The unlucky Babysitter

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

Post by NudeBaG »

MaireadM wrote: Tue Mar 31, 2026 10:37 pm I hope he makes it home safely NAKED
But he’s the babysitter.
Mom probably still needs him to stay the night, if she was planning on going out.
I hope this babysitting job isn’t over yet.
Those girls seemed pretty excited😈
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Re: The unlucky Babysitter

Post by TheMilkman »

I feel this is the end, but if I did keep it going what should I do? Continue from right here or jump to the next day of babysitting. Tell me what you think and I may write more.
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Re: The unlucky Babysitter

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TheMilkman wrote: Wed Apr 01, 2026 6:27 am I feel this is the end, but if I did keep it going what should I do? Continue from right here or jump to the next day of babysitting. Tell me what you think and I may write more.
I'd suggest bring in a new babysitter, a completely different boy but keep the girls and their mom. That gives you a clean slate, because honestly it's pretty unbelievable there would be any babysitting from this boy at this point. He'd just suck up the humiliation and cut and run home.
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Re: The unlucky Babysitter

Post by Jeepman89 »

I would change the babysitter and make sure he has a good sized cock.
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Re: The unlucky Babysitter

Post by TheMilkman »

Yeah I know it was stupid. But of course I was going back. I was making money. Maybe my long game was destroyed but maybe it wasn't. It could be a cute story to tell our children. Anyway I finally made it to the door but before I could knock it opened.

"Oh Daniel?" Ms. Smith seemed surprised as she was racing out the door. "Sorry I didn't think you'd be back because of last week so I hired another sitter." Did she think I was too embarrassed to come back. Great I've been seen naked and I've lost my job. I wonder who they replaced me with. A foot quickly caught the door before it closed. "Have a good day at work Ms. Smith!" Oh my God. It was Ricky. He was taller, more muscle, one year older, and a bit of a bully. His long brown hair laid over his tight tank top and shorts.

"What's going on dork?" I didn't know how to respond to him. I just stood frozen. "What a sweet gig here you got booted from," he said leaning in. Did he know the story? He wasn't giving me that exact expression. Well he was older so his long game had to be much bigger than mine.

"Well I guess you'll have fun watching the girls." I spoke with contempt and satisfaction. Maybe this was a good thing. He can watch over them giving time for them to forget my little accident. His eyes glanced back as he smiled. "And then some." His little addendum to my sentence startled me as I put my foot in the door keeping the conversation going. "What does that mean?" I had to be sure about his intentions. Ricky looked back as he closed the door behind him.

"Oh I'll have fun alright, I mean have you seen their butt cheeks." My eyes went wide as he reached out reenacting grabbing two big watermelons. I just shook my head in disbelief. "And that Marnie, I think her shirt is a little loose maybe I can fix it for her." Ricky just pictured a situation I wasn't willing to envision. What the fuck! Where was his long game. He is too old for them. They are too young for this stuff. He's basically talking about assault. I couldn't believe him. He could see the rage on my face. "Relax dork." Ricky just pushed my face back. "I'm not an asshole, I wouldn't do anything inappropriate." Oh thank God. "Not without consent." 😳. Consent what is he a lawyer? This can't be happening.

"Who's at the door?" The door burst back open as Marnie came outside. My eyes just crawled up the short shorts and tank top. Marnie almost immediately started laughing at seeing me. I quickly pulled her forward as I whispered. "Please don't tell anyone, please." Marnie just nodded as she covered her laugh. As she bent forward Ricky bit his lip staring at her back side. "Daniel can you see down my shirt?" My eyes crossed as I saw the void between two dangling stalactites. My eyes didn't know where to land, on Marnie's low hanging fruit or Ricky's lips mouthing out the word B.O.O.B.I.E.S. Based on my expression she got the hint as she pulled herself up eyeing Ricky hard. Ricky just watched her booty walk back inside before turning back to me. "By dork." And like that the door was closed.

No no no. My long game! If Marnie is infatuated then the other girls might be too. I gotta put a stop to this quickly.
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Re: The unlucky Babysitter

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TheMilkman wrote: Wed Apr 01, 2026 7:36 am Yeah I know it was stupid. But of course I was going back. I was making money. Maybe my long game was destroyed but maybe it wasn't. It could be a cute story to tell our children. Anyway I finally made it to the door but before I could knock it opened.

