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The Babysitter Part 2
🕑 Added 2025-04-30 17:50:18 +0000 UTCAs the school year came to a close, I was both looking forward to and worried about Carey being my babysitter all summer. I had to admit, I liked having her around: she was cool and fun and projected a maturity that put her beyond her years. At the same time, the whole arrangement was kind of weird and humiliating. I thought about her height, her self-confidence, and how cool she seemed, especially compared to me. I tried to put her out of my head but she would keep creeping back into my mind once and while.
Eventually, the school year ended and summer arrived. On the first day of summer, Carey appeared at my house around 8:30 in the morning, just before my Mom was going to head to work. I was still in my pyjamas and moving slowly, Carey was in short red shorts and a tank top and looked the part of a 17 year old girl. She wasn’t overly muscular or anything but she was strong and had long legs and thicker arms than me. I could see the difference between her 5’11 and my diminutive size and it made me feel… something. My eyes lingered over their thickness as she came into the house and I thought about the contrast between us. She filled the space whereas I always felt like I was shrinking away.
“Hi Michael!” she said with a wave as she came into the house.
“Hi.”
She and my Mom chatted for a bit in a low tone in the hallway and although I tried to listen in, I could only make out a few words. My Mom was telling her the snacks I was allowed to have, how much video games I could play, and so on. I felt a little annoyed, and it felt somewhat humiliating to be cut out of this conversation but I just moved around the kitchen getting my cereal.
“OK, bye Michael. Be good for Carey!” my Mom shouted and I heard the door shut behind her.
Carey came into the kitchen, leaning against the door frame, and smiled at me, “Hey, how’s it going?”
“Fine…” I said, without looking up.
“Hey, did you want to play some video games this morning?”
“Sure!” I said, enthusiastically.
I looked up at her and noticed her broad smile and decided to just enjoy the day and not worry about my own feelings of humiliation.
We went into the living room and she sat on the floor with her long legs bent in a way that made me feel like she was taking up the whole room. I sat beside her, cross-legged, and felt like a child next to her. We played games together but I would occasionally look down and see the thickness of her thighs – she was just so much bigger than me. It didn’t help that she was really good, which only made me feel smaller. She was so much taller than me that even sitting side by side, it felt like I was looking up to her.
As we played more games, she’d lean over to give me advice, her body pressing against me slightly. Once she killed my character and she laughed, leaning against me and I felt the bulk of her torso, so much stronger than mine. Her size was intimidating, and I strangely found myself deferring to her instructions as though her size and her confidence were reason enough for me to follow her orders. It was strange feeling so small and powerless next to a girl who was younger than me. Every time she’d move or lean over, I’d feel a little more intimidated, a little more like I was her charge.
The day continued like that and we ended up having fun. After a few hours, I asked her if it was OK if I rode my bike over to a friend’s house. She said it was so long as I was back by 3 and I agreed without thinking twice about the rule she had arbitrarily imposed.
I headed over to my friend Dave’s house and told him I needed to be back mid-afternoon. He asked why but I lied, saying I had some stuff to take care of at home.
Dave was a bit of a burn out: a nice enough guy but not particularly going anywhere. I’d smoked weed with him a few times so it wasn’t much of a surprise when he pulled out a bag of marijuana. We chatted as he rolled a joint and we smoked it together.
It was nice weed and I was feeling pretty buzzed but not too stoned.
When I got back, I was feeling a bit floaty, and Carey immediately knew something was up. I went into the kitchen to get a snack and she came into the doorway and looked at me. She loomed large in the frame of the door and the weed was definitely having an effect as I slowly looked up from her large thighs to her midriff to her face. Did she look… older? She looked at me, puzzled, and asked what was wrong, staring at my suspiciously.
I looked down at my shoes and said, “Nothing.”
“Come on Michael. Something is up. You’re acting strange.”
I looked up at her and felt… well, like a little kid who was in trouble. I know she was younger but she was just so much bigger, and her presence and confidence made me forget our age difference. Something about her standing there, filling the doorway, looking down at me that made me want to confess.
“Well, Dave and I smoked a little weed. I think I’m still a little buzzed.”
