Neighbourhood Babysitter

Published on Nov 30, 2006

Bisexual

Chronicles of a Neighbourhood Babysitter By Steam Train (steam_t2000@yahoo.com)

Chapter: 5 MAT DAVIS AGED 14

When Jennifer was still 12 years of age and in the 7th grade she had her first real boyfriend. By the time Jennifer was 13 years old and in the 8th grade there had been four boys who Jennifer classed as boyfriends.

The first, Peter Lindon was in Jennifer's grade and the second Nicholas Herman was a grade ahead of her, but both boyfriends never amounted to being more than guys she was close friends with and that accompanied Jennifer to a occasional school dance and in the case of Nicholas also to the movies on one occasion and a picnic with Nicholas's family to the Disciplinary Centre in Poulton Park in Downtown Eastbrook.

Jennifer had thought about trying out her domination techniques on Nicholas but they broke up before she built up the nerve to put her desires into action. Jennifer was never really sure why Nicholas broke off their building friendship. Just when she was prepared to make some very minor concessions to Nicholas like kissing and cuddling he left her for Keira Drew another girl in Jennifer's year.

The fact Nicholas went straight to Keira was something that Keira regularly brought up in passing comment with Jennifer for many months after that. Many of the girls in her grade adored Nick's good looks but even though he must have known he was popular and well liked he seemed embarrassed around girls and broke off his friendship with Keira as soon as it looked like it might be getting a bit heavier, just like he had done with Jennifer.

This shitted Keira no end but made Jennifer feel a bit better. After that Nicholas only seemed to go on dates with groups staying clear of any one-on-one situations that might develop.

Her third boyfriend was the first that she came to dominate. Paul Macarthur was 13 years old like Nicholas and a grade ahead of Jennifer at school

With much urging from Terri Walker who had great influence and power over her, Jennifer finally succeeded after a number of failed attempts in convincing Paul to strip naked in front of her.

She was not disappointed in what she saw.

Paul stood 5 feet 4 inches tall and when he was standing naked before Jennifer he revealed he had a nice chest, with even a few hairs growing in his arm pits. He had some muscles already and looked cute with his messed up style of dark brown hair.

Paul had a long but skinny dick as was quite common for 13 year old guys. It was circumcised and surmounted by a small but thick bush of pubic hair and below his balls hung down low but were not covered with any hairs. Unfortunately Paul's father got a job promotion and the family had to move interstate, ending what promised to be a sexy if one sided relationship as far as Jennifer was concerned.

Her fourth boyfriend after she had, had her fun with Paul was Jonathan Lewis one of the really cute `hot' guys from Jennifer's 8th grade. He was 13 years of age the same age as Jennifer.

Jono as he was known to everyone had just turned 13 but Jono actually looked younger than his 13 years. He really looked as young as the new 6th graders at school but what cute looks they were. Jennifer had hoped that those young looks were just on the surface and that he had a long hairy dick like her previous boyfriend Paul.

There was one way to find out and on the urging and insistence of Terri Walker, Jono like Paul before him was about to face his moment of truth. It took some time but finally Jono was backed into a no win situation. If he resisted Jennifer's advances he had no doubt Jennifer would keep her word and tell everyone at school how the so called `hot' guy was in fact that shy he would do nothing with a girl, if he allowed Jennifer's advances he knew his shame would be revealed. It was better he decided to have Jennifer know his secret than loose face before the whole school.

On this day despite his best efforts to put Jennifer's advances off yet again, Jennifer had stripped Jono naked except for his underpants Jennifer reached over and despite his blushing and last ditch protests pulled them down and off as well.

She gasped in surprise as she got her first look at her new boyfriends' naked dick and balls. If she was happy with Paul's body she was devastated with Jono's pathetic offering.

His penis was little boy size, being no more than 2" erect and his balls were equally small still tucked up tight out of view behind his pencil thin penis.

As Jennifer reached over and grabbed Jono's little penis she couldn't resist saying to him, "Is this what you were trying to hide? I don't blame you Jono; I would be embarrassed about anyone seeing such a small package"

The comments plus the humiliation of having his most private of parts felt for the first time soon had Jono bawling his eyes out like a little boy.

Jennifer felt bad about making him cry but deep within she was enjoying the humiliation that Jono was exhibiting.

