Top Boss Videos

Bred by My Boss
5.2K • Sep 20, 2023
Bred by My Boss
Casey Everett, Devin FrancoNext Door Raw
Capo Dei Capi: MrDeepVoice
2.3K • Dec 2, 2025
Capo Dei Capi: MrDeepVoice
MrDeepVoiceASGmax Films
Rivals: Promotion
2.1K • Sep 27, 2023
Rivals: Promotion
Josh Brady, Julian BradyNext Door Originals
Capo Dei Capi: Cosa Nostra
1.8K • Jan 15
Capo Dei Capi: Cosa Nostra
Apolo Adri, MrDeepVoice, Ricky Hard, Trevor Harris, Vincent GreyASGmax Originals
Thick & Creamy
1.8K • Oct 20, 2024
Thick & Creamy
Devin Holt, Seth PetersonHelix Studios
Dirty Workshop
1.6K • Jun 27, 2025
Dirty Workshop
Colt Spence, Johnny Ford, Ryder OwensASGmax Originals
Jessie Montgomery & Matthew James
1.5K • May 5, 2024
Jessie Montgomery & Matthew James
Jessie Montgomery, Matthew JamesBlacks On Boys
The Wedding Crew
1.5K • Nov 19, 2025
The Wedding Crew
Andrew Delta, Roman ToddNext Door Raw
Oopsie – I Spy My Big Boss
1.4K • May 17, 2024
Oopsie – I Spy My Big Boss
Dakota Payne, Jkab Ethan Dale, Zario TravezzAdult Time
Dickstractions
1.3K • Dec 2, 2024
Dickstractions
August Alexander, Vincent O'ReillyExtra Big Dicks
Elite Employee
1.1K • Jun 4, 2025
Elite Employee
Liam Hunt, Nico CoopaNext Door Raw
Off the Clock
1.1K • Jul 30, 2025
Off the Clock
Ty Roderick, Zane KazanNext Door Raw
My Boss’ Secret Sex Dungeon
1K • Jun 22, 2025
My Boss’ Secret Sex Dungeon
Justin DaJock, Taylor ReignNext Door Raw
Assistant Secrets
872 • Apr 27
Assistant Secrets
Dylan Tides, Ty RoderickMen Over 30
At Your Service
859 • Jan 13, 2025
At Your Service
Eddie Patrick, Marco NapoliMen Over 30
The Intern’s ASSignment
646 • May 24, 2025
The Intern’s ASSignment
JC Hunt, Jonathan TylorNext Door Raw
Fuck The Mean Out
403 • Sep 2
Fuck The Mean Out
Josh Brady, Ricky LeeNext Door Raw
Member Fantasies: How To Be A Team Player
301 • Oct 3
Member Fantasies: How To Be A Team Player
Grayson Cole, Noah AsliNext Door Raw