Discovering Mistress Sarah's World Part 8

"Yes Mistress!"

Miss May's fucking slowed but she penetrated deeper into his boy pussy. "Mmmm. You are my bitch! I'm going to fuck your sissy pussy every night and you are going to enjoy it! I'm going to keep you locked up and dress you like a pretty sissy! You are so weak slave! My weak little sissy slave!"

Miss May repeated these words over and over again while she fucked Josie. Finally she dismounted him and pushed him away. She threw him the strap-on on and ordered him to clean it and then lock his chastity device back on.

The rest of the week went in a similar manner. Each day he went to work and then came home and helped with the sale. He would then shave, take a bubble bath, pretty himself up and spend the rest of the night serving and pampering Miss May. Each night Miss May pegged him in the ass with a strap-on. By the end of the week she had moved up to a larger strap-on, congratulating Josie on how well his boy pussy was molding into the perfect fuck toy.

The only thing that remained different from his Monday routine was the Miss May did not let him out of his chastity device. She took great pleasure in pegging him and demeaning him while his cock remained locked-up.

Josie's apartment cleared out quickly during the week. Miss May ended the sale on Saturday evening. That night Miss May allowed Josie to drink champagne with her to celebrate how successful the sale was and how much money she made on the sale.

On Sunday, Miss May had Josie dress in completely feminine attire. He wore a plain shirt with a black skirt. Underneath he wore pantyhose and a lace bra that was filled with his false tits. Miss May require him to put on his blond wig and a full face of make-up with glossy red lipstick. He was also required to wear his black heels. It was not the most comfortable outfit for working around the house, but comfort was not Miss May's concern.

When Josie was dressed, Miss May informed him that someone would be coming soon to look at his car and he was to be on his best behavior.