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I've spoken with other people about their "first time" and asked questions like when, where, how it happened, what was it like, etc. Talking about those types of things is guaranteed to keep my attention. But I've never gone into detail about my own experience. I've talked about it in a general sense, but have never descibed the whole experience the way it exists in my memory. I'd like to tell the story now. Although I could start at the point where everything actually happened, it is necessary to back up so that you can understand what happened and also see why. For this reason I need to relate the sequence of events that led up to my story:
I had known Amy for years, ever since I was about five or six years old. She lived across the street from myself and my mother, and used to baby-sit me. I would stay at her house from the time I got home from school until my mother came home from work. Amy was able to do this since she didn't work. She was fifteen years older than I, and our relationship was almost like that of a little brother/big sister. We touched each other; hugs and kisses were exchanged frequently. As a single parent, my mother had very little spare time to spend with me. After she came home she had to get supper ready, and there was always housework or laundry to do. My bedtime was 9:00 until I turned thirteen, which meant that I might see my mother for two or three hours at most. Since Amy had no children of her own back then, she was able to spend a lot of time with me.
I can remember sitting on her lap while she helped me with my homework. We played games together. I learned how to throw and hit a baseball in her back yard. We wrestled all the time; the kind of stuff a kid does. When I was twelve her son was born. Two or three years later she and her husband split up. She received some child care support from him, but not much. Because of that, she went to work. At that time there weren't any day care centers, and I don't think she could have afforded them anyway. She worked part time on the evening shift in a hospital (from 4 to 10) but had to work every other weekend.
After she went back to work my job was to baby-sit David, her son. I was paid $3.00 a night, which was a bargain for her and a lot of money for me. I got home from school around 3:00, changed my clothes, and walked across the street. She would get home a little after 10, and I would then go back home. Often I would stay there and we would just chat. If she went out after work (or stayed out late on a weekend night) I would sleep in the guest bed at her house, sharing a room with David.
I need to say a few words about Amy. She was not very tall, maybe 5'3'' or so. After she had David she gained a few pounds, mainly in her hips and thighs, but she still looked good. She rarely dated. Each night the first thing she would do after walking in the door would be to get out of her uniform. Usually she would change into shorts and a tee shirt or sometimes a nightgown. As I said, it was no different than seeing your sister dressed that way.
Are you dreaming about sexy college girls too?
I was seventeen the night the big event occurred. It was a Saturday night and she had gone out with some of her friends. She didn't get home until well after midnight, and I had fallen asleep on the floor in front of the TV. She had a few drinks in her and was feeling playful. I heard her come in, and had rolled over on my back, still half asleep. The next thing I knew, she was sitting on me and had my wrists pinned above my head. It was summertime, and I was wearing nothing but gym shorts. She had on a sleeveless top and a skirt, but the skirt had fanned out when she dropped on top of me. Her thighs and lower legs were resting alongside my rib cage with her knees just under my armpits. I could feel her bare legs against my torso. More importantly, her pussy was touching my penis, and the only thing separating the two was my thin nylon shorts and her panties.
That fact hit me instantly. I probably became erect in a fraction of a second, which was embarrassing to me. I started to squirm away, but she used her knees to tighten her grip on me. My arms were pinned down and she was leaning forward to keep them there. With most of her weight on my midsection, I was trapped. I had turned my head away from her, but she said, "Look me in the eyes". I did, and remember that the look in her eyes was unlike any I had seen there before. She loosened the grip her knees had on me and began slowly moving her hips back and forth, so that her pussy was rubbing along the length of my penis. This lasted for less than a minute, until she reached underneath her skirt and lowered the waistband of my shorts, tucking it under my scrotum. She then moved her panties aside, grasped my penis, and pointed it vertically. The next thing I knew, I was inside her. That felt incredible.
We were still maintaining eye contact, although I couldn't have seen anything down there anyway; her skirt covered everything up. She started to move up and down, but I came on about the second stroke. Instead of getting up, she stayed where she was. I never lost my erection, but it did soften. After a few minutes I was hard again (at seventeen this is not unusual) and she started sliding up and down again. This time it lasted longer, but I still ejaculated pretty quickly. Obviously I didn't know then that it was a short ride.
After the second time I lost my erection and slid out. I remember being surprised at how wet things were down there, although it was probably mostly semen. I could also feel her pubic hair against my penis and was surprised at how much hair there was. She stayed where she was for a short time, then reached underneath, pulled my shorts up, and stood up. It was kind of a wierd situation. She sat on the couch and patted the cushion next to her. I got up and sat there. She became very serious and told me that I must never mention this to anyone. I said that she had nothing to worry about. I went home a few minutes later.
After that nothing really changed between us. I still baby-sat for her, and we would sit and chat after she came home from work. We did not discuss what had happened. She started to wear a robe over her nightgown, which was a disappointment to me. Up to that point I had never seen a nude woman. Some of her nightgowns had allowed me to see the outline of her panties or her nipples, but now I wanted to see her without clothes. At home I would try to picture her while I was masturbating. Eventually I figured out a way to solve the problem, but it took a while before I actually saw her nude body. Once while baby-sitting I moved the curtains in her bedroom so that I could see in from outside the house without being seen from the bedroom. I figured that I could just circle by her window when I went home, or stand outside on a night she wasn't working. The problem was that she always changed as soon as she got home, while I was still inside the house. The nights she wasn't working she stayed up very late, well beyond my curfew. I spent hours lurking around that window with no success. It had almost become an obsession with me.
One night I pretended to be sleeping on the couch when she arrived home from work. As soon as she went into her bedroom to change, I got up and walked quietly toward the bathroom, which was next to her bedroom. I figured that if she saw me I could pretend I was going to use the bathroom. Her door was ajar a few inches and I was able to peer inside. She was turned sideways, and I got a quick glimpse of her wearing nothing but her panties. I turned around and went back to the couch. When she came out I was still pretending to be asleep, but I had changed position to hide my erection. She turned me over to wake me up, and spotted the obvious bulge. As I was opening my eyes she reached out and began to squeeze my penis. I lay there enjoying it, not knowing what to do next. Finally I reached out and placed my hand on one of her breasts, expecting a reprimand. She did nothing except to half close her eyes. Then, she acted as if she had just made up her mind and stood up. She took me by the hand and led me into her bedroom.
Amy turned off the light and undressed me, then took off her own clothes. She pulled back the covers, and I climbed into the bed. She left the room, telling me that she would be right back. I found out that she went to the bathroom to put in her diaphragm. I quickly jumped out of bed and closed the gap in the curtains I had made earlier, afraid that we would be seen. She came back and got into the bed next to me.
We did not go to sleep at all that night. I could not keep my hands off her. Not knowing if I would have the opportunity ever again, I did a lot of exploring. I loved putting my fingers inside her; the slippery feeling amazed me. I had never kissed anyone using my tongue, and was shown how. I discovered how to make her nipples erect. We had intercourse five or six times. It was an incredible experience.
That night was the actual beginning of a relationship that lasted over ten years. Both of us eventually married other people, but we continued to have sex occasionally. It finally ended when she and her husband moved to Arizona. We still call each other once in a while, but I doubt if we'll ever sleep together again.
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