Chronicles of a Neighbourhood Babysitter Chapter 7

Chronicles of a Neighbourhood Babysitter Chapter 7
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: 7 JENNIFER DAILEY AGED 13

The previous year when Jennifer was twelve years old she had received a bare naked spanking from her mother in front of four of her sister Caitlin's friends, Chelsea Horden, Helen Foy, Michaela Grace and Terri Walker

Terri Walker even though she was only ten years old at the time had somehow already learnt a lot about influence and using people. She offered to keep her silence about Jennifers humiliating spanking at a price. She would not tell any of the boys Jennifer dominated and punished whilst babysitting about how Jennifer was herself punished as long as Jennifer agreed to a set of conditions.

The conditions that Terri Walker forced on Jennifer were that Jennifer would have to tell Terri all the details of all her babysitting conquests. She wanted Jennifer to try and get all her babysitting charges naked. Then tell her all about them, maybe even invite Terri over to witness the event some times if that was possible. If Terri wished, Jennifer would also have to submit to Terri in private and be punished by Terri just like she punished her babysitting charges.

So it came to pass from a very early stage in Jennifers babysitting career that she was a cocktease to all the boys and a tormentor of her charges but the table was completely turned when it came to Terri Walker. What the boyfriends were unable to get Terri had open access too if she wished!

Thankfully for Jennifer in the first year after witnessing her spanking Terri was satisfied in just hearing the tales of conquest from Jennifer and on four or five occasions accompanied Jennifer to her babysitting duties and witnessing first hand Jennifers babysitting techniques.

This changed dramatically after the episope with the Shaw- Davis family. Terri who was now 11 years of age seemed to find the whole account of Mat then Rebecca's stripping and punishment totally erotic and arousing. So much so that when Jennifer had finished her detailed description of the naked Shaw-Davis children Terri instructed Jennifer that this time she wanted Jennifer to join her in a meeting of a special secret girls group that Terri ran called 'Le Femme Chics'.

As part of her initiation into 'Le Femme Chics' Jennifer would be required to strip naked before Terri and the other members and submit to being punished just like Jennifer had herself punished Mat and Rebecca.

Jennifer was totally taken aback by this request from Terri. For the past year she had been the dominant one, the one in total control. Now with that single sentence Jennifer's whole world was reeling.

Suddenly she was experiencing domination from the other side. She had the feelings of fear and apprehension that all her charges experienced when she took control of them.

Jennifer's resolve however did not prove hard for Terri to break. Jennifer put up far less resistance than Rebecca had done to Jennifer's demands only days ago. Just like most of her charges she was soon begging for mercy and a reconsideration of Terri's demands.

Just like Jennifer's attitude with all her charges, Terri Walker proved unmovable, insisting Jennifer strip totally naked immediately and undergo her initiation or Terri would be forced to tell everyone, especially Jennifer's baby sitting charges about the Daily household discipline regime.

Faced with the inevitable consequences of not agreeing to Terri's request and only too aware that she had often told Terri all about how she dealt with her victims if they did not cooperate, Jennifer humiliatingly capitulated and agreed to be initiated into 'Le Femme Chics'

Terri ordered Jennifer to follow her down stairs to the lounge room. "Do exactly as you are ordered, or you will be over my lap for a spanking session. Understand?' Terri said.

"Yes" Jennifer replied meekly.

"Oh that reminds me girl. When you in a meeting of the 'Le Femme Chics' or are naked before me or being punished you refer to me as Mistress on all occasions. Other times, Terri is ok" Terri informed the again blushing girl.

"Yes ….. Mistress" the now totally humiliated and submissive Jennifer replied.

Jennifer followed the smirking Terri down stairs from Terri's bedroom and into the lounge room of the Walker house.

"Girls, welcome our latest initiate Jennifer Dailey" Jennifer heard Terri announce to some one in the lounge room as she walked in. Soon Jennifer followed Terri into the lounge room, mustering all her will power to stop herself from running away.

Jennifer gasped as she saw a group of girls sitting in a circle on the lounge room floor. There were smiles and smirks on the faces of most of these girls when they saw Jennifer walk in.

There sitting on the floor were her sisters 11 year old friends from 6th grade, Chelsea Horden, Helen Foy and Michaela Grace along with a 12 year old girl from the 7th grade Amanda Hermann who was the younger sister of her ex boyfriend Nicholas Hermann and a 13 year old girl from her own grade, Sarah Roberts. If this was not a big enough shock to Jennifer it was the identity of the sixth person sitting in the circle that caused Jennifer to drop her jaw and stare in amazement.

