I started mowing yards to make money when I was in the 6th or 7th grade for $5.00 a yard. That included mowing, weedeating and sweeping off the sidewalk and driveway when I was finished. By the time I was in the 8th or 9th grade, I felt the competition of other neighborhood kids who might try to sneak in and grab one of my regulars before I could get to them. Bastards. So to solidify the market, I started this program where I told each of my customers that for $20.00 a month, I would keep the yard mowed. If that meant I had to mow twice a week, during the high growth months, they would still only pay the $20.00, but if I only had to mow a few times during the month, I would still come by and do any needed weedeating, but the cost was still $20.00.
This little business model worked well until I turned 16 and started a real job (McDonald's) and I could no longer keep up with all the lawns.
One of the benefits of having the regular "whenever it needs it" lawn customers, was that as time permitted, I would just show up and mow the lawn and not even bother to ask the customer. Sometimes they were home, sometimes not. This led to one interesting encounter that would fuel my masturbatory fantasies for some time, and that was the sunbathing incident.
There was a couple, probably late 20's or early 30's who lived several houses down and across the street from me. I never really saw the husband, so the wife was the person I dealt with. She was what now I might describe as a MILF, but back then, she seemed slightly frumpy. She always wore saggy jeans and an oversize t-shirt. In Florida at that time, most women (and most of the men actually) were very self-conscientious of their looks, trying to fit the beach lifestyle and such, but this lady never tried. As horny a kid as I was, I never really thought about her.
One afternoon, I rolled my mower down the street, walked around the front yard and picked up a hose to move out of the way, then started the mower and began quickly taking care of the front yard. Once finished, I grabbed my extension cord and went to the side of the house to plug in so I could weedeat the front part before getting started on the back. It was then that I saw the lady of the house taking her lawn chair and moving it away from the back porch further into the back yard, I guess to adjust to the position of the sun. We didn't speak, but I know she saw me because she looked right at me and smiled. It was the first time I had seen her in a bikini, and I remember being a little caught off guard since my only other images of her were in the baggy clothes she normally answered the door in.
So I finish with the front of the house, open the gate and move the mower to the back yard. I started the mower and began on the side. I suspected that by the time I got to the back, she would go in the house and take break while I finished. To my surprise, when I rounded the corner and and saw that she was still laying out in the sun, she had the top of her bikini pulled off.
I don't know how fast this happened in real-time, but for me, it was like slow motion. I remember being almost in shock at the site of boobies, but not only boobies, boobies with no tan lines! The were large and saggy, but did I mention, large? As the mower engine roared and I stood there frozen, she grabbed her bikini top and stood up, covered her boobs (as best they could be) with one arm and grabbed the lawn chair with the other and quickly walked over to the patio. Then, as she opened the sliding glass door on the patio, she looked at me and with a smile mouthed "sorry".
"Sorry"? Are you kidding me, I was about to be a legend amongst my neighborhood lawn-men! I somehow stumbled through mowing the rest of the back yard and quickly trimmed around the patio, but that was as far as it went. By this point in my life, I was still a virgin, so figuring out a way to seduce the frumpy lady with no tan-lines was something that would have to thought about over and over.
The next time I went to the house to collect my $20.00 for the month, I hoped like hell the husband would answer the door, but it was her. She handed me the check and didn't as much as wink, convincing me that there was no chance for us to make beautiful love during our next backyard encounter. I did see her a few more times in her bikini, washing the car in the front yard a time or two, but there would be no more back yard topless encounters during my tenure as her lawn-man.