Natasha Lynn is scheming to marry Big John for his money. His son, James Deen, finds out about her true motives and decides to teach her a lesson with sexual punishment and humiliation. This is a fun fantasy role play where Natasha gets an intense and very satisfying sexual BDSM experience.

Iona Grace applies for a job as a bartender but finds herself auditioning to be a plaything for a private kinky event. James Deen puts Iona through her paces with corporal punishment and rough bondage sex in this great update!

Seda And Violet Monroe are made to compete for the opportunity to stay as a servant in James Deen's Manor. Both girls wrestle for cock and push there limits to impress their master. They deliver some hot bondage sex scenes with anal and an incredible double fisting!

In this playful yet intense opening scene, Lana Violet wrestles with James Deen in an attempt to get free. Overpowered and exhausted from struggling, she falls into submission and receives a firm punishment. She is tied up in various positions including a unique suspension and fucked thoroughly.

Busty blond Devon Taylor does her first ever sex scene with James Deen in this erotic nightmarish fantasy role play. Confined in the worst prison on earth, Devon is used as a sex slave by the guards. She is caught trying to escape and is tied up, punished and fucked by the the prison's most sadistic staff member

Ashli Orion and James Deen play a kinky couple in a D/s relationship. Ashli enjoys getting attention from James by being punished and purposely comes home late dressed like a slut. James manhandles her and fucks her ass in tight bondage!

19 year old Lily LaBeau gets her first taste of BDSM and loves it! Her submission is breathtaking, suffering beautifully under James Deen's stern domination. This is an intense scene with genuine reactions from a beautiful girl and great chemistry

19 year old Lily LaBeau gets her first taste of BDSM and loves it! Her submission is breathtaking, suffering beautifully under James Deen's stern domination. This is an intense scene with genuine reactions from a beautiful girl and great chemistry. Includes bound fisting, anal toys, caning, sex and bondage, rough sex, deep throat and orgasms!

19 year old Lily LaBeau gets her first taste of BDSM and loves it! Her submission is breathtaking, suffering beautifully under James Deen's stern domination. This is an intense scene with genuine reactions from a beautiful girl and great chemistry. Includes bound fisting, anal toys, caning, sex and bondage, rough sex, deep throat and orgasms!

Another unsatisfied husband sends his wife to the Spouse Training Institute ran by head mistress Isis Love! Tara Lynn Fox gets intense and erotic lessons on how to service James Deen with her body and mind. This update has great chemistry, fun role play, hot bondage sex, big orgasms and anal penetration!