CM Fanfic Ch 6

After that first time exploring anal play with Derek, that became all we did for about 2 months. Once his fingers weren't enough, we tried other things like the end of my hairbrush, a couple Expo markers, etc. Just different ways to use my hole.

Then, Daddy bought me a plug. He made it mandatory for me to wear it at least 4 hours a day. That was my favorite thing we had done at that point. It felt so good. I could feel it inside me every time I moved.

Thankfully, Daddy was a little more lenient with me on my 'no orgasms without permission' rule during my anal training. Sometimes it was just so overwhelming and felt so right that I couldn't stop my pussy from reacting and I would cum. But, Daddy never got mad at me. He actually praised me. Told me it was beautiful the way my body responded to being used. He told me he loved watching me become so unable to stop what my body needed that I just had to succumb to it. Told me it turned him on knowing that my body knows its place.

Then, last week was the first time I tried a dildo. Daddy told me it would be better for me to ride it because then I could control how much I was taking. So that's what I did. It was a relatively small dildo. The smallest one Daddy could find. But I was still scared.

Daddy held my hand in one hand. Then, he held the dildo steady for me with the other. He told me to look at him as I straddled it. He made me focus on him, not the fake dick I was about to try to sit on. I slid down as slow as I could. Finally, I felt the plastic head touch my hole.

"You're okay, baby. Daddy's right here, remember? I would never let anything happen to you. I made you that promise on day one and I intend to keep it. Just look right here at me. You're such a good girl. I know you can do it."

His whispers calmed me enough that I could let the head push against my tight hole. I knew I wanted this, but it was still new territory and I wasn't sure my hole would be able to handle it. But, with Daddy looking at me with so much praise and hope in his eyes, I couldn't resist trying. I had to give it a shot. So, I took one big deep breath and let the bulbous plastic head of the dildo breach my tight ring of muscle.

That big deep breath quickly turned into a high pitched whine in the back of my throat as I felt my body stretching to accommodate the width. It felt like it would never pop through. Then, with all the courage I could muster, I pushed down and forced the rest of the head into my hole. It felt bigger than anything I'd done up to that point. Way bigger than Daddy's fingers or the hairbrush or the markers. Even bigger than the plug Daddy made me wear. It felt like the head of this dildo was stretching me to my limits. I took a few more deep breaths and wiggled around a little. Trying to make my body adjust and accept the intrusion.

I looked into Daddy's eyes and he was so proud. He had the biggest blinding white smile on his face. I knew I couldn't disappoint him now. I needed to see how far I could take this dildo. If I couldn't do this, I'd never be able to do anal with Daddy and that was like a shot to the gut. The one way Daddy hadn't been able to have me yet. But he'd been so patient with me. I knew I had to keep going. I was his and I had to do this for him. It wasn't even about what I wanted at this point. (Believe me, I definitely still wanted to try double penetration deep down in my heart.) It was about making Daddy proud of me. It was about not being the one to take that smile off of his face.

So with a newfound determination, I gripped Daddy's hand a little tighter as I spread my legs a little wider and pushed my hips down again. This time I took about an inch of the shaft. I gasped and gritted my teeth against the intrusion. Daddy gasped, too. His gasp, however, was followed up with a whispered 'God this is so beautiful to watch.' I ground my hips on the fake dick a few times. Willing my body to keep stretching. Wanting my body to like what was happening. But so far, it was just uncomfortable.

I gave myself a few more moments to relax. Finally, I felt my pussy flutter and my ass relaxed. It started to feel good. So, I lifted my hips up a bit and slid back down. Starting to fuck myself on what little bit I had taken inside me. Those pained whimpers from before gave way to beautiful moans now. I wasn't even thinking, I was just talking. It felt so good. I was already blissed out. At this point, I knew I could do this. So, I forced my body to slide down a couple more inches. It didn't hurt as much this time. My body started to like it. My pussy getting wetter. The butterflies in my stomach fluttering harder.

I was losing my breath, but it wasn't a bad thing. I was overwhelmed with the beauty and excitement of finally reaching this point. I was an anal virgin when we started my training and I never thought, despite what I wanted, that I'd actually reach this point at all. I started to tear up as I fucked myself. I was almost halfway down the shaft at this point. I chanced a glance down to see the dildo inside me and I gasped.

"Daddy" I whispered.

"Yes, sweet girl?" He responded with a smile.

"It's… it's beautiful. I'm doing it Daddy!" I giggled, and he nodded back at me as he reached over to wipe the tears from my face.

"Yes you are baby. You're doing so good. Daddy's so proud of his perfect little girl. Keep going baby. You're almost there."

