The Weekly Shop
by Ashley
Copyright© 2024 by Ashley
Erotica Sex Story: Jessica, divorced mother of two, is doing the weekly shop when she finds her mind thrown back to her teenage years by the sight of a young boy's erection. She'd thought that it was long forgotten, but it seems her body still remembers.
Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa Consensual Heterosexual Fiction Double Penetration First Masturbation Oral Sex Petting .
Jessica is doing the weekly shop. It’s a chore that she never looks forward to after a hard week at work, but it has to be done. At least she gets off work early on a Friday, so it doesn’t waste the whole afternoon.
She walks up and down the aisles, filling the trolley pretty much on autopilot, until she gets to the check-out. There’s a young boy doing the bagging. She doesn’t pay too much attention to him to begin with, just noting that he appears to be a bit young to be working in the store. She’s unloading her items from the trolley and he’s putting them into bags as they come off the belt.
She’s about halfway through when she notices something: the bulge in the young boy’s jeans. It’s only then that she realizes that, as she’s bending over, her blouse is gaping and he’s staring down the front of it, getting an eyeful of her boobs. She’d been in a hurry that morning and had picked out the first white bra that came to hand to wear under the thin blouse she’d selected. It was somewhat more revealing than she normally wears to work and she knows that he’ll be getting a very nice view indeed of her lightly enhanced, C-cup breasts.
Jessica feels a sudden warm surge of lust at both the sight of his erection and the knowledge that she still has the ability to turn a young boy on. She peeks up at him and guesses that he’s probably about fourteen or fifteen, just beginning to put a little muscle on, but still with a delicious innocence. He has a mop of unruly, dirty-blonde hair and the cutest face with sparkling blue eyes.
He catches her looking and smiles at her. Jessica smiles nervously back but can’t make eye contact: her eyes would give away her sudden desperate need.
As she carries on emptying her purchases onto the conveyor, she can see the effect of her display as his bulge gets bigger and the shape of a small but hard shaft becomes obvious. Jessica’s clit swells and tingles at his obvious excitement, and she remembers the last time that she saw such a beautiful sight.
Jessica had only been seventeen herself when it happened, almost half her lifetime ago. She’d been babysitting him as a favor for her parents. He was a very cute little boy, only just fourteen but even so he was a handful, demanding first snacks and then that she sit with him on the couch and play video games. It was all innocent enough and then her phone had pinged with a text.
“Is that your boyfriend?” he asked, picking it up from the table. Jessica didn’t have one at the time but nonetheless didn’t really want him reading her messages.
“Give it back, please Jimmy,” she asked, trying to keep the annoyance out of her voice.
“Shan’t,” he said, chuckling and holding it above his head. As she reached up to try to grab it, he’d tickled her ribs with his other hand. She was very ticklish and as soon as he heard her almost hysterical giggles he lost interest in the phone and attacked both of her armpits mercilessly.
As she wriggled and squirmed, attempting to get away from his prying little fingers, he pursued her and, in the thrashing mess of arms and legs, he kept managing to put pressure on her pussy. Nothing blatant, just a thigh here and a hip there, and the occasional brush against her suddenly hard nipples. Her uncontrolled giggling began to give way to hard breathing as she got increasingly aroused.
She was sure it was unintentional, but somehow his thigh ended up between her legs, rubbing directly on her pussy. The more turned on that she got, the less energy she seemed to have to fight him off, until she was just lying there with his leg stimulating her clit. When she finally called mercy, dangerously close to cumming, he rolled away and her eyes caught sight of the lump in his shorts.
She kept trying to look away as they caught their breaths, but her eyes kept being drawn back. Little Jimmy must have noticed because he put his hand on his upper thigh and began to stroke the end of the bulge with his thumb.
Poor Jessica was entranced: she was sure it was just all the endorphins and oxytocin flooding her brain, but she just couldn’t stop watching him.
Then he reached for the button of his shorts.
“What are you doing, Jimmy?” she asked, her voice quavering.
“You want to see it, don’t you?” he asked, undoing the button and grasping the zipper. “I can see that you do.”
“You mustn’t,” she said, but there was very little conviction in her voice. She breathed in sharply as he drew the zip down and she saw his white briefs.
