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Jessa Stories
© 2019, 2021, 2023, 2024 All These Roadworks
The author asserts their right to be identified as the creator of this work under the name “All These Roadworks”.
All images in this book, including cover art, were created by All These Roadworks.
All characters in this story are fictitious. Any resemblance to actual persons, living or dead, is purely coincidental. All characters involved in sexual situations are intended to be aged 18 years or over, and any implication to the contrary is an unintentional miscommunication.
The events and themes presented in this story are for the purpose of erotic fantasy. They are not intended to depict actual events that have happened, or should happen. The author believes firmly that real sexual relationships should only occur between consenting adults, and be built on the principles of respect, communication, honesty, and risk-aware enthusiastic consent.
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Table of Contents
Foreword
Introduction – The Jessa Stories
Alice and Jessa
Alex and the Slut Tax
Jessa’s Wife
Jessa’s Bible Study Group
Jessa’s Christian Single Mothers Circle
Jessa’s Church Advice Service
Jessa and the Wedding
Jessa Saves The Town
Bonus Story: Small Town Gyno
Bonus: Jessa’s Morton Valley Infographics
It’s a fantasy, not an instruction manual.
The stories collected in this volume are kinky fantasies. It’s normal to fetishise the forbidden. It can be a healthy way of processing trauma or frustration from our daily lives. It can be fun, satisfying, and exciting. Don’t feel ashamed to enjoy them.
But it’s the responsibility of everyone – and particularly people with these fantasies – to work to create a world where everyone – and, specifically, women – are safe, respected, and able to indulge their sexuality without shame or fear, whether that means consensually engaging in wonderful fucked-up kink, or living their entire life without ever encountering it.
Satisfying, sustainable kink can only be built on a foundation of firm respect for boundaries, respectful communication, and positive, explicit, enthusiastic consent. That’s a world where everyone kinky will find it easier to find partners and hook up for the interactions they enjoy, and where those who aren’t interested won’t be bothered – and that includes people who might be interested, but not now, or not under these conditions, or not with you.
Don’t let your kinks be your politics.
If you don’t already have anyone to share your kinks with in real-life, get involved in your local kink scene. Join an online community. Be polite, ask what the local rules are, listen to people who know what they’re doing before you go charging in yourself, introduce yourself and be prepared to make friends before you make partners. Confidence is sexy; not being able to hear a “no” is not.
I’m not your manifesto, and I’m not anyone’s plan for a functional society. Read, enjoy - and then go out and be fantastic, safe, respectful kinksters.
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Speaking of which – if you obtained this document without paying for it…
Writing takes time. It’s easier if I’m paid for it. Please consider visiting my website and leaving a tip; buying this story collection or a different one; or subscribing.
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When I wrote the first Jessa story (Jessa’s Bible Study Group), I didn’t realise she was going to be a recurring character.
But she must have been on my mind, because then I went and wrote Alice and Jessa, which *also* featured a girl called Jessa who likes corrupting Christian Girls, without realising I’d already had a character like that.
Thanks to financial supporters who enjoyed those tales, the Jessa series now includes nine stories – enough to fill a collection!
The first three stories included here – Alice and Jessa, Alex and the Slut Tax and Jessa’s Wife – describe a younger, school-aged Jessa, while the remainder describe an older Jessa who travels from town to town getting involved in church communities.
It’s possible there will be more Jessa stories in the future – perhaps enough to fill another collection.
I hope you enjoy these ones.
Pretty, young Alice believed deeply in what her church told her about love and sex. She was going to save herself for marriage, and the first man she had sex with was going to be the first man she married.
But like many repressed young girls, she found herself in the orbit of friends who were not quite so pure. In particular, Jessa Brown was what Alice’s mother might have called “a dangerous little slut”.
Jessa was always teasing Alice about her chastity. It seemed to fascinate her, that Alice didn’t want to fuck a dozen men each month, that she was honestly going to save herself, and only be with one man in her entire life.
Jessa was *not* saving herself. She had fucked her way through half the school by the time she and Alice became friends. She was outspoken, and sexual, and Alice gained a vicarious thrill from hearing about her exploits. Alice may be saving herself, but it didn’t mean she couldn’t hear about what her friend had been up to, and feel a pleasant little tingle between her legs as she thought about it.