Her sister Caitlin was sitting there with a huge grin across her face obviously enjoying her sister's embarrassment.

"Right Jennifer, go stand in the middle of the circle facing me and remove all your clothing" Terri callously ordered.

This bought a giggle from some of the girls and a huge blush from Jennifer.

As instructed Jennifer reluctantly moved into the centre of the circle and began to undress. First she kicked off her sneakers. Jennifer was blushing and embarrassed to even remove these simple items, items which other people regularly saw her not wearing.

Jennifer looked over at Terri; she had a huge grin on her face. Oh how she wanted to smash that smirk off her conceited face, but for the first time in her recent life she was powerless to do so!

Jennifer knew she could expect no mercy from Terri, that grin told it all. She hadn't displayed any mercy during her domination and humiliation of the boys and girls she babysat and now Terri was going to ensure she experienced the same treatment

Jennifer trembled with nervous apprehension as she bent over and lifted one foot then the other removing her light blue socks.

Jennifer had slender ankles and pretty feet.

"Hurry up you're stalling. Get moving or you'll get the worst bare naked spanking of your life" Terri warned.

Jennifer unbuttoned her soft pink shirt and slid it off her body. Her face was red with shame as she stood in her jeans and pink AA bra. Though her breasts were basically still non existent her erect nipples were silhouetted against the thin silk bra.

"Take your jeans off next" Terri ordered.

"No Terri, please don't make me do this" Jennifer in her humiliation and embarrassment pleaded again.

When she received no reply to her plea except an impatient stare and body stance from Terri, the now gently sobbing Jennifer unbuckled her jeans, unable to postpone her fate any longer.

Jennifer pulled her jeans down around her ankles and stepped out of them. Her pink flowered panties barely hid her secrets.

As Jennifer straightened up, her lips were trembling and she couldn't meet the gaze of the still smiling Terri Walker or any of the other girls in the club.

Though what she was wearing was as much as she wore at the beach on this occasion Jennifer felt almost naked.

"Good, now remove your tiny pink bra and let's get a good look at those little tits of yours," Terri ordered.

Jennifer was by now openly sobbing. Her shoulders shook as she reached back and unhooked her bra. She initially went to place her hands over the tiny cups then realizing that covering up would earn her the wrath of her tormentor and possibly further punishment she let her pretty pink AA size bra fall to the floor and forced her hands down by her sides.

Terri and the other girl's eyes focused on Jennifer's still small, almost flat breasts which were dominated by her erect pink nipples

"Put your hands on your head," Terri ordered, "from the stories you have told me you should be familiar with that position."

Trembling and with tears pouring from her eyes Jennifer obeyed and Terri moved in front of Jennifer and felt Jennifer's flat breasts with her smooth silky hands. Terri might only have been 11 years old but somehow she knew exactly what to do. Jennifer wondered if all the other girls in the circle had suffered similar humiliation at the hands of Terri Walker!

Terri slowly circled Jennifer's erect nipples with her thumbs as Jennifer blushed an even reddened shade of shame.

"I'm going to finish undressing you" Terri informed the mortified Jennifer.

Terri then grasped the waistband of Jennifer's pink flowered panties and as Jennifer shut her eyes and let out a moan of humiliation, Terri yanked them down to Jennifer's knees, revealing a sparse growth of golden brown hair that barely fringed her slit. Jennifer's pink puffy lips clearly showed through the thin strands of hair.

Terri knelt in front of Jennifer and lifted first one of her bare feet, then the other as she removed Jennifer's panties.

Terri's eyes were now barely inches away from Jennifer's slit. Unable to resist any longer Terri reached out and easily pushing through the sparse pubic hairs parted Jennifer's pussy lips and poked her forefinger into her virgin slit.

Jennifer gasped at this forced intrusion into her most private and intimate of parts.

Then just as quick Terri removed her finger and stood back up.

"There will be plenty of time to explore in there later. For now turn around and let me see your ass" Terri ordered the red-faced 13 year old teenager.

Slowly Jennifer turned, revealing her perfectly shaped buttocks.

"Nice and white, but by the time I have finished with you today it is going to be very red, very, very red and sore" Terri informed the now petrified Jennifer.

"Right stand straight and keep your hands on your head' Terri ordered,"I want to inspect your body."

Terri moved immediately to Jennifer's pussy and Jennifer was soon moaning and wiggling around in front of the assembled girls as Terri with some practised skill again pushed her fingers in and out of Jennifer's pussy.

Terri soon located Jennifer's virgin clitoris and was soon pulling, poking and stroking Jennifer, quickly stimulating her clitoris and greatly arousing Jennifer's whole body.

