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Description
When Scott learned he was going to his hometown’s summer fair, he pleaded nonstop for his mom to let him go in boy clothes. All of his classmates would be there, along with the rest of the town.After a while, she relented. “Fine Scott, I’ll dress you like a boy.”

When the day came, Scott was so excited to go back into pants. But when he went to his room to dress, all he saw laid out was a light blue party dress.

“Blue for boys,” his mom said with a laugh. “Well you’d do no good for Miss Francine’s booth dressed in pants, now would you? Now let’s get dressed.”

First came something new to the ensemble, white tights. After sliding them up his legs, came the matching panties of course. Light blue, with three layers of white frilly lace going all the way around them. Definitely not something a boy would wear at any age. After the bra, came his petticoats. All three were made of stiff white netting, to stick straight out and certainly lift up in the wind.

Finally came the dress. Despite the color, this was anything but for boys. At the top was a white color with a thin blue trimming around it. Below was glass silk to see through the top of the chest, before reaching the bodice which was white satin with a blue flower on the top. On each side at about the collar bone, there was a row of white lace going down from the shoulder to the waist. The side panels were light blue, as well as the full skirt, whose bottom was edged in white lace as well. Finally, the white puff ball sleeves also had white lace edging.

Mom put lacy white socks and black Mary Janes on his feet, as well as white satin gloves on his hands. She put a matching blue hairband on his head that had a blue flower on top. Scott looked in the mirror and saw he was dressed like a 6 year old girl going to a tea party. What’s worse, the petticoats lifted up his dress enough to give off just a glimpse of his panties from the back when he was standing straight up.

Hopefully no one would pay attention to the booth enough to recognize Scott, that was his only hope. After doing his makeup, she also handed him a matching blue handbag.

“I’ve noticed the stains you’ve been leaving in your panties, so I bought an extra matching pair of all your panties,” his mom said. “Look inside, you’ll find this dress’s pair already packed for you. If you get too excited and have an accident, just tell Miss Francine and she’ll let you go to the bathroom to change. Now, for today you have a new greeting. When any customer walks up to the booth, along with your curtsey you must say ‘I’m Scott, and I love wearing dresses and panties! How may I serve you?’”

Scott went to the car with his mom, but his sister was already in the front seat. Scott climbed in back, instinctively smoothing out his dress as we got in. “We just need to pick up Jessie & Rachel on the way!”

Oh no, his sister’s friends! He was lost in panic the whole way to their house, so when they pulled up in the driveway Scott had no idea what to do. “We’ve got to go in, Jessie’s still getting ready.”

When they walked in the house, he saw Jessie, fully ready, waiting in the living room with Rachel as well as Jessie’s mom.

“You weren’t kidding, your brother really is a huge sissy!” Jessie said to my sister.

“Go ahead Scott, what do we do to greet people?”

Scott curtsied to the room of giggling girls, repeating his lines, “I’m Scott, and I love wearing dresses and panties! How may I serve you?”

His mom added, “Well since you asked, let’s start with a twirl for my friends.”

Scott twirled, causing his skirt to float up and reveal his panties. “Ohh wow, he’s even wearing panties that match his dress!” Jessie, Rachel, and even Jessie’s mom could no longer hold back and rushed over for a closer look.

“Your brother is so precious! Though I guess he’s not really your brother, is he? A real boy wouldn’t twirl in dresses.” As the girls fussed with his dress and petticoats, Scott could feel himself start to grow excited in his panties. And after a while, his sister came over to join in.

“Don’t forget to get a closer look at his panties,” she said before lifting up his skirt and petticoats. He hoped the bulge wasn’t too noticeable beneath the frills, but one of the girls quickly shouted, “Ohh my god, your brother must really love this, he has a boner!”

“That only means he’s excited to show you his pretty clothes, he gets them all the time actually. In fact, he carries an extra pair of panties in his purse just in case he gets a little too excited and creams,” his mom said. “But let’s not put them to use so early, we better get going.” Scott rode in back with his sister’s two friends to the fair. But he took no notice to their comments, as he was distracted by the realization that he was now going to be seen by the whole town dressed like a sissy girl.

