The Karens
Copyright© 2025 by Michele Nylons
Chapter 1: Tribes
Incest Sex Story: Chapter 1: Tribes - Transgender teen Alexandra Plessy moves to Masons Peak to complete her senior year and escape her sex addicted uncle. She keeps her transgender identity secret and has to navigate the challenges of being 'the new kid'. She piques the interest of 'The Karens', three middleclass, self-centered, overly entitled bullies who are determined to put her in her place. She has to satisfy her uncle's sexual appetite whilst trying to have a stable relationship with her boyfriend.
Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa Teenagers Coercion Reluctant TransGender School Incest Uncle Niece Rough Anal Sex Cream Pie Masturbation Oral Sex Leg Fetish Small Breasts Revenge Transformation
Karen: ‘A middleclass girl or woman who is self-centred, overly entitled and excessively demanding and uses their class privilege to demand their own way.’
Masons Peak High School, Minnesota – Day One of Senior Grade
“Hello everyone and welcome to the first day of your last year in high school,” Vice Principal Mary Applebee announced in her grating cheery voice.
“Not for some!” some rogue at the back of the auditorium called out.
“That will be enough Mister Billingham or it will be you who repeats a year,” Ms Applebee said sternly.
“I’d like to introduce you to a new student who has recently moved to Masons Peak and will be joining the senior grade until graduation. Please welcome Alexandra Plessy,” Alex Plessy stepped awkwardly to the front of the stage, virtually pushed there by Mary Applebee.
As is the ritual when a new teenage student joins a school, Alex was scrutinised by the various cliques. The boys were of course interested in her looks and body, the girls assessed her clothing critically and tried to decide if she would be competition for the their boyfriends while the goths, jocks, brainiacs, stoners, theatre geeks and the other tribes tried to assess where she might fit in.
The three Karens sitting together in the back row made their own critical assessment. Alex was tall, slim, small-breasted and had a face that was not conventionally pretty but some might think attractive. Her nose was a little crooked, she had a small gap between her front teeth and she had a small but prominent scar on her chin. Her straight mousy hair was cut in a bob and hung to her shoulders. She was wearing green leggings with a short red skirt over, black flats, a knitted, seamless black scoop-neck top and a red wool cardigan to stave off the cold as the fall chill had arrived early this year. Her makeup was minimal but she had used eyeliner and mascara to effectively enhance her emerald-green eyes which were her most striking feature and applied some gloss to her full sensuous lips. She wore no jewellery except for a fine gold chain and locket around her neck.
“Walmart,” Constance Dupree whispered dismissively.
“Cheap,” Felicity Lichfield huffed.
“Loser,” Karen Allbright, the leader of the pack, made a show of studying her fingernails.
“A seven at best,” Rick Macklin, Constance Dupree’s boyfriend, whispered.
He was sitting in the row in front of The Karens with the other jocks, his feet up on the back of seat in front of him.
Constance Dupree leaned forward and clipped Rick across the ear.
“She’s a fucking three ... a four maybe!” Constance huffed.
Alex Plessy looked forlorn on the stage, staring out at her new peers who she knew were inspecting her. She couldn’t wait to leave the stage and settle into the anonymity of academia. She had no interest in joining any cliques, gangs or cadres. Alex just wanted to complete her final year of high school, graduate and go to college.
Thankfully Vice Principal Applebee nodded dismissively at Alex and indicted that she should leave the stage. Alex found a seat near the wings of the auditorium and sat by herself. She listened to Mary Applebee drone on about the example that the seniors should set to the junior students and spoke about integrity, school spirit and inclusiveness. Alex wondered how much inclusiveness existed in the sea of white faces she had witnessed whilst standing on the stage. The students congregated together in their tribal clans and the small assemblage of minorities sat together in their ethnic groups.
With the assembly over the students rose out of their seats and began to make their way to their classes, the silence replaced with the dull roar of teenagers enthusiastically chatting to one and other. Alex studied her timetable and accompanying map that had been issued to her in her indoctrination package and made her way to the math classroom. She felt eyes on her as she made her way to a vacant desk towards the back of the room. This was to be expected being the ‘new kid’ although Alex was hardly a ‘kid’ as she had recently turned nineteen.
