The following story is fiction about a boy who was unjustifiably strapped getting sweet revenge. The story contains scenes of spanking, strapping, cuckolding and sex. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.
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We had been neighbors since I was a baby and I'm now sixteen. They were a typical family of father (Mr. Scotty Roland), mother (Pauline) and two kids. Kaci was six and Ryan was five years older than I and from when I was eight until thirteen they were frequently the babysitters of choice for my parents. They were easy to take home and they came with the backup of their parents just a minute away. They weren't bad as sitters but that is not what this is about. It is about their parents. A few times, the parents sat me. Mr. Scotty Roland was unreasonably strict and had a hair trigger for spanking.
The time that is seared in my memory was when I was in junior high school. It was a Friday afternoon and my parents had gone for the weekend and I was to stay with the Roland's. Since their kids were away in college, there was lots of room. I was doing exactly what I was suppose to be doing – riding the school bus home – that afternoon. Unfortunately, the draw bridge got jammed and we were stuck in the traffic jam for an hour as the highway department worked to get the bridge closed and traffic moving again. We were not allowed off the bus and since cell phones were forbidden in school nobody had one of them to call.
The Rolands were furious that I was late and would not let me explain about the bridge. I was forbidden to talk and Mr. Roland yanked down my pants and strapped me with his belt. I lost count after nineteen hard painful cuts as I was bawling. I was sent to bed without supper and the welts lasted a week. When the morning newspaper showed the broken bridge and monumental traffic jam they didn't even say sorry. I vowed to get even. That was the most egregious time but there were, unfortunately, several others.
As a little boy, I had got a crush on Kaci. Of course, she did not return my affection for I was just a little boy she was babysitting. I don't blame her for that. Kaci was the spitting image of her mother who I also saw as beautiful with a lovely boyish figure (my favorite). Once I learnt the term, I knew that she was a MILF. Otherwise, I did not like her although my real hate was definitely for Mr. Roland.
* * * * * * * * * *© YLeeCoyote
It was the summer of my sixteen year. I did not have much to do and my parents had gone for the week. I was allowed to stay by myself although I had several dinner invites from friends so I wouldn't only eat junk food. I also had a long list of chores to do. Actually, I liked that and realized that I could do everything in a day and half if I just concentrated on them. I decided that it was a test so I actually did half of them the first day so I would not fail to do them. I realized that it was important to impress my 'rents that I was responsible.
I was mowing the lawn even though it was hot. It was a good time to do this because Pauline was out sunbathing. That meant that I could observer her glistering body up close every few minutes without being called a peeping Tom. I was wearing only tight short-shorts and sneakers for it was a hot day. As a side effect, I was showing off my nice body and generous package in the shorts.
The fourth time I got close to Pauline, she called out to me. I turned off the mower jumped the fence and walked over to her. I could have talked over the fence but this way I would get a better view and appear to be a polite young gentleman. Since Mr. Roland was overweight and sagging, I would remind her what she did have any more (if ever). Yes, not nice but I really was not doing anything remotely improper.
When Pauline indicated that she was unhappy about the noise, I told her that my parents expected me to do the lawn and I had to obey then and the town ordinance about mowing hours. I almost felt sorry for that thought when I assisted her by spreading some potion on her back a couple of minutes later. I was extremely gentle for I loved doing it even though doing that made my shorts shrink. I wished I could spread it over her entire body. Finally, she said that Mr. Roland was away and asked me to do her lawn. At this time I noticed that her eyes were fixed on my crotch as we made the deal. I agreed quickly for she mentioned a reasonable price and I would have a bonus of ogling her body for longer.
I finished up my lawn and then quickly moved on to hers. I kept eyeing her and she always was watching me. I wished I had a mirror to see if she was watching my ass as well as my package. I almost ran over her flowers when she turned over having forgotten that she had untied the top of her bathing suit. I had gotten to see all of her charming body but the small area covered by the bottom of her suit.
She quickly realized that she exposed herself and apologized while covering up. "It's quite OK, Mrs. Roland." I replied, "I was not offended in the least by such beauty." She blushed.
When I had finished, we went into the house together so she could pay me. Money was definitely not the top of my priority list but she was. I wanted her. I wondered if my sweaty body was also excreting pheromones that would make me irresistible rather than just stinking of work and sweet. When she gave me a cool drink I thought about grabbing her but I remained the gentleman. Actually, she made the first move, although whether by accident or not I don't know. But her hand brushed over my bulge (causing it to harden even more) and she turned red. "I'm sorry." she said.
I grabbed her hand and pressed it back on my junk, saying: "Nothing to apologize for. You seen it all before (not mentioning that was when it was baby sized)." I put my arm around her and pulled her close. She started to say something but I did not want to hear it, so I pressed my month onto hers. I even pressed my tongue forward and she responded. In seconds we were embracing. I practically came in my pants. A lot of skin was touching and it felt great. I wanted more so I pulled the string that held her top on and when we shifted it fell away. It was most desirable skin contact.
I guess I was filling the air with those magic pheromones that make a guy irresistible for she undid the button on my shorts. She just had to lift the tab on the zipper and the pressure I was exerting forced it open allowing me to spring free. She grabbed my love shaft and marveled at it size. Now to be honest, it is generous but not a prize winner in any way so I guessed Roland didn't have very much. Maybe it would have been very exciting to report that I took her right there on the kitchen floor in the mess from our dropped drinks but that did not happen.
