Babysitting Thomas and Barbara (ENM)

[Namb]

It starts slow but builds itself up.

The Assignment

Mrs. Mercer had concerns about attending the seminar. She would be gone for more than a week. The seminar was in the same city where her sister lived, and she decided to take the weekends on either side of the event for a visit.

She had never left her children alone for so long and did not have a reliable babysitter until one of the members in her women’s group told her about Hannah Wilson. “She’s by far the best babysitter I’ve ever had. The kids love her and there has been a change in how they treat each other. They used to fight all the time. Ever since Hannah’s been sitting them, they get along just fine.

Everyone who uses her says the same thing. She has a knack for getting snarling siblings to play nice with each other.

I’ll give you some numbers. You can call them yourself.

-=o=-

“This should be a fairly easy babysitting assignment,” Hannah Wilson thought, “Two kids: boy Thomas, and a girl Barbara. They’re older and should be well behaved. I hate bratty toddlers.

It’s also a week-long gig and a lot of cash.”

Thomas didn’t think so and expressed his opinion to his mother, “Mom, I’m 14 and I don’t need a babysitter.”

“Under normal circumstances, I’d agree, but I will be out of town for over a week That’s too much time for something bad to happen. Hannah is 16. She has a driver’s license. She can get either you or your sister to the urgent care if needs be. She can also get Barbara to her soccer practice that is if it ever stops raining and the field dries out enough.”

“I don’t like it.”

“You don’t have to like it; you just have to accept it. Besides, Hannah will be taking care of Barbara as well, this way you don’t have to. You won’t have to do the cooking, but I do expect the two of you to help Hannah clean up.”

Friday afternoon arrived and Hannah reported to the Mercer’s early. She was a responsible babysitter and considered punctuality important.

Mrs. Mercer gave her final instructions including emergency numbers and emergency cash. “I’ll have my phone with me all the time. It will be off during the seminars, but I will have it on vibrate, so you should be able to reach me 24/7.”

“Have a good time at the conference and have a safe trip.”

Mrs. Mercer left and Hannah turned to the two kids. “So what do you guys want to do this evening?"

Barbara piped up, “There’s this movie I want to watch, can we?”

“How about you, Tom, do you want to watch the movie, too?”

“No, it’s a little girl movie. I watched about 5 minutes of it the first time she watched it; it’s definitely not my thing. I’ll probably play games on my computer since mom won’t let me go out while she’s gone.”

“Thanks for understanding. Your mom gave me a lot of instructions on limits. It’s not my idea to keep you cooped up, but it does make some sense. I’m glad you’re not giving me a hard time on this. I don’t have a choice.

Your mom also asked me to make sure you studied for your history test next week.”

The boy frowned, but said nothing and went up to his room.

“Come on, Barbara, you can help me get things set up for dinner.” The two girls retired to the kitchen.

[Namb]

A Conversation with Barbara

Hannah had an agenda. Ever since she was a little girl, she detested the way boys got away with things and how they treated girls. She was a confirmed female supremist and believed that girls should rule boys. She used her position as a babysitter to make this happen when she could. The Mercers were new to her, and she had to plan carefully.

As the girls were working in the kitchen Hannah said, “So Barbara, have you ever considered being a babysitter?”

“Sure, I can’t wait until I get older.”

“How old are you now?”

“I’m 11.”

“Well, then you’re almost there. I started when I was 12.”

“Really?”

“Well, my first assignments were small. Taking care of the kids next door when they got home from school until their mother got home. But I worked my way up from there.

Would you like to help me babysit this week?”

“Yes, but who are we going to babysit? I can’t babysit myself and Tom is older than me.”

“I know some girls who babysit boys older than them.”

“Really?”

“It’s not usual but these boys have ‘special needs.’” Hannah did not go into what those “special needs” were.

“Wow, I never thought of that.”

“It’s true, girls mature much faster than boys. I bet you noticed part of that already. I bet you and some of the other girls in your class are taller than some of the boys.”

Barbara nodded.

“Boys catch up eventually, but for the next couple of years, you girls will be ahead of boys your own age.”

“Just follow on my heels and I’ll show you some tricks.

I think you’ll like being a babysitter. One of the fun things I like to do is give little boys their baths.

