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 in a neighborhood closer to work. What I liked about this neighborhood is that the vegetation is 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 kid, 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. A light from outside the window 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 start 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 crossdresser fantasies in my life, but I never saw them through.
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