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My Neighbor’s Surprise


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My name is Jim, an 18-year-old high school senior, and I live with my parents in a nice neighborhood. On our street there are 8 homes and behind out house there are houses directly behind us, so our neighbors are about 30 feet behind us. We have been close to the people behind us since we moved in, and I cut their grass and did chores for them as long as I can remember. About 18 months ago they moved to Florida and sold their house to a husband and wife in there early 60’s. We got to know them and again they had me cut their grass and do somethings like wash their car. After just a month the husband died from a heart attack. And the wife, (Maggy) depended on her son, a lot. Her son, Bob was looking after everything and would stop over 3 times a week to pay the bills and make sure that Maggy was OK.

 

Bob was about 30 something and married to (Dee) a beautiful lady about 24 they were married just over a year. I found out from my father that Bob was the one that took care of all their bills for a number of years since his father had to quit work early because of his bad heart. My dad was telling my wife that Maggy was really bad with money and her husband never gave her a credit card or put her on the checking account. But now that Al had passed away, she would have to have one or the other and Bob was afraid that she will get herself back in trouble. But he had no choice and would have to try to control her spending.

 

Every Monday, Wednesday, and Saturday he would stop and make sure everything was OK with Maggy. He and I got close because we are both big sport fans and we talked sports all the time when he saw me in my yard. This Saturday I was in the yard, and he drove up and waved to me and said we can talk later about the ‘new baseball season that started with a bang’. He went in the house and then I heard some yelling. And I heard him yell, “mom I told you not to buy that now take it back we don’t have the extra money for something like that. Do I have to treat you like dad did mom? If I do I will. Now you come with me right now and we are going to return the TV that you do not need”.

 

I went inside not wanted to listen to him yelling at his mother. When they got back, he was there about an hour more and when he left, I saw Maggy crying through the window. I thought she was sad by the way Bob talked to her and made her return the TV.  Sunday I was in the house when Maggy knocked on the back door and ask if I could help her in the house. I went with her, and she had bought a new computer and needed help to set it up. So even thought I was thinking that Bob was going to go off again, I set it up with the printer and it was not an inexpensive set up. I got it working for her and she wanted to give me a tip, but I told her it wasn’t necessary, and left.

 

Monday I was in the house when Bob knocked on the back door. He wanted to know if I could re-box the computer equipment so she could return it. I told him yes as long as the boxes are still there. He thanks me and ask me to come over if I had the time to do it now because they are going to return all of it. I went with him and again Maggy was crying and standing in the kitchen. While I went and started to re-box the system, Bob lecture her about being so wasteful. He said he did not want to have to punish her like dad did, but she gave him no choice. He then added, “I will punished you just like this every time you earn it, do you understand me mom”?

 

She with her face blushed red said, “Yes Bob, I will do better I promise”.

 

When I was putting the computer and things back in the boxes Bob kept lecturing Maggy, I just got the impression that he may have spanked her from the way he was talking to her. And the way she was rubbing her bottom. I just kept my mouth shut and re-boxed everything in the boxes as they came. Bob thanked me and said to his mother, “What do you have to say to Jim”?

 

Maggy said, “thank you Jim,”.

 

And I left. When I got home, I told my father about what happened, and he just said for me to mind my own business and don’t jump to any conclusion about anything. Bob came over on his next visit and we talked about what happened and I told him, “Bob, it is none of my business. I just wanted to help Maggy when she asks for it”.

 

He smiled and said, “you are very mature for your age, take my phone number and if Maggy wants help with anything she bought or spent money on just give me a call”.

 

I told him “No problem”.

 

He was telling me that he had to go out of town for 10 days for work and that Dee would becoming by to check on things here, he was going to LA and that started us talking about the sport teams there. He said he would bring me back a baseball cap from the Dodgers. I was in the yard cutting Maggy’s lawn when Dee came over.

 

Maggy said to her, “this is a surprise Dee what brings you here”?

 

Dee did not say anything right away just took hole of Maggy by her ear and twisted it hard and did not let it go, she said “I am sure you are surprised I am here to teach you a lesson you will never forget. Bob has your credit card monitored and if you spend more than $75.00, he gets an email about your purchases”.

 

Maggy was in pain and Dee had pulled her by her ear, so she was bent and walked her back in the house.

 

All the time Maggy was saying “No, No, No, AWWWWW let go of my ear AWWWWW”.

 

The door was left open and before I knew it, I heard the sound of a spanking and it was loud. And Maggy was the one that was yelling and then crying. I looked in the house and I could see Dee sitting in a chair Maggy was over her lap, her house dress was up and pinned under her arm being held there by Dee left hand and her panties were at her ankles, Dee's right hand was spanking Maggy’s ass hard and fast. And I mean hard, It was not long before Maggy was promising to be good and not do it again, but the spanking went on just as fast and just as hard.

