Babysitter

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This story is intended for adults only. It contains depictions of forced nudity, spanking, and sexual activity of preteen and young teen children for the purpose of punishment. None of the behaviors in this story should be attempted in real life, as that would be harmful and/or illegal. If you are not of legal age in your community to read or view such material, please leave now.

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“Mom, do I really need a babysitter? I mean I'm thirteen, after all.”

“Probably not, sweetie, but it would make your father and worry less. And besides, don't you think a whole weekend alone in the house would get lonely?”

“I guess so. I just wish you guys thought I was more responsible.”

“Alright Josh, I tell you what. If you're well behaved for the babysitter and Sam gives your father and I a good report, we'll think about letting you stay home alone next time we go on one of our couple's weekends.”

That was seriously good news. My parents went on trips like this once every three or four months. Getting the house all to myself that often? A teenage boy's dream come true! I knew right then I'd be a perfect little angel for- wait, Sam? Usually my parents had one of my older cousins, Dennis or Kyle, babysit me. I didn't know anyone named Sam.

“Okay mom. But who's Sam?”

“Sam is a babysitter a friend from work recommended to me. None of your older cousins were free this weekend.”

I tried not to let my disappointment show. Dennis and Kyle usually let me do my own thing and always put on R rated movies at night. I didn't know anything about this “Sam”. Hopefully he'd be cool.

**

I was playing a video game on Friday afternoon when the doorbell rang. I knew that it must be Sam so I paused my game and headed downstairs to meet him.

I got to the door right behind my mom and when she opened the door I was shocked.

Sam was a girl.

And a young one.

And a really cute one.

She looked like she was probably two inches taller than me, so about five foot two. She had short brown hair, freckles, a really curvy body, and there's probably a way to say this more politely, but really big boobs. Luckily she was talking to my mom so they didn't notice me staring.

“Sam, it's nice to finally meet you! How's your summer going?”

“Pretty good Mrs. Smith. I graduated high school last month and I'm going to college in the fall.” That would make her about 18. She looked younger, though. It must have been her height.

“Oh, that's exciting, are you looking forward to it?”

“Definitely. I can't wait. I'm glad you called me, I'm trying to make as much money as I can this summer so I have some spending money while I'm away at school.”

“That's so responsible of you. I'm not sure if we'll need your services again this summer but I'll definitely pass on your name and number to my friends.”

“Wow, I would really appreciate that. And I wanted to thank you for hiring me to babysit Josh. This is going to be my first time sitting for someone older than seven.”

“It's nothing, and don't overthink it. I've been parenting for over thirteen years and once they're out of diapers the only thing that changes is the bed times.” They both laughed at that as my cheeks turned red. I couldn't believe I was about to have to spend the weekend listening to someone just a few years older than me who's used to babysitting children.

My mom turned to me and said “Come over here, Josh, and introduce yourself”.

While I hated pretty much everything about this, I was determined to make my parents think I was responsible and well-behaved enough to stop getting me babysitters, so I smiled as I shook Sam's hand and said “Hi Sam, I'm Josh. It's nice to meet you.”

“You too, Josh. I think we're going to have a really fun weekend together.”

“Me too,” I lied.

She turned to my mom and asked “Is there anything special I need to know about? Allergies, medical conditions, chores for the weekend, stuff like that?”

“Nothing like that,” my mom replied. “Also, Josh's father and I encourage him to do all his chores during the week so he can have fun and relaxing weekends, so besides doing dishes he has no chores he'll need to do this weekend.”

“Wow, Josh is a really responsible kid, then. Well if it's okay with you,” she turned to me as she said this, “and assuming Josh wants to, I was thinking he and I could hit the beach tomorrow.”

“Oh, that sounds like a great idea. And Josh loves the beach, I'm sure he'd be thrilled.”

I was annoyed that no one asked for my input, but my mom wasn't wrong. I do love the beach.

They made small talk for a while and my mom gave Sam phone numbers to reach them. Then my dad came downstairs with packed bags and him, my mom, and Sam made small talk for even longer. Adults can be so boring sometimes.

After a while (it felt like roughly an eternity, but I suppose it was less than 45 minutes) my parents said their goodbyes and Sam and I were left alone in the house. She still had a big smile on her face. I guess she's just one of those people who's always smiling.

“Well Josh, I know your mom said I should babysit for you the same way I would for any of my other kids, but something tells me you won't complain if I don't bust out the coloring books.”

