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Will his mom really let girls from his class over to see him?
I sure hope so!

NudeBaG wrote: Sun Mar 01, 2026 11:53 am Will his mom really let girls from his class over to see him?
I sure hope do!

Good idea. I think she'll invite his crush over.

lovestosplooge wrote: Sun Mar 01, 2026 12:16 pm

NudeBaG wrote: Sun Mar 01, 2026 11:53 am Will his mom really let girls from his class over to see him?
I sure hope do!

Good idea. I think she'll invite his crush over.

Oh gah!
At 11, that should be humiliating for him, but thrilling for his crush
And the mom’s friend’s daughter is 8?

Day 2: An Embarrassing School Day

Lauren was driving Oliver to school. His seat belt was the only thing covering his nude body, which felt weird pressed bare against the car seat. The boy felt completely exposed.

"You really have my clothes, Mom? You're really not going to just send me out there naked?" Oliver was paranoid.

"I promise I'm not, Oliver. I don't want you arrested. I have your clothes in a bag in the backseat."

They pulled up to the school. Oliver could see all his schoolmates walking up to the building. He was glad the windows of the car were tinted, but still scared someone might see.

"Okay, we're here. Clothes. Clothes!" Oliver pleaded.

Lauren reached into the backseat and grabbed a bag. She handed it to the boy. Inside he saw pink sneakers, a pink shirt, and bright yellow shorts. Very short shorts.

"What are these?! These aren't my clothes!"

"I found them at a thrift store. Don't you like them?"

"They're for girls!" He looked closer at the shirt. "Look, there's Dora the Explorer on the shirt! This is a girl's shirt! I can't wear this!"

"Well I still want you humiliated. It wouldn't be a very fair deal if you could just wear your normal clothes at school, would it?"

Oliver quickly put on the shorts anyway, just in case anyone could see through the car window. The bottom of his shorts were inches above his knees, and two or three sizes too small.

"Mom, why are you doing this to me?" He started tearing up again.

"Oliver, you need to prove you don't want to go to that academy. I can drive you home and give you your normal clothes instead, but that means you're going to that academy until you're 18."

The boy thought about it. This was too much. Lauren started getting worried that he may actually quit, so didn't give him the option. "Okay, out! Put your shirt and shoes on and get out in 10 seconds or I'm dragging you out as you are!"

The boy scrambled to put everything on, and then exited the car. He didn't care. He just wanted away from the mean woman.

That lunchtime, Lauren got a phone call from the school.

"Hi, Lauren? It's Oliver's teacher, Ms Sutton. I just wanted to call about Oliver's attire today."

"Yes, what is it?"

"It's caused a lot of schoolyard bullying. The kids have been teasing him all day. He told me it wasn't his decision to wear this."

Lauren became nervous. "Oh... Yeah. I just feel he should wear something more feminine. You know, make him respect girls fashion more. Show him it's okay to not conform to gender roles."

"Oh, I completely understand and respect that. But the boy is a mess. I can stop the teasing during class, but the attacks he's getting from all the other students during lunchtime is something else. You're fine to dress him how you like, but I thought you should know."

"Okay. Thanks, Ms Sutton."

That afternoon, Lauren picked Oliver up from school. As soon as he got in the car, she noticed the boy looked completely miserable.

"How was your day, sweetie?"

"The worst day ever. Let's just go home."

"First you have to take those clothes off. You remember the rules?"

The boy kicked off his shoes, removed his shirt, and then glanced out the window to make sure nobody was around before taking off his shorts.

"Okay. Let's just go." He pouted.

Lauren wondered whether she should let him wear his normal clothes the next day. Or maybe... she thought, she should make him wear something even more humiliating?

Wow! Something even more embarrassing! I can't wait to see this, if she goes ahead with it. I suppose a skirt would be more embarrassing, especially if he's not allowed nice panties to go with it! But I'm sure you have some great plans ..........

Wow. Poor Oliver is in for an even more humiliating day!