 

Dee saw me looking in the door and yelled to me to come in. I didn’t want to, but she said, “Please Jim come in and watch Maggy get the spanking of her life, with you watching it will help her learn the lesson she just does not want to learn”.

 

I walked in and as I got close, I could see that Maggy’s ass was already red. But as soon as I was in the room Dee went right back to spanking Maggy’s ass.

 

 And Maggy was pleading, “not in front of Jim please Dee he is just 18, Please send him away, please Dee, please send Jim away”.

 

Dee did not even answer her just kept spanking. Maggy forgot I was there I am sure because she started to kick hard again and begging Dee to stop. But the spanks keep falling.

 

Dee stopped and said to me, “Jim would you do me a favor, I forgot my handbag on the front seat of my car would you be a dear and bring it in to me”?

 

As much as I wanted to keep watching Maggy get spanked I said, “Sure”.

 

And I left and the spanking went on to the car and got the handbag. When I brought it to Dee, I was close, to Maggy’s deep red ass and the signs of welts from the long spanking she was getting.

 

Dee said, “thank you Jim you are a good helper, now sit down and I will teach you how to teach this 62-year-old woman that she is never too old for a sound spanking”. And she reaches into her handbag and took out a large wooden hairbrush. Dee did not waste any time putting it to use.

 

The first spank had Maggy kick both her legs straight out and she yelled “NOOOOOOOOOOOOOOOOOOO, PLEASE, NOOOOOOOOOOOOOOO”.

 

But the spanks were harder, and she was kicking like she was trying to jump out of her skin. Before long she had kicked off her panties and was just a crying mess. I was thinking Maggy was being spanked like a little girl by her daughter in law who was just 6 years older than me, and she was really punishing Maggy. The hairbrush spanking lasted a good 10 minutes until Maggy just was hysterical and defeated.

 

 She stops the spanking and ask Maggy, “what did you learn here today”? 

 

Maggy was crying too hard to get the answer out, so Dee put the hairbrush back to work and the spanks now were to Maggy’s thighs. And Maggy finally got out, “not to spend any money without Bob or your approval”.

 

Maggy was in real pain, and I am sure she forgot that I watched her get spanked. Then Dee asks her, “and if you do what is going to happen”?

 

Maggy again did not answer right away, and Dee spanked her thighs again with the hairbrush and Maggy got out, “I will be spanked by Bob or You Dee. Please Dee Please no more. I will be good Please”.

 

“You get up and go stand in the corner and keep your house dress up with your red ass out for everyone to see what a bad woman you have been and had to be spanking like a little girl”.

 

Maggy did just as Dee ordered and went to the corner, she pointed to a just cried and cried and cried.

 

Dee then said to me, “Jim thank you for being a part of my mother in laws punishment. With you watching her get spanked is something she will remember and be both embarrassed and humiliated by for a long time. Every time she sees you, she will feel terrible, and I hope that it will help her avoid being spanked in the future”.

 

She asks me one more thing, “Would you be so kind to make sure that Maggy does her full 30 minutes in the corner? I have an appointment to get my nails done. I need you to babysit Maggy”. 

 

I said, “Sure Dee, I will watch her”. Dee smiled at me and said, “thank you”. Dee then picked up her phone, I forgot she was zooming the spanking to Bob.

 

She then walked over to Maggy, pulled her out of the corner by her ear and tucked her under her arm and gave her more spanks with the hairbrush saying, “Maggy you will stay in this corner for 30 minutes and Jim is going to babysit you and you cannot come out until he tells you”, and another 10 hard hairbrush spanks landed.

 

And Maggy said “yes I will do whatever Jim says”.

 

Then 10 more spanks and she let her go back into the corner.

 

Then Dee said to me, “you want me to leave you the hairbrush in case she doesn’t listen to you Jim”?

 

And she winked at me, “I don’t think I will need it; she will listen to me after the spanking you just gave her. She won’t sit for a week”, was how I answered Dee.

 

Dee just said, “that is the objective”, and left.

 

Maggy just cried like a little girl in the corner. I watched the time and after about 15 minutes the crying was slowing down. She never said a word to me or turned her head away from the corner. I could not take my eyes off her ass. It was red from about 3 inches above her knees to the top of her ass. I watched the clock and thought to myself that maybe it would be OK to see just how well Maggy will listen to me. So, when the 30 minutes finished, I told her she had to stay in the corned until she composed herself completely.

 

Maggy just stayed there never moving. It was another 20 minutes before she had stopped crying completely and I told her she may come out of the corner.

 

She did and she let her house dress down and looked at the floor and said thank you and wanted to know if she could rub her bottom now. I told her Dee did not say she could not once she was out so go on. And I left her rubbing like mad.

