In the early days of my masterbation history, I was so eager to do it that I got careless and sloppy about when and where I did it. The result was that I got caught a few too many times.
I gave myself my first orgasm just before my teens. It was an accident, and I had no idea what was happening as I sat on the toilet in the upstairs bathroom while my little erection shot it's first load of cum ever. A few weeks earlier I had discovered that rubbing my penis felt utterly fantastic, and caused it to get hard and stiff. I'd made no connection between this and sex, and I only knew that I was in love with the sensation.
After that first orgasm, I was an instant addict. Into my 13th year, I did it as often as I could pull it off. As I began to approach 14, the idea entered my mind to be a little bit more bold and creative with where and how I did it. By then I had figured out how sex worked, and I'd made the connection between jerking off and intercourse, which made it even more exciting.
The first people to ever catch me stroking off was a couple in the park near my house. I had positioned myself just off a paved trail, and I was leaning on a fallen log back in the bush a ways. My pants were down around my knees and my 13 year old erection was in my right hand, getting it's much loved rub-down. I had done it outside a few other times, and the sensation and titillation of having an orgasm outside was extra arousing. I didn't mean to get caught, and it was late enough in the day I thought all pedestrians would be done for the night. I was so focused on my pending orgasm that I didn't notice the elderly couple approaching.
He saw me at the same instant I saw him. Our eyes met, then he glanced down, and I knew by the look on his face he knew what I was doing. He looked back up at me and a smile spread across his face. My movement caught the attention of his wife, and she started to look in my direction, but he quickly diverted her attention away from me, and they kept walking.
The second person to catch me was a security guard in the same park. It was past midnight, and I had snuck out of my basement bedroom. I want to a small field of grass, took off my shorts and underwear so I was naked from the waist down, laid down on the grass that was damp with dew, and started to rub my erection against the grass. I wanted to see if I could have an orgasm this way. I have to admit that the overall experiment wasn't going all that well, and I was about to give up (that orgasmic feeling was not building, and humping the grass didn't feel as good as I thought it would), when all of a sudden I heard the sound of a small engine, like a golf cart.
Before I could hop up and get dressed, a pair of headlights swept across me, and I knew whoever was behind them was getting an eyeful of me naked but for a shirt. The cart stopped. I grabbed my shorts and held them over my penis, and tried to shield my eyes so I could see past the headlights. I heard a young male voice say, "Kid, you got balls, I'll give you that. Now get dressed and get home, and if I ever catch you doing this in the park again, I'll detain you and call the cops."
Then he drove his golf cart away. With my hear pounding so hard I thought it would pop out of my chest, I ran home, snuck back in my basement window, got into bed, and finished the job.
The third person to catch me was my older sister. This too was an accident. I had begun to experiment with different kinds of lubricants. Shaving cream, I'd learned, didn't work so well. Shampoo made my penis hurt. Conditioner was fantastic in the shower. My sister, who was 16 when I was 13, had some sweet, perfumed lotion in her bedroom, and I was dying to try it. So one day when I was home alone (or so I thought), I took EVERYTHING off, went into her room, pumped my hand full of her lotion, and began to stroke. As the sensation began to build, I closed my eyes and focused on imagining having sex with a girl in my grade at school (she was a common fantasy when I stroked off.) Just as the orgasmic sensation was starting to develop, I heard her.
"What the fuck"
She said it softly. I yanked my eyes open. What could I do? I was buck spankin' naked on her bed. Her lotion was oozing out from between my fingers, and I had a wad of TP in my other hand ready for the eruption, with some spare near by for the clean up.
"Sorry" I said.
She did me the courtesy of looking away as I walked out of her room. By the time I got to my room, the mood was lost, and my erection had gone down. I got dressed, but didn't dare come out of my room. I was terrified that she would tattle on me.
A moment later their was a knock on the door.
"Yeah?" I said.
"You can keep the lotion" she said. "I don't ever want to use it again. It's on the floor outside your door. Get it when you're done, and dressed."
The fourth time I got caught was at school. At the back of the school auditorium was a control room for the theatre lights and sound system. After school, if there were no drama related activities, that room was always abandoned. And it had a really small bathroom attached to it (nothing but a closet with a toilet and a sink, with a door that didn't lock). I had used it a couple times to jerk off. The idea of doing it in school was so naughty that it heightened the sensation.