After her conquest of Jono and with so little to offer her, Terri Walker soon had Jennifer move on to her next desire Mathias Shaw-Davis III.

Mat Davis as he often abbreviated his name to at school was at fourteen years of age a year older than Jennifer and a High School Freshman at West Eastbrook High

He was the eldest child of the Reverend Mathias Shaw-Davis II, the local Episcopal Minister and his wife Eleanor.

Mat had a 12 year old sister Rebecca, a 10 year old brother Joseph and an 8 year old sister Ruth.

Occasionally Jennifer had babysat the two younger children on occasions when the Reverend and his wife had a church function to attend and Mat and Rebecca were not available to mind their younger siblings.

On this occasion as the Reverend and his wife returned home the Reverend Shaw-Davis commented to his wife how well behaved his two youngest charges were under Jennifer's babysitting. The total opposite to the unruly behaviour he had found last week when Mat and Rebecca had been in charge.

Jennifer complimented the Reverend on his kind comment and seizing the opportunity with the hope she might get to baby sit the younger two siblings more often and in the wash up get to spend some time closer to Mat, she offered the idea that it was her experience that made the difference.

"I might be a year younger than Mat but I have much more experience in dealing with kids of all different ages and of both genders than he or Rebecca does" Jennifer offered.

The Reverend Shaw-Davis was a strict traditionalist and this belief flowed through to the way he had bought his family up. His father, Bishop Mathias Shaw-Davis had bought the Reverend up that way and there was no doubt in the Reverend's household who was master and head of the household. Eleanor Shaw-Davis played out the role quite happily of the subservient mother and housekeeper.

The Reverend Shaw-Davis looked at his wife and said, "You know Eleanor I do believe Jennifer makes a very sound point. You and I both know that Gail Dailey has bought her daughters up in a God fearing household where traditional values are strong just like we urge and encourage all our parishioners to implement in their own homes. Every time we leave the children alone we come home to disruption and bad behaviour. I know Matt is a year older than Jennifer and that Rebecca is only a year younger but Gail Dailey has ensured that Jennifer has had far more experience in discipline and childminding than our two older children. I see no reason Jennifer should not be put in charge of the whole family when we have to go out".

This was more than Jennifer had hoped to achieve with her offer. Never did she consider she would be put in charge of Matt or his sister Rebecca as well as the two younger children.

Mrs Shaw-Davis took very little convincing. She always left such matters to her husband as a good wife should though she did ask Jennifer about her experience with older children.

This was just the question Jennifer was hoping to be asked. She told the Reverend and Mrs Shaw-Davis of her successful disciplining of Mark, Luke and John and her subsequent lack of trouble from them. She told of other boys and girls not much younger than herself that she had successfully babysat.

Hoping to set up her deepest desires she boldly informed the Reverend and his wife, "Of course I would expect full co-operation from Mat and Rebecca even though I am close to them in age. I am much more mature in my attitude than either of them I believe and I will not tolerate any misbehaviour. If they do not co-operate with my orders I will punish them with a bare naked spanking just like mum has used on me in the past on your urging and teaching".

This was music to the Reverends ears. Yes he had encouraged his parishioners to return to the traditional values. Here now in front of him one of his young parishioners was confirming not just that she had listened but that she had acted on his sermons. No wonder Jennifer Dailey had such a good reputation amongst the congregation as a very good babysitter.

So it came to pass that Jennifer was appointed to baby sit the whole Shaw-Davis family with complete adult authority over the four of them, despite the initial vehement opposition of both Mat and Rebecca. This opposition soon turned to complete acquiescence after the Reverent threatened to give his two eldest children a bare naked spanking in front of their younger siblings.

God was on her side Jennifer decided, because the very first opportunity Jennifer got to baby sit the Shaw-Davis children after this decision was made, provided an opportunity where only the two younger children and Matt were at home that night. Rebecca was accompanying her parents to a church youth camp for 11 and 12 year olds. In fact Jennifer's sister Caitlin was also attending the camp.

The first part of the evening was uneventful. Mat stayed out of Jennifer's way completing homework in his room. Being a high schooler Mat was allowed to stay up a bit later than his two youngest siblings. Mat has not long come down to the lounge room to watch the TV when Jennifer ordered both Joseph and Ruth to go to the bathroom and undress so she could wash them ready for bed.