"Oh Daniel?" Ms. Smith seemed surprised as she was racing out the door. "Sorry I didn't think you'd be back because of last week so I hired another sitter." Did she think I was too embarrassed to come back. Great I've been seen naked and I've lost my job. I wonder who they replaced me with. A foot quickly caught the door before it closed. "Have a good day at work Ms. Smith!" Oh my God. It was Ricky. He was taller, more muscle, one year older, and a bit of a bully. His long brown hair laid over his tight tank top and shorts.

"What's going on dork?" I didn't know how to respond to him. I just stood frozen. "What a sweet gig here you got booted from," he said leaning in. Did he know the story? He wasn't giving me that exact expression. Well he was older so his long game had to be much bigger than mine.

"Well I guess you'll have fun watching the girls." I spoke with contempt and satisfaction. Maybe this was a good thing. He can watch over them giving time for them to forget my little accident. His eyes glanced back as he smiled. "And then some." His little addendum to my sentence startled me as I put my foot in the door keeping the conversation going. "What does that mean?" I had to be sure about his intentions. Ricky looked back as he closed the door behind him.

"Oh I'll have fun alright, I mean have you seen their butt cheeks." My eyes went wide as he reached out reenacting grabbing two big watermelons. I just shook my head in disbelief. "And that Marnie, I think her shirt is a little loose maybe I can fix it for her." Ricky just pictured a situation I wasn't willing to envision. What the fuck! Where was his long game. He is too old for them. They are too young for this stuff. He's basically talking about assault. I couldn't believe him. He could see the rage on my face. "Relax dork." Ricky just pushed my face back. "I'm not an asshole, I wouldn't do anything inappropriate." Oh thank God. "Not without consent." 😳. Consent what is he a lawyer? This can't be happening.

"Who's at the door?" The door burst back open as Marnie came outside. My eyes just crawled up the short shorts and tank top. Marnie almost immediately started laughing at seeing me. I quickly pulled her forward as I whispered. "Please don't tell anyone, please." Marnie just nodded as she covered her laugh. As she bent forward Ricky bit his lip staring at her back side. "Daniel can you see down my shirt?" My eyes crossed as I saw the void between two dangling stalactites. My eyes didn't know where to land, on Marnie's low hanging fruit or Ricky's lips mouthing out the word B.O.O.B.I.E.S. Based on my expression she got the hint as she pulled herself up eyeing Ricky hard. Ricky just watched her booty walk back inside before turning back to me. "By dork." And like that the door was closed.

No no no. My long game! If Marnie is infatuated then the other girls might be too. I gotta put a stop to this quickly.
Is marine flashing a deep cleavage, or her actual boobs when she does that?
Other than that, this got very interesting!
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Re: The unlucky Babysitter

Post by NudeBaG »

Not gonna lie.
Pretty disappointed we didn’t get a straight follow up.
Not liking Ricky at all.
Would have much preferred things continue with Daniel from that night.
The girls barely had any time with him.
It was such a solid, promising set up😓
Oh well.

You’re still a great writer, just a little upset with the possibilities we won’t get to explore now.

The mom seemed on board with everything too.

I liked Daniel’s personality and demeanor a lot more.

“No no no. My long game! If Marnie is infatuated then the other girls might be too. I gotta put a stop to this quickly.“

I’m hoping Daniel can pull a Hail Mary here.
Get Ricky out of there.

The girls flirtation with Daniel and having already expressed interest in him is a much stronger plot.
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Re: The unlucky Babysitter

Post by NudeBaG »

Jeepman89 wrote: Wed Apr 01, 2026 6:56 am I would change the babysitter and make sure he has a good sized cock.
I was under the impression he already did have a nice sized cock.
The girls’ reactions confirmed that
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Re: The unlucky Babysitter

Post by NudeBaG »

Freesub wrote: Wed Apr 01, 2026 6:46 am
TheMilkman wrote: Wed Apr 01, 2026 6:27 am I feel this is the end, but if I did keep it going what should I do? Continue from right here or jump to the next day of babysitting. Tell me what you think and I may write more.
I'd suggest bring in a new babysitter, a completely different boy but keep the girls and their mom. That gives you a clean slate, because honestly it's pretty unbelievable there would be any babysitting from this boy at this point. He'd just suck up the humiliation and cut and run home.
I liked the character.
He deserves a 2nd chance
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Re: The unlucky Babysitter

Post by TheMilkman »

A little bit earlier...

I was in the prime of my life. Ms. Smith was just finishing getting ready. I hit the mother load. Ms. Smith had on these tight leggings. I hit the jackpot of jackpots. And this button up shirt screaming for another button to be undone but for now three was plenty.

