The Mailing List

The Mailing List 14

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.

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PART 14
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From: Benji (Benjamin Grady O'Connor, age 13)

Hi guys. I have some news for you. I have made some new friends, even though it was in embarrassing circumstances. More embarrassing for them than for me, I think, but still...

Anyway, a few days ago Ollie told me that she had been hired to babysit two brothers over the weekend. Their father had to travel for family reasons and he couldn’t tell the boys, so he had asked around the neighborhood for a good babysitter and he had been recommended Ollie. Mom had agreed, so on Friday (yesterday, I mean), after school their dad would drop them off at home. Their names are Tyler and Nolan. Tyler is 13 like me, and Nolan is 11. Ollie told me that they are good boys and that they are on Puericil like me.

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From: Brandon (Brandon Stanley Miller, age 13)

So what happened. Why do you say it was embarrassing?

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From: Benji (Benjamin Grady O'Connor, age 13)

Just because, well, you know what Ollie is like. She’s just so no-nonsense about how she treats boys. As long as you are obedient and have a good attitude everything is fine, but if you try to give her trouble, she’s not taking it.

And, you know, I’m used to that, but some guys find it difficult to have a girl in charge of them, particularly a younger girl. And Ollie is 11... 11 going on 25, perhaps, but still 11.

It’s just a bit weird to have a younger girl telling you what to do, and punishing you if you are bad and stuff, at least if you are not used to it. And I guess Tyler and Nolan are not used to it. At least they were not.

So, their dad dropped them off, with a couple of bags with clothes for the weekend and stuff, and their school things to do their homework and stuff. Mom was not home (you know she has evening shifts at the hospital), so it was only Ollie and me.

You wouldn’t believe how grown-up Ollie can act. She greeted their dad as if she was an adult too, shaking his hand, looking at him in the eye and telling him not to worry, and that she would take very good care of “the children”. (Yeah, she called us that, even though we are all older than her. I mean, Nolan is her age, but we found out that his birthday is a couple of months before Ollie’s, so even he is actually a bit older than Ollie. Not that you could tell by how in-charge she acts. I mean, she treats Tyler and me like kids, so I guess Nolan must seem almost like a baby to her.

I could see that she was making a good impression on their dad. She took her phone number in case it was necessary to contact him, and said our mom could help also if necessary, but that she was sure we’d be OK.

“You boys mind Olivia and do everything she says,” the man warned his sons.

Nolan nodded, but Tyler frowned and asked, “But dad, she’s just a girl! I’m older than her! Why does she have to be in charge?”

Ollie got in front of him.

“I’m in charge because I’m responsible enough to be,” she told him, staring him down. “I have a lot of experience looking after boys. My brother Benji is 13, just like you, but I’m in charge of him, so there’s no need for you to be embarrassed. It’s only natural, because we girls mature faster. Look at me, Tyler,” she added, because Tyler was looking down at his feet. “We are going to have a good time and I’m going to take good care of you boys. But make no mistake, I expect you boys to mind me and, if you don’t, I’ll punish you just like I punish Benji when he is naughty.”

“That’s right,” their father confirmed. “As I told you, you have full authority to discipline the boys if they get out of line. You can treat them just like you treat your brother. Just out of curiosity, how do you punish your brother when he is naughty?”

“Oh, I just spank his bottom,” Ollie said casually. “It’s very effective on boys when they get too big for their britches, and it’s over soon so you can move on. Benji has his paddle in his room. Please, Benji, bring it here so that Mr. Paterson can see it.”

I was blushing by then, and I didn’t want them to see my paddle, but when Ollie gives an order you obey. So I ran to my bedroom and came back with my paddle, the one that says “Benjamin’s Paddle”.

I handed it to Ollie and she passed it to Mr. Paterson for him to inspect. He seemed approving and kind of amused.

“I see you know how to make boys mind you,” he told Ollie. “I have got very good references of you, so I’m not worried. This paddle doesn’t look like much, though, are you sure it can do the job?”

