milf Videos (118)
My Fucking Sister
This week on MLB Big D's sister passes by to see what he's up too and all sorts of shit goes down. The cardinal rule in pimping dick is always, don't...
The Good, The Black, And The Horny
A Nameless Desperado is forced into a conflict with his rival "The Sheriff", a notorious Milf Hunter of the old West. Confronted with the challenge of...
A Productive Session
Today, Greedy starts his first day at Gambler's Anonymous. And it definitely was a useful session since he managed to get a client from his class. It'...
Gambling Pays Off
Greedy has been spending our money at the casino and as a punishment we've been making him work over time! So, now we've got him fucking Mellanie, and...
Double Duty With Double D Milfs
This week we're exploring the studio with Bugsi again. We're trying to make it bigger then ever, so we've hit up Ms. Monroe Valentino for another "...
Running On Da Milf
To succeed in the business sometimes a man's gotta do what a man's gotta do. So instead of being sit on our asses waiting for a Milf falls from the...
Everything is HARD, On a Diet.
This week we've got the beautiful Isabella Rossa. A rich ass blond MILF with big fucking tits. Watch Jon Jon destroy that pussy and Isabella scream...
Making it Big!
This week we've got Bugsi shooting his music video for "My Swag". As usual, we would rather trade services instead of getting the IRS taxing us on our...
Hellie Wants Dick and Pussy
A great day for Milfs Like It Black. Found out that my mom knows nothing about the business so that means I can keep on living. Thought we'd just...
Paranoid Mandroid
Let's make this quick, 'cause if my mom shows up we might as well be dead. At the same time, we gotta make that money so we operated out of Tactic's...
Return Of The King
Yeah, that's right! The man Sean Michaels has returned to lay it down for Milfs Like It Black. This guy is a living legend; started the game years ago...
Dog Day Afterpoon
We head out to this one client in a fuckin' opulent mansion on the other side of town. Easy day, we thought; pretty routine, right? Wrong. Turns out...
