Archive | Bondage

Janira Wolfe & Cupcake SinClair in “Violet Wand”

Tim and Janira have a very special way of showing their love for each other: Tim brought home a Cupcake […]

Nikki Delano & Tia Cyrus Sister Slaves 2

Custom Video sequel: Tia Cyrus and Nikki Delano are still slaves to the mighty Beast. They endure horrible torments including […]

Lauren Phillips in Yoga Bondage

Lauren Phillips thinks she’s here for a Yoga lesson, but Miles Long and I have a better idea. We convince […]

Janira Wolfe & Cupcake SinClaire Double Bound

(Cupcake and Janira’s very first day filming together, you’re welcome!) Why is it that every all-girl sleepover seems to include […]

Odette Delacroix 2 Ways

This is like a choose your own adventure: Does she love it or hate it? Option 1: Odette meets her […]

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 […]

Janira Wolfe & Star Nine in POV Flogging

Did you ever want to have two amazingly sexy blondes, tied together in a double spread eagle on your bed? […]

Lily Lane in Sweet Dream

Lily Lane lays in her bed, dreaming of what all kinky chicks dream of. In her mind’s eye she is […]

Alyssa Lynn Cheesecake

If you want to talk classic adult performers you need look no further than Alyssa Lynn. Platinum blonde hair, hypnotically […]

Jelena Jensen Spreadeagle

From a Custom Video – Jelena Jensen was making a fuss at her son’s soccer game. In what might not […]

Kat Dior Sensual Consensual

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

Janira Wolfe Stabbed

Pretty little Janira is bragging on the phone to her friend about how well her divorce turned out for her. […]

Lily Lane Forced Orgasm

I keep trying to come up with a clever way to say HOLY FUCK how did I get Lily Lane […]

Riley Reyes in Mutual Bliss

It’s safe to say I’m going to work with Riley Reyes every chance I get. Here’s a little clip we […]

Charlotte Cross and Cupcake SinClair in “Caper”

Charlotte Cross and Cupcake SinClair in “Caper” – Short version: two sexy naked chicks tied up and being very, very […]

Kat Dior, Perfect Little Pet

My perfect little pet Kat Dior waits in her birdcage. She sways and writhes slowly in her confinement, wearing only […]

Jelena Jensen Bound for Your Pleasure

Okay. I admit I’ve known Jelena Jensen for years and never had the chance to hire her before now and […]

Lily Lane and the Attic Monster

Lily Lane must have heard a noise or something. So, naturally, she went upstairs to investigate. In a red satin […]

Lauren Phillips Fuckdoll

Lauren Phillips is one spectacularly sexy woman. She has curves in all the right places, a dazzling devious fun loving […]

Riley Reyes Abducted

The very first time I worked with Riley Reyes! She dressed in a lovely silk robe and gown, I snuck […]

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, […]

Kat Dior Double Crossed

I saved up my Villainous profits just so I could work with this girl. This is NOT a custom video, […]

Janira Wolfe Zapped

Lovely Janira Wolfe sits in her bedroom fixing up her pretty toenails. A masked intruder sneaks up on her from […]

Cupcake and Star’s Bondage Fantasy

I swear sometimes this stuff just writes itself. Adorable Cupcake SinClair and Beautiful Star Nine in sexy satin slips on […]

Lily Lane in Biker’s Bait

Sexy Lily Lane in her cutoff jean shorts and tank top, leather vest and boots, is bound to a chair, […]

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 […]

Charlotte Cross Abducted

Okay this one’s creepy, even to me. Thanks to awesome acting jobs by both Charlotte Cross and Cupcake SinClair… Our […]

Tia Cyrus Suspension

Tia Cyrus said she’d never done a full-on suspension before soooooo…. We did one. Enjoy her adorable giggly banter as […]

Janira Wolfe Whipped

Janira and I had some spare time but no cameraman so we set up a tripod and had a little […]

Lauren Phillips Spreadeagled

Yet another Custom Video, this one featuring the AMAZING Lauren Phillips as a snobby snotty Jersey girl. Her father’s connected […]

Cupcake Brutalized

Bad slaves are sent to a special place, to be punished and re-trained by a cruel Master. Poor Cupcake kneels […]

