[Fiction] A willing boy's first whipping.

[m55uk4younger]

John's Story of discovery


He slowly led me down the stairs into the basement and my anticipation grew again to a point I had never felt before. When I reached the bottom, he lifted up my blindfold for a moment, just to let me see where I was going to be "taken" for the first time. I noticed the chains hanging from the roof, as well as a wooden cross and behind them what reminded me of a gymnast's horse.

My blindfold was repositioned over my eyes again and I was led to a spot in the middle of the room. He then took off my shirt and inspected the body he had been given. I must have met his standards because he then proceeded to remove my jeans and underwear shortly afterwards. Just being naked in front of another man, whom I couldn't see by the way, was so hot that my cock was standing at full attention.

Next came my first steps into the world of BDSM, my first set of restraints, and my favourite part, a collar. I felt his arms bring something behind my head and rest on the back of my neck. When I felt the cool leather and heard the buckle I knew instantly what he was putting on me, as I had told him online earlier in the week, that the idea of wearing a collar turned me on. I was so happy with the fact that he remembered and was willing to indulge my fantasy that I had the biggest, stupidest grin on my face as he tightened my collar around my neck. When this was in place, he took my right hand, slid it into a leather cuff, and tightened it around my wrist. This was then repeated with my other wrist, as well as both of my ankles. The feeling of leather around my wrists and ankles was something I had never experience before, but I found myself strangely aroused by the feeling that I could be restrained at any moment, and wouldn't you know it, in about half a second, I was!

My wrists were soon hooked up to the cross and my ankles were held apart by a spreader bar. This was one of the most erotic feelings of my life, feeling helpless, and at the mercy of this big, strange, bear of a man that I had just met half an hour ago. Then the fun began. First I felt a thin wooden cane brush against my ass and almost instantly I knew what was coming, and apparently, so did my dick cause he wouldn't sit down. It began lightly with some tapping and brushing and then with one swift stroke, the real spanking began.

I was in a state of semi-shock, as I had never been hit that hard on my ass at any point in my life, even as a child. The sting of the small cane surprised me, but just as swiftly as it came with each stroke, it quickly faded into a sense of numbness. The pain in my ass kept growing as he hit me, harder and harder each time, each stroke hurting a bit more than the last (I was not used to much pain). I wasn't sure why I was enduring this, as I don't usually like much discomfort, but I let him hit me again and again even though I was in extreme pain. My cock wasn't hard but I still felt horny and wanted to appease the man behind the cane. Once he had finished with the cane, my ass was stinging like it never had before, and he muttered "Good boy," and gave my ass another quick slap with the cane. It was the first time I had heard him say "Good boy," in person and it was the sexiest thing I think I had ever heard in my life. I took great satisfaction in the fact that I had pleased him, and it only made me want more, and more I got.

Next came the nipple clamps that I was pretty afraid of to be honest. He slowly clamped them onto each of my tender nipples and at first they hurt really badly, I thought they would be ripped off. Slowly I began to get used to the feel of the squeezing and they began to feel more pleasurable than painful. They made me aware of how sensitive my nipples were and each movement or slight tug on the clamps heightened the sensation I was feeling. After applying the nipple clamps he began to work on the rest of my body again.

I felt a cold brush of leather on my shoulders and upper back, it felt like a small tangle of leather straps, which I would later learn, is called a "flogger". He began slowly with the flogger just like he had with the cane, getting me used to the feeling of it hitting my back and ass. He wasn't hitting very hard with this flogger like I had expected him to, but he started to hit in very sensitive spots. The first time he swung it up under my balls sent a shockwave through my body that caused me to jump in surprise. It was a pleasant surprise, however, as my balls were not used to being touched by anyone or anything at all besides myself. Each stroke aimed at my balls slowly but surely got a little harder, and I jumped a little higher each time. In between hitting my balls he used the flogger on my chest and nipples, which spread the sensation over the whole front of my body. He suddenly stopped hitting me with that flogger and went to get another "tool". When he next resumed hitting me I felt it was with a larger flogger with thicker straps of leather.

He didn't work my front or my balls with this flogger though, he went straight to my back and ass, which was fine with me because my ass wanted some more attention after that caning. As he began to hit harder and harder, I found that the strikes on my upper back didn't sting like the lower strokes. There was no pain on my upper back, as it was more of just the sensation in knowing I was being "abused" by a big, strong man. When he took swipes at my ass and my lower back, it was a different story entirely. There was a sting associated with each stroke that reminded me that I was indeed being abused and punished. This flogger though, was more stimulation than pain to me and I enjoyed every moment and every strike he brought down upon me.