I was incredulous that he would doubt that paddle’s effectiveness. Let me tell you, he wouldn’t be saying that if he had ever felt it on his bottom.

“Oh, yes sir,” Ollie said. “It’s thin and light, so it doesn’t cause bruises, but I assure you that it’s very effective when applied to a boy’s bare bottom. Isn’t that right, Benji?”

I blushed and became tongue-tied.

“Don’t be shy,” she told me gently. “Mr. Paterson has two sons. He is no stranger to the concept of boys being spanked when they are naughty.”

“I’m certainly not,” Mr. Paterson laughed.

“See?” Ollie said. “Now look at Mr. Paterson’s eyes instead of at your feet and answer the question. Is your paddle effective or not?”

I looked up, blushing, and said “Yes, sir, it is really effective.”

“I see,” he said. “Do you need it often?”

I blushed even more and looked at Ollie for help.

“He’s a good boy,” she said. “But like all boys he sometimes forgets the rules and misbehaves and, when he does, he gets his bottom bared and a good dose of the paddle changes his attitude right away.”

Mr. Paterson laughed again. “Well,” he said, “I don’t have the slightest doubt that you can take charge of this group of boys. Thank you very much, Olivia. I have already transferred your fee to your mom’s bank account, like we agreed. Don’t hesitate to phone me if you need to. And you boys, be good and mind Olivia. I’m sure you don’t want to get acquainted with that little paddle.”

So he kissed his sons and left.

“Well, boys,” Ollie said. “I know it’s Friday and you guys don’t want to hear about school again, but in this house we try to do our homework on Friday if possible, so that we can have the weekend free. So, as you are now an honorary part of our family, that’s what you are going to do while you are here. Take your school things, please. We have two desks in the study, and they’ll do for all of us.”

Nolan and I went to obey, but Tyler frowned and crossed his arms. “Look, I know my dad left you in charge,” he said, “but I’m 13 and I don’t need no babysitter. You can babysit them if you want.”

If he knew Ollie like I do, he would have cowered at the expression on her face, half smiling and half pissed off.

“Oh, you think you don’t need a babysitter, do you?” she asked. Her voice was apparently pleasant but warning bells were going on in my head. If I were Tyler, I would be running to do what Ollie said.

“No, I don’t,” Tyler said proudly.

“Well, you dad has trusted me to look after you and be your babysitter, and I’m not going to betray his trust... Now, I want to get along with you boys, but make no mistake, I’m the one in charge here. When I tell you boys to do something, I expect you to do it right away and without any attitude. So, for the first and last time, I will repeat my order. Get ready to do your homework.”

Tyler seemed taken aback at Ollie’s dominant attitude and looked towards his school bag, but then he had second thoughts and crossed his arms again.

“You’re just a little kid yourself. You won’t be bossing me around as if...”

We never found out what Tyler was trying to say. Ollie, with a thunderous expression, took two steps forward and grabbed his ear. My sister is surprisingly strong, from the swimming she does, and she had taken him completely by surprise. Besides, I don’t think Tyler thought she would actually do something like this.

“Ow! Oww! You’re hurting me!” Tyler said in a high-pitched voice. His hands went to his ear, trying to rescue it from Ollie’s grip, but she was not letting go.

“I (SPANK) don’t (SPANK) take (SPANK) any (SPANK) disobedience (SPANK) from (SPANK) boys (SPANK). Whenever (SPANK) I (SPANK) tell (SPANK) you (SPANK) to do (SPANK) something (SPANK), you (SPANK) do it (SPANK). Right! (SPANK) Away! (SPANK)”

Still keeping hold of his ear, Ollie punctuated each of her words with a hard spank on the seat of Tyler’s shorts. Some of the spanks fell just below the hem of his shorts, and you could see the red handprints on his thighs. As I said, she is surprisingly strong. She beats me easily at arm wrestling, and I’m sure she would have beaten Tyler easily too.

