The Karens - Cover

The Karens

Copyright© 2025 by Michele Nylons

Chapter 2: Cinderella

Incest Sex Story: Chapter 2: Cinderella - 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  

Alex knew that her ruse was up. The Karens, their boyfriends, Mitch Bellingham, and who knows who else had seen her at the country club and had witnessed her transformation from Plain Jane to chic nymphet. When she arrived at school she saw The Karens staring at her when she removed the stylish fur-lined coat she wore to keep out the cold to reveal a mauve skirt and jacket, black silk blouse, black opaque tights and chunky block heeled Mary Janes with and an over-arch strap. Her highlighted, wavy, layered, shoulder-cut coif and heavier makeup completed the ensemble.

Karen Allbright wagged a finger at her.

“Come with me snow bunny,” Alex followed the Karens into a vacant classroom.

“Quite the transformation, Walmart,” Karen quipped.

Alex said nothing. The Karens were wearing designer winter clothes looking more like fashion models than high school seniors but so did Alex. She leaned against the wall trying to act casual but said nothing.

“Miles Davenport. Florida based businessman and douchebag. I did a little digging over the weekend. One of his companies pays the rent on your townhouse and I bet he’s paying your tuition fees. Is he your sugar daddy? You sure came out of the ragbag for him Saturday night,” the Karens formed a semi-circle around her.

“He’s my uncle! I was emancipated at sixteen and Uncle Miles has supported me since,” Alex didn’t bother lying.

“Emancipated? Did daddy like to tuck you in at night a little too often? Did he like to help you take your bath?” Constance Dupree quipped wickedly.

“Eww! Nothing like that. My parents and I fell out over my life choices. They wanted me to leave school after my senior year and marry a boy from their church. They wanted me to be a housewife with screaming brats around my feet with a husband who worked at some lame job. They wanted a docile homemaker who gave them grandbabies and who cleaned house and shopped for groceries while her husband toiled at some dead-end job,” the practiced lie slid easily off Alex’s tongue.

“But why move all the way to Masons Peak to finish your senior year?” Felicity Lichfield chimed in.

“To get as far away from my parents as possible. Uncle Miles pays my rent, my tuition and he has a college fund for me too,” the half-truth was easy to say.

“But why the disguise? Why no attempt to make friends?” Karen was not going to let Alex off that easy.

“I’m a private person and I didn’t want to draw attention to myself. Do you know how hard it is joining a school for the last year of seniors? Everybody else knows each other. The cliques have formed, friendships are established. I knew that I would be the outsider and that suited me just fine. I didn’t want to have to explain myself to a bunch of people who care nothing about me and who I would only know for one year before I left for college,” it was easy for Alex to sound exasperated.

“If you had turned up like this on the first day I might have even considered letting you join our little entourage. You’re kinda pretty in your own way. You’re smart and articulate and it’s obvious you have fashion sense, even if you’ve been hiding it away for the last few months,” Karen leaned into Alex, her face inches away.

Her breath smelled sweet like bubblegum and she was wearing expensive perfume. Her skin was flawless as was her makeup.

“Are we still good?” Alex breathed.

“Tell me what happened in the restroom corridor at the country club Saturday night?” Karen smiled wickedly.

Alex turned to face Felicity Lichfield.

“Your boyfriend pushed me against the wall and felt me up. I defended myself and then Mitch Bellingham came out of nowhere and helped me. I didn’t come on to Denton, he came on to me. He was drunk and probably thought that I was easy. I’m sure that you girls have had to stave off unwanted advances before,” Alex appealed to their vanity.

“If you weren’t dressed like a whore in that red dress I’m sure Denton wouldn’t have gone anywhere near you,” Felicity Lichfield hissed.

“You’re probably right. My uncle bought me that dress and insisted that I get gussied up for a special occasion. He’d just clinched a big business deal or something equally as boring, but he looks after me so I dressed up for him,” another half-truth told easily.

“Ok Walmart. We’re still good. We are far too busy now to spend time hazing you anyway,” Karen said dismissively and Alex breathed a sigh of relief and turned away.

“By the way Alex ... love your suit,” Karen winked at Alex and smiled sweetly.

