Thursday, May 2, 2024

Five Days to Sissy


By now, Alan’s mornings had a regular routine. He awoke to find his lingerie on his dresser. He put them on, then reported to the dressing room where Violet did his makeup and supervised his dressing for the day. “Today, Master Alan, Ma’am and I will pick you up at school and we are going shopping. Won’t that be fun!” Knowing that any other response would be of no avail, he smiled and nodded.

School that day was much like the day before. He joined the other sissies in their activities. For the first time, he noticed that he was the only one wearing obviously male footwear. The other sissies were shod in a variety of ways, but all of them quite feminine and girly. A few wore sneakers in pink, some had on ballet flats. Patent leather, both black and pink, seemed to be popular. And one sissy minced about in a pair of pumps with four-inch heels. Oddly, Alan found himself envying his classmates with the most girlish shoes.

As he exited for the day, Violet met him and escorted him to his stapmother’s car. Without a word, they drove to the local mall. Upon arrival, his stepmother directed them to a shoe store. “My sissy stepson requires an appropriate pair of shoes,” she told the clerk, who rushed off and returned with a half-dozen choices, ranging from pink mary-janes to stunning high heels. Alan’s eyes were drawn to a pair of mary-janes in black patent, with low heels and a glittery bow on the instep.

“Yes, these are a very popular style among our sissy clientele,” the clerk commented. “We also have them in pink and red, of course.”

“We’ll take a pair in each color in Alan’s size,” his stepmother said. “Violet, assist him in getting into the black patent pair while I arrange payment.” Violet helped him slip into the shiny shoes and buckled them tight. When stepmother returned, she had another small item with her. “Use these locks to secure the shoes to his feet,” she told the maid. “Alan must get used to wearing them constantly.” Violet inserted the tiny silver locks into the buckles of each shoe, closed them and handed the key to his stepmother, who dropped it into her purse.

On rising, Alan discovered even these slight heels altered his posture and gait. He realized he now walked like a girl!

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