Finally, she let go and he stood there holding his burning ear with one hand and the back of his shorts with the other. He was sobbing, looking completely cowed. Even I was cowed, and I was not the victim of this treatment. Then again, I had never defied Ollie as openly as that, not even at the beginning when she first took charge of me.

Ollie took Tyler’s arm and pulled him towards the sofa. She sat down and started unfastening his shorts, while he cried.

“Little boys who try to disobey me get a spanking,” she informed him. “Bare bottom.”

Then, as she was pulling his shorts down, she looked at me and said, “Please, Benji, bring me your paddle.”

For the second time that day, I ran to get my paddle from my bedroom. Fortunately, none of those times was it meant to be used on me!

When I came back Ollie had Tyler’s shorts and undies around his ankles. He tried to cover himself, but I could have told him that Ollie had little patience for things like that.

She swatted his bare bottom once and said, “Hands away from your peenie, little man. You have nothing I haven’t seen before.”

I couldn’t help looking. His peenie was bigger than mine, but just as hairless.

Ollie then pulled him over her knees and took the paddle I was handing her.

“This spanking is so that you don’t have any doubts on who is in charge here,” she told Tyler. “You are just a boy, and you obey whoever is in charge of you. It doesn’t matter if it’s a grownup or a girl, and it doesn’t matter how old the girl is. If she is in charge and she gives you an order, you obey her without any nonsense.”

Saying that, she started paddling his bare bottom.

If he had tried to be seen as a big boy, he sure wasn’t trying now. He was bawling and carrying on, but she didn’t stop until all his bottom was red.

She finally stopped and let him go. After managing to get up, he just stood there crying and rubbing his bottom while hopping from one foot to the other.

“That’s enough, Tyler,” Ollie said, although in a much kinder tone. “Let go of your bottom. You are supposed to feel the sting, you know.”

Tyler obeyed and he did not even bother to try to cover his peenie. Good thing too, because Ollie wouldn’t have allowed that either.

“Come here,” Ollie said. She hugged Tyler. I think she caught him by surprise, because he stiffened. I mean, his body stiffened. Like, his whole body, not his... well, you know. (I don’t think anyone would be thinking about that after one of Ollie’s paddlings).

But then she spoke to him in a gentle tone of voice, and he relaxed in her arms and buried his face in her shoulder.

“That’s OK. It’s all over now. I know it hurts, but you know you are supposed to mind me. When I tell you to do something, you do it, OK?”

He nodded into her shoulder.

“Good boy,” she said.

I looked at Nolan, and he was open-mouthed, looking at how red his big brother’s bottom was.

“OK, you boys get started with homework,” Ollie told Nolan and me. “Benji will show you where the study is, Nolan. I’ll help Tyler wash his face and we’ll join you in a moment.

I took Nolan to the study and we sat down by one of the desks and got started with our homework. A few minutes later, Tyler and Ollie came in. Ollie was no longer crying, but he was completely naked. He had clearly washed his face, but his bottom was just as red as a few minutes ago.

“I have decided that Tyler will be naked until his bathtime,” Ollie said mildly. “I’m not dressing him just to undress him again then. You sit down here, Tyler, and start your homework. I’ll be doing mine, but I’ll help you if there’s anything you don’t know how to do.”

All the defiance seemed to be spanked out of Tyler, because he just nodded and said “OK” in a small voice.

He sat down on one of the chairs, wincing as his sore bare bottom came in contact with the hard wood. He shifted uncomfortably.

I felt sorry for him, and decided to offer some comfort.

“It’s OK,” I said, “I know what it feels like, but soon it won’t sting as much.”

He looked at me. “Thanks,” he said with a small smile.

We did our homework without much incidence, and Ollie reviewed our work and was OK with it.

Then we showed the Paterson boys the guest bedroom where they would sleep.

“Tyler, go bring your bags, please,” Ollie said. “Your brother’s too.”

“Yeah, right away,” he said, hurrying to obey.

