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Rated: 18+ · Interactive · Fashion · #1928522
A bunch of stories that all result in a man dressing like a woman.
This choice: A dress, tights and heels.  •  Go Back...
Chapter #5

A dress, tights and heels.

    by: Scifiwizard Retired Author IconMail Icon
Jessie was mortified to see Grace holding up a little girl's pink dress with an ivory sash. With it was a pair white tights and a pair of black thee inch high heels held by Jen, both smiling mischievously. "You will look adorable in this, sweetie." Cooing, Grace said.

Jessie took a step back, shaking his head only Grace pushed him into one of the changing booths, stepping in with him. "Why are you doing this to me?!" Annoyed, Jessie demanded. "You know I'm not..."

"Don't blow a gasket." Lightly scolding, Grace said. "We're just having a bit of fun."

With that, she pulled Jessie's shirt off and pulled down his pants. Jessie wanted to struggle but he knew that he could not run out in just his underwear so he reluctantly allowed Grace to put him into the humiliating outfit. His shoes and socks were removed and mom slid the tights up his legs. The thin fabric felt strange against his skin and he could feel it stretching as Grace pulled them into place. Next was the dress which was much like putting on a shirt only the zipper was in the back where Jessie knew he would have a hard time reaching. What was worse was that the dress was really made for a small girl not a small boy so it was a bit tight on him. He knew he would not get it off without help. Finally, the sash was tied into a neat bow behind his back and he was put into the child's high heeled shoes.

Grace giggled at her handiwork "Aren't you just precious..."

Before Jessie could respond, Grace pulled him out of the dressing room in full view of Jen who giggled at the sight of him. "You look great!" Grinning, she said. "I never thought you'd turn out to be such a cutie!"

Jessie blushed, not liking the situation he was in at all. He was shocked when Grace said, "We'll take it; maybe we can get her to wear it home."

The saleslady smiled, happy to have made a sale, then motioned to the racks of dresses and skirts. "We have a large selection of clothing that will help her bring out her inner princess..."

Grace turned to Jen, smiling then sighed before turning to Jessie. "I think we'll leave it up to our little girl." Grinning, she said. "We know she's more of a tomboy but..." She leaned in close and whispered. "Maybe for a reward, we can get you to play along for a while."

Jessie gulped, wondering what to do.

You have the following choices:

1. He reluctantly agrees.

*Noteb*
2. He wants something first.

*Noteb*
3. Grace decides for him.

4. your choice.

*Noteb*
5. you decide.

*Noteb* indicates the next chapter needs to be written.
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