Have you ever seen a boy naked? Do you know what boy’s look like?”

“Well not for real. There are drawings in a book my mom gave me and then a friend of mine has a boy-doll and it has a penis, but we haven’t played with it for a while. Some of my friends have baby brothers and they told me they’ve seen them.”

“I’m impressed that you called it a penis.”

“Mom’s pretty good about that. She keeps me informed. I like it when I can tell other girls it’s a penis when they’re calling it a pee-pee or wiener. It makes me feel more grown-up.”

“That’s the way it should be. So, I don’t even have to ask. It’s obvious that you’ve never seen your brother.”

“No, I haven’t. Maybe if he were younger it would be different.”

“Age really doesn’t have anything to do with it. Girls see their brothers naked all the time, even their older brothers.”

“Really?”

“Maybe your brother is just too modest. I’ve seen my brother naked as late as last week and he’s 18.”

“Wow.”

“We’ll have to see what we can do to get you caught up with other girls your age.”

“One down and another to go,” Hannah thought. “I got her thinking about boys and penises and girls seeing them and it being natural for sisters to see their brothers naked and that maybe she’s missing out.”

Outwardly she said “I’m going to the bedroom where I’ll be staying and get unpacked. I’ll be right back out.”

Hannah did the promised unpacking; she also changed her clothes. She took off the bulky shirt and jeans and replaced them with a very revealing top and the shortest shorts possible.

When she came back in the kitchen, she said to Barbara “Let’s go check in on your brother.”

The girls went upstairs and Hannah knocked on Tom’s door.

“Come in,” came the muffled reply.

Tom was sitting there with his computer paused.

“How’s it going?” Hannah asked.

Hannah had to stifle a laugh when she saw his reaction to her new outfit.

Tom nearly choked out his response, “Boring. I must have played this game a hundred times, I need to get some new ones.”

“I’m sorry to hear that, maybe I can help. I have a friend who showed me some ‘cracks.’ Maybe I can get you some new games.”

“Really? You’d do that?”

“Maybe after dinner. Why don’t you start studying for that history test. If you can get it out of the way, then we’ll see about the games, and you can enjoy the rest of the week.”

Why don’t you read us some of the lesson and Barbara and I can question you on it and that way you’ll be sure to ace the test?”

Tom opened his book and started reading. It became immediately apparent that he was having difficulty with the words.

After several minutes, Hannah said, “Tom, stop reading and give me the book.

You can’t read, can you?”

Tom bowed his head and shook it. “It’s so hard. I don’t know. I look at the words, but they don’t make sense unless I sound them out.”

Hannah took his hand, “It’s OK we’ll help you out.

Having any kind of a problem is nothing to be ashamed of as long as you are willing to get help and work at it. I’ll talk to your mom about this when she gets back. There’s a program in the school that can help you. Reading is important, whatever it is you like to do, there’s a book written about it.

We can find some books on topics that you like, and you’ll soon discover that you want to read. The more you read, the better you’ll get at doing it.

For this weekend, I will read your lesson to you.

Barbara, are you willing to help?”

The girl nodded excitedly.

“It’s going to take a while for his reading skills to get up to par. Are you willing to read his lessons to him every night until then?”

“I’d love to and then when I get to his grade, I’ll already know everything I have to know.”

“Maybe they’ll skip you a grade then and you’ll move up to a class of boys who are closer to you in maturity.”

The two girls took turns reading the lesson to Tom who picked up on it quickly.

“Man, it makes a lot more sense when I don’t have to struggle with the words. You girls are fantastic.

Thank you, Hannah. You too, sis!”

“Barbara, could you do me a favor. Could you go down to the kitchen and preheat the oven to 350. I’ve had my girl talk with you earlier. I’d like to talk to your brother privately to get to know him better.”

[Jeepman89]

Thrilled to see another story, Lamb. This looks quite promising.

[Lola]

Smart move the change of outfit! I like Hannah. Can't wait to read more

[Namb]

A Conversation with Tom

After the girl left, Hannah said, “That’s quite a boner you got in your pants, boy!”

Tom blushed.

“I noticed that you haven’t taken your eyes off my boobs since I got in here.”

“I’m sorry,” he mumbled.

