Hayden Panettiere. Her strict enforced chastity regime makes her one of the toughest instructors at the Sissy Academy.

Hayden Panettiere. Her strict enforced chastity regime makes her one of the toughest instructors at the Sissy Academy.

Anal Training With Ashley Tisdale.

Kate Upton Bursting Out Of Her Bikini Top. Summertime Can Be Especially Tough On Chastity Slaves With All The Skimpy Outfits And Bikini&Amp;Rsquo;S Leaving So Much On Display.

Selena On Her Way To Visit A Slave She Has Decided To Punish With Extra Chastity Time. She Always Makes Sure To Wear The Slutiest Of Outfits When Delivering The Bad News.

Katy Perry. If You Have A Small Penis Never Play This Game Unless She Goes First.

Allison Mack Wins In The End.

Allison Mack No Mercy Keyholder.

Emily Osment

Keyholder Maria Menounos Keeps The Slaves Chastity Key On Display By Wearing It On Her Belly Ring.

Elizabeth Gillies Using Her Cuckold Slave For A Humiliating Task.

Kelly Ripa - By Request.

Hunter King. Real Men Have Football Or Basketball Practice. Sissies Have Cocksucking Practice.

Sarah Hyland

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