The naked teen was soon bouncing up and down, as Terri placed one finger in Jennifer's cunt and one in her ass. She continued to push them in and out, doing her best to make Jennifer cum. Jennifer responded to her building arousal by moaning and gasping as Terri's fingers touched first one erogenous area, then another. Finally with her head thrown back, her heart pounding and gasping for air Jennifer was expertly masturbated to her first public climax by Terri.

This first climax was not however anywhere near enough for the now very aroused Terri Waker. From a shoe box she produced a thick adult sized dildo. Again Jennifer was amazed how an 11 year old knew so much about sex and sex equipment. The dildo was made of clear Perspex and had two balls as a handle grip. In a few moments she would push the dildo into Jennifer's ass.

"Lie down on the floor where the towel is laid out" Terri ordered.

Slowly and reluctantly Jennifer followed orders.

"Now lie on you tummy and push your but up into the air"

Terri opened a tube of lube from the shoe box and rubbed some on the dildo then she lubricated Jennifer's asshole.

Jennifer was screaming out for Terri to stop but Terri ignored the protests and guided the dildo into Jennifer's ass crack. Jennifer screamed a different tune as the adult sized dildo cock pushed against her well lubed sphincter before it broke through and thrust up inside her virgin ass.

Jennifer was sweating; the dildo cock was hurting her. She was soon screaming at the top of her voice and bawling out loud as Terri pushed ever deeper into Jennifer with the dildo.

Soon Jennifer was crying profusely as Terri moved faster and faster in and out with the dildo. Jennifer was soon a mess covered in a lather of sweat from fear and exertion.

Every orifice in Jennifer's body had been penetrated either by fingers or a dildo, though technically she remained a virgin as none of Terri's fingers had penetrated Jennifer's vagina that deeply that her hymen had been breached.

Finally after Jennifer had had her second climax in a matter of minutes Terri withdrew the dildo but if Jennifer had any thoughts that her ordeal was over she soon discovered otherwise.

Terri presented the brown faeces stained dildo to Jennifer's mouth and ordered her to lick it clean. Jennifer gagged as she smelt the filth on the dildo. Only with a supreme effort and enormous willpower did Jennifer begin to lick the rim of the dildo slowly clean, dry reaching between licks.

When Terri had last seen Jennifer naked the then 12 year old had only gentle swellings that hinted of the breasts to come. At that time her nipples were perky and pink, her areolas, slightly lighter, looked puffy and swollen and Jennifer had not even the hint of hair to mark her developing sexual maturity between her legs.

The twelve months since then had not improved Jennifer's breast development much; just a slight swelling of breast had grown in that time. Her nipples however showed clear evidence of maturing and in their current aroused state were very prominent.

Between her legs however things had happened. From having no sign of any pubic hair, Jennifer now had a sparse fringe of golden brown hair. It was certainly not the thick bush some 12 and 13 year old girls already had by that age and it didn't even cover her slit and pink puffy lips yet Jennifer was very proud of this growth. With her lack of breasts she could easily be mistaken for a little girl but the sparse pubic hairs were proof positive that she was a young lady not a little girl.

As well in the last six months she had started her periods. A sure sign she was a woman not a girl.

Shaving off the pubic hair of any of her victims who were old enough to have any was a favourite pleasure of Jennifer now to her horror Terri turned the tables on her!

Removing a pair of scissors from the box, Terri commanded, "Take these scissors and trim your pubes while we watch" then added, "You can then shave off what you can't get with the scissors."

Jennifer took the scissors in her hand and for the briefest of moments thought about threatening to stab Terri with them unless she allowed her to go.

The thought was impossible. Terri would tell all her secrets to everyone and now she knew a lot more detail to add to her original stock of knowledge.

She was defeated and she knew it. Terri knew it too!

Jennifer started clipping her sparse pubic hair with the scissors in front of the giggling and smiling group of girls. As she did so she was again sobbing as she carefully cut her precious pubic hairs back to stubble.

When all the hair had been trimmed as short as possible with the scissors Terri took the scissors and placed them back in the box and then gave Jennifer a hand towel, disposable razor and a can of shaving cream.

"You have to shave it all off, every last hair. I want you as bald as a little girl" Terri informed the blushing Jennifer.

Jennifer in abject misery did a thorough job with the razor.

When she was finished Terri surveyed Jennifer's handy work and thought to herself how Jennifer with her flat chest and bald pubic region really looked like a little girl.