“It’s OK, I know all about boys. I have an older brother, Jason.

I bet if I spent 5 minutes searching your room, I’d find a dirty magazine somewhere. How about it, should I check under the mattress?”

“No, don’t do that.”

“I thought so. Under the mattress is the first place a mom will check, if she suspects that her son is jerking off. You do jerk off, don’t you?”

“I, ah, um ...”

“I’ll take that as a yes. Don’t worry about it, all boys do it.”

“You know about it?”

“As I said, I have an older brother. I caught him doing it once. He tried to cover up, but I asked if he would let me watch and I did.”

“Really?”

“Yes, in fact it works out well for both of us. I like watching him do it and he doesn’t have to hide it from me anymore. All we have to do is wait for our parents to be out and that happens a lot.”

Hannah did not tell Tom that her brother’s “cooperation” wasn’t exactly voluntary. She had secretly taken some pictures of him doing it and was using them to blackmail him into submission not only for her, but for her female cousins, her friends and their sisters. His “private parts” were not so private to at least a score of girls.

Hannah went on, “So we can be on the same side on this issue.

I know how horny a boy your age can be. According to what my brother tells me, a boner like that can be very uncomfortable.

So, I can either we keep things as they are and you don’t get to do anything with it. Or, as an incentive, I can remove the controls on your computer to allow you access to some very interesting sites and you jerk off for me and your sister.”

“What? I can’t do it with Barbara watching. She’s too young.”

“I was only 10 when I first saw my brother do it. She’s mature. She can handle it.”

“Oh shit!”

“Think about it. How many times in the past have you wanted to beat your meat but couldn’t because Barbara was around?

She can even help and do it for you.”

“Have her touch me? No way.”

“You can deny her, but I would advise you let her do it. I have a lot of friends who give their boyfriends hand jobs, and all the boys claim that it feels better when a girl does them than when they do it themselves.”

What Hannah did not tell Tom was that these hand jobs were usually conducted at CFNM parties with multiple girls and boys in attendance.

“I don’t know.”

“Let me show you how good I can be on this.

First of all, don’t put your magazines under the mattress. As I said, that’s the first place moms look. Make a big pouch out of cardboard and tape and tape it to the back of the headboard.”

Hannah got up and walked across the room. She picked up the trash can. “Aha, that’s a lot of tissue you got there. It’s all wadded up and caked. Either you have a very runny nose or that’s something else. Smart moms know to look for this too!

Use paper towels, they absorb more so you’ll only need one sheet. Then dispose of it in the kitchen trash. If you use tissues, flush them down the toilet. In fact, if you kneel in front of the toilet when you do it, you can ejaculate into it and flush away the evidence all in one act.”

“These are good ideas. How do you know about them and why are you telling me?

Wait, let me guess, you’ve seen your older brother do all these things.”

“That’s right. I’m just passing on the benefits of my brother’s experience besides, I want you to trust me.”

“I can’t believe that I’m talking to a girl about this stuff. I don’t even talk to my friends about it.”

“I’m not just a girl. I’m your babysitter and I am older than you. I know a lot about sex and if you want to learn it, just go along with what I say.”

“OK.”

Hannah figured that she had planted that seed at the appropriate depth and went onto something new, “Now let me at that computer of yours. I guess your mom has some limits put on there that keeps you from getting to all those web sites your friends are telling you about.”

Hannah sat at the computer. She shut it down and plugged a USB stick in it. When she turned it back on, the screen was entirely different. She typed in a couple of commands.

“There,” she said, “All I need is the WIFI password that your mother gave me and … like that, you’re in.” She launched a browser and went to a URL and up came a picture of a woman performing oral sex on a man.

“What did you do to my computer. My games are on there. My homework is there. I have pictures on there,” he said with a panicked voice.

“Don’t worry, shut down the computer, take the stick out and start up and everything will be as it was.” She demonstrated by doing what she just told him.

“Now everything is back to normal,” she said pocketing the drive.

“What kind of magic is on that stick?”

“It’s just something my geek friend taught me to do. She teaches me technology and I teach her about boys.”

“Where can I get one?”

“Do as I say, and I’ll give you one. I can always make more. In fact, they are so easy to make, I can do it tomorrow morning. All I need is a spare thumb drive.”

