≈ First Day ≈

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Dan

Now it was my turn to be nervous. Phil had guided me to his office and was now skimming the papers and when he set them down, there was a mischievous glint in his eyes.

"Dan. My room, end of the hall, naked, by the time I get in there." He said, an authority in his voice that made me shiver.

I nodded and quickly made my way to the room he said and rushed inside, peeling off clothes as I fell onto the bed. Now I had a chance to look around. The bed he was on had ebony black soft sheets much like the rest of the room. There was red LED lights around the base of the room giving everything an eerie glow. I could see shelves full of things that I really hoped Phil would use on me. I was about to touch myself when I remembered that it would result in punishment.

Did I want that? Punishment on the first day?

At first, my answer was no but when I remembered all the things Phil might do to me, the answer was yes. I let out a tiny moan as I began stroking myself and I heard Phil walk in.

"Well, what'd we have here? Already breaking rules?" He growled, slapping my hand away.

He pulled off his clothes and grabbed what I identified as a riding crop.

"Over my knees, now." He said.

I did as I was told and laid my body over his knees, exposing my ass to him. Without warning he smacked me with the crop and I held back a moan. Pain kink huh? Wow Dan, stop being so slutty. Nine hits later, my ass was throbbing. Phil grabbed me and pushed my body into the mattress, securing my hands above me.

He walked over to one of the cabinets and I had to turn my head to watch him. I could hear him shuffling around things before he came back to me with a black blindfold, which was soon over my eyes. With my hands restrained and my eyesight gone, the tension in the room picked up. Soon enough, I felt cold metal slide down to the base of my cock. A cock ring. Great.

The next thing was unexpected. Phil pulled my legs apart and jammed a finger into me, making me cry out. He added another and curled them both, hitting my prostate and pulling a moan from my lips. Too soon, the fingers were gone. I could hear Phil moving around again and I gasped as I felt something at my entrance.

It was so big, and it felt so good. He slowly pushed it all in and just let go, not moving it. The anticipation of something to happen was killing me, making me squirm. I needed something. I couldn't deal with just sitting here.

"Sir, please!" I moaned out.

"What'd you want?" He growled.

"Anything, please!" I begged.

I let out a strangled scream when the toy inside me buzzed to life. He'd positioned it so the tip was nudged against my prostate, sending waves of inescapable pleasure through me. I squirmed around, trying to get some friction from anything, anywhere, but there was nothing.

He turned the vibrator up again, to what I assumed was the highest setting as non stop pleasure coursed through me, making me scream. I was hanging onto the edge, not able to let go due to that damned ring he'd put on me.

"Please sir! Can I cum? Please please please......" I moaned out, my voice fading away.

I felt his hand slide the ring off as he bent down next to my ear.

"Cum, baby."

I let out another scream as I came hard. The world around me felt numb as I came down from my high, one of the best I've ever had. I'd almost forgotten about the toy inside of me until it was kicked up to a higher level, making me scream again.

I struggled against the restraints, trying to pull away from the over stimulation. This was meant to be a punishment after all. I felt Phil slide the ring back on as he began stroking me with one hand, using the other to play with my nipples while his mouth worked on my neck. All the stimulation was bringing constant screams and moans from me until it all became too much, and I blacked out.

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