Jennifer just lay there on the floor crying like a baby in front of everyone as she lamented the loss of her pubic hair, her most prized outward sign of maturity.

The rest on the floor was only very short for the naked thirteen year old as Terri soon ordered Jennifer to get into a position with her legs spread wide apart on the floor.

Terri then made Jennifer reached down and pull her pink pussy lips wide open for Terri to undertake a detailed inspection of Jennifer's most private parts.

The assembled girls focused their attention on the scene splayed open in front of them. Jennifer's delicate pink labia led into a still immature but well developed pussy with an average size clit.

Terri smiled as she again poked her finger inside Jennifer's vagina and poked around. Jennifer moaned as Terri very expertly for an 11 year old fondled her pussy, Jennifer's aroused clit which grew rigid under Terri's finger ministrations.

As Terri was carrying out this additional inspection Jennifer laid on the floor with her eyes closed, crying in front of her tormentor.

Jennifer opened her eyes when she felt Terri stop fingering her and gasped as she saw her tormentor pick up the dildo and lube it again.

"Please no," Jennifer begged as Terri moved the dildo cock into place between Jennifer's widely spread legs whilst Jennifer was made to continue pulling her pussy wide open with her fingers to allow the dildo to thrust up inside her exposed vagina.

"No" Jennifer screamed out as the rigid adult sized dildo penis pushed against her unbroken hymen. Then Jennifer screamed as the thin membrane tore. A trickle of blood ran out of her as Terri plunged the dildo up and down inside Jennifer's vagina.

To Jennifer's surprise the movement of the dildo in Terri's hands was starting to feel good. Soon she was unable to stop herself and began to move up and down with the rhythm of the dildo

Terri Walker watched Jennifer's erotic movement's with great satisfaction knowing that she had deflowered yet another girl, taking her total now to seven!

At this stage Jennifer only suspected, but since the 5th grade Terri Walker had slowly built up her own private cohort of girls who she had total sexual domination over and called them 'Le Femme Chics'. After her own deflowering Jennifer was about to join the other girls in total sexual subservience to their young mistress.

There was one final indignation in Jennifer's transformation from the dominant to the dominated. Her spanking!

Terri bought a dining chair into the circle and ordered Jennifer over her lap. Slowly Jennifer positioned herself face down, bottom up on Terri's lap giving Terri a perfect view of Jennifer's tight perfectly proportioned lily white round ass.

Terri admired the tan line that separated the exposed and covered skin from when Jennifer had worn her bathing suit in the privacy of her back yard pool. Jennifer's legs, torso and arms were nicely tanned, in contrast to the white skin below the bikini tan line marks that ran across her ass making Jennifer look even sexier.

Terri examined Jennifer's perfect ass that lay before her eyes with its cute little dimples and wondered how long it would take once she started spanking to turn those pretty butt cheeks crimson?

Jennifer's tormentor softly rubbed her fingers along Jennifer's butt crack. It felt nice and cool to Terri's touch but she knew her bottom wouldn't feel that cool for much longer.

Draped over Terri's lap, Jennifer's feet were not touching the ground. Terri held Jennifer's back with her left hand and reached over with her right hand to Sarah Roberts who handed Terri a professional slave punishment paddle. It was made of U.V. stabilised polymers and had small perforation holes through its surface ensuring minimal wind resistance and that the maximum impact velocity could be achieved.

Terri raised the paddle in her right hand and started spanking Jennifer.

To Jennifer's total humiliation and the amusement of Terri and the girls, Jennifer started shrieking after the very first smack. She was proving to be a real woos compared to all the children she herself had disciplined, nearly all of whom could hold their emotions in for longer than the first smack.

Terri loved how the early strokes with the paddle made solid red marks across Jennifer's pale butt cheeks which gradually merged into a nice red glow all over. As Terri continued to reign down stroke after stroke Jennifer continued to yell and plead just like her own charges had done and also just like Jennifer had done to them in the past, Terri Walker now just smiled and enjoyed Jennifer's suffering.

Soon Jennifer was crying and as the spanking continued unabated she was soon bawling like a baby whilst kicking her feet and bucking her bottom around giving the assembled girls an intimate view between her legs. Terri however had her firmly pinned down with her left hand and kept up the relentless stream of strokes to Jennifer's now very cherry red bottom.

When Terri finally let Jennifer up she started hopping up and down rubbing her burning, very sore, crimson red bottom. Jennifer put on quite a show, much more so than most of her own young charges who she had relentlessly smacked herself. Any thought of modesty or dignity was completely forgotten by Jennifer as she franticly danced around in front of her amused tormentors.

End Chapter 7