Archive | Fucking

Riley Reyes Hypnotized

Ultra Badass Domme Riley sits on her throne, confident in her power, taunting her fans online. Then her new supplicant […]

Makayla Cox Ritual Sacrifice

Let the Ritual begin! Our Sacrifice is tied to the table, wearing only a purple satin slip. She looks around […]

Ashley Lane “Midnight Snack”

Lovely long legged Ashley Lane goes down to the kitchen for a late night snack. She’s wearing only her satin […]

Charlotte Sartre Stripped Whipped and Fucked

This was NOT a Custom Video. I’ve been wanting to get my Villainous hands on the delightful Charlotte Sartre for […]

Lydia Black Drugged and Raped

From a Custom Video: Lovely little Lydia checks into a BnB for a night to herself, or so she thinks. […]

Kira Noir Domme Dommed

Gorgeous Kira Noir sits all regal and powerful in her throne, prepared for another FemDom humiliation session. She doesn’t know […]

Charlotte Sartre Pays a Debt

Gotta love a sexy but clueless little goth girl. Her lesbian girlfriend sent her to the classroom after school, knowing […]

Kira Noir Re Trained

From a Custom Video: Kira Noir has failed her Master. He loaned her out and she was returned as an […]

Bank Robbery Rape and Murder Starring Chanel Preston & Christiana Cinn

From an AWESOME Custom Video: Christiana Cinn is a bank manager, Chanel Preston her trusty security guard. They are helping […]

Penny Lay Drugged Raped and Murdered

Super sexy redhaired beauty Penny slips away from the slumber party (or whatever event she was attending in just a […]

Kira Noir in “Blackmail Backfire”

From a Custom Video: Kira Noir flirts her way into an embrace with her professor then snaps some blackmail photos […]

Blair Williams Punished

From a Custom Video: Amazingly sexy Blair Williams (my Custom Video guys sure do have great taste!) Is sent back […]

Gina Valentina Duct Taped and Raped

From a Custom Video: Sexy little Gina is straightening up papers in her classroom when a Villain (that’s me, duh) […]

Tia Cyrus Fucks the Devil!

In life, Tia Cyrus was a bad girl. Now she’s in Hell, bound naked and helpless, surrounded by skeletons and […]

Jessica Jaymes and the Hood

Legendary Jessica Jaymes returns for a 7th installment in her slave training series. The once proud district attorney has been […]

Athena Palomino Straitjacket & Spreadeagle

From a Custom Video – the amazingly gorgeous Athena Palomino, moments before signing an exclusive contract, shot this little bondage/straitjacket/force […]

“Double Teaming” featuring Abbey Rain & Tia Cyrus

From a Custom Video: Innocent Real estate agent Abbey Rain is showing Tia Cyrus and Tim Woodman a lovely home. […]

Stephie Staar Nurse Drugged

Stephie Staar is dressed as a sexy nurse. I could really just stop writing the ad copy right there, couldn’t […]

Marie McCray vs the Witch King

From a Custom Video: Marie McCray is a Witch Hunter. You can tell by the required uniform: Skimpy suede bikini. […]

Tia Cyrus Open Mouthed Doll

From a Custom Video: Tia has been a bad slave. Her Master loaned her out to a friend and she […]

Marie McCray Drugged Drink

Marie is working late at the office. She takes a break for some coffee when in walks Tim. It’s just […]

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 […]

Tia Cyrus and Nikki Delano in Sister Slaves 3

From a Custom Video: The continuing saga of real life sisters Nikki Delano and Tia Cyrus, once sexy camgirls, now […]

Abbey Rain Bondage Sex

Lithe lovely Abbey Lane is tied up tight, arms in a boxtie, Gunslinger crotchrope around her waist and thighs, waiting […]

Stephie Staar Bondage Sex

I first worked with Stephie for BitchSlapStudios.com in Portland. We hit it off great and had a wonderful day together, […]

Pepper Hart in “Roulette”

Pepper sleeps safe and sound in her bedroom until an Intruder breaks in. He takes a moment to fondle her […]

Pepper Hart’s Pervy Pics

Luscious young Pepper Hart sneaks into her Uncle Tim’s garage where he is passed out drunk. She knows he’s the […]

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 […]

Abbey Rain in “After School Special”

The uptight straight-laced straight-A student always has a secret, doesn’t she? In this case meet Abbey Rain, perfect student by […]

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 […]

Lauren Phillips Fuckdoll

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

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, […]