Christina Carter in “Teacher’s Bound Orgasm”

FINALLY I get Christina on my site! For our first collaboration she plays a teacher who just gave a flunking […]

Janira Wolfe Abducted

Sexy stripper Janira’s pissed. The Club owner left her alone and she has to clean the whole place by herself. […]

Tia Cyrus Trained

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

Cupcake SinClair in Street Abduction

Cupcake SinClair in Street Abduction – Adorable little Cupcake is done with work and the last to leave. As she […]

Lauren Phillips Bondage Orgasm

New porn crush: Lauren Phillips is amazing. She’s got a perfect body, incredibly fun-loving but wicked smile, and is a […]

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 […]

Gag Reel 04

Yet another star-studded compilation of goof ups, fumbled lines, behind-scenes antics, and various hilarious out-takes from the set of ProVillain […]

20 Years of Villains Life

April 2016 marked my 20th anniversary in Porn! Here’s a compilation of highlights from my glorious career so far. I […]

Danica Dillon Spreadeagle

From a Custom Video featuring gorgeous and amazingly feisty Danica Dillon – her boss thinks she’s acting out too much […]

Sinn Sage Abducted

Beautiful Sinn Sage, wearing only a purple silky slip, steps up to the bathroom mirror to preen. Little does she […]

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 […]

Cupcake and Star in “Creepy Bondage”

A dark abandoned warehouse… Two beautiful carefree giggling girls play would-be detectives. You creep up behind them, perving on their […]

Danica Dillon Straitjacket Fun

Gorgeous Danica Dillon’s long lovely bare legs and feet, tight white canvas straitjacket, her beautiful face adorned with a bright […]

Behind the Scenes with Sinn Sage

For those who like to watch the rigging, here’s some Behind Scenes footage we got of Tim Woodman tying the […]

Tia Cyrus Bondage Orgasm

Just a little sensual consensual bondage play for you all featuring the amazingly lovely Tia Cyrus: Watch her squirm and […]

Jessica Jaymes Broken

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

Chanel Preston Chloroformed

Lovely Chanel Preston is washing up in the kitchen, looking oh so fetching in her tight jeans and sheer top. […]

Cupcake and Star “Sleepover”

In this POV clip we see Cupcake and Star in sexy lingerie, snuggled up and sleeping in the same bed. […]

Stacy Burke Ravished

From a Custom Video: Remastered re-released footage of the lovely legendary Stacy Burke! In part 1 we see Stacy in […]

Cupcake and Star Whipped

Just a lovely little clip of two perfect bottoms in consensual BDSM play. Cupcake loves to wear her Vampire Cuffs […]

Jessica Jaymes Humiliated

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

Chanel Preston Suspension

Superstar Chanel Preston plays a superheroine, albeit an unfortunate one. She is bound in a tight hogtie and suspended mid-air. […]

Karlee Grey Spreadeagle

From a Custom Video: Karlee Grey is naked and strapped into a white posey straitjacket. A chain connects her collar […]

Cupcake and Star Double Bound

The three of us have been working together a lot lately, which is well, fucking awesome. Cupcake and Star are […]

Jessica Jaymes Totally Fucked

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

Karlee Grey Wants to Play

Part 1 of 3 – Adorable Karlee kneels patiently in Present Position, completely naked, hands palm-up on her knees. Master […]

Tia Cyrus Damsel Noir

My little tribute to Film Noir stars Tia Cyrus as a Dominatrix who gets abducted and forced to strip at […]

Kiki D’Aire Humiliated

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

Rahyndee James Spreadeagled and Chloroformed

From a Custom Video… Clip 1 of 4: Rahyndee James is a simple girl, cheerful, not that bright, and does […]

Rahyndee James Abducted

Just a bit of classic Villainy: Gorgeous (I mean really and truly fucking GORGEOUS) Rahyndee James sleeps in a lovely […]

Tia Cyrus Punished

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

Alessandra Noir Bound and Gagged

We had a few spare minutes after our custom video, so I tied and gagged Alessandra Noir on a sofa […]

Detective and Damsel Knocked Out

Detective and Damsel Knocked Out! Starring Dixie Comet and Star: Wealthy heiress Star has been abducted. She is bound and […]

Jessica Jaymes Learns a Lesson

From a Custom Video: This is actually a sequel to my first Jessica Jaymes Custom. She is now a bought […]

Jay Taylor and Paisley Parker Spanked

Jay Taylor and Paisley Parker lay on a table, asses in the air, while Tim ties them down. There are […]

Learn to “Rig Like a Villain!”