“Haha, you have good instincts for this.”

“So I guess that means a blanket fort is off the table,” she said jokingly.

“Oh yes, I'm far too mature for a blanket fort,” I replied with a laugh.

“Clearly. Someone your age deserves a pillow fort instead.”

“Exactly! See, you get it.” Maybe Sam wouldn't be too bad. She was funny, at least.

“Let me level with you, Josh,” Sam said, acting a little serious. “Your mom says that if this weekend goes well you're probably not gonna need a babysitter in the future. That she's even considering that tells me you're pretty mature and responsible, even for your age. So I'm not gonna do anything crazy, like tell you to clean the bathroom with a toothbrush or go to sleep at 8, and as long as you listen to me when I tell you something we can have a fun weekend and I'll give your parents a great report of your behavior and maturity.”

“That sounds great to me.”

The next few hours were pretty uneventful. I played video games on the computer in the living room. She watched TV and played with her phone in the living room. We joked around about what was on TV. We ordered pizza. We ate pizza. Things were going pretty great, up until the first major hiccup.

“Alright, Josh. It's bath time.”

I really didn't like the thought of being told when to bathe. I was going to shower before I went to bed, I always do, but who likes to be told to do something they were gonna do anyway? But I thought about what she said earlier and swallowed my pride. If obeying her is the price to pay to no longer need a babysitter, I'd do it.

“Actually, I usually take showers. But okay, I'll go do that.” I closed out of my game and started to get up.

“Uhm, I don't think you understand,” Sam said. “Your mom told me to do what I would if I was babysitting one of the kids I usually look after. That means I'm going to give you a bath.”

For a few seconds I was positive I'd misheard her. “Wait, what?”

“So go upstairs, get undressed, and head to the bathroom.”

“But I'm not a small child. I bathe myself. Literally seven times a week. I can't even remember the last time my mom or dad gave me a bath.”

“You're young enough to still need a babysitter, so you're young enough to listen to her. I'm not going to ask again, unless you want me to tell your parents you were difficult for me this weekend.”

My first thought was to tell her to go fuck herself, I'd rather keep needing a babysitter than have her see me naked and bathe me like a toddler. But then I thought about it for a few seconds. Entire weekends of having the house to myself. I could have friends over and we could do whatever we wanted. I could watch porn on the family computer. Hell, I might even be able to convince a girl to come over. All I had to do was get naked in front of an older, very pretty girl.

I gulped. I didn't want to do this, but it seemed worth it, so I started to walk towards the upstairs bathroom with Sam right behind me.

Once we were in the bathroom she wasted no time. She turned on the tub and adjusted the water a bit until she liked the temperature. When she looked back at me I was just standing there. She shook her head and walked up to me.

She grabbed my t-shirt and said “Arms up”. I was past the point of arguing so I complied. She lifted the shirt up and off me and like that I was topless.

Next, she grabbed at the front of my pants and started working at the button. When she got it undone I tensed up and I think she noticed. She looked me in the eye and said “Calm down, I do this all the time, okay?”, and then she kissed me on the cheek. I was so distracted by the kiss that I didn't notice she'd hooked her thumbs into both my shorts and underwear.

The next thing I know my pants are around my ankle and Sam was crouched down in front of me, her face all of six inches away from my penis. Puberty had started but only pretty recently, so while I had pubes they were pretty sparse, and my flaccid dick was about three inches long.

This was insane. The first time a woman had ever seen me naked and she's about to give me a bath. I didn't know how to process any of it so when she led me to the bath I just let her. She had me sit down and then she started washing my upper body. She was talking to me during it all but I didn't hear much.

She was washing me with her bare hands and soap. I won't lie, I really enjoyed the feeling over her fingers rubbing over my chest and head. Eventually she had my top half clean and she said “Stand up so I can clean the rest of you”. I took a deep breath and stood up, once again exposing my naked penis to her.

“Turn around so I can do your back”. I did and she immediately started rubbing soap into my upper back. She slowly worked her way down until she was at my butt. I braced for her to grab it but instead she skipped it and started at my ankle, working her way up. When she got to my knee she said “spread your legs a bit so I can clean between them”. I widened my stance so my feet were about shoulder width apart.

