The following story is fiction about immature teen boy who gets babysat by his female classmate. The story contains scenes of spanking. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.

I was inspired by the delightful story by Jeremy Shawn: "A Wonderful Day at the Beach" was at storysite.org/a_jeremyshawn01.html. (Storysite.org appears to be gone but this is in the Wayback Machine .) It is listed as complete and I have not been able to locate any continuation of the story although one certainly would have been welcome.

This work is copyright by the author and commercial use is prohibited without permission. Personal/private copies are permitted only if complete including the copyright notice.

The author would appreciate your comments – pro and con, including constructive criticism, and suggestions. Please take a moment to e-mail.


Choosing My Babysitter

By

[email protected]

My head was spinning for I was very confused and tired. It was late afternoon and I had been on the beach since right after an early lunch when I had just gone out for a walk. I had met a couple of the girls from my eighth grade class. We were all the same age – thirteen – although I was a few months older than both Robyn and Lana. Like most of my classmates they were taller than I. In fact, they were among the tallest in the class. I thought that they were two of the prettiest girls and they both had tits, er, I mean breasts since the sixth grade.

Tory, Robyn's little ten-year-old brother, was with them. He was almost as tall as I was. All he was wearing was a very skimpy brief style swim suit. He wanted to take it off, because he thinks that it is fun being naked, but Lana told him that he would have to wait until we got to the next section of the beach. "Of course, if you want a spanking, then you may take it off here." said Robyn with a little laugh. Tory declined the offer.

They were being very friendly and we talked a lot. I guess that why I am so confused and I suspect that this is jumbled up. They talked about sunbathing, yet they kept their T-shirts and shorts on while I ended up totally naked as did Tory. Yes, I was just in my birthday suit. They explained that it was OK for me to be naked like that because I was still an immature little boy, like Tory, but not for them as they were mature young ladies with breasts and hair below. Additionally, they were mothers-in-training and had babysat a lot which required that they change and bathe their charges so seeing immature naked boys – like both Tory and me – was a very familiar and normal experience. They had even sat a couple of boys who had been older then we all were.

At first I tried to argue that I was not a little boy but thirteen but they explained that it was not just age but development and maturity that was important. They continued and pointed out that girls develop earlier than boys and are simply more mature than boys. Although some of the boys in our class had already started to develop they lagged behind the girls and I, alas, had not even started. They pointed out how my voice was still high and that my pee-pee was still very small and without hair. Tory chimed into the discussion boasting: "My penis is bigger than yours." I certainly did not want to measure like he suggested because I saw that we were both about the same size even though he was three years younger. It would have been embarrassing even if I was just a bit bigger than he was and absolutely horrid if he was bigger.

We went walking near the water and I wished that I could go in. I explained that Mother is very strict and I'm not allowed to go swimming without supervision for my own safety. Not only did they understand but agreed. They also had a solution to my problem – they would supervise me as if they were my babysitters. That was a wonderful solution like last year when my older cousin supervised me. They did not go in because they did not want to get wet but Tory and I got completely wet and had loads of fun, even dunking each other. He was able to dunk me much more than I could dunk him. It was extra fun because I was naked as they never gave me back my swim suit.

They had explained that little boys don't have to be modest, are often are naked on the beach, and that when we walked together, because they were so much taller, I looked like a little boy so nobody would take notice especially as Tory, who was also naked, was with us.

After swimming they made sure I was covered with sunblock all over by putting it on me, even on my bottom and pee-pee. I thought that was wrong but they explained that as babysitters that was just part of the job. Anyway, they did and it felt good. Then we walked and talked a lot more. Tory got the same treatment and insisted that they do his pee-pee twice because he did not want a sunburn especially down there.

I was surprised to learn that my mom was looking for a sitter for me from them. My protests that I did not need a sitter were quickly shot down. It was a surprise but Mom now wanted to join a woman's club that met in the evening. Robyn and Lana knew that Mother never left me alone at night and thus she was looking for a sitter. They explained how they had been functioning as sitters for me since we met and I seemed very happy about it. In fact one of the biggest things that a boy had to get used to was being comfortable naked with his sitter which, obviously, I was with them. I conceded that they were right and even admitted that I had forgotten that I was naked. They said that proved that I was comfortable about it with them.

There weren't very many other things that sitters do out of the ordinary. Although I took showers, a sitter bathes her boy and we had gotten close to that with my being naked and them putting the sunblock on me in way that was similar to having to wash me. I admitted that they were right. Another thing they said was very hypothetical – spanking. Of course, that only happened if the boy was naughty but I was a good boy. "I don't wanta be spanked." I insisted.

"Would you tell that to your mommy?" Robyn asked.

"Er, er, no. She would get very mad." I admitted adding: "I would get it worse then."

"So you still get spanked by your mommy." she said and it was not a question.

"Please don't tell." I begged. They said they wouldn't because that was unprofessional, like a doctor gossiping about her patients.

