicki Chase
Lady Boss: New Boss Goss
10.6K • Nov 20, 2022
Lady Boss: New Boss Goss
Kenzie Taylor, Spencer Bradley, Victoria Voxxx
Employee Intervention
10K • Aug 13, 2023
Employee Intervention
Bridgette B, Katrina Colt, Lulu Chu
Lady Boss: Personal Package
9.7K • Aug 8, 2024
Lady Boss: Personal Package
Avery Black, Helena Locke
Cougariffic: What Would Your Parents Think??
9.5K • Feb 3, 2022
Cougariffic: What Would Your Parents Think??
Lyra Lockhart, Silvia Saige
Personal Assistant’s Personal Dilemma
9.4K • Sep 8, 2024
Personal Assistant’s Personal Dilemma
Gal Ritchie, Little Puck
Clean Up This Mess!
9.1K • Sep 18, 2025
Clean Up This Mess!
Kimmy Kimm, Little Puck, Sheena Ryder
Lady Boss: From Secretary To Mistress
8.9K • Jan 30, 2020
Lady Boss: From Secretary To Mistress
Casey Calvert, Chanel Preston
Lucky Penny
8.5K • Sep 5, 2022
Lucky Penny
Kenna James, Madi Collins
Showcase: Katie Morgan
8.2K • Oct 5, 2019
Showcase: Katie Morgan
Karla Kush, Katie Morgan
Seeing Red: Office Hazing
8K • Oct 24, 2019
Seeing Red: Office Hazing
Lauren Phillips, Sabina Rouge
Obsessed Assistant
7.8K • Mar 28, 2021
Obsessed Assistant
Jessica Ryan, Laney Grey
Secretary Day
7.8K • Jul 9, 2019
Secretary Day
Abby Cross, Ryan Ryans
Rival Interns
7.6K • Mar 20, 2020
Rival Interns
Jade Nile, Karlee Grey, Sovereign Syre
Role Models: Dress For Success
7.6K • Feb 20, 2020
Role Models: Dress For Success
Aidra Fox, Dee Williams
The Incompetent Assistant
7.5K • Oct 6, 2019
The Incompetent Assistant
Kendra James, Mackenzie Moss
Interrupted Anniversary
7.4K • Dec 27, 2019
Interrupted Anniversary
Alina Lopez, Shyla Jennings
Strap-On Stories: Strap Trap
7.3K • Aug 12, 2019
Strap-On Stories: Strap Trap
Angela White, Karlee Grey, Maddy O'Reilly
Lady Boss: Boom or Bust
7.3K • Aug 15, 2019
Lady Boss: Boom or Bust
Chanel Preston, Sydney Cole
Lesbian News Anchors
5.8K • Sep 5, 2019
Lesbian News Anchors
Natasha Nice, Whitney Wright
Dream Pairings: Surviving The Alters
5.7K • Aug 4, 2019
Dream Pairings: Surviving The Alters
Adria Rae, Chanel Preston, Penny Pax
Showcase: Gina Valentina
5.7K • Sep 20, 2019
Showcase: Gina Valentina
Eliza Ibarra, Gina Valentina
Lady Boss: Company Policy
5.2K • Sep 5, 2019
Lady Boss: Company Policy
April O'Neil, Jade Baker, Victoria Voxxx
How Lesbians Think
5.1K • Mar 6, 2020
How Lesbians Think
Jade Nile, Sovereign Syre
The Interview
4.9K • Jul 16, 2019
The Interview
Carter Cruise, Chanell Heart
Squirting Stories Volume Two: Mopping Up
4.9K • Jul 19, 2019
Squirting Stories Volume Two: Mopping Up
Cadence Lux, Maddy O'Reilly
Extradition: Part One
4.9K • Jul 13, 2019
Extradition: Part One
Adriana Sephora, Kat Dior, Luna Star
Showcase: Jane Wilde
4.7K • Sep 26, 2019
Showcase: Jane Wilde
Jane Wilde, Paige Owens
Boss’s Bratty Daughter
4.7K • Sep 24, 2019
Boss’s Bratty Daughter
Abigail Mac, Casey Calvert
Lady Boss: The Research Assistant
4.6K • Aug 14, 2019
Lady Boss: The Research Assistant
Angela White, Whitney Wright
Lady Boss: The IT Nerd
4.5K • Sep 4, 2019
Lady Boss: The IT Nerd
Alison Rey, Gina Valentina
Working Late
4.5K • Sep 10, 2019
Working Late
Eliza Ibarra, Whitney Wright
Lady Boss: Orientation
4.5K • Jul 30, 2019
Lady Boss: Orientation
Adriana Chechik, Georgia Jones, Penny Pax
Undercover Pleasure – Part One: The Prototype
4.4K • Aug 17, 2019
Undercover Pleasure – Part One: The Prototype
Maddy O'Reilly, Nicole Aniston
Showcases: Brandi Love
4.4K • Aug 17, 2019
Showcases: Brandi Love
Brandi Love, Jenna Sativa, Nicole Aniston
Lady Boss: Lesbian Interview
4.3K • Sep 3, 2019
Lady Boss: Lesbian Interview
Charlotte Stokely, Elsa Jean
Girlsway Newest Editor
4.3K • Jul 25, 2019
Girlsway Newest Editor
Angela White, Kimmy Granger
Lady Boss: Dress Code
4.2K • Jul 31, 2019
Lady Boss: Dress Code
April O'Neil, Jenna Sativa
Office Mediation
4.1K • Sep 20, 2019
Office Mediation
Abigail Mac, Lindsey Cruz, Sinn Sage
Extradition: Part Two
4.1K • Jul 14, 2019
Extradition: Part Two
Abella Danger, Luna Star
You’re Fired
4K • Aug 12, 2019
You’re Fired
Abigail Mac, Uma Jolie
Lady Boss: Caught at the Office
4K • Aug 16, 2019
Lady Boss: Caught at the Office
Karlee Grey, Penny Pax, Sinn Sage
Dream Pairings: Mrs & Mrs Smith
3.9K • Aug 1, 2019
Dream Pairings: Mrs & Mrs Smith
April O'Neil, Georgia Jones, Kristen Scott
Too Hot for Teacher: Birthday Surprise
3.8K • Sep 10, 2019
Too Hot for Teacher: Birthday Surprise
Aidra Fox, Jill Kassidy
Lady Boss: Prove Yourself
3.7K • Jul 30, 2019
Lady Boss: Prove Yourself
Darcie Dolce, Penny Pax, Vanessa Veracruz
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