She felt a little less comfortable with Jessa, though, when her friend started fucking Alice’s oldest brother, Joel. Alice had seen the way the men in her family looked at Jessa when the attractive big-titted girl visited, so it shouldn’t have surprised her, but it was still disconcerting to lie awake at night listening to Joel’s grunts and Jessa’s moans, and knowing that her brother was cumming inside her best friend’s pussy.
But then Jessa moved on to Alice’s *other* brother, Dean. Alice was scandalised.
“Did you break up with Joel?” she asked. “How could you do that to him?”
“Oh, no,” said Jessa, laughing. “I’m still fucking Joel. He doesn’t care who else is using my pussy, as long as he gets his turn.”
Alice couldn’t look at her friend now without imagining both her brothers ploughing the girl’s wet cunt – which, honestly, made her a little wet to think about. It was a strain on their friendship.
But the final straw came when Jessa started fucking Alice’s *father*.
“Jessa, how could you?” shrieked Alice, in the privacy of her bedroom, when she found out. Her mother was out of town for a church conference, and Jessa had somehow wiggled her way into Alice’s father’s bed and brought her father to a series of very satisfying orgasms.
“Oh, calm down,” said Jessa. “And yes, your father has a very enjoyable cock, in case you were wondering.”
“He’s *married*, Jessa! You made him cheat on my mother!”
Jessa giggled. “Trust me, no one *made* him do anything. He’s expecting me to do it again tonight, after it gets dark. He thinks you don’t know, and he doesn’t want your brothers to find out. I’ll just climb into bed with him, in the pitch black, and slip his cock into my pussy….”
Alice couldn’t hear any more. She slapped Jessa.
Jessa’s smile turned into a frown. “Well, that makes this even easier,” she said.
“What? What do you mean?” asked Alice – but then cut off as Jessa leapt at her.
Alice struggled, but Jessa was fitter and stronger. Soon she had Alice pinned to her bed. She pulled something off her bed, and Alice saw it was handcuffs. Alice struggled, but soon her hands were cuffed to the head of her bed.
It was only now that Alice thought of yelling, but suddenly something was stuffed into her mouth – something black and lacy. Her eyes widened. It was a pair of Jessa’s panties. And – there was something wet on them. Was that her friend’s pussy juices? Or… perhaps traces of her father’s cum? Was she tasting her own father’s cum? She tried to yell, but the underwear muffled her.
“Oh, shut up,” said Jessa. She was pulling off Alice’s skirt now, and then pulling down Alice’s panties. Alice tried to kick her legs, but Jessa had a good hold on her. She blushed bright red. She couldn’t believe this was happening. Why was Jessa doing this? Oh God – her pussy was bare in front of her best friend. What if someone came in? What if her father or brothers came in? And why was the thought of that making her *wet*?
Once Alice’s cunt was bare, Jessa secured Alice’s feet to the base of the bed, spread wide so Alice couldn’t close them or protect her pussy.
“Okay,” said Jessa. “I’ve been obsessed with your stupid virginity ever since I met you. I’m not super into girls, but I couldn’t stop thinking about how much your chastity meant to you, and how *hilarious* it would be for you to have that taken away.”
Alice made a muffled noise of protest and betrayal.
“And I decided,” said Jessa, “that seeing that happen was worth more than our friendship. You’re a good friend, Alice, but you’re such a god-damn gorgeous *victim*.”
She opened her purse and took out something – six condoms, each tied off at the end, and full of white liquid.
“I’ve been feeding you fertility drugs for the last month, Alice,” said Jessa. “Since your brother first hit on me, and I came up with this idea. And I know you don’t take birth control because you’re such a good Christian, and I know this is the most fertile part of your cycle.”
Alice didn’t like where this was going. She struggled against her bonds.
Jessa untied the first condom. “This is your brother Joel’s cum,” she said. And she turned the condom upside down over Alice’s pussy, and the sticky white fluid dripped onto Alice’s groin.
Alice went wild with horror, bucking and yelling, but to no avail. Jessa just smiled, and then used her finger to begin pushing the cum up into Alice’s pussy. Alice moaned as her cunt was penetrated by another human for the first time in her life. She felt disgusting and sinful. That was a woman’s finger – and her brother’s cum – going into her sacred, chaste vagina. She wanted to cry.
