Babysitting the Babysitter - Cover

Babysitting the Babysitter

Copyright© 2021 by Peter Pan

Chapter 1

Erotica Sex Story: Chapter 1 - For years, the hot little babysitter has been the traditional fantasy of so many middle-aged men, most of whom would give away a crate of their best scotch for a few hours indulgence with that sexy little teen. I guess we just got lucky!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   BiSexual   Heterosexual   Fiction   First   Masturbation   Caution  

It’s never easy finding a really good “sitter.” They’re either unreliable as all Hell time-wise, or more interested in chatting to their boyfriends on their cell, than actually preventing that cutesy little ankle-biter from choking to death on a tiddly-wink. In that regard we were just plain fortunate. As it turned out I’d say we hit the jackpot - big time!

Jaclyn was most assuredly in the ‘cutesy’ department herself. Living but two blocks from us as it turned out, she was a pert little sixteen-year old blonde, who if she could sing and dance would have had a walk-up start at the next Teen Talent pageant.

She had replied - or rather her parents had, to a hastily typed plea we had put up on the notice-board at the local mall seeking a responsible and imminently available baby-sitter. My wife Kyra and I (and without divulging my own shameful age at this juncture, let it simply be said she is yet a young woman, still a ways off her twenty-seventh birthday) have brought into the world an over-the-top beautiful little moppet by the name of Eloise - now just enrolled in middle school.

Figuring we had a few evenings’ relaxation coming to us - me having gained an Interstate transfer with better pay and my wife pulling down a Masters in Communications from NYU. - at the very least we could now afford a couple of nights out a week.

Jaclyn was a delight to have around. Attentive and courteous she would even fill the dishwasher for us without being asked. We would frequently get home to find the house tidier than when we left it. Eloise just loved her too and would rush up to the front door to hug her silly whenever she was rostered on for the night. As it was common for her to bring homework assignments to complete after she had gotten Eloise down for the night, we gave her free rein to use the computer if she needed the Net for any urgent research. Not once did she forget to say “Thanks Mr. Bailey for letting me use your puta!” as she was leaving - and usually I drove her home. They don’t churn out too many kids like this!

Whenever Jaclyn turned up, she and Eloise would disappear into the bedroom and we would see neither hide nor hair of them until it was time for us to leave. Frequently their girlish laughter would reach a higher than normal decibel level, an explanation given by Eloise later, being that “Jaclyn tickled her a lot.” I remember distinctly thinking there were areas of Jaclyn’s developing body I really wouldn’t mind ‘tickling’ myself! It wasn’t a contemplation I figured might be in my best interests to make public.

Life then was running on a supremely even keel. It took but the most innocuous of comments to bring it all undone - as it were. I had been working on the computer that night, putting the finishing touches to a budget report, when Eloise came skipping over to give me her traditional good-night cuddle. Standing beside me, she was looking at the screen and wrinkling up her nose better even than Elizabeth Montgomery could manage at her peak. Then she asked in all innocence.

“Can I see the pictures of all those girls daddy?”

Somewhat shocked, yet keen you might say, to unravel this mystery. I asked her. “What girls sweetheart?”

Eloise began giggling quietly. “The ones with no clothes on of course ... they’re naughty!”

I looked at her. “Eloise, I have no idea what you’re talking about!” I replied, “Where have you seen pictures of girls with no clothes on?”

“Jaclyn shows them to me,” she said, as if that were the most obvious thing in the world. “She finds them on your computer.”

I suppose I must have had my mouth open in dumb amazement.

“Don’t you believe me daddy?” Eloise asked slowly. “There’s heaps of them. She lets me sit on her lap while she shows me the pictures and sometimes (her eyes widened up like saucers) she tickles me while we look at them.”

I could have done any number of things. Castigate her, question her further, call out to Kate or put in a call to Jaclyn’s parents. I opted for the sleuthing option.

“That’s OK sweetheart,” I muttered, “Of course I believe you ... I’m so glad you and Jaclyn have lots of fun together ... you really like her don’t you baby?”

“Oh yes,” she beamed, “I love it when she comes over.”

Scooping her up, I carried her to bed where both my wife and I tucked her in and said goodnight.

Later, in the kitchen I dropped the bombshell.

“Kyra, you’re not gonna believe this,” I said. “I think Jaclyn has been to porn sites on our computer. She’s been showing Eloise pics of naked girls by the sound of it ... and God knows what else??”

For several seconds my wife was able to make no lucid response. Eventually, a semi-choked “What? w-w-what pictures ... where?” I think in hindsight, she could have used a double shot of black label scotch.

