Archive | Anal Play

Cherie DeVille in “The Animal”

From a Custom Video: Cherie DeVille is a snobby vindictive boss who fires the (admittedly creepy crazy) janitor. He returns […]

Nikki Delano & Tia Cyrus, Sister Slaves!

I don’t even know where to start with this one. It’s a Custom Video, and one of the most amazing […]

Jessica Jaymes Broken

From a Custom Video: This is the 5th time I’ve worked with Jessica Jaymes and I swear to GOD she […]

Alex Chance, Abducted Sextoy

From a Custom Video: Alex Chance uses her charm and her big tits to get through life… until a seemingly […]

Marie McCray Pays the Rent

From a Custom Video: Marie McCray is 4 months behind on her rent and Tim knows just how she can […]

Breaking Nicki Hunter

Custom Video continued: I won an auction from some guy named ProVillain and now I have my very own Nicki […]

Amber Rayne, Abducted Attorney

Another Custom Video, but hey, ANY chance to work with Amber I’ll take it! – Amber Rayne thinks she can […]

Holly West, Extended Training

Another repeat-business Custom Video: Holly West is Tim’s captured slave, but she fails to please him so it’s time for […]

Amber Rayne Sextoy

Amber is your well trained pleasure slave, and you will get every ounce of pleasure that she has! First it’s […]

Jessica Jaymes Busted

Jessica Jaymes plays the stuck-up DA, determined to break up Tim’s slave ring. Tim catches her, sticking a gun in […]

Madison Scott Snared

Sexy Supermodel Madison Scott thinks she’s too good for Tim, but he breaks into her apartment and forces her to […]

Amber Rayne’s Straitjacket Lesson

If you’re interested, the premise is a lecherous vocal instructor (that’s me) convinces his cute but gullible student (that’s Amber!) […]

Diana Prince in Training The Boss

Diana Prince thinks she’s been hired to take over the company and fire Tim, but she soon finds out she’s […]

Riley Evans Office Slave

Riley uses her tits to get her way around the office, but all that’s about to change. Tim is working […]