Babysitting the Babysitter - Cover

Babysitting the Babysitter

Copyright© 2021 by Peter Pan

Chapter 2: Highway to Hell

Erotica Sex Story: Chapter 2: Highway to Hell - 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  

BABYSITTING THE BABYSITTER: HIGHWAY TO HELL

An almost uneasy silence befell the three of us. One is limited conversationally you can appreciate, having - in company with your equally depraved wife - just rounded up a tour of duty, sexually dealing with a sixteen-year old schoolgirl for the past hour or so.

Watching the young girl get dressed however more than made up for the lull in interactive dialogue. Kyra I noticed, was not reticent in helping Jaclyn back into her flimsy little bra. Certainly my own talents are more geared towards the removal of such items.

“Will you need me to sit Eloise next week?” Jaclyn asked, smoothing down her skirt, quite as if she had just cleaned up a plate of cookies with her glass of Pepsi. Well If that wasn’t a glint of utter satisfaction in her cheeky little face, I don’t know what was.

“Matter of fact Jaclyn,” I grinned at her, “We might just take you up on that offer.” I looked across at Kyra. “Aren’t we scheduled to have dinner with the Pattersons next Friday?” Still in seeming denial of the last hour or so, she managed but a nod.

“Well there you are sweetheart,” I beamed. “We’ll see you back here 6.30 pm Friday ... right?”

I glanced across at Kyra. “Can you take her home hun, got a few database edits I just have to get finished for a client by the morning.”

“Oh ... y-yeah - sure,” she stuttered, recovering a degree of composure as she collected her car keys from the rack by the front door. “You ready Jaclyn?” she asked, turning to the girl.

Handing me a smile designed to send my hormonal regulators into meltdown, she merely said,”Goodnight Mr. Baker.” It was way less than her body language conveyed.

I had barely set up the editing screen when I heard Kyra pulling-in to our rear driveway. A transmission in its death agonies does have its own aural signature.

“Do you think she’ll say anything?” Kyra asked nervously, standing behind me with her hands on my shoulders.

“You mean other than “Do I have to go home now?” I suggested.

“Be serious just for once,” she chided.

“Look Kyra,” I replied, “We have a full-length video of her rubbing our young daughter’s pussy every which way for God’s sake. You think she’s gonna risk anyone finding out about that? No she won’t be telling her parents – trust me. Besides, it’s our word against hers.” Then glancing towards the bookcase behind us, “and also, I hardly think her starring role in that in-house porn movie we just shot, is gonna help her case any, do you?

“I’m just worried,” she replied softly.

“Me too,” I countered, “worried she might not turn up next Friday.”

“You’re disgusting,” Kyra muttered.


The week in fact seemed to slow-up as Friday approached. Following a late snowfall, I had Kyra ring Jaclyn’s place to see if she needed picking-up but evidently she had already set out on foot.

We were just clearing away the last of Eloise’s dinner plates, when I noticed through the dining-room windows, Jaclyn climbing the steps gingerly to our porch.

“Hi sweetie,” I said breezily. How cute did she look right at that moment with flakes of snow in her hair and a flushed little face brought on by the chill. I relieved her of her coat, wanting desperately to relieve her of so much else. Judging by her expression, I figured she’d worked that out for herself.

Eloise was out of her chair and hugging her already. Instantly, images of her being “tickled” stupid resurrected themselves on the re-play screen. What were the odds of it happening again tonight? I wondered. I’m sure Kyra was tossing around the same ponderance.

“Ok Eloise, now you can stay-up with Jaclyn till 7.30. OK?” I told her. “But I want her up in her room and asleep by eight at the latest Jaclyn.” I added, emphasising the point with a nod up towards her bedroom loft.

“Sure Mr. Baker, I’ll make sure she is.” Jaclyn replied, at that moment the very image of respectful compliance.

“Opening my arms to her, Eloise ran over and hugged me. “Goodnight daddy, see you in the morning.” Still in her school uniform she looked the image of girlish innocence – which of course was exactly the case.

Hugging her mom she then took Jaclyn’s hand and began dragging her to the stairs, intent I imagine on showing her something in her room she had most likely made during craft that afternoon.

As we negotiated access to the rear laneway Kyra looked across at me. “You think Jaclyn will “do” anything to her while we’re out?”

“Nothing that’s gonna leave a lasting impression anyway.” I replied smiling. “Given the photographic evidence my sweet, I’d say she’ll play it pretty straight for a while.”

“Hope you’re right.’ She murmured. I figured it best not to elaborate upon my preferences right that second.