She also kind of wanted to buck her hips against Jessa’s finger, which felt so *good*…
“Here’s some more of Joel,” said Jessa, pushing a second condom of cum up inside Alice. “And these two are Dean,” she continued, forcing two more condoms of sperm into Alice’s pussy.
Alice was moaning now in time to every thrust of Jessa’s finger.
“And last of all, these are your father,” said Jessa. The cum from one of the condoms was still warm. As Jessa pushed it into Alice’s pussy, something strange happened to Alice – a wave of pure pleasure rolled through her, leaving her twitching and weak. She had had her first orgasm. She wanted to die of shame.
“There you go,” said Jessa. “All impregnated by your family, like a good little slut. How are you going to explain it?”
Alice *did* start crying, then, sobbing into the underwear gag.
Jessa took out her phone and set it up pointing at Alice. She set it to record, then said, “Here, I’ll help you clean it up.” She leaned down between Alice’s legs, and then, to Alice’s horror, began licking Alice’s cunt.
Alice tried to pretend that her first experience of sex was not a lesbian one. She tried to pretend she didn’t enjoy it. And, after a few minutes, she tried to pretend she wasn’t orgasming from her best friend’s tongue.
Jessa laughed as Alice came, and then turned off the phone. “And now we have a nice little film of you cumming from lesbian sex, to show your church group,” said Jessa.
Alice tried to beg Jessa not to show it to anyone, but she was still gagged.
“So,” said Jessa. “If you’re a good little girl who doesn’t want to be a slut, I can just leave now, and you can try and explain to everyone that you’re not a lesbian and that you don’t know how you got pregnant. Or, I can help you out.” Alice was making muffled noises, so Jessa added, “Sssh, quiet now,” and then took her gag out of her mouth.
“Please,” said Alice. “Please.” She didn’t know what help she expected, but she was desperate. She couldn’t believe this was happening to her.
“So if you want me to not show anyone the video,” said Jessa, “I want to see nice chaste Alice have the dirtiest, most taboo sex she can have. Your father is waiting for a naked girl to fuck him tonight. The lights are out. He won’t see who it is. All you have to do is go into his room, nude, fuck your own father, and then come back and show me his cum leaking from your pussy. And then I’ll keep the film to myself.”
“No!” said Alice. “I can’t! That’s so wrong!”
Jessa shrugged. “Suit yourself,” she said. “And as to the baby – well, maybe I got you pregnant and maybe I didn’t. And I bet you’d like to be able to tell yourself that that baby *isn’t* fathered by your own blood. So I’ve got a list here of ten guys you know that would like to fuck you. Just say the word, and I’ll set up a gangbang. You still won’t know who the father is, but it’ll be like a 10 in 13 chance that it’s not a relative, and that’s good odds. Which one you marry is entirely up to you.”
Alice thought about it. Jessa watched her – and when Alice finally closed her eyes and started to sob, Jessa knew that Alice had made her decision. She untied Alice from the bed.
“Good girl,” she said, and kissed Alice on the lips. “There’s a good girl. I’ll make the calls to let your friends know they can rape you. Now be a good pregnant Christian teenager, and go fuck your daddy…”
There was nothing Jessa liked more than ruining the lives of silly, innocent Christian girls. She loved how repressed they were, and how humiliated they were by doing the slightest little slutty thing. She had spent her final years of education transferring from school to school, and seducing, raping, gaslighting and blackmailing pretty young church girls into degraded cum-guzzling sluts.
Alex was *easy*, even for Jessa. She was cute, shy, and obviously repressing the fact she had sexual fantasies about fucking girls. Jessa befriended her, flirted with her, teased her, and within two weeks she had Alex naked in her bed, where Jessa licked her pussy until Alex reached a loud, humiliating orgasm.
She loved the expression on Alex’s face afterwards when Jessa revealed she had filmed the encounter, and played it back for Alex’s enjoyment. Alex obviously wanted to die, and Jessa had to hold her still to make her look at the whorish, vacant look she was displaying on the film as Jessa ravished her cunt.
