Where it happened: Friend's house
In my senior year of high school, I used to hang out with this guy a lot and a bunch of us used to always go over to his house after school to hang out. Well, this guy had a younger sister who was two years younger than me. I always thought she was pretty cute. Actually, I thought she was pretty hot. She had such a nice body…smooth long shapely legs and a nice tight ass. We got really close and stuff because I was always over there. I would go over there when I knew her brother wasn’t there so we could be alone. I honestly think I was falling in love with her and I was pretty sure she had a crush on me. We used to talk a lot and flirt a lot with eachother. I didn’t want to do anything though because she was my friend’s younger sister. Anyway, one day, I went over when nobody else was there. She let me in and we sat in the living room watching tv. I couldn’t keep my eyes off her. She had a tight little shirt on that showed off her nice breasts and had on short shorts that showed off her legs nicely, and if I was lucky in certain positions, I got a peek at the cheeks of her ass. We started talking and she asked me if she could ask me a personal question. I thought about it for a bit and said,”Sure.” So she mustered up enough courage and asked,”Are you a virgin?” I was kind of embarrassed, but I answered truthfully,”Yeah, I am.” And she told me that she heard rumors that I wasn’t a virgin. I knew she was still a virgin, she was a good girl, but I asked,”You’re a virgin, right?” anyway and she answered,”Yes.” She said she was glad that I was still a virgin. I asked,”Why?” and she said that she thought it was gross. I said,”Sex isn’t gross,” and she said,”Well, it isn’t gross, but I’m glad you’re still a virgin.” That whole little conversation kind of passed and we just started watching tv again. After a while, she turned to me and asked me if she could ask me another personal question and I said,”Sure, just don’t ask me something you wouldn’t answer yourself.” So, she again mustered enough courage and with some giggling, she asked me,”Do you jack off?” I was kind of taken by surprise by this question, but at the same time it was turning me on. I kind of took my time and then said,”Well, yeah, sometimes…all guys do.” I was lying…I used to jack off like crazy and I still do today. In fact, I used to jack off while thinking about her all the time. Anyway, after that it was kind of quiet between us and then I got enough courage to ask her,”Do you jack off, or I mean, masturbate?” She was kind of giggling and answered,”Kind of.” By this time my dick was getting really hard, but I don’t know if she noticed…I was kind of trying to hide it. Then, out of nowhere, she asked if she could watch me jack off. My heart was racing and I tried to play it cool and said,”Only if I get to watch you too.” She looked really embarrassed, but she said,”Okay, but you first.” So we went to her room and she sat on her bed and I sat on the other end. We just sat there for a while, not saying anything. I caught her glancing at the bulge in my crotch a few times. I was so nervous but I started to undo my pants as she watched intently. I only opened up the front of my pants and let my dick out, only held back by my underwear. I got up and pushed my underwear down enough to let my hard dick pop out. She watched with eager eyes and got a smile on her face. She looked flushed and I probably did too. I was going crazy inside as I grabbed my dick slowly and started to rub. It felt so good…I was so horny with her sitting there watching me. She didn’t take her eyes off my dick as I started rubbing it faster and faster…it felt so good. I was really getting into it and it felt like I was going to cum real soon so I slowed down. I was breathing hard and I noticed that she was too. She started undoing her shorts and sliding her hands into her panties. This was driving me more crazy and I had to stop rubbing my dick or else I was going to explode all over. She slid off her shorts and panties and I got a good look at her glistening pussy. It looked so good. Her room smelled of sex by now with both of us going like that. She started rubbing her pussy as I watched. Her eyes were still glued on me as I slowly started to rub my dick again. I was trying so hard not to cum. I was on fire and from the looks of it, so was she. I couldn’t stand it anymore and I went over to her and layed her down on the bed and started kissing her. We started kissing passionately as I slipped my hands up her shirt and began rubbing her breasts. She started moaning and reached down for my dick and teased it with her fingers. I just knew right then that I had to have my dick in her. I guided my dick to her pussy and pushed the head of my hard cock against her virgin lips. I couldn’t believe this was happening. I slowly pushed the length of my cock into her as she just gasped. She didn’t seem to be in any pain. I was in heaven as I started thrusting my hips. I started pumping faster and harder into her…it felt so good. She just layed there with her eyes closed and her mouth open as she moaned and gasped for air. After about a minute or two of pumping into her pussy, I got that familiar feeling of a pending orgasm so I pulled out and try to compose myself. I pulled out and squeezed right below the head of my dick trying not to cum. I started kissing and sucking her nipples, since by this time, I had gotten her shirt off. I was sucessful in delaying my orgasm and when I thought it was safe, I slid my hard cock back into her and continued pumping. After another few minutes, I was ready to cum and I didn’t want to stop this time, so I pulled out just in time as my hot cum exploded onto her belly. It was the most intense orgasm I had ever had. Spurt after spurt, it seemed to be endless as I was in heaven. When my orgasms had faded away, I was hit with such a feeling of drowsiness that I just collapsed on top of her and closed my eyes. We just layed there like that for about a half an hour or so. After that first time, we went on to try a few other things together, but we never did have intercourse like that again…I think she was scared of getting pregnant and so was I. Shortly after that, I stopped hanging out with her brother and I lost contact with her. I would love to see her again and see if we still have something between us. I loved her then and I will never forget her.