It all started one day when I had noticed our next door neighbor, Myra, working in her backyard. I was 18 and as usual doing various chores around the house. We have a swimming pool so our fences are built slightly higher than the rest of the neighbors for privacy, which, as I found out, also means the neighbors get a bit of privacy as well. As I sat on the roof, taking a break from trimming back tree limbs off the roof for winter, I watched her in her blue jean cut offs and tank top. Myra, not exactly a looker, with dark hair that tangled down her back, she had rather large thighs and big hips that actually tapered to a sort of chubby waist and smaller upper body. I could see her ass sticking out of the shorts as she bent to move the sprinklers around the grass. She then went inside and I sat fantasizing about her. I was wearing shorts and pulled my hard cock out the side of them. A bit of pre-cum had already begun oozing out the tip. I had already jerked off this morning with a prolonged taking over of the bathroom, running the shower to cover my moans and the whacking noise, while I sat on my knees jerking away till I spurted all over the floor, so I was in a constant state of arousal it seemed.
As I fondled my cock lost in my daydream, Myra came back outside, this time wearing a bathing suit, her meaty thighs shaking as she walked, her pale skin nearly reflecting the sun, and bouncing in their bathing top were two tits that absolutely captivated me. I barely could take my eyes off of them. She carried a magazine, towel and glass of some type of drink. She spread the towel out on her lawn at an angle sort of facing me and then as she bent over her tits looked enormous as they hung down and I was mesmerized as she lay down. It was either my bad eye sight or my imagination but I could swear I could see her black haired muff sticking slightly out of her suit as she lay down. I sat there silently staring at her stroking my cock, dreaming of her looking up at me and asking me to come over. As she was wearing mirrored sunglasses it looked as if she were staring right at me, though hidden as I was I thought it impossible. Just as I was cumming from jerking I moved and the hand saw went tumbling down the roof and off the gutter, embarrassed I tried to pretend like nothing was happening, and I guiltily glanced Myra's way and she waved and said, "Hi there, working hard?" Not knowing if she had actually seen me or not and out of embarrassment I climbed the ladder down to retrieve the saw barely mumbling a reply.
I went inside to get a coke and when I finally got back on the roof, Myra had rolled over; she had pulled her bathing suit into her butt cheeks so it resembled a thong and I sat there staring at those wonderful huge globes once again dreaming of fondling them. Putting my mind off of things I climbed up and went back to work, occasionally glancing over to see what kind of view she might give me next.
Now at night I would go out and party with my friends and would come home stoned or drunk or both and horny as hell. Knowing my parents, like clockwork, would be in bed by 11:30 Pm, I would get something to eat and kick it in my room listening to tunes with my headphones. But by 11:45 I had the porno magazines laid out across my bed with my favorite pics and stories before me. My bed was pushed up against the wall under a big window facing the fence that separated Myra's and our house. Straight across was a room that as far as I knew was not used very much as her Master bedroom was on the other side of the house.
I guess because with the lights on in my room, the reflection and the darkness of her house, I thought I was alone and safe and that no one could possibly be watching me as I sat on my knees stroking my cock looking at my favorite porn stars. I would walk around naked all night in my room, posing in my mirror and doing exercises etc.
One horny night, I was following my ritual and was in mid-stroke with my hand all oiled up, when I heard my parent's bedroom door open. In a panic I threw the covers over the magazines and threw some shorts on and quickly turned off the light. As I felt busted and guilty as hell my Mom poked her head in the door and asked if I were asleep, and reminded me, "to make sure I came straight home from school as I had a dentist appointment at four."
"Yeah, yeah, yeah!" I said.
I listened as my mom's footsteps retreated and her bedroom door closed. But I was not thinking about my Mom at that point. I was in shock because when I turned off my light and ran to my bed I was looking straight across at Myra, who was standing in her window staring at me behind curtains. Because without the light the glare was gone immediately, I caught a glimpse of her as she tried to back away from view. Interesting, I thought, so she has been watching me jack off.
I lay in bed staring over the fence at the window wondering if she was still standing there. My cock grew so hard I thought it was going to burst at the thought of her watching me. I was so horny that I lay on my back in the dark and stroked till I shot my load straight up in the air. I slid my magazines under the mattress, cleaned myself off and called it a night.