Sam took her time with the next part. She methodically worked her way up my thigh while I stood there with my butt in her face. As she got higher I started to get more and more aroused. Every time she rubbed my leg she got closer and closer to my ass and crotch, until she was only inches away. As she reached the top of my leg her hand gently rubbed against my balls once, twice, and then she stopped and started on my other leg. The feeling was so good I wanted to beg her to keep going despite my embarrassment but I held my tongue.

Her washing my other leg was about the same, but I think it took even longer. I was silently waiting for her to touch my privates again as she slowly worked her way up my thigh. Eventually she reached it and did the same thing as before. She gently rubbed the area twice before stopping.

Then Sam took a second to put soap on her hands again and started washing my butt cheeks. She got them both covered in soap and then, to my surprise, she slid her hand down by buttcrack I think I yelped when she did but that didn't stop her. She started tracing circles around my butthole with her soapy fingers and then she let her hand slide from my butt crack down lower until she reached my balls. I didn't think it would feel good but her massaging down my butt crack to my privates felt amazing.

“Okay, turn around.”

My heart sunk. All of Sam's touching me had the obvious effect on me and I was hard. It was bad enough she saw me naked already, but her seeing me hard seemed so much worse.

“Come on Josh, it's nothing I haven't seen already.”

Knowing there was nothing else I could do, I turned and faced her. My dick was sticking out its full six inches. Sam stared at it and immediately smiled.

“Aww, it looks like someone's excited.”

“Uhm. I guess so.”

“Oh, I just realized I forgot to put conditioner in your hair. Let me do that real quick and then I'll finish cleaning you”. I so just wanted this to be over. She filled her hands with conditioner, a lot more than I would have used, and started massaging it into my scalp. “Close your eyes, sweetie, I don't want this to sting you”.

There she was, treating me like a child again. But she was right, and I closed my eyes while she rubbed conditioner all over my hair and I felt the suds sliding down the front of my face.

She stopped and said “Okay, we'll let that sit for a few minutes while I clean off the rest of you.” There was no teasing this time. She simply grabbed my hard dick with a soapy hand and started rubbing it. It felt amazing. She was sliding her hand up and down the shaft like she was jerking me off instead of cleaning it. “It's very important to keep your private areas clean, Josh. I hope you clean this well when you bathe yourself.” I didn't say anything because I'd get suds in my mouth if I did.

She kept stroking my dick. I was no stranger to jerking off, but frankly she could have taught me a thing or two. I was getting close to coming and I didn't know if I wanted her to stop or keep going. I knew I didn't get a say in it so I just tried to enjoy it. Her bathing me was so embarrassing, but here I was getting jerked off by a beautiful woman. My friends at school would never believe me.

When I felt my orgasm building and thought I was going to cum in Sam's hand, she slowed down. If she'd just stopped it would have been very uncomfortable and I think she might have known that because she jerked me slower and slower before stopping so it wasn't painful. I still wanted to beg her to keep going.

“There. All clean. Let's rinse you off and get you out of the tub.” She had me sit down and go under the water to get all the soap and conditioner off, then she pulled the plug and led me out of the tub.

I picked up a towel to dry myself off, but she took it from my hand and started drying me off with it. When she reached my crotch it seemed like she took some time to play with it through the towel.

When she was satisfied I was dry she hung the towel up as I stood there still facing her with an erection.

“Uhm, Sam? Can I go get dressed now?”

“Well about that, Josh. There's something we need to discuss.”

“What's that?” I wanted to cry.

“You disobeyed me, which was basically the one rule I gave you. I can't just let rule breaking go.”

“So what are you going to do?”, I asked, trying to keep the fear from my voice.

“Well, that's up to you. When a child misbehaves on my watch I do one of two things. Either I tell their parents-”

“Don't do that!” I yelped. If after all this I got in trouble with my parents and still needed a babysitter in the future I'd go crazy. Sam smiled at that.

“Or, I punish them myself. I'm assuming you pick the second option?”

I felt trapped. I had no way out, except to let her punish me. “I think so. How will you punish me?”

“Well, with my other kids I usually just spank them, but I think you might be too old for that. A little bit of pain on your heinie probably wouldn't teach you a lesson.”

“Oh yeah, I agree”, I stammered. “I'm definitely too old to be spanked, I think. Please”.

“Well I'm glad we're on the same page. Instead I have an idea for a much more productive punishment. I'm going to keep you naked until tomorrow morning.”

“What!?”, I almost screamed it.