Jennifer looked at Mat as she gave this order and though he appeared to take no notice but she was sure his cheeks blushed slightly.

Mats father had been explicit in his order to his son before Jennifer had arrived that he was under Jennifer's control and discipline. Mat was left in no doubt what that meant or what the consequences would be to him if he disobeyed her instructions.

After Jennifer thoroughly washed her two younger charges, tucked them into bed and read then a story she returned to the lounge room. Mat had not moved, he was sprawled out on the lounge watching the very end of a programme.

`All in bed?" he casually asked.

"Yes all washed and tucked in tight" Jennifer replied.

"Mat it's nearly half past nine and I see that the programme your watching has nearly finished. As soon as it's over I'll take you up to the bathroom and wash you ready for bed too!" Jennifer informed Mat.

It was a bold move on Jennifer's part. How fearful of his father's wrath was Mat? Would he refuse?

Jennifer needn't have worried the effect of her instruction was startling and immediate. Mat blushed immediately his cheeks turning bright red as he opened his mouth to protest. He had to draw in a deep breath before he could even manage to utter his protest.

"I can bath myself and take myself to bed thank you" Mat politely but firmly replied.

"Oh I am sure you could but that's not the point. I am in charge here on your fathers orders" Jennifer paused for effect highlighting the source of her absolute authority.

"So as soon as the programme is finished I am bathing you so as to make sure the job is done properly like I promised your father and mother" Jennifer added to reinforce her position of power over Mat.

Mat looked up at Jennifer from the lounge. There was anguish showing on his face and tears appeared to be welling up in his eyes.

Jennifer could not miss this opportunity to drive home her new position of power over Mat. She looked Mat directly in the eyes and said "Now you wouldn't want me to have to give you a bare naked spanking for being difficult, would you Mat?"

Jennifer continued to look him in the eyes and when he didn't maintain eye contact or respond she placed her hand under his smooth chin raising his head so that he could do nothing but meet her steady gaze.

"Would you Mat?" Jennifer asked again pressing home her advantage.

With trembling voice Mat shook his head and finally replied, "No Miss."

Jennifer's heart jumped at Mat's use of the word `Miss', like she was his teacher or slave mistress instead of just using her Christian name.

She knew she had him!

When the programme finished Jennifer moved over and turned off the TV. To Jennifer's delight she noticed that Mat was trembling visibly and his face was bright red as he rose off the lounge and walked towards the stairs and the bathroom upstairs.

Jennifer followed behind watching as Mat climbed the stairs admiring his handsome figure which she soon hoped to see totally naked.

She felt very satisfied at this moment. She had confirmed to herself that she could establish control over boys. Not for her the acquiescent infatuation that most girls seemed to readily display to the opposite sex. Jennifer had decided last year that she wanted to be the dominant person in any relationship she built with a boy. That relationship would be on her terms not his. This was the start of putting that plan into practise.

In the bathroom Jennifer got straight into the action.

"Right Mat, take off your shoes then hand me your socks to start with and I'll put them in the dirty clothes bin for you."

Jennifer stood there watching Mat blush and tremble as he stood in front of her slowly removing his clothes. Each stage of his undressing was an incredibly arousing experience for Jennifer as she stood there admiring his smooth hairless chest and narrow waist as he got down to just his jeans.

As Jennifer turned to the dirty clothes bin to deposit Mat's discarded shirt she wondered if he would start undoing his jeans without being prompted. Hearing no movement from him she turned back towards him and she saw immediately that his eyes had began to tear up slightly as he held his hands to the clasp of his jeans, he was wearing no belt and he was making no movement to remove any more clothing.

A thin sheen of nervous perspiration had formed on Mat's body as he stood in front of Jennifer trembling, his eyes down cast and his bottom-lip quivering.

"Hurry along Mat," Jennifer ordered, "drop your jeans and be quick about it!"

Mat slowly undid the clasp button of his jeans with trembling fingers. Not daring to look at Jennifer as he eased down the zipper and slowly lowered his jeans down his thighs.

Acutely aware that he had a raging erection, which tented his cotton underpants and hoping beyond hope that Jennifer would not notice he handed his jeans to Jennifer and at the same time he covered his erection with both his hands, pushing his bottom backwards and almost crossing his legs.

