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38. Trying before buying

37. From Shorts to Skirts

36. Arriving at the Mall

35. New Friends

34. Reaching a Deal

33. Tiffany Sanders

32. After School

31. Taking Stock

30. New Shoes? Already...

29. Eyeliner

28. Last Class of the Day?

27. Wrong Answer

26. After Class

25. Lower Down yet Higher Up

24. Zoe's Friend

23. Amber's Rule

22. Lipstick challenge Failed.

21. To the Cafeteria

20. Daring Escape (Alternate)

19. Sissy Curse: Womanly Figure

Sissy Curse: Trying before buying

avatar on 2021-09-12 20:04:58

1606 hits, 181 views, 6 upvotes.

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Behave and I become a girl. Misbehave and I become a sissy.
I must keep my hair styled and presentable at all times. - SISSY RULE
If I'm around other people, I need to be wearing lipstick. - SISSY RULE
I must walk like a lady at all times.
I am not allowed to wear men's shirts. - SISSY RULE
My name is Jenna, not Jon. I must also use female pronouns. I must correct people who use the wrong name or pronouns when talking to me.
I must wear a bra at all times.
My bra must be filled at all times.
I must use the girl's bathroom when considered a girl, and the boy's bathroom when considered a sissy.
I must regularly check and maintain my makeup.
I must wear women's shoes. - SISSY RULE
I must wear and maintain my eyeliner.
I must have an active Girl's Social Life

"Oh I have just the thing." Ami scribbled something in Jon's Notebook, before handing it back smiling

Quickly looking at the book, desperate to know what Ami had cursed him with

"I must flaunt my legs with short skirts"

"Let's start shopping, you wouldn't want to break that rule would you Jenna?" Ami said. it was clear, unlike the past, Ami wasn't going to just hand him a skirt to wear, He'd have to buy one himself... and quickly... who knows how long it would take for one of the girls to decide he was breaking the rule by wearing his cargo shorts.

Ami, began browsing the racks holding skirts up to Jenna.

Jon wanted to say no to each and every one, they were all so stereotypically girly, not that their were really any skirts that didn't look girly. Finally he got desperate and took one.

As he was about to head to the register to buy his own skirt Ami stopped him.

"Jenna, girl's don't just buy the first thing they see, the try on way too many, comparing them, asking which one looks the best, take all of these and try them on"

To Jon's dismay Ami handed him easily or 7 more skirts, and He, Ami, Holly, and Kylie headed towards the women's changing room. Tiffany was still off finding a purse apparently.

In the changing room, alone for a moment, Jon breathed a sigh of relief. He checked the time... damnit... the drive here and all this had only taken just over 15 minutes, he had another hour 45 until he could convince tiffany to let him go home.

He stripped off his cargo shorts, getting his phone and wallet out of his pockets as he was more than likely not going to be putting them back on.

He almost took off his Sissy heels to help get the shorts off but worried someone could punish him for it so he slipped his shorts off over his garish pink heels.

Next he stepped into the first skirt in the pile, a straight denim skirt, wiggling it on, as it was pretty tight, he zipped the zipper securing it Just as Ami and the girls began hounding him to come out and show off his skirt.

the girls paraded Jenna to a set of triple mirrors and oohed and aahed but finally decided it wasn't right... he came back out in the white A-line skirt, then some sort of skirt made of a wide belt then a flared out bit. The a typical plaid school girl skirt...

with each skirt the girls turned down Jon saw his pile of options growing thinner, the last one he really wanted to avoid was a short pink layered skirt... he really wanted to avoid more pink, he was decked out with pink hair, pink barrettes, glittery pink lipstick, pink sissy heels with bright white knee socks... he really wanted to avoid the pink skirt, trying to avoid looking like a total Barbie.

Obviously... thought the girls liked the rest of the skirts, but one by one, all were turned down, Jon slipped into the pink skirt knowing either they'd agree it was the skirt for him, or their would be more skirts to try on.

...Jenna's new skirt

on exited the changing room Tiffany was back, and together his new friends agreed, that this was the skirt for Jenna. Though they also agreed that something would have to be done about her underwear, the dark blue boxers just didn't work with Jenna's new style.




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