The Hanibal Lecter reference was not lost on Alex.

“Are you serious Karen! Are we really going to let that bitch get away with it? Denton swears that she came on to him!” Felicity whined.

“Oh get over yourself Felicity. You know that Denton is a poon hound when he’s drunk. He tried it on with me and Constance at the last kegger,” Karen dismissed Felicity and Constance Dupree blushed.

“But we haven’t finished with Alexandra Plessy. She’s still hiding stuff and I just don’t like her but you know what they say. Keep your friends close and your enemies closer. We are going to be nice to her for now, but like I said before, we need to think up something really big and surprise her with it when she least expects it,” Karen led her entourage out of the classroom so they could prepare for the first period.

“Hello stranger let me introduce myself. I’m Mitch Bellingham ... and you are?” Mitch Bellingham approached Alex at lunch.

“Fuck off Mitch,” Alex smiled at him, accepting the backhanded compliment.

“Wow! Just wow!” Mitch sat down beside her at the lunch table.

“When I saw you Saturday night I was blown away but given the circumstances it’s not like we could stop to chat. Then you turn up at school today looking like this,” Mitch indicated her outfit.

“Are you that fickle Mitch? Judging me by my appearance? I’ve had five other guys come on to me today already,” Alex clipped.

“That’s not the case Alex. I’ve been thinking about you since the cross country when I kissed you on the cheek but you were so aloof that I was afraid to approach you. Then you kissed me at the country club and I thought I had a chance, so here I am,” Mitch replied.

“So here you are. What can I do for you Mitch?” Alex was enjoying the banter.

“You said that you would find some way to repay me after I rescued you at the cross country, well, I want a date,” Mitch finally got to the point.

“You work at the country club as a busboy?” Alex changed the subject.

“Yep, I’m saving for college. I don’t have a rich uncle,” Mitch regretted saying it immediately.

“I’m sorry I said that. I saw you sitting with him at the restaurant and Felicity is already putting around that your uncle is some big deal down in Florida. It’s none of my business really, I shouldn’t have bothered you,” Mitch began to get up from the table.

Alex knew that this was her chance to let Mitch go on good terms. She had made peace with The Karens. Uncle Miles had stopped sulking and complaining and had even offered to lease her a car after their passionate weekend. Things could continue as they had since she arrived Masons Peak. She could be the loner, the recluse, the girl who kept to herself and just concentrate on getting good grades.

But Alex knew that it wasn’t Denton Stevens’ hands on her body or Miles’ passionate kisses and prolonged foreplay that had fuelled her desire on Saturday night and all day Sunday. It was the memory of the kiss that she had stolen from Mitch Bellingham outside the kitchen. The feel of his body pressed against hers in that satin gown, the softness of his lips and the urgency of the situation had fired her imagination and when she was lying under Miles Davenport, moaning like a slattern, it was Mitch that Alex was dreaming of.

But she had a huge secret. Nobody in Masons Peak knew that she was transgender so Mitch was under the assumption that she was a cis woman. Was it fair to lead him on? Not telling him would be deceitful but telling him could have enormous consequences. He might be repulsed by her. She had moved to Masons Peak because Minnesota is considered to be one of the most LGBTQ friendly states and transgenders have the same legal rights as non-LGBTQ people but people have their individual prejudices. Alex had no intention of coming out as trans unless she had to.

Then she rationalised that she would only be living in Masons Peak for a year or so. If Mitch blabbed that she was trans she could live with the consequences but she preferred not to. She had come out as trans at her last school and had effectively been banished, although technically she left before she was expelled.

Alex had never had a boyfriend. When she came out as trans in Miami she had been shunned. A few predatory types had come on to her when they knew that no one was looking but she instinctively knew that they were just curious about what it would like to fuck a tranny in the ass or maybe she might throw them a blowjob. She saw right through them. Anyway there was no way that Uncle Miles would allow her to have boyfriend.

She began to rationalise. What if she and Mitch just became friends? Even if they canoodled a little she could stop it before things got to the stage where she would have to reveal the secret she kept hidden in her panties. She desperately wanted company but only with someone she could trust and so far Mitch seemed trustworthy and gallant.