They all walked together to Miss Francine’s booth, getting plenty of stares and giggles as they did, but luckily none by anyone he knew. When they arrived, Miss Francine was waiting. The booth was the only pink tent at the whole fair, making it stand out among the white tents elsewhere. There was a wooden sign in front, which featured the store’s name along with a picture of Scott in one of his other dresses. Was he the new logo? There were also two dresses on display. The first was a red gingham pinafore dress with a white blouse underneath and pushed out by layers of petticoats. The other was a pink ballet tutu. Both looked appropriate for a six-year old girl, but were about Scott’s size.

“I see you notice your two new outfits for the school year,” Miss Francine said as Scott looked her way in confusion. “Well, they could be. For now, you will have the option to go back to boy clothes during school if you want. But your mom had these prepared if you begin to step out of line at all this summer. You’ll notice the first dress is in your school’s colors. We’ve already gotten it approved by your principal to be your new uniform, along with frilly panties to match of course. Your mom already ordered 5 of them, one for each day so you’re all set. But don’t worry, you’ll change back into your other pretty dresses each day when you get back home. And the tutu would be your new gym uniform when you’re learning dance in class. When it’s time for sports, we’re designing you a cheerleader uniform to wear as you cheer on your classmates. Can’t have a sissy like you actually playing!”

Scott couldn’t believe it. There was a chance he would have to keep dressing up during school? He would have to do everything he could to stay in line. “Now for today, you’ll be working to call attention to the store’s booth, as well as posing for photos to get the store some social media publicity. And it looks like we have our first customers.”

Scott turned to see a group of his classmates walking right towards him.

“Is that a boy in that dress up there?”

“It is… Hey, I know that kid. He was in my English class.”

“Ohh yeah, I think his name is Scott. Wow, how pathetic! Let’s go have a look.”

Scott was now revealed as a sissy to his high school classmates. It wouldn’t be long until the whole school knew. But he couldn’t risk having this carry on beyond the summer. So, as they approached, he cursed and said “I’m Scott, and I love wearing dresses and panties! How may I serve you?”

It was going to be a long day. The summer may never end.

Description
When Scott learned he was going to his hometown’s summer fair, he pleaded nonstop for his mom to let him go in boy clothes. All of his classmates would be there, along with the rest of the town.After a while, she relented. “Fine Scott, I’ll dress you like a boy.”

When the day came, Scott was so excited to go back into pants. But when he went to his room to dress, all he saw laid out was a light blue party dress.

“Blue for boys,” his mom said with a laugh. “Well you’d do no good for Miss Francine’s booth dressed in pants, now would you? Now let’s get dressed.”

First came something new to the ensemble, white tights. After sliding them up his legs, came the matching panties of course. Light blue, with three layers of white frilly lace going all the way around them. Definitely not something a boy would wear at any age. After the bra, came his petticoats. All three were made of stiff white netting, to stick straight out and certainly lift up in the wind.

Finally came the dress. Despite the color, this was anything but for boys. At the top was a white color with a thin blue trimming around it. Below was glass silk to see through the top of the chest, before reaching the bodice which was white satin with a blue flower on the top. On each side at about the collar bone, there was a row of white lace going down from the shoulder to the waist. The side panels were light blue, as well as the full skirt, whose bottom was edged in white lace as well. Finally, the white puff ball sleeves also had white lace edging.

Mom put lacy white socks and black Mary Janes on his feet, as well as white satin gloves on his hands. She put a matching blue hairband on his head that had a blue flower on top. Scott looked in the mirror and saw he was dressed like a 6 year old girl going to a tea party. What’s worse, the petticoats lifted up his dress enough to give off just a glimpse of his panties from the back when he was standing straight up.

Hopefully no one would pay attention to the booth enough to recognize Scott, that was his only hope. After doing his makeup, she also handed him a matching blue handbag.

“I’ve noticed the stains you’ve been leaving in your panties, so I bought an extra matching pair of all your panties,” his mom said. “Look inside, you’ll find this dress’s pair already packed for you. If you get too excited and have an accident, just tell Miss Francine and she’ll let you go to the bathroom to change. Now, for today you have a new greeting. When any customer walks up to the booth, along with your curtsey you must say ‘I’m Scott, and I love wearing dresses and panties! How may I serve you?’”