"Oh Ricky thanks for helping out on such short notice." Ms. Smith couldn't help herself from hugging me as my face was pushed into major cleav. Oh I'd do anything for them. As she pulled away I knew I had to get me a pair of those. "I'd do anything if the world for you Ms. Smith." Without warning Ms. Smith turned around and kissed me on the cheek. "Your so nice and sweet." Ms. Smith just moved to the door before saying one last thing. "And cute too." And with a wink she opened the front door. "I'll say," Marnie said in agreement as the three sisters walked down the stairs. Thank you God. I know that every wedgie, noogie, or swirly has led me to this moment. My eyes laid on the girls as their mother greeted someone outside the door. Simple atir for all the girls, tank tops and shorts, me likey.

"I better see who's at the door," I said before following Ms. Smith.
A couple minutes later... "By dork." And I shut the door in his face. No more of that guy for the night.

"Oh Mr. Babysitter!" That was my call to action. All the girls were in the living room in front of the TV. "Hey Ricky it's our yoga time so you just sit on the couch." I didn't even get a say as Alex pulled me into the couch. The girls took up my view as they looked back and me giggling. This felt like paradise. All three girls stood apart as they bend forward smiling at each other. In front of me was three fresh heinies. They wiggled in front of me before the girls turned around. And just like that the bend forward and I could see a lot.


My eyes panned right to left. -- \/\/ --
I saw flat plains, then rolling hills, then more plains. Marnie was bending extra low. So low I think if I squinted I could also see some Hershey kisses. Then suddenly the girls pulled themselves up.

"I think it's time we each took a bath," Marnie said, as she bit the tip of her finger. These girls were wild. Through the soft snickers they each looked at me. "Can you give us each a bath?" Woah totally wild. Their eyes were alluring and crazy. As much as I'd love to get to know them better this felt like a trap.

"Ladies please, I'm but a humble man, it would be inappropriate if did that." I just stood up slowly. "But a shower would be nice after you three are done." The girls almost fell into each other laughing. I watched hips swivel as they went upstairs. I've got things all figured out. I just sat back down with the TV on. Back to paradise, that is until a little time past. My show was quickly interrupted by three girls in towel. I almost wanted them to move and then they bent over facing me.

"Wanna help us pick out clothes?" They all spoke together. I almost swallowed my knuckles before getting up and walking to the stairs. As I got to the stairs they pulled me back so I could watch them go first and what saw was amazement. Three little pairs of underwear. Finally we were at the top. I just watched the girls pull out different colored tank tops. I kept it simple picked a few colors then started my retreat, but I was stopped.

"Ricky." I turned as Marnie was right next to me with her shirt rolled up over her chest. It was like a paper jam. "Could you help me with my shirt?" I cracked my knuckles. This is what I had been training for. I just grabbed the bottom of the shirt attempting to pull it loose. "Might be stuck on your bra." I kept it smooth as I watched her playful eyes. She just smiled as she spoke. "What bra?" Oh this girl likes to play. I smiled back. "The one I swiped when you weren't looking." Her face was in pure shock as I just pulled down her shirt. I watched her shirt even out before leaving the room. "I'm gonna take a quick shower ok girls." All the girls rushed the door as I entered the bathroom. And then I was gone for now. With a couple doors between us I started to strip.

The girls were so excited they couldn't hold it. They all pressed up against the door as they listened for the water to run. Marnie quickly grabbed her camera as they turned the nob. All the girls froze when they saw him. He was hidden behind the shower door but you could definitely see things. Marnie's eyes crossed as she got a glimpse of his dangle bouncing around between his legs. Alex quickly pulled his clothes off the counter as Marnie help up her camera. And then the doorbell rang. Marnie quickly set down her camera on the counter as they rushed downstairs.

I just rang the doorbell again and again until it opened. There they were my three girls. They did not look happy to see me, grumpy even.

"Good you're all here, can you please tell your mother I want to come back as your sitter." I prayed to them but all I got was a collective no. "But why?" Each girl just smiled as the spoke.

"Cause Ricky is cuter."

"He's got muscles."

"And he's a sure thing."

I don't even know if they understand what is coming out of their mouths.

"Plus we have seen just about every inch of you, so we are satisfied." I just looked at them confused. "Plus I think Ricky is bigger." Marnie just raised her hands like she was measuring something. "I guess we'll know when he's out of the shower." They all just giggled and before I could interject another voice called out.

"Where are my clothes?!?" The girls just all waved goodbye as they shut the door.
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