Maybe the Pattersons’ roast hadn’t quite arrived at the cutting edge of culinary grandeur. Perhaps my mind was on other things, but either way I found the conversation that night to be as boring as the food. Thus using the completely true (as it happened) yet double-edged escape clause, “Hey guys, we promised the baby-sitter we’d be back early” we took our leave at 9.45. Kyra almost beamed at me I noticed.

“Oh you’re back already?” Jaclyn smiled up at us from the lounge in the TV room as we filed in the front door. The words were certainly not tinged with any regret that I could detect. Sitting there in her school-dress still, hands folded demurely in her lap, she looked far tastier than anything recently on offer at the Pattersons’ dinner table.

“Would you like a soda or some other drink Jaclyn?” Kyra enquired as she headed for the kitchen. I sat down alongside the girl. She was watching Spielberg’s Gremlins of all things.

“Could I have just a Sprite please?” she called out to my wife. Another of those wonderfully hot little smiles fed my ego no end.

“That’s a pretty old movie sweetheart,” I said to her. “Way older than you even ... getting on for ten years before you were born can you believe?”

“I know,” she giggled, “But I’ve always wanted to see it and you have so many dvds here.” In truth, well over three thousand as there are, she definitely was on track with that comment.

Watching intently as Stripe and his followers were conspiring to give Phoebe Cates a veritable night of hell behind the bar, I studied Jaclyn’s somewhat cute changing expressions. Whether sexually motivated or just plain protective an action - I really couldn’t volunteer, but slipping my arm around her shoulders at that moment achieved two things. Having the young girl react by snuggling into my shoulder and secondly – a desire to slip my arm around other things.

I might have prolonged such contemplation had she not suddenly inclined her face towards me, making it fully obvious she wanted to be kissed. One does not wallow in self-doubt at such times. Better even than short-term memory recalled, her lips were sweetness incarnate.

With the practised efficiency of one many years her senior, she swung herself, quite without warning, across my knee, ending up in a seated position on my lap, both arms around my neck and barely missing a beat so far as that under-age but over-needful mouth was concerned. That trace of girlish perfume was no traitor to her cause either, in fact coupled with the sensation of her compact little rear-end up against my crotch now, I was feeling decidedly squirrelly.

Placing my arms around her waist, I allowed both hands to drop marginally to encircle her bottom. The good news was – she allowed it too! Barely had I pulled her to me, when the front of that school-dress began to provide a fully indecent view of areas of her anatomy no sixteen-year old should have on display. She giggled seductively as she picked-up on my line of vision...

“You’re being naughty Mr. Baker,” she whispered, leaning inwards even further. If my hands hadn’t been so taken-up with fondling her rear cheeks right that moment, I would have given both those hot little breasts a gentle squeeze.

“Jeeze Noel, I leave you alone for barely two minutes and you’re full-on misbehaving.” Kyra was posed in the doorway, drinks in hand.

Having in mind to plead the innocent bystander, I realized swiftly that any such defense strategy would be destined to failure, so instead, I lowered my face from Jaclyn’s and kissed her right breast which brought forth a couple of gasps. One from the young girl, the other from Kyra herself as she sank down on the couch beside us.

Having no more than to whisper in her ear and Jaclyn compliantly manoeuvered herself on to her knees so that she was straddling my lap, facing me. Having unfettered access now, I slipped a hand up beneath the hem of her dress and sought-out the warmth between her slim thighs.

Whatever Phoebe Cates was up to on screen behind us – be assured no-one was interested.

Feeling my way higher, the back of my hand brushed the front of the young girl’s panties which caused her to wriggle her hips and sigh gently. Smoothing my hands across her bottom I pulled her yet closer and kissed her with a passion that is usually reserved for more established partners.

In line with my own burgeoning desire, Jaclyn was beginning to breathe hard and to wriggle about on my lap in what could only be termed a suggestive manner. Again I located the front of her panties and began tracing that hot little cleft down between her legs with my middle finger.

Rubbing her there through the soft material I could feel her thrusting hard up against my fingers with her hips. What was happening between my own legs would have been no less obvious to her than it was to me.

“Take her panties off.” issued from Kyra’s lips. Glancing across at my wife, the reason for so undiplomatic a request was immediately obvious. Her hand deep inside her own undies, she was rapidly closing-in on the world record for a self-induced orgasm.

Wishing to avail her of every opportunity for success here, I tugged Jaclyn’s dress up and grasping the waistband of her tight little knickers peeled them downwards. It took but the slightest co-operation on her part to slip them past her knees and then off one ankle ahead of the other.

Able now to separate her labia and to softly finger her the length of her young pussy she was trembling with what must have been a mixture of real-time pleasure and first-time trepidation.

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