Scott went to the car with his mom, but his sister was already in the front seat. Scott climbed in back, instinctively smoothing out his dress as we got in. “We just need to pick up Jessie & Rachel on the way!”

Oh no, his sister’s friends! He was lost in panic the whole way to their house, so when they pulled up in the driveway Scott had no idea what to do. “We’ve got to go in, Jessie’s still getting ready.”

When they walked in the house, he saw Jessie, fully ready, waiting in the living room with Rachel as well as Jessie’s mom.

“You weren’t kidding, your brother really is a huge sissy!” Jessie said to my sister.

“Go ahead Scott, what do we do to greet people?”

Scott curtsied to the room of giggling girls, repeating his lines, “I’m Scott, and I love wearing dresses and panties! How may I serve you?”

His mom added, “Well since you asked, let’s start with a twirl for my friends.”

Scott twirled, causing his skirt to float up and reveal his panties. “Ohh wow, he’s even wearing panties that match his dress!” Jessie, Rachel, and even Jessie’s mom could no longer hold back and rushed over for a closer look.

“Your brother is so precious! Though I guess he’s not really your brother, is he? A real boy wouldn’t twirl in dresses.” As the girls fussed with his dress and petticoats, Scott could feel himself start to grow excited in his panties. And after a while, his sister came over to join in.

“Don’t forget to get a closer look at his panties,” she said before lifting up his skirt and petticoats. He hoped the bulge wasn’t too noticeable beneath the frills, but one of the girls quickly shouted, “Ohh my god, your brother must really love this, he has a boner!”

“That only means he’s excited to show you his pretty clothes, he gets them all the time actually. In fact, he carries an extra pair of panties in his purse just in case he gets a little too excited and creams,” his mom said. “But let’s not put them to use so early, we better get going.” Scott rode in back with his sister’s two friends to the fair. But he took no notice to their comments, as he was distracted by the realization that he was now going to be seen by the whole town dressed like a sissy girl.

They all walked together to Miss Francine’s booth, getting plenty of stares and giggles as they did, but luckily none by anyone he knew. When they arrived, Miss Francine was waiting. The booth was the only pink tent at the whole fair, making it stand out among the white tents elsewhere. There was a wooden sign in front, which featured the store’s name along with a picture of Scott in one of his other dresses. Was he the new logo? There were also two dresses on display. The first was a red gingham pinafore dress with a white blouse underneath and pushed out by layers of petticoats. The other was a pink ballet tutu. Both looked appropriate for a six-year old girl, but were about Scott’s size.

“I see you notice your two new outfits for the school year,” Miss Francine said as Scott looked her way in confusion. “Well, they could be. For now, you will have the option to go back to boy clothes during school if you want. But your mom had these prepared if you begin to step out of line at all this summer. You’ll notice the first dress is in your school’s colors. We’ve already gotten it approved by your principal to be your new uniform, along with frilly panties to match of course. Your mom already ordered 5 of them, one for each day so you’re all set. But don’t worry, you’ll change back into your other pretty dresses each day when you get back home. And the tutu would be your new gym uniform when you’re learning dance in class. When it’s time for sports, we’re designing you a cheerleader uniform to wear as you cheer on your classmates. Can’t have a sissy like you actually playing!”

Scott couldn’t believe it. There was a chance he would have to keep dressing up during school? He would have to do everything he could to stay in line. “Now for today, you’ll be working to call attention to the store’s booth, as well as posing for photos to get the store some social media publicity. And it looks like we have our first customers.”

Scott turned to see a group of his classmates walking right towards him.

“Is that a boy in that dress up there?”

“It is… Hey, I know that kid. He was in my English class.”

“Ohh yeah, I think his name is Scott. Wow, how pathetic! Let’s go have a look.”

Scott was now revealed as a sissy to his high school classmates. It wouldn’t be long until the whole school knew. But he couldn’t risk having this carry on beyond the summer. So, as they approached, he cursed and said “I’m Scott, and I love wearing dresses and panties! How may I serve you?”

It was going to be a long day. The summer may never end.