“I got a 6-pack of them for my birthday. I still have three with nothing on them.”

“Good, because the process wipes out whatever is on the stick, but the good thing is that you can save whatever you download directly on the stick so your computer remains ‘clean’ in case someone else wants to inspect it.”

From downstairs she heard Barbara call, “The oven’s ready!”

“We’ll be right down,” she replied.

To Tom, she said, “Think about what we just talked about.”

[Jeepman89]

I love how she's gaining the confidence of Thomas and Barbara. Such a good babysitter.

[NudeBaG]

This is off to a perfect start

[nebnyc]

Great new story! Hannah’s 18 yr old brother & what she’s doing with him sounds like an equally intriguing follow up or prequel.

[Namb]

Barbara’s First Penis

Dinner was a casserole-like affair. It went from refrigerator to oven to table in about 30 minutes. Barbara helped her with the salad.

“You’re really nice for a babysitter. Can I ask you a question?”

“Sure.”

“It’s kind of about what we talked about before.”

“You can ask me anything, Barbara. I won’t tell anyone unless you want me to.”

“Tommy had a lump in his pants. Was that his … penis?”

“Yes Barbara, it was.”

“Why was it poking up. It doesn’t do that all the time. Sometimes it’s there and sometimes, it’s not.”

“Tom was having an erection. Do you know what that is?”

The girl shook her head, “no.”

“When a boy gets sexually excited, blood fills his penis and makes it swell, it gets bigger and harder.”

“Why does he make it do that?”

“He doesn’t really have control over it. When boys see pretty girls, for example, they will get hard down there. It really has to do more with us girls than the boy himself. All we have to do is be girls and all they have to do is look at us.”

“Oh.”

“Look, I think I can convince Tom to show us his penis. Would you like to see that?”

Barbara was bouncing up and down with excitement, “Of course I would! How are you going to get him to do it?”

“Just leave that to me. Let’s not talk about this anymore until after dinner. OK?”

“OK!”

Hannah noted that both kids seemed agitated at dinner. Tom just pushed his food around with his fork and Barbara was taking the smallest of bites

Tom was obviously mulling over Hannah’s proposal in his mind. He had friends who bragged about surfing the web to some exciting stuff and now all that would be within his reach. It would mean exposing himself to his kid sister. Would it be worth the price?

Barbara was anticipating the excitement of seeing her older brother’s penis. She had friends, too, who bragged about seeing big boy penises, but none were as old as her brother’s. She fantasized about how popular she would be with the girls in her class if she could show him off to them.

The kids went through the motions of helping Hannah clean up. Hannah knew that she had them when they both turned down dessert.

“OK, kids,” Hannah said, “There is something I want to talk to the both of you about.”

Each child was prepared for an after-dinner address, but neither of them knew that Hannah had pushed them towards the same place.

They sat down in the living room and Hannah began. “Tom, have you decided what you want to do for the rest of the weekend?” she asked. In any other kind of context, it was an innocent question. However, with all the thoughts Hannah put in his mind, it had only a sexual kind of context.

“Does Barbara have to be there?”

“Yes, she does. Think about it, what would she think if we both went into your room and locked the door? What would she tell your mom?”

Barbara was about to say something, but Hannah cut her off, “Wait Barbara, your turn will come.”

Tom asked, “But I get the stick after this is over?”

“The fish is following the bait.” Hannah thought.

“Will it be just this one time?”

“He’s opening his mouth.” Aloud she said, “For just the rest of the week, if that’s what you want, but I think you’re going to want to do this a lot once you feel how good it will be.”

“And I get the stick in the end?”

“HOOKED HIM!”

“Yes you do.”

“So how do we do this?” he asked.

“How about we take it slow.”

Turning to the young girl, she said, “Hannah, this is a big step. A girl only has one ‘first penis’ in her lifetime. Do you still want to see your brother’s penis?”

“You talked to her about this?” Tom asked, shocked.

“Of course, I did. She’s a girl and girls share secrets.”

“I repeat. Hannah, do you want to see Tom’s penis?”

“Yes,” she added meekly.

“Tom, stand up, face your sister and take it out like you are going to make pee.”