As she passed Constance Dupree’s desk, Constance stuck out her foot and Alex stumbled over it.
“Watch where you’re going Walmart,” Constance quipped as Karen and Felicity sniggered at Alex’s plight.
“Nice skirt girl. Is that real vinyl?” Felicity smirked.
It was a childish prank and Alex didn’t respond to the sleight regarding her cheap skirt. She found a seat away from the three girls who were wearing designer jeans, expensive footwear and whose hair was stylishly coiffed. They were wearing far too much makeup and between them they smelled like the perfume counter at a Chanel store.
“Don’t worry about the Karens. They’re just testing you to see if you’ll bite,” a handsome young man with shoulder-length sandy hair whispered to her from two desks away.
He buried his nose back in his textbook and the class became silent when the tutor entered and began to address the assembled students.
Alex got through the rest of the day unscathed. Most of the classes were taken up with the teachers reviewing the curricula, setting first term assignments and reminding the seniors that they were now in their most important year of high school and the need to perform well academically if they wanted to get into a decent college. Alex sat by herself at lunch and politely declined offers from the emissaries sent by the cliques and tribes to go sit with them so they could bombard her with questions to see if she was a suitable candidate for membership.
When school was out Alex put aside the texts that she needed to study that evening and locked everything else in her locker. The texts went into her shoulder bag. She slung the strap over her shoulder as she made her way out of Masons Peak High School. Skipping down the wide stone steps she looked up and saw a red BMW convertible parked in the pickup zone.
“Fuck!” she whispered but made her way towards the vehicle with her head down.
“Hello sugar. I thought I’d surprise you with a visit and pick you up on your first day,” Miles Davenport leaned over and opened the passenger door.
Alex climbed into the cherry-red M4 Cabrio and Miles took the opportunity to check out Alex’s long legs as her skirt rode up. He put his hand on her knee as he pulled away from the curb.
“How was your first day?” Miles smiled at Alex and she returned the smile, suppressing a grimace as her uncle’s hand slipped further up her leg until it was resting on her inner thigh.
Alex had been emancipated at sixteen when she came out to her parents as transgender. Alex’s parents had suspected that their son was ‘queer’ for a long time and when they found girl’s clothing and makeup secreted in his bedroom they confronted him. There had been a bitter battle when their son told them that Alex wanted to change their name from Alexander to Alexandra and present as female and wanted to commence gender reassignment therapy, hormone treatment and maybe even surgery. Alex’s parents refused and hated it when Alex began started to openly wear androgynous clothing, walk and talk like a ‘pansy’ and began using feminine pronouns to describe herself.
Her uncle on her mother’s side of the family, Miles Davenport, had swooped to the rescue and offered Alex the funds she needed to support herself and rented a small apartment for her near her school on the outskirts of Miami Florida. Alex’s emancipation had been uncontested by her parents who shunned her and cut off all contact. Alex transitioned into a pretty teenage girl, fashion model tall with long shapely legs and with the help of medication and a little surgery developed curvy hips, a buxom bottom and perky breasts.
Alex’s uncle paid for everything and his lawyers pushed the necessary paperwork through the legal system for Alex to legally change her gender. Miles provided her with a generous monthly stipend and a small car to go along with the rented apartment. Alex was extremely grateful for her uncle’s unconditional support and generosity.
Miles Davenport had the decency to wait until Alex turned eighteen until he began to fuck his maternal niece.
Alex came home from school on her eighteenth birthday to find Miles sitting in her apartment and a stack of wrapped birthday presents piled on the kitchen counter. Miles greeted her not with his usual chaste kiss on the cheek and fatherly hug but with a full-on lip smacker and when he hugged her he squeezed her buttocks.
“Open this one first,” he handed Alex a package.
She tore open the cheesy birthday wrapping and found that it contained a red chiffon babydoll negligée. The garment had a formed bralette, an attached loose-fitting skirt falling in length to the upper thigh and was trimmed with lace ruffles and spaghetti straps. Hardly the gift an uncle gave his niece.
