Billy Gets a Babysitter – Chapter Three

Billy Gets a Babysitter

BY EDGEALLTHETIME

Chapter 3

The very next day was the first day that billy was going to be babysitting. His Mommy told him to meet Tiffany at the bus area after school, and She would take him to Her house. Billy was full of dread during the day. He was scared of girls in general, and even more scared of Tiffany right now, but there was nothing he could do about it. He just hoped that She would be nice to him.

He went to the bus area after class, and immediately noticed Her. She was wearing a very short plaid, school girl skirt, with Her Bare legs showing and sandals showing her bare toes. Billy couldn’t help but notice. He felt a stirring in his peenie. It had been almost six weeks since Mommy had let him spurt, and he was constantly aroused. And the sight of this cute middle school hottie, wasn’t making it any easier.

“Hi billy, I am Tiffany”, she said.

“Oh hi”, billy said.

“Well, this is my bus, let’s get on. You sit beside me”, She ordered.

Once on the bus, some of Her friends were asking who the high schooler was. She told them that She was babysitting him.

“What!”, they said. “He is a senior in high school”, one of them exclaimed.

“I know”, Tiffany told them. “But his Mom said he is a very naughty boy when he is alone in the house”. And with that She made the cock jerking motion with Her right hand. All the girls laughed out loud. Billy wanted to disappear in to the bus seat.

Once inside the house, Tiffany’s Mom was there, and introduced Herself to Billy.

“Okay, off with all of your clothes please”, She said.

There was no choice now, he had to. Billy stripped off everything, and stood in front of Tiffany, the sixth grader, and Her Mommy, completely naked and hairless, with his peenie still slightly bruised.

“Wow, your toenails are painted red, like a girls”, said Tiffany.

“Um yeah, my Sisters like to do that”, billy explained.

“They are very cute billy”, Mrs. Adams said.

“I see your penis is still a bit sore”, Mrs. Adams said. “Tiffany, billy here, had to have a spanking on his penis after his Mommy caught him playing with Kathy’s panties without permission”, she told Tiffany.

“Oh, he likes panties. Can I show him mine Mommy”, she asked.

“Yes, but not until he has done his homework”, her Mother replied.

Billy’s penis erected at the thought of seeing Tiffany’s panties.

“It looks like billy wants to see your panties too”, Mrs. Adams laughed.

So, billy and Tiffany sat at the kitchen table and did their homework. Once billy said he was done, Tiffany checked to make sure he had completed it.

“Okay, let’s go to the family room for TV time”, She told him.

“You sit right there on the couch, I am gonna change in to my after school clothes”, Tiffany told him, as She went upstairs to Her room.

Billy found this new situation he was in, both scary and exciting. Being in someone else’s home, completely naked, being babysat by a 12 year old. It made him want to touch his penis, but he was not sure if it was allowed or not. His Mommy had told him that the rules in the Adam’s house, and his house were the same, so he decided that it would be okay, and started to slowly masturbate with thumb and forefinger.

He had closed his eyes and was thinking about Tiffany’s legs, when he heard Her say, “Oh, yeah, my Mom told me that you do that a lot, and that it is okay”.

He opened his eyes and was startled and excited to see that She had changed into a tshirt and panties. Well, he assumed panties, as the tshirt came to the top of Her thighs, and covered Her panties. He let out a little moan, and was slightly more vigorous with his stroking, at the sight of Her.

“Mommy also said, that you are not allowed to shoot your stuff out”, She said.

“I have seen my brothers shoot out, and also my dad’s”, she told him. “Too bad you aren’t allowed to shoot it, because they really love to”, she continued.

Billy’s head was reeling a bit. Did She just say her brother AND her dad?? What kind of family was this, he wondered. Was this house even more sexual than his own?

“I know you think that my brother, Tommy, is a jock, and I guess he is at school, but in this house my Mommy makes sure that the girls rule!”, She explained to him.

“Anyway, you will see someday, maybe”, She went on. She was now seated on the other end of the couch from him, with Her bare legs folded under Her. Billy was staring at her perfect little feet and legs and he then got a glimpse of her white panties. His thumb and forefinger were making short, quick, urgent strokes on his straining penis.

“Be careful, the last thing I need is you shooting your stuff all over the place on the first time I babysit you!”, Tiffany scolded him.

“Your Mommy is paying me nicely for this, and I want to make sure that when She picks you up, She will see your homework done, that you are nice and clean, and that you are very horny. So, let’s go upstairs and give you a bath”, She told him.

“Oh, okay, I like getting baths”, he said. “Sometimes my Sisters help me bath”, he told Her.

“That’s nice of Them, do They get in the tub with you?”, She asked.

“No, i have never seen my sisters bare naked”, he explained.

“Well, you certainly won’t be seeing me bare naked either, but I will sit on the edge of the tub and make sure you make yourself squeaky clean, and smooth. I have a shaver to give you. And you can play with your penis for a while after you have made yourself all clean and smooth. How does that sound”, She asked.

“It sounds wonderful Tiffany, thank You so much”, he said, while looking at Her toes again.

“Wow, you really do like my bare feet. That’s funny. Maybe someday if you are a good boy, you can paint my toenails for me. Would you like that?