She put out her hand and clamped it on Mitch’s wrist to stop him from leaving.

“One date. Friday night. You pick where,” Alex looked around and saw that no one was looking and she kissed him quickly on the cheek and got up and left the table exposing a lot of leg when she did so which was not lost on Mitch Bellingham.

Alex fretted all week about the forthcoming date but she was also excited. Where would Mitch take her? Would he try to kiss her? Where his intentions honourable? She knew that she was behaving like a eighth grade girl rather than nineteen year old young woman: exchanging furtive smiles with Mitch in classes, brushing against each other in the corridor, fussing about how she looked before she went to school, showing him a little more leg and cleavage to tease him.

On Wednesday a bright yellow Mini Cooper was delivered to Alex’s town house. It had a big red ribbon tied around it with a card attached.

’To my wonderful niece Alexandra, thank you for a wonderful weekend and I hope there are many more to follow. I am very proud of you and wish you all the best. Keep making your grades and I look forward to helping you select a college worthy of your talents’ the card read.

It was Miles way of thanking her for the incredible sex and behaving suitably subservient over the weekend. It was also a reminder of his control over her and his intention to keep her as his concubine when she went to college but it was innocuously worded.

In the glove compartment was the lease, the registration and the insurance papers. As was his custom, the vehicle was leased by one of his companies with no direct link to Miles.

All that aside, Alex was pleased that she no longer had to walk or bike to school in the bitter cold and snow. Masons Peak was a mostly affluent community and most of the seniors had cars; mostly good cars but there were some beaters. Her Mini wasn’t exceptional by any means but the bright yellow finish with the black racing stripes made a statement.

“Nice wheels Alex, did Uncle Miles buy you that for your birthday or was it for being a good girl?” Karen Allbright quipped when she pulled up next to Alex in her Lexus.

Alex wasn’t sure if Karen was paying her a compliment or insinuating something sinister but she was not going to engage either way.

“Uncle Miles leased it for me. It’s just a loaner really,” Alex replied.

Chad Pemberton pulled into the parking lot and walked over and kissed his girlfriend and they walked arm in arm towards the school buildings, disengaging as they left the parking lot. PDAs were not permitted on school grounds.

Mitch Bellingham parked the beat up 2005 Dodge Ram pickup that he was restoring and sauntered over looking suitably cool with a hint of ‘bad boy’ in his ripped and faded jeans and scuffed leather jacket. His smile made Alex tingle all over and for the thousandth time she wondered why he didn’t have a steady girlfriend.

“Nice to have a rich uncle. Are you sure that you don’t want to pick me up on Friday? Your car is a lot better than mine,” Alex knew that the banter was good natured.

“A gentleman picks up his date and drives her home after. I do hope you are going to behave like a gentleman on our first date,” Alex teased him.

She turned away, knowing that her skirt would flick up tantalisingly as she did so, and strode off towards the school. Mitch liked that Alex still wore skirts in the winter. Those long legs clad in shimmery opaque pantyhose were a real distraction and he wondered what it might be like to feel them. As it turned out, he found out Friday night.


“You have got to be kidding!” Alex squealed when Mitch pulled into the grassed parking lot next to the carnival that had been set up in a paddock on the outskirts of town.

The traveling carnival came to Masons Peak once a year and consisted of amusement rides, food vendors, merchandise vendors, games of chance and skill, thrill acts, and animal acts. It was the perfect first date. No fancy restaurant where they would have to make small talk to fill the awkward silences or a movie where they would sit nervously side by side munching popcorn wondering if it was ok to neck. They could have fun as they rode the rides, unselfconsciously eat messy junk food and still be able to chat and banter and get to know each other.

Mitch helped Alex out of the cab of his truck although she didn’t need it but it was good way to behave gentlemanly whilst getting a glimpse of thigh as her skirt rode up when she slid out of the seat.

Alex had tortured herself about what to wear and not knowing where they were going made things harder. She wanted to look pretty but not slutty but still show off her best attributes. She finally decided on a simple black A-line skirt, a round-neck white body-hugging sweater, pink sheer tights and sensible black strappy shoes. She’d let her hair out and her makeup was a little heavier than what she wore to school but not whorish.

