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Chapter 386 - Riley's Diary: Babysitter by RileysMind

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 Butler for a day, or is just feeling a bit horny. I definitely need to thank Mommy 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 Butlers uniform and I packed up an overnight bag. I put in some panties, some of my fetish 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 pants. 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. "Don't worry dear, you can still orgasm, 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 my cock. I just never would have even thought of fucking her with my cock. After all it had been years since I last used it. 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 people 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.

"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 butler?"

"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 trousers. 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 cock touch her cock. 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 cock 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 coco 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. 

 ------X------ 

Dear Diary,

The first time I saw a small futa was crazy. It was even crazier that I was the one helping her grow. It was definitely one of the crazier weekends of my life.

When I woke up, her cock was much harder than last night, and to no ones surprise, much larger. It was still in my mouth, and leaking profusely. Overnight my belly had swelled up to the size of watermelon. I was still a bit drowsy as I woke up to her pubes in my face. I pulled out her cock from my mouth, carefully licking up any drops of cum that might fall onto the bed. She looked so peaceful as she snored away, a part of me didn't want to wake her up, but I had to.

"H- hey, you up?" I gently rubbed her shoulder.

She rubbed her eyes and yawned, " Ya- yeah, I guess now I am." She giggled sleepily and stretched her hands.

"Well, it seems you have grown a bit over night!" I giggled as I held her cock in my hand.

She shot up and looked at her cock with awe, "Wow! It's so much bigger now! All thanks to you!"

"Yeah! Now its almost like 4 or 5 times bigger than mine!" I gently rubbed her cock, smiling at her and then looking at her cock. "Although, I think we both need a shower" I said vaguely pointing to the room and cum covered bed.

"Yes! We do..." Her voice suddenly turned from excited to embarrassed.

"What happened? This is a good thing!"

"It's not that. I love that my cocks bigger, but..." She points to her newly grown pubes. "I think I need to wax now too"

"Oh, don't worry about that. I can help you shave, I do it every day!"

"Really?! Yay!!" She yelled as she got up and hugged me tightly, making her cock rub against my chest. 

She smiled as she stood up and rubbed her cock against mine. I tried my best not to precum. I was wrong, she was at least 6 times as big now. We both smiled and she hugged me tightly, rubbing our cocks together.

"Thank you so much! Now let's go!"

We both got up and went straight to the bathroom, I took off all my clothes and so did she. I turned on the shower and let the water get warmer as I brought out the razer and some shaving cream. She blushed and seemed a bit scared but I tried my best to reassure her by showing it on myself. I fizzed up the cream all over my legs and pubes. And showed her how easy it was.

"See! It's nothing! I do this everyday to make sure I'm all nice and smooth." I giggled as I tried to hand it to her.

"N- no! I don't think I can do it!" She panicked, pushing me away while blushing.

"Do you want me to do it? Would it help you get more comfortable?"

"I- I think it might." She tried to smile, getting a bit more comfortable with everything happening.

I helped her sit on the toilet after closing the lid. I got on my knees, close to her cock. It took every bone in my body to fight the urge to suck her cock. I looked up at her after applying the cream to her pubes. She smiled, clearly more comfortable. I gently grabbed her cock, which instantly got bigger and harder. It seemed she was enjoying herself. I slowly slid the razer downwards from the top to the base of her cock and looked to her again. She flinched a little at first but since it didn't hurt, she smiled back. I handed her the razer and she quickly finished up.

"See! Was it really that bad?"

"No! It was quick and easy!" She grinned from ear to ear. She stood up and looked down at her cock, she shook her hips from side to side as she smacked me in the face with her cock, letting me feel her now smooth shaft. "Do you like how it feels?"

"Yeah I do! It feels so smooth now!" I grabbed it and ran my finger all around it as her cock precame over my chest. I looked down and giggled, "I think this is our sign to shower now."

We both giggled together as we both got into the shower cabinet. It was big enough for three or maybe even four people. The cabinet was getting steamy from all the hot water and the water poured down from the ceiling shower. We were both wet, and both of us were precumming and dripping all over the floor as it slowly drained out. She grabbed the gel soap and poured some into my hands as she cleaned herself up. She was repeatedly touching her pubes and cock, feeling how smooth it was and smiling. She poured some more into my hand and turned around, pointing to her back. I rubbed her back, getting it nice and soapy. She did the same for me, getting me nice and clean. We were both covered in soap and slippery as we played around. Suddenly she grabbed my waist and got close to me.

