NudeBaG wrote: Fri Mar 06, 2026 2:04 pm
Fantastic set up for things to cum!
Already loving Lucy as well!
Oliver may be getting bullied, but he seems to be growing in popularity among the young girls
Keep up the great work!
It’s a wonderful cast of characters you’re building.
Just a pity we have to wait until tomorrow lol
I'm loving Lucy too. This was almost going to be a one time character. He would get an erection at lunch, she would call him a pervert, and that would be the end.
But I want her to stick around.
SO glad you went a different route!
For some reason, I’m hoping any full exposure at school is put off for a bit yet.
I’m liking the ‘controlled’ embarrassment at home for the time being.
Plus, with so many chapters to go, it might be good to have something to build to.
Lots of fun possibilities with this set up!
Keep it up!
Want to join in and say how much I love the Lucy character and I'm so glad she's not a one off. Cannot wait for her to be more in the story and this potential play date sounds very exciting.
If it's a play date at their house Oliver will be in a very tough position. Will he be made to be naked still or will Lauren allow him to wear something? Cannot wait to find out.
Oliver jerking in the bathrooms, he got away with it this time but will he continute to get away with it?
All in all, absolutely loving this story. So well written and so many possibilities for embarrassing poor Oliver!
Saturday morning. Oliver woke up thinking of Lucy. His first time masturbating yesterday was one of the best feelings of his life, and he wanted to do it again before he had to get out of bed.
He visualized Lucy's behind walking away from him in the playground. He imagined what she looked like without those shorts. What kind of underwear did she wear?
He started stroking.
Suddenly his bedroom door swung open. He quickly let go of his penis and flipped his body so he was laying on his front.
It was his mom. "I have errands to do today, so wake up and come eat breakfast."
He waited for his boner to go down, and then walked out to the kitchen table. He started eating his bacon and eggs. His mom sat at the table too, doing something on her laptop.
"Oh, Kathy Swanson replied to my Facebook message!" Lauren said. "Her daughter Lucy is in the grade below you. Do you know her?" She grinned.
"Um... I think so."
"You think so? Your teacher told me she's your new best friend."
Oliver hated how his mom knew this. "I just talked to her at lunch yesterday. That's all."
"Well her mom and I are getting coffee today. I'll put in a good word for you." She winked.
Oliver started turning pink from embarrassment.
Lauren locked her computer and grabbed her purse. "I'll be out all day. I don't want you having fun when I'm gone, so I'm taking the TV remote. Instead there's a pile of dirty dishes in the sink for you to work on. When you're done with those, I want your room cleaned. There's toys and dust everywhere."
"Okay, mom."
After she left, Oliver grabbed his mom's laptop. He would get to the chores soon.
The laptop had a password. He clicked the "hint" button: "My favorite show". He knew this! He typed "bigbrother".
Incorrect.
He typed "bigbrother7" due to his mom's favorite number.
Success!
Oliver wasn't allowed a laptop or a phone. He was allowed to use his mom's laptop for homework with her supervision. This was the first time he had some privacy on the computer, and he had a goal in mind after their conversation about Lucy.
He went to the browser and typed Facebook. She was still logged in. He clicked on Lucy's mom's profile. He started getting hard over the thought of how naughty he was being.
Photos of Lucy! It looked like hundreds of them. The horny boy started clicking through: Lucy at Christmas, Lucy dressed up as a witch for Halloween, Lucy on her first day of 4th grade. She looked cute in all of them, but soon he found a photo that almost made him explode: Lucy on vacation in Orlando, wearing a two-piece swimsuit. She was standing with her family on the beach, smiling adorably at the camera. The boy began stroking, staring at the photo. The only thing covering her was a pair of small blue bikini bottoms and blue bikini top. He admired her bare legs, belly, even her shoulders.
Oliver's orgasm was his most intense one yet.
He closed the browser and locked the laptop.
At lunchtime, Lauren was at a cafe having coffee with Lucy's mom.
"So would you like to bring Lucy over tomorrow afternoon? Oliver would love to see her!"
"I'll check with her, but I'm sure she'll say yes. I'm so glad she can be a friend for your Oliver." Lucy's mom replied.
Another great update that sets things up for the near future.
It was actually nice to see Oliver have something of a nice day, he was naked and had to do a load of chores but at least he wasn't embarrassed in front of everyone and he got to enjoy some "personal" time
I bet it's not so nice for long though. Lauren surely has some evil plans for him
Really fun as always, looking forward to this play date!
Lauren had been brainstorming since Friday how to humiliate Oliver on his play date with Lucy. Should she keep him naked? Should she not tell him in advance Lucy was coming over? Should she feed him a blue pill? But last night, she discovered something that would let her totally crush the boy.
The mother and son were having lunch at the kitchen table when she broke the news.
"Oliver, your friend Lucy is coming over today."
"What?!"
"Don't worry, I'm going to let you wear clothes. I'll get a dress for you to wear. I think it's good you've made a friend and don't want to embarrass you by having you be naked."
"She's really coming over? Why?"
"I suggested it with her mom yesterday at lunch. She wants to come over, which means she must like you."
Oliver nodded and started playing with his food. "Thanks for letting me wear clothes."
"Of course, honey!"
Suddenly there was a knock at the door. Oliver gasped.
"Where's my dress?!"
"Don't worry, that's not her yet. I've asked Ivy to come over first."