Outside the auditorium, the cheerleaders were working on their routines, and they had loud music playing. (One of them was the girl with whom I usually had sex in my fantasies.) Because of their music, I didn't hear someone walking up the flight of stairs to the control room, and I didn't know anyone was there until she walked into the little room. I was sitting on one of the swivel chairs, my pants around my knees, with erection in my right hand. I didn't know her name, but I recognized her. She was not a pretty girl, but not ugly either. Plain. She had braces, big boobs, a wide butt, red hair, and freckles. She was a female nerd. I had never given her any thought until she walked in on me jerking off.
She said nothing, but her eyes got huge and a smile split her face almost in half.
I jumped out of the chair and scrambled to pull up my pants. She said nothing as I ran down the stairs behind her, still pulling my pants up. I thought: If she says anything to anyone, I think I might commit suicide. Death would be better than the whole school knowing I was jerking off in the theater control room.
The next day, I was walking down the hallways between classes, and I saw her walking towards me. She was avoiding my gaze on purpose. But as she came close, I saw a note in her hand. I don't know if we did the hand-off with enough stealth that nobody saw, but I hope so. I read the note as soon as I got to my locker and could read it with nobody seeing it.
"Meet me there again today after school, and I'll do it for you. I won't tell anyone if you don't."
She was already there when I came up the stairs. We didn't speak, but we smiled at each other. I dropped my pants and boxers, and sat on the chair again. I surprised myself at how willing and ready I was to let her see me that way. I was shy about my skinny body, but proud of my erection. And one thing is for sure, I was DYING to know what a hand job felt like.
She knelt before me and took my shaft in one hand and my balls in another. "She's done this before", I thought. As she stroked my shaft she also massaged my testicles, and the sensation was dreamy, warm, sensuous, and soft. The orgasm came quickly, and she let it spill all over my legs. I pulled up my shirt to keep it clean, and my cum spilled onto my stomach too. When it was done, she got some TP from the bathroom and cleaned me up.
"Thank you" I said.
"What's your name" she replied. I told her my name, and she told me hers.
I stood up, pulled up my pants and buckled my fly. "Now what" I wondered.
As if she could read my mind, she said, "I'll let you know if I want to do this again, ok?"
"Ok" I said. And then she walked out. For the rest of the school year, she would smile at me in the hallway if we crossed paths. But she never handed me another note. The next year I was high school, and she, I guess, went to a different one. I never saw her again. But I did hear many years later that this girl was famous in Jr. High for giving handjobs, and she would give one to just about any guy that asked.
The next (and last) time I got caught was my older sister. Again. It was about 6 months after the first time, and a few weeks after the hand job at school.
I came home from school and did what I usually did, went straight to the bathroom, dropped my pants, leaned back on the toilet seat, got a wad of TP ready, and began to stroke. I thought I had locked the door. I meant to. I always had before.
I heard her approach the bathroom, and I didn't worry. The door was locked. I hear her fumble the doorknob, and I still didn't worry. But when the door opened, then I got worried.
"Again?" she said. "Honestly. You need to be more careful."
I scrambled to get dressed, but she she said, "No. Don't. You have to learn to be more careful, and to teach you, you have to finish with me watching. And anyway, I'm curious what it looks like when at the end."
With my pants pulled up far enough to cover my erection, I stood looking at her.
"Are you serious?" I said.
"Yes!" she demanded.
"I don't know if I can with you watching."
"You better figure it out if you don't want me to tell on you. And maybe this way you'll learn to lock the door, and to stay out of my room."
She didn't sound mad, but I could also tell that she was serious. So, I sat back down on the toilet and slid my pants down again. My erection was starting to go limp.
I've read a lot of stories on here about brothers and sisters jerking off together and stuff. I can't relate to that being any fun. I was dying of embarrassment. And my older sister, although good looking enough, was NOT anyone I wanted to fool around with.
I started to rub myself, and prayed that it would go fast. I was surprised at how fast I got hard again, and at how quickly the sensation turned orgasmic. The embarrassment of being caught, and of being watched, was being channelled into some sort of exhibitionism thrill that I had not anticipated. The orgasm came fast and hard, and instead of capping my penis and erupting into the TP like I normally did to keep the mess down, I let myself spew.
She actually clapped.
"Thanks" she said with a laugh. "That was educational." Then she walked out, locking the door as she went.
I never got caught again. Nothing ever happened with my sister again. The next time anyone ever watched me jerk off, I was 17 and had a girl friend. But a decade and half later, I still use the memories sometimes when I jerk off now.
Thanks for reading!