Day 27 Orgasm 31

"Come on in, Peter."

He couldn't take his eyes off of the huge dildo. I was laughing inside.

"You said you wanted challenge, right?"

"Uh… Yes ma'am, I did. But I…"

"No excuses, Peter. We've been through this before. Follow me." I walked down the hall with the enormous dildo swinging in front of me. Peter followed.

I locked the door of the dungeon after we entered. A loud click that he couldn't miss.

"Present yourself." Peter undressed quickly, folding each piece of clothing and putting it in a neat stack on the table. He returned to stand in front of me, naked and nervous. I don't think I'd ever seen his cock look quite so uninspired.

"On the spanking bench, Peter." I fastened the restraints around his wrists and ankles and then put a blindfold on him.

"You chose this, Peter. Remember? You asked for this." My riding crop was already ready in my hand.

"Yes, but I… Ow!" I brought the crop down hard on his ass.

"Did you hear me say no excuses, Peter? I meant that."

"Yes ma'am. I understand, ma'am."

I warmed up Peter's ass exactly the way he loves. A little flogging, the leather paddle, some more flogging, the tawse, and finally my riding crop. He was flying high by the time I was done. And his cock was looking significantly more inspired. I chuckled to myself.

"Time for your challenge, Peter."

"Ma'am… I really think that perhaps… I'm not sure that I'm…"

"Oh, Peter." I slipped the ball gag neatly into his mouth and secured it. "You just earned yourself 10 strokes with the ruler. Count them with your fingers, understand?"

Peter nodded his head vigorously, and closed both hands into a fist. I walked over to the cabinet and picked up the hardwood ruler, my heels clicking on the floor. I returned and tapped the wood against one of the supports of the spanking bench. Peter knew that sound.

Smack! One of Peter's little fingers emerged from his fist. Smack! The finger next to it. Poor Peter's ass was pretty red by the time we got to 10, and he was whimpering.

Again, the sound of my heels going over to the cabinet. I picked up a decently large dildo. Soundlessly, I switched it out with the behemoth that had been hanging from my harness. I snapped on a pair of gloves. That was another sound Peter knew. Grabbing the lube, my heels clicked back to the spanking bench, where I started to loosen up Peter's ass. One finger, two, and finally three. He was groaning with pleasure at that point.

"Are you ready, Peter?"

No acknowledgement.

"Don't make me punish you again…" I saw Peter nod his head reluctantly. "Good boy."

I placed the head of the dildo against his well-lubed hole and began to push it inside him. But I went so slowly, that in Peter's mind, I was sure that he still envisioned the behemoth. Millimeter by millimeter, his ass was taking that dildo in, while his mind thought it was much, much bigger than it actually was. The dildo I chose was a tiny bit bigger than anything Peter had taken before, so it was a bit of work for his ass to accept.

Again, with the whimpering. But this time it was from pleasure. It was precisely 10 minutes before I finally had the entire toy sunk in his ass. I was watching the clock. I reached up and unfastened the gag, letting it fall on the floor.

"Mmm. Your ass was hungry today. How does it feel?" I purred the words at him.

"Incredible, ma'am. Thank you!" The emotional quality of his words thrilled me.

"Now you're going to get fucked with it." My tone was stern and no-nonsense. I pulled back until just the head was inside him, thrusting back in to the hilt.

"Oh! Yes please, ma'am!" I could see a puddle of pre-come dripping down the leather of the spanking bench from Peter's heavy, blood-filled cock. He was a happy boy.

Peter didn't last long. The thought that I was fucking him with the behemoth was so damn exciting, he couldn't contain himself. Before I even worked up a sweat, a puddle of come joined the pre-come, and Peter enjoyed a long, loud shuddering orgasm.

I love mind fucks.


(And yes, this fantasy was worth 2 orgasms!)



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