The Secret Side of The BAU

Skye's Training Continues

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.