“Just think what your parish priest would say if he saw this,” Jessa said teasingly, and although she never made any more explicit threat, she found after that that Alex would ultimately give in to all of Jessa’s suggestions from that point onwards.
Jessa’s first suggestion was that she should visit Alex’s house – a *lot*. Soon Jessa was visiting Alex for dinner five nights a week, and sleeping over most of those nights. Alex lived with her father Donald, her mother having passed away when she was young, and Jessa and Alex acted like perfect chaste Christian friends in front of Donald. When they were alone in Alex’s room, of course, Jessa would routinely strip the poor girl naked and force her to lick Jessa’s pussy while masturbating herself to the edge of orgasm.
She never let Alex just orgasm straight away, though. She would always remind Alex she was a lesbian slut, and tell her she had to pay the “slut tax” before she could cum. This was always some minor embarrassing task. The first time, she sent Alex to run nude to the backyard and bring Jessa back a leaf from the tree that grew there. The second time, she had to do the same thing, but with two fingers up her cunt the whole way.
That second time, Alex was spotted by her father, and she sprinted back to her bedroom, bright red with shame, without explaining. Jessa laughed when she made Alex cum after this, and teased her that she was cumming from exposing herself to her own father.
Alex protested so hard and so violently at this suggestion – she almost kicked Jessa out – that Jessa decided to double down on it. So two nights later, the “slut tax” was that Alex had to put her panties and bra back on, and go kiss her father goodnight – on the lips.
Alex wouldn’t do it, at first, so Jessa showed her how she’d been taping all their subsequent sexual marathons, and wondered what sort of a sermon the parish priest might give if he knew there was a lesbian slut in the congregation, and whether he’d refer to that girl by name…. and Alex, defeated, did as she was told, going out to kiss her somewhat surprised father on the lips, in her underwear.
After that, Jessa made it a routine for Alex to kiss her father goodnight on the lips – and a week later, specified that she had to use her tongue. When she first felt her father starting to get an erection as she kissed him, she came back to Jessa crying, but Jessa just kept licking her cunt to orgasm after orgasm until she stopped.
In the meantime, Jessa kept charging the “slut tax”.
“Go and masturbate sitting on the toilet naked with the door open until you’re about to cum. Don’t stop even if your father sees you.”
“Go into the kitchen naked and put every spoon in the cutlery drawer into your pussy, then put them back without washing them. I’m going to enjoy your blushes at dinner tomorrow.”
“Write a one-page story about how you want your daddy to fuck you. Tomorrow at dinner I’ll go hide it in your father’s room somewhere, and then after he goes to sleep you can go in there naked and try and find it in the dark, while constantly masturbating, without waking him up. Or you can just leave it there for him to find.”
“I think your dad’s watching TV in the lounge room right now. Put on your shirt, and nothing else, and go sit on his lap and tell him that you love him.”
In the end, Alex could see where this was going. Jessa was going to end up making Alex fuck her father, or cockteasing her father into raping her. She came to Jessa in tears.
“Please, stop,” she begged. “Please, I’ll do anything. I’ll be your pussy slave. Just don’t make me fuck my daddy.”
Jessa considered. She was pretty sure that Donald was already fantasising about his daughter, and she thought it was probably only a matter of time until he fucked Alex, even if Alex stopped slutting around immediately. So she had nothing to lose, really.
“All right,” she told Alex. “You’ll still need to pay the slut tax whenever you want to cum, but I’ll stop making it involve your father, on one condition.”
“What?” asked Alex.
Jessa smiled. “You need to go out and seduce and blackmail one of your girlfriends at school, just like I did with you. And you need to make her fuck *your* daddy AND *her* daddy AND be my pussy slave too.”
Alex looked desperate. “No!” she said. “That’s horrible! I can’t!”
Jessa shrugged. “Well, then you’ll keep needing to cocktease your daddy if you want to cum. And we both know you can’t help yourself, and that you need to cum. I wonder what your parish priest would say about that?”
And that was all it took. Alex, defeated, agreed.
