The unlucky Babysitter

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
MaireadM
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Re: The unlucky Babysitter

Post by MaireadM »

Mommy is hopefully going to demand the tighty whities.
NickTwisp
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Re: The unlucky Babysitter

Post by NickTwisp »

Very good story. Daniel strips to just his underpants in front of the Mom & 3 daughters.

That's a HOT scene in & of itself, whether it goes any further or not. Especially that his underpants turn out to be white briefs.

When I wore white briefs, especially as they got more worn, they would fit more loosely & my penis would sometimes slip out the side partially.
NudeBaG
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Re: The unlucky Babysitter

Post by NudeBaG »

13 and having to strip in front of 3 younger girls?!
Thatโ€™s a dream and a nightmare for me!
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Re: The unlucky Babysitter

Post by NudeBaG »

Hoping for another update, considering how much time passed between the last one๐Ÿ™๐Ÿป
TheMilkman
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Re: The unlucky Babysitter

Post by TheMilkman »

When my pants hit the floor all I heard was giggles. I couldn't believe it. I was in my underwear in front of the girls I'm supposed to be babysitting. Talk about bad luck. Well I'm sure they will never let me live it down but at least the worst of it was over.

I just let out a good exhale with my spirits high ๐Ÿ˜Œ. And then suddenly there was a new emotion at play. All three little girls looked stunned as their eyes went wide. I watched all their little hands come up to cover their stifled laughs. Geez a second round of laughter. Wasn't the first look at me in my underwear enough? And then Ms. Smith noticed my naivety at the situation.

"Ahh hem, Daniel, uhme." She cleared her throat like she was trying to find the words to tell me some bad news. I just stood in awe. What could she possibly tell me now that was so bad. And then something just clicked in me and without thinking I looked down. My pale underwear looked even whiter with the flower they were covered in.

FLOWER! And then I looked up. The three lovely girls were beside themselves giggling as they were trying to hold back as best they could with no success.

"Now now girls." Even in all this chaos I got the feeling Ms. Smith was trying to calm the situation. I was wrong. "It's not good to hold back a laugh." Following their mother's words they burst out with uncomfortable giggles.

The girls:
๐Ÿ˜‹๐Ÿคญ๐Ÿ˜›๐Ÿ˜๐Ÿคญ๐Ÿ˜œ๐Ÿคช๐Ÿ˜†๐Ÿ˜‚๐Ÿคฃ

Me:
๐Ÿ˜’๐Ÿ˜ฎโ€๐Ÿ’จ๐Ÿ˜ค๐Ÿ˜Ÿ๐Ÿ˜ฅ๐Ÿ˜ข๐Ÿ˜–๐Ÿ˜ฃ๐Ÿ˜ฉ๐Ÿ˜ซ๐Ÿ˜ต

Then suddenly I was back to the situation at hand as I looked down again then back up at the bright faces in front of me. The fits of laughter just wouldn't stop. Ms Smith had a very honest face.

Ms. Smith:
๐Ÿ˜Œ๐Ÿ˜โ˜บ๏ธ

"Anything but that." I had to plead my case. "It's not right." I had to explain why it was wrong. "I can't be seen like that in front of these girls." I had to make the situation rational. With my hands out front I pushed all my emotion out to them.

"Well what you did was not right," Ms. Smith said as she bent down pushing me back with her finger. "And if you want to act bad and misbehave then you can walk home like that." And just like that she picked up my clothes off the ground. Before I could process she locked the screen door. I just watched the giggles slightly fade as Ms. Smith pulled the girls attention with her woods.

It was dark. It was quiet. All I had to do was get home and this night would be over. So it was time to plan my route. But everything went wrong with my first step. My leg immediately landed on a toy car and I just slid forward right into the girls volleyball net. My body turned as I slammed into it hard. Like a rubber band I pulled the net tight until I landed back on my feet. With a calming exhale I started to walk with no success. Shock rushed over me. Some part of the net had hooked onto my underwear ๐Ÿ˜‘. This is ridiculous. What am I in, an embarrassing comedy? My attempts to unhook from the net were futile. This was unbelievable I just had to get off this stupid thing.

I kicked the toy car away from me as I started walking forward. The rubber banding of the net started up again. Any second now this thing should just unclip from me undies.

That was a pipe dream because what was really happening was so microscopic you couldn't even hear it right away. The undies began to tear slowly. It was not enough force to peel them clean off but it was a start. As Daniel got close to the light from inside the house everything clicked. Daniel's foot slipped as the net yanked him back before throwing him forward like a slingshot as the net ripped the underwear off of him.

Inside the house the girls were turning their attention to mother.

"See this is what happens when you don't follow the rules," Ms. Smith said as she waved around Daniel's pants. All the girls had the same thought. It was unfair. They were so close. "You understand right girls?" All the girls nodded. "Yes mother!" All the girls could still laugh but it was a bummer. All the girls took their stab at the situation.

