"Do you trust me?"
Paul asked me that one day after I had been seeing him for a few weeks. I remember being slightly confused at his question, considering I was laying on his bed in nothing but a jock with nipple clamps pinching me, causing my dick to throb in pleasure. "You know I would never do anything to hurt you, right?" His eyes held mine steadily, a look I would see more times in the future associated with the same question. The look said that he was serious, and that he expected me to understand the difference between, say, the pain of playful spanking, and the pain that went too far. This was the dominate side of Paul coming out.
I'm sure to many fourteen year old boys, the situation would have been frightening. But instead, the threat of the unknown and possible danger made me excited. I looked up into his serious eyes and I nodded my head. I said, "Yes." He leaned over and kissed me, then rolled me on my front in doggy position. Then he went to his toy chest and pulled out a few items. There were four cuffs, two of which were attached to a long pole. I had been looking at porn online long enough at this point to know what the cuffs were used for. The long pole would go between my legs and the other two cuffs would hold my wrists together. Then there was a hood that had no eye holes. That, I knew, would go over my head.
There was a part of me that unclenched seeing these objects and knowing what they were used for. I felt fear I hadn't known was building inside of me as it rushed away. I was calm. He cuffed my ankles, the bar forcing my feet wide. He cuffed one of my wrists then pulled the cuff around one of the bars at the head of his bed and cuffed the other. Then he put the hood over my head and I couldn't see anything anymore. He pulled my head back and I felt his mouth on mine. I blindly tried to kiss him back.
Then just like that he let go and was off the bed and I felt no sense of him touching me. I was blind and could only feel the chains hanging from my nipples. Then from off the bed I felt his hand brush my back. I shivered at his touch, squirming in the bonds. Then again I felt him brushing my sides, tickling and startling me. And then his hands moved to my cock and my ass, caressing and probing. And then gone.
The next thing I felt was a hard smack on my ass. It didn't hurt so much as surprise. More slaps followed until I was sure that my ass had red hand marks all over it. The accumulated hitting did start to sting, but it never reached a point of unbearable pain. Never came close. Instead, Paul began licking my stinging cheeks, wetting them in his spit before moving to my hole. While he tongue fucked me he pulled on the chain between my nipples, causing me to moan. He put two fingers in my mouth and told me to wet them so he could fuck me with them.
Being worked over while cuffed like this was hot for me. Paul knew I would like it. I had indicated to him that I enjoyed watching more hardcore bondage porn. Something that I have always thanked Paul for was his willingness to show me everything that I was interested in, usually without me having to ask. And he could get into character very well. I remember him saying dirty things to me while he fingered my hole and milked my cock. In the darkness of the hood I could only feel and hear and both those senses were in overdrive. Finally he slid his cock in and fucked me until he came inside of me. He kept milking my dick and slapping my ass until I shot straight down onto his sheets.
When I recovered from my orgasm he pulled the hood off my face. His smile told me that I had done very well and that we would get to have more sessions like this in the future. He didn't even have to tell me how good I had been, I knew. I felt the marks of my skill as a sub on my body. And from the way I quickly recovered, I knew that I had been right to trust Paul. I knew that no matter how far into dark places I traveled with him, he would never let me get hurt. And I had some wild adventures ahead of me.