Tutoring Chelsea (Updated with chapter 3, Oct 18)

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Tutoring Chelsea (Updated with chapter 3, Oct 18)

Post by lovestosplooge »

Tutoring Chelsea

Chapter 1

Sammy couldn't believe it. He was actually in Chelsea's room! He was in the grade above her, and had been crushing on her since they met at the start of the year. Her mom put a request in at the school for a math tutor, and Sammy jumped at the opportunity. 25 dollars an hour, but he honestly would've done it for free.

He sat at her desk, going over her math problems for that week's homework, while Chelsea laid on her bed, scrolling on her phone. While she thought Sammy was kind of cute, he was a complete nerd, so she didn't have that much interest in getting to know him. And she especially didn't have an interest in math.

"So the good news is all of these math questions use the same rule. Do you know what rule that is?" Sammy asked.
"Uh... I don't know. Can't you just do it for me?" The girl replied, fixated on her phone.

Sammy sighed. He wished she actually wanted to learn, maybe actually sit at the desk with him.

"I've got to go grab a drink. I'll be back." Chelsea said, jumping off his bed.
"Okay, no problem."

Chelsea left the room. Sammy knew she wouldn't be back quickly, since she had absolutely no interest in learning. He stood up to explore. There were posters on boys all over the walls; celebrities that he didn't know, not having much of an interest in mainstream pop culture. In the corner of the room was a chest of drawers. He glanced behind him to make sure she was really gone, and then opened the top drawer. Socks and underwear! He pulled out his phone and took a photo of the contents, and sent it to his best friend, Max.

"Guess whose underwear drawer? 😂" Sammy captioned the photo.
Max replied almost immediately. "OMG!! Steal a pair! I NEED! lmao".

Sammy laughed. He wasn't as perverted as Max, but still enjoyed his antics. He quickly snatched a pair of her panties to place in his bag, figuring she wouldn't notice they were gone.

"AHEM!"

Sammy turned around. Oh crap. Chelsea's mother was standing in the doorway.

"What did I just see you do?"
"I... uh..."
"Do you have no respect for boundaries? I'm paying you 25 dollars to do something like that?"
"Sorry, I was just... I'll put them back." The humiliated and scared boy placed the underwear back in the drawer. "Please don't tell anyone. I can give you your money back and work for free."
Chelsea's mom just stared at the nervous boy, letting the tension sit in the air for a while. Then she finally spoke. "Leave now. I'll tell Chelsea you were sick and had to go. But I want to see you back here tomorrow at 4 PM to discuss this."

Sammy nodded, apologizing repeatedly as he grabbed his bag and quickly made his way out of the house. He was horrified.

That night, Sammy couldn't sleep. Would Chelsea's mom have told Chelsea what he did? Would he be kicked off the tutoring team? Would he be expelled?! So many scenarios and thoughts kept repeating in his mind. If she told, everyone would consider him a pervert. He felt sick, and took the next day off from school.

3:30 PM rolled around, and Sammy finally got out of bed. He had to go visit Chelsea's mom to discuss what happened, like she had told him. He got on his bike and rode to her house. She let him inside and brought him to the living room. Their house was a mansion, which he envied, and the living room was huge.

"Sit." She ordered. Sammy sat down on the couch. "What you did was perverted, but I've decided not to tell anyone if you've truly learned your lesson."
"I have. I have learned my lesson!"
"No you haven't, but you will. Chelsea is currently at her friend's house. She'll be home in a couple of hours, so it's just you and me here until then. I want you to clean every inch of this living room. Vacuum the floors, wipe the cabinets, scrub the walls. As soon as she gets home, you can leave, and then I'll consider your lesson learned."
"That sounds fair."
"But there's one more catch. You're to do it completed naked."
Sammy couldn't believe what he had heard. "You... what?"
"If you're going to objectify my daughter, I'm going to objectify you. Do the chores naked or I'll tell everyone about what you did. Your parents, the school, and of course, Chelsea."
"Why would you want to see me naked?" Sammy asked, confused.
"I don't WANT to. Trust me, I get no pleasure out of this. This is just the only way to make you feel objectified, so you truly know how it feels when you decide to objectify a poor innocent girl."

