When Master has it in his head that he wants to make me suffer, he makes sure that I feel it. He had played with my head (both my brain and my cock) for hours now, and I knew that it was far from over. He had said to prepare for a full weekend of tests, but I never thought he literally meant 72 straight hours.
I had just had one of the most mind blowing orgasms in my entire life, but I knew that I had cum without permission, and that I would be punished. I also knew that the amount of times it took for me to dry shoot would be the amount of months I would be locked in chastity. Master knew this would be a particularly horrible punishment because I cum a lot. I don't mean that I cum a lot SOMETIMES, I cum a lot EVERYTIME. It would take me many times before I would dry shoot.
"I'm sorry, sir. I'm so sorry," I whimper through the gag.
"Not yet, boy. But you will be sorry." He meant it. He had that tone in his voice that I both fell in love with and am terrified of. "So here is what we are going to do for the next few hours." He got up from the bed and walked to the closet. I already knew where this was going.
"I am going to edge you a little bit more until you are ready to go. Then I am going to put your favorite toy on you. I'll just sit back and relax and watch you... enjoy yourself." I could almost see the evil smirk through the sweaty blindfold. The milker Master had was rough. It felt incredible if used in moderation, but I had a feeling that moderation was off the plate tonight. The milker consisted of three tubes, one for my cock, and two for my balls. Although the suction on my balls was light, after the third cum, they would be very sore.
Master removed my gag and I began to beg him to release me, knowing full well it would fall on deaf ears. He gave me another drink of water. The water had two crushed Viagra tablets in it, but I wouldn't find this out until later. He then put another gag on me, one that I could breathe through. This was new. In our sessions I would either have a ball gag or no gag at all, since Master loved it when I screamed.
Master began to rub my sensitive cock. I lost my breath at first, as he began stroking it slowly but firmly. "How does that feel, boy?" I could only whimper as he began to polish the head of my dick. It sent shockwaves through my entire body and I couldn't help but scream through the gag, which only encouraged Master. "Mmmm, I love the way your cock makes your whole body go wild, boy."
He continued to play with/ torture my cock for another twenty minutes. At that time, he began to hook the milker up for my punishment. First were the balls, which were always tricky because not only did I have big balls to begin with, but with the chastity I was subjected to for two weeks as well as the edging, they must have been huge. It took a few tries for the suction to capture them tightly. It felt quite good, but I knew that feeling would subside soon. Next I felt him by my face. I thought he was going to remove the gag and listen to my scream all morning, but he left it in.
"Alright boy, I am going to leave this on you until you dry shoot. Remember, the amount of times it takes to reach that point will be the number of months you spend in chastity." As if he needed to remind me. I was dreading this whole ordeal, and yet my cock was rock hard. Side effects of the Viagra, but I didn't know that at the time. I thought I was just so fucked up that the thought of being punished and then being punished even more was exciting me.
When he placed the milker on my cock, I immediately screamed. "You have my permission to cum as many times as you want, boy," Master said with a laugh. I was going nuts. Before when I was being edged, I wanted to cum so bad, but did not have permission. Now, I want nothing else but not to cum, but I knew that I would cum over and over. Master loved testing me, and this seemed to be my most difficult test yet.
I was coming very close to cumming my first time, and knew that it was going to be a huge load. I was trying to hold off as long as I could to try and get as much cum as possible out of my balls, but the sensations of my cock and balls being mercilessly sucked was too much. I began to tense up and I was about to shoot. I knew this orgasm would be powerful, and it would probably hurt. I began to cum, and milker increased its speed, making sure to get every last drop of my huge load.
Just as soon as I had cum, I tasted something salty coming through my gag, and a lot of it. It was my cum! The gag had a tube running from my mouth to the tube around my dick. I was going to eat every load of cum that I would produce tonight. This was a new kind of sick and twisted that I have never experienced. The milker didn't stop after I came down from my orgasm and I was going insane. The sensation I was feeling on every inch of my body, but especially my cock, was like nothing I had ever felt before. "How do you taste, boy?" Oh, how much I hated my Master, but loved him so so much.
After the second and third time I cummed, I was totally spent, but I still was cumming like a hose. I couldn't believe I was still rock hard. I thought I was going to pass out soon; in fact, I prayed for it. Master has put nipple clamps on to stimulate my already over stimulated body. I was being tortured beyond what I thought I could ever take. I hated yet loved every second. I knew Master did this to test me, and I wanted to succeed for him.
However, after the sixth time I came, I was beginning to panic. That is six months in chastity. How in the world would I be able to survive that long without cumming. But the milker kept feeding me my own sperm. I didn't know how long I would last, but I knew I was reaching my breaking point. I think master knew as well, because he told me that once we reached the three hour mark he would stop the milker. I didn't know if that was in 2 minutes or two hours, but I hoped it would be soon.
I had now cum eight times and still a few drops of cum came out. I was cursing my dick for betraying me, but I was at the point where I was delirious and thought I was about to die. After my eight cum, I heard the milker speed up. "This is your last one boy. Make it count." My dick was so sore, but still rock hard. I was so happy Master was going to end this torment. As I was getting closer and closer, he began to play with my sensitive nipples. Master knew how to drive me wild, right to my breaking point. I tensed up and was beginning to cum my final time, and Master took of the nipple clamps. I screamed as I began to dry shoot. I immediately passed out...