Friday, May 3, 2024

Five Days to Sissy


“There will be a surprise for you at school today, Alan,” his stepmother told him as ate breakfast.

“Haven’t I had enough surprises this week?” he asked, looking down at his burgeoning breasts, his shiny shoes with their bows and all the other changes he had gone through since Monday.

“I’m not responsible for this one,” she replied…well, not directly, she thought to herself.

Thirty minutes later, Alan sat with the other students in the sissy section as the principal explained some new rules. “The board has decided it would be best for all our students if the sissies are required to wear the same uniform as the…um…real young ladies in the student body. So, for those of you who have been wearing trousers or non-regulation skirts and dresses, you will find your new school clothes in your lockers. As I said, they are identical to the outfits all the girls wear—with a few modifications to make it clear you are decidedly not real girls. Go now and change.”

Apprehensive, Alan went to his locker and found the uniform. It consisted of a crisp white blouse with the school emblem and a pleated tartan skirt. The difference from the “standard” uniform? The skirt was incredibly short—ending a full nine inches above his knees and beneath it was a built-in petticoat that made it seem even shorter and girlier. The accessories were a bow at the collar in the same pattern as the skirt and white knee socks. A note was pinned to the blouse: “Shoes are the sissy student’s choice, so long as they are black patent leather.”

Resigned to his fate, Alan removed his male shirt and pants and put on the blouse and skirt. He removed his shoes, pulled on the knee socks, then stepped again into his mary-janes. He glanced around the locker room at the other sissies. Yes, this had made them all look very feminine, even the ones who didn’t wear makeup…and the ones who sported C-cup tits and high heels looked positively womanly.

He finished the school day and was met by Violet and his stepmother. “At last, my sissy stepson is complete! Come with me, we will celebrate by buying your first party dress!”


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!

Wednesday, May 1, 2024

Five Days to Sissy


So, it turned out school wasn’t nearly as bad as Alan imagined. Since his stepmother had advised the administration, he was transferred to a special section for sissies and other feminized boys. There were ten other students in the group, in various stages of transition. A few were nearly impossible to distinguish from true females and one was wearing just lipstick to acknowledge his emasculated status.

Still, Alan was alarmed when he awoke to find yet another step would be taken on Wednesday. In addition to a pair of lacy pink panties, a matching bra lay upon his dresser. “Bring this to the dressing room” said the accompanying note. Knowing by now that there was no use in resisting, he pulled on the panties, picked up the bra and followed instructions. Violet was waiting for him at the vanity. “That’s a good sissy,” she said, smiling. “Now, sit while I fix your face and then we’ll try on your bra.” Within minutes, she was done. “Stand up, dear.”

Alan obeyed and the maid wrapped the delicate pink device around his chest, hooking it in the back. She reached into a drawer of the vanity and produced a pair of false tits. Alan gasped, “Please, Violet, hasn’t this gone far enough?”

“Your stepmother has directed this, and it will be done,” she replied, as she slipped the two pieces of foam into pockets in the cups of the bra. She made sure they were arranged properly and stepped back. “Hmm, I’d say 32-B, just the right size and shape for a sissy your age. As you grow older, we may make them a bit bigger! Now, your school clothes…..” She handed Alan a tight-fitting t-shirt that clung to his bust, outlining the shape, and making the bra straps and back quite obvious. His trousers were a pair of stretch jeans with hems above his ankles, so that the sheer nylon socks he wore were evident. “Go to Ma’am’s room and let her see what a prissy little thing we have made you into.”

The tight jeans restricted Alan’s stride to a ladylike mince as he went to his stepmother’s boudoir. As usual, she was sitting in bed in her revealing negligee and she smiled as Alan entered. “How delightful you look, darling,” she cried. “Come closer.” Alan approached her bed. She reached out and gently stroked his faux breasts and then let her hand stray to the bulge at his crotch, feeling it twitch as she ran her hand over it. “Yes, all the expected reactions!”

She summoned Violet. “Master Alan is ready for school….and we have preparations to make for tomorrow!”