Lauren let Courtney and Ivy into the house. Ivy was holding a makeup bag. She excitedly ran up to the naked boy who was still eating lunch.
"Oliver! I'm going to do your makeup for your date!"
"What?"
"Yeah, you're going to look sooo pretty!"
Oliver stared at Lauren and Courtney. "Is she serious?"
"Absolutely! You need to look beautiful for Lucy." Lauren replied.
"Mom, please don't let her do this." Oliver pleaded.
"Or how about you don't wear anything for the date instead? You can greet Lucy at the door naked."
Oliver understood and looked back at Ivy. "Okay. Fine..."
Ivy grabbed Oliver by the arm and pulled him into his room. They sat on the floor together and Ivy started brushing his cheeks with foundation.
Half an hour later, Ivy brought Oliver back into the kitchen. The makeup was messy. There was bright red lipstick not properly aligned to his lips, and the colors on his eyes and cheeks were too bright. He almost looked like a clown. Lauren and Courtney immediately started laughing.
"Oh, it looks great, Ivy!" Courtney lied.
Lauren handed him a mirror. He almost started crying.
"I don't want Lucy to see me like this..."
"Oliver, how rude! Ivy did a wonderful job." Lauren scolded.
"What dress is he going to wear?" Ivy asked.
"Oh, you have to see it!" Lauren ran out of the room and returned holding a golden, sparkly dress. "Try it on now, Oliver!"
The boy put on the dress. It was extremely short and barely covered his genitals. "Mom, this is shorter than anything I've worn at school. Look! You can see everything!" He tried pulling it down further, but it wouldn't completely cover his penis and balls.
"Maybe he needs some underwear to cover himself." Courtney suggested.
"All he owns is boy underwear. That's not going to happen." Lauren replied.
"Can he wear mine?" Ivy asked. Everyone paused. Then Ivy reached under her dress, and pulled down her panties. She held them up, they were small and pink. "They might fit him!"
"Ivy, how thoughtful of you!" Courtney said.
"Try them on, Oliver." Lauren told the boy.
Oliver took the panties and stepped into them. They were better than nothing, he thought. They were tight, but they covered his nakedness.
Lauren received a message on her phone. She checked the message and smiled. "That's Lucy's mom. They're on their way now."
"We better go." Courtney said.
"Oh, can't we stay?!" Ivy asked.
"No, it's their little play date. We should give them some privacy. Be nice to her, Oliver!"
The Date Begins
Soon, Lucy arrived. Oliver was waiting in the living room, nervous. Combined with the normal nerves of hanging out with a girl he liked, he hated how short the dress was, and how he looked terrible in the makeup.
Lauren walked in with the little girl.
"Hi Oliver!" Lucy smiled.
"Oh, hi!" Oliver stood up and awkwardly waved.
Lucy was taken aback by the makeup, but politely ignored it.
"You two can watch Netflix or something if you want." She handed Lucy the remote. "I'll leave you two alone."
She walked away, and Lucy sat on the couch next to Oliver.
"So what should we watch?" She started clicking through the shows.
"I don't know... whatever you want."
The date was awkward at first, but eventually the two started talking more. Over the next two hours, they talked about school, life, their hobbies, and politics.
"You're such an open minded, kind boy, Oliver." Lucy said, placing her hand on Oliver's.
The boy smiled back, but didn't know how to react.
"I have to go to the bathroom..." He said.
Lauren, sitting at the kitchen table, noticed him leaving the room. This was her chance. She walked into the living room to find Lucy alone.
"Lucy, honey, I have some bad news about Oliver. I was just watching my indoor security camera footage from yesterday, and... I think it's best you see for yourself."
She synced her phone to the TV. After a few seconds of loading, there was the camera footage: Oliver sitting at the kitchen table, naked, browsing something on Lauren's laptop.
"Oh my gosh..."
"It gets worse. Look at what he's doing."
She zoomed in. On the laptop, it was clear: Facebook photos of Lucy.
"Oh. My. Gosh." Lucy didn't know what else to say. She was sick.
On the screen, naked Oliver clicked to a photo of Lucy in her swimsuit while on vacation in Orlando. He started masturbating.
"EW!!!! What the hell!!!" The girl was traumatized.
Oliver walked back into the room and froze when he saw what was on the TV. He couldn't believe it.
"NO!" He screamed. He ran over to the TV and tried to cover it up with his body.
"You are such a gross pervert!" Lucy cried, storming out of the room.
"I'll drive you back home, Lucy." Lauren said, walking after her. "You're disgusting, Oliver."
Oliver dropped to the floor. It was the first time he had cried in days.
I was hoping not to do this, but I will have to take a break from this.
The past few chapters have been difficult to find the time to write (day 7 you could tell was especially short). I still have a lot of ideas, and will pick up on day 9 and continue regularly as soon as I can.
It made me feel so sorry for Oliver but that's why I loved it so much. Having Ivy over to do his makeup was absolute genius I never expected that, I knew Lauren woud have some humiliating ideas for him but I didn't expect that.
The footage of Oliver jerking off to her! Oh no!
Fantastic update. I cannot wait to see what happens next, has Oliver hit rock bottom? Will we see Lucy again?
Brilliant. Fully understand you need some time to get ahead of the story and plan things out so as much as I wish we could carry on getting a chapter a day I understand why you need a break. Can't wait for the story to return!