Her eyes went wide, “You what?!?! You shouldn’t be doing that!! That’s terrible.”
“What? It’s not such a big deal. It’s a little weed.”
“It IS a big deal, Michael!”
She crossed her arms across her chest, her eyes narrowed and she stepped towards me and leaned down so her face was level with mine, “I don’t want you doing that while I’m here. It’s my job to keep you safe and you’re not going to do anything stupid like that again, do you understand me?”
“I--- listen…”
“Do you understand?”
I pushed back: “It’s not a big deal! Lots of people smoke weed.”
“OK, so you wouldn’t mind me telling your mother?”
I stepped back. She was very close to me and I felt… intimidated. I felt small in front of her.
“Come on, you wouldn’t do that. Why would you?”
“Michael, you’re my responsibility. And to be honest, the more I see, the more I realize that you’re not mature enough to take responsibility for yourself. You need someone to direct you.”
I was speechless.
She continued, “You might be older, but you’re far less mature than me.”
She let that hang in the air before continuing. “If you agree not to do it again, I won’t tell your mother.”
“Come on Carey it’s..”
“No arguing. Agree or I’ll tell her.”
I was silent for a second. My Mom would flip out if she knew I was smoking weed. I exhaled, feeling the sense of defeat.
“Fine.”
Carey stood up straight again and said, “Don’t say, fine. Say, yes, I agree.”
I paused before replying, “Yes, I agree.”
A small smile crept across her face, “Good.”
She stepped further into the kitchen and stood close to me before talking. I was eye level with her collarbone and felt the intense contrast between us. I subtly eyed one of her large thighs and thought, it had to be as thick as my waist.
“You know that stuff stunts your growth, right?”
She was standing two feet in front of me, looking down. My only options were to either stare into her torso or crane my neck and look up at her. I slowly looked up into her eyes. I felt intimidated, controlled, safe…
“No, it doesn’t,” I replied weakly.
She raised her eyebrows, “Yeah, it does. It affects you mentally, giving kids anxiety and stress and difficulty in social situations. But it can also stunt your growth.”
I was silent.
“Maybe that’s why you’re so small, Michael? Did you ever wonder?”
I felt a mixed sense of humiliation and arousal as she spoke to me. My heart was racing and I had flutters in my stomach. I was so close to this young amazon and could feel the size difference between us. To add to that, she was speaking down to me, telling me what I already partially knew and I think she was enjoying the power difference between us. I might have been older than her but she was clearly in charge.
“Hey, I’ve only done it a few times.”
“Do you want to stay small forever?”
“I… no…”
“I mean, you’re older than me, but look who’s bigger. Look who’s in charge?”
I was getting uncomfortable. “That’s not because of weed.”
“Isn’t it, Michael?”
She threaded her hands behind her head, exuding confidence. I could see the muscle in her arms flexing as she did so and I felt … intimidated.
There was something animal in what she was doing, showing me her strength, her size, her dominance. Her presence in the room was expanding and I was diminishing.
She continued with a slight whisper, “It’s all the same thing Michael. Smoking weed, acting immature… it’s all holding you back.”
“I… I don’t…” I didn’t know what to say. I felt cornered in the kitchen just like I felt cornered by her arguments. The weed was making my head swim and her size…
“Well if you want to grow up and be as tall as me, you shouldn’t do it anymore.”
My face went red with embarrassment. I felt like a small kid being chastised by an older girl.
“I promise not to do it anymore.”
She placed a hand under my chin and smiled, “Good.”
I hurried out the kitchen, trying to escape her and find a place where I wouldn’t feel so intimidated. She called out, “I’ll get dinner started. You need to eat if you want to grow.”
I watched TV after what felt like an eternity, she called me into the kitchen. The table was set with plates and silverware and she had even folded a napkin into a little square. She had made spaghetti with a side of garlic bread. The sight of it made my mouth water.
“Come on, Michael. Dinner’s ready.”
I sat down, looking at the plate of food that was placed in front of me. It felt like a form of punishment, like she was feeding me because she had to, not because she wanted to.
