Chronicles of a Neighbourhood Babysitter Chapter 4

Chronicles of a Neighbourhood Babysitter Chapter 4
By Steam Train

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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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Chapter: 4 MATHEW, MARK, LUKE & JOHN.

Over the next two years Jennifer continued to baby sit for the Millers as well as building up a wide client base. The Millers were never frequent users of her services but they did manage to book Jennifer two or three times a year.

Chris never really got over the humiliation and embarrassment of being naked in front of Jennifer, no matter how many times she exposed him naked before her in the privacy of his house.

Over the next years Jennifer had even brought some of her friends with her as Mr and Mrs Miller had suggested on her very first visit, so as to assist in ensuring that Chris lost his excess modesty.

Her close friends were very excited at the opportunity and word spread amongst her peers that she had access to naked boys outside the NEWDD scheme. Jennifer was no fool and she quickly discovered she could handsomely enrich her profits from the babysitting by charging an attendance fee for girls who wished to attend one of her bookings.

If they could not pay cash, then as Jennifer had learnt first hand, there were other ways to pay!

During her first two years of being the neighbourhood babysitter most of her charges were young, aged from 5 or 6 years of age up to ten.

A typical charge of this type for Jennifer was Mathew Leahy. The 2nd Grader was 7 years of age and Jennifer regularly baby sat for his mother who worked night shifts occasionally. There was no sign of a father in the Leahy household.

On occasions Jennifer invited friends over to baby-sit with her.

One of the more memorable nights with Mathew was an occasion when Jennifer was thirteen years old and had invited two friends of one of her closest friends to accompany her. Both Angela and Kylie had willingly paid a small amount of their pocket money each to Jennifer to be allowed the privilege. If the boy had been older then Jennifer could have demanded much more money.

It always amazed Jennifer why girls would want to pay to have access to boys when the NEWDD programme allowed them to see boys totally naked at school and in the street. She decided that it was the private nature of the babysitting that made the difference. As a babysitter they might get the chance to not just make a reasonable request but actually wash and possibly disciple the boy as well as just inspect his naked body.

As soon as Jennifer had finished serving dinner for Mathew this night and Mathew had eaten all that was placed before him Jennifer brokered the news about Angela and Kylie.

"Mathew, these two friends of mine, Kylie and Angela are going to give you your bath tonight, so come over here to me and I will undress you so you are ready for my friends."

"I don't want to take my clothes off with these girls watching" Mathew protested.

"Don't be silly Mathew these girls have seen plenty of naked boys before, and you have nothing to hide that is different" Jennifer replied.

Reluctantly Mathew approached Jennifer and stood with his arms extended above his head as she pulled his shirt off. Then she sat him down and removed his shoes and socks. Then standing him back up she reached for the snap on his shorts and undid them. She relinquished her hold on his shorts and they fell to his ankles.

Mathew grabbed hold of Jennifer's shoulder whilst he lifted his feet to enable Jennifer to remove them. Then Jennifer quickly took down his underpants and he stepped out of them.

Mathew's penis exposed to the outside air sprung instantly to attention as the two strange girls stood staring right at it. His hands moved to cover his groin from their gaze, but Jennifer lightly slapped his hands and said, "Mathew, leave yourself alone."

Mathew's two and quarter inch boner bounced around as Mathew moved around the room naked.

Kylie and Angela both sat staring at the naked second grader as he helped Jennifer tidy up the dirty dishes. They kept trying to catch a glimpse of his boyhood whenever they could.

"Okay girls, I'll finish cleaning up the kitchen you two take Mathew up stairs for his bath" Jennifer instructed.

"I don't want them to give me my bath, I only like it when you do it" Mathew pouted.

"Mathew, Angela and Kylie are my helpers tonight and you need to do what they say. If you don't they'll spank you and then I'll spank you and I'll tell your Mom and Dad and they'll spank you. Now, don't argue, I have to get the kitchen cleaned up so my helpers will bath you, understand?"

Still pouting Mathew replied,"Yes" very sulkily.

Turning toward Angela and Kylie she gave detailed cleaning instruction so the girls knew exactly what they were allowed to do and so did little Mathew.

"Be sure to clean him up well, especially his penis and ball sac and be sure his bottom is clean".

As the two girls took Mathew off towards the upstairs bathroom Jennifer called out, "And if Mathew gives you any trouble, spank his little bottom good and hard till it's a deep pink."

"Oh we will." Angela called back.