Lana asked me what I thought of Ginny Murr in the other eighth grade class who was talking about being my sitter.

"I don't like Ginny at all." I replied, "She's nasty."

"Did you know that when nasty Ginny sits that she always spanks the boy so that he cries – just to make sure that he won't misbehave? Of course, that means she spanks very hard." added Lana. I did not know that and I thought it was terrible.

"I hate her!" snapped Tory, "She always spanks and makes me cry when she starts sitting even if I ain't done nothing wrong."

"I only spank when the boy misbehaves." Robyn said. Then she got me to agree that if she was my sitter, then it would be OK for her to spank me if I was naughty because it would be within her job duties. As we were walking, she gave me a couple of pats on my bottom.

"Ginny has probably asked your mom to be your babysitter so you don't have worry about me spanking you."

"That's awful. I don't want her for my sitter. I want you." I said to Robyn. "Please speak to my mommy." I added with a whine.

"OK, Billy, but only if you pass a test." I was puzzled. Robyn sat on a rock and patted her lap called Tory. He immediately ran over and got over her lap. She gave him a couple of love taps spanks. "That was a good boy spanking."

"Good boy spankings are fun and don't hurt. Lana and my sister don't spank me unless I've been naughty but those spanking really HURT!" said Tory covering his bottom with his hands.

Then Lana continued. "As you saw, when I do that, it means that you are to get over my lap for a spanking. It could be a good boy spanking or the other kind – if you did something naughty and earned a naughty boy spanking. Now, let's practice that but I won't really spank you." Robyn patted her lap again and I lay across it. She gave my bottom a few gentle spanks. "How did that feel?"

"That was OK." I got up and we resumed our walk.

After a while we reached the top of cliff that separated the beach from the town. We were near Robyn's place and headed for it. They said I did not have worry about clothes since the boys in that area ran about naked. We did see a couple naked boys besides Tory and myself.

When we got there, I was very tired and wanted to lie down. Robyn gave Tory and me some cookies and milk first. Then she insisted that Tory and I had to have a bath to wash off the salt and sand. Tory and I were put into the tub together. It was the first bath I had in a long time and she was very gentle with me and Lana washed Tory. After Lana dried Tory he went to watch cartoons. After I was dry, Robyn put me into her bed and tucked me in. She had a nice teddy bear just like the one I had (although not worn) which was nice. I had to admit that I would like her for my babysitter.

* * * * * * * * * *

"Billy is such a cutie. Even if I don't get the sitting job I did get to see just how developed or should I say undeveloped he is and gave him a bath." said Robyn to her best friend Lana.

The girls talked for a while, as Billy napped, before calling Mrs. Parkman. After introducing herself, Robyn explained why she was calling. "Billy is fine and he's napping. We met him on the beach and your little boy was very tired when we got home." Then she got to the important question. "I understand that you a considering a sitter for Billy. We talked about that today and he understands that he needs one and would like me to sit him."

Mrs. Parkman talked more with Robyn and was delighted. She had worried that her baby would reject a sitter and now he had asked Robyn to do it. Mrs. Parkman insisted that she would come by to pick up her baby rather then have him walk home.

When Mrs. Parkman arrived she and the girls talked about Billy and his needs before Robyn went upstairs to get Billy. She led him downstairs naked as his clothes were there. Mrs. Parkman took note of that he hadn't any problems with being naked with the girls. He even asked: "Mommy, can Robyn be my sitter?" confirming Robyn's report.

"Of course, dear, we just worked it out after she told me you wanted her as your sitter but now it is time to go home." She led Billy out to the car and there Robyn gave him a bag with his clothes. Soon they were home. The trip was long enough that Billy told, in a jumbled way, about his wonderful day with Robyn and Lana.

After they left the two young ladies were jubilant. "Lana, I really want to thank you for telling me about Mrs. Parkman wanting a babysitter for Billy. He'll surely be fun to sit and play with and won't be any trouble."

"You're most welcome. It was just chance that his mom mentioned it to a friend of my mother and she told me."

* * * * * * * * * *

It was a few days later that I had my first evening job sitting Billy. When Lana and I met him on the beach the previous weekend, we saw that he was immature in all ways. Actually, less mature than we had thought from knowing him at school. Also, since he did not have any problem being treated as a little boy I did not anticipate any difficulties. During the evening I saw how extremely immature he was emotionally. I think that Tory is more mature than he is although he is three years younger.

I got there just before six when Mrs. Parkman was to leave and she had prepared supper for the two of us. All I would have to do was to take it off the stove and serve it. Billy was in his room and when I went to fetch him was on his computer playing games. He was happy to see me and was wearing just superhero briefs. He explained that his mommy had decided that he did not need to wear clothes in the house and he seemed cool about it.

