Mrs. Annette, a mature, lingerie-clad goddess, takes her submissive, SissyBoy, through an intense anal training session. She humiliates him in his college underwear, making him worship her stocking-clad feet and oil-slicked body. Using a strap-on, she pegs him relentlessly in doggystyle, stretching his virgin ass with her massive toy. She dominates him, making him wear a chastity cage and degrading him with anal fingering and hook insertion. The session ends with SissyBoy, fully broken, masturbating his caged cock while Mrs. Annette watches, amused.