Riley's Diary: Babysitter Ch. 02

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 noones 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. "But before that, I have a little surprise for you!" She smiled as she pulled something from under her pillow and grabbed my cage, opening it up with a spare key. "I don't know why mom even tries to hide the keys, she always forgets, and I find them! But more importantly, we can now compare!"

She smiled as she stood up and rubbed her cock against mine. I tried my best not to precum after being caged for a whole day. 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 maid 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 sissy little dick 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 ana 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 was wearing a tight pink top with a skirt and no panties so her cock was hanging between her legs. She throws some clothes at me.

"You and I are going to twin today!"

I looked at the clothes, they were identical to hers, but they seemed much tighter. As I held them up, I heard the familiar clicking sound of a cage. I looked down to Madisons smiling face.

"You had your fun, and I don't want to get in trouble with mom."

I quickly put on the clothes she gave me. The shit was especially tight and the skirt was very short, just barely enough to hide my cage. 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 and cage to nearly anyone who would give me a second glance. I even got some numbers from some older men 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 maid!" Her voice was full of anger and I immediately ran over to her and got under the sheets.

"Good maid!" 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 tiny cock cumming until I fell asleep.