Upon entering the bathroom the girls ran the bath then soaping up two washcloths both the girls began the task.

As Angela and Kylie got Mathew's face and arms and chest done, Kylie told him to stand. Soaping up their hands they applied them to his still very erect little penis and began taking turns to rub. He giggled and tried to back off but was stopped by the glass partition.

"Mathew, quit fooling around. I have to wash you properly and you need to stand still. You don't want me to have to spank you do you?" Angela asked.

"No." The boy responded as he moved his hands away allowing both the girls access to his penis and testicles.

Angela began to rub and wash his tight little scrotum whilst Kylie washed Mathew's penis.

When they were satisfied they had thoroughly washed his groin area Mathew was turned around and the girls washed down his back and did his butt cheeks.

"Bend over a little Mathew," Kylie instructed as Angela assisted Mathew to bend over. Kylie soaped up her finger and pressed it against the boy's anus.

He wiggled and giggled at this new sensation.

Moving her soapy finger up and down Mathew's little anus she stroked her fingers tantalisingly across the tight muscles of Mathew's sphincter.

Finishing up, both girls ensured they dried every conceivable inch of Mathew's body before dressing him in pyjamas?

It didn't happen on this occasion because Mathew was well behaved but on some occasions the girls Jennifer had assisting her were given the added bonus of being able to spank their charge. Such an activity never failed to make the girls involved very horney.

The first older boys that Jennifer had babysitting contact with were three boys only a year younger than her when she was in 8th grade. She was not the usual babysitter of Mark Livermore but on this occasion his parents had been called away suddenly to a sick elderly parent and the regular babysitter who was much older was not available at such short notice.

Jennifer's reputation for no nonsense and strict disciple was just what Peter and Tiffany Livermore wanted in their babysitter. Tiffany knew Gail Dailey, so it was soon arranged that Jennifer would mind Mark even though he was only a year younger than Jennifer.

To add to Jennifer's challenge Mark had two friends, Luke Vella and John Kristos sleeping over that night. This had already been arranged before Mr Livermore got the urgent call to attend his ailing father.

Before he left Mr Livermore laid down the rules to his son Mark and the other two boys. He left no doubt that Jennifer was in charge and that he would broke no disrespect of their young babysitter.

However almost as soon as the parents had departed the boys began to make life difficult for Jennifer. They snuck out of the house on her and she had a difficult time getting them back home. Eventually faced with three boys who were almost her age which she was not capable of handling physically herself she rang her mother and asked for help.

"I'll be right over" Mrs Dailey informed her eldest daughter.

"Oh, and Mom, bring a belt. I think we are going to need it" Jennifer informed her mother.

"I'll bring the big wide one that I guarantee will make an impression and should do the job really well, it always has on your bottom when I have used it" Mrs Dailey informed her blushing daughter over the phone.

Jennifer didn't say a word to the boys about the phone call as she went into the living room to watch television with the boys.

She was forced to sit on the floor and watch the television as none of the boys would move for her even when she asked nicely.

Mark and the other two boys gloated with a gleeful smile when they forced Jennifer to sit on the floor. They felt they had won another battle.

Little did they know!

Suddenly, the front door flew open and in walked Mrs. Dailey carrying a rather large belt. Mark, Luke's and John's eyes all immediately went wider and their attention was now thoroughly on the Mrs Dailey.

Gail Dailey handed her daughter the belt and said, "Now boys listen to Jennifer and listen well as that belt Jennifer is holding is about to give the three of you a sound reminded of who's in charge here."

"Right you little twerps" Jennifer said to the three boys, "Give me a hard time will you, well your about to find out just what hard means. A good hard bare naked strapping is what you three are about to get. Take all those clothes off now."

"No! I'm not taking off my clothes for you and you aren't going to spank me either" Mark defiantly asserted.

At that Mrs. Dailey interjected and said, "Young man you get those clothes off now or I'll do it for you and I'll whip you with that belt when Jennifer is finished if you're not very careful. Now get to it now."

The boys could tell that Mrs Dailey was very resolute and determined in this matter.

Luke was the first of the boys to weigh up the consequences of not doing as he was told and slowly stood up.

Luke was keen to minimise any punishment so he quickly pulled his black tee shirt over his head and undid his faded blue jeans and lowered them to the carpet and stepped out of them, leaving him only in his black undies.

He hesitated only momentarily before placing his fingers on the waistband, and then slowly he pushed his undies down and off his feet.

Luke now stood completely naked before his two friends and Jennifer and Gail Dailey.