There was also a pair of red satin panties and matching suspender belt and a pair of expensive Wolford fully-fashioned black stockings.
“Go put them on and wear these too,” Miles handed her box, which when she opened it in her bedroom, contained a pair of red Jimmy Choo pumps with ridiculously high heels.
“Tone up the makeup and let your hair down,” Miles was not asking; he was ordering.
Alex wasn’t stupid. She had guessed that this day might come.
Her uncle wasn’t Elon Musk rich but he counted his fortune in millions. She knew that he catted around with attractive young women and high-end callgirls and made no attempt to hide the fact that he did. Alex often found a bevy of young women not much older than herself partying at his estate, lounging around his pool in skimpy bathing suits and occasionally a pretty young call girl leaving his house just as she arrived to visit. But Miles had never made any inappropriate advances and was kind and generous to her.
She looked at the lingerie and heels that her uncle had given her for her birthday she realised that this was the price she was going to have to pay for her uncle’s philanthropy. She might be emancipated but she was still at school and there was no way that Alex could make her grades whilst working enough hours to support herself. She knew that the apartment, the car and her generous allowance would all disappear if she didn’t bow to his wishes.
Alex allowed herself a few minutes to be angry and then sad but most of all she was disappointed with her uncle. She was well aware that she was pretty and that her body was sensual. She had seen boys at school looking at her the way boys do when they find a girl desirable but none of them had made any advances. When she came out as trans she lost all of her friends and some of them were downright hostile. She was a loner at school. Most of the kids just couldn’t get their head around the fact the boy they knew as Alexander was now a girl named Alexandra, especially when the therapies and surgeries began to change her appearance dramatically. School was almost unbearable but Alex was determined to complete her senior year and get into a good college.
Alex stripped and used the bathroom. Being a healthy teenage girl with a blooming libido Alex was sexually inquisitive but in the absence of male companionship Alex had purchased a sex toy and used it on herself while watching pornography. She knew the preparatory requirements before engaging in anal sex and she did what was necessary then she took a quick shower and applied the heavy makeup and let down her hair just as Miles had requested. Stepping into the lingerie, stockings and heels she looked at herself in the mirror and saw a girl similar to the ones she saw on the pornographic websites reflected back at her. She looked voluptuous, exotic and sexy and just wished it was one of the boys she fantasised about at school waiting for her in the adjoining room, not her uncle.
Alex was not comfortable wearing the provocative garments and unsteady on the absurdly high heels but when she walked awkwardly into the living room her uncle did not seem to notice her reticence. Miles had stripped naked and was sitting on the couch sporting a healthy erection. Her uncle was fit, tanned and goodlooking with perfectly coiffed dark hair. His personal trainer, personal chef, personal physician and stylist did their best to keep him looking young, fit and handsome. With the right amount of money anyone can be made to look attractive, Alex thought.
Fleetingly, Alex realised the hypocrisy of her thinking. Wasn’t her own face and body the product of her uncle’s wealth?
“You are magnificent Alex,” Miles sighed and patted the seat cushion beside him indicating that she should join him.
Alex was resigned to her fate but was determined that she would not be in any way responsive or encouraging. If her uncle wanted to gratify himself on her body she would endure it stoically. During her English lesson today the word of the day had been stoic and the class had been given ten minutes to write down as many synonyms as possible and Alex recalled the list: unemotional, impassive, emotionless, apathetic, cool, passionless, undemonstrative, indifferent, calm, detached, numb, aloof, unmoved, expressionless, unconcerned, unflappable, passive, resigned, philosophic, and self-controlled. Alex would be all these things.
Alex lumbered toward the couch and sat down gracelessly. She was trying to be deliberately gawky, putting aside the hundreds of hours that she had put in painstakingly developing feminine mannerisms until they became instinctive. Miles seemed not to notice and was fixated on her body and when she was seated he fell on her like a lion on its prey.
He pressed her down onto the couch dragging her into the supine position and lay on top of her. He crushed his lips against hers and she tasted mouthwash and whisky when her uncle thrust his tongue into her mouth. She lay still as Miles’ hands roamed her body, touching, fondling and exploring. He tweaked her nipples and despite her resolve to remain unstimulated they hardened to his touch. Alex convinced herself that it was just an automatic response; a reflex.
