Bob and I spied on a neighbor lady, and it led to many nights and afternoons of masturbating together.
Our house was near the coast, and I used to wander the trails along the cliffs above the water. There was one trail that led in front of a lodge/hotel and some houses. Nobody thought you could go along there, because the trail was below sight. When I got interested in sex, and began masturbating, I thought, hey, I wonder if I can peek on people there because they have gigantic windows to look at the ocean, and they always leave them open.
The first night I went down there, I didn't see anybody, but it was so exciting that I masturbated twice in the bushes. It was a few more nights before I struck gold. There was a lady, I'd seen her drive by before in the house and she was going in and out of her bathroom and bedroom undressing and taking a shower and then putting on her nightie. I was awestruck.
And I was hooked! After that, I'd sneak out after going to bed and see if I could catch anybody like that. Maybe one in five nights I saw something, but I ALWAYS had a good jerk off no matter what, waiting in the bushes for what I might see.
Well, one day I was over at my friend Bob's house, and we were talking about girls at school. We were too young to be dating, and anyway, none of the girls we were hot for would have anything to do with us, but we love to talk about them and if we got a little peek down their blouse or something. We sometimes said we'd jerked off or something thinking about one of the girls, but that was all.
Well, what I'd been doing was WAY hotter than anything like looking down a girls blouse in school, and I started telling Bob about it. He was blown away. Like, oh, man, I gotta go see this!
He lived across town so he couldn't sneak out like I could, but we arranged to have a sleep-over that weekend. We went to my room early (it had it's own patio doors to outside), but it took forever for my parents to go to bed so we could sneak out. I was trembling with excitement.
We made our way along the trail, and when we went past the bend, I could see that the lights were still on where I'd seen the lady! Awesome!! We got in position, next to a little bush, and I told Bob we might have to wait a while. He kept saying, over and over, 'This is so hot, this is so hot.' And that was making me more and more excited and I just HAD to begin jerking off! I dropped my pants and pulled down my undies.
Bob looked over and said, 'Dude, what the fuck are you doing?'
My penis was already hard, and in my hand, 'I'm gonna jerk off while we wait.'
'Holy shit, really??'
Bob was totally, totally quiet for a while, and then I heard him start to take his pants off.
'You gonna do it too?'
'Fuck yeah, this is hot.'
We waited a long time, playing with our penises, stroking, talking about girls, stroking, talking.
'Oh man, I love to jack off, don't you?'
'Yeah, it's awesome.'
'How often do you do it?'
'Like whenever I get the chance.'
'Haha, me too!'
'Oh it feels good.'
'Yeah. I'm gonna blow if that woman ever shows up.'
'Yeah, I can't wait.'
The lights went out upstairs, and on in the bedroom as she came downstairs. She was in a robe, and went straight into the bathroom.
'Did you see that?? She's awesome!'
She came back out, naked, and pulled something out of a drawer.
Then she came out in her nightie, and turned out the lights.
'Fuck, it's so hot, I'm gonna cum!!!' Bobby moaned for a second and then his jerking stopped. I came seconds later.
'Shit, dude, do you have any tissues? I've got cum on me.' I was totally embarrassed. I wasn't developed enough to have cum. Just a few little drops. I didn't use tissues.
'Oh, damn, I forgot, I'm sorry,' I lied.
'Here, you can use my underpants, I'll throw them in the wash.'
He wiped up and then crumpled up my underpants and I put them in my pocket. Back home, I went to the bathroom, and suddenly pulled them out and opened them up, looking for his cum. There were big wet spots, and some gooey blobs. I touched it. It was thick, not like the little liquid drops that came out of my tip. I got a hard on.
Back in the bedroom, I asked Bob if he wanted to jerk off again. 'Can I watch you?' he said.
Oh shit. I was so embarrassed about not having cum, but I REALLY wanted to see Bobby's cum again.
'Ok,' I said. 'Hey, I gotta tell you, I don't have any sperm yet.'
'Really? I guess, yeah, you're not very developed. That's cool.'
Bobby and I took off our clothes, and he came over to my bed so that we could watch with our flashlights. His penis was really awesome, I couldn't take my eyes off it. Straight, really long and hard, with black sprigs of hair all around. His balls were pinkish. It was so...mature..next to mine. He showed it to me, he showed it off, pulling out the hairs to show how long they were, and comparing balls, his were so much bigger than mine. I felt humiliated but totally hot. My little penis was rock hard!!
We moved around trying different positions, and ended up facing each other with our legs wrapped around each other, stroking. He began to moan again, like he did outside. And then his penis began spurting and spurting gobs of cum. I was, well, it was the most awesome thing I'd ever seen! A few little strokes and I came too...little drops at the end of my penis was all I could show.
I grabbed a tissue and wiped the cum off of Bobby-and me too. Bobby liked the attention. He was pretty proud of his cock-and rightfully so! I tossed the tissue in the wastebasket, and the next morning, after he had gone home, I opened up the tissue and looked again.
Our next meeting was at his house, one afternoon when he knew his mom would be out, he told me to come over. He was worried she would come home early, so he took me out to his yard, behind some bushes, and pulled his pants down. He pointed to a stash of tissues he'd already put there.
He showed off his penis to me again...so big and stiff and awesome hairs. I got the urge to touch it, and just reached over and felt it in my hand. It felt so different from mine-felt huge, bulging and full! Wow. I stroked him. In no time, he moaned again, and his cock began pulsing, spurting, cum dribbling over my hand.
'Wow,' he said, 'that was awesome.'
'Yeah, your dick is really cool.'
I can't tell you all the things we did, but you KNOW we masturbated a lot together after that, and we got other boys to join us. Bob loved to tell them what a great hand job I could give, and every one of them let me do it. I think, before we went to different high schools, that I'd jacked off nine of our friends. Some of the girls found out about it, and one girl made fun of me right to my face. It made me feel really bad, but the next time I was masturbating a guy she knew, I got really hot and turned on thinking of what she said.
Well, that was my beginnings, before high school, when everybody started fucking girls. More about that another time!