His attitude was completely different. Naked as he was, he did not seem resentful. On the contrary, he seemed to crave a word of approval from my sister, and looked at her with doe eyes. Sometimes he looked down at his naked body and blushed, but he no longer tried to cover himself, because she had told her not to.

Ollie said we could watch a bit of TV, and we did.

Tyler, still naked, sat by his side on the sofa, and at some point he leaned on Ollie and put his head on her shoulder.

“Good boy,” she said, patting his head and putting her arm around him, and he seemed to soak the affection.

When the episode we were watching ended, Ollie said that it was time to turn off the TV, and none of us argued. None of us had any doubts about who was in charge. Tyler was acting all submissive and clingy, and he wasn’t the only one. Nolan, his little brother, was acting kind of like that too. I was even feeling a bit jealous. Ollie was treating both of them with affection, as if reassuring them that if they were good boys they were not in trouble with her.

“Well, I guess Tyler is ready for his both, so let’s get the rest of you ready,” Ollie said. “Come here, Nolan.”

Nolan obeyed and Ollie got him undressed, until he was as completely naked as his brother. Nolan let her do, without the slightest hint of rebellion.

Then it was my turn, and Ollie got me undressed too. We were a sight, three naked boys, one of them red-bottomed, and a girl, shorter than two of the boys but completely dressed and obviously in charge.

“Benji, take them to the bathroom. I’ll leave these clothes in your rooms and I’ll be there in a moment to give you your baths.”

We did as she said, and I started filling the tub.

“Is she always like that?” Tyler asked me.

“Yeah, she really doesn’t like it when you disobey her,” I said. “But she can be fun too, as long as you remember she is in charge.”

“She paddles really hard,” he said, rubbing his bottom tentatively.

“Yeah. She is in the swimming team, and she’s really strong. You wouldn’t guess it just by looking at her, but she is. You should ask her to arm-wrestle you if you don’t believe it.”

“Oh, I believe it!” Tyler assured me.

Then Ollie was back, carrying our pajamas. She got us three into the big tub, which was just big enough for us three boys. She made us sit in the warm water and got our heads and the rest of our bodies wet. Then she put shampoo on our hair. (It’s nice when she is massaging your head). After that she made us stand one by one to wash us.

We were all sitting looking in the same direction, but I was at the back, so I could see while she washed Nolan and Tyler. I could see they were embarrassed when she washed their peenies, and when she washes your bottom it’s surprising the first time, because she is very thorough and she even inserts the tip of her finger into your hole to wash it well. They both got on tiptoes when she did that, but none of them offered any resistance or backtalk. They just did as she said and let her do.

Finally, she got us out of the tube, dried us and dressed us in our pajamas.

“Good boys,” she said. “You three have been good as gold.”

Afterwards the weekend went well. We did several fun things and had a good time. The three of us were completely obedient and did everything Ollie said, but it was not like when you are obedient out of fear. I think both Tyler and Nolan had realized quickly what took me some time to realize. That Ollie, although she is a kid too, is on a completely different level from us. And even though it is embarrassing when she undresses you, it’s a bit like an adult doing it. I still can’t help feeling that embarrassed when she does, but deep down I know I shouldn’t. I mean, it would be worse if she was an equal, so once you realize she really isn’t, it gets a bit easier. Just a bit.

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From: Zac (Zachary Randy Saunders, age 13)

But she still kept bathing you guys all through the weekend?

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From: Benji (Benjamin Grady O'Connor, age 13)

Sigh. Yep, she always does. Says she doesn’t trust boys to bathe properly. If she’s looking after boys, she is bathing them, cause that’s part of taking care of them.

So just as that first evening, she bathed the three of us again on Saturday and on Sunday, just before Tyler and Nolan’s dad came back to get them. She said she wanted to return them to their dad already bathed, that it was part of her services as babysitter.

It’s funny, sometimes she was playing with us and enjoying it as a kid, not like an adult who plays with you to humor you but is not actually into it, and sometimes it’s like she becomes a grownup.

