Schoolfriend Humiliation Pt. 04

"Go slow, take your time, and enjoy it." He said comforting me.

So I waited a few seconds for the pain to subside and then slide further down his member. I could feel every vein on my way down his dick. Rubbing against my sensitive sphincter simulating me. I also could feel his dick pressing against my prostate, which was sending jolts of pleasure through my body. It did not take me long to get down to his bush, which was tingling my balls. When I got down I rested there a bit.

"You are a natural." Benjamin smiled at me.

It strangely felt like a compliment and I thanked him to which he smiled even more. Without him prompting me to do anything I started to bop up and down on his. Using it to fuck myself and give me pleasure. Benjamin just lay beneath me, moaning softly and looking me in the eyes. His gaze was comforting and reassuring, which made me even more confident.

I was now sliding up and down the whole length of his dick. My dick was also extremely hard, leaking precum onto his belly. All I could feel and think about was Benjamin's dick deep inside of me, pressing against my inner walls, pleasuring me in ways I never thought about. I closed my eyes and enjoyed that feeling.

I rode him like that for a few minutes when I felt my legs giving up and getting shaky. Benjamin must have noticed as well.

"Hey lay down on your back and let me do some work."

He reluctantly got up and let his dick slip out of my ass. As it flopped out it slapped against his belly. I could feel how open my hole felt and also it felt like something was missing. I wanted his dick back in my hole as fast as possible. So I Quickly lay down on the blanket pulling my legs up exposing my hole.

Benjamin laughed seeing that and got behind me.

"Someone is eager to get fucked I see." He said as he was slowly shoving his dick back into my hole. It felt incredibly good. In this position, it felt like his dick got even deeper into me. He leaned my legs against his shoulder and leaned forwards. His arms were placed next to my head.

"Close your eyes and enjoy the ride." He whispered to me softly.

"Yes." That was all I could muster as I closed my eyes. Benjamin was moving his hips slowly back and forth. This slow movement felt incredible. It felt like I had multiple orgasms without cumming with every movement he made. I could feel him leaning down even further, pushing my ass up in the process. Then again he surprised me by doing something I was not expecting. I could feel his lips pressing against mine. My eyes shot open. He was kissing me on the lips. Feeling safe with him now, the way he had treated me today, I slowly responded to the kiss. We kissed for what felt like forever, all the while he was still slowly fucking my ass.

"You like that?" Benjamin asked, pulling his face away a little looking me into my eyes.

"Yes, I love it."

"Perfect. Then let yourself go and enjoy it." And with that sentence, he kissed me again. I could feel my orgasm coming closer and closer. I did not even need to touch my dick. His dick was all I needed right now. All I needed was his big dick inside of me.

"Please, I'm getting close, fuck me harder," I said to him. I still sounded weird hearing myself saying that, but I meant it. I needed to get fucked hard now. It did not matter if it was gay to have my ass fucked by a man anymore, all I needed was the pleasure it gave me.

"Ok, then get ready." Benjamin slowly but surely got faster and harder. His dick was now ramming deep inside of me, his hips smacking against my butt. I had to close my eyes. I was overwhelmed by pleasure. Benjamin was plowing my ass, my whole body was shaking every time he rammed his dick into me. I could feel it. The tingling got more and more intense. I could feel my balls tighten my dick got even harder.

"I'm gonna cum, Benjamin, I'm gonna cum." I moaned.

"Then I'm gonna cum with you." Benjamin moaned. He again leaned forwards and started to kiss me. That kiss was too much for me and I came. My dick started to twitch and I shot my load all over my stomach. My hole was clenching around his dick which brought him over the edge as well. He started to moan into my mouth and with one big push, pushed his dick as deep as possible into me keeping it there. His dick began to twitch and I could feel his cum shooting deep inside of me. It felt like it was even more than last time.

He kept kissing me even after he came and his dick slowly got soft inside of me. After a little while, he pulled his dick out of my ass and sat down. His cum came flooding out of my hole, which I was unable to squeeze shut.

"Did you enjoy that?" Benjamin asked me in a calm voice.

"Yes," I answered now more clear in the head. I was still nervous because I did not know what his intention was.

"Perfect, then listen to me. I wanted to show you how good sex with a man feels when I first saw that video of yours, seeing you cum getting fucked. But then I thought maybe you also enjoy being humiliated, which you do. So I decided to do the things I did to help you understand that. I'm sorry for doing that, but I felt I needed to do that."

Hearing that explanation was kind of weird. The reasoning was a bit confusing to me and did not make a lot of sense, yet still, it made me happy to hear him apologize and try to explain it to me. He was right in hindside all of that felt good. Now that I was thinking straight I concluded for myself.

"Benjamin, somehow I feel like saying thank you. I feel like you were right." As I said that I sat up and looked him into the eyes.

"Phew, I'm relieved you understand me." He quickly said, seemingly he had been nervous about my reaction.

"Also, Benjamin.?"

"Yes?"

"Could..... Could we maybe do that again?"

He looked at me dumbfounded for what felt like a minute. I felt really ashamed after that question and had to look down. He then laughed.

"Sure, seems like you enjoyed it. But now let's get cleaned up in the lake and enjoy the rest of the day."

In the end, everything was fine. I realized that I enjoyed being fucked and humiliated and also that I was gay. Benjamin, Jonas, Leon, and Tim kept fucking me regularly and we were all happy. Also a year later I got into a relationship with Tim, which did not stop me from getting fucked by many other men, but that's a different story.