Jennifer could not help but notice such a blatant action to cover up on Mat's behalf however before acknowledging she had seen what he was doing she placed Mat's jeans into the dirty clothes bin on top of the other dirty clothing she had already placed there.

Still trying to cover up Mat looked at Jennifer in fear and anguish, tears still welling up in his eyes as he stood cowering before her knowing the inevitable was about to happen.

"No covering up Mat, you know better than that. Your father would not be pleased if he knew you were playing with yourself in front of me" Jennifer instructed the blushing boy.

Mat knew this comment was correct. His father was very strict and very traditional on all maters concerning sex and bodily functions. His friends at school often talked about "having a wank or jerking off", but he had never dared to make himself ejaculate. His father had warned him many times of the dire consequences in this life and the next for those who masturbated.

A consequence of Mat's abstinence from masturbation was that his testicles were often swollen to such an extent that they would become painful. When the problem had persisted Mat's father had taken him to their doctor to seek advice about this problem, but the Reverend Shaw-Davis had not acted upon the doctor's recommendation that Matt should be regularly masturbated to relieve the swelling and the pain.

The Reverend Shaw-Davis believed that Gods way was to let nature run its course. If his son ejaculated in his sleep even if this resulted in him having erotic dreams this was natural. He could pray for forgiveness and god would understand as this was natural. He did not want to encourage Mat into masturbation even if it was on medical grounds and the doctor's offer of a visiting nurse to perform the procedure though a satisfactory alternative had not been well received by his son and the ongoing cost of the sessions which would have to be met out of his meagre ministerial stipend had added to his reluctance to take the matter further unless his son's condition became worse.

Trouble was, Mat suffered for long periods of days even weeks sometimes between wet dreams and by the end the skin of his scrotum was stretched so tightly around his testicles and that they become unbearably painful to the slightest touch.

His testicles were in just such a condition at this unfortunate time. It had been over a week since his last wet dream.

Only last night as he often did when they became so sore he had rubbed his genitals against the bed sheets so that he was near to making something happen. Scared and unsure of what the consequences would be if he continued he again like all the other occasions willed himself to stop as his father would have expected, battling to overcome the intensity of feeling that he was experiencing just before he reached the point of no return.

As Mat thought about this aspect of his non existent sex life he was roused from his thoughts by Jennifer's voice.

"Stop playing with yourself Matt this instance, place your hands on your head and stand up straight" Jennifer ordered. She knew he wasn't actually playing with himself but the comment added to the deepening colour of his already red blushing face.

Jennifer waited for Mat to obey. She knew that she might have to wait a few more moments for him to compose himself, but she knew that she had him in her power now and that he would eventually comply.

Jennifer folded her arms in feigned impatient whilst she felt a thrill run through her body and a tingling between her own legs as she watched Mat stand straight and reluctantly uncover himself and place his hands upon the top of his head.

Shaking uncontrollably with nerves and blushing a beet red, Mat stood before Jennifer staring in horror as she went down on one knee in front of him and placed her silky hands on either side of the waist band of Mat's underpants.

Jennifer felt Mat shiver uncontrollably as she slid her hands down inside the waist of his underpants and slowly pulled them down. Down till his tan line was fully exposed and the lily white skin of his lower abdomen came fully into view, down until his erect penis temporarily halted the progress down his body.

Looking at Mats now exposed pubic region Jennifer saw for the first time that Matt like Paul had pubic hairs. She had expected that he would, as he was after all in high school and was 14 years old. However she was somewhat disappointed in the amount of pubes he had to reveal.

Mat's lower abdomen was covered with just the slightest hint of golden peach-fuzz and he had only a very thin covering of brown pubic hairs which were less than a quarter of an inch thick above the base of his still covered penis however down both sides of his penis disappearing behind the cotton fabric of his underpants there was growing triangular patches of much thicker pubic hairs.

Jennifer desperately wanted to see everything revealed so she lifted the waistband of Mat's underpants over his penis, watching it spring upwards as it was freed from the confines of the material.

The sight of his naked genitals was an arousing experience for Jennifer as she now fully exposed Mat's most private secrets to her vision. Mats small growth of pubic hair was the only hair down there as his penis and ball-sac were smooth and hairless

If Jennifer was not impressed with the volume of his pubic hair his penis was another matter. It was so much longer and thicker than any of the other boys she had seen during her last year of babysitting.