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 […]

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 […]

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 Broken

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

Stacy Burke Ravished

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

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 Raped

Gorgeous Chanel Preston is hosting a dinner party. She steps away for only a moment, into the restroom to freshen […]

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 […]

Alessandra Noir Cheerleader Punished

4 part series from a Custom Video: Part 1 of 4 – Alessandra Noir can’t make cheerleader practice, she is […]

Tia Cyrus Punished

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

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 […]

Amber Rayne Overpowered

From a Custom Video starring my good friend Amber Rayne: In this one she plays a gung-ho detective, perhaps a […]

Cupcake Finds a Gun

Cupcake can’t sleep. She wanders into Daddy’s room but he’s not there. She tries to get comfy on his bed […]

Cupcake Sinclair in “Housekeeping!”

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

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 […]

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 […]

Alex Chance and the Professor

From a 2-part Custom Video: Part 1 – Alex thinks she can flirt her way out of a bad grade […]

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… […]

Lana Violet Kidnapped

From a Custom Video: Lana Violet steps into the bathroom and is attacked by a Villain with a knife! She […]

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, […]

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 […]

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 […]

Hope Howell Kidnapped and Trained

From a Custom Video: Young, petite Hope joins Tim’s bevy of kidnapped pleasure slaves. He carries her in, bound and […]

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 […]

Nicki Hunter and Britney Amber Choked and Raped

From a Custom Video: Nicki and Britney dressed in sexy skimpy French Maid costumes tease and taunt a little too […]

Mika Tan, Assaulted Analyst

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

Tiffany Star’s Bad Day

From a GREAT Custom Video, 3 stories: Tiffany mouths off to the Principal, and gets a harsh spanking for punishment. […]

Amber Rayne Sextoy

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

Alex Chance Home Alone

New Bride Alex Chance gets stood up by her busy husband again. Lucky for her there’s a masked intruder in […]

MinxGrrl in Stripper Ravished

When Minx saw Tim in the stripper bar, she knew she just HAD to give him a lapdance and a […]

Tyler Faith Rich Bitch Raped

Tyler Faith (who is in real life a total sweetie) plays a rich bitch who ends up in an empty […]

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 […]

Angel Dark in The Judge’s Wife

From a Custom Video: Angel Dark plays the trophy wife of a Judge who tried to take on the Slave […]

Holly West Blackmailed

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

Nicole Oring Punished

Sexy Secretary Nicole Oring thought she could steal from my company… she soon learns a painful price! She gets panked, […]

Awakening the Ancient One

My very own live action tentacle-rape Lovecraft/Cthulu style Horror porn! Aiden Starr joins me in the bizarre Ritual we perform […]

Asa Akira Ravished

I knew I needed to hire Asa as soon as I met her, and I saved up to produce this […]

Faye Reagan’s Nightmare

If you’re gonna hire Faye Reagan you’d better go all out and make it MEMORABLE! So I got a full […]

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 […]

Faye Reagan Snatched, Stripped and Fucked

Now HERE’s a story I can get behind! Masked Intruder breaks into lovely model’s house, holds her down, strips her, […]

Tyler Faith, Ravished Rockstar

Legendary Pornstar Tyler Faith as a rockstar gets attacked by a crazy fan/stalker! He chloroforms her, ties her up, whips […]

Faye Reagan Schoolgirl Scandal

Faye goes to a photographer to get some modeling shots, but she doesn’t tell anybody where she’s gone. Once the […]

Madison Scott Snared

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

Stacy Burke Trouble Sleeping

Poor Stacy is having trouble sleeping. She takes several dozen pills and with a comic eye-crossing wobble, she’s out like […]

Jade Indica Working Late

From a Custom Video: Jade Indica is working late at the office and gets distracted by her own beauty in […]

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!) […]

Holly West Secretary Slave

Holly West is just a cute secretary at Tim’s firm, until she catches his eye. He handcuffs her at gunpoint, […]

Rachel Roxxx Super Battle

Bubbly Cheerleader Rachel gets attacked & chloroformed by a Villain. He is about to carry her away when she awakens […]

Kylee Strutt Bondage Princess

Incredibly gorgeous newcomer Kylee Strutt, in her first ever bondage production! She’s the sexy stripper, I’m the well-dressed burglar… Kylee […]

Tyler Faith in Rough Therapy

What happens when a well-intentioned and large-breasted therapist thinks she can cure a Villain of his evil ways? Well DUH […]

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 […]