I told her basically what Eloise had said which served only to have her grasp a hold of the work-bench for support.

“And what does she mean, Jaclyn “tickles” her?” she asked, most likely following my own thought processes and hopefully coming up with alternate possibilities.

“I got as much idea as you hun,’ I replied, “but I figured making an issue of it in there (I inclined my head back towards the dining room) was not the way to go just now.”

“No you’re right,” she said slowly. “Definitely don’t want Eloise taking any guilt trips on board.” She was quiet for a moment. “What the Hell are we gonna do though?”

“Well firstly,” I answered, “Let’s go check the computer!”

Given that we had only upgraded to a note-book a month or so earlier, running a History check presented the simplest of tasks. Figuring out which sites she hadn’t been to might have taken longer! A little late now to be activating Net_Nanny I pondered ruefully.

“Schoolgirl whores,” “Upskirt treats,” “Truck-stop sluts,” “Cathy’s Apartment,” “Panties ‘n Pussies,” “Blonde Biker Chicks” and my personal favorite - “Hot hoes,” were but a few of Jaclyn’s forays into the world of sleaze. A sixteen-year old for Christ’s sake! Was this a thing of normality for schoolkids these days we both wondered?

Clicking the start button I selected “file search” and ran a check on simply jpg files. In less than ten seconds we had up pretty much everything that the girls must have been exposed to. I heard Kyra’s intake of breath. Mine was already somewhat erratic.

If I am totally honest though, the mere thought of Jaclyn, let alone Eloise looking at these pictures was if nothing else, unavoidably arousing in concept. I didn’t air this particular view however.

“We’re going to have to tell her parents,” Kyra muttered.

“Tell them what Kate?” I replied. “We have no proof. She would only have to deny it - which of course she would - and we’d look stupid. Besides, do you really think either of them would believe their daughter capable of doing anything like this? I wouldn’t believe it!”

“So what’s the plan?” she murmured.

“Well Kyra,” I responded slowly, “It’s quite simple really. We set up the digital camera somewhere high up on the bookshelf (I gestured towards the wall behind us) It’s got what? forty-five minutes video capability? We just have to make sure it’s facing the computer OK? No way either girl will see it between the books up there.”

With more than a hint of disquiet I sensed, my wife agreed to the strategy. She recognised first and foremost quite obviously, the need for evidence.

When setting the thing up the following evening and having made arrangements for Jaclyn to babysit, I figured one last aid to concealment might not go astray. Waiting then until Eloise was taking her evening bath, I dug out an old cook-book of absolutely no value, wrenched out everything save the cover and cutting a hole in the spine for the lens, set the camera inside. It was then simply a matter of wedging it in position and making the necessary directional adjustments. Admiring my somewhat professional handiwork, I could see a new career opening up for me in the research and gadgets division of MI5.

Hugging Eloise and giving Jaclyn her customary kiss on the forehead, we headed east on Chief street for the local theater. I don’t think either of us had our minds on the movie that night, wondering what if anything we might discover on our return.

Little Eloise was long asleep by the time we got home and Jaclyn was seated on the couch watching the last few minutes of “Elizabethtown.” Always had meant to toss that thing!

“I’ll take her back tonight,” Kyra called out, “Just wait till I get home though would you?” Didn’t take much to figure out the meaning of that one. Gave Jaclyn a last hug after helping her on with her coat and if that wasn’t a sexy little smirk she gave me, I don’t know what is.

Looking at an empty room, an unoccupied chair and nothing but the computer desk-top screen for almost twenty minutes was something less than either entertainment or incriminating evidence. Obviously the girls had been upstairs in Eloise’s “loft” amusing themselves. We were in fact about to turn the thing off when a flurry of movement heralded the arrival of Jaclyn to the computer. Quite obviously practised in her art, we could see even at this distance that she had logged into some porn site. It’s hard to miss a half-naked teenager parading her breasts (and most everything else) for the camera.

Whilst without the benefit of any sound, it was still abundantly clear that Jaclyn was calling Eloise downstairs. Kyra had grasped my arm and was studying the computer screen (we were of course re-playing the images courtesy of digital video software) with what one might term a “keen interest.”

Sitting on Jaclyn’s knee in her nightdress, Eloise made herself comfortable and within seconds, both girls were giggling and pointing at their older compatriot’s unseemly yet undeniably sexy poses.

