I found this site years ago and enjoy reading all of the stories.
I started to masturbate when I was in the fifth grade. I quickly found that I enjoyed it and began to do it a lot. After a few years had passed I switched homes and moved in with my mom. On several occations she almost caught me jacking off. After one occation I found myself getting horny thinking about my mom catching me. So one night I completely set her up. Usually after dinner before she went to sleep, she would come by my room to say good night. My bedroom door had no lock on it, so she would just knock quickly two times and walk in. I lay back with the covers at the foot of my bed and began jacking off. Thats when I heard it: she had gone to the kitchen to put her dishes away from dinner and then I could hear her footsteps getting closer to my bedroom. I just put my head back and closed my eyes. My heart was racing so fast, I could feel it beating through my chest. Then I heard the two knocks and the door opened. I heard my mo say, 'Nathan I...' and then a gasp and then the door closed. It made me so horny that she had seen me. I finished up and for a few days it was a little uneasy between my mom and me. But she eventually got over it and we started to talk again.
A few months passed by and all I could think about was my mom catching me. I began to think of other women seeing me doing it. One day my older sister came over for a visit. She had the same habit of just walking into my room. So I took all of my clothes off and sat in a chair and faced it towards the door. I heard footsteps coming towards my door and then heard it open. It was my mom again. I paused and then kept on jacking my cock. She just looked and me and said, 'Nathan!' and walked out.
A few more months passed and my older sister moved back in with us. One day I had just got home from work and started to get really horny. So I dropped my pants and boxers to my ankles and started to jack off. Not more than three minutes passed and my sister just walked right in. She just cracked a smile and said, 'Sorry,' and walked out. For the next few months I let my mom and sister catch me jacking off on several occations.
All of that made me want to have more women see or catch me. So when I started college, I still lived at home, and there was a bus stop across from one of our living room windows where this one high school girl would get picked up. My classes started late. My mom and sister would go to work early, so I would open the blinds and jack off. It took a few days until this one girl noticed me, but once she did, she didn't take her eyes off me. This turned me on even more. The next day I did it again, and she just watched me the whole time. This went on for a week, and then she brought one of her friends to the bus stop with her. They both just watched me. Then the next week another girl would watch me. I get so horny jst thinking about those girls watching me jack off.
After that it became a habit. I began to go out into my back yard and jack off where my next door neighbors couldn't see me, but some people who walked by could. This carried on until I joined the military, and then I stopped for a little while. But old habits die hard. I eventually got out of my dorm environment and got a house with some friends of mine. While they would be at work I was up to my old tricks again.
A high school girl lived in this house across the way. One day I was jacking off in front of the window. Her friend walked out of the house and shouted, 'Hey that guy is naked!' I immediately jumped out of view and glanced around the corner to see that the girl's mom had come outside. Later on that day though I looked out the window and the girl next door(I can only assume she heard about me) was looking at my window like she was waiting for something. So the next day I waited until about the time that she got home from school and started to jack off. As she got close to her house and saw me, she stopped. She looked away and then back again and then away and back. She went inside and came back out in her bikini with a towel wrapped around her. The community pool was kind of far and most women didn't walk in their bikinis all the way to the pool. So I can only assume that she was doing it for me. As the months went by I made sure that she got several chances to watch me, and her friend even joined in and watched me.
I have lived in numerous places since then and have had several encounters with being caught/watched. Now that I live in Chula Vista, CA, and there are so many beautiful woman out here. I have now taken to driving to some of the local parking lots and let myself be seen by women who are going to their cars. I start out from home and I take my shorts off, so that I can't wimp out. I lube my cock up and start driving. Only one of my front windows is tinted (due to a break in), so I park with the untinted window facing the shopping center. I usually start off far out and check out who is going into the store. I don't like being seen by men or young kids, so I usually look for women who are alone. I don't park right next to them but within a few spots. I love the looks I get. Most of them look and either shake thier heads or keep looking. I usually get smiles from most of them.
My ultimate fantasy is to have a woman see me and just walk up to my door and ask if she can watch. I wish there was a better way to get a complete stranger to see or catch me, but this is what I have so far.
I also like to go to hotels/motels sometimes and wait until I hear the cleaning ladies coming near my room. Then I just unlock the door and lie on my bed and jack off. I actually had one come in. She saw what I was doing, but I covered up and asked her for more towels. Then I started to do it again under the covers so that she could tell that I was jacking off. I actually came while she was in the room.
I hope everyone had fun reading this.