All day the next day all I could think about was Myra watching me. I was a walking hard on in a daydream as I imagined all kinds of scenarios with her. When I got home that afternoon, I went to my room and looked over but there was no sign of curtains moving or anything and most likely she was still at work. I continuously pranced around my room naked keeping my cock half erect most of the time just in case she might be there watching. I went out that night and came home buzzed. This time I kept my lights off as I suddenly had stage fright; I kept glancing over wondering if she was there but saw no signs of her.
The next day, I was walking around with a hard on thinking of her watching me; it was all I could think about. That and the impressions of her in her bathing suit that day. All I could think about is the sight of her lying there and the tufts of hair protruding out from her bathing suit just like in the magazines.
The only time I had seen a pussy up close besides in a magazine was the summer before. I was at a neighbors pool party and families around our end of the block were there as the husbands had gone abalone diving and they were cooking a big BBQ. All the adults were drinking while we kids played in the pool. As dinner approached, I was asked to run across the street to Jim and Marty's house to get some stuff from their kitchen. I entered the house and went back to the kitchen to gather what they wanted. On my way out the door I took a detour to the bathroom to take a pee. As I entered the bathroom it opened on the other side to the master bedroom and lying face down was Marty naked. I couldn't believe it. I stood and stared and then crept up closer for a better view. My heart was pounding in my chest as I stood over her. Her legs were somewhat spread in the odd way she had fell asleep and I stared at her ass and her pussy. Thick hair grew around her pussy and up the crack of her ass and around her butt hole; of course these were the days when shaving was not the norm. I would have given anything for her to turn over so I could see her tits or more of her body. Guiltily I crept out of her bedroom and back to the pool party as I had now seen my first live pussy and what would become something I fantasized about for years.
Later that night I went out with friends and came home horny and stoned as hell. Once I got past the parental nightly grilling, I went to bed and faked going to sleep. As soon as I heard my parents go to bed I hopped out of bed and turned on the light. I oiled up my hands and my cock and stroked it to a raging hard on, I walked around my room acting like I was busy, the whole time thinking she might be watching. I abruptly turned the lights out and spun to see if she watching and as before I caught a glimpse of her moving away from the curtains as they moved ever so slightly as she retreated. Again I finished myself off in the dark promising myself I would be brave next time and stand on my bed and jerk off facing her.
Oddly enough, I pretty much avoided her, staying indoors keeping away from any chance of seeing her, but in the safety of my bedroom I was a brave exhibitionist. I had no idea what I would say to her if I saw her and it really scared me to death. I mean what could I say if confronted by her? Deny it completely? Claim ignorance that I didn't realize my window was wide open and that she could look right in. Well, that was the truth wasn't it? At least it was at first.
The weekend came and I was forced to do my usual chores, mowing the lawns and gardening, and as I was pushing the mower I saw Myra's garage door open and she backed her car out. As she drove away she waved to me smiling just like any other day. Maybe it was all in my head and I really wasn't seeing her hiding behind the curtains at night. I don't know now. That night I got pretty stoned and drunk and came home really buzzing and as usual horny as hell. This time I was throwing caution to the wind. I turned on my light, tore my clothes off, my cock already hard, I grabbed some Vaseline and stood on my bed facing the window and Myra's window. I leaned against the window sill as I stroked my cock for all I was worth. I shot streams of cum onto my window and down the wall. I stood there cupping my balls and stroking every last bit of cum out of my cock before I hopped down off the bed and turned off the light. But completely disappointed as there were no signs of Myra watching me at all. I finally got brave enough to put on a show and there was no audience.
A few nights later, horny as hell, I did the same thing standing on my bed staring right at what I thought would be Myra if she was watching me and cumming on my window. Again after turning the light off I still saw no signs of her. Maybe it really was all a fantasy. Embarrassment and guilt was all I felt as I laid in the dark thinking what if someone else had seen what I was doing. Friends of mine would sometimes hop the fence late at night and come over to my window to wake me up to sneak out and party. I was risking a lot of potential embarrassment. But when my hormones kicked in I would get so focused and horny I could not think of anything else but satisfying my fantasies and cumming.
