Archive | Cumshots

Lauren Phillips Seduced and Corrupted

So I admit this is a tad mainstream for this normally fetishy Villain, but hey when Lauren Phillips invites you […]

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 […]

Alyssa Lynn Spreadeagled & Straitjacket Fucked

From a 3-part Custom Video: Alyssa Lynn has been brought to a very special clinic after she was arrested at […]

Kat Dior Sensual Consensual

After a hard day of doing evil, Kat Dior and I decided to lighten things up with a sensual consensual […]

Tia Cyrus and the Training Hood

Yet another custom video from one of my awesome benefactors: Tia Cyrus’s continuing story of sexual slavery, complete with chains, […]

Keisha Grey Spreadeagle Sex

From a 4-part Custom Video featuring Keisha Grey: knocked out with a syringe, stripped, taken to a ‘hospital’ where her […]

Tia Cyrus Trained

Yet another awesome Custom Video featuring the amazing Tia Cyrus: Master is never satisfied with slave Tia’s performance and he […]

Jessica Jaymes in “Master’s Rage”

Four part series from a Custom Video: The continuing story of Slave Jessica Jaymes’s training at the hands of her […]

Tia Cyrus in “Caged”

From a 4-part Custom Video: Tia Cyrus kneels in her cage. She was once a free and powerful woman, now […]

Jessica Jaymes Humiliated

From a 4-part Custom Video: The continuing story of Jessica Jaymes, once powerful District Attorney, now the kept property of […]

Jessica Jaymes Totally Fucked

From a Custom Video: The torments of Jessica Jaymes, once a powerful district attorney, now broken sex slave, continue. She […]

Kiki D’Aire Humiliated

From a Custom Video – Part 1 of 9: Kiki is done with her business meetings and ready to relax […]

Tia Cyrus Punished

From a Custom Video: Part 1 Tia Cyrus hires a private detective to blackmail her husband. Little does she realize […]

Kendall Earns Her Inheritance

From a Custom Video: Sassy little heiress Kendall thinks she’s got it made. She gets all her daddy’s millions and […]

Jay Taylor, Rough Rocker

Just some fun goofing around with my good friend and fuck buddy Jay Taylor: She plays the bored horny groupie, […]

Faye Reagan, No Choice

This is the last content I ever shot with Faye Reagan. She played a cheating housewife, and I get to […]

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 […]

Holly West Sextoy

From a Custom Video: Holly West is a young struggling model who thinks she’s landed a sweet gig in a […]

Holly West Helpless

From a Custom Video: I have Holly West tied up and helpless on my sofa, AND I have her husband […]

Nicki Hunter Housepet

Final chapter of a Custom Video: I paid good money for my own house-slave and I’m going to use her […]

Mika Tan Sextoy

From a Custom Video: Mika Tan answers a call for a private stripper show. Predictably, it doesn’t go as planned… […]

Amber Rayne, Abducted Attorney

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

Lara Brookes Learns a Lesson

Another Custom Video, from my favorite customer: Lara Brookes comes to Tim for advice about boys. He gladly teaches her, […]

Heather Vahn, Open-Mouthed Doll

Repeat business from a Custom Video customer. Guess I’m doing something right… more like Heather Vahn is. She plays the […]

Lexi Belle in Secretary’s Choice

From a Custom Video: Lexi got caught with her hand in the company cookie jar. Guess where I’m going to […]

Jessica Bangkok Screams Squirms and Swallows

From a Custom Video: I caught Jessica snooping around my office. She tried to sweet-talk (lapdance!) her way out of […]

Tiffany Star Taken

From a Custom Video: Tiffany Star is a Senator’s daughter or something, I don’t know, who cares. Anyway, I get […]

Mika Tan, Assaulted Analyst

From a Custom Video: Mika Tan the Psychiatrist works up a profile on Tim Woodman. She thinks he is delirious […]

Heather Vahn, Obedient Fucktoy

From a Custom Video: Heather Vahn wants to be my slave, so she mails herself to me in a box. […]

Jessie Parker, Blackmailed Babysitter

I caught Jessie lifting cash out of my wallet. Looks like she’s going to have to pay me back the […]

Holly West Blackmailed

Holly West thinks she’s alone at the office so she starts watching porn. Her boss comes in and films her, […]

Madison Scott Snared

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

Taxing Toes

Dorothy Laine stars as the lovely accountant. She gets accosted, tied up, and has her sexy naked feet molested over […]