At least in school he’s allowed to/has to wear SOMETHING.
Hopefully, no girls show up uninvited to his house, where he’s not allowed to dress at all

lovestosplooge wrote: Sun Mar 01, 2026 5:59 am Day 1: It Begins

"Bring your daughter too. How old is she now?"

"She's eight. And if I remember myself correctly at her age, this should definitely be fun for her."

The two women laughed. "I will be busy with things the next few days, but maybe Wednesday after they've finished school? Bring her over then!"

"Wednesday it is!"

I can’t wait for Wednesday

I did just realize with how enjoyable this story is so far, the daily updates are going to be a mixed bag.

On one hand, assuming everything goes right, we can expect an update every day
On the other, after reading that update, we are forced to wait until tomorrow
I’m not Jewish, but this feels like what selfish kids at Hanukkah must endure lol

Thanks for all the feedback. It helps keep me writing.

Day 3: Another Embarrassing School Day

Oliver didn't want to go to school. He laid on his mattress, face down, crying. Lauren walked into the room.

"Come on, Oliver. You'll be late."

"Please. I can't go. Everyone was making fun of me for what I wore yesterday. The boys and the girls! Why do this to me, mom? I really don't want to go to the academy, haven't I proven that already?"

"We had a deal. 30 days of this. Do you quit? You have it really easy getting something to wear when you're at school. And yet you still complain."

"I can't go to school today. I'm sick."

"No you're not, Oliver. Get to the car in 5 minutes or the deal is off and you're going to the academy instead."

The sullen naked boy sat in the passenger seat with his head leaning against the window. He was close to giving up and just deciding to go to the academy. Fortunately, his mom was aware this could happen, and had a plan.

They drove up to the school, and his mom handed him the bag. He opened it up to find the pink sneakers and... a dress! A pink flowery dress!

"Mom. No. You're joking. I can't wear this!"

"Yes you can."

"No, they'll kill me! I can't do it. I quit, and I'm going to the academy."

"Oliver, you either wear the dress or..." She held up her phone to show photos of the boy naked around the house from the previous few days. She had been taking photos of him secretly the entire time. "These photos get sent to every single person in your school. So they can either see you in a dress, or they can see you naked."

She had checkmated him. "Mom, you can't!"

"I can. So this is now how it works. If you don't do what I say from now on, not only are you going to the academy, but everyone in the school is going to see these photos."

She started swiping through them. Him naked eating breakfast, playing outdoors, sitting on the couch. If his penis wasn't visible in a photo, his butt was.

The car door opened, and out stepped Oliver wearing the dress. Lauren beeped the horn twice to get everybody's attention before driving away.

As Oliver walked through the school halls towards his locker, all the kids either grinned, snickered, or openly laughed at him. He wanted to die.

He opened his locker, threw in his bag, and ran towards the boys bathroom. He locked himself in a stall and cried. He couldn't go out there to class. This was the worst day of his life. How could his mom be so mean?

He heard the bell for class to start. He thought about just sitting there all day, hiding, but realized if he didn't show up for class, his mom would get a call. Would she send out the photos if she found out he was skipping school? He felt sick.

He walked into class. Everyone started laughing when they saw him. "Settle down, children. No judgements, please." His teacher ordered.

Oliver took his usual seat in the front row. He had to sit with his legs closed because the dress was so short. There was snickering throughout the first few hours, and a paper ball thrown at his head, but he managed to get through the morning without crying.

The bell rang for lunch, and everyone started leaving. Oliver stayed at his desk. A bully "accidentally" barged into him as he was leaving.

When all the kids were gone, Oliver asked his teacher, "Can I please just stay here for lunch?"

"Sorry, Oliver. I'll be going to the teacher's lounge for lunch. I can't leave students alone unattended."

"Oh..."

While his teacher Ms Sutton felt bad for the kid, she did think he looked cute in the dress. She couldn't help but notice he wasn't wearing underwear during the times he had forgotten to close his legs, which had made her morning better. If his mom was going to keep forcing him to wear things like this, she was starting to have less of a problem with it.

I love when teachers are on board with nudity.
But I love when female classmates are on board even more