NOTES: I’m not prolific writer verbs and tenses may not be perfect, just thought I would share.

This happen to me when I was 40 years old about 10 years ago. It’s after this I started to Crossdress.

About 6 years ago, after the passing of my wife, I moved into the neighborhood closer to work. What I liked about this neighborhood is that the vegetation his well established and it’s private, nice and quiet. When I moved in you get to meet your neighbor, being a “don’t mingle kind of guy”, I wasn’t thrilled about it, but good neighbors are good to watch over the house when you are away or on vacation. At the time, they had a 15 years son, good k**, work hard, polite, good grades etc. He would mow my lawn occasionally when I was out of town. I do travel on business quite frequently and would ask him to keep an eye on it. Over the years, I remained single the thought of having another significant lover never appealed to me. I saw him aged, he didn’t very much growing up, 5’4″ maybe 125 pounds.

The years went by and he started college, he would come back during summer breaks. Last March he turned 21. I took upon myself to give him a gift card to the local mall for his birthday. Last June, his parents took a month-long vacation in Colombia to visit their relatives. The son stayed to watch over their house. I live in a 2-story house and my office is adjacent to their backyard which happens to have a Jacuzzi. One night I was working, and I didn’t turn the light on, was just working on my laptop. The neighbor’s outside light caught my eyes, it was the neighbors’ Jacuzzi light. I was about to go pull the blinds down, as I do not want to be known as a peeping tom. This when I saw him get into the Jacuzzi in a bikini, that intrigued me. I shut down my laptop and became a peeping Tom. He was relaxing, started to rub his hairless body, pretending having boobs and he slowly starts playing with his penis, but clit was more appropriate, that didn’t grow much either as he aged. I started to enjoy the show, I had a few gay cross-dresser fantasies in my life, but I never saw them through.

At one point, he stood up and came. I was really turn on by then. That remained like this for the night, I wank and came. A couple of nights after that welcome interlude from working. Again, being a workaholic, the patio light came on, I was hoping for another Jacuzzi scene. Close down the lid of the laptop and prepared for a peeping tom evening. He stepped on the patio. I should say “she” fully dress in a nice summer dress, wigs, makeup, tan stocking, fake breast, and high heels and sat down on the Adirondack chair with a glass of wine. I was really turn on, I grabbed my crotch and rubbed myself while he/she was rubbing her legs then my cock was urging to come out of my shorts. After a few minutes of stroking my cock watching him rub himself, I decided to grab a beer and go outside. I made sure not to make noise and walk toward “her” backyard. He was rubbing himself and rubbing her clit through a pink pantie, you could see a dark spot of precum on them. This when I made my move.