He then changed floggers a second time, and returned with the biggest of the three with huge, thick straps of leather. When he hit me with this it felt more like I was being bludgeoned than whipped, and it was hot as hell! I enjoyed this flogger the most as I could really feel the strength of the man behind me being transferred onto my back. He was letting me know who was the boss. Again as each stroke became harder and harder than the last, my cock began to get harder along with them. I never thought that being hit from behind with a leather flogger would be able to turn me on so easily.

Eventually, the flogging ended, and I was given a couple hard hits on my ass with a leather strap of some sort. He asked me what he was using, and I don't know if it was just the excitement of the situation or the surprising pain in my ass but for the life of me I had no idea. He just kept hitting my ass harder until I answered correctly and said "A belt". He seemed pleased with the fact that it took me awhile to figure it out and gave me one last slap on my ass with the belt before I felt him move away.

I was relieved when a moment later he began to unhook my wrist cuffs from the cross and removed the spreader bar from between my feet. My hands were so cold and numb from the lack of blood flow, and my shoulders were pretty sore as well from just being stretched more than they're used to. Just as I was relaxing again, in the absence of any new pain, when suddenly my nipples felt like they were on fire as he removed the clamps he had placed on them before. They actually hurt more coming off than they did when he put them on!

The next part of the basement I got to explore was the wooden horse situated away from the chains. He had my lay down on the top of the horse with my back to the leather and my head hanging back over the opposite end. It was at this point I knew what was coming next. He positioned himself in front of my upside-down face and placed his balls right on top of my mouth and nose! I was instantly in heaven, the scent of those manly balls and the their weight on my face. My tongue began exploring his musky sack and licking up all the wonderful manly tastes it could find. Then he removed his balls from my face, and positioned the head of his cock in my mouth. I knew I was in store for a throat fucking but I didn't care how he fucked me as long as his cock was in my mouth.

The first time he pushed it far into my throat I was unprepared and gagged almost instantly. I couldn't believe how big his cock was! He withdrew and slowly pushed back in, but not all the way. He was easing me into this process much to my pleasure. Within a few minutes I was able to take most of his hard cock into my throat and his balls began to nudge my nose when he was all the way in. I was in ecstasy! But alas, all good things must come to an end, at least for now. He withdrew his cock for the final time and began to get me into the next position of the night.

He put the spreader bar that was used on me earlier under my knees and pulled them up to my chest, exposing my ass and as a result, getting my cock rock hard. He then guided my arms under the bar and pulled my hands up to my neck. He secured my wrist bindings to my collar, which left me in a sort of curled up position, with my ass at one end of the horse, and my head at the other. Anything that was uncomfortable with that position was instantly removed as he gave me a pillow to rest my head and neck on.

I was so excited because my ass was so vulnerable and I had an idea of what he was going to do next. When I felt his finger touch my asshole with that cold lubrication, everything I had dreamed about for years was changing from fantasy to reality. He slowly inserted his finger into my ass and began to wiggle it around, opening up my virgin ass. When he thought I was ready, he inserted a second finger and widened up my hole even more, adding more lube to ease the process. Then came the feeling that I will not forget for the rest of my life. He rested his cockhead on the surface of my ass hole and began to slowly, but firmly, press it into me.

When he first made it past the tight boundary of my ass, it was a feeling like no other I had ever experienced before. There was a pain that continued to throb as he pushed further and further into my ass, filling me up like I had dreamed of. I didn't even know when he was all the way in, as it seemed like his cock went on forever. When he was fully into my ass, he waited for a second, and then began to slowly pull out and push back in with his hips, widening my hole. It still hurt quite a bit, but within minutes of his slow, steady, easy fucking the pain was replaced with intense pleasure.

It was when I got comfortable that he picked up his pace and began to fuck my virgin hole harder. He was able to get his entire cock into my ass as every time he thrust I could feel his balls hit me. The feeling of this man inside my ass, loosening my hole and taking me, all the while I was restrained, was intense. I began to groan in my newfound pleasure, wanting more of his cock, and wanting him to fill my up with his cum.

I think he thought I was enjoying it too much because suddenly he just stopped and took his cock out of my now loose ass. I didn't want him to stop, I wanted his cock to keep ramming my ass until he came, but that was not my decision to make. He next unhooked my hands from my collar, and removed the spreader bar from under my legs. My muscles were stiff as I stretched out and stood up, as they had been compressed for longer than I was used to. When I finally did stand up, he pulled me close to him in a hug and whispered "Good boy" to me. The feeling I experienced at that moment cannot be described by words. I was tired, sore and cold, but at the same time I was in heaven, elated to the fact that I had pleased this man who affectionately called me "His boy".

The session in the basement was done as he turned me around towards where I thought the stairs were and removed my blindfold. Following behind me with his hands on my back, supporting and leading me up the stairs, telling me we were going to the bedroom. There was nothing more I wanted at this moment, then to slide into bed with him and feel his warmth on my body.