One night it was warm and my window was open. I guess hers was too, because after I was in bed in the dark, I could hear her having sex with some guy. Her shade was down and lights were off so I couldn't see anything, but her window was also open, so the sounds were plain as could be. I kept quiet and kept the lights off, naturally, but masturbated to the sounds.
A few weeks later, again after I was in bed in the dark but not yet asleep, my neighbor's lights came on, and the shades were not pulled down. She had a man with her again. I didn't see him at all because he was lying on the bed, too low to see through the window. But I was able to watch her sit up and take her top off. She leaned forward and out of sight again, but was making out lying on top of the guy. Before long she stood up. From her motions I could tell she was pulling her pants off, though I couldn't see below her waist. She got back in bed and had sex with the guy, straddling him on top. The windows were closed this time so I couldn't hear anything, but as before I masturbated while watching the woman's bare top while she rode the guy.
Years later I lived in the top flat of a three-decker with three roommates. I was growing some plants on the roof, and just generally liked to hang out up there, but there were no stairs or ladder or other feature of muy building designed to provide roof access. To get up there I would climb out the window of my room onto the roof of the building next door, and climb again from there to the roof of my own building. The other roof was higher than our second story but below the roof of our third story. The buildings were so close together that all this climbing was very low risk.
My apartment building filled out the entire footprint of the property, and so the windows were recessed in wells, kind of a concave notch cut into the floor plan so that there was a shaft of air between the windows of my building and the wall of the building next door. These wells made it possible to see into the windows of top-floor rooms in my house from the roof. On one side you could also just use the roof of the building next door to look in. This side is where the middle bedroom was.
One of my roommates was a round-faced, short-haired woman a little younger than me, maybe twenty-five at the time. She had a guy friend who she would have over and go out with. They weren't a couple but I came to find out that they were "with-benefits" one night when I was on the roof, and happened to see in to her window, They were naked and her guy friend was on top of her. I actually didn't stop to watch for long because the sky was still light enough that I could have easily been seen if they happened to see out the window with me pretty much right there. I wasn't inches from the window or anything, I was at least 10 or 15 feet away from the window, up on the roof looking down with the early-dusk sky behind me, but I would have been pretty visible and obvious.
I found I could also see into the bathroom from the roof. A couple of times when my roommate showered after dark, I climbed out and up onto there to look through the bathroom window and check her out, naked. She wasn't fat but was kind of soft, had smallish tits and a pudgy ass. She was blonde and had a light colored bush. I watched her masturbate with her hand one time. She was watching herself in the mirror. I was never caught.
This same roommate had another friend visit from out of town one time. The visitor was a petite blond woman with long hair. I think they had been college friends. My roommate had switched rooms and was now in one which couldn't be seen from the roof, but you could see into it from the back stairs. Really, it was just the top of the wooden stairs which served as the fire escape, but there was enough of a deck that I would go out there and sit in a chair and get fresh air, look at the sky or whatever. Again after dark one night, I was out there and was going to smoke. I saw dim lights through the windows of my roommate's new bedroom and decided to have a look before lighting up. She and her visitor were lying naked side by side, and my roommate was masturbating her friend with her hand between her legs. They were kissing and feeling each other's chests. I watched for a bit, but my roommate was facing the window, and since it was fairly dark inside her room I thought it might be possible for her to see outside if she were to look, and I thought I might be seen so I stopped watching and went back inside.
The room she had had before was taken later on by another young woman. I didn't know her before she moved in, she was a friend of a friend. She was a slim, slightly short blonde girl who had gone to college with several people I was friends with. She was the ex girlfriend of one guy in particular who was part of this social circle. One night I was on the roof again tending to the plants, smoking, whatever, and I saw through the window, her lights were on and pretty bright. She was face down in her bed and her ex was on top of her, fucking her. I hadn't ever seen him with his clothes or shirt off and was surprised at what a big gut he had. She on the other hand looked sexy as hell, getting fucked lying on her belly. I was sure I couldn't be seen because it was so dark outside and the lights inside were so bright, so I watched until they were done.
