Bailey's Chastity Breaker: Fucking Sissies

Bailey Wilde, the formidable femdom, introduces Jake Grand, her latest sissy conquest, to Cassidy Cream, her ever-eager transsexual assistant. Jake, bound and gagged, is already in chastity, his cock straining against the device. Bailey, relishing her power, makes Jake lick her boots clean before presenting him with a choice: endure her mercy or face Cassidy's. Jake chooses Bailey, and she grins, revealing a massive, realistic strap-on. Cassidy lubes it up, and Bailey, with a wicked laugh, pushes Jake's limits, running the head of the dildo along his ass crack, teasing his chastity cage, and finally, with a swift thrust, breaking his chastity and fucking him raw.

• femdom
• new
• transsexual
• sissy
• femboy
• chastity-pegging

• shemale