I was younger when this happened to me. Like most guys my age, I mastrubated almost daily and feared that someone would find out. Back before the internet, you really had no idea how common jacking off was and figured that since no one talked about it you were the only guy doing it. I used to steal my Dad’s Penthouse magazines and read the letters while slowly strokin my penis. I would then look at the pictures and bring myself to
orgasm imagining what it would be like to be having sex with one of those girls or having her suck my penis.
I would usually jack off right after school when my parents were at work and my older sister was at hockey or volleyball practice. I would usually have at least 2 hours before anyone would come home and that was more than enought time to take care of business. I was always very careful to make certain that I cleaned up all the cum because I did not want to leave any evidence.
On the afternoon in question, I was in my room, naked and stroking my penis. The Penthouse that I had in front of me was one that I had stolen months ago from the trash and one where I had shot my cum onto many times which resulted in most of the pages being stuck together. But there were still several photos that I had not covered in cum and one in particular that turned me on so much. It was of an asian girl with very long jet black hair and I can still remember the picture where she was laying back in a field with her legs spread and almost no hair on her pussy. Her lips were slightly parted and you coild see just a bit inside where she was pink and very wet. To this day memories of that get me hard and I still jack off to that thought.
I was sitting on my bed, naked and stroking my penis to her pciture. Without knowing it, my older sister (16) had come home and when I heard the floorboards in the hallway creeking, I looked up and she was standing in the doorway. I threw the Penthousee to the floor and grabbed the comfortor to cover my erect penis. My heart was racing and I didn’t knwo what to say.
My sister walked into the room and picked up the magazine. She noticed that many of the pages were stuck together and she told me that she knew exactly what I was doing. I have to admit that I was not very nice to my sister and had told on everything that she did to my parents which ended up getting her grounded quite a few times.
Susan closed the door and told me that she would take the magazine and give it to my mother, but that she would first show it to the girls in my class unless I did what ever she asked me to do going forward. Sitting there covered up, scared to death that she would do just that I agreed. I begged her to please not tell anyone.
Susan then said that I would be expected to do her chores around the house (cleaning our shared bathroom and her nights doing the dinner dishes as well as walking our dog). I agreed immediately. She then told me that she wanted to see exactly what I had been doing when she walked by. I told her no way, but she held the magazine out and asked who she should show it to first. After some arguing, she left the room and then came back without the Penthouse. She told me tha magazine was locked where I could not get it and that if I didn’t want Mom seeing it as soon as she came home in about 15 minutes I had better get busy.
Reluctantly I removed the comforter from covering my penis and let her see me. I was not hard, but as she looked at me sitting there naked I began to get erect. She told me to do what I would if I were alone. I wrapped my hand around my penis and began stroking it for her. I have to admit that my embarassement left my mind and I began to be really turned on by having someone watch me stroke my penis. Susan asked me what it felt like and I told her that it began in my balls and insides and then felt better and better along my penis. I told her I really loved the feeling of my hand sliding over the head and then down the shaft.
I stroked my penis for about 5 minutes and told her that I was going to cum soom. I began stroking faster and faster feeling the orgasm building. She was looking right at my penis, concentrating her full attention on it and that increasd the erotic nature of what I was doing. I stood up and pushed my hips forward, clamping down to hold back my orgasm and stroking very fast and hard. When I csould not hold back anymore, my orgasm started. The first spurt was nothing to speak obout, but the next 3 or 4 flew out of my penis and landed on the floor several feet in front of my. I continued to milk my penis and the cum drianed out and into a small puddle on the floor. I had not cum for about 3 days so the volume was about as great as it ever was.
I sat back on the bed exhausted. My sister was wide eyed. She told me that I was the first boy that she saw cum. She said the girls talked about this all the time, but she had never seen a guy jack off and cum. Nor had she ever touched a penis. She promised not to tell anyone, but she told me that she did expect that I would do this again for her whenever she asked. Before leaving, she dipped her fingers into the puddle to see what the cum felt like. As she left, she wiped them along the doorframe and that truned me on quite a bit. I cleaned up and there was no mention of the days happenings at dinner or later.
Over summer, Susan watched me jack off many times and I grew to enjoy giving her a show. Sometimes she would watch wearing only her t shirt and panties and that got me even more worked up. Even though she was my sister, seeing her long, tan legs and imagining what was under those cotton pantied really got me turned on. She never touched me, but did get very close to my penis when I came. At the end of the summer, she brought home her best girlfriend and made me cum for them both. That was incredible and I guess that’s why I enjoy being watched so much as an adult.
I masturbated for my sister until she left for college. Since then we’ve joked about those days, but never revisited them and I must say I mis her watching.
Categories: Male Solo Masturbation