Over the next few months, Jessa had a wonderful time watching Alex awkwardly trying to seduce almost every girl she knew, trying to find one she could blackmail. By the time she got a shy little blonde name Caty into her bed, she had a reputation around school as a lesbian slut. Caty started attending the sleepovers at Alex’s house, where Jessa would rape the poor girl, and order Alex to join in, and then Alex would think up the “slut taxes” for her, at Jessa’s insistence.
Alex turned out to be remarkably cruel, when pressed, and soon Caty was wandering the house naked at night, asking Alex’s father whether he thought her pussy was pretty, shyly but openly masturbating at the dinner table, and loudly discussing her fantasies of being raped by older men.
The first time Caty came back from a night-time excursion crying with Donald’s cum dripping from her pussy, Jessa made Alex lick her clean – and filmed that too, complete with Alex orgasming from having her pussy penetrated by Jessa’s fingers, with the taste of her own father’s semen in her mouth.
They gave Caty homework, to ensure that she would soon be fucking her own father, and then Jessa went back on her promise to Alex and made Alex crawl into her father’s bedroom in the night and give him a blowjob. Jessa had told Alex that she had drugged Donald, and he wouldn’t wake up from Alex’s attentions, but of course that was a lie, and shortly after she started sucking his cock as he slept, he woke up and ejaculated into her mouth, and from that point on Alex found herself fucking her father regularly.
Eventually, both girls fell pregnant to their own fathers, more or less at the same time, and Jessa decided it was time to give the girls their final degradations and move on to new challenges.
“You’ve been good little pussy slaves,” she told them, and watched their faces light up as they pictured the idea of being released from their slavery.
“Now, there’s two things we can do from here,” she continued. “Either I can go to the police, and tell them how your daddies have been raping you, and you’re pregnant with incest babies, and there’ll be a court case, and your daddies will tell the story of how you cockteased them as their defence, and all the slutty things you did, and I’ll make sure the police have all the footage of you lezzing off that I filmed. And either the jury won’t believe your fathers, and they’ll go to jail, and you’ll be left on your own with your incest babies – or they’ll think you’re lying sluts, and maybe it’s *you* who’ll go to jail…”
(The look of horror on their faces was priceless.)
“Or… you two girls can get married. It’s legal now. You can have a big pregnant lesbian wedding. I expect you to invite literally everyone you know, and I think your wedding dresses should show your tits and cunt. I expect to see you walk down the aisle with big gobs of cum shining on your face and tits and leaking out of your pussies, and I want you to have custom vows where you promise to rape and degrade and humiliate each other forever. In your speeches, you should consent to anyone in attendance fucking either of you at any time, don’t you think?”
She had them 69 each other as they thought about it, crying and lapping at each other’s pussies and orgasming, but she knew in the end that she’d be receiving a lesbian wedding invitation pretty soon….
She was looking forward to it.
By her last year of high school, Jessa had realised she had two very clear talents - spotting a repressed lesbian from a mile away, and seducing stupid girls.
Which was why Jessa wasn’t overly worried when her gorgeous queen-bee classmate Kimberly began to bully her. Kimberly may have got some initial laughs by calling Jessa a slut and a whore in front of the whole school, but when Jessa cornered Kimberly in the girls’ bathroom after school, and pressed her up against the wall, and asked her in a low, sultry whisper what she *really* wanted, it was clear that Kimberly couldn’t deny the forbidden lesbian lust she felt.
Kimberly’s town was a religious one, and her parents more religious still, and so at first their relationship was a secret. They met in out of the way places to kiss, and fondle each other. At school, Kimberly kept teasing Jessa - “so no one will guess what we’re doing” - and Jessa let it happen.
Eventually, Jessa talked Kimberly into sleeping over at her house. “My father won’t know what we’re up to,” she claimed, and soon enough Jessa had Kimberly in her bedroom, and was talking the pretty teen into stripping naked, and then rubbing her naked body against Jessa’s, and then scissoring, until finally Kimberly was nervously tasting Jessa’s cunt with her tongue, while Jessa eagerly pushed her tongue into Kimberly’s own fuckhole.
After that, the power dynamic shifted between the two. Kimberly did what Jessa wanted. This was for three reasons. The first was that Kimberly had talked herself into the idea that she *loved* Jessa. Jessa told her she was pretty, and made her feel good about herself and her body. (And, of course, Jessa was so *pretty*…)