This was Sammy's nightmare come to life. He couldn't be naked in front of someone else, especially a woman.

"I can't do that. I'll do the chores, but I can't be naked. Please, I can't do that."
"Then I'll call your parents right now and tell them what you did." She pulled out her phone and began to dial.
"Wait!"

Chelsea's mom stopped and stared at the boy, waiting to hear what he had to say.

"Please, please, if I do this, promise that's it? You'll forget everything that happened?"
"I promise. Now take off the clothes."
"And you're the only one in the house? Really?"
"Really, Sammy. Nobody else will see you, just me. Now take them off."

Sammy was completely red, with tears in his eyes. This whole situation was too much. He kicked off his shoes and socks, then slid off his shirt. As he did, Chelsea's mom stared at him with her arms crossed. "Faster, Sammy."

The boy was down to his shorts. "There's nothing else I can do?"
"Take them off or I dial your parents right now. No more stalling."

Sammy removed his shorts. He covered the front of his crotch, even though he was wearing underwear.

"Those too."
"Please..."
"Okay, that does it."

Chelsea's mom dialled his parents and started speaking. "Hi, is this Sammy's mom?"

Sammy immediately dropped his underwear to the ground. The sadistic housewife grinned. "Just wanted to say thanks for having Sammy tutor my daughter yesterday. He was great!"

Soon, the naked boy was vacuuming the living room. Chelsea's mom sat on the couch, half watching him, and half scrolling on her phone. She had taken his clothes to a secure spot, and told Sammy she would return them before her daughter came home.

Meanwhile, Sammy was trying not to think about the situation. His mind was anywhere but there. What scared him the most was Chelsea coming home without his clothes yet being returned. But her mom couldn't be that mean, right?

To be continued...
Last edited by lovestosplooge on Sat Oct 18, 2025 1:23 am, edited 2 times in total.
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Re: Tutoring Chelsea

Post by TeenFan »

I assume Sammy and Chelsea are in High School. He is still riding a bike, so probably isn't older than sixteen.
If you intend for them to be younger, I'd like to know that.

Is the mom hot?
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Re: Tutoring Chelsea

Post by lovestosplooge »

TeenFan wrote: Wed Oct 15, 2025 4:05 pm I assume Sammy and Chelsea are in High School. He is still riding a bike, so probably isn't older than sixteen.
If you intend for them to be younger, I'd like to know that.

Is the mom hot?
I've answered these questions in chapter 2 of 3 below.

Chapter 2

Sammy stood on his tiptoes to reach the top of the cabinet, wiping away the dust. Chelsea's mom thought it was an adorable sight, the naked boy nervously working away.

Suddenly she received a text from her 13-year-old daughter. "I'll be home in 5 minutes mom! ❤️"

The mother grinned, thinking about whether she should get Sammy's clothes. While it would be hilarious to have Chelsea come home to find her schoolmate completely naked, how was she even going to explain why he was naked in the house to begin with?

She still wanted to have some fun though.

Five minutes later, Sammy heard the front door open. He turned to Chelsea's mom with a look of pure shock. "Is she home?!" He mouthed silently, half due to fright and half because he didn't want Chelsea to hear.

"Mooom, what's for dinner?" Chelsea called out. That had answered it for Sammy.

The distraught boy dropped his cleaning supplies to the floor and shut the sliding doors to the living room. He went from pale white to a humiliated red in seconds. "Please, don't do this to me. Get me my clothes." he begged. He could hear Chelsea walking towards the room.

"Behind that chair. She won't see you there." Chelsea's mom said, pointing to the small sofa in the corner of the room.

