Page 57 of Learning to Trust

“You don’t play fair, Sir.”

"I never said I did. The dildo will be set in position beneath your hole. It will be heavily lubricated and the first inch or so will slide inside while you are on the boxes."

I struggled to see the point. Even though Andrew hadn't said as much, I would be forbidden from having an orgasm, and having only one inch of the dildo, no matter how thick, would not cause much in the way of stimulation. However, my gut told me there was more to this scene and Andrew would not let me off so easily.

After fingering me loose, Andrew slid the dildo inside. It stretched the walls but wasn’t enough. Bending my knees, I attempted to push myself further onto the plastic. Vibration began and the girth became uncomfortable, so I stood tall, and the pressure eased. I had a feeling I was going to be screaming for relief before too long and that caused goosebumps of excitement to break out over my skin.

“Now we get started. Safe word?”

"Monti, but I won't need it, Sir." I doubted anything my Dom did would cause me to safeword out of a scene.

“Very good.”

Using one foot, Andrew pushed the boxes apart and my legs spread. The dildo slid deeper, and I pushed onto my toes to pull off when it became uncomfortable but wasn't particularly successful.

Again, the boxes were edged apart, and I slid further onto the dildo despite being high on my toes. I wriggled and groaned as my ass swallowed more of the torturous device.

The boxes continued to be edged apart, my legs spread wide until my toes barely rested on the edges. I knew if I dropped my feet to the ground the dildo would be forced deeper than any dick I'd ever taken before.

The vibration nailed my prostate over and over. When the boxes were pushed too wide for me to reach, my feet dropped to the ground, and I cried out as my ass took the full length of the thick appendage inside. Even pushing onto my toes gave no real relief.

“Fuck, Sir. So full, Sir.”

“Safe word?”

I shook my head and pulled on the leather binding, hoping to lift high enough to be free of the onslaught, but it was too long to completely escape. My arms didn't hold me up for long and I slammed back down, once again taking the entire length. My dick leaked like a broken faucet, and I raced toward an orgasm.

Andrew had moved behind me and I shouted out when the first strike of the flogger cut across my ass. The vibrations of the dildo became stronger, and I whimpered.

Andrew put his lips against my ear. “Fifteen strikes, David, then I’m going to bend you over the chair and fuck you until you can’t stand.”

“Yes, Sir,” I huffed while wriggling my ass.

“Count them, starting from one.”

“One, thank you, Sir.”

Andrew chuckled. "No, the first one was for bending your knees and trying to escape the dildo when we began."

The flogger struck again.

“One, thank you, Sir.”

Andrew's lips licked the shell of my ear while he gave my cock a few hard tugs that caused my balls to tighten and shrink against my body. "That one was for trying to use the leather binds to pull off."

The leather strips stung as they cracked against the tops of my thighs, and I screamed as they intensified the effect of the dildo when it was hit.

“David?”

“One, thank you, Sir.”

“Fuck yourself.”

I pushed up on my toes and lowered, simulating being fucked. It was exciting my cock to the point I suspected control would be lost.

The next strike had the tails cracking against the right ass cheek and the side of my thigh. I stilled as the sting radiated outward.

“Two, thank you, Sir.”