Tom had to make up his mind. He knew that he could back out, but the embarrassment factor had already come into play. His sister knew that he was at least thinking about it and who knows what else Hannah told her.

Nonetheless, exposing himself to his sister was an irreversible step. There will be a time in his life before he showed her and another time in his life after he showed her. This was the defining moment.

It would also be a first time for him, too. If he was to be his sister’s “first penis,” then she would be the first girl to see his penis since he started puberty. There was something about being any girl’s “first penis” that excited him.

The boy’s face was red with rushing blood as he slowly lowered the zipper on his pants. “I can’t believe I am doing this,” he thought, but in defiance of his brain, his fingers completed the act of exposing his penis to the two girls.

Barbara gave a gasp then giggled into a cupped hand. Hannah just smiled. She had probably seen naked boys hundreds of times, but getting boys naked was always the most fun part and getting a boy naked for the first time was always a special event.

Getting a boy naked in the presence of another girl was a bonus, especially if the other girl is a kid sister. It made her feel good that the boy would have a full-time female companion to help him with his training. Girls need to stick together on things like this.

The three of them remained silent, the boy with hands at his side and his penis dangling out of the hole in his pants, Hannah standing at his side and Barbara leaning so far forward that she was almost off her seat. Sitting as she was put her brother’s penis at eye level, and she had the best view in the room.

Hannah broke the silence. She put a hand on Tom’s shoulder to reassure him and said, “Barbara, why don’t you reach out and touch it.”

In a slow and deliberate move, Barbara extended her hand and first put just a finger tip to the head of his organ. This bit of stimulation caused it to twitch and she withdrew it as if she had touched a hot iron, but giggling instead of crying in pain.

“Come on, girl. You can do better than that!” Hannah coached her. Hannah reached down and wrapped her hand around the shaft and gave it a squeeze. Tom let out a sigh.

“Be bold. Hold it like I just did. These things may look delicate but they are relatively tough you can ‘girl handle’ them. His balls are another thing. You have to be careful with them.”

Barbara spent several minutes exploring the boy’s organ.

“What’s happening?” she exclaimed. “It’s getting bigger.”

“He’s having an erection like we talked about. It means he likes what you’re doing to him. Isn’t that right, Tom?”

Tom was startled out of his trance, “It feels funny. I’ve never had anyone else touch me there. It doesn’t feel like that when I touch it.”

“I told you that girls have a special touch. Let your sister continue.”

Barbara played with her brother’s penis until it leaked.

“What’s that? It doesn’t look like pee.”

“It’s called pre-cum, Barbara. When a boy gets excited, his penis gets hard and if it stays hard long enough then it starts leaking out fluid. Go ahead, feel it. It won’t hurt you.”

Barbara stuck her finger out and wiped the drop off Tom’s pee hole. She giggled again when his penis twitched in response to her touch. She rubbed it between her fingers. “It’s slippery, but it’s also sticky.”

She put her finger to her nose and sniffed, “It doesn't smell like pee.”

“I dare you to taste it.”

“Oh, yuck! He makes pee there.”

“Don’t be such a baby. Here, I’ll do it.” Hannah took hold of the boy’s penis, gave the head a squeeze and milked out the next drop of pre-cum. She swiped the drop with her finger and slowly put it in her mouth and sucked on it seductively.

Barbara followed her example reluctantly. “It tastes a bit salty.”

“OK, I think we done enough for down here. Tom, I want you to go upstairs to your room and take off your clothes – all of them. Barbara and I will be up in a couple of minutes.”

“Do I have to? You girls have already seen all the good stuff.”

“No we haven’t there’s still the matter of seeing the rest of your body. Your sister has never seen an adult – well, almost adult male before. It’s important for her to learn about this.

And besides, if we’ve seen ‘the good stuff’ then what’s the sense of hiding the rest?”

“I don’t know, it just seems funny to have no clothes on at all.”

“Do you feel funny when you go to the pool and have a bathing suit on?”

“No.”

“Well, this is just the same except without the bathing suit. Now stop arguing and get upstairs and you better be naked when we get there.” She said this with such severity that Tom did not want to consider the consequences if he disobeyed her.

[Jeepman89]

Loving this story.