“I don’t mind,” he said amiably.
Her mind was a mess: If I don’t say anything, that’s not agreeing ... is it? Her clit was tingling like mad at the thought of seeing him, and her pussy clenched hard as he lifted his hips off the couch and pushed his clothes down to his knees.
She held her breath as the anticipation of seeing her first penis made her tremble. Not that she was a virgin. About a year earlier she’d increasingly come to feel like an outsider while talking with her friends who had ‘done it’, and her virginity had become something that she just wanted to be rid of. She even put herself on the pill beforehand so that there’d be less risk and less stress. On the big night, there’d been some kissing (which was lovely), but then Greg had gotten overexcited. After putting his hand up her skirt and then down her panties (which again had been lovely if woefully brief), he’d pulled them off and laid down between her legs. She was nowhere near aroused enough, and never even saw his penis, let alone touched it. She had no real idea what or how big a thing was pressing against her virgin pussy. It had been an unsatisfactory, somewhat painful affair, mercifully short because Greg most certainly had been aroused enough.
She just stared when Jimmy’s cock came into view: it was so, so gorgeous: about four inches long but thicker than she’d imagined, and so, so hard. The tip was just peeking out from his foreskin, a small disc of shiny reddish skin. And below, tight and almost hairless, his sweet little ball sack.
He grasped it near the tip between two fingers and thumb, and she moaned softly as he drew the foreskin back and his darling little knob came into view.
“You can touch it, if you want,” he told her, his fingers moving gently up and down. She was so turned on, and she wanted to so, so much. Surely one little stroke couldn’t hurt?
She reached out and gently brushed a fingertip along the shaft, marveling at how hot and silky-smooth it felt. Then Jimmy took his hand away and her finger continued to move back and forth. One finger was joined by a second and then more until her hand was wrapped around it, and she could feel its hardness and adore the way it twitched and jumped under her caresses.
She desperately wanted to kiss it and to lick it, to know what that tight skin would feel like on her lips and tongue. She dragged her eyes away to look up at his face and his expression was one of pure pleading. She kept her eyes on him as she leaned slowly forward and a wide grin spread across his face as he realized what she was about to do.
She was telling herself that it would be just a little kiss, but it wasn’t: as soon as the tight skin of the tip touched her lips, they just opened up and her tongue wrapped around it as her hand stroked up and down the shaft. She was hooked, both by the gorgeous feeling of it, and the cute whimpering noises that Jimmy made as he frantically pumped his hips at her while gently stroking her hair.
Jessica loved the feeling of power and control she had, so very different from that time with Greg. Her clit felt swollen beyond anything she’d ever known, and her vagina felt engorged and wet with arousal.
Her hand went between his legs and she tickled his tight and almost hairless little balls and he thrust his cock deep into her mouth, just tickling the back of her throat, before he shuddered violently and her mouth was flooded with a creamy, thick, and slightly salty liquid. It was her first ever taste of boy-cum, and she found the taste ... not unpleasant, but the idea that this was the stuff that babies were made of was thrilling, and she loved it. Jimmy was making the sweetest little keening noises as he convulsed five more times, each accompanied by more lovely cum.
She couldn’t stop, holding it in her mouth and caressing his little balls long after he’d gone all soft. It was only then that she slowly realized how intensely aroused she was: her clit swollen and throbbing, her nipples hard and achy, her panties soaking wet with her juices, and, most of all, the almost painful need to have something filling her vagina.
Then he began to swell in her mouth again and the feeling of emptiness between her legs got even stronger. She slid a hand down and pressed hard on her clit.
“We can ... fuck, if you want,” Jimmy said, surprising her. She did want. Her mind was full of imaginings of how his hard penis would feel inside her.
“What do you know about fucking?” she asked, stalling for time.
“I know a bit,” he answered. “I know that this,” nudging her lips with his erection, “goes in there,” nodding to the hand covering her pussy.
“Would you like to do that?” she asked, half hoping that he’d say no, but a bigger half praying he’d say yes.
“Very much, Jessica. Can we? Please?”