“Eat up, it’s good for you,” she said as she sat opposite me, with a smile.
The conversation was good and we seemed to be friends again. When my Mom arrived back at the house, Carey left with a smile and a wave.
The next morning, she arrived just as my Mom was stepping out the front door. Carey was wearing tan, khaki shorts and a white t-shirt and was carrying a backpack. Her thighs looked thick and strong and I did my best not to fixate on her powerful legs.
She came up to me in my room with a smile, “Morning! Hey, can I ask you for a favor?”
I smiled back, “Sure. What is it?”
“I was going to ComicCon later this week with my friend Sarah and we were going to dress and Chun Li and Sailor Moon but Sarah’s sick…”
“And?”
“Well… will you go with me?” she raised her eyebrows hopefully.
I thought about it for a second and decided ComicCon would be fun, so why not.
“Sure.”
“Thanks but that’s not the favor… I need someone to dress as Sailor Moon.”
My eyes went wide. “Are you kidding? Absolutely not!”
She put her hands on her hip. “Come on. What’s the big deal?”
“What’s the big deal?!?! I’m not dressing like that! In a skirt! Like a girl!” I shouted.
She crossed her arms over her chest. “You act like it’s such a bad thing. Lots of guys dress in drag when they’re in cosplay. Girls too. It’s not such a big deal.”
I backed away from her, “No way. I’m not doing it. Besides, why would I?”
“Well, Sarah is basically your size and the costume would fit you perfectly.”
She stepped behind me and I could feel her looming over me, taller and bigger.
“No way! Not a chance.”
“Would it make you feel better if I dressed in drag too? I could dress as a guy.”
“Um… NO. That would NOT make me feel better. Forget it.” I turned away from her.
She ignored my protests and continued, “How about this? What if I could dress you so well that no one would know you’re a boy? You would look just like a real Sailor Moon?”
I turned around to face her but found myself staring at her neck. I stepped back and craned my head to look up at her.
“Are you kidding?!? I don’t want that. I’m not doing it.”
I began to step back but she put a firm hand on my shoulder, stopping me in my tracks. She didn’t look especially strong, but she was clearly stronger than me.
“Michael, come on. You can help me out with this.”
I pulled away, “No I can’t!”
“Well, didn’t I help you out by not telling your Mom about you taking drugs?”
She wouldn’t… “You promised you wouldn’t say anything! It’s not drugs… it’s weed. It barely counts.”
“Weed is still a drug, Michael.”
“Come on, we had a deal!”
She looked at me sternly. “We didn’t have a deal. I just agreed not to tell your Mom. Now we’re making a deal. Do me this favour and I won’t tell her.”
I was silent.
“You don’t have a choice in this Michael. Do as I say or I’ll tell her.”
I felt cornered, cowed, and scared. She had thought of everything. What choice did I have? It kept happening – she pushed me into a corner, and I agreed to what she asked. She just seemed to be in control all of the time.
Standing in front of her, with her in command of my life, I felt small and insignificant. In her shorts and white t-shirt she looked thick and powerful – it was hard to imagine that I was almost two years older than her. Even more, she was confident and assured where I was weak and unsure. She had taken command of the situation and I had no choice except to follow her instructions. I swallowed.
“OK, if you insist.”
She smiled at me, “I do insist.” Then, changing her tone, “Come on, it’s going to be fun. Let’s see you try on the costume.”
“Now?”
“Yes, now. Come on!”
She handed me the backpack and told me to try on the clothes. “I’ll go and get changed in the bathroom” she shouted as she walked down the hall. “Don’t delay Michael!”
I begrudgingly opened the backpack and looked at the contents. First I pulled out a white blouse with a red bow attached at the front, then a pair of right boots that looked like they would come up to my knees, then a blonde wig with two ponytails at the back, and finally, a short blue skirt. I held the skirt in my hands… what had I got myself into? Was I actually going to do this? My heart was racing and my hands were sweating with anticipation.
As if predicting my doubts, Carey shouted from the bathroom, “Hurry up. I want to see.”
