When betting between male friends goes too far (part 7)

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[Part 6](

He pushed me up against the edge of the table and then pushed my upper body down over it and held me there.

“This will be the last thing we do tonight before I free you, but I have thoroughly enjoyed every second of using you. I just can’t wait any longer,” he said caressing my ass once again with his other hand.

“W-wait? F-For what? Wh-what are you going to do?” I asked, my voice trembling because I already knew the answer. I had tried to block the possibility of this happening from my mind because it was unthinkable and terrifying. I started to tremble.

He chuckled, “My dear boy, I am going to fuck you long and hard and love every second of it until I cum deep inside of you, claiming you as mine before sending you home to your wife…” And then I could feel the tip of his large cock slipping into the crack of my ass…

“N-no…please….n-no….I c-can’t….I’m not….please….” I begged, my voice breaking as I felt the tip of his large cock rubbing against my hole. I heard the plastic cap of the lube again as he then applied it to his own cock. My ass was still well lubed, he had planned for this of course.

“Oh, this is going to happen. Your fearful begging only makes me want to slam into you more. Just accept that it is going to happen, but you are welcome to beg if you like. As I said, it turns me on. But I already have consent for this and you know what? I think you secretly want it. Deep down inside you need this. I know you do. You’ve always needed this to happen, you just didn’t know what it was. This will make you feel complete….” he said softly, now rubbing the tip of his well-lubed cock against my hole.

“Now, I won’t promise it won’t hurt. It will. But you won’t be injured from it, the lube makes sure of that. But it will hurt your first time. It usually does for virgins. All I can tell you is to try to relax sooner rather than later and it will go better for you. If you fight it, it will hurt more. Just to add to your delectable fear, a part of me really hopes you struggle and force me to take you harder. Not out of cruelty you understand, just because I find it so hot….Anyway, I am going to give you what we both need and your job is to just accept it and take it. I have good control over myself, so it will end when I decide it does and I am ready to fill you with my seed,” he said, and the words he used made it seem like he was being cruel, but his hand lightly caressed me the whole time and his tone was soft and caring sounding. The contrast between what he said and how he said it kept me so confused.

I was of course terrified and so very trapped. Every fiber of my being didn’t want this to happen and wanted to beg or fight to get free, but I also knew that both of those things would further arouse him, perhaps making it even worse on me.

I suddenly started to feel pressure against my tight hole and immediate discomfort. “No….please….” I croaked, but suddenly the bulbous head of his cock popped inside of me. I cried out in despair and he let out a groan of pleasure. “Oh fuck, you are so tight. God damn this is going to be good. I am going to slowly push inside of you now. It will hurt less if you try to relax…” he said matter-of-factly as if it would be that easy. What was clear was it didn’t matter much to him if I relaxed or not.

I was panting with the discomfort I already felt and the terror over the additional forthcoming pain when I felt him slowly pushing in deeper. Very slowly like he was savoring it. Every inch increased my pain and I cried out, “No! Please stop! it hurts so much! I can’t….” but he ignored me and kept the slow pressure on. Inch by inch he slid deep inside of me and every whimper, cry, or groan of pain I made was followed by a moan of pleasure from him. “Oh fuck you feel so damn good. You are doing so well. I am almost there,” he said, somehow trying to sound encouraging.

The pain and violation were intense. I had never felt the like before. Oh, I had wondered his finger earlier had been painful and uncomfortable, but it was a drop in the water compared to his large cock. I was having trouble getting enough air to even cry out. It was an all consuming feeling as I felt his hips finally come in contact with my ass. He held there, his 8 inches completely buried inside of me and possessing me. I continued to beg him to take it out and to stop and he continued to ignore me.

“I’m not a mean man. I am going to hold here for a minute and let you get used to the sensation. It also lets me just appreciate taking a virgin ass. Damn, it is even better than I thought it would be,” he said and reached under and grabbed my testicles, giving them a light squeeze as they hung vulnerable below me. I cried out at the sudden additional stimulus and the mild pain from him squeezing. As he squeezed them he whispered, “Tonight, you and your body have become owned by me. You may not realize it yet, but you will come to crave my ownership. You will come to crave the pain if you know it makes me happy to hear you whimper…” he squeezed a little harder and I did let out a loud whimper on queue. But my cock, which was still embarrassingly hard, throbbed with the pain. I felt so exposed, helpless, and vulnerable to anything he wanted to do with me. All the while, his cock held there, filling me with pain. It did get a little easier as time went on, but it was so foreign to me. My body kept trying to push him out, which really only served to make me feel tighter to him.

He hands moved down and he took hold of my hips as he started to slowly slide out. I groaned with discomfort and the absurd hope he would change his mind and pull out entirely. Most of the length came out and he paused with just the head inside, but then slammed it fully into me. I screamed. Though much of my pain was really psychological rather than physical. This was the ultimate act to emasculate another man and my mind was all torn up from it. He pulled back again and then thrust in again, moaning at every sound I made.

His hands gripped my hips harder and he picked up the pace, thrusting in and out of me with long slow strokes without pausing. He started to praise me again, telling me how good it felt and what a good boy I was. I felt violated, and not just in my body. Every thrust inside of me pierced my mind too. I was helpless against this. Helpless as another man fucked me. It would only stop when he wanted it too.

He kept up that slower pace for quite awhile, praising me the whole time. I felt my mind break a little bit. Not detached, but finally come to really accept that this was happening and I couldn’t stop it. I surrendered to it, surrendered to him. He moaned and must have felt something as he said, “there we go…such a good boy….now you can fully enjoy it. Your ass is mine now.”

With that he picked up the pace, fucking me hard now. Not violently, but what most would consider a good pounding. My chest rubbed against the wood of the ping pong table and I started to feel like just an object to be used. I was humiliated but could also feel my hard cock swinging back and forth with his thrusts, and leaking below me. His pace was relentless. I had quieted some with my surrender and some of my sounds might have even sounded like moans of pleasure now.

I don’t know how long it went on. It could have been 15 minutes or an hour. He seemed inexhaustible, but every minute made me surrender to my fate even more. I felt owned. Completely and thoroughly. His moans of pleasure started to arouse me. I started to crave hearing them and started to moan myself, despite trying to suppress it.

That apparently pleased him exponentially. “Fuck yes!” he cried and slammed into me harder and harder. I knew he was building to orgasm now, and that he was gonna cum deep inside of me and complete his ownership. My body went completely limp with acceptance and surrender.

He thrust into me one final time, the hardest yet, crying out in victory and ecstasy, and buried deep inside of me, I felt his cock pulsing as he came. I cried out with the overwhelming feelings, both physical and emotional, and suddenly felt my own cock pulsing as I came too. Shooting my seed onto the floor. My entire body shook with the orgasm and I cried with it, both for how humiliating it was and how intense it was. It was the largest orgasm I had every experienced and so intense that it was almost painful. If I hadn’t been tied up and held down, I would have been writhing trying to escape it. The fact that I couldn’t do so only made me cum harder.

“Such a good boy. You are my good boy now…” he said softly, almost tenderly as his orgasm subsided and I was still trembling with mine…

(I hope you enjoyed! Sorry for the length if it was too long for you. I am gonna stop this one here, but I will write one more non-sexual part on this story to sort of put a ribbon on it. It will make it feel more complete and could serve as an ending, but it can also serve as a natural pause point. I will move onto another story after that post, but I will leave this story in a position where it could be resumed at a later time. I hope to post it fairly quickly, perhaps later today. Once again, thank you so much for your support into my first foray into solo erotic writing!)

NSFW: yes

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