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Submissive: Chapter 2- The Milk Man

I pulled and pulled on my bonds as he continued to pump my cock. I had just had one of the biggest, best orgasms of my life at the hands of the hottest man I had ever seen, and I was utterly terrified. He said he was going to punish me. I didn't know what that meant, but he said that I was going to be here for days. Plural. I was screaming into my gag, pleading with mumbles to let me go. James just laughed.

"You wanted to be punished. You chose this path," he said in his incredibly sexy, almost too hot for my own good Irish accent. Although I had my blindfold on, I heard him moving around the room, which was nice, because my cock was getting a much needed break, but which was also putting me on edge because I had no idea what was in store for me. Luckily for me, James seemed to like to explain things in full detail before he would actually do them.

"Now Gordon, I know that you didn't ask for any of this, but be honest with me. Was that not one of the best experiences you ever had?" I didn't have to think too hard about that one. It truly was. The loss of control and the waiting to cum was both frustrating and incredibly sexy to me, and I wanted more, but I just slowly nodded to his question. "And I bet you want to cum again, don't you?" Again, I just slowly nodded, although if I was going to go through what I just went through again, I needed a little bit of a break. "Good. And I am going to make you cum again. First, take this." He took the gag out of my mouth and gave me some very cold water. It tasted amazing. "Now I am going to unbind your hands. If you fight me, I will break a very important appendage that still seems to want some attention." I was in no mood to fight him, although I was curious as to what exactly was happening. He undid my bonds and sat me up. He was quite tender in his touches, gently caressing my body upright.

"Don't be alarmed, this is only a banana." It hit my lips and I got his joke. If he hadn't told me, I would have thought I was sucking cock for the first time. I ate it in no time at all. He gave me another, saying I needed my strength for the upcoming festivities. "How long am I going to be here, James?" I said it with as much sweetness and vulnerability as I could muster. He pushed me gently back down on the bed and began to strap me back in. "Well, I can sense you're scared, so let me put you at ease. I will not harm you in any way that will be permanent. I will push your limits though. Even when you say stop, I won't, because I can tell if someone can push themselves even further." He finished binding me, and got off the bed.

"I am going to make you cum, Gordon. A lot. For a whole day, I am going to make you cum and cum and cum. I want to see how far I can push you until you can't take any more. And then I am going to keep going. The record amount of times I have made someone cum in one day is at 18, but with you, I want to blow past that. Far past that. Get fucking comfortable, because you aren't leaving here until you cum at least 25 times. I am going to use my hands, my mouth, and a milking machine in order to do it. I am going to abuse your tits, slap your balls, and probe your ass, and get more cum out of you than you ever thought you had. And once you start dry shooting, well that's when the real fun for me begins."

At this point, I was actually freaking out. If I were to cum 25 times, that would mean once an hour, but it seemed like he was going to go full force, meaning once a fucking minute. I was screaming, begging, but he wasn't hearing any of it. "Again, you chose punishment. And this is your punishment. Well, part of it, anyway, but part two is tomorrow, and I'll explain that to you after you're done here." He took my still rock hard cock in his hands. "Seems like little Gordon is ready to roll. Oh and don't worry about getting soft on me. I put Viagra in the water you drank, and I'll do that all night and day so either you could dehydrate and pass out, or you could lay back and try to enjoy this."

With that, he began. "I am going to use some lube on the first one and then my mouth on the second. Then I am going to try and get some sleep and put the milker on you for a while. How does that sound, slut?" he said with a laugh. I was still shaking, pulling at the ropes. He lubed up his hand and started to jerk my cock. It wasn't the slow torture he put me through before, because now he really did want me to cum. And almost in no time at all, I had that feeling, and was cumming all over the place. There wasn't as much cum as the previous orgasm, but it was still an incredible amount. "Holy shit, dude, you cum more than any other person I have ever seen." The weird thing about this cum, though, is that I didn't feel it hit my body. It was like it went straight up in the air and then disappeared. It wasn't something I lingered on, though, because the assault on my sensitive cock took over all of my thoughts, as he took my cock into his mouth and continued to suck hard. I was going ballistic. I had cum twice in a matter of 30 minutes, and my body was in one long involuntarily spasm. How the hell was I going to get another 24 loads out of me without me actually dying?

My next load took a little while longer, and my body was going bananas at the time, but he finally brought me to another orgasm. He pulled off my cock right before I was about to shoot, and I shot as much as the previous time, but again, I didn't feel the cum hit my body. I think he was eating each and every one of my loads! This was one twisted kid. He finally pulled off my cock after what seemed like ages and walked over to his closet. "So, I am pretty tired, so I am going to try to get some sleep. It's about 4:00am now and I want to be well rested for later. Don't worry, I will be sleeping on my couch right over there so I won't be too far away in case something were to happen. For now, I am going to hook you up to my milker. It is a devious little machine. It has a mind of its own, meaning no matter how much you beg, it won't stop. You're poor little dick is going to be quite sore after this guy starts sucking on you." I felt a sleeve get put over my still rock hard and very sensitive cock. I shuddered at the touch. "We also have something for your balls too. I am not really into ball busting myself, but a small tap on this can be extremely pleasurable. You'll see what I mean by that soon. Also, I have a dildo to fuck you." Now, up until this point, although I was terrified by what was happening to me, I have pretty much enjoyed every single bit of it. I have never been fucked before, and I didn't know if I would be able to take anything up my ass.

