Discovering Mistress Sarah's World Part 9

He walked to the register trying to look calm and relaxed but he could feel the redness on his face. The cashier acted normal when he put the tampons on the counter but Josie could barely look into her eyes. He quietly paid and then left the store. Josie was certain the cashier was laughing at him under her breath.

Thursday morning before work, Miss May had Josie bend over while she inserted the shell of the tampon just inside his boy pussy. It hurt at first, but then Miss May held the shell and pushed the "tail" forward forcing the firm cotton tampon out of the shell and deep into his ass. Josie felt a twinge of embarrassment at how good the cotton felt inside his ass. When his mind cleared of the sinful pleasure, he noticed the pretty feminine scent from the tampon package, which filled the small bathroom. The feminine scent combined with the feeling of the tampon inside him, mentally put Josie into a girly mood.

Miss May had him dress in pink panties, pink stockings, and a garter belt. She allowed him to wear socks to cover the stockings, but the socks had frilly lace at the top. Josie worried that if he sat down at work, his pants legs would ride up just enough for someone to see the lace.

Concerned he said to Miss May, "What if someone sees the lace on my socks?"

Miss May laughed. "Well then they'll know you are a sissy. I'm sure they've figured it out already sweetie. Your feminine side is really showing this week."

Josie remained quiet. He knew there was no arguing with Miss May. She was enjoying putting him in these awkward situations. Miss May also dressed him in women's pants and a woman's blouse. Then she penciled in a thin line of eyeliner above his lashes and dabbed a hint of blush on his cheeks.

Miss May handed him an individual tampon which was still in the pink plastic wrapping. "You're going to need this princess, just in case you have your period and need a fresh tampon."

The notion of him having a period was silly but it made his confined clitty twitch in his panties.