It was at this juncture that I first became aware of certain physiological changes occurring in the area of my own crotch. I was forced to admit that the reality of watching a sixteen-year old girl and (sad to relate) my own eleven-year old daughter taking quite obvious pleasures in watching images such as they were seeing - grossly erotic! This had not been the plan.

Glancing across at Kyra, she was giving nothing away, yet I would swear I saw the onset of a blush or two as she absorbed the action being played out on that small screen.

“Oh my God,” she suddenly cried out, her hand drawn up to her mouth. My mouth at that moment had simply dried-up! We watched as Jaclyn clearly slipped her right hand up beneath Eloise’s nightdress, doing something to her that was causing the young girl to giggle madly. Whatever that might be was occurring at sub-waist level and looked suspiciously sexual.

Eloise was turning around to look at Jaclyn as if to admonish her, and for just a moment we could see plainly the older girl’s hand between our daughter’s legs. Unless I am greatly mistaken she was actually molesting her through her panties.

Whatever she was doing, Eloise certainly had no objections and as both girls now were openly giggling at a new page that appeared to be devoted solely to schoolgirls getting spanked over the knee (we were able to monitor such things by judicious use of the zoom option) Kyra’s mouth had dropped open ... from what emotion I couldn’t immediately say.

“This is unbelievable,” she finally whispered.

“Yeah - incredibly erotic too,” I added. “I’m sorry Kyra, I know I shouldn’t be saying that - its our daughter getting sexually molested there (I inclined my head towards the screen) but really, how hot is this?”

I was fully expecting her to start divorce proceedings but instead she nodded slowly before taking her eyes off the screen and softly answering,

“Yes it is - I hate to admit!”

There wasn’t a great deal more to see. A couple more websites, a lot more contact with my daughter’s panties whose giggling remained unabated throughout and plenty of gasps from my wife. Just moments before the camera cut-out we were treated to the spectacle of Jaclyn whispering something to Eloise, who quite willingly turned around and allowed Jaclyn to kiss her on the lips.

All I can say is that Kyra and I had the wildest sex that night since our courtship days - and at my age that is a major plus.

Thing is now, we had the evidence but little idea what we were going to do with it.

Well that’s actually not completely true. Rudimentary thoughts had partially crystallized but nothing I could bring myself to admit to. After all I still liked to think of myself as a responsible parent and decent member of society. Whatever demons if any, Kyra was wrestling with we never got to discuss. I think we both figured that playing it by ear was the option of choice here.

It would normally have been the weekend before we needed Jaclyn again but after consulting with my wife, we decided to bring her over that Friday evening having every intention of confronting her with our recent findings.

First thing Jaclyn did when she arrived at our place - and God, did she have to choose that night to come dressed-up so attractively? Pretty lycra top, short skirt and sexy little patent leather shoes, was to ask,

“Where’s Eloise?”

Rather than waste unnecessary banter explaining that we had left Eloise with her grandmother overnight, we simply led her over to the computer and hit the replay button.

She watched less than ten seconds before slumping into the chair and covering her face with her hands. This wasn’t so much a case of blushing as her cheeks being aflame!

“I’m so sorry,” she sobbed uncontrollably. “I didn’t mean to do anything bad ... my older sister showed me those p-pictures. I know I shouldn’t have let Eloise see them.” She was wracked by a fresh paroxysm of guilt and distress. “You’re not going to tell my parents are you?”

I knew I had to maintain an authoritative stance here.

“Your parents?” I replied sternly, “Jaclyn, its not just the porn sites, you have been ... er, how do I put this? interfering with our daughter! We really should be calling the Police over this!”

“Oh please noo,” she gushed, her young life crashing about her in perceived ruins. “Mom and dad would never speak to me again ... I’d be taken away somewhere. Please you can’t do that!”

“What made you touch her there Jaclyn?” Kyra asked suddenly. The young girl covered her face again.

When no answer was forthcoming she gently took a hold of Jaclyn’s hands and pulled them back to her lap. The tears were still in free-fall.

“Do you just like girls ... that way?” she prompted, at the same time reaching across for the tissues the far side of the table.

Jaclyn simply blushed but the nod was perceptible.

Even as she acknowledged the fact, there I was thinking to myself, “Jeeze, given the indecent fantasies I’m having just looking at that tight little skirt, wharights do I have to be accusing her of sexual mischief?”

“I’ll do anything,” she was crying in desperation, “Anything, if you just don’t call the Police or tell my parents.”

I looked across at Kyra. If she was thinking what I was thinking, she certainly was giving no indication of it.

“Well I don’t know Jaclyn,” I said, “What would you do if we started touching you inappropriately?” I winked at Kyra. “I mean, what if I were to do this?”