"This is a very special machine to me. The dildo was designed by a very close friend of mine. It is hooked to a machine that will fuck you slowly for a while then fuck your brains out for a while. When it is fucking you slowly, the dildo will start to grow in length and expand in width. Right now, it is about 6" long and 2" around, which is really nothing at all. It will, however, grow to the size of my dick by the time the program is done, so about 10" long and 5" around." GULP. I feel the dildo be pushed into my ass. There was a considerable about of lube on it which was nice, but still, all the lube in the world would make me feel better about take the monster that I saw hanging between his legs. The dildo that he inserted hurt going in, but once it popped trough my hole, it actually didn't feel all that bad. In fact, it felt pretty wonderful. It was as small it was going to be, though, so I didn't get too excited.

He took the gag out of my mouth and put the bottle of water next to my mouth. I thought about not taking it, but I knew that he would keep this assault up no matter what I did, so I decided I would stay hydrated, even if it meant taking down some Viagra in the process. I sipped the water as he asked, "Do you want to say something, Gordon? This is your last chance for a while." I didn't even bother asking him to stop, or asking how long, or anything like that. I actually decided to try to compliment him, thinking that would put an end to this sooner rather than later. I said, "Although this is truly painful, I have to say you are the sexiest fucker with the biggest cock I have ever seen." He laughed at that and said, "Well, thank you, that means a lot to me. I don't have the biggest dick in the world though. I have a few friends that have bigger dicks than I do. One of them, the one that designed my fucking machine actually, and also a fellow brother, has a 13" dick, which I said was actually impossible, but we measured it, and he was telling the truth. He had a 10" dick but said he wanted it bigger, so he came up with a growth pill. It worked like a champ." I am going to make it a point to try and avoid him. "And then I have friends back home, twins that have about the same size dick as me but they are even more fucked up and twisted than I am. They put both of their dicks up some of their...slaves." The word slave was said to frighten me, I could tell, and it worked. Was that what I was? And if it was, why did I love it so much? "And the stamina they have. Well let me just say that they recorded one of their sessions. They fucked this hot piece of ass for 3 hours long and hard, and they still didn't cum once, even though the slave had cum probably 15 times. I'll have to have them come down and hang with you for a night or two." I shook my head as he laughed.

"And the finishing touch..." I felt a clamp go on my right tit followed by my left. It hurt like hell because I have extremely sensitive nipples. He loved my discomfort, adding "I don't want you to feel too much pleasure." He moved to the foot of the bed. "Are you ready, sexy?" I just lay there and tried to wrap my brain around what was going to happen. He flicked a switched and the milker kicked on. It wasn't too fast, but my cock was extremely sensitive, so it was like a lightning bolt struck my dick and sent waves through my whole body. I noticed a little tapping at my balls. It wasn't nearly hard enough to hurt, and actually felt quite good. The dildo began vibrating and moving slowly in and out of me. So far, besides the slightly painful feeling on my sensitive cock, everything was feeling marvelous. "I am going to go sleep now. I am a pretty heavy sleeper, so you can scream as much as you want. Might put me to sleep even faster." I could barely hear him walk away as I was moaning into my gag and the hum of the machines made it difficult to hear.

It took a little while because the milker wasn't going all that fast, but the first load was forced out of me with great force. It was a huge load, and I was still amazed that I could cum so much after what I had been through. However, that is when the real torture began. The milker didn't stop. In fact, it sped up slightly. The tapping on my balls got a little more noticeable, and the dildo began to expand in my ass. All of these things happened simultaneously immediately after I came. The sensations were just too much, and I went crazy in my bonds. I couldn't take much more of this, but I knew that I was going to be here for a very long while. I was honestly fairly content with that fact. I was going to be put through some serious torture, and that excited me. The fact that it excited me was quite puzzling, but I didn't linger on the subject too much because my private parts were being assaulted.

The second load took a lot of work. The milker was going full force, each new suction bringing an incredibly wonderful yet unbelievably terrible sensation to my entire body. The tapping on my balls, something that I would not have thought I would like, turned me on greatly. It wasn't hurting so much as churning my cum filled balls. The dildo was much bigger than when we started. When it first expanded, it hurt. It really fucking hurt. But once I started getting used to it, the pain became incredible pleasure. I thought my balls were running on empties, and by the time I came again, I was shocked at how much cum I felt leave me. As soon as I began to cum, the pounding on my balls went to full force, the milker kicked it into high gear, and the dildo started pistoning in and out of me. It was unreal the assault I was taking from these pleasure/torture devices.