When his hands stroked her nylon-clad thighs and drifted upward across the front of her panties and she felt her cock begin to thicken, she opined that too was involuntary and she lay perfectly still and unresponsive.
“It’s going to be like that is it?” Miles chuckled evilly.
“Well, we will see,” he put his mouth on hers again and kissed her deeply, his tongue flittering in her mouth.
He pried her legs apart and lay between them and Alex felt his cock pressing against hers through the satiny panty material. He writhed his naked body on top of hers, his fingers stroking her nipples then drifting down her flanks to her legs where he caressed her thighs. His mouth was obscenely sensuous, his lips soft and inviting, his tongue exploring her mouth. Alex’s pleasure centres lit-up and she fought hard to remain unresponsive.
“I was hoping we might spend some time over foreplay and I want to feel your mouth on my cock but if you’re not going to play the game I’m just going to fuck you. I’ve dreamed of this for so long,” Miles whispered lasciviously into her ear.
She felt his hand scampering around, searching for something between the cushions and then she felt him slide the gusset of her panties aside and a cool, slippery slave being applied to her anal opening. Miles kissed her again and this time his fingers, slick with the salve, slipped inside her panties and wrapped around her penis. He stroked it until it was tumescent and Miles put his mouth to her teats and used his lips, tongue and teeth on them until they engorged. Despite her unwillingness Alex was becoming uncontrollably aroused. Miles slipped a finger inside her anus and she gasped. He wriggled it around a little and then had the audacity to remove it and sniff it.
“Good. Nice and clean,” he chuckled and began to kiss and fondle her again.
Alex hated herself for becoming concupiscent but her body was betraying her. Her nipples were tingling, her penis afire, her legs ached from where Miles had stroked her silken-clad thighs. He kissed her again and she could feel the want and the need in him, her unresponsiveness only served to fuel his ardour. She felt his cock wriggle between her buttocks and she tensed and screwed her eyes shut.
Despite his eagerness Miles took his time deflowering his niece and Alex hated him for it. She would have preferred that he painfully ravish her, causing her pain and discomfort so that she no longer felt so sexually aroused. Instead Miles slipped just the head of his thick, meaty prong inside her sphincter causing Alex to wince but the pain was soon replaced with sparklets of pleasure. Miles kept kissing her, working his mouth sensuously on hers, his fingers stroking her nipples then drifting down across her belly to her thighs where he caressed the pale sensitive flesh above her stocking tops.
When he was satisfied that Alex was no longer feeling discomfort he began to slide his engorged manhood inside her tight, slick anus. Alex felt Miles’ fill her rectal void, the pliability and dexterity of his thick, veiny appendage far superior to the silicon imitation that she kept in her top drawer. Her uncle’s cock was animated and responsive. She could feel it throb inside her, his steady heartbeat palpable as the veins along the trunk of his manhood pulsed with life.
Her sphincter radiated waves of delectation, the walls of her anus were afire with delight and a deep resonance emanated from her prostate.
Then Uncle Miles began to fuck her.
He kissed her with unbridled passion and his hands found every part of her that could be stimulated as his steely cock slid slowly in and out of her back passage. Alex’s body was ablaze with wantonness and desire as she lay underneath him trying her hardest not to respond to her uncle’s unwanted ministrations. His attack was overwhelming, accomplished and calculated. Miles was an expert lover and he was using his expertise and prowess in order to breach Alex’s defences.
Alex surrendered.
She let out a guttural moan and wrapped her arms around her uncle’s broad shoulders and lifted her legs and crossed her ankles behind the small of his back. She returned his kisses, locking her mouth on his, driving her tongue into his mouth as she writhed underneath him, pressing her aching cock against his hard belly as she forfeited her integrity for carnality.