So saying, I leaned over her shoulder and gave her right breast a gentle squeeze.

“Don’t do that,” she reacted, pushing my hand away.

“Don’t touch your breasts?” I enquired. “But it’s OK for you to rub our eleven-year old daughter’s pussy? How’s that reasonable Jaclyn?”

The young girl sat there in silence, hands in her lap - exactly where I would have liked mine located right that moment, given the brevity of that tiny skirt and the amount of girlish leg on display.

“I didn’t mean to hurt her.” she said at last, “It was just a game.”

“Well I believe you sweetheart,” I replied, “and as long as we understand each other - why, we can keep playing it can’t we?”

Even as I spoke, I slipped both hands down past her shoulders and cupping her outrageously sexy young breasts, felt her up like a professional molester.

“Are you crazy?” Kyra almost whimpered. “You want to spend ten years in the slammer?”

“You’re missing the point hun.” I smiled across at her. “The only one with any likelihood of doing a stretch in the near future is Miss curly locks here. Who do you think the Police are going to believe? - her claims of sexual abuse or our filmed evidence of the babysitter shoving her hand into our eleven-year old daughter’s panties?”

Jaclyn stared up at Kate as if to say, “He’s got a point there!”

The real plus I was thinking is that she was no longer making any attempt to dislodge my hand and I have to tell you, the incoming sensations on offer caused by the passage of my palms across those hot little speed humps, was generating some serious steam down in the boiler room.

Just for a moment, Kyra watched with almost clinical detachment as I continued fondling the babysitter. She was definitely catching-on so far as the blackmail strategy was unravelling. Jaclyn, I must say, was either resigned to her immediate fate or was finding the ‘punishment’ anything but a hardship. She just sat there with her hands in her lap - the image of pre-programmed innocence.

“You’re not going to rape me are you?” she asked suddenly looking up at me, as if wishing to eliminate the less pleasant of possible eventualities.

“Good Lord no sweetheart,” I told her. “What you did to Eloise although hardly in the job specs, does not call for a reaction quite that drastic. Besides, you think my wife here would stand by and let me do that?”

She shook her head slowly just as I withdrew both hands from her top. Even so, I still had a somewhat enervating view of the most desirable of teenage cleavages - one that every boy from ninth grade onwards, must be angling to slip his hands down.

I aimed to pre-empt every last one of them!

“Why don’t you show us where you found all those pics you downloaded for Eloise?” I suggested. “Computer’s right there Jaclyn.” I indicated the keyboard not an arm’s length away.

“I can’t,” she replied, visibly shocked. “Don’t make me do that ... please.”

“I understand,” I replied, “Bit too embarrassing huh? No matter - I’ll do it for you.”

Before she could make a move, I leaned across, brought up the history content and clicked on “Cathy’s Apartment.” Double clicking “Enter” and there we were, right at home with teenage Cathy as she sat rather invitingly on a sofa, legs curled up under her but somehow overlooking the fact you could see a healthy wedge of floral panties beneath her dress. Right alongside - another pose. It must have been a hot day. The poor kid was trying to get cool, leaning forward to get some fresh air down her top, both breasts displayed to the very edge of decency. Lucky she had on a tight bra reining in those burgeoning assets.

Image three and she seemed to be giving up any and all pretence of a refined upbringing. The dress had magically vaporised and she was doing a piss poor job now of covering up her panties with her hands.

Kyra I noticed was, if not riveted to the LCD screen, paying remarkably close attention to the items displayed there-in. Jaclyn herself was blushing rather attractively, but making no attempt to extricate herself from the slide-show either.

By the fourth picture, young Cathy had decided to stretch her legs - rather long slim ones I noticed. Having nothing better to do it seems than incline herself across the edge of a conveniently nearby table, her floral knickers were now displayed with crystal clarity, along with the barely concealed cleft of her admittedly yummy little rear end.

Not sure whether it was the picture which dictated my urge or it just seemed like a good idea at the time, but my hands I noted had returned to their former resting place - across Jaclyn’s soft and pliant young breasts. I don’t think Kyra was even looking!

Image five displayed Cathy well into slut mode. Her left breast completely free of that tight little bra and the other in transit, she was tugging aside her panties, partially for the benefit of the camera lens and equally to facilitate the introduction of her middle finger to an evidently blow-dried and coiffed little pussy.

“Getting warm girls?” I enquired of the on-site if not captive viewing audience. The physiological condition of my own procreative equipment really doesn’t bear comment.

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