I had been pretty oblivious to the whole boy thing throughout high school until 11th grade. As I mentioned I went to an all girls school. In had my first real boyfriend that spring. One of my brother’s friends invited me to the junior prom at their school. This was fun because I my brother was there an all his friends whom I knew. I liked Jim and we started hanging out.
I had bought a new bikini and asked Jack to tell me if he thought it looked good. I tried it on in the bathroom and went into his room. Jack laughed when he saw me because I was ghost white. Then he looked down at the bottoms and said that it looked bumpy down there. What he was referring to was the bulge caused by a growth spurt in pubic hair since the last summer. He said that I should shave it off. I was like NO WAY. I had never needed to do it until then but I had friends who did and complained that it itched like hell as it was growing in. I went back into the bathroom and trimmed it down and showed Jack again but he said that it was still visible. I was ready to bring back a perfectly nice bikini when I dared Jack to a contest. I said I could take shaving mine but there was no way he could stand shaving his. (Now we had gotten over the shyness of early teen years and while we didn’t exactly parade around naked if one of us was in the shower or whatever we didn’t exactly care if the other saw anything.) So he took up the challenge. We went into the bathroom and I got a new razor that I used for my armpits and legs and using Jack’s shaving cream, shaved my pubic hair. I handed Jack the razor and said it was his turn. He lowered his pants and lathered up. I laughed at how apprehensive he was to have a razor so close to his willy. (Boys are so much more complex than girls.) Well for the next few weeks we were both a sight. I would catch him rubbing his pubic area as the hair grew in. I took care of that problem by just shaving every 5 days or so. I think I got the better of that dare.
Having a shaved pubic area meant that when Jim and I messed around there was much more stimulation on my clitoris. I had been masturbating since I was much younger but Jim and I would get hot and heavy and ultimately got to second base but a combination of my parents rules and my not wanting to get pregnant kept it that way. (By second base I mean we didn’t do anything under our clothes just over them.) Needless to say I was frustrated and started masturbating much more. I would estimate that I was probably doing it 2 times a day on average and more on the weekends. I was fairly naïve for a 17 year old mostly because our parents put filters on all the computers in the house. So even if I wanted to look at porn the filter would block it. Jack got around that by going to friends houses but I didn’t feel comfortable with that.
Well with all that masturbating I found myself getting sloppy. I almost got caught by my mother when I didn’t realize I left my room door unlocked and didn’t hear her come in from work. I only realized she was home when she hit the top step which always squeaked. I dove under the covers and told her I was sick and had the chills which she believed. One Saturday before school ended that year mom and dad were out playing golf (which they did a lot) and Jack was at a lacrosse game at his high school. I got off the phone with Jim and was feeling horny. I put my techno trance music up loud and slipped off my pajama bottoms and started going at it. Now one thing is that I have these really sensitive nipples and like to rub them when I’m doing IT. I know some girls don’t but I do. So I was wearing a tank top and no bra so after rubbing myself down there for a while I slipped down the straps of the tank top and were rubbing my nipples with one hand and my privates with the other. The music was really loud and I would actually get into a zen-like trance when I was doing it. I would typically get 3 or 4 orgasms at a time and this time was no exception. When I was finally finished I opened my eyes and looked up to see Jack standing in the doorway from the bathroom to my room. I had forgotten to close it and I didn’t hear Jack come in. When I realized I was there I pulled a sheet over me and screamed at him to get out. Instead he came into the room and I could see that he was obviously aroused. He sat on the bed and kept saying that that was the most incredible thing he ever saw. I told him I thought he was a perv and that I was his sister and he shouldn’t be having the thoughts he was having. He denied having any sexual feeling toward me but said what boy wouldn’t be aroused by the sight of any girl masturbating and I kind of bought that reasoning. (For the dirty minded among you, Jack and I have never messed around like that!!!) I told Jack to leave and he did and I got dressed. I went into his room and said that he owed me something for what he did and saw. He said what did I have in mind. I first made him promise that he would never fantasize with me in the picture because that would be sick. He agreed. Then I had an idea. Jim and I hadn’t done anything under our clothes but I was curious. I clearly knew what a penis looked like but I didn’t really understand how it worked. I told Jack that in retribution, I wanted to watch him jerk off. Now I know some of you are saying “ewww,” how many girls out there would either like the opportunity to see how is works before you ever had to touch one?
So Jack thought that was fair (we are a strange couple, aren’t we?) but said our parents were probably coming home soon. That night however our parents were going out with friends and Jack and I had an 11 pm curfew. When we got home I asked Jack if Dad said what time they’d be home and he said Dad said they’d be late, probably like 1 am. I told Jack that it was payback time. He sighed and agreed and said how do I want him to do it. I told him I had no idea but that he should just do what he normally does. Now I was sitting on the edge of the bed and he said it was too weird with me sitting right there on the bed. I agreed and went and sat on the window seat that was about 5 feet away. Jack went to the bathroom and came out in a tee shirt and boxers. He protested that this was going to be weird and he got on the bed and tried to do it. It was so funny because it just wouldn’t work. No matter how much Jack touched it and pulled at it it remained soft. Finally he said that I was inhibiting him. I suggested that he get a magazine that I knew he had hidden in his closet. He got up and got a Playboy magazine and opened it to the porno pictures. He propped up the book on a pillow and started pulling his dick. This time it responded immediately. I was surprised how big it grew almost doubling its length. I was also surprised at how rough he could be with it because I had always thought these were sensitive areas for a boy. I tried to ask him about it and he yelled that he had to concentrate so I should shut up. LOL After about 3-4 minutes Jack’s willy ejaculated with all this stuff shooting all over the place. He said something like oh shit I forgot to put a towel down as the white semen went all over the place. He pulled his boxers back on and went into the bathroom to get a towel to clean up. I was surprised to see that he remained hard for like 10 minutes after his orgasm. I asked him if I could ask him questions and he said sure. I wanted to know if boys like it that rough and he said that it wasn’t that rough but the sensitive parts are the balls not the dick. He also said that boys like it fast. I asked him if he knew what a blow job was and he explained it to me. I was surprised to hear that a girl could stop before a boy ejaculated and the boy wouldn’t then do it in a girl’s mouth which at the time I found disgusting. That was our next extreme dare, so to speak. I was greatful for the education because the next weekend I gave my first hand job to my boyfriend Jim.
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