"I want to feel your butt!" She giggled and whispered.

"Of course!" I giggled back, turning around and bending over a little.

She laughed at how immediately I listened to her. And grabbed my cheeks, squeezing my cheeks and playing with them, getting rougher. I heard her moan and then her hard cock, now even bigger, touched my balls.

"Is everything okay?"

Her voice was now a bit meeker "I- I want to do... more"

I giggled and bent over more, pushing my ass up as well as I held the bathroom wall. "Well, I am your servant and have to do whatever you want to please you." She couldn't tell but my cock was already cumming just from her tip rubbing against my balls.

She laughed out loud as she grabbed my waist and rubbed her cock against my hole, "It's been so long since I've had some boipussy! Are you ready?"

"Yes I am." I whispered, my voice beginning to wane as I felt her tip already prodding my hole.

She let out a little moan as she pulled herself into me. Holding my waist tightly, she slowly slid onside. Her soapy wet cock gently made its way into me. It rubbed against my prostate and made me moan out loud. My moaning gave her more confidence and motivation as she began gently thrusting into me while simultaneously pulling me back onto her cock. She reached down and grabbed my tiny little cock and began playing with it as it dripped cum. I could feel her leaking inside me, my belly was still swollen up from the morning but was getting even bigger. She pulled me back and bit my neck, while her breasts rubbed against my back. She was bigger and harder than ever before and her cock was throbbing. She pulled me back further twisting me as she began cumming inside me. Filling me up to the point that I just couldn't take it anymore and all her cum began pouring out once she pulled out her cock. Unlike most of the other futas that fucked me, her cock wasn't limp when she pulled out. She turned me around and gave me some soap.

"I- I'm beginning to prune. We, we should get out soon." She huffed as her cock began getting softer. She smiled as we both quickly cleaned up and grabbed our own towels and headed out to her room. As we changed our clothes, I got a call from her mom.

"How's my daughter? Is she eating well?"

"She's great! She's eating well and she just bathed. You should also know, she's grown!"

"Really?! That's amazing! I thought hanging out with a futa addict bitch like you might help. Hahaha! How much has she grown?"

I looked at her, noticing how much bigger her cock was now as she dried herself off. "I would say she grew about 6-7 inches."

"That is perfect! I hope you help her get even bigger! I have sent some money to your account, and some numbers to your phone. I want you to throw a small party for her and her friends. This is worth a celebration!"

"Wow! That's great! You are an amazing mother!"

"And you are a perfect little bitch boy!"

Click! She ended the call and I quickly checked my phone for the money and numbers. It was more than enough for a party for the few other people she had coming. Before I could call or text anyone, I suddenly felt my ass get smacked by a wet towel. I jumped up and rubbed my cheeks and turned to Madison. She was smiling as she held the towel.

 She smiled as she saw how girly I looked and that's when I told her about the party. She got very excited, knowing she would be the guest of honor. The next thing we know, were already heading out to get the party supplies. The whole time I had to be in public, showing my bare ass to nearly anyone who would give me a second glance. I even got some numbers from some older futanari that day. We got home and set everything up. I even got a special gift for her with the money I was given. She was so full of energy the whole day but by the time we got back, she was tired and half asleep. She had also gained more control over her leaking but was still unsure about her control. This time when I walked her to her room, I planned on leaving and crashing on the couch. As I was closing the door, I suddenly heard her voice pipe up.

"Hey wait!"

I opened up the door again, "Is everything okay?"

"Aren't you going to stay?"

"I thought maybe you could handle it better n-"

"No! Come back here and be a good Butler!" Her voice was full of anger and I immediately ran over to her and got under the sheets.

"Good Butler!" She patted my head as she stuck her cock into my mouth.

This time her cock felt different. It was rougher and harder this time. Her cock was definitely much much bigger than this morning. It seemed like spending time with me made her larger. She also seemed more angsty and kept tossing and turning, until she found the perfect spot. She lay flat on her belly with her cock now going down my throat. I'm not sure if she was awake or asleep, but her next move was to fuck my throat. She kept thrusting for nearly 15 minutes before finally cumming and stopping her movement. She was definitely leaking less, but her much bigger cock hurt my throat. It was almost like she realized it and pulled her cock out enough to let me be able to breath. I huffed and panted, my own cock cumming until I fell asleep.

 

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