Riley's Diary: Babysitter Ch. 01

Dear Diary,

The other day I got a call from an old friend. Although she isn't exactly old, or a friend. She usually just calls me when she needs a maid for a day, or is just feeling a bit horny. I definitely need to thank Daddy for introducing us. Anyway, she called me while I was at work and said she had a special task, and that it would be over the weekend. I needed the money, and working for her was fun, so obviously I agreed. When I got home, I changed into my maids uniform and I packed up an overnight bag. I put in some panties, some of my more girly clothes, and some toys for some late-night fun. I got a cab and within half an hour I was outside her unforgettably opulent mansion. I knocked on the door and she swung the door open, in nothing but an open robe. Her cock flung as she opened the door, swaying as she looked at me with her lust filled eyes.

"Oh good! You're here!" She grinned as her cock swayed left and right, letting of her musky scent.

"Yes ma'am! I always cum fast!" I giggled at my own joke, unable to keep my eyes of her massive swaying member.

"Hahaha! Don't I know it!"

She laughed as she grabbed my hand and pulled me into her house. We went along the familiar hallway, although I noticed she had some bags ready as well. Without even saying a word, she threw me onto the couch and grinned as she dropped her robe onto the floor. I just then noticed that her cock was already gleaming with the distinctive shine of lube. She was in no mood to wait or have nay foreplay. I quickly took of my top as she pulled of my skirt. I lay on the couch in just my panties and her on top of me. She smiled as she played with my nipples, flicking one and nipping at the other. I was about to pull off my panties but she stopped me, and instead just slid them to the side and rubbed her tip against my hole. I was already moaning as I felt the cold moist touch of her cock on my hole. She quickly slid in, the lube helping her as she sat up. She held my legs by the ankles as I looked down at her face. Her smile was so bright and genuine, it was obvious she was planning this. She began thrusting her cock inside me. I was already leaking precum as she shook the whole couch. She began kissing my legs and getting faster. I came all over myself and she began playing with it. Rubbing my own cum on my belly and rubbing it on my nipples. I could feel her getting even faster and her cock throbbing inside me. As she threw her head back and let out a groan, I felt her cock pumping me full, making my belly swell. Her hair fell over her face as she finally stopped and looked at me.

"That was great! I needed that before my trip." She pulled out and cleaned herself up.

"A trip?" For a second, I thought she was planning on taking me with her.

"Yes, that's why you're here. I'll be back by Monday night, and I need someone to take care of the place, water the plants, clean the pool, stuff like that."

"Oh, that's no problem at all. I love spending my time here anyway." I smiled and looked around as I began putting on my clothes again.

"I also need you to take care of my daughter, Maddison."

"Your daughter?"

"Yes, I know I look young, but I do have a daughter."

"I- I don't know, I don't think I've ever babysat anyone."

"Hahahaha, bless your heart! She's not a baby. She's actually 19."

"19? Then, why would she need a babysitter?"

"Well..." She trailed off, blushing a bit as she put on her clothes.

"Well?"

"Well, a part of her is still like a baby's. The doctors say she can grow, but she needs more... consistent attention."

"Oh, I guess I could help with that." I was so intrigued. I had never seen a futa that was small.

"I know you can dear! That's why I called you." She smiled as she leaned down and pet my head. Suddenly she pulled down my panties and put on a chastity cage before I could do anything. "Don't worry dear, you can still sissygasm, just don't want you fucking my daughter! She's probably sleeping in her room, take care of the house and her, goodbye!"

I blushed as she walked out to a car already waiting for her. I waved goodbye as I looked down at the cage. It's not that I mind the cage, I just never would have even thought of fucking her with my tiny useless cock. I sighed as I closed the door and quickly began cleaning the couch and the rest of the room. I was watering the plants when I noticed the door on top of the stair's creek open.

"Hello? Maddison?" I quickly looked up and saw her face peeking out of the door.

"Do you want to come downstairs for some food?"

"No!" She shouted and slammed the door.

I was a bit confused at her reaction. I quickly made a sandwich and walked up to her room and knocked.

"Hello? Maddison, could I come in? I have a sandwich for you."

I heard some shuffling in the room and then a meek voice, "It's open."

I jiggled the knob and opened the door. As I walked into the room, there was a heavy scent of musk. It was obvious that she had been jerking off for a while. There were also a lot of rolled up thrown about clothes here and there, making the room look very messy. Maddison was under the sheets, staring at me as I walked over to her. I placed the sandwich in front of her and backed up a little.

