First Time Jacking Off A Boy

I have been reading these hot stories on ST for a while now and thought it was finally time for me to contribute! 

I guess it's been a life long obsession so to speak. When I was young, I caught my older brother jacking off to one of my father's Playboy magazines. He was 16 or 17. I walked into the bathroom not knowing he was in there and saw him stroking his fully erect cock. Up till then, I had not seen a real live fully erect cock. He was embarrassed, and screamed at me for walking in on him. I said I was sorry, and turned around and left, but after I shut the door I put my ear up to it and listened. After about 3 or 4 more minutes I heard a shuffling noise, him breathing hard with a moan, and then heard the toilet flush. I didn't realize it then but about 15 min later I noticed my panties were wet. I was "turned on" but at that time I did not know what was happening. Not that I was a total prude either. I had stolen glances at my father's magazine collection a few times, and we lived in a house where none of us would totally cover up if we were walking around, or just coming out of the shower. I had seen my father numerous times in his briefs, but never saw him "hard". Also I had heard my parents "wrestling" from time to time but didn't pay much attention to it.

I decided that I wanted to hear my brother again, so I would pay attention to him when I would see him sneak off to the john, or to his room.

My brother's bedroom was downstairs, and adjoining to a closet. I found out that I could see into his room from the back side of the closet by scraping a small spot thru the boards. Good old knotty pine walls! His bed was up against the wall that I was behind, but a little off to the side. I would watch him come into his bedroom, and take off his pants and briefs, grab a magazine, and lay back on the bed. Sometimes he would be semi hard when he would pull down his briefs, and sometimes he was really limp. I was just fascinated by his cock, and how it would stiffen, and how he would manipulate it. I watched him so many times that I could tell when he was "getting close", or when he would delay his cumming until he got to a favorite part of the magazine. Sometimes he would cum in 2 or 3 minutes, and sometimes he would take 15 to 30 minutes. I loved watching how his legs would stiffen, and how his stomach would move in and out as he was stroking. He was very well built, and a great athlete. Of course his breathing turned me on too! ( Btw, I guess I would say his cock was average....about 5 to 6 inches long but nice and thick with big balls.)

Most of the time when he would cum he would put the mag down, and lay back and shoot his cum all over himself. He was young enough then too, that his cum would sometimes shoot over his head. He would "duck", LOL, but sometimes I knew he shot himself in the face! He came a lot too. I have seen Peter North, the porn star, videos and believe me, back then he had nothing on my brother! Yes, I would masturbate most of the time when I was watching him. I think I had my first orgasm watching him too, but didn't know what it was at that time. I brought a little stool into the back of the closet, and would sit on it with my panties in my mouth so I would keep quiet. I was just fascinated with the cum shot. I could tell how much he was turned on by the amount of spurts that he did. I counted 12 one time! One day he was so turned on, that he jacked off 3 times in about 4 hours. I noticed that each cum got a little less, and more clear in color too.

Honest, I never really thought of going in and telling him that I wanted to jack him off, but I knew that I could not wait to get my hands on a cock of my own! My watching big brother lasted about a year and a half, until he moved away to college. By then I was masturbating about once a day, sometimes twice, and using the memory of my brother to get me off. Oh, and reading "Penthouse Forum" too...lol. Thanks Dad!

I finally got my hands on a real cock when I was 15, and the boy was 16. We were on a day trip with another family, and his dad had one of those extra long vans. The two of us were way on the far back seat and "horsing around" as kids will do. It had been kinda chilly so we had a blanket covering us too. Well, one of the times when we quit, my hand ended up resting on his leg near his upper thigh. I noticed that he was kinda squirming a little but I didn't pull my hand away. I moved it slowly up toward his crotch, and I could feel that he had a hard on. I was getting turned on myself, and I thought I'm not going to stop now. I started to rub his cock thru his pants, and he got very hard, and was very uncomfortable. He looked at me with a look that said, "Don't stop," so I reached over with my other hand and undid the snap to his jeans and unzipped his fly.

We both did a little gasp when I had my bare hand on his cock. It was kind of like a Eureka moment for me to finally touch a bare hard cock. Thank goodness no one was paying attention to us then either. I felt the whole thing and his balls. I was just loving the fact that I had my hands on a cock finally. He lifted himself up so that he could slide his pants down to his knees. Again, at that point we were both so turned on that we were taking a lot of chances. He already had precum dripping down from it and I was feeling the cum and rubbing it back on to the head of it. I had my head up by his shoulder and he whispered to me, "Don't stop, keep stroking," and I whispered back to him, "I know what to do!" 

I started stroking him as if I was doing it to my brother, by alternating fast and slow strokes. I could feel him stiffen, and I watched as his legs would jerk as I increased my strokes. I could tell that I was soaked in my panties, but my pussy could wait as I was going to see my first cum by my own hands. All of a sudden I could tell he was going to cum. He put his head back and was breathing so as to not make too much noise, and his cock was very, very, hard. Just before his first spurt I noticed it started to drip like crazy, and then his legs stiffened one last time as his first spurt of cum shot up onto his chest. He shot about 3 long streams and the 4th one or so hit me on the chin.

I finished jerking him, and he settled back down on the seat. He had cum all up on his sweatshirt, and some on my face. He actually had a glazed look on his face and I thought for moment he was going to pass out.

Long story short.....lol....after we got cleaned up as best we could. His dad stopped for a rest room break and I went into the ladies' room and masturbated to an orgasm in about 2 minutes I was so turned on. I still had cum on my hands and it was squishy, and I finally licked it off. My panties were so wet that I just threw them away in the restroom wastebasket. He told me later that it was the first time that anyone had ever jacked him off besides him.

Well that got me going to say the least. I could not wait to do it again.