My brother was a year younger than me. I had seen his penis when he was a little kid and it kind of reminded me of a peanut. About the same size and shape. So imagine my surprise when I accidentally walked in on him while he was masturbating. I didn’t know too much about sex but I immediately realized that what he was doing was an extremely private act not to be observed by a big sister.
But what really surprised me was how big his penis was. Upon reflection it was probably about 5-inches long but at the time, compared to the last time I had seen it, it was huge. Not only was it big, but it was a bright red and the head of it was shiny and slick looking.
He hadn’t seen me and as I stood by transfixed by what he was doing, his body stiffened and his hand started flying up and down his dick even faster. Suddenly he arched his back and let out a groan. Then he collapsed back on the sofa and let go of his dick. Nothing came out of his penis, but at the time, I was not aware that boys ejaculated when they masturbated, and I guess he was too young.
He then noticed me standing there watching him. He quickly stuffed his dick back in his pants and screamed at me, “What are you doing home? You are supposed to be at soccer practice!”
“It got cancelled. But the real question is what are you doing?” I replied.
“I’m masturbating. What does it look like?”
“And why are you masturbating?” I asked.
“Because it feels good, dummy.”
“Do you do this often?” I wanted to know.
“None of your business but if you really want to know, I do it as often as I can because it really feels good.”
I noticed that he had slipped his dick back out of his pants and was slowly massaging it with his thumb and forefinger. It was still red and hard. I am not sure if he was even aware of what he was doing. I think it might have been a subconscious act. I was kind of disgusted by the whole thing so I just walked out and went up to my bedroom. About 15 minutes later Jimmy was knocking on my door. I told him to come in.
“Sis, I am sorry for what you saw. You won’t tell mom will you?”
“No, I won’t tell on you. Your secret is safe with me,” I replied.
About six months later, I caught the little bastard jerking off again. Again, he didn’t see me. This time when his body stiffened and his back arched and he furiously masturbated his penis, streams of white goo shot out of the end of his dick all over his chest and stomach. I had heard about this but of course had never seen it. He kept stroking his cock while more and more juice squirted and then dribbled out. Even after it looked like no more semen was there, he managed to keep milking out drops of the stuff. Finally he let go of his dick and it dropped onto his stomach right into a pool of semen. I was amazed at how much of the goo there was splattered all over him. He was going to have a major cleanup task. While I had been somewhat disgusted the first time I saw him jack off, this time there was something about the whole thing that I found appealing. Maybe it was seeing the cum spurt out of his cock that turned me on.
I walked over in front of him. His eyes were closed and he still wasn’t aware of my presence. “I see you’re still at it,” I said.
His body jumped at the sound of my voice. It looked like he came off the sofa about a foot. Of course it was probably just an inch or two. He tried to cover up but that was impossible. He pulled his t-shirt down. It had been tucked up under his chin to keep his chest and stomach clear for his cum splatter. I saw the jism start to soak through his t-shirt. He grabbed a towel that he had next to him and covered his cock with it.
“A little too late to be hiding everything,” I said, “I’ve already seen it all.”
“Jesus Christ, Heather, what are you doing sneaking up on me? Can’t a person have some privacy?”
“Hey, I live here too and this is the living room. It’s not a private room. You should go to your room or the bathroom and lock the damn door if you want to masturbate in private. And clean up your mess before mom and dad come back.”
He took the towel and started wiping off his cock, which surprisingly was still semi-hard. I watched as he rolled his foreskin back so he could wipe off any cum residue that might have collected there under the prominent head. I don’t mind telling you that I found the scene extremely erotic. I dashed into the guest bathroom that was adjacent to the living room and grabbed a hand towel.
“Here, let me help,” I said. “Take off that t-shirt.”
Easier said than done. He attempted to get the t-shirt off without getting cum all over himself but it was impossible. Once he got the shirt off I took the hand towel and dabbed off globs of cum that had stuck on his face and in his hair. The whole thing was pretty funny and we both ended up laughing. I noticed that his dick was still oozing semen out of the end so I took hold of it with one hand and squeezed it to get the last drops of cum out while I dabbed them up with the towel. Jimmy looked at me in amazement. I am sure the last thing in the world he expected was for me to be handling his dick and cleaning semen off of it.
“Jesus, sis, what are you doing?”
“Just helping you get cleaned up. Do you want me to stop?”
“Oh, no….I appreciate the help.”
I figured I would tease him a bit. “You like it when I squeeze your dick, don’t you?” As I said this I rolled his foreskin back and forth a few times, while squeezing it. And I could feel it getting harder. So I pulled his foreskin back with one hand and started massaging his cock head with the fingers of my other hand. His head rolled back and his eyes closed. I knew he was in heaven.
I wondered if he could cum again. I would love to see that juice squirt out with an up close view. So I began to masturbate him in earnest and sure enough, within a few minutes the semen was squirting out again. Not as much and not as forcefully but still plenty enough to satisfy me, and satisfy him too.
I found out much later that as men get older it takes longer and longer between ejaculations. But teenage boys don’t have much of a problem cumming multiple times in a row.
Our little masturbation session was repeated many, many times in subsequent years and I learned how quickly a teen aged boy could recover between orgasms. I think our all time record was I jacked him off five times in a row with almost no recuperative time between cums. His poor dick was red and raw by the fifth cum which was watery and not much of it. But we both really enjoyed it.