The unlucky Babysitter

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

Post by TheMilkman »

It was late. About eight o'clock. I had one job put the girls to bed. Who was I? The babysitter.

I was thirteen. I was in my prime. I was ripe for picking and so were they. But I was smart. I was older so this was the long game. Jessy was the youngest at nine years old with her beautiful blonde hair. Alex was ten and she looked it with a bright smile and long flowy brown locks. Then there was Marnie. Oh what an angel. She was eleven but didn't look like it I swear. I mean she was something else. Tall but not as tall as me, smart but not as smart as me. And down right beautiful. She had these....I mean she was....when you looked at her you saw.....Marnie had really developed and I could say without a doubt she filled out her tank top. I know this was all wrong to think about but like I said I was playing the long game, in a couple years they would be perfect for me. Not to mention the slight vibe that they wanted me now. Jessy was in bed waiting for me with her teddy bear. As I tucked her in she spoke.

"Mom usually kisses me goodnight." The other girls squealed at her comment. I was in heaven and with a little peck to the forehead I was that much closer to God.

I was Daniel. I was getting ready. My job was to put them to bed. So I was preparing. Cologne, hair gel, a mint, and the best fit. A tight black shirt, nice black skinny geans, and bright white shoes.

"Ok Daniel we're ready!" That was my que to leave the mirror but not before a quick little dance to shake the goods. Then I was moments away as I turned down the hall into their room. Oh the temptation was high and the choices were good. Next was Alex. She was sitting up waiting for me. She needed a nightlight by her side. Nothing I couldn't do. I just slid by her bed as I bend over plugging it in. I could hear the girls giggling at something. And that something was on full display so I gave them more of what they wanted.

"Just give me another moment," I said as I wiggle my butt back and forth. It was quiet but I could hear them go crazy and when I pulled up Alex asked for the same goodnight kiss but on the cheek. This was paradise. Last was Marnie. She was laying still with her jet black hair raining down the bed. Her request was simple, I just had to tuck her in. Oh if only things were so simple. As I pulled the blanket tight it snagged on a few lumps. Two well placed lumps. Marnie just smiled as I pull down on the blanket. Her chest jiggled like balloons that could pop at any minute. I had to play it cool. I was old enough for this stuff not to bother me and I knew exactly what was going on. I just took a deep breath and smiled.

"It must be your bra snagging on the blanket." With all the confidence in the world I moved in close pulling the blanket over the mounds. Marnie just smirked as she leaned into my ear. "What bra?" Her sudden whisper was loud enough to cause a small eruption of giggles. As I let go of the blanket the tide came in pushing the beach balls back into place. I just pulled back scratching my head. I was real close to the urge but I had to fight it in my pants. With a calm breath it was over or so I thought.

"Where's my goodnight kiss?" Well of course just like the other girls she wants a taste of the old Daniel. One last thing before bed. With a crack of the neck I moved in. "Ah ah, I get my kisses on the lips." Well of course everyone gets there kisses....😳. Did she just say the lips. The other girls couldn't hold back snickers as Marnie pulled on the lip balm. I watched her lips perk and pop as she licked them. I was a bit frozen. "Please Daniel, I won't be able to sleep without it." The puppy dog eyes got me. I held my breath and moved in. Marnie bit her lip as she grabbed the side of my face. Our lips got close teasing each other until she just slammed our faces together. The loud sound of lip smacking lasted two seconds before I pulled back. The other two ooooed and awed while Marnie just licked her lips eyeing me. And so I rushed out slamming the door behind me. That could have done worse. Without realizing it I seemed to begin a camping trip with an already pitched tent. I sure hope none of them saw anything.
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Jeepman89
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Re: The unlucky Babysitter

Post by Jeepman89 »

Love this!
NudeBaG
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Re: The unlucky Babysitter

Post by NudeBaG »

Keep going!
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Re: The unlucky Babysitter

Post by NickTwisp »

Those girls are probably wondering just what Daniel might look like partially undressed...say in just his underpants.
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Re: The unlucky Babysitter

Post by MaireadM »

Very interesting start.
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Re: The unlucky Babysitter

Post by steam train »

Great start. Thank you for posting. Love the first person approach.
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Re: The unlucky Babysitter

Post by NudeBaG »

I posted a babysitting story a while back.
Always a fun scenario!
TheMilkman
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Re: The unlucky Babysitter

Post by TheMilkman »

I was safe. I think if I wasn't careful something bad could have happened. I know a boy my age shouldn't be thinking about this stuff. So really I wasn't. This was all future stuff. Like hooking up, and dancing, and kissing. Wait, was that my first kiss? And then the moment played back in my mind. She grabbed my face and kissed me while I was looking...looking down...looking down at a cave between two big mountains. I gotta clear my head. Boys shouldn't be thinking of stuff like that they should be thinking of... And then I saw it on the fridge. A note in plain writing.