She knew that she wasn’t thinking straight, but she’d already given him a blowjob ... but she needed it so, so much. As she pushed her panties down until they were dangling from one ankle, he was off the couch and between her legs in seconds.
She could scarcely breathe as he nudged a couple of times in the wrong place before she reached down and placed the tip at her entrance. His hips thrust, and she moaned softly at the exquisite sensation of him sliding inside her.
It felt so, so right. It was beautiful. It was gorgeous. Her head swam as he frantically pumped his trembling cock in and out of her. She pushed her T-shirt and bra up so that she could get at her nipples that were crying out for attention, and he ground his hips on her, trying to get every last ounce of lovely, lovely friction and making his cock swirl inside her, stimulating every nerve ending in her young vagina.
His cum, flooding her pussy, was the trigger that set her off, and she pulled his hips tight against her as her cunt crushed down on his spasming cock, her legs thrashing wildly as the first wave hit her. It was a body-shaking, eye-rolling, heavenly climax, spurred on by the way his ejaculating cock seemed to be almost vibrating inside her.
Unfortunately, it coincided with Jimmy’s parents returning home unexpectedly early. They were remarkably understanding, all things considered: his father lifted young Jimmy away and ushered him upstairs, leaving poor Jessica trembling and half-naked. Jimmy’s mom, possibly misunderstanding the whimpers coming from the girl, put her arms around her trembling shoulders. “Oh, you poor thing,” she said soothingly, stroking her hair, seemingly oblivious to the tremors that were still rocking her young body.
Jessica was in such a dazed and confused state that Jimmy’s mom had to help her dress, whispering calming nonsense into her ear, before driving her home.
She only realized later how close she’d come to absolute disaster, her life in ruins. From his parent’s reaction, it was clear that it wasn’t the first time that Jimmy had been caught ‘playing’ with a babysitter. Understandably, Jessica had mixed feelings about the whole thing.
She never forgot the intense pleasure that little Jimmy had given her, but rationalized it as simply as her body’s reaction to what was, in reality, her first real lovemaking. It had never really occurred to her that her later experiences never quite matched up to it.
It is those memories that flood through Jessica’s mind as she glances furtively at the young boy’s hard-on. Her clit is almost instantly hard and she can already feel wetness building up inside her. She nervously pays and is about to wheel her trolley out when a guy who’s probably the manager walks up. “Help this lady out to her car with her groceries, then you can go, Adam.”
“Sure, Mister Jeffries,” Adam says and smiles again at Jessica before taking charge of her trolley. She follows him out to her car, his firm little butt cheeks doing nothing to ease the tingling in her groin. It doesn’t help either when his jeans stretch over his firm ass cheeks as he puts the bags into her trunk.
Picking up the last one herself, she adds it to the rest and then gasps as she feels him brushing against her ass, his hardness nestling between her cheeks.
“I think you missed this,” he whispers, his face right next to her ear. How the fuck does he know that? Jessie thinks frantically as his cock drives her crazy with lust. He hands her a lemon that must have escaped from its bag. Ah! Of course, that’s what he meant! But it’s too late - poor Jessica is already panting with desire.
“I could help you unload as well, if you’d like?” he suggests.
She knows that she shouldn’t. A small, still rational part of her mind reminds her that Peter and Anthea will be back from school in a couple of hours. A different part, a more primal part, reminds her what a young boy could do for her in an hour.
“That would be lovely ... er ... Adam.”
“No problem,” he replies, his smile now a fully-fledged grin. “Wait here, I’ll be back in five, Ma’am.”
“Jessica,” she says, her voice high and nervous, like a schoolgirl’s. Although a schoolgirl whose panties are now a sodden, and no doubt fragrant mess.
As she stands in the car park, she begins to lose her nerve. What if she’s caught again? She’s just come to the decision that she’ll tell him that she’s changed her mind, when he comes back with another boy in tow. He’s also blonde, about the same age, and is the spitting image of Adam.
“This is my brother, Noah,” Adam says. “My twin brother. He wants to help.”
They both smile at her and her mind races. Sweet Jesus, two of them!!
“How old are you, boys?” she asks, trying to sound casual.
“Fourteen,” they respond, almost together.
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