Mitch was wearing tight faded blue-jeans, a long sleeve tee, his favourite leather jacket and ankle boots. His shoulder-length sandy hair blew around his handsome face in the wind. They walked quickly to the carnival where the trailers, amusement rides and tents formed a barrier against the wind and the air was warm with the smell cotton candy, hotdogs, hamburgers and beer. Mitch helped Alex take off her hooded fur lined coat and he was impressed by what she had chosen to wear.

“You look nice,” Mitch commented nervously.

“You can fuck off Mitch if that’s gonna be your best line,” Alex playfully punched him in shoulder then leaned in and kissed his cheek.

Her hair tickled his face and her perfume smelled exotic. They were both glad that the tone had been set for a playful evening with nothing serious being discussed or inferred. They hit the rides, riding the tilt-a-whirl, the Ferris wheel, the haunted house and they delighted in crashing into each other in the bumper cars. On the more exciting rides Alex clung to Mitch which he did not mind one little bit. He liked having her press her body into his and got a bit of ‘side-boob’ action when she did so.

He won her a big teddy bear at the shooting gallery but they both lost on the ring toss, the bowling pin knockdown and the balloon pop which were all rigged anyway. They had their fortunes told, watched a juggling exhibition and a clown show and by then they were famished and made their way to the concession tent. Mitch sat Alex down at a table away from the crowd and went in search of food and drink. There was no ID check when he purchased two Bud Lights and he came back to the table with a tray loaded with food and the beer.

Mitch sat across from Alex and reached for a hotdog topped with caramelised onions, crunchy bacon bits, melted cheese and drizzled with ketchup and mustard.

“If you think you are going to kiss me after eating that you’re dreaming,” Alex screwed up her face.

“Ew! Who would ever want to kiss you!” Mitch laughed and took a big bite of the hotdog.

“Well, not you now, that’s for sure,” Alex smiled at him and dipped a French fry into the little container of mayonnaise and twirled it around.

“Well now that you are eating the devil’s jism there is no way I’m going to kiss you,” Mitch pointed at the mayonnaise.

“Good that’s settled. You now know that I hate onions and I know that you hate mayonnaise,” Alex smiled at him and then pushed the French fry into her mouth ensuring that some mayonnaise dribbled down her chin.

“Oh my god that is disgusting!” Mitch reached for a napkin and wiped Alex’s mouth and they both laughed and reached for their beers.

“Here’s an idea. Lets forget the small talk and get right to it and tell each other five things that we like about each other,” Mitch took a swallow of his beer.

“Even better. We tell each other five things that we like about each other and five things that we don’t like about each other, sort of a switch on Ten Things I Hate About You,” Alex grinned smugly.

“Well you are sort of like Julia Stiles but not as pretty and you don’t have blonde hair,” Mitch teased.

“And you’re sort of like Heath Ledger without the cute Aussie accent or his good looks. You kinda try to pull him off with the faded jeans and beat up leather jacket but I’m getting more Fonzie than Heath,” Alex returned the quip and stuck another fry in the mayo and ate it with her mouth open.

“Classy ... I tell you what; that’s the first thing I don’t like about you. You chew with your mouth open,” Mitch tried to sound serious but he was choking back a laugh, especially when Alex grabbed a handful of fries, doused them in mayo and stuffed them in her mouth.

“Ok so I’m ugly, I eat mayo and I don’t have table manners, keep going,” Alex was thoroughly enjoying herself.

“Well you run like a girl and you made me lose a race that I was sure to win,” Mitch made a stupid face.

“Is that five?” Alex asked.

“No, that counts as one. Your babyshit yellow clown car is so small and stupid that if you put that teddy bear I won you in the passenger seat you could get away with driving in the carpool lane,” Mitch banged the table and raised his hands and gave her a double Vee hand gesture.

“Is that all got,” Alex smiled meekly at Mitch and then launched into her response.

“You think you’re cute with your lone wolf attitude, long sandy hair, pretty face and shitty leather jacket but you are a second rate desperate attention seeker with a bad haircut and poor dress sense,” Alex took another French fry.

“I’ll take cute; the rest is debateable but keep going,” Mitch smiled.