No cookies tonight, I hid the jar.

That's what I should be thinking of. Even if it says no I am the authority tonight and it's ok if I just have one. So I looked. It started to feel pointless until I opened the garage door and there it was on a high shelf next to a bag of flower. Bingo. I just had to do some math.

Step stool+me+height=cookie

And so I climbed but it was just out of reach. I was so close I could almost taste it but as I tried to push the jar something else was moving and then it happened. The stool shifted as I slammed into the shelving. I fell right off onto the floor as I watched the jar rock back and forth. And when it finally stopped I was relieved until something next to it tipped and suddenly the flower rained down on top of me. I was covered in the stuff and without thinking I almost tracked it inside. The backyard seemed like a better idea, that is until I heard a voice. It was her's, the mother. Ms. Smith was home. I scurried to the sliding glass door as I caught her. Ms. Smith was tall and curvy with the right points sticking out and a button up shirt that wasn't buttoned high enough. She spotted me immediately.

"Daniel what are you doing outside?" Ok this was my chance to come clean and be honest. I just hid behind the wall as I slowly opened the sliding door. "Well you know the jar of cookies?" Was I asking her a question or a statement. I couldn't believe myself. I felt like she was gonna yell at me. "That one linked to this note saying don't touch?" I just nodded calmly as she scoffed. "And you didn't touch them did you?" I had to come up with words fast. "IdiditIadmititI'msosorry." I just balled my eyes a bit as I forgot to pause between words. "I'm so sorry Ms. Smith, I tried to grab one and ended up getting flower all over myself." I was close to crying but not there yet as she watched me pull myself out from behind the wall. With a strong glance the situation became clear to her.

"Wow yeah look at you, all filthy, better get you all cleaned up before sending you home to your mother." She was so understanding. She was so nice. She was the best friend a kid could have or so I thought because as I walked forward she pulled up her hand to stop me. With a pause motion she kept me outside and with a point she directed my next action. Her finger traced my pants and shirt. 🥲 This was indeed my face. It was bad but it could be worse. And then I heard them. Three soft giggles. I just turned my head as I noticed the three girls out of bed. My nose almost got sucked up into my face.

"What are they doing out of bed!" I shouted pointing at the girls. "Oh the girls just wanted to say goodnight to their mother." Yeah that makes sense. Suddenly my mind went blank. All I could focus on was the three girls gently snickering at me. Alex tugged on her mom's shirt looking up at her with a laugh as Ms. Smith just nodded back to her. Sometimes things could be spoken without words and suddenly all eyes were on more. To be more accurate all eyes were on my pants. *Whistle* That sound pulled me back to reality as my eyes went wide. "They should be in bed!" I shouted curving my arm to a nice arched point.

"And babysitters shouldn't misbehave." She raised her voice high scolding me. I had to retaliate quickly. "But I can't take my pants off, not in front of all these girls." I pleaded my case. But it didn't feel like enough. Saying it out loud felt like a bad thing to do as the laughter erupted between the girls as they all smiled at me. Ms. Smith also joined in on the laughs before cutting back in. "What do you say girls?" All the girls cut in front of their mother with their hands on their hips as they spoke simultaneously. "Lose um!" Again I followed their eyes as they landed right on my pants along with their pointer fingers. I could almost hear a strike of lightning behind me. Ms. Smith just put her hands on the sides of her daughters shoulders as she leaned forward. "You heard them Mister babysitter." Ms. Smith's voice was sharp and I was afraid.

Emotion just washed over me. I was in shock how could this situation have gotten like this. I don't know what I'm supposed to do. And then it became clear. I glanced over the playful giggles and smiles of the girls until my eyes landed on the mother. Ms. Smith wasn't laughing anymore she was looking at me with heavy patience. This moment now was a deciding factor on my long term plan. If I didn't do what she said I may never babysit again.


I closed my eyes as I pulled off my shirt. The laughter didn't stop. In fact some wooos were added in. I couldn't find my waistband so I opened my eyes looking down at my legs. With a deep breath I undid my zipper and rolled down my pants. Suddenly I was stranded just outside in nothing but my underwear. To be more accurate I was in my underpants, nice bright and white tightey whiteys.

The snickers were turning my cheeks red. It was the most embarrassing thing I'd ever been through but thankfully it was over...
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Jeepman89
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Re: The unlucky Babysitter

Post by Jeepman89 »

Hopefully it's not over! He needs to lose the underwear too.
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Re: The unlucky Babysitter

Post by NudeBaG »

Nice pace.
I agree.
Lose the underwear.
Hopefully, mom doesn’t hinder any fun the girls might have.
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