Sammy sprinted to the corner and ducked down behind the chair, just before Chelsea opened the door. "Mom, I want lasagna for dinner. Do we have lasagna?"

"Yes, I can bake you some. Why don't you have a shower and I'll start getting it ready?"
"Okay! Thank you!"

Chelsea left the room, and her mom walked over to the cowering Sammy. "She's having her shower, so now would be your only opportunity to get dressed and leave. You've definitely learned your lesson, I think."

"So where's my clothes?" Sammy pleaded.

"I left them in Chelsea's room. You better hurry and grab them before she gets out of the shower."

"Chelsea's room? Where in her room? Can't you get them for me?"

"I have no obligation to do that. I think I left your clothes in that underwear drawer of hers you were so obsessed with."

As good looking as she was, Sammy really hated this woman. He slowly crept out of the living room and could hear the shower running down the hall. The coast seemed clear. He sprinted towards her room, opened the door and made a dash for the drawers, when thud! In his haste, he had tripped over Chelsea's school bag.

Sammy opened his eyes. How long had he been out? His head hurt as he looked around the room, trying to remember where he was and why he was naked. It all quickly came back to him, and he was horrified to realize he could no longer hear the shower running! Chelsea could be back in the room any second.

He stood up, realizing he had not only injured his head, but his leg too. It hurt to walk, so he limped over to the drawers and opened the top one.

...His clothes weren't there! Chelsea's mom had lied to him! He frantically checked every other drawer.

He started to hear little footsteps walking towards the room. Chelsea!

The naked boy needed a place to hide, so he dived under the bed. There was enough room under there, but he knew he couldn't afford to make a sound.

Chelsea entered the room. She was wearing her pajamas, with a hair towel around her head. Trapped in his crush's room completely naked. This was a nightmare.
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Re: Tutoring Chelsea

Post by MaireadM »

Love the scenario.
Hope there are more twists
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Re: Tutoring Chelsea

Post by little_kitetail »

I like this. Leaving off with a real sense of tension with him hiding naked in the girl's room.
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Re: Tutoring Chelsea

Post by Trundle »

Really fantastic start here!

Very well written, cannot wait to see what happens next. I hope the story lasts for more than 3 chapters, really enjoying this.
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Re: Tutoring Chelsea

Post by lovestosplooge »

Thanks so much for the feedback. I didn't want this to drag out forever, so I gave myself a three chapter limit, but I'm finding there is no way to wrap it up so quickly, so yes there will be more. I hope you enjoy.

Chapter 3

Sammy was laying on his tummy, hands over his mouth so he wouldn't make a sound. He could see Chelsea's legs standing at her desk, and deduced that she was probably doing some kind of girly skin treatment in the mirror or something.

If he was caught in this predicament, his life would be over. This was a million times worse than merely being caught grabbing some panties from her drawer. He just wished he was back at home in his bed. He had read about people manifesting things they desire, so he closed his eyes and wished with all his might that he could just go back in time to before this mess started. He slowly opened his eyes, hoping to be in his bed at home, but of course that wasn't the case.

Chelsea sat on the bed and started talking. "Hi!"

Sammy's heart froze. Then he realized she was talking on the phone to one of her friends.

"Yeah, I'm just waiting for my mom to cook dinner. ...Oh my god, yes, I can't wait to go to Tommy's party this weekend, it's going to be so good!"

Even though he couldn't hear the other side of the conversation, it was interesting to hear Chelsea's private phone call. He wasn't in the "cool" group, and to hear about everything she talked about was a different world to him. He could count on one hand the amount of parties he went to during his entire life, yet Chelsea was listing off dozens of them like they were an every day event.

Chelsea being on the phone made him realize something else. His phone! It was in his pocket when he removed his shorts. If only he had that so he could call his best friend, Max, for help. Maybe get him to come over with some clothes, and then distract Chelsea while he makes an escape. Max definitely owed him, he thought. It was his stupid idea to grab Chelsea's panties in the first place.