“Oh yes Tiffany, very much so”, he said with a shaky voice.

She laughed.

Upstairs, Tiffany showed him around.

“That’s my Mom’s bedroom. The door has to be closed all the time”

“That’s Tommy’s room. Mom doesn’t let him have a door on his room, because you know what you guys get up to all the time”, She said with a smile. Tommy’s room was rather normal teenage boy room with some posters, a computer, some sport trophies.

“This is my room. I get to have a door, but I am not gonna show you my room, just yet”, She explained.

“And this is my dad’s room”. The room was not much bigger than a closet, and had nothing in it except a small, singled bed, small desk and computer. No door.

“Mom doesn’t let dad have a door either. He doesn’t have many privileges around the house. Mom is pretty strict with him”, Tiffany explained.

“Anyway, and this is the bathroom that Mom and I and Tommy use. You can have your bath in here. Let me run the bathwater”.

As the tub filled, Tiffany ordered him to hop in.

“Okay, clean yourself well, then run this razor over yourself, and then you can play with your penis for a while in the tub”, She instructed him.

Billy did as told, and felt so much like a kid being babysat. Naked in the tub, while this middle school hottie sat on the edge of the tub supervising his every move.

After cleaning and smoothing, She told him he could play with his penis for 15 minutes in the tub. He started using his thumb and forefinger and staring at Her legs. With that, Tiffany got up, and said she would be back in 15 minutes. She left him alone with this throbbing penis….

“Okay, out of the tub. I will dry you off”, She said.

Billy stood beside the tub, his little penis sticking straight up. But Tiffany did not touch his penis at all with the towel. She dried every other part, except that one. He was so hoping…against hope.

“Okay, clean the tub, hang the towels and come back downstairs”, She ordered him.

When he got back downstairs, his Mommy and Mrs. Adams were sitting in the living room, along with Tiffany.

“Was he a good boy Tiffany”, his Mommy asked.

“Yes he was, he did as told. I let him play with his penis for the last 15 minutes in the tub, I hope that’s okay”, Tiffany asked.

“No, that’s fine sweetie, he spends hours each day doing just that”.

“He really seems to like my bare feet a lot. He was staring at them all the time.”

“Yes, he has a very strong foot fetish, the poor thing. Barefeet make his peenie throb so bad, don’t they hun”, She asked billy.

“Yes Mommy, they do”, he replied.

“I am sure if you are a good boy, Tiffany will show you her bare feet a lot, won’t you Tiffany?”

“Oh yes I enjoy seeing his ‘peenie’ all stiff and sticking out that like that”, Tiffany answered.

“Well, I am glad the first day worked out so well. I think tomorrow, the girls are staying after school again, so can you please bring billy home with you again Tiffany”, billy’s Mommy asked.

“Yes of course”

“Oh, I don’t see Tommy or Mr. Adams here”, she said to Mrs. Adams.

“They will be here tomorrow afternoon. Tiffany and I can introduce billy to them. I am sure they will have fun together”.

All the girls laughed.

“Okay billy, get your clothes on, thank Miss Tiffany, we are going home now”.

“Thank you Miss Tiffany”, billy said, as he put his clothes on.

 

5 thoughts on “Billy Gets a Babysitter – Chapter Three

  1. Great Story! Please continue the series.

    This reminds me of a story I read on the internet – quite a few years ago – about a boy around the age of 17 and whose eccentric mother hired a new girl in his high school he had a crush on to ‘babysit’ him and make sure he isn’t naughty.
    In the story his last name was bates so in school he was often teased and called Master Bates due to his reputation as a chronic masturbator (which he always denied).
    As the story goes he met a cute girl over the summer and developed a big crush on her though always afraid to ask her out…instead he would just masturbate to thoughts of her. As it turned out, he saw her again on the first day back to school – but poor Master Bates’ fortune quickly turned when one of the High School jocks named Johnny De’ Marco saw him talking to her and insisted he introduce her to him which Bates did…regrettably for Bates Johnny used the opportunity to eliminate any chances of bates ever having a shot with her – as if he ever did anyways.
    Later that evening his Mother said she was going out and that she had lined up a new baby sitter for him – he protested of course, but to no avail. Then the door bell rang and he was stunned and his face turned deep red when guess who was standing at the door – yes his secret crush.
    Bates was further humiliated when he overheard his mother giving her the instructions about not letting Bates masturbate.
    She was kind about about the whole thing really and curious about his chronic masturbation…she said her little 13 year old brother was going through a similar phase but thought boys grew out of that sort of thing.
    Just then the doorbell rang and it was Johnny. Well Bates was mortified and embarrassed – being teased in school because of some rumor was one thing but this was another…
    Johnny did not hesitate to use the opportunity to try to further humiliate him but his crush intervened and stuck up for Bates…she put him to bed and told Bates how she was going to give Johnny a piece of her mind. For a moment Bates thought with johnny out of the picture he may still have a shot. That thought quickly faded as he heard giggling and laughter coming from down stairs. That turned into sounds of moaning and some grunts and he knew what was happening and what Johnny was doing to his crush. But the sounds were overwhelming and being the chronic masturbator that he was could not help but to yank his pajamas down and start playing with himself.

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