He crossed to the left side of the bed and sat beside me on my right side. He reached out again and touched my chest but this time it was a rubber tipped finger that he ran from my sternum to my belly button then down to my underwear. He stroked me several times then stopped and moved an none gloved hand to my right nipple.
I felt his flesh as he pinched at it. I heard a hinge being worked and then slowly he attached a clip to my nipple. The pain was instant and lasted for a while before it dulled.
I managed to barely make a sound until he touched the clamp again this time sending pain through my skin and deep into my chest. I let out a yell and a moan.
“Ever thought about this?” he asked.
“No,” I said.
He pulled at the clip.
“No sir,” I said.
“What about those times you used to snap yourself with a rubber band?” he asked.
“That was different sir,” I said.
“You weren’t so powerless,” he said. He moved across my chest tracing a path with his rubber tipped finger to my other nipple which he played with using his fingers until it was hard and then he attached the other clip.
He repositioned himself on the bed, leaned on his elbow in a casual way as if we were having a conversation. He asked me how my cock was doing before he reached down into my underwear where we both felt his hand slide up and down my slick cock.
“You bought condoms,” he said. “How many times can you come in a day?”
I was distracted by the sensations and it took me a moment to find my voice.
“Five times sir,” I said.
“Good, I want you to try and beat it tonight,” he said.
“Really?” I asked.
He pulled his hand from my cock and flicked one of the clips sending pain through me.
“Sorry sir,” I said.
“Would you try if I wanted?”
I thought about the question. There I was tied down and at his mercy yet feeling very safe. I had known him for many years.
“Yes sir,” I said.
“Good, but maybe not tonight,” he said, “after all we don’t want you worn out for the weekend.”
He touched one of the clips and toyed with it then he went back and forth between them until I let out a moan of pain.
“Did you bring more underwear?” he asked.
I swallowed because I was starting to feel thirsty.
“Yes sir,” I said.
“Good because I’m going to have to cut these off and add them to my collection,” he said.
I felt him get up and feeling better about my situation I didn’t need him to talk to me even though my nipples were still hurting. I heard him pick something up from a desk then walk back to me where he placed one knee on the bed and grabbed at my underwear as if it were an annoyance.
He stabbed into the fabric with a knife point then cut at the material until he had cut both sides around the hip including the elastic band. He pulled my underwear from between my legs and under my butt.
I felt them leave me and a new air around my stiff, dripping cock. I was finally naked. He reached up to the clamps and I was afraid he would play with them again but he took them off at the same time.
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