Kneeling down her face was only inches away from the smooth bulbous head of Mat's erect penis, which she noted had been circumcised, as she slid his underpants down his thighs and to his feet.

"Lift your feet so that I can take them off" she instructed as Jennifer slid the last of Mat's clothing off his feet and she stood upright.

She placed his underpants in the dirty clothes bin and then before Mat could cover himself Jennifer ordered, "Stay exactly as you are Mat and tell me why you have an erection?"

The question had its desired effect as the already blushing boy turned a deeper shade of crimson. Mat could not believe he could have been more embarrassed than he had been when stripped naked but some how he now felt even worse. His mind was spinning he was beginning to feel faint, his face cheeks felt like they were on fire, and he was shaking and trembling from head to foot.

"I don't know Miss" he blurted out in embarrassed reply.

"Well I do Mat" Jennifer replied,"It's a sure sign you need relief, don't you?"

"Oh no Miss. Pa says relieving yourself is a mortal sin' Matt replied.

"Of course it is, but who said anything about you relieving yourself, no I will do the relieving, that is part of my job as your baby sitter to look after all of your needs. There is nothing morally wrong with me giving you relief is there?' Jennifer asked leading her pray on to his doom.

As she expected Mat did not know how to answer this question. What Jennifer said sounded logical to him, even their family doctor had suggested that such action was needed, but in the back of his mind he was terrified at allowing her to touch his most private of parts to afford him relief. He knew it was ok for a doctor to do it or for a NEWDD to have it done but his mind was racing and it was in such a state of turmoil that he could not come up immediately with an answer.

As he was contemplating his answer Matt dropped his hands from his head without thinking about his actions or Jennifer's specific instruction to leave them on his head. Jennifer immediately grabbed at his hands and Mat instinctively resisted Jennifer's attempts to pull his hands away from covering his groin.

Jennifer spoke sharply to Mat, "Look at me Mat." He opened his eyes which he had tightly shut with embarrassment and looked at Jennifer. "Naughty boys and girls get bare naked spankings and you know who came up with that rule?"

"My Pa!" Mat replied slowly.

"Exactly and there are no exceptions" Jennifer responded.

Without warning Jennifer moved behind the naked Mat and delivered six hard slaps to his naked buttocks.

It was such a shock to Mat that it was several seconds before he managed to gasp in astonishment at Jennifer's actions.

Jennifer spoke again; "Now hands back on your head and let's have no more such nonsense."

Jennifer was now able to examine the totally naked Mat at her leisure. His five and a quarter inch penis was still completely erect and pointing upwards from the horizontal at forty five degrees. His swollen testicles had stretched his hairless scrotum so tightly that the skin shone under the bathroom lights that illuminated the room with some intensity.

She raised his arms and examined his arm pits but there was no sign of any hair there except some golden baby peach fuzz.

His lack of body hair was a disappointment unlike his man sized penis. He obviously had only grown his meagre covering of hair in the last six months or so. The thought of his lack of hair bought to mind the way the courts often ordered NEWDD's shaved to heighten their humiliation. Jennifer looked around the bathroom and sure enough there was the Reverends shaving kit sitting on a glass shelf next to the mirror. It was obvious what her next move was going to be.

"Boys are so much more immature than girls at the same age I find and way too modest my mum says. She says little boys should not be so modest about their bodies and I know that little boys should not be allowed to have pubic hair till they can prove their maturity so before I bath you I am going to shave off what little pubic hair you have.

"No Jennifer please don't, please Miss, please!!" protested the helpless fourteen year old realizing that he was about to loose the only body hair he had which really wasn't much.

Jennifer immediately started lathering Mat's father's shaving brush. Then to his continued verbal protests she applied the brush to his genitals spreading the lather evenly.

Giving Mat no time to contemplate his loss any further Jennifer took the Reverends razor from the shelf and with a rush of excitement took hold of Mat's throbbing penis for the first time and ignoring his moans of protestation, moved the razor up and down and from side to side as she began to denude his pubic regions of it's sparse covering of hair.