It’s so cool getting paid to babysit, though. I wish I could do it myself. She got a paid A LOT for the three days of looking after Tyler and Nolan! She told me she was happy to get babysitting money again. She used to babysit more before I was adopted, but she had to stop when I was, because she had to look after me. Mom is trying to get a different shift, but it’s not easy, so often mom can’t be here in the evening and Ollie has to look after me. She said she couldn’t leave me alone and go babysit some kid, but there was no reason she couldn’t babysit kids at our home, like she had with Tyler and Nolan.

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From: Brandon (Brandon Stanley Miller, age 13)

How did Tyler and Nolan take Ollie being in charge for the rest of the weekend? Was there any more trouble?

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From: Benji (Benjamin Grady O'Connor, age 13)

Oh, no, no more trouble. It went quite well. After that spanking Tyler got, we all knew who was in charge. Well, Tyler and Nolan did. I knew it from before, of course. And one those two knew, we all obeyed her whenever she gave an order, and we didn’t give her any problem, so it was all nice and friendly.

I liked Tyler and Nolan. I like being with Ollie but, as I said, with her you don't feel like she’s really your equal. She’s on a level above you. So it was kind of fun having other kids to play with that are actually my equals. I mean, we were all in the same boat. Being bossed around by a younger girl seems less embarrassing if you are sharing it with other boys. Being more, it feels like it’s a natural thing, and not that it’s because you are a failure somehow.

Of course, when I say they were my equals, I mean Tyler is. Nolan is kind of a little boy. I mean, he is only 11, although he is still fun to play with. Made me wish I had a little brother. At least I could boss someone around for a change! ;-)

But it’s kind of crazy to think Nolan is actually a couple of months older than Ollie. I mean, he acts like a little boy. The contrast between him and Ollie couldn’t be greater. He didn’t even seem that embarrassed when Ollie undressed him and saw him naked. I mean, having a girl your age see you naked, to say nothing of bathing you, is supposed to be embarrassing, right? But since her behavior is so much more grownup and confident, it’s difficult to think of her as being the same age as Nolan. It’s kind of the same for me, it’s difficult to think of Ollie as my little sister, because she can act so much more grownup, and the difference between Nolan and her is even bigger.

When Ollie was bathing Nolan. I mean, washing his peenie and his bottom and all, and talking to him like one talks to a little kid, sometimes teasing him gently, or tickling him... Nolan just looked like such a little kid, naked like that. He’s as tall as Ollie, but Ollie doesn’t look like a little kid. It’s not just that she was clothed, but the whole way she acted. I wonder if Olie would look like such a little kid if she were naked. Of course, I don’t think I’ll ever knew. Ollie may see me naked every day, but I have never seen her naked, and I don’t think I’ll ever do.

It’s funny, because Nolan seemed to be in awe of Ollie all weekend, following her around like a little puppy and doing everything she said, even when it was not an order and we were all playing. Tyler was a bit like that too, particularly the first day, after Ollie spanked him. I think it’s because Ollie has force of personality like that, and they were also adjusting to thinking of her as an authority figure.

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From: Zac (Zachary Randy Saunders, age 13)

It’s kind of weird. I wonder how Ollie must feel, having so much power over a bunch of boys.

Can you imagine having so much power over a bunch of girls? Girls your age or even older? Being able to boss them around, and undress them and give them baths or spankings?

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From: Benji (Benjamin Grady O'Connor, age 13)

Ha ha! I would be looking at them naked all day!

But Ollie is not like that. She’s like a grownup. It’s like for her it’s not important seeing a naked boy. Like it’s perfectly normal and not worthy of special attention. Well, I guess for her it’s kind of normal. It’s not like us, who never get to see a naked girl. I mean, to her it’s important that we are obedient and respect her authority, but she doesn’t go out of her way to have us naked or spank us. She could have us naked all the time if she wanted, and there’s nothing we could do, but she doesn’t. And she never spanks or punishes unless we have done something to deserve it. If you behave, she doesn’t punish you at all, just because she can. As I said, she kind of acts like an adult.

(The End)