At dinner I found out the briefs were a precaution to protect the furniture. A bit of probing yielded the fact that he often had skid marks in his briefs. Boys are so messy! He told me he wanted to watch a movie after dinner that ran until nine – his bedtime. I agreed that would OK provided that everything was done first so that he could just brush his teeth and pee and hop right into bed just a few minutes late. I believe that rules need a bit of flexibility. So right after supper, I checked on his homework. He was casual about it but I insisted on seeing it. It was a good thing that I did. We had three assignments and two were not done satisfactorily and the third one was not done at all.

"I can do them tomorrow." he said.

I let him know that was not acceptable and that he would be doing them right now. He immediately griped about missing the movie and he learnt that was his own fault. He was further horrified to learn that this was a spanking offence – actually a double offence – because he had he essentially lied about having done his homework as well as not doing it.

After getting my hairbrush, I sat on his bed and had him get over my lap after I removed his briefs. A dozen hard spanks with my hand definitely got his attention and turned his naughty boy bottom deep pink. After a few minutes of applying the hairbrush the deep pink had changed to deep red and he was crying. I had him stand in the corner for ten minutes to finish crying and consider his wrong doing. Then it was homework time. It took him ninety minutes to do it after which I had him pack his stuff up for school so he would not forget anything in the morning.

I was actually looking forward to giving him a nice leisurely bath but it was getting late so I had to just do a quick scrub. Because I had given him a fun one after the beach, he knew what he was missing because he had neglected his homework which was additional punishment. He did enjoy being dried off, however. It was so cute the way his little pee-pee stood up. He brushed his teeth OK and urinated with me watching. Before putting him into bed, I put a clean pair of briefs on him. His teddy bear was the final touch before I turned off the light and closed the door.

I did some of my own homework in advance until his mom came home an hour later. Of course, she got a full report and I got a ride home which was a nice bonus.

* * * * * * * * * *

There were two things in school that happened because of my sitting Billy. One was good. Billy thanked me for making him do his homework because it helped him do well an a pop quiz and avoid having to explain to his mommy why he was late handing it in. He was still happy that I was his sitter and was looking forward to the next time. The other was not so good, but there was nothing to do about it. Ginny was annoyed that she did not get the job sitting Billy.

* * * * * * * * * *

I never expected that we would meet a wimp like Billy when my sister Robyn, her friend Lana and I meet their classmate on the beach. He's nothing like the girls who are the same age for they are so much more mature. Our folks trust her to watch me and she does a good job. It not a problem being nude with her because I don't like clothes and she likes me naked. "Tory it's good that you're naked because then I don't have to take your pants down to spank you." she says with a grin regularly. Well, that's OK because she never spanks me unless I deserve it which is more than I can say for Mom.

At first I couldn't believe that all that talk about a babysitter for a thirteen-year-old but as the time passed I saw what an immature wimp Billy was. Once the girls had stripped him, he looked younger than me. Sis was right about nobody paying attention to him being naked. We did actually fight while playing around in the water which let me see that I was stronger than he was. I'll bet he'll be in big trouble if there is a bully in his class at school. But that's his problem and not mine.

It was just chance that got me to see Billy again a few months later. Our folks were going out but they forgot that Robyn had to babysit Billy. Robyn decided to take me along since she got a ride back home and I could stay up past my normal bedtime since it was not a school night. Of course, we had to have Mrs. Parkman permission which she got. It had been several months since I had seen Billy. Robyn said he hadn't changed any and she was right.

Billy objected to going to bed after Sis bathed him because I was allowed to stay up. When he wouldn't listen to reason and kept arguing he quickly earned a spanking. Sis sent me to get her hairbrush. When I returned she was sitting on the bed and with Billy over her lap waiting.

"I see that the naughty boy is ready for his spanking." I said when I returned hitting my palm with the brush. "Billy you have been very naughty and deserve a good spanking. I wish I could give it to you." My sister smiled and nodded. I'm sure I was grinning when I took advantage of this opportunity and immediately gave Billy a few hand spanks. I loved see my handprints form but the same thing happened to my hand for it turned red. I knew immediately why Sis wanted the hairbrush so I used it to SPANK the naughty boy. I felt so grown up as I delivered spank after spank turning his butt bright red. I must have been doing a good job for Billy was soon crying. It was good that my hand did not hurt or turn red either.

I stopped and offered the brush to Sis who (obviously thought he was spanked enough) said: "Billy, it is time for bed." Billy got into bed immediately without a word not wanting any more spanks. When we were downstairs, Sis told me that I was definitely growing up and that I had done a good job.

I felt so good. "Billy is such a wimp of a baby. He acts like he's only seven not fourteen." I said and she agreed. After that night Sis did not treat me like such a baby. Of course, she still spanks me on my bare bottom when I deserve it just like she should. I also decided that spanking is definitely fun – provided that one is the spanker and not the spankee. I'm looking forward to doing some babysitting soon for naughty boys who need spankings.

The End

© Copyright A.I.L. April 9, 2014

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