"Thank you." It almost sounded like a whisper.

"You're welcome! Can I get you anything else?"

"Yeah, you could leave and never come back!" She seemed mad.

"Excuse me?"

"You heard me. Leave! I don't get why mom makes me hang out with other futas like it's somehow suddenly going to make me huge." She took a bite of her sandwich as she pulled off the sheet from her head, revealing her auburn hair.

"But I'm not a futa."

"Huh? What do you mean?"

"I mean, I'm a femboy."

"Oh, I guess I didn't know that" She seemed a bit embarrassed. "I guess she wants me to hang out with someone the same size as me for once."

"Oh, I don't think you're that small." I lied, still interested in seeing how small she was.

I sat next to her as she finished her sandwich, trying my best to comfort her. She silently ate her sandwich. She seemed to check me out from time to time but didn't say a word until she was finished.

"So you're a maid?"

"Yeah, your mom asked me to help out here while she's away on her trip."

"So you have to do everything I say?"

"Ye- yeah I guess so."

"Good! Take of your skirt and panties! I want to see how much bigger I am than you."

I blushed bright red, but I just had to know, so I quickly got up and pulled down my skirt. The bulging outline of the cage made me look bigger than I was. I looked to Maddison and she had already taken off her PJs and holding them in one hand as she sat with her legs spread open at the edge of the bed. Her cock was smaller than I thought. She was clearly uncircumcised and she seemed a little embarrassed. I pulled of my panties and moved forward, letting my cage touch her cock.

"Wow! If it wasn't for the cage, you would definitely be bigger!" I complimented her, trying my best to perk her up.

She blushed for a second and suddenly became silent as she looked down at her cock. "It grew!" She smiled as it really had grown about half an inch. "I guess I needed more small cock energy around me to grow!" She was absolutely beaming as I felt her cock grow about a half inch more.

"Wow! You're right! You're growing!" I exclaimed but was suddenly cut short by her cumming onto my cage and shrinking again.

"Whoa!" She let out a little moan and backed up.

"I'm sorry! I didn't think it would shrink back."

"It's okay! Look!" She pointed to her cock "Even though it shrunk back, it's still bigger than before!" She was much happier than she was when I entered her room, but she also seemed more tired.

"I'm so glad I could help" I smiled as I stood there half naked. "How about we clean up your room, order some pizza and then watch some TV?"

"That sounds fun!" She smiled and hugged me tightly.

We began cleaning her room. Nearly all the clothes that were crumpled on the floor were covered in crusty cum. She explained later that she had problems controlling her night time emissions. I was glad to help, but I had never seen a futa cum so much in one night. I got a taste of some of the fresh little spurt she left on my cage and it just tasted different, like it was sweater. As I finished up the room and carried out the laundry, she had already ordered pizza. I separated all the laundry and was so tired, I figured I'd finish it in the morning. I headed back up stairs and saw that she had already put the pizza box on the table and was cycling through movies.

"Hey! I was just looking for a movie to watch on Nutflix®, you have anything in mind?"

"No, not really, we could watch a horror movie? Those are usually fun" I sat next to her and noticed my presence made her cock twitch.

"Okay, there are a couple new ones so how about we watch, 'A loud place'?"

"That sounds like it'll be fun." I reached forward to open the box and saw her smile.

"Since you were so helpful, I put some extra toppings on your half of the pizza" She giggled.

I grabbed the pizza, and for a second thought it was just ranch, but it smelled much better. I took a bite and it tasted even better. She scooted closer to me and we watched the film and finished the pizza without any further incident. When the movie was over I yawned and stretched my arms.

"Well, its bed time, want me to walk you to your room?"

"Sure!" She blushed a little, "actually I was thinking, since my clothes aren't clean, and I don't want to ruin my bed, could you..."

"I understand." I smiled as we both got up and walked to her room.

She got into her bed and pulled down her panties. I got in the bed as well, but my face was right next to her cock. It had grown a considerable two inches since I had met her the first time. She got comfortable and gently placed her cock between my lips and grinned.

"Goodnight!"

"Goodnight!"

She was soon asleep and I could feel her cock throbbing in my mouth. She leaked cum into my mouth all night, it was like I was a baby and her cock was my bottle. Pretty soon I fell asleep too, the whole night her cum poured into my mouth and down my throat, I had never experienced something like this before.