I am a 19 year old Junior in a small college that is mostly women, and I am still technically a virgin. I am very shy and modest and have only had a small number of sexual experiences, limited to two guys (mutual masturbation was as far as I ever went). But I masturbate alone very often. I think about many things when I do, but the one memory that comes back to me most is from a time when I was thirteen and just starting to develop sexually. I still find it amazing that shy little me did such a thing.
At that time, a new family moved next door, with our houses separated by a narrow driveway. I did not know who had moved in. My bedroom was on the second story and looked right across to another bedroom. The lady who had been living in the house all alone, was disabled and I doubt that she ever went to the second floor.
Well, I was walking by the window at night, in my underwear, and when I looked in the direction of the window I noticed someone in the window next door quickly moving away. I got frightened and pulled down the shade. I kept the shade down all the time for days. Eventually I realized there was a sixteen-year-old boy living there with his parents and a sister. I saw him go into the house one day and thought he looked very mature. I was impressed with how muscular he was, and he must have had a recent growth spurt because he was bulging out of his too-tight pants. I was excited that a boy like that would be spying on me, and it really helped my frail self-concept.
Even in those days I kind of masturbated, not fully like now, but I would lay in bed and rub myself gently through my panties, while rubbing my nipples with my other hand. I never thought of it as masturbation, just as relieving my nipples which were always feeling irritated in those days when they were first developing, and therefore rubbing against my clothing all day. Eventually my panties would start to get moist and I would take them off and sleep without them, just in an undershirt.
One day when this had happened I could not stop thinking about the boy next door. I got out of bed and peeked out from behind the shade and saw he was studying at a desk in his room and I had a very clear view. He was wearing an undershirt which showed his nice smooth arms. My room light was out so I was sure that between the curtains and the dark he could not see me. I was already stirred up from what I had been doing in bed, and I just was driven to pull up the curtain and then turn on the light. I put new panties on and casually walked past the window a few times like I was getting ready for bed. From the side I could tell that his room light went out almost instantly. I knew he was watching. That time I just stood in my panties before my dresser where he could see me from the rear, and combed my hair for a long time. Then I went to bed normally.
I did the same thing the next night and the night after, and always he would turn off his light seconds after I turned mine on. This got me very excited when I would go back to bed, and it was at this time that I first was deliberately using my hands to keep the pleasure growing. Finally it happened that one night I built up the courage to undress completely in front of the window. I made sure he got a view of me at all angles. We were learning about masturbation in school at that very time, and I was thinking that this is what he must be doing when he was peeking at me.
About this time I first started masturbating by inserting my finger in and out, and that gave me my first orgasm. I would not strip completely every night, because sometimes I would feel like that was too much, but every few days it would build up and I would do it again and for a longer period-and even try to make sure my movements looked sexy and provocative. This is how it ended: as an immature preadolescent I had the fantasy that he would fall in love with me and marry me-please don't laugh! Well, I saw him in a movie with an older girl (his age) and he was kissing her! I felt so betrayed and hurt and humiliated. I never showed myself again to him. Also, he left for college the following year.