Miles cupped her buttocks and lifted them off the cushion so he could ram every millimetre of his aching cock inside his pretty niece and smiled as he felt her stocking-sheathed limbs rub against his flanks, her heels scour his lower back and her fingernails rake his shoulders as she encouraged him to fuck her harder and faster. She gasped into his mouth and he felt her cock judder against his belly and then her panties became saturated with her essences. Her creamy issue smeared his belly and her orgasm triggered his own.
He pressed Alex down into the cushions and jackhammered his cock in and out of her tight sheath, feeling it ripple and undulate as Alex’s anus responded to her climax, milking him, extracting his seed. Alex felt her uncle’s cock judder inside her and sensed his hot buttery juices filling her void, driving her climax to an unprecedented summit. She had never felt so overwhelmed with desire and gratification.
Miles lay on top of Alex gasping, trying to recover from the exertion, his body still responsive to the gorgeous young woman who lay beneath him. Her ardour was sated and he was aware that Alex was feeling post-coital regret but he had no sympathy for her. If she was one of his whores, he would simply recompense her with cash but his hold over Alex was far stronger. She depended on him.
Now that her lust was satiated Alex felt dirty. She felt like a prostitute who had surrendered her virtue for privilege. There was nothing she could do to redeem her integrity; the deed was done. Miles climbed off her and walked over to the kitchen counter and unwrapped another of her presents. It was a bottle of Grey Goose vodka and he poured a generous amount into two glasses.
Alex sat on the couch with her arms wrapped around herself defensively, looking forlorn.
“Hey princess, I paid for those tits, that fine ass and that pretty face and I intend to take full advantage of them,” Miles growled.
“Grow up and stop being a baby. You still have your freedom but every now and then I’m going to drop by and collect on my debts. You can go home to mommy and daddy or go live in a flophouse while you toil away at some shitty job or you can enjoy everything I’ve given you,” Miles took a gulp of his drink.
“Don’t worry I’ll only drop by occasionally and I’ll give you plenty of warning. You be nice to Uncle Miles and he’ll be nice to you,” he sauntered over to the couch and thrust the drink at Alex.
She took a beat to think about it and then she snatched the glass from his hand and downed the contents in one gulp.
“Good girl! Now lets go unwrap the rest of your presents and then we can retire to the bedroom and see what you can do with that pretty mouth of yours,” Miles kissed Alex on the cheek and she used her all of her resolve not to flinch.
Alex had made a deal with the devil and now she had to pay her dues.
For six months Alex lived like a concubine. She attended classes, did her homework, did her community service to gain extra credits, kept house and tended to her uncle’s sexual needs when he demanded it. His visits were infrequent and he would call or text her beforehand providing specific instructions about how she should dress for him, often sending her pictures or links to websites or even sending her packages of clothing for her to wear when he visited.
Alex endured her uncle’s advances and try as she might to remain disconnected during his visits, Miles was an accomplished lover and she always found herself succumbing to his needs and actively participating. She hated herself for it but considered it the price she had to pay for her emancipation and lavish lifestyle. She knew that her uncle was exercising coercive control over her but she was willing to submit to him until she had the means to break free of his hold on her.
Her aspirations were shattered however when the very conservative PTA and School Board met and passed a resolution stating that ’A person’s sex is an immutable biological trait and that students must use the bathrooms, locker rooms and other facilities that reflect their birth gender and must dress accordingly’. The resolution went further than the legislation recently passed by the state and effectively barred Alex and any other trans students attending the school unless they presented as the same sex as defined on their original birth certificates.
Alex was at first devastated but then she realised that an opportunity had presented itself that could free her from Miles’ jackboots. She scoured the internet looking for schools in places considered ‘trans friendly’ and settled on Masons Peak High School in Masons Peak Minnesota. It was a very good school with a liberal outlook. That was the good news.
The bad news was that the school was unwilling to take in students halfway through their senior year. Alex would have to repeat her last year of high school, also the school fees were quite exorbitant.
The better news was that Minnesota was a long way from Florida where Miles Davenport had most of his business interests. He owned casinos, hotels, shopping malls and a golf course or two. His office was located in a gleaming tower in Miami as was his luxury beachfront estate.