I slipped off my boy clothes and put on the white top and then pulled up the skirt. I couldn’t believe how short it was, I could feel the air through my boxers and it barely covered my ass. Finally, I stepped into the boots – they fit perfectly. I looked at myself in the full length mirror and was surprised at how well it all fit. I looked like a boyish Sailor Moon. My size fit the character – my legs were already smooth and thin – I actually looked pretty good!
I was shook out of my reverie when Carey cracked open the bedroom door and peered in before opening it completely.
“Oh, wow, you look amazing!” she exclaimed with glee as she stepped through the doorway.
She looked incredible herself and we were a study in contrasts. She was in a Chun Li outfit with the blue, silk warrior dress slit on either side: her long legs looking thick and strong. Her hair was in a dual bun in the style of the character, complete with chop sticks, giving her an intense and severe look. She was wearing white boots with a heel that easily brought her to 6’ tall. Her costume had padded shoulders and cut off sleeves that emphasized her upper body strength and size but also gave her a look of confident svelteness. I noticed the thickness of her arms in the costume. My heart was pounding at the situation… what were we doing?!
She walked across the room and stood behind me: towering over me and I felt like a small girl in front of a large, powerful woman. I glanced back at the mirror and saw myself as a picture of demure femininity in my school girl outfit with red boots and white blouse. The short skirt added to my feeling of vulnerability and barely covered by pale, thin thighs. My legs were thin and reedy, truly girlish, and my eyes moved from my slip of a body to the thick pillars of her legs that extended out on either side of my reflection. I felt weak, exposed, and feminine.
She moved closer to me in the mirror, her small breasts even with my head. “You forgot one thing,” and with that she reached into the bag and placed the blonde wig on my head, styling it so it sat securely on my head.
“I… I’m not sure about this, Carey.” I said, looking back at my self in the mirror.
She was so tall I couldn’t even see her face, just the tower of feminine strength that stood behind me, dwarfing me and taking control of the situation.
“You look so good!” she said. “Honestly, you look even more like Sailor Moon than Sarah. Sarah is a little too… I don’t know… big. You fit the costume perfectly. Once I help you with the makeup no one will ever know you’re a boy.”
“Makeup!?!” I exclaimed.
“Of course. You can’t go without doing your makeup.”
“Come on…”
She didn’t acknowledge, my protest, but continued, “Also, you know, you can’t wear that costume with regular underwear.”
“What do you mean!?! Why not?”
I turned to look at her. The combination of her height, the severity of the costume, her strength… My eyes were drawn to her arms and I could see the faint outline of a muscle in her forearms. I had never had strength like that. How could she be younger than me when I felt like a child?
She smiled down at me, like an adult comforting a scared child: “Well do you want people to know that you’re a boy?”
“No…”
“Then you need to put these on,” she held up a pair of white pink girl’s panties.
“I… I… can’t..”
“Come on. What’s the big deal. You totally can.”
“I…”
“If you had worn a skirt before, maybe you’d know how to walk, how to move, how to bend over, so no one would see what’s underneath. But you haven’t ever done this before… have you?”
She asked the question with a raised eyebrow and a broad smile.
“NO!” I replied.
“That’s what I thought. So then you are for sure going to show a little bit of underwear. If you want people to see your boxers and see that you’re a boy, wear those. If not, you need to wear these.” And with that she handed me the undergarments.
“Come on, quickly now. Just slide off the boy underwear and slide those up your legs. Good boy.”
I was too defeated to argue and I saw her amused smile grow as I took the panties from her.
“I’ll look away,” she said with a smile and turned back. I saw that the back of the dress was cut away and her back looked wide and strong. Not overly muscular, but she was far bigger than me.
I sighed, and quickly slid my boxers down my legs, almost falling in the feels. I then stepped into the panties and slid them up my legs. They were surprisingly comfortably although they pulled my penis and balls into a bit of a tight package and ensconced my ass. It was weird – if I felt exposed beforehand, now I felt completely humiliated. But there was something erotic about the experience and as I surveyed myself in the mirror, the blonde wig, the feel of the panties around my dick, the skirt, and the blouse… there was no question: I looked like a cute girl dressed as Sailor Moon.
“OK, I’m ready,” I said.