Things were a lot nicer and more erotic. After I kicked off my sneakers and stepped out of my shorts, I picked her up and carried her to her bedroom. A nice nest to fuck in. I sat on the bed and when I put her down she 'attacked' me for she dropped onto her knees and started to suck me. "So big." she mumbled several times. She couldn't take all of me but I quickly (far too soon) gave her my man cream which she eagerly lapped up.
I lifted her onto the bed and we lay entwined for a while. I found the bow and opened it so the bottom of her suit fell away giving me full access to her special box. She was begging for it as I mounted her. It took a while to slide deep in her tight love chute. I was not in a hurry. It was a wonderful fuck. It was even better than I had dreamed of for so many years.
I left her blissfully sleeping and I put the mower away and showered. It was later that I realized that her wedding picture was there on her dresser and it 'saw' her give herself to me. I had cuckolded Mr. Roland in his own bed with his image watching. Of course, I had conquered the MILF as well.
Certainly, I was having my revenge. Of course, it was not really complete yet. How much better it would be if she wanted more and if Mr. Roland knew and it consumed him.
* * * * * * * * * *
She most certainly wanted more of my big hard woman pleaser while I was delighted to keep her happy with it. Two or three times a week after school I would drop by and make her feel like a woman. It was a most pleasant chore. I learnt more about her and her family. Of special interest to me was stuff about her husband. I learnt that he had never been a great lover and things had gone down hill from the start. Also that it bothered him that his penis was barely average in length and that he could not satisfy her like a real man should satisfy a woman especially the one who is his wife. With my seven and half inches (nineteen cm) which was fifty-percent bigger than his barely average trouser worm I reached places he couldn't even dream of but she now did when I wasn't in her.
I would never have betrayed Pauline but I was hoping that Scotty would catch us. One day I was a bit late and Scotty came home unexpectedly very early. Pauline and I learnt of this when there was bellowing like that of a calf as we were getting it on in her bed. I had to stop fucking so I could be ready in case he got physical and attacked. "Quiet down and wait downstairs, Babydick, we are busy now." I said and just to emphasize my manliness I groped my upstanding junk as I spoke. He was furious. He rushed me but was so inept that I easily moved out of the way and he tripped. As soon as he fell on the bed, I jumped on him. He had opened his tie so I grabbed it and tied his wrists together behind his back.
I ignored the foul string of invectives he was sprouting and reached under him and opened his belt and pants. I pulled the belt free and got his pants partly down exposing his ass like he had exposed mine so many times. Then I gave him a long hard strapping reminding him how he beat me years ago because of the stuck bridge. He was howling throughout it all. I used the belt to hold his hobbling pants to the tie holding his wrist in sort of a hog-tie. Now that he was secure, I resumed my pleasuring his wife. It was spectacular to enjoy his wife after reducing him to a crying brat. He saw with his own eyes what was happening and he knew that he was a cuckold. Nothing in the universe could ever change that now. It was one fantastic fuck.
When we stopped fucking and unentwined ourselves Scotty was just sobbing. He had just learnt several extremely hard lessons. The little kid whose ass he had beaten so many times had whipped his ass good and hard yet he could do nothing to stop it because the kid was now bigger and stronger. Perhaps worst of all, the law of the jungle had prevailed and his female had also been taken by the young alpha male and she obviously loved it based on her screams of pleasure.
I had one more horror for him. I pulled him into his favorite position between Pauline's legs. She had told me there was one thing that he did well. With his face on her pussy I ordered him to pleasure her. But this time there was a special flavoring – my man cream – in her hole. I guess that this added insult to injury.
"Do it, Honey, do it like you love to." she also ordered. I left them then.
I did not encounter him for a few weeks although I continue to enjoy her bed. He was very unhappy which I was delighted about. He tried to tell me to leave his wife alone but I laughed at him. "We both love it. I get to places you don't even know exist with your baby pee-pee. Pauline told me many times how I make her feel like a real woman." He was turning red. "Don't try anything. I'm stronger than you and the world will laugh and worse if you tell." He sputtered incoherently. "If you interfere again, I'll spank you again and then even fuck your red hot tail." I paused. "Although you probably would love that."
* * * * * * * * * *
Pauline had a surprise for me a few weeks later. When I arrived, Scotty was standing in the corner naked. "Scotty has been a very naughty boy. He has earned a spanking." she said handing me the traditional mothers' implement of choice – a heavy, wide, wooden-back hairbrush. Of course, I cooperated with her. I sat down on the bed. "Come here, boy, time for your spanking." Meekly, he turned and walked over to me. I noticed that he no longer had pubes as I guided him into place over my lap. I started with my hand so I could have the pleasure of seeing my hand prints form on his wicked ass. Then I switched to the hairbrush and gave it to him good and hard. I quickly obscured my hand prints and turned his ass bright red. He was crying.
I was hard and Pauline as just as ready as I was. We quickly stripped and I gave her what she needed (and I loved to do). Then she summoned Scotty to eat her out. I found that terribly exciting and could not resisted that hot red rump he was presenting. I kindly grabbed the lube and applied it to his butt hole. After only a couple of minutes to loosen him up did I mount him. He came before I did and as he ate my cum from her cunt, I filled him with my cum in his back door.
My revenge was complete.
© Copyright A.I.L. September 18, 2014
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Last updated: September 15, 2023