I grew up in the sprawling, upper middle class suburbs of NY. At the age of 14, I became more and more focused on two major subject - sports and sex. Sex soon took preference over sports.
I spent many an afternoons and early evenings playing in my backyard as well as around the neighbor- hood. Our neighborhood was filled with very similar families to ours - 2 or 3 kids, a father who worked at a decent job and a mother, who spent much of her days shopping and hanging out with her particular set of friends. My mother was a card player. She played cards with her girlfriends 2 or 3 times a week.
Somewhere in my 14th year, I accidentally stumbled upon an activity which would, in a short time, become my passion - peeping into windows around the neighborhood. It happened quite by accident. I was out in my backyard one evening. The sun had set and I was just sort of hanging out, lost in my own thoughts. I looked over at my next door neighbor's house with no particular intention. I saw that their bedroom light was on and the shade was not fully drawn down. I thought to myself, "Hmmm. I wonder what I might see if I sneak up to the window."
Now let me say that this particular neighbor was not what you would call a beauty. In fact, she was down- right ugly. She was fat and her face left much to be desired. If I were to fantasize about fucking someone, she would be the last one I would ever think about. But the opportunity was there, and when opportunity knocks, we must answer the call!
I slipped up undetected to the window and snuck a quick peek. She was in there! She was fully dressed, but just the idea of watching someone while they didn't know it was very exciting to me. I watched for a few minutes. She went into the bathroom and I lost sight of her. I waited a couple of minutes and then I was rewarded for my patience. She came out of the bathroom and her tits were exposed. She was wearing a girdle and her fat rolls were hanging over the edge of her girdle. She did have huge tits, though. I stared at her with delight. She did a few things in the bedroom as I watched those big tits shake from side to side. I was enthralled. I didn't see much more of her that night, but the bug had bit me. If I could see this fat old bitch, why couldn't I peep at some of the many women in the neighborhood who I really wanted to see? I didn't realize just how easy it would be. I began to make plans for the following night.
I hate to admit it, but that night I went up to my room and jacked off thinking about that fat, ugly bitch next door. Yeah, she was ugly, but I had seen my first live tits and I was really turned on by it, after- all I was 14 and a male.
I couldn't wait for darkness to fall the follow- ing evening. Now, my neighborhood was filled with nice homes. There must have been over a hundred in all. There were lots of windows to peek into. I wondered how many of them had slightly open shades, or blinds, or some way to get a peek at some good looking women.
Finally, that next night came. My parents were pretty lenient with me and let me pretty much be on my own. It was summer and I usually stayed out until 9 or 10 o'clock, giving me a good hour or so to do some serious peeping. I took a walk around the block that night, with an eye towards a bedroom window with a light on. I found one. It was the Grace's house. Mrs. Grace was in her late 30's and she was pretty good looking. She was slim and always dressed nicely. She was pretty sexy. I slipped between houses, unnoticed. I crept up to the window. Sure enough, the blinds were only par- tially closed.
As I later found out, many, many windows were like this. I suppose these people never even thought about someone peeping in their windows. Maybe, I thought, they did it on purpose. Maybe they WANTED some kid like me to get his rocks off sneaking peeks at their naked bodies.
I looked inside Mrs. G's bedroom. They were both in there, lying in bed. Mr. G was a fat, bald guy. I never really liked him and I wondered why she was with a jerk like him. He was lying there in his boxer shorts, his fat belly sticking out. She was wearing some kind of housecoat. It had slid up her legs. I could ALMOST make out her pussy, but it was more imagination than anything else. I made a decision to wait there to see if she would get undressed. There were some bushes around the side of the house and I felt I was pretty safe hiding out there. I'd sneak a peek every couple of minutes to see if she had gotten up. It must have been at least a half hour and I was getting ready to depart when she finally got up. She said something to him, I couldn't hear through the closed window, but I could see she wasn't real happy with him. She kept looking towards him, her lips moving as she started to take off her housedress. I watched with baited breath as she slipped it off to reveal a tanned, pretty body with her bra and panties on. Her back was to me as I watched her. Her hands slipped behind her and undid the bra as it fell limply to the floor. "Turn around! Turn around!" I silently pleaded with her. She slipped off her panties, still turned towards him. Her ass was real nice. White as snow against the tanned body.
She bent down to pick up her underwear and I could see her tits swaying as she did. They weren't as big as my fat neighbor's, but they were nice. Real nice! I watched and waited.
She yelled something at him and then turned quickly and headed for the bathroom. It wasn't nearly enough time to take in all of the magnificence of that naked body. I did, however, get the briefest of glimpses of her fantastic cunt though. I had never seen a real, live cunt before and hers was beautiful. I can still see it before me, even after all these years.
She went into the bathroom and I could hear the door slam. I waited awhile to see of she was still naked when she came out, but to my dismay, she had on a nightgown. I had seen enough, though, to make my first night of peeping a successful one.
Over the course of the next two years, I would make many return visits to Mrs. Grace's window. On very few occasions was I disappointed. The worst was when I got to her window and the blinds were fully closed. Man, was I pissed off!
I began to make almost nightly forays around the neighborhood. It got so I was able to make a sort of schedule. I knew when someone would be getting undressed because those wonderful ladies kept to an almost regular schedule, at least during the week. Weekends were harder because they would go out many times and I would be left with nothing to see. I'd try and find a new woman every night if I could, though sometimes I would spend my en- tire time at one window, watching some pretty lady get undressed...or even more.
I guess it was about the third week of my peep- ing that I got to see somebody fucking. That was an experience! Mr. and Mrs. Samuels. They were going at it pretty strong as I watched and jerked myself off at their window. He really fucked the shit out of her. I had never seen people fucking before and tried to take some lessons by watching them. Mostly, they were doing it doggy style. She had a real tight little ass and he fucked her silly.
I was building up my clientele slowly but surely. In the two years or so that I was doing this, I imagine that I saw 30 to 40 of my wonderful neighbors naked. The amazing thing was that I never got caught. Never even came close to being caught. I attribute it to my great skill at being a peeping Tom. Maybe, though, I was just lucky. I couldn't get enough of this activity and found myself doing it more and more. I would get real pissed off if, for some reason, I couldn't get out to watch my "shows". I hated when it rained, although I even managed to make a few trips in the rain.
I thought I had seen it all in the course of that first year or so, but I was wrong. Every once in awhile, I would get a glimpse of something new and exciting. That first Summer turned to Fall. I turned 15. Soon, Winter had arrived.