From my DVD “BDSM 0-60 #1 Rig Like a Villain” I finally share my wealth of dastardly devious knowledge and […]

Paisley Parker Double Dommed

I love working (read that ‘fooling around’) with Jay Taylor. Even better I love it when she brings me a […]

Amber Rayne Whipped

Amber and I had some spare time left at the end of a shoot and decided to essentially record a […]

Cupcake Sinclair in “Housekeeping!”

Presenting the Internet Porn debut footage of our very own Cupcake Sinclair! She starts her performance off with a bang, […]

Dixie Comet and Star Stabbed!

Stabbed in the Guts! Starring Dixie Comet and Star (and me in my very best “Dexter” getup heh heh heh): […]

Alex Chance Interrogated

From a Custom Video: (part 1) Alex Chance is in serious trouble! Seems she was on a nursing mission to […]

Nicki Hunter “Body and Soul”

In co-production with Severe Society comes the next in our “Devil’s Workshop” series! I’m so very proud to get to […]

Play Doctor with Jay Taylor

Doctor Woodman (I know I know, just go with it, okay???) has finished a 16 hour shift but apparently he’s […]

Amber Rayne Suspension

Amber Rayne is one of the best bondage models I’ve EVER worked with. We’ve been friends for years and I […]

Alex Chance and the Timebomb

Poor Alex Chance has been taken hostage! She stands tied to a pole outdoors, one leg bent, intricate ropes wrapped […]

Jay Taylor Bound Maid

Good help is hard to find when you’re a Villain. Jay Taylor is the most perfect, scrumptious delectable French Maid […]

Cassidy Banks Spreadeagled

From a Custom Video: (I get to work with some GORGEOUS women thanks to my custom video customers, and Cassidy […]

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 […]

Cassidy Banks Bound

Just some classic bondage for you to enjoy: Cassidy Banks is a beautiful dark-skinned bombshell, with lovely eyes and the […]

Star Stabbed in the Guts

Watch closely as Star, without a care in the world, slips out of her white bathrobe. Look at her lithe […]

Brooke Haven Spreadeagled

From a Custom Video: Brooke Haven finds herself naked, bound spread-eagled to a bed. She squirms and struggles, but can’t […]

Brooke Haven’s First Straitjacket(s)

Just when you though the legendary sex goddess Brooke Haven was out of ‘firsts’ we realize she’s never been in […]

Alex Chance, Abducted Sextoy

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

Bloopers, Boobs & Out-takes!

A Villain’s work is not always serious. Take a peek at me and my all-star sexy friends in a behind-scenes […]

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 […]

Ela Darling Abducted and Tormented

From a Custom Video: Ela Darling is getting ready for a hot date. She finishes touching up her make-up in […]

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 […]

Darla Crane Stabbed to Death

It is always an honor to work with the legendary Darla Crane. She is in this Villain’s mind still the […]

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 […]

Star Jungle Girl

Never miss a chance to work with Star. She’s still one of the best fetish models I’ve ever worked with. […]

Amber Rayne Hot Wax

Amber Rayne is still one of my all-time favorites. She has it all, looks, flexibility, super-high pain tolerance, professionalism, she’s […]

Breaking Nicki Hunter

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

Jay Taylor Playdate

From a Custom Video: Jay Taylor was a little nervous about a BDSM playdate but I promised to be gentle. […]

Lexi Belle, Pleasure Slave

From a Custom Video: What can be better than opening a shipping crate and finding your very own Lexi Belle […]

Mika Tan Sextoy

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

Sarah Blake Slave Training

Investigative reporter Sarah Blake scores an interview with the infamous ProVillain but she gets more than she bargained for. He […]

Isobel Wren Tortured

From a Custom Video: Isobel Wren strolls down a hall, all long legs and sexy curves. An intruder grabs her […]