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My first man - full story

Years ago i had a classmate whose parents used to work with mine, so they would often meet for dinner, either at my house or theirs.
He was my age and he had a brother, much older than us, whom eventually started to spent time with us when our families got together.

At that time me and my classmate were regularly jerking off together (not mutually) and measuring our dicks, but we never touched each other and i had never felt any urge to do so. His brother never took part in any of this, but sometimes we would openly speak with him about our sizes and the girls we got off to.

One day we were playing videogames when my classmate's mother went mad with him about some homework he didn't do, and told him to stop playing until he was done with it. So he left the room while me and his brother kept on playing.
It was late spring and we both had shorts on, the kind of shorts you would use for sport, no zips or buttons, just a rubber cord. All of a sudden, he turned the videogame off and told me if i was up for something more interesting, and before i could answer he played a vintage porno movie that i had watched several time with my classmate.

This movie had several mini episodes, and he asked me wich one was my favorite while pulling his shorts down, revealing a very stiff package under his boxers. He began touching himself while looking and the screen, his underwear still on. I was looking between his legs wondering how big he could be...he looked bigger than his brother, who was almost twice my size already.
Since i didn't answer him yet, he turned towards me and asked me again. At that moment I realized he caught me looking at him because i raised my eyes only when he talked, and i felt somewhat ashamed by the smile he gave me, but made no big deal of it and answered ''the second'' without even knowing which one it was

Right after playing the video he leaned back on the sofa and took his cock out...i couldn't believe how big he was, he was already hard and his head was completely out of the foreskin, it was the first time i saw a cock like the ones i used too see in porno movies, so i asked him how big it was.

Before that day we had already spoke about my size and his brother's, so he knew i was only 3 inches. As i asked the question he stood up and reached for a ruler, moved right in front of me and got the ruler next to his cock.
Then, instead of simply telling me the result he got even closer to my face and told me to read it myself, and i leaned forward so that i could look it from above...he wasn't more than two inches away from my face when i read the ruler and said ''wow, almost 8!''...he laughed and begun masturbating again, moving just a little bit to the right so i could see the screen, his dick stil very close to me.
I tried to look away and focus on the screen, but my eyes were still bouncing between him and the video, even though i still didn't feel any real attraction, just curiosity...

Shortly after he sat down and told me that i had to take mine out if i wanted to keep on looking the video. I felt petrified hearing that, not just because we never got naked together but mostly because of my size, even though he already knew how small i was from our previous conversations.
So i tried to decline several times but he kept insisting, until eventually he put his pants back on and said that we would then have to stop.

In that moment i realized i didn't want to stop, and i knew i couldn't care less about watching the video or jerking off, so i had to admit to myself that i just wanted him to take it out and jerk it so that i could watch how much of his dick was left out of his hand when he grabbed it, how wide his jerking movement was compared to mine, how his foreskin would never cover his tip completely...and so on.
I tried (very briefly) to convince him to go on without having me undress, but of course he wouldn't, instead he stood up and went for the tv as to turn it off.
I had to choose between humiliating myself in front of him or losing the chance to enjoy all of those new sensations. Obviously, i took off my shorts and underwear, spread my legs a bit and looked up to him (i had been sitting down all the time). As i was waiting for his reaction i remember feeling no shame at all, despite of my expectations.
Now, i felt VERY uncomfortable while i was undressing, anticipating the shame i would feel and repeating to myself it was the only way to get him naked again...one more time, i was up for a surprise as i felt completely at ease once i was done, to the point of spreading my legs to show it properly, even though it was totally soft. I felt good for being so obedient, and excited at the thought of him being now ''obligated'' to take it out again. It was similar to the kind of satisfaction of getting a good grade for behaving right and doing what the teacher wanted.

As i sat there looking him from below he smiled but didn't say anything, instead he went for the desk and took the ruler back. I was expecting to get my ''reward'' right away instead, so i had a moment of disappointment and was just about to tell him when he pointed the ruler at me and told me to get it hard so we could measure it. That phrase was enough for me to stop thinking about my disappointment and start masturbating as he ordered...suddenly, him having his boxers on didn't make any difference anymore. In just a moment i had committed to fulfill his requests regardless of my reward. And again it felt good, really good, because it wasn't a ''circle jerk'' anymore, i was not jerking off on a porno with a friend on my side. I was, for the first time, jerking off in front of a not-really-friend of mine just because he told me so, and i was doing it while hoping to watch him again...i was looking at me while doing it, but everything i saw reminded me of how badly i wanted to watch him again...my hand completely covering my dick, my foreskin just barely opened, the thought of how superior he was...with these things in mind i eventually got a little hard, not for a second i had thought about the video.

