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Peeping Bob
14/05/2024
Not much response on my last story, but that's ok. But this time I need your advice.

In college, just after high school, I worked at a golf course. Great job for a young kid. Washed golf carts, refilled water coolers, locked up at night, even supervised the younger guys that picked up golf balls on the driving range.

The best part was my girlfriend, now wife, lived on a street that bordered the “back nine.” This made many adventures that I may elaborate on later possible.

Her best friend lives across the street, back of the house facing hole number 11. Her parents were going through a divorce, and her mother was acting very free. It was a house with nothing but women, mother and 2 daughters. I was told that the would undress with the windows open and walk from room to room with her tits bouncing around. She was a milf from the neck down. Neck up she had resting bitch face, never smiled. Anyway I made it my mission to see what everyone else was getting to see.

I worked mornings during the week and evenings sometimes too. I was Johny on the spot. Whenever I was needed I would work.

In the mornings I would set up the course, put out water coolers, unlock bathrooms, ride around and do donuts in the dewy grass. One morning the greens crew was mowing a green and the cart path was blocked, so I just had to sit and wait. I look over toward the house and see a few lights on, a steamed up window. Light goes off in the steamy window and the older daughter walks into the next room towel around her head, robe wrapped around her. I turn to see if anyone is watching me or seeing what I am seeing, but by the time I look back she is gone.

Another evening it is getting dark and I am closing up everything. I’m cruising down the cart path and notice that 2 houses up, the side facing the golf course is all glass. That's just asking for a peeping Tom like I was becoming. I start making mental notes.

You may or may not know this, but some folks think peeping is a criminal activity. I dunno, I often give people an opportunity to see me whether it's sex with the shades open or feeding the dog in my underwear. There is a lot to keep track of: people finishing their round of golf, residents walking their dog, reflective surfaces, clothing that will show up in shadows, daily routines of those you wish too see… it's all very exciting.

As summer went on I ventured out after dark when walkers are gone, the course has long been closed, it's a free for all. I first walk to the target house, no lights, nothing going on. I walk back up the hill to the glass house. Lights on, lots of activity. Dad looks like he is chasing the kids around getting them into bed. Mom cleaning up in the kitchen. A light down the hill comes on, I walk back down 2 houses and see the bathroom light on. Younger daughter is putting on makeup getting ready to go out for the evening. She goes out into her bedroom and walks around in her bra a few minutes before putting on a shirt and going out.

I walk back up the hill, not much has changed. Lights still on, mom appears to have poured herself a glass of wine. She sitting at the counter looking through mail or something, sipping her wine. I hear the girl down the street drive away.

Just as I am about to give up the older daughter gets home. I venture back down the hill and she is already in her bedroom undressing. She had always been waspish… played innocent but was a real slut… if you were her boyfriend. She had a nice set of tits, small (compared to her mother and sister) but stood out like she was in space. Just as I was about to do what I came to do it's over. She’s dressed and the light is back off.

I walk back up the hill, and dad is back laying on the bed. I would love to actually go in this house. It's like the kitchen, dining room and bed room were all one room. Wife come over and pulls her shirt over her head. Tits do that sexy drop bounce thing that makes my dick perk up. I watch her brush her hair. Her husband watches her brush her hair. I look around and make sure I am alone and pull out my dick. When she finishes she walk over to the light switch and flips it off. The lamp makes for poor lighting but I can see well enough to finish what I started. She climbs into bed and pulls the blanket up. Husband turns off the lamp. Shows over.

This was the first and best peeping outing.

I tried a few more times at night but never with the same luck. I had better luck in the mornings when I got the shower routine on the best friend’s older sister down. Watched her shower 5 or 6 times. A few of the grounds crew caught on to what I was doing and began taking my spot for the show.

Never saw the mother, as was the original goal. The best friend worked at hooters for a few years and often wore shorts where the bottom inch of her ass showed so she was no challenge.

My question, it's been 20+ years. She has been married and divorced. As far as I know she isn’t seeing anyone. Knowing that she is the kind of person that hired a stripper for her little sisters bachelorette party, do you think she would appreciate being the object of my and others peeping habits?
Poster: Robert Loblaw


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