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!”



Jennifer H. said...

I love the story. Pure sissification and feminization! The school uniform is a 10!!

Cadney said...

Lovely story! Alan is quite the little sissy! The new uniforms are so darling!

sisssystff said...

I'm so happy for him (soon to be her). Hopefully there's a follow up to how Alan further develops into Alana.

sisssystff said...
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