“You are never going to finish restoring that car and you need to fix the heating rather than wasting money on the fuzzy dice hanging from your rear vision mirror,” Alex quipped and ate another fry.

“Hey!” Mitch pretended to be hurt.

You are the one that runs like a girl not me and you were coming last in that race when you stopped to help me,” Alex put a finger up to stop him when Mitch tried to interject.

“And finally, when you wear your sports tights your package looks tiny,” Alex gave him a mischievous grin.

“Hey! I thought we weren’t going to comment about each other’s bodies but I have to tell you that when I do wear my sport tights I have to tuck my junk otherwise all the other guys would feel inadequate and the girls would swoon,” Mitch leaned over and stole a French fry.

Alex blushed. Talking about tucking was a something that was too close to home.

“So now the five good things,” Alex said.

“Ok, you are intelligent, witty and can hold a decent conversation,” Mitch began.

“You are independent and don’t care what people think about you,” he continued.

“I’ve seen you perform in drama class and I think you have the potential to be a good actor but that might also demonstrate an ability to present a façade and you might be hiding a deep dark secret. You’re not a serial killer are you?” Mitch joked but Alex inwardly flinched because she was hiding a deep dark secret.

“I like it that you stood up to The Karens when they were hazing you. You didn’t back down but you didn’t have to resort to snitching on them. I like a girl who is independent and able to stand her ground,” Mitch said with a serious tone.

“And finally, because you got personal, your ass looks awesome in those leggings you wear to PT and your legs always look amazing,” Mitch blushed as he said it.

“So my tits aren’t worthy of praise?” Alex blushed and took the compliment despite her joshing.

“Oh, your tits are fine but I’m an ass and leg man. Your turn,” Mitch beamed at her and took a swallow of beer.

“Ok, I like that you are a hard worker. I know that you work at the country club on weekends and do yard work after school to subsidise your income,” Alex began.

“I also like that you too are independent and don’t hang out in a clique like most of the guys,” she continued.

“You too are witty, a great conversationalist and don’t take yourself too seriously,” she dipped another fry into the mayo.

“I like it that you are gallant enough to have to come to my rescue on two occasions but aren’t supercilious enough to make a big deal out of it,” it was Mitch’s turn to blush.

“And finally I like it that you picked a perfect place for our first date,” Alex reached across the table and squeezed his hand.

“Well thanks and on that note I think it’s time to wrap this up. I have to work all day tomorrow and Sunday,” Mitch started gathering up the food scraps and empty beer cans and put them on the tray.

In the car on the way home Alex began to think seriously about what she was doing. She had never been on a date before with anyone except Miles and she had enjoyed it immensely but where was she going with Mitch? She didn’t have that long left in Masons Peak and they would both be going to different colleges. There was definitely a spark between them which she realised could easily become a flame but she hadn’t told him her biggest secret. What would his reaction be if and when he found out that she was trans? She didn’t want to lead him on. Then there was Miles Davenport to consider. Maybe they could just continue as friends and leave it at that.

Her driveway had been cleared but a light sprinkling of snow was falling when Mitch pulled up outside her townhouse. Here came the awkward part.

Mitch went around and got the car door for her and walked her to the porch. They were both nervous but Alex doubly so. She set her resolve. She would let him kiss her goodnight and that would be it ... no tongue and definitely no sex, this was their first date after all. She waited for Mitch to make the first move as she stood there with the ridiculously huge teddy bear in her arms.

“Well I guess this is goodnight. Thank you for a fantastic evening,” Mitch stood in front of her at a respectful distance watching snowflakes cling to her hair and lashes; she looked beautiful.

Alex was thinking of a witty reply when Mitch suddenly took her in his arms and kissed her. Alex’s resolve melted immediately. The kiss was at first soft and tender but soon became fervent and needy. Alex dropped the bear and wrapped her arms around Mitch and returned the kiss, sliding her tongue into his mouth, ignoring the taste of onions and beer. Miles was a good kisser but Mitch did things with his tongue that ignited a burning desire.