Once my orgasm subsided, which took longer than usual, the machines slowed down. They were still going faster than the previous round of torture, but again, the milker was a little faster, my balls were being tapped a little harder, and the dildo in my ass expanded again. And this is how it went for the next 8 orgasms. I don't think I was producing cum by the last of them, and my dick, balls, and ass were beginning to get quite sore.

"How are you feeling?" That sexy Irish voice would have startled me if I hadn't been so drained of energy. I think he could tell that I was literally spent, and he said, "Give me one more orgasm and you'll be done for a while." There was a real sincerity in his voice. While I didn't think that he was going to stop after this orgasm, his voice gave me hope that this may all be over. "The dildo is at its biggest size, the milker will be at its fastest, and your balls are going to get hit the hardest. You should cum in no time." He couldn't have been more wrong. Yes, all of the devices were going at a crazy speed and strength, and my cock was rock hard, but this was pure torture. James kept encouraging me, though, whispering things in my ear, trying to get me to the finish line. The dildo was going at a pace that probably tore my hole wide open, my balls felt like they were being kicked hard every other second, and the milker was going so fast on my sensitive cock that I'm sure it was a blur to the human eye.

My body began to tense up and I knew that I was going to cum. Just as I was about to shoot, James took the clamps off my sensitive tits, causing me to scream louder than I ever thought I could, as I came. This orgasm was unlike anything else I had ever felt before. While each orgasm I experienced that night was mind blowing, this one actually shut my body down. I couldn't move as the milker, ball buster, and fucking machine wailed on me for the last few seconds. The pleasure and pain I felt cannot be described. I have felt that same feeling many times after that, but this was the first time I knew exactly what pleasure felt like. Once I began to breathe again, I realized the machines were removed. I was so happy, but I knew that this ordeal was far from over. I couldn't take anything else. I began to cry. I never cry, but I sobbed like a child when the thought of having to cum again entered my mind.

James was already removing my bindings when I began crying, and as soon as I was free, he cuddled up right next to me and gave me sweet little kisses all over my body. "You did so good, baby. You are done for the day. I knew you could do it. Strapped to those machines for 6 hours. I knew you were special." His comforting words, as well as the knowledge that I was done for the day, calmed me down a great deal. "Gordon, I am not going to apologize for what was done to you, because I think you loved every second. I needed to test you to see if you were who I thought you were. And you passed with flying colors. The brothers are going to be so happy. You are only one of six who passed this semester out many interested. I am so happy and proud of you." I had no idea what he was talking about, so I mustered every ounce of energy and said, "Huh?"

"I have been watching you for some time, Gordon. I knew you were gay, and I thought you were... submissive. But from what I can tell after last night and this morning, you love being helpless, at the will of another man." He was 100% correct with that assessment. "Our Fraternity is a bit different than others. Almost all of us are bi or gay, and we are the most prestigious, best frat you can join on campus. We are extremely selective in our choices of brothers, and we test each person being considered for membership before we even begin the pledging process." I must have still looked slightly confused, along with totally spent. "Each of our pledges are slaves." That hit my like a ton of bricks.

"What?" I ask, not really believing what I am hearing.

"Although we are all Brothers, and love and respect each other, the pledges are put through tests that render you helpless, like you were tonight. You also do anything a Brother is to ask of you. While slave seems kind of harsh, it is the best word to describe it." I must have had a look of horror on my face now, and he tried to comfort me. "Gordon, all of the tests are meant for you to grow, to feel pleasure. Mostly everything what happens to you during the process is for your own pleasure. If you mess up or something, that is where the pain comes in."

"Why are you telling me all of this?" I asked after a long pause.

"Because you are going to be asked to pledge this frat, and you need to know what you are getting into beforehand, because once you are in, you are in. There is no turning back without great consequences. You do not have to give an answer now, and in fact, I would wait at least a week so you can process everything that is going on. And plus, you still have more punishment for me to give you." I could feel a lump in my throat forming. I couldn't do anything else for him. He again consoled me. He seemed to pick up on my signals quickly. "Not now, Gordon, but later. I didn't really think I could pull 25 loads out of you for the whole day. The most I even got was 10 in 12 hours and you already beat that, so you have already proven yourself. Now, you sleep. Rest so tonight you will be ready to meet the rest of the fraternity." Those words made me both excited and nervous. I couldn't even imagine what was in store for me, but that was on the backburner as the real question lingered in the air: Did I want to be part of this frat? The past few hours had been maddening, and I totally loved every single second of it. This may be a world that I want to be a part of. The punishment aspect was something I was not really keen on exploring, but the pleasure side was highly alluring. James was right. I would have to think about this. This was a lot of information to process, and I had barely any energy left in me. I immediately fell asleep after I closed my eyes, dreaming of what might be coming my way in the future.

Up Next: Submissive: Chapter 3 - THE SLING



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