Someone contacted me recently, wondering if I might be interested in assisting them with some extreme CBT; I was indeed. There was a pretty explicit description, with photographs, of what he was looking for on his profile. The profile made it quite clear that there would be no fucking involved; he admitted that he was married and that she wasn’t aware. Exchanging messages, he provided a bit more detail and I let him know that I would be willing to help him with his interests. He was a bit surprised, perhaps because he hadn’t expected to find someone so willing to do what he wanted to have done. There were writings that he had posted, some that had been written a few years prior. Reading them, I was enlightened a bit as to why he was surprised. He asked me what I thought of them, my answer to him was “You seem tortured inside.”
I’ll refer to him as T for Tortured here.
We chatted a bit more. He was interested in ideas that I may have for him. When I described some he liked how they sounded. He wondered what plans I had for him, and I told him that I would probably go from his instruction and include some ideas of my own. I was still working on formulating my plan. T said that he could bring the equipment shown in some of the photographs, which was helpful. We batted more ideas back and forth. We discussed his limits, which were pretty much what I had in mind: no permanent damage. Then, T asked if the thought of this excited me or was it more curiosity; I said a little of both. He then admitted that the process would most most like make him cum, perhaps a few times. He wondered if I would also want release, and did I expect him to be involved with that. I explained that if it were necessary, I did not expect his involvement. T admitted that he was hard merely having the discussion.
T was anxious to see his fantasies come to fruition; he wanted to get started the very next day. My schedule was a little too tight to allow that, so we agreed to meet the following day, Friday the 13th. It was best to meet for a face to face somewhere neutral first, I felt. First, to let T know that I was for real and not a faker, and also so I could see who I was dealing with; develop a comfort zone. A park near my home was convenient for both of us, so we met there at noon. I recognized him from his description right away. We chatted a bit, and since I was comfortable with the situation, I had him follow me home.
We wasted no time and headed straight to the bedroom. Earlier I had gathered a few implements form around the house and garage, they were laid out on the nightstand. T had brought a couple of boxes with his favorite tools as well, which he set on the bed. I spread out a towel on the bed and had several smaller ones nearby. T took off his pants, sat on the bed and removed his cock and balls from the opening in his jockeys. He asked me if I was going to remove my clothing, and I told him that I hadn’t planned on it. I was taking a very clinical approach to this.
I wanted to start by binding his cock and balls with rope, but I wasn’t confident with my abilities or the type of rope that I had. From one of his boxes T produced some zip ties that could be used, the type that can be loosened. Perfect. I worked to cinch them on; one for the ball sack and one at the base of his cock. His cock was erect. Now I wanted to insert something. He had brought the tool extension he had used in a photograph, I had a similar one that I had found in the garage. Ultimately we settled on something that he pulled from his box; a 6” crochet hook. I asked if he had a specific lube that he preferred, he said any would be fine. So I went to my nightstand to retrieve a bottle of lube, lubed up the crochet hook and inserted it into the tip of his cock. Gently, slowly I pushed it down into his urethra. It went in pretty smoothly, binding a little but with gentle coaxing it continued to about four inches. This is where it stopped, and even with much gently coaxing I wasn’t willing to push it any further. T suggested loosening the zip tie, which he did. I still couldn’t insert it any further. So T took over and used a bit more force to push it all the way in, with just the end of the hook protruding from the tip of his cock.
It was my intent to start out slow to get an idea of what he liked, and what kind of pain he could handle. I started out with some electrical alligator clips to pinch skin on the shaft of his cock. Six clips applied, so far so good; he was fine with that. Now I wanted to go with one of the ideas I had; straight pins through pinches of skin on the shaft. T was fine with the idea. I used alcohol swabs to sterilize the pins and to clean the skin. I pinched some skin on the front of his shaft, close to the bottom and ran the straight pin through the skin to the other side. T just lay there, no sound. I did this several more times until I had ten straight pins inserted through the skin of his cock. T said that this was the type of pain that would most likely make him cum.
I was ready to try something else, the portable vice that T had brought, do some crushing. The straight pins needed to be removed first though. Carefully and gently I removed each pin. I warned him that this might sting as I wiped the skin with an alcohol swab. There was a bit of blood on the cotton swab when I was done. The crochet hook stayed in place. I picked up the portable vice and opened it up enough to fit his cock in it. T stretched his cock out while I tightened the vice. I asked if he had done this with something inserted in his urethra before, he said this would be a first. I tightened the vice until T told be to stop. After a a brief pause he told me to continue. We went like this until the vice was closed to nearly half an inch. That was as much as T could take. He said the crochet hook inserted was probably keeping him from being able to go further. We left it there for a few minutes then removed it.
Next up T wanted the ‘cock stretcher’ that he had created with various hardware. The zip tie on his cock was removed for this. When the zip tie was removed, blood started leaking from the tip of his cock. I grabbed a towel for the blood. T removed the crochet hook, which was covered with blood and applied pressure for a while. T wasn’t ready to give in yet though. He took a band aid from his box and applied it to the tip to stop the bleeding, and suggested we continue. I fitted the stretcher over his cock. He explained that the head of his cock needed to be engorged to fit correctly in the upper loop of the stretcher. I stroked his cock in an attempt to accomplish this, but while it was in this stretcher I wasn’t able to get a good grip on it. T suggested that this is where having me unclothed would help, so I undressed. It helped. Soon enough the cock stretcher was properly fitted on his cock, and the stretching began. I turned out the bolts as much as I could by hand until they were too tight for me to turn any more. T took over at this point and stretched it some more. He had reached his limit for the stretch, so he left it there to savor for a while. After a few minutes we removed the stretcher. This caused more blood to seep from the band aid.
T suggested that using the straight pins would bring him to climax; he wanted me to put the pins in his shaft again. He brought out a couple of clips that would help keep the skin pinched to enable pushing the pins through easier. I went to work pushing straight pins through the pinched skin of his shaft. Many more went in this time than last time. He asked for a towel, he was getting close to climax. When I pinned the twentieth pin, he quietly came into the towel I had given him. When he was done I began removing the pins, wiping the skin with alcohol swabs. There was considerably more blood this time. Also, more blood was oozing from his tip. I got another band aid out of his box and applied it for him. I was very concerned for the condition of his urethra, he didn’t seem to be though.
So, T got dressed and collected his things. He thanked me, saying it was exactly what he had hoped for. I told him I’d be happy to help again, and he was on his way. A short while later he messaged me, thanking me again. But now he added that he was suffering huge guilt. Tortured.