Mat was beside himself with utter humiliation as Jennifer lifted his penis and shaved the throbbing shaft of any small hairs that have been growing there

When she had finished shaving and wiped away any residue shaving lather Jennifer stood back and looked at her handy work. If anything Mat's new hairless look accentuated the size of his very adequate genitals even more.

Mat looked down at his now hairless groin in total disbelief. His outward sign of manliness had gone, he would have looked like a hairless little boy again except for the size of his genitals. He had waited till he was nearly fourteen years old before his first pubes had appeared now they had been removed in less than a minute!

Jennifer moved back over to Mat and this time cupped his scrotum in one hand and gently felt around the testes with the other.

Mat winched at the pain.

"Are you having much pain from your balls, they feel very swollen?" she asked in a concerned voice.

"Yes ... miss ... um ^Å Jennifer, my Pa and our family doctor say it's a consequence of my abstinence from masturbation that my testicles are often swollen to such an extent that they become painful. As you know miss, Pa has lectured many times at church and in the youth group about the dire consequences in this life and the next for those who masturbate, though the doctor recommended that I should be masturbated by a nurse seeing that I should not do it on moral grounds to relieve the pain and swelling. However neither Pa nor I were keen on that idea" Mat replied hesitantly, unsure if he should tell Jennifer the whole story.

Nodding her head in understanding Jennifer replied, "I fully understand Mat, and agree that because of your upbringing and your fathers position in our community I agree that it would be morally wrong for you to masturbate yourself to relief. However I know from the way that the courts allow relief for NEWDD's that if I were to give you the relief the doctor recommended at regular intervals it would prove to be a most satisfactory solution to your swelling and pain."

With that she gently grabbed Mat's throbbing penis and began to slide what loose skin there was up and down his circumcised penis.

"Ahhhhhh" Mat groaned as he felt Jennifer's fingers grip around his aroused shaft, and he felt the answering throb in the tip of his penis.

"Ahhhhhhh" He moaned again as he writhed his hips, trying to escape the acute sensation he felt deep inside his groin.

Jennifer caused Mat's next groan of misery and sensation when as an experiment she rubbed the palm of her hand over the very tip of his penis.

"Ahhhhhhhhhh, ahhhhhhhhhhhhhhhhhh, ahhhhhhhhhhhhhhhhh Mat groaned as a sensation so acute shot through him that he felt he would die unless Jennifer stopped immediately.

But Jennifer didn't stop, she continued to sensually manipulate Mat's penis and especially the sensitive exposed glans of his penis head.

Jennifer's well practiced milking motion soon had Mat gasping for breath and every nerve and every muscle of his body was on the edge.

"Ahhhhhhhhhh ahhhhhhhhhhhhhhhh. Mat was beside himself, begging Jennifer to stop but at the same time engulfed in a myriad of the most acute sensations he had ever felt in his young life. This was where he never went when he aroused himself in bed, This was the unknown that he feared.

Jennifer felt a surge like an electric shock run through Mat's body as he suddenly arched his back, curled his toes and groaned, a deep guttural noise, a wail of utter anguish and unbelievable erotic sensations.

"Ahhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh" His body shook as Jennifer looked at his penis which she was still rhythmically milking with her fingers.

From the end of Mat's penis erupted a mighty stream of thick white semen. Through all Mats thrusting and gyrating of hips as he experienced his first public masturbation Jennifer did not miss a stroke in her milking rhythm.

"Ahhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh" Mat's wail seemed to go on forever as he continued to pump out copious amounts of semen from his acutely swollen and full testicles.

As Mat's whole body began to stagger Jennifer looked up at him. His head was thrown back and then lashed from side to side and his mouth was wide open gasping for air, as jet after jet of thick white semen continued unabated to burst from the tip of his penis. On and on Mat's masturbation went until the last spurts of semen were drained from him.

Exhausted Mat collapsed onto the bathroom floor ignoring the cold floor tiles and lay there at Jennifer's feet his chest heaving for breath covered in the copious quantities of cum that he had just ejaculated.

Mat sucked at the air. His mind and body were in turmoil. He had never imagined that he could have experienced such feelings. He could feel his heart racing within his chest. He could, he imagined, feel every inch of his skin as his nerves tingled. He was split between utter ecstasy and utter humiliation.

End Chapter: 5

Next: Chapter 6


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