 

The next day Bob called me. He said that he was on the phone while Dee punished his mother, and he gave me a little history about Maggy. He told me, “His father had to spank her often for overspending and they were hoping she outgrew it but as I could see she has not. And spanking her is the only thing she understands”.

 

He said, “that was the first time that Dee has spanked her and having you watch her get a bare ass spanking like Dee gave her may make it a lasting impression”.

 

He then said, “I know that was some show you saw but please if you would do me a big favor and not tell others about it. It is a family matter and we do not need a lot of people who won’t understand this talking about us”. 

 

I told him, “Not to worry I will tell no one”.

 

I spent a lot of time the next day in my yard. Hoping to see Maggy and she how she would react to see me after I watch Dee spank her bare bottom. She never came out and the next day was the same thing. I started to think she would never come outside again she was so embarrassed. This was Bob’s Day, but he was still away so in the early afternoon Dee came up to the house. I knew she was there to check up on things and get the bills for Bob to pay.

 

When She saw that I was in back of the house she walked around. She asks, “Jim you didn’t call so I guess that the bad little girl, behaved, and listen to you the other day?

 

“She told me that you made her stay in the corner a lot longer than 30 minutes”. I told Dee.

 

“Yes, I did, I wanted to test her to see if she would listen to and order I gave her, so I told her that she had to stay in the corner until she composed herself”.

 

Dee gave me a hug, “That was perfect I can’t wait till I tell Bob the reason”.

 

I got a little mad at Maggy, she complained to Bob and Dee because I made her stay in the corner longer that Dee said she had to. The more I thought about it the more it was clear to me that she was trying to make me look bad like I was being bossy for no reason. Then I realized that once I explained it to Dee, she was very happy and could not wait to tell Bob the reason.

 

I was just about to go into my house when a very red face Maggy came out and ask if I had time to talk to Bob, he was on her phone.

 

I went into her house, and she followed me in. Dee had a big smile o her face but not Maggy. I took the phone from Dee, and he told me that, “Dee explained to him what happened with the corner time and that he was impressed that I gave her a test to make sure she would listen to me when I was babysitting her”.

 

He also said, “that I could be her permanent babysitter when He is out of town and Dee could not get there. If I wanted to job.

 

He told me to think about it and Dee will explain what I will have to do if I am called to babysit Maggy.

 

I told him I would think about it.

 

Watching Maggy red face getting even redder while I was on the phone with Bob told me she knew that they wanted me to be her babysitter when they are busy, and she was not happy about it.

 

I gave the phone to Dee, and she spoke to Bob a little longer then said I will show him now and said “goodbye”.

 

She hung up the phone and said, “that they were hoping that I would do this for them. Bob got promoted and was going to be traveling more and she was busy so it would really help if I could help them out”.

 

She said, “it would not be hard. Because I am so close it will be easier for me to do and that would help them a lot”.

 

I ask her, “what would I have to do”?

 

Dee said, “You would watch Maggy just like Bob does. I only fill in when he is too busy”.

 

“Explain what I will have to do”? I wanted to hear that if she did not do as I say I can spank her just like Dee did last week.

 

Dee knew that is what I was asking so she said, “Maggy tell Jim what happens when you disobey your babysitter”?

 

Maggy did not answer right away, and Dee said, “do you want me to show Jim again? I have my hairbrush in my handbag”.

 

Maggy said, “I will get spanked”.

 

Dee said to her, “I am about to get my hairbrush”.

 

Maggy went on to say, I will get spanked by the babysitter”. She was blushing to her boobs now.

 

Dee was smiling she said, “now that you know you will have that power over her what else do you want to know”?

 

And I ask, “what I would check on”?

 

Dee said, “I would hold all the house money and credit card and if Maggy needed something she will come to me and if a agree I can give her either cash or the credit card. And then check the receipt and make sure she stayed in the budget you give her that is Bob will go over her limits you will just monitor them daily”.

 

“And If I find she needs to be punished “? I wanted to know.

 

“You punish her, you saw how I did it last week. The way you handle the babysitting after that spanking, is what told Bob you were mature enough to be the full-time babysitter”.

 

I ask. “I can spank her bare bottom like you did”?

 

Dee said, “Maggy will you answer that for Jim”.

 

Still all blushed up Maggy said to Dee, “Please Dee he is only 18 please”.

 

Dee just got up and went toward her handbag on the kitchen table and before she got there Maggy said, “yes Jim you can and are expected to spank me bare”.

 

I smiled and said, “I think I am going to have to have you buy me one of those hairbrushes, Maggy they seem to get you to do the right thing fast”.

 

Dee laughed out loud saying, “Bob was right you are going to be a natural for this”.

 

She kept going over the things I would have to do and saying it will be easy for me because I am here every day.

 

Then I said, I will leave it to Maggy, “Maggy do you want me for your babysitter”?