Suddenly the naked boy heard something interesting from the conversation Chelsea was having. "Yeah, I have a tutor now. Do you know Sammy? The boy in the grade above us. .................He's kind of cute, I guess. But ugh, he's such a creep! The way he was staring at me when he was here yesterday made me so uncomfortable. I'm going to tell my mom I want a different tutor, I think."

Sammy was crushed. But if she thought he was a creep now, he could only imagine what she'd think if she caught him naked under her bed. He had to get out of there.

"Chelsea, dinner's ready! Eat it here at the table, please." Her mom called out.
"Okay, I've gotta go, we're having lasagna! I'll talk to you at school tomorrow." Chelsea ran out of the room.

Sammy figured he'd have at least five minutes before she finished her dinner. He crawled out from under the bed and saw her phone laying by her pillow. If he could find Max's instagram or facebook or something, he could call him using her phone. He grabbed it and tried to get in. It needed a password or a face ID.

He turned and saw a framed photo of her face sitting on her desk. Holy shit, could that work? He aimed the phone at the photo and... YES! The phone unlocked.

He went to the messenger app. She had so many unread messages from boys. He typed Max's name and even it came up as one of her unread messages! He clicked the conversation and cringed reading through it:

Max says:
Hi Chels
Max says:
I'm in the grade above you, sorry for the random add haha
Max says:
You're hotttt.......

All left on unread. Max was such a dork. He clicked "call" and Max picked up.

"Hello? Chelsea?!" Max was shocked.
"No, you idiot." Sammy whispered. "I'm on Chelsea's phone. I'm stuck in her room. I need you to bring me some clothes and distract Chelsea and her mom at the front door while I sneak out the back door."
"Huh? What are you talking about?" Max replied.
"Dude. Just bring a bag with some clothes to Chelsea's house! Knock on the front door and keep them there for like 5 minutes. Can you do that?"
"Maybe. What in it for me?" Max was the worst friend. "Did you ever get those panties from her? Get me those and I'll do it."

Sammy ended the call short in anger. Once he was out of this mess, he was going to get a new best friend, he told himself. He tried to think of someone else he could call, or anything else he could do.

Time was running out and Chelsea would be back soon. He was getting more and more nervous and his thoughts weren't clear. He just needed to focus.

He opened the wardrobe. He needed to find something that could fit him. That way if Chelsea did catch him, at least he was wearing something. It was all dresses and shirts that were way too small. He snatched a pair of shorts, put his leg into them, but could barely pull them up. Chelsea was too petite for anything to fit him. He kicked the pants off in anger.

Suddenly Chelsea's phone started ringing. He looked at the screen. It was Max! He was calling back, and the call notification was loud.

Sammy heard Chelsea's mom call out. "Chelsea, where are you going?"
"I left my phone in my room. I can hear someone calling!" He heard Chelsea say as she ran towards the room.
Oh, SHIT, Sammy thought. Damn it, Max!

Chelsea burst through the doorway, then paused in shock. There was Sammy, completely naked, standing by her wardrobe, holding her phone.

Chelsea screamed.

To be continued...
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Re: Tutoring Chelsea (Updated with chapter 3, Oct 18)

Post by TeenFan »

Poor Sammy is SOOOO Screwed.
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Re: Tutoring Chelsea (Updated with chapter 3, Oct 18)

Post by DrWhoFanJ »

TeenFan wrote: Sat Oct 18, 2025 3:11 am Poor Sammy is SOOOO Screwed.
And not in the fun way!
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Re: Tutoring Chelsea (Updated with chapter 3, Oct 18)

Post by Trundle »

This is fantastic.

You're very good at quickly establishing an interesting premise and then having fun with it.

Really enjoying this. I think this could be a story that goes on a while but I understand if you like short and sweet stories.

Can't wait for the next update!
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