His penis had grown somewhat in the last six months and was the quite respectable size of 4 inches erect for a twelve year old. His hairless ball sack hung down low for about two inches and it gently swayed back and forth showcasing his chestnut sized testicles as Luke stood fidgeting nervously from side to side. He had a very small, sparse dusting of public hair extending about a half inch to either side and to the top of his penis.

Mark was also desperate to minimise his punishment so taking the example of Luke he quickly removed his white tee shirt then pulled down his shorts and Calvin Klein green boxers.

Mark's bobbing three and three quarter inch boner instantly bounced into view. His penis though not quite as long as Luke's was thicker, and was topped by a small silky bush of pubic hair, which was thicker, darker and more noticeable than Luke's. Mark's balls had already begun dropping and were about the same size as Luke's.

John was the last to remove his clothing and he was blushing profusely. Seeing his two friends naked had only confirmed what he was dreading. He paused for what seemed to him ages before he could gain the strength and resolve to grab the waist band of his white briefs and pull them down.

Both his friends had seen that he was sporting a raging hard on. To John's humiliation, he was now forced to reveal his hairless groin and his penis in all of its three inch glory for the first time to his closest friends. John was eight months short of his thirteenth birthday and he was, unlike his two twelve year old friends, still a hairless little boy down there where it really counted.

John had never given anyone in the past few years a chance to see him naked, it was just way too embarrassing.

His balls were no bigger than marble sized, smaller than most of the eleven and twelve year old guys that he had seen naked as NEWDD's. Even those like John who were without pubic hair, were mostly bigger in that department than himself!

John blushing profusely was not only ashamed to be naked before his friends, but feared that he would be seen as very immature for his age.

Mark and Luke both smirked at seeing their best friends little boy genitals, but they were far more interested in keeping out of trouble themselves at that moment in time than torment their friend. That could wait till another day!

Jennifer made the boys pick up their clothing items and fold them neatly before instructing Mark who was the ring leader to, "Bend over the arm of the couch."

Somewhat apprehensively, Mark moved to the couch. His erect penis, sticking out parallel to the floor, bounced back and forth with each step toward the couch. "Bend over the arm" Jennifer commanded.

After had taken up his position Mrs Dailey said, "Mark Livermore this is what you get for not doing as you were told and doing as Jennifer instructed. Now you will be whipped real good."

Luke and John watched in fear as Jennifer raised the belt and came down with it across the globes of Mark's bare backside

It was a hard stroke and it stung. Mark reached to protect his naked bottom from another assault.

"Keep those hands away, Mark" Jennifer commanded as she landed another hard blow which landed squarely on his bottom.

It too stung badly, but Mark was a tough guy and he stubbornly refused to cry in front of his friends, Jennifer or her mother.

Again however his hands went to protect his backside but they were quickly removed when the belt came down with full force upon Mark's fingers, causing him to cry out in pain.

Jennifer continued her relentless reign of strokes; one stroke after another reigned down.

Mark couldn't hold out any longer his bottom was now becoming very sore and he began to cry.

The blows continued from Jennifer and he began pleading for his strapping to stop.

After another few blows hit their target Jennifer stopped.

Standing up the boy angrily yelled, "I hate you. I hate you both" as he rubbed his very warm bottom and began to dance around the room.

"Over there and stand in the corner whilst I deal with your two friends" Jennifer commanded as she pointed to a vacant corner of the living room.

Soon Luke was positioned face down, bottom up, just like Mark before him; his feet were not touching the ground.

Jennifer rubbed his white cheeks, brushing her fingers long Luke's butt crack. It felt nice and cool to Jennifer's touch. It wouldn't feel cool for very much longer.

Jennifer started spanking Luke and like Mark she really let him have it.

Luke started shrieking after only the first smack. He kept it up as Jennifer alternated the cheeks she strapped.

Luke was soon kicking his feet and bucking his bottom but Jennifer kept up the strapping until his bottom was cherry red. As soon as Jennifer let Luke up he started hopping up and down rubbing his very red bottom. He put on quite a show; his modesty was forgotten as he danced around.

John got the same punishment and when released he too went hopping up and down on his bare feet, rubbing his burning red bottom before he was sent to join the other two boys in the corner.

The three boys all had very erect penis's and in the case of Mark and Luke they were dripping pre-cum as they were left standing there in the corner to contemplate just how Jennifer Dailey now had assumed complete control over their lives.

End Chapter 4