This happened in my last year of high school. Exam year. Seems like there were a lot of things to keep my mind off of sports and video games--the questions are were getting harder each year. I'm the only male from a group of five siblings (the fourth), and while some people wouldn't bother, it's easy to understand that I need a brother to wrestle or get in a fight with to settle things. Inevitably, everything has to be voted if there were to be any sort of conflicting decisions.
I'm pretty sure should the people concerned were to come across this post of mine, instant recognition and some action might follow... but I don't think they'd be looking for any of these...
Being the only boy, I was taught decency and respect for my sisters...like never yelling at them, or never disobey them. It was frustrating to be on the receiving end of orders yet I kept things to myself and resented everything before I forget about it a day later.
As with any boy who lives among a lot of sisters, I had some exposure to some erotic sights of my sisters. I never knew anything about sex or how grown-ups make babies; but when I was 11 I felt a certain twitch when I saw a sexy image of a female and in the evenings when I was alone in my room I would take of my clothes and just stare at these women wearing only their bras and panties--I had no access to porn--and imagine them with their clothes off. Instinctively I would lie on my bed and press the pillow against my crotch, which became more frustrating, and I didn't knew why but I rubbed my penis on the pictures of the lovely women. It was only later that year when I learned to masturbate but it's a whole lot different from the way other guys normally do it; I kept it in a flaccid state and placed it between my thighs and let it slide out before putting it in again. I hear about men ejaculating before from friends and figured out that the fluid that came out was semen.
My eldest sister is more than 7 years older than me. I'll start calling my sisters A to D according to seniority--I'm a bit fucked up to assign them names less I accidentally write their real names somewhere. When I was twelve, she came out of the bathroom only wearing a shirt, and I could clearly see her shaved pussy. It was only for five seconds as she stood in front of me, aware of me staring, and then walked straight to her room without any notion of alarm that she just let me see her pussy. Maybe she figured at my age it might be no more than an innocent look. God, she didn't know how hard my thing was...
While I had at least something to see with the rest, I never quite had a chance for anything of my sister B. She was skinny, and quite pretty. She never did give me a chance to even let me find her in anything other than something decent...
My sister C meanwhile is a powerhouse. She had beautiful breasts, and the only sister who I have managed to see "everything". We shared a room until she was 12 and moved in to A's room who moved to college. Before that, I had the opportunity to peek under her short skirt when we were in the room reading story books together and when I made fun of her pointing to her panties, she would give a smirk, and told me not to bother her. Sometimes I would find that she didn't wear any panties and that gave me something to laugh at too. But at the time my thing down there wasn't fully functional and you can bet that if it were I'd be jacking off every time then.
As she blossomed into a teenager, I noticed that she had really large and beautiful breasts, not to mention a nice ass. She was the type who loved skimpy clothes, probably because she was proud of her body, and it was nerve-wrecking to always see her around in her short towel after a bath reading a book or watching tv in the living room.
One day when I was 14 I devised a plan so I could watch her naked every day. Our rooms were right beside each other and we had a closet that was built against the wall. Hers and mine were both against that wall, so I started drilling these little holes but only around the height where I could watch her breasts. And for a couple of months I got to see her lovely breasts whenever she changed, but never managed to jack off properly whenever she did because the scenes only lasted around 15 seconds each time. After the few months, I think she noticed as she had her clothes stuffed around the general area of the holes. She didn't say anything, so I was a bit relieved.
Some years later when I was 18, she once came out of her room only in her panties. I was about to enter my room when she came out. She didn't even bother to look at me as she walked to the bathroom, and looking at it damn close was amazing. I couldn't get over those beautiful breasts and to this day I can still picture those white and supple breasts just brushing past me.
But lets move back to my last year of high school. My little sister, D, was about 11 years old. She already had little breasts developing and she was my favorite sister among them. She loves video games just as much as I do and reads the comics that I buy. Unlike my other sisters, D's very intelligent. She nearly always gets straight As ever since she was little and recently she just scored a big examination.
And unknown to myself, I wanted her. Maybe just a touch. Or more. I always imagined what it would feel like fondling her little breasts and hold her close to me. And I would die just to look at her pussy.
It chanced to be school break and we had time to play video games. She would sit on a chair and I would sit on another one just behind her. While we talked and laughed as she gets killed by some monster or villain, I would try to get intimate and move ever closer that my body touched her back. Soon my crotch came nearer and made contact with her bum and I would always disguise it by those innocent "Oh, watch out for that!" and she never ever gave a suspicious look. Sometimes I would tease her by tickling at her ribs, and yes, I tried as hard as I can to grab at her little breasts. I would score sometimes and she never did get suspicious and only said "stop, that tickles!" as we laughed.
And it go a little far. Aroused by what I did, while she concentrated on the screen, I would unzip my pants and let my penis out. Rubbing a little on her bum from time to time, and pressing it there when I HAD to point out a monster, I jacked off (this time properly) as I breathed slowly. When I came I breathed in her ear as my hands collected the cum so as not to stain the carpet.
I never imagined I would be doing that, but it only made me braver to venture into other encounters.
One night I noticed her wearing an oversized shirt she loved to wear. And she wasn't wearing any bra (at least at home). I asked her if she'd like to play monopoly and when she agreed, I told her that I would be going for a quick shower and asked her to set things up. As I came back in only my towel, I sat in front of her cross-legged without anything underneath but still the angle hid my penis from her view. We both sat on the floor as we usually play it and for about 15 minutes I kept making glances when she bent over to look at the board or roll her dice...
Those wonderful nipples...
My penis was getting harder as each minute passed and I knew what I had to do. I deliberately brushed a little of my towel and it kind of made towel move a little bit, exposing some flesh of my raging penis. My little sister wanted to say something as she laughed but said nothing as I watched her eyes look at it. Soon she wasn't being able to concentrate and suddenly when I reached JAIL, I said "oh no!" and my towel fell by the side exposing the hardest of hard ons I ever had to my little sister's innocent gaze. I pretended not to bother but little traces of cum started to dribble out and she asked if I was peeing. I said no, it's not pee but some kind of fluid before acting a bit embarrassed and covered it back.
I knew I had to do something about my raging hard on, so I had to end the game quick. I admitted defeat, but just before I went to my room, I tickled her saying congratuations, you beat me. It went further and further and soon my body was on top of her as I alternately reached for her ribs, and then with both hands grabbing her breasts. We were on the floor for a few minutes of that fun struggle, and I was totally naked as my towel fell off. I pressed my crotch against hers while I grabbed on those soft breasts but I soon I know we had to stop. She was still laughing and I got up,...and went to my room to jack off.