They pressed their bodies together and despite their bulky clothing they could feel the need in each other. Her breasts mashed against his chest, Mitch slipped a hand inside her coat and squeezed her ass and she put her hands inside his jacket so that she could hold him closer. The kiss seemed to last an eternity and Alex told herself that this was it. They would say goodnight to each other once the kiss was broken.

“Come inside, it’s freezing out here,” she whispered when they finally broke the kiss.

She scooped up the bear and turned her back on him so that she could unlock the door.

’What was she doing!’ she thought as she let him inside.

The heating was on and Mitch helped Alex out of her fur coat and then took off his jacket then he reached for her again and kissed her. They stood in the hallway kissing passionately, the heat of their bodies matching the warmth coming from the heating vents. Mitch cupped her buttocks and squeezed them and she felt his cock thicken against her belly through his tight jeans.

She would let him cop a feel here in the hallway and then send him on his way with blue balls. Alex was determined to put a stop to this madness.

“Let’s go into the loungeroom,” she gasped into his mouth.

She took his hand and led him to the couch where they took up where they had left off. Kissing each other greedily and pawing at each other. Mitch squeezed her breasts through her sweater and felt her nipples engorge. She put her hands inside his long-sleeved tee and raked her fingers along his chest and across his six-packed belly.

“I’m not going to fuck you,” Alex gasped when they finally took a breath.

“Ew! Who would want to fuck a harpy like you,” Mitch tried to make light of the situation.

“Shut up and kiss me, stupid,” Alex reached for him again, kissing him deeply, her hands under his tee, caressing his warm skin.

His hands slipped inside her sweater and he expertly unclasped her brassiere. He squeezed her breasts and fingered her erect nipples and Alex gasped into his mouth. She removed a hand from inside his shirt and pressed it to his groin and traced the outline of his cock through his jeans and it was Mitch’s turn to gasp.

Alex could feel that Mitch’s cock was huge, he wasn’t joking about the size of it when she’d jested about his package. Frissons of delight were radiating from her breasts and her lips as Mitch tended to her nipples and his tongue swirled in her mouth. She could feel his cock pulsing in his jeans, straining against the denim, aching for release. Her own cock was uncomfortably bloated between her legs, stretching her pantyhose and panties. She was terrified that Mitch might attempt to feel her up through her panties and when he slipped a hand under her skirt and began to stroke her thighs she balked.

As delicately as she could, Alex removed Mitch’s hand from under her skirt.

“Sorry I went too far,” Mitch lay on top of Alex breathing heavily, his cock pressed against her belly, one hand still idly fondling a nipple.

“You know I read somewhere that in South Africa, premarital vaginal penetration was not allowed in traditional Zulu society but young people could have external sexual intercourse between the thighs,” Alex smiled up at him salaciously.

“God, I love it that you are a history buff,” Mitch began to kiss her again while Alex struggled to unbuckle his belt and unzip his fly.

Mitch helped her yank his jeans and underpants down his thighs. His boated rod sprang free and Alex cupped it in her hand. She could barely get her fingers around the girth of it. It throbbed in her hand, the veins pulsing under the silky flesh, the glans a swollen mushroom that was leaking pre-ejaculate which Alex used to lubricate the fine specimen of manhood as she stroked it.

Mitch’s kisses became fervid and he slipped both hands under her ass and squeezed her buttocks with urgency. She could sense that he was close to extremis and she guided his penis between her thighs and clamped them shut. The silky sheer sensation of Alex’s pantyhose-swathed flesh lit up the pleasure centres in Mitch’s body and he gripped her buttocks tightly as he began to fuck her legs.

The perception of Mitch’s colossal organ sliding between Alex’s thighs was overpoweringly erotic and Alex’s cock strained against her pantyhose, wetting the nylon with precum. She would have loved to put his cock there, pressing it against hers but that was only a dream. She closed her legs tighter around his cock as he humped her thighs while she raked her fingernails down his back, kissing him with intense fervour.

She felt his cock palpitate and suddenly her thighs were sodden with a glutinous wellspring of steamy milt that soaked into her pantyhose and puddled between her legs. Mitch was driving her into cushions, thrusting his cock between her silken-shrouded limbs, the sensation of her gossamer nylons and sleek soft flesh against his sensitive organ drawing every scintilla of semen from his shuddering organ.

 
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