Just like before, i stopped and took my hand off to show him, feeling satisfied like a good student. He gave me the ruler, his boxers still on. I was barely 3 inches and when i showed him he got in front of me and finally took his dick out. Then he bent his knees and got his dick right next to mine, making funny remarks about how his head alone was almost bigger than my whole dick even when it wasn't hard like before...i kept my head down hoping our dicks would come in contact, even briefly. I didn't want him to get it away so i began to play along with him by making remarks about how much bigger and harder he was. I wasn't using my hands at all but i felt my dick getting stiffer for the excitement...i was now totally committed to my role, and i felt entitled to slide my dicklet below his own, while telling him how easy it was to make me disappear under his superior cock...i did that because i figured he would be pleased (and he was), but my actual goal was to make contact. It took me just a slight movement to get my dicklet touch him, just a little poke from below, just for an instant. It wasn't much and it didn't feel like anything special, but immediately after that he blatantly got down and gently slapped me with his semi hard cock. When he did that i felt completely dominated, i wasn't smiling anymore, my mouth was opened and my dicklet began to get smaller and smaller despite my growing excitement.

Now i was fully aware of the situation and realized that, after this, i'd have been obliged to fulfill any request he made me. I didn't even feel the need to ''play along'' with him anymore, it was clear to both that i had completely submitted to him. So i started to picture what i would do if asked to do ''other things'', but the only thing i could think of was me grabbing both of our cocks together to have him fully hard again. I would have probably tried that but he suddenly stood back instead, exposing my (now almost completely limp) dicklet.

I didn't know what to do or say, i felt like i wasted a good moment with my overthinking but my thoughts were interrupted when he began jerking with both hands in front of me, while asking me if i could do the same.
So i showed him how even one hand was way too much for me, and i comically tried to find a place for the other hand in an effort to amuse him. Meanwhile he sat down very close to me while i was stilll trying to play with both hands, he laughed along and then finally told me that, since i didn't need it, i should use my other hand on him, so that he could have one free. He said that laughing, like a joke, making it sound as if he didn't actually mean it.

I laughed along but without any hesitation reached for his cock and grabbed it fully with my left hand. I wasn't sure it was what he wanted but when i saw him taking his own hand off of his cock i took aside all the doubts and finally began to openly masturbate him...not just touching, actually jerking him off to a porn while simultaneously jerking myself to his cock. It was the first i had ever touched. I thought it would feel weird, embarassing or even disgusting...instead, the first thing i felt was satisfaction. Maybe because it was one of the most ''prohibited'' things that i could be doing at that time, but i will never forget the determination i had to touch him in the first place, i switched from ''i will never do it'' to ''i HAVE to try'' in a matter of minutes...i didn't try to explain that to myself for a long time.

I worked him until he got hard like before, it felt great...i loved feeling him growing and i loved him staying that hard. Then, as he started to breathe heavily i stopped touching myself and moved sideways towards him, then i moved my left hand to the base and grabbed the tip with my right, just like he was doing before, and he let go a long breath of pleasure that made me feel like a good boy again. I found myself smiling and i began going faster and listening to his breathing...i was determined to do exactly what he wanted, but he didn't say anything until he was about to finish. He suddenly told me to ''watch out! cover the point, hurry!'' and since we hadn't any tissue or anything, i shielded his tip with one hand and made him cum with the other.
He made a real mess and unfortunately i wasn't able to fully enjoy the moment right after he had just finished, because we had to clean the mess...i liked to be naked next to him with my hands full of his cum, and i found it appropriate for me to not have finished myself, just him...that night i played that moment in my head while masturbating on my own.
4 years ago
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5
agia 3 years ago
Wonderful story
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michigan1995
🔥🔥🔥
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SegaiolaSottomessa Publisher 3 years ago
to tunemaker : thanks! Glad you enjoyed that!
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tunemaker
tunemaker 3 years ago
Delicious ?
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SegaiolaSottomessa Publisher 3 years ago
grazie davvero!
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