A date with the prettiest girl in school

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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TheMilkman
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A date with the prettiest girl in school

Post by TheMilkman »

It was another Friday night like most. I couldn't help but relax myself. I was feeling good listening to some tunes as I checked myself in the mirror. I was ripped (lie) and muscular (lie). With just the right amount of chest hair (none). I slicked my hair back as I was kissing the mirror. I was looking good for eleven.

"Hey Mom what's for dinner!" There was no response. I pulled on a shirt and leaped through the house. It was empty. Before panic mode set in the doorbell rang. The fokes must have just locked themselves outside. "Did you guys-." I couldn't finish my sentence as I opened the door. Standing on the other side was my neighbor. Jen was the prettiest girl in my class. She was dressed in baggy jeans with a white tank top that really showed off her figure. Her blonde hair was pulled back into a messy bun.

"Sorry I'm late, I guess your mom and dad already went out, poor Jimmy I'll just get dinner started," she said, walking by me. I just watched as she made her way to my kitchen. I froze for a moment. I quickly moved to the wall peering around it. Jen was setting up ingredients on the counter. In a panicked state I rushed upstairs to my room.

---
"Ok in bed by eight..." Jen slowly read off the note left by Jimmy's parents as she prepared mac and cheese on the stove.
---

I was freaking out. I didn't know what to do or say. Jen was in my house cooking me dinner. But why. And where were my parents. Then a light bulb went off. Oh it's a date. Of course it is I mean look at me. As I flexed in the mirror I could hear her voice.

"Jimmy dinners ready!" Her voice sent shivers down my spine. I've never really even talked to her and now I have to have dinner with her. I tried to calm myself down as I walked down the stairs. She set the table as I entered the kitchen. She was so beautiful. I sat across from her as I picked up my fork. I just had to make simple conversation. I began trying to find the words.

"So how about those economics?" Was what I wanted to say but all that came out was. "Da...uh...hi..who." She just laughed listening to me. Her laugh was angelic and caught me off guard as I just tried to take a bike of food. My hand fumbled and I got Mac and cheese in my lap. I couldn't let her see the mess I was making so I just ate through it. That was until she got up grabbing my plate.

"Huh look at you (giggle), looks like someone needs a bath." That's when the doorbell rang. "You go get ready, I'll get the door." She wants to join me in the bath. I felt blood rushing all over my body. I rushed upstairs. I just paced back and forth trying to sike myself up. I didn't feel like I could go through with it though. Maybe if I bathed really fast she would need to get in with me I quickly pulled off all my clothes and got in the tub.

---
Jen got to the door opening it slowly.

"Hello Miss are school is selling magazines." Standing there was Pete. He was one of the tallest guys in Jen's class. Beside him was a cute girl by the name of Maple. She had curly red hair.

"What's up guys?" Jen asked. They looked a bit confused. That's when another person entered the equation.

"Jen what are you doing at Jimmy's?" Mark asked, pulling up on his bike. Mark was the school bad kid. Your run of the mill bully complete with leather jacket and all.

"I'm babysitting while his parents are away," Jen said, hanging in the doorway. The three preteens started laughing.

"No way, where is the little guy?" Mark asked, as he jumped off his bike.

"He's in the bath, you guys wanna come inside."
---

I was relaxing, really enjoying the hot water when I heard a voice.

"You better be in that bath mister!" Jen shouted from the bottom of the stairs. I panicked. I didn't want her to see me naked. I began trying to reach for my clothes. I fell out of the tub as I heard footsteps. I quickly jumped back in as the knob turned. I'm too young for this. The door opened slightly. "Here's a towel I'm gonna take these dirty clothes," she said hiding behind the door. What a relief. I quickly dried myself off. She took all my clothes. All I had was this towel. I searched for anything else to wear. The only thing was a cabinet full of diapers. Oh I hate my mom. Because of an accident when I was five she always kept diapers on stand-by. She's always teasing me with these.

I just tightened the towel and left the bathroom. I could hear voices. I crept down the stairs slowly. I moved through the kitchen as they came into view. Jen was chatting with some kids from school in my living room.

"Hey what's all these people doing in my house!" I yelled, as I tightened my towel. Everyone turned to me. Jen did not seem to like my attitude.

"You do not talk to me like that, bed time now mister," Jen said, scolding me as she pointed to the stairs.

"Bed time? And why should I?" I asked, pulling up my chin.

"Because you have to do what I say that's what your parents hired me for." I couldn't comprehend what she just said.

"My parents hired you to date me?" As I spoke these words everyone froze wide eyed.

"Date? I'm your babysitter dude," Jen said, trying not to laugh. The other three couldn't hold back their giggles.

"Dorky thought he was on a date with Jen," Mark said, pointing and laughing. I was embarrassed and angry at the same time.

"Get them out of here," I said, pointing to the door.

"Hey you do not talk about guests like that, now you will behave or I will put you in a diaper," Jen said, raising her voice with me. A diaper?!

"I'd pay to see that," Pete said, poking Maple in the stomach with his elbow as they laughed.

"A diaper?" I asked, breathing heavily.

"Yeah your mom said if you misbehave they're under the bathroom sink," Jen said getting in my face. Before I could say anything else she picked me up in her arms. "Now let's get you to bed." I watched from over her shoulder as my classmates laughed at me in my humiliation. I pulled on my PJs and crawled into bed but I couldn't sleep. Jen had put music on downstairs. I moved to the door but couldn't hear them talking downstairs. This night was ruined. I had to get my mind off of it. I crept downstairs quickly. My eyes were on a jar of candy on top of the fridge across from the broom closet. I moved a rickety stool over and stood tall as I reached for it.

I was so close. I just barely had it until I was startled by the music suddenly stopping. The stool fell forward then back as I launched backwards. My pajama shirt snagged on the broom closet door. I just hung there unable to get myself free. My shirt was pulled up just enough to cover my vision as someone walked into the frame. I could see their shadowy outline through my shirt.

"Someone is very cranky," Jen said, through a stifled laugh. "Hold on guys I'm just checking on Jimmy." Before I could blink my pants were pulled down to the floor. My bare naked body was on full display for all to see but not for long as I felt a diaper wrap around my waist.

"Wait Jen," I said, trying to wiggle her off. That's when more laughs entered the room.

"What do we have here?" Mark asked, checking out the situation.

"Oh my God," Maple said, astounded.

"He's trying to wiggle out of his diapy," Jen said, as she sealed it tight around me.

...to be continued?
TeenFan
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Re: A date with the prettiest girl in school

Post by TeenFan »

What a nightmare.
Maybe the guests can join in with Jen in a game of pin the tail in the diaper.
Jimmy will probably be a bad boy and need a minor dose of discipline at some time that night.
Datom
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Re: A date with the prettiest girl in school

Post by Datom »

Neat premise. He thought she was his date but she turned out to be his babysitter. And now she has an audience in front of whom she can humiliate him.

I'm definitely gonna want to read the next installment of this!
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