“Mhmm. You're clearly very modest, so this punishment will teach you a good lesson. More importantly, I think you're too embarrassed of your own body. You're almost at a point in your life where girls will want to see you naked. It's important you get passed your shyness. That, or you can go get dressed now and I'll tell your parents you gave me a really hard time.”

“I don't have much of a choice, do I?”, I asked.

“That's the spirit!”, she said with her trademark smile. “Now, I'm gonna go change into my pajamas. Luckily you're already in yours. So go wait for me in the living room, I have a movie I think you'll enjoy.”

I went downstairs and sat on the couch. My penis was still almost painfully hard. I considered trying to jerk off really quick, but I decided against it. I made the right call because Sam was there in less than two minutes. She'd changed into her pajamas and was now wearing a t-shirt that went halfway down her thighs, and she was also carrying her purse. It was so long I couldn't tell if she had shorts on underneath. In my head I imagined she didn't.

“Alright, Josh. I don't know what your parents rules on R rated movies are, so I won't mention this to them if you don't.”

“Don't worry, Sam, my lips are sealed.”

“Perfect. I think you'll like this one, it's funny.” She put the movie into the DVD player and then sat on the sofa. She turned to me and said “Come over and sit on my lap, Josh.”

“What?”, I asked, disbelief in my voice.

“Do you need to get your hearing checked? This is part of your punishment. What's the point of you being nude if you're hiding from me? Come sit across my lap, with your back against the arm of the sofa,” she patted the sofa's arm as she said it. “It's soft enough that we'll both be comfortable and it'll let me be able to have a good look at you throughout the movie.”

The thought of that was almost more embarrassing than the bath, but I knew I didn't have a choice. I sat with my bare butt on her lap and my back against the arm of the sofa so I was basically lying down but was reclined.

Once the movie started and I got into it my penis, finally, started getting soft. Apparently Sam noticed because she grabbed my penis and stroked it like she was washing it again until I was hard. It was embarrassing but I liked the feeling so I didn't say anything. Once I was hard again she kept her hand on my penis but stopped stroking it.

She did this throughout the movie. Her hand almost never left my penis, and every time it started to get soft she played with it until it got hard again. I was so horny I thought I was going to lose my mind.

The movie had a lot of nudity, which I liked. Sam noticed too, because during those scenes she kept stroking my dick even if it was fully hard. A few times I thought I was going to cum but she always stopped before that.

Eventually the movie ended. At that point I had been hard for over two hours and was almost in tears I needed relief so badly.

Sam, still holding my penis but not playing with it, said “I think it's almost bed time. We've got a big day tomorrow.” I wanted to cheer. As much as I liked the feeling of her playing with me I wanted to run to my room and make myself cum already. “There's just one thing we need to do first. Sit tight, this will only take a couple minutes.” I didn't know what she was talking about, but she took her hand off my penis and started rummaging through her bag. She pulled out a bottle of Dove moisturizer.

“Your little friend here probably isn't used to this much attention. Let me just put some moisturizer on it so you don't chafe and then we'll go to bed.”

“Okay, Sam,” I muttered quietly.

She squirted a glob of it into the hand that she'd been using to play with my penis throughout the movie and then started rubbing it into me. After about ten seconds it was clear that my penis was thoroughly moisturized, but she kept on stroking it anyway. It felt amazing. Even better than when she was washing me in the shower. I forgot how embarrassed I was because I was enjoying every second of it. Sam was a beautiful girl, I could feel her bare thighs against the skin of my butt cheeks, and was vigorously stroking my cock.

It didn't take very long. I'd been hornier than I'd ever been before for over two hours, and her hand on me felt even better than my own. Sam and I made eye contact and then I exploded. She pointed my penis up and I came all over my stomach and chest.

“There we go,” she said, still stroking me but much slower and gentler now. “I bet you feel a lot better after that.” She took her hand off my penis and gave me a quick kiss on the lips. “Why don't you go wash this off and head to bed? I'll see you in the morning. And remember, no clothes until we leave the house tomorrow.”

“Okay, Sam. Goodnight. And thank you, that was fun.” She winked at me and we both got up. As I walked out of the room I looked back. She was facing away from me and was raising her arms to stretch, pulling her shirt up. It went high enough that I saw she definitely wasn't wearing shorts, and it could have been my imagination but I don't think she was wearing panties either.

(End of File)