 

Dee by now was holding her handbag and Maggy knew there was only one right answer no matter how much she was against it and in a very low voice said, “Yes Jim. I would like for it to be you”.

 

Dee yelled, “Outstanding”.

 

 And called Bob back and they talked for a little while then she hung up and said, “You start right now Jim. Maggy tell Jim what he has to spank you for today”.

 

 

Maggy started to cry and said, “You told me not to spend more than $100 on the gift for Bob’s promotion and I spent $350”.

 

Jim she is all yours I will watch to make sure she gets spanked hard enough “.

 

I was nervous but I wanted to do two things. Take charge of Maggy and impress Dee.

 

So, I said, “Maggy go bring me a kitchen chair, and be quick about it”.

 

She knew it was going to happen and there was nothing she could say or do about it. Here she is 62 years old and about to be ass naked and spanked by her neighbor who is 18.  She came in with the chair and I sat in it and pulled her over my lap by her arm and she was already crying.

 

Dee walked over and lifted her house dress, smiled, and pulled down Maggy’s panties.  She winked at me knowing I may have had a problem doing that the first time.

 

I remembered that Dee held Maggy’s right arm behind her back and use it to keep her house dress from covering her ass during the spanking, so I did the same. When I had her in the same position that Dee did, I raised my right arm and gave her the first spank.

 

And it was a hard one I know that because it hurt my hand a lot. But did kept the same pace that I watched Dee spank Maggy, and the spanks were all hard and in less than 1 minute her ass was pink.

 

 Maggy let out a really loud “AWWWWWWWWWWW” with the first spank and everyone that came after it.

 

I kept spanking as hard as I thought would get the approval of Dee and I looked over to Dee she had a big smile on her face and said to me “great spanking keeps it going she will respect you more the more you make her ass hurt”.

 

I knew just what she meant, and I gave it to her good and hard. After about 5 full minutes she was begging me to stop and promising to behave and listen. I knew it was not long enough, so I kept the spanks coming till her bottom was as red as it was when Dee spanked her last week and she was crying hysterically. I remember Dee asking her question and then giving her more hard spanks after she answer each one, so I did the same thing.

 

I stopped spanking and I noticed that once again Maggy had kicked off her panties. It took the hairbrush from Dee to get that done and I did it with just my hand.

 

I said to her, “Maggy why are you being spanked”?

 

Trying to talk between cry’s and not saying anything at all. I started to spank the back of her legs and hard and she said, “I did not listen to Dee, and I spent too much money”.

 

She got 10 hard spanks on the back of each leg and then I said, “What are you going to do about it”?

 

She didn’t know what I was looking for, so she got more spanks on the back of her thighs and she yelled out loud,” RETURN IT RIGHT AWAY”. 

 

I gave her another 10 on both thighs and 10 more hard ones on her ass and sent her to the corner she ran to the corner crying.

 

She was crying like a little girl. Dee said to me, “That was perfect, she will feel it for days and I know she has a new respect for you as her babysitter”.

 

Then she said, ‘Make sure when she buys the hairbrush it is solid wood not one of the rubber filled ones. Maggy knows what to buy if she buys the wrong one that you are not happy with go to the store with her and test the brushes right in the store”.

 

She then took her brush and showed me what she meant by being solid wood.

 

She then said, “you are now in charge Jim, don’t be afraid to spank her often. Bob told me there were time when his father spanked her 5 times a week. She will test you so spank her hard and spank her often”.

 

Dee left and as soon as she did Maggy said, “Jim you did not have to spank me that hard. I was not that bad. You just wanted to try to impress Dee”.

 

Before she finished, I took her by her ear the way that Dee did and went back to the chair I sat down and by her ear I pulled her over my lap and started to spank her all over again. I have to say it was easy to lead her around by her ear. I was surprised. She is not a big woman she has big boobs and a fat ass, but she is in great shape for a woman her age. I am a lot taller that her being just about 6 feet tall. Moving her around was no trouble and she knew that she was in for another spanking.

 

Maggy right away while I was pulling her toward the chair that she didn’t mean it and she was sorry.

 

I knew that Dee was right this was a test, and I was going to pass it even if her ass was purple. I laid into her ass and both of her thighs. She was hysterical again, but I was not stopping till I was sure she got my message.

 

After a good 8 minutes of non-stops hard spanks and the most discolored swollen ass I stopped.

 

Then I said to her, “If you test me again, I am going to spank you naked from then on”.

 

And I gave her another 10 hard spanks on each cheek.

 

She said, “it will never happen again never”.

 

And I sent her back to the corner and she went without a word just hysterical and rubbing like made.

 

I never would have believed that this could happen to me. I found I loved the power I have over Maggy, and I look forward to her needing to be punished a lot more in the future.

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