Anal Trespassing
When college student Juliette March accidentally trespasses while on a remote field study, the psychotic property owner Tommy Pistol overpowers the helpless student and carries her off to his cabin w...
Do it for Daddy
When a loathsome banker forecloses on her Daddy's ranch, Kira Noir must decide how far she will go to save the family farm. Kira is happily watering the spring flowers in her yard when Tommy Pistol s...
The Made Wife
When a newly widowed mob wife, Raven Hart, gets a visit from her deceased husband's crime partner, Tommy Pistol, she learns the truth about her dead husband: he gambled her away in a poker game. Tomm...
The Honeypot: Mother Daughter Scam Artists Anally Punished By Tech Nerd
Elegant and sexually voracious Cherie Deville, and her innocent teen accomplice Summer Day are a formidable strength of female wiles. They are living the good life scamming and black mailing local te...
Anal Lieutenant
When a sexy young woman living on her own, Casey Calvert, is the victim of some invasion, her 911 call is intercepted by a dirty cop that rolls up to crime scene and starts his anal shakedown. Tommy ...
My Nightmare Neighbor
Tommy Pistol's new neighbor, Britney Amber, comes unhinged and turns into a nightmare so Tommy sets a trap to welcome Britney to his world of bondage and anal sex! After a dispute with Tommy about ga...
Gold-Digging Anal Teen Learns the Old Fashioned Way
With a sexy young body and an airy sense of entitlement, Chloe Cherry is any Step-Mother's worst nightmare. Whenever Chloe needs some more money, she has no qualms about popping by her Step-Father's ...
Heartbreaker
Sexy blonde babe London River has been a bad girl. Her husband Tommy Pistol is convinced she is cheating on him so he hires Xander Corvus to investigate. While London is sunning out by the pool tople...
Alex Harper, Pretty Pale and Pliant
Bound on a square black table with skin as white as snow, Alex Harper is positioned on her back with a red ball-gag between her teeth. Her wrists are tied firmly to the table with rope above her head...
Mob Rules
You are in for a treat with this weeks SAS Thanksgiving update! We got the raven haired bad ass bitch mobster wife with huge beautiful tits Lilly Lane, we got the sweet and pretty long and lean girl ...
Gorgeous Blonde Cadence Lux is a Good Whore
It's Cadence Lux's first training and she's ready to prove herself. She has a beautiful body, perfect breasts, legs for days, and expressive eyes. First, she is tied upright and spread eagle for insp...
The Wrong Girl
Asian cutie Marica Hase is Tommy Pistol's little fuck doll when Tommy accidentally kidnaps the Wrong Girl. Somebody hired him to find a Japanese girl in the Santa Monica mountains but in fact he was ...
Chloe Cherry Gagged and Bound
Chloe Cherry sits, gagged and bound to a wooden chair in a red pleated skirt that's been pulled up to show that her hairy pussy has had an hitachi vibrator secured directly beneath it. Chloe's wrists...
Big Ass-ed MILF Richelle Ryan Trained and Fucked in Rope Bondage!!
Not every wanton whore can become an "O". Every so often an ass comes along that lacks the true discipline required to become an "O" but is so eager to gyrate and please that it melts the icy hearts ...
Cheaper to Keep Her
Raven haired Gina Valentina and boyfriend Tommy Pistol are in love and are going away for the weekend but first they have to stop to give Tommy's ex-wife, Alana Cruise, her alimony. Gina has never me...
Scamming Squirting Slut Punished by Crazy Anal Housewife
It's a battle of the blonds as a scam artist faces off against a sadistic housewife resulting in brutal sybian, squirting, bondage, anal, humiliation, & pussy clamps. Cadence Lux is a hot little ...
Training a Pain Slut: Busty Melissa Moore’s First Submission
Welcome the stunning Melissa Moore for her first submission to The Training of O. This natural busty brunette is extraordinarily obedient and has a cock hungry dripping pussy and mouth. This slave de...
Avi’s Anal Training with her Sadistic Step Family
Avi is a crafty little daddy's girl that arrives at her Step Father's house with plans to get back to her boyfriend, but Tommy's new wife Jessica see's right through her 18 year old lies and puts her...