"But we almost saw nakey," Alex said, as she crossed her arms powdy.

"Ahh I won't get another chance like this till I'm like twenty," Jessy said, as pulled on her hair a bit.

"Yeah, and I was hoping on breaking in my new camera," Marnie said, grabbing her Polaroid camera off the shelf. Ms. Smith could understand their frustration with missing out and leaned down as she promised them they'll see the nakedness of a boy someday. She even felt a little sorry for them and even thought about how the situation could have went different in her girls favor. Ms. Smith just smiled as she consoled her girls that is until..

SPLAT

Ms. Smith's eyes gently opened as she was met with the naked boy smashed against her sliding glass door. Ms. Smith just smiled as she pushed on the shoulders of the girl sandwich in front of her.

Daniel's eyes popped open as he saw the gentle smile of a mother and the backs of three heartbroken girls. He just closed up his eyes trying to leave this unreal nightmare. Ms. Smith tapped their shoulders as she looked past her girls.

"Ohhhh, hehehehe." Daniel's brain let the panic set in as he heard her voice through the glass. "Welcome back Daniel-." Her lips quivered as she hesitate on the last word. But it was inevitable. Welcome back Daniel-Nudibutt." All the girls turned on their feet until they were facing the door. ๐Ÿ˜ฑ๐Ÿ˜ฑ๐Ÿ˜ฑ. Their faces all shocked at the sight in front of them. He was completely exposed head to toe with his dangle bits smashed up against the glass.

"Ooooo, hehehehe." It was a complete embarrassment with the laughter stifled to giggles only for those to turn into admiration for the sight before them with all their ooos and awes.

"Well girls do you think he's learned his lesson?" With eyes closed he just waited for the embarrassment to be over. "I'd say so," Alex said, eyeing the misbehavior in front of her. "Yeah he made a BIG mistake," Jessy said, using her hands to show how big it was.

"Alright I think that's enough." Finally she said those sweet words. Finally he could just move on with this. Finally Daniel opened his eyes only for them to narrow in on the camera in Marine's hands.

"Wait I'm gonna remember this one forever," Marnie said, getting her full subject in frame. "Smile." Daniel blinked as the flash caught him off guard. His face scrunched up as he watched the photo slide out of the camera. Marnie just smiled as she waved the photo around letting it develop. The girls all giggled as they looked at the photo.

"Ms. Smith!" I was back to reality. This was insane. A naked picture of me. This isn't a naked movie. Ms. Smith seemed to read the plea on my face as she heard my scream.

"Alright girls, we can't have too much fun now," Ms. Smith said snatching up the photo. I couldn't breathe I had to keep watching it unfold as she pinned the photo to a weekly schedule board. "Now bedtime girls." The girls all stepped forward in sync as they spoke simultaneously. "Goodnight mister babysitter!" The girls shouted as they blew me kisses goodbye while they eyes took one last look downstairs. I just listened to them laughing up the stairs as Ms. Smith just peeled me off the glass.
NudeBaG
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Re: The unlucky Babysitter

Post by NudeBaG »

Donโ€™t tell me this is the end๐Ÿ˜ญ
It was just getting good
The ages of all the characters are perfect!
Would love some descriptions
Mom being involved might complicate things, but hopefully, sheโ€™s a โ€˜naughty mommyโ€™ ๐Ÿ˜ˆ
NickTwisp
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Re: The unlucky Babysitter

Post by NickTwisp »

Daniel's underpants are apparently covered in "flour," not the plant "flower."

Nice touch, having the entanglement with the net cause his underpants to be ripped off. I guess he returns naked to their house to hopefully be provided with something to cover himself with. So is his penis developed in any way at age 13?
NudeBaG
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Re: The unlucky Babysitter

Post by NudeBaG »

NickTwisp wrote: Tue Mar 31, 2026 4:41 pm Daniel's underpants are apparently covered in "flour," not the plant "flower."

Nice touch, having the entanglement with the net cause his underpants to be ripped off. I guess he returns naked to their house to hopefully be provided with something to cover himself with. So is his penis developed in any way at age 13?
From Jesseโ€™s words and hand gesture, Iโ€™m guessing he might actually be well endowed.
Letโ€™s hope we find out๐Ÿ˜ˆ
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Re: The unlucky Babysitter

Post by NudeBaG »

The pacing of this story is so quick, but SO good!
I still think the momโ€™s involvement has perhaps limited things, but then again, heโ€™s still naked, and the girls are still there.
I have no idea what you have planned, but now that the girls have seen their babysitter naked, I doubt theyโ€™ll let their fun end so abruptly
MaireadM
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Re: The unlucky Babysitter

Post by MaireadM »

I hope he makes it home safely NAKED
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