The following story is fiction about a youth's summer job that lets him cultivate his joy of spanking. The story contains scenes of spanking, strapping and sex. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.
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It was another era back then in the fifties and the rules were different. I just turned sixteen since I shared a birthday with Uncle Sam and I had gotten a summer job at Pickett's Lakeside Resort which was just a batch of cabins by a small lake a couple of hours from the big city. The paying guests were there for their summer vacations staying as little as a week to as long as a couple of months. It was mostly families with kids getting away from the hot city streets to enjoy the mosquitoes instead. Also, the lake with its swimming, boating and fishing and the forest with one undersized mountain good for hiking and camping. The nearest little town showed the flicks that played the big cities the previous winter and spring.
I did some stuff on a regular basis for the owners similar to my chores at home – garbage, picking up, minor repairs, running errands and the like – for room and board and a very light pay envelope. The real money was from doing extras for the guests. They had lots of needs and I was there – for a fee – to take care of them. The biggest deal was babysitting of various sorts including hiking and sports. June, a girl my age, for the most part sat the little ones and the young ladies while I got the young gentlemen (the little monsters) who were antagonistic to being sat generally but especially by teen girls. Particularly midweek, when few dads were about, the young moms needed a MAN to keep their tweens and young teens safe and restrained. In many ways the job was sort of like a junior counselor at a sleep-away camp.
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It was one of the earliest sitting jobs I had for the summer. The parents went off to the picture show and I was left with ten-year-old Kris and twelve-year-old Ernie. Their father's last words were: "… and if I get a bad report about you from Roy, I'll use the strap on you Ernie. Do you understand me, young man!" That was definitely not a question, however.
That, naturally, got the standard response. Unfortunately, Ernie turned out to be very, er, how shall I put it, difficult. Before long, I reached the end of my rope and told him that he could expect the strap in the morning since my report would explain how naughty he was. That made a huge difference instantly. He begged me not to tell while promising to be an angel. "You're not getting off that easy, Ernie," I told him, "you have earned a spanking and you'll get it from your dad in the morning." I paused to let that sink in and added: "Unless … you get it from me now." I knew I was getting somewhere because he hesitated and then started to negotiate about getting it from me and how much I would report.© YLeeCoyote
A little while later, a very contrite young man in his pj's dropped his bottoms and lay across my lap after handing me a flip-flop. I never let Ernie know that he was my first spankee but just got a good grip on his waist and gave him something to remember for a long time. The flip-flop was like a small paddle and easily turned him into little bawling boy with his little bottom a bright crimson, fiery, pain center. The now very remorseful boy had a very different attitude and had also learnt that it is not just his daddy's spankings that hurt. His younger brother enjoyed the entire show watching with a big grin. Even now, after half a century, I still remember vividly how it greatly excited me. Even now it still does as I visualize those first cheeks that I made glowing red.
His father's strappings must have been very harsh for later in the week, in response to his mother's saying: "Just wait until your father gets here on Friday." he suggested that I could spank him rather than waiting for his dad. His mother went for that and I got to spank him a second time. This time he got the strap for she insisted. Ernie again dropped his shorts and briefs and bent over the couch so that I could give him a dozen cuts with the strap, which was actually a folded heavy leather belt. Even though I did not swing with all my might, his ass showed each stripe until they quickly melted into two bright red cheeks. He was, much to his mother delight crying so that she knew I was delivering an effective strapping. It was not nearly as enjoyable for me as the first one, perhaps because his mother was watching.
I also found that there were some sexual perks as well. A few of the younger moms with older mates, especially when they were gone more than a week, would be very horny after they got home from an evening with the girls. A line like "The money is in my bedroom." I quickly learnt was a clear invitation and I had the pleasure of knowing several older women in their own beds. It was far more comfortable than the backseat of a car and less expensive since they always had condoms for me to use. I got a lot more than a quick feel with them unlike many of the girls I dated. I discovered that some of them felt guilty about doing it with me or just in general. After I teased some about their being naughty and just as deserving of a spanking just like their naughty sons, I had several of these grown up naughty girls over my lap. A few spanks turned then on even more and then the fucks (and tips) were even better. Let me digress and say that in college spanking my dates (both gals and guys) provided me with much hotter fucks than otherwise for I loved plowing red hot ass.
The biggest surprise was Mr. Karl Platz. He stayed with his kids for a week because his wife had to go to her mother's assistance for a while. He went out one evening and came back both late and drunk. Just a few days before, there had been a fatal crash because someone had been DUI and I gave it to him with both barrels, especially since his wife was so strict with the kids. From the meek way he took it was apparent that his wife wore the pants in the family and disciplined him like she did the kids. A few hints of reporting got him sniveling at my feet begging me not to tell. "You need to be punished, young man." I said. "A whipping is too good for you." I continued. Soon after that, he was naked and laying over the end of the couch while I stood next to him with the paddle his wife used on the kids.
I swung the paddle hard and he yelled. He yelled for every hard pop. He was also crying. I was just about to stop when I heard a little voice behind me. "When Daddy is naughty Mommy always gives him at least twelve, Ray." It was his ten-year-old son. I figured that I should follow family procedures, so I gave him the additional four pops making him bawl.
"And it's past your bedtime." I told the boy who immediately scampered back to bed. I had a pressing need and so I opened my pants and rammed into the available hole. He was even tighter than the women I had and I was pumped up. I had a most explosive orgasm. I slept very well that night and did not have any trouble collecting my fee in the morning from one remorseful man. The next week, when the wife returned, she thanked me profusely for disciplining her errant mate promptly and effectively.
There was one time that things did not go as I would have liked. I took four boys, who were eleven and twelve on an overnight camping trip. They were good summer friends and I had managed to have had cause to spank each of them in the previous month. Since I was never unfair, I did not think that they harbored any resentment for it especially since if I hadn't spanked them, their fathers would have had a few days later. The temperature was sufficiently high that we could sleep under the stars in our sleeping bags.
I guess that was my undoing. Suddenly, I woke up and found that my sleeping bag had been unzipped. The worse news was that I was prone with my wrists tied together behind my back and my ankles tied together surrounded by four jubilant boys. I soon learnt that I was a captive pale face and they were considering scalping me. I thought that they were a bit old for 'Cowboys and Indians' but they had an objective. They did not think that I should always be the one who spanked because I was just a little older then they were. They said that I earned a spanking because I was careless and let myself get captured. Of course, my arguments that this was a sneak attack out of the blue was scoffed at.
They decided they would each get three hits with my belt on my ass to determine if I could take it. My briefs were lowered and my belt pulled out of my jeans. Then, each in turn, knelt by me and gave me the three cuts. I knew that they wanted to make me yell and I had to be super macho and remain silent. They each hit as hard as they could and the belt certainly hurt a lot. I bit my lip to keep silent and was pretty successful. They were impressed and congratulating me as they untied me. They said that I was a good sport and were as good as gold for the rest of the time they were under my care at Pickett's.
* * * * * * * * * *
It was an absolutely fabulous summer. I must have given spankings at least three times a week – boy or girl, man or woman – and I loved doing it. How much better can a job be that pays you for what you love to do. I had some great sex also. I don't like to think that the extras I got were for that but for doing a great sitting job but I know in my heart that's not quite true. Nevertheless, my college fund got a great boost when I went to the bank after I got home Labor Day.
The next spring I got a pleasant surprise for the Mr. Pickett called and offered me the job again. He said not only were they happy with my work but many of the guests were. Of course, I jumped at the chance for there would be many asses to spank and plow. That summer was even better.
© Copyright A.I.L. August 29, 2011
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Last updated: September 15, 2023