He pressed a whisper of a kiss against my cheek, but it was enough to keep me going. I pushed my hips down another inch. And then eventually another. After quite a few long moments. I felt my hips and my bottom meet the bed. I had taken the entirety of my first dildo. I raised my hips and started to fuck myself deeper than I'd ever felt anything before. I couldn't stop the moans from escaping my lungs.

It was my favorite thing I had ever experienced and I knew this was what my body was meant for. I needed to keep going on this journey. Soon, I was screaming to the heavens about my overwhelming need to cum. I was gonna explode. Then, Daddy did something I never expected. He laid down on the bed, putting his face where my pussy was. And then he gave me the go ahead. He told me to cum on his face.

I fucked myself on the dildo a few more times until I couldn't stop myself. My pussy fluttered and opened and that was it. Daddy didn't even have to touch me, and I was screaming through my release as my hips continued lifting and dropping. I watched as my orgasm splashed across Daddy's entire face. Not a single inch was spared. I came so hard.

He was still laying there smiling as I came off the high. He was so proud of me. I could tell. Once I could move, I climbed off the dildo and laid next to Daddy. I laid random soft kisses to his chest as we laid there in silence. Then, my giggle sounded through.

"Whats so funny?" He asked.

"When can I try a bigger dildo?" This time I erupted into full belly laughter. And so did Daddy. Then he got up to clean his face before climbing back in bed for cuddles.

Throughout the week, Daddy had been testing me. Letting me get used to a certain size dildo before switching it out the next day or the day after. It seemed like after that first dildo experience, Daddy no longer wanted to take things slow. He wanted me to push my limits and always keep striving to stretch my ass. At the end of the night, when taking out my plug before we'd start using the dildo, sometimes Daddy would just stare as my ass clenched down on nothing. It was like my body was becoming desperate and needed to constantly be filled. He loved it and, in turn, I loved it.

It's a Friday night now and it's not a typical play day for us but Daddy had texted me that morning that he didn't want to stop my training when things were going so well. He had bought the next size dildo and I was ready to try it.

So that night after work, we're back in his home bedroom. The place where this whole thing started. He had picked me up and carried me on his hip up here and then gently laid me out on the bed. I hadn't taken a dildo as big as him or bigger yet, so I knew that was the next step. And when I saw the dildo I would be trying to ride, my eyes got huge.

But, Daddy knew I could do it and he instilled that confidence in me. While I laid down, he teased my body a bit. Starting with kissing on my neck and chest. He ran his hands all over my skin, leaving goosebumps in his wake. He reached down and shoved two fingers quickly inside my pussy and started to finger me hard. While he was fingering me, he circled the head of the dildo around my fluttering ass hole. Letting my body know what was about to happen.

Then, he removed his fingers and helped me sit up on my knees. He set the dildo between my legs and looked up at me smiling. Being that this dildo was pretty big, Daddy lathered it in lube first. Then, he gave me the okay. I knew that I couldn't go too slow but I also couldn't go too fast. So, I took a big deep breath and slid myself down until I felt the plastic nudging my skin. I couldn't psych myself out now. I had to do it. So I quickly closed my eyes and pushed my hips down until I felt the burning stretch of the head popping through.

"Fucking shit!" I screamed, breathless.

"I know it stings baby. But try to keep moving. The only way your body is going to acclimate is if you keep going. Fuck yourself, pretty girl. Let me see how much my baby wants this."

With Daddy's instruction in my ear, I do as told. As if my body is working on instinct, my hips start to lift until the head catches on my rim. So, I slide back down, and challenge myself to immediately start taking some of the shaft. It burns and tears are stinging my eyes, but I know eventually my body will stretch and this will be enjoyable. With every few bounces, I'm taking more and more of the shaft in my hole.

It feels like an eternity, but I chance a glance down and I'm taking half of this massive dildo up my ass. It was at that moment that my body had the realization that it enjoys this and again, just like the first time, my hole started to stretch and I could feel my pussy tingling. I vaguely clued in to Daddy softly rubbing my back. The moans started to reach decibels unheard of in the human realm as I forced my body to keep taking more of this fake plastic dick.

It seemed like it all went so fast after that. It felt like I lost track of time. All I know is that one minute I'm barely taking half of it, and then next I'm screaming through an orgasm as my bottom meets the bed sheets again.

"Did I do it, Daddy? Did I make you proud?" I manage to whisper to him as the tears stream down my face.

He wipes them away and then pulls me to him in a hug I hadn't expected. "Yes, babygirl. Daddy is so very proud of you. Now, get ready for things to really heat up. Now that you can take a cock Daddy's size up that once-virgin hole, Daddy's about to have a lot more fun with his baby.