Lady Jessica looks stunning in her black elbow-length gloves and stockings. She studies Freddy and starts training him to be her new sissy. The bizarre blonde puts a black wig on him and dresses him in sexy black lingerie and stockings. She gives the slender crossdresser the new name of Chantal. He makes a pretty good transvestite but he must pass the ultimate test of walking in white high-heeled shoes.
Lady CherieNoir remains fully clothed as she puts on her big black strapon. She wears black gloves as she makes her masked sissy slave suck the dildo. Her hot pink long-sleeved blouse matches the color of his mask. She tells him to be a good sissy and take the sex toy deeper into his mouth like a good little bitch. The blonde Mistress then ass fucks his tight man pussy hard and deep as a reward.