First experience as the lawn boy
Posted: Fri Aug 14, 2026 6:53 pm
I lost my draft so I'll keep it brief. I had a summer job at 16, around 40 years ago. In addition, I cut lawns on the side. One day I was finishing up the last job of the day and it was during a heat wave. This house had a swimming pool so I decided to cool off before riding my bike home. I had to wear light sweatpants and a long sleeve shirt because of poison ivy at one of the homes. This home is the new one. The other 4 or 5 I did the prior summer too.
I decided to strip down naked, jump in, cool off, get out before anyone gets home. Problem is, someone was already home. I remember being in the pool for maybe 5 minutes? I swam underwater from deep end to shallow then stood up with my back to the house. I then hear "nice job. Now what do you think you're doing in my pool" or something like that. I turn around to a nice looking lady in a tight shirt and daisy dukes. She's the home owner, Mrs James. I immediately grab my dick. I'm average size, but very tall and athletic built. She orders me out and to walk to her. She's by the edge of the patio, probably 15 or 20 feet from the pool. As I'm walking to her, she says no, hands down. I start looking for my clothes and plan to run away but she tells me she already put them in the wash. I must have been in the water for longer than I thought. I stop for a sec, take a breath and drop my hand. She says again to walk to her. I do, average dick wiggling around. I remember wondering why is she smiling at me. She grabs a camera from the table and starts taking pictures of me! And a few close ups of her holding my dick which immediately sprouts to a 6 inch boner. At that point she goes back into the house with the camera then returns a few minutes later with car keys and purse. She has a small towel that she hangs on my penis and while gripping it again, says she's going out for a few hours and that her daughter will be home soon to put my stuff in the dryer. I wrap the towel around me and it barely covers me. My whole leg is exposed. She leaves and then it hits me. Daughter? Damn.
I'm recalling this from many years ago. I've been reading stories here anonymously for a while now and finally have the balls to write up my first story, which shall be continued
I decided to strip down naked, jump in, cool off, get out before anyone gets home. Problem is, someone was already home. I remember being in the pool for maybe 5 minutes? I swam underwater from deep end to shallow then stood up with my back to the house. I then hear "nice job. Now what do you think you're doing in my pool" or something like that. I turn around to a nice looking lady in a tight shirt and daisy dukes. She's the home owner, Mrs James. I immediately grab my dick. I'm average size, but very tall and athletic built. She orders me out and to walk to her. She's by the edge of the patio, probably 15 or 20 feet from the pool. As I'm walking to her, she says no, hands down. I start looking for my clothes and plan to run away but she tells me she already put them in the wash. I must have been in the water for longer than I thought. I stop for a sec, take a breath and drop my hand. She says again to walk to her. I do, average dick wiggling around. I remember wondering why is she smiling at me. She grabs a camera from the table and starts taking pictures of me! And a few close ups of her holding my dick which immediately sprouts to a 6 inch boner. At that point she goes back into the house with the camera then returns a few minutes later with car keys and purse. She has a small towel that she hangs on my penis and while gripping it again, says she's going out for a few hours and that her daughter will be home soon to put my stuff in the dryer. I wrap the towel around me and it barely covers me. My whole leg is exposed. She leaves and then it hits me. Daughter? Damn.
I'm recalling this from many years ago. I've been reading stories here anonymously for a while now and finally have the balls to write up my first story, which shall be continued