Miles tried everything to keep Alex from moving to Minnesota. He told her that she could quit school and come work for him or even just forget about employment and live in Miami in an expensive condo with everything she needed paid for by him. When that didn’t work he threatened to cut her off and leave her destitute but Alex was determined that she would complete high school and get a degree. She wanted her independence.
Alex did everything she could think of to cajole her uncle into agreeing with her plan. She did things for him in the bedroom that disgusted her, she was overly affectionate, she promised that once she finished her schooling she would come work for him in Miami and be at his beck and call. She told him that Masons Peak wasn’t that far away, a four hour flight in his private jet, and she would continue to provide him the same services she had been providing for him in Miami.
They reached a compromise. Miles would use his money, his contacts and his lawyers to secure a place for Alex at Masons Peak High School, pay her accommodation and tuition fees and continue to provide a stipend for her to live comfortably. He even agreed to use his influence and money to persuade the Principal to enrol Alexandra as a cis female student and keep her trans identity a secret from the faculty and the student body. Alex did not want to face the discrimination and segregation she had felt at her previous school. She knew that although Masons Peak High School was progressive and inclusive, that some people harboured prejudices.
But Miles was vindictive. It was his way of punishing Alex for going to live so far away from him. He rented her a small one-bedroom townhouse apartment, took away her car and reduced her allowance. She would not by any means be living in poverty but her lifestyle would be frugal compared to how she was living in Miami.
When Alex moved to Masons Peak she changed her appearance. She started wearing clothing purchased at chain stores and packed away her designer labels. She toned down her makeup and straightened and coloured her hair. Gone were the perfectly coiffed, blonde locks, replaced by an unfashionable light brown bob with bangs. She did not want to draw attention to herself. She wanted to blend into the background and concentrate on her studies.
When Miles picked her up outside of Masons Peak High School after her first day of school his smile concealed a grimace. As his hand wandered under the cheap red vinyl skirt and began to fondle her thigh he couldn’t help but comment.
“You look like a pauper. I know that I cut your allowance but you look cheap, dour and unattractive,” Miles sniped.
“Exactly the look I was going for Uncle Miles but you still seem to be unable to keep your hands off me,” Alex replied cattily.
“When I get you home I want you to fix your makeup and get into something alluring. I’m only here for one night and I want to make the most of it,” Miles’ hand slipped between her legs and stroked her pubis.
“You’re tucked really well Alex which is just as well. We don’t want everyone to know that you’re a tranny now do we?” Miles growled.
Miles knew that Alex hated being called a ‘tranny’ and she knew that he was taunting her. She refused to bite and let him paw her all the way home. He insisted on opening the door for her and following behind her when she got out of the car so he could look up her skirt at her fine ass encased in the green leggings. When they got inside he pushed Alex against the kitchen breakfast bar and began to kiss and maul her even as she shucked off her shoulder bag.
“Just let be get ready and change Uncle Miles. I’ll wear that negligée you like with the satin panties, heels and I’ll slutty-up my makeup,” Alex tried to twist free of his grasp.
Miles did not reply. His mouth was on hers and he ripped off her cardigan and tore open the scoop-neck top, exposing her brassiere. He slipped his hands inside and caressed her breasts through the lace cups, feeling her nipples harden to his touch. Alex struggled to break free, but as tall and lithe as she was she no match for Miles’ muscled bulk.
He spun her around and pressed his crotch into her buttocks and pried her breasts free of her brassiere and pawed at them, flicking her nipples until they were fully engorged. His crotch rubbed against her buttocks insistently and she felt his cock become fully engorged.
“Stop! Let me change and prepare myself for you,” Alex pleaded, still struggling.
Miles kept one hand on her breast, tweaking the nipple between his fingertips while the other journeyed down her body to her hip. He rested it there and twisted Alex’s head so that he had access to her mouth and he kissed her passionately, almost painfully, crushing his lips against hers, nipping her tongue with his teeth.
“Let me go!” Alex cried.
She hated that Miles had made her nipples sing with unbridled pleasure and that she felt his cock pressing against her ass exhilarating. She hadn’t had sex since she had moved to Masons Peak and it was easy for Miles to arouse her despite her reticence.
“I can’t wait,” Miles growled into her mouth.
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