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Hailey Living With Dad Reboot

Hailey Living With Dad Reboot

by dringschultz
19 min read
4.73 (15700 views)
adultfiction
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Hailey: Living With Dad Reboot

Prologue.

September 2022

7:55 am. The alarm sounds for the third time and Hailey Riley groans as she reaches for her phone to silence it. Accepting she had exhausted every possible minute available to her, she rolls out of bed, stretching her arms over her head and yawning. Looking at herself in the floor-length mirror as she stretches, the old thin t-shirt rises to reveal her bare mons and stomach, she turns sideways to inspect her profile, rubbing her tummy, I need to lay off the beers at night, she thinks. She further turns and admires her ass, pleased with the progress her effort to swim every day has produced; her thighs are a little tighter, her booty sits a little higher. She checks her phone, 7:57, shit. She looks back to see if her t-shirt covers her ass. It does not. Hailey smiles, walking out of her bedroom with a shimmy.

"Hi, this is Hailey," she answers. "I'm good, Dan, how you doing," she asks sitting at the desk, gliding the mouse, pointing and clicking as she talks. "Haha, yeah, you know me, the usual, just a t-shirt and nothing underneath." Hailey laughs, wondering if her dad's superintendent ever believes her when she answers his question about what she's wearing. She laughs along before adding, "So, it looks like Josรจ pushed Anderson Avenue until tomorrow, Tuesday, the...11th, but the plumber is still scheduled for 34th Street before noon today. Yeah, I'm still trying to get an answer on the front door for Mango Drive. Yeah. Yeah. I know. They said they haven't gotten confirmation it's been received at the port yet. Okay... yep... will do... okay... Have a good one, talk to you later."

Hailey returns a missed phone call and starts going through emails for several minutes before getting up and wandering barefoot to the kitchen. She starts the coffee maker and pops into the nearest half bath to pee. She thinks she should go brush her teeth and wash her face in her bathroom but she kinda feels likes being a bum she decides with a yawn before heading back to the kitchen to grab her coffee. She sees a note on the island, "Fruit salad in the fridge, Love you, Dad." Hailey smiles opening the fridge to retrieve her breakfast, her father, Mitch, has always been an early riser, usually out the door before 7 am having already made himself breakfast and coffee. Even when her soon-to-be officially ex-stepmother was here, her Dad would tidy up the kitchen, leaving it spotless before heading out for the day.

Hailey shuffles back to her Dad's home office, hands full, settling into the large leather chair. She checks more emails and answers a few text messages while mindlessly sipping coffee and eating fruit salad. This continues until she's all caught up, she checks the time, 10:16 am. Hailey rolls her eyes, another long day of doing almost nothing. She can't help but smile though, this would have been torture at her former job, but sitting around her nice family home almost naked was something she had definitely gotten used to.

****

This has been Hailey's daily routine since moving back home two years ago. She had lost her only months old job in late summer 2020, a financial casualty of Covid, and after struggling for a bit, she finally had to admit defeat and accept her Dad's offer to move back home with him and her stepmother, Janel. Hailey had quickly adapted to the freedom and privacy of living alone and would miss the ability to have men over, lounge around naked, and masturbate whenever the urge struck, which was often. But, truth be told, she missed her dad and their house, especially the pool and private backyard. Also, her dad offered her a job working for him, which made moving back an offer she couldn't refuse.

Mitchell Riley very high-end new homes, in the oldest, most in-demand part of the city, the same area they live in. The kind of area where people pay millions for a house just to tear it down and build a bigger one with no yard. Hailey's dad had built a reputation for quality and attention to detail that led to his niche as a boutique homebuilder for people with serious intentions and serious financial means. He only works with people interested in creating beautiful homes they intend to live in, this means no investors, no McMansions, no spec properties, and Mitch only works on a few projects at a time, ensuring his personal attention to every detail. Mitch's only other actual employees besides Hailey are his superintendent, Dan, and 'Uncle' Tito, who first worked for Mitch's father, an Air Conditioning contractor, and has known Mitch since he was a child. Tito did a little bit of everything for Mitch and was a de facto family member.

Mitch had built up a stable of reliable subcontractors, suppliers, and vendors over the years. That was how he met Janel. She was an in-demand interior designer and they had worked closely on several projects eventually becoming a couple and then getting married when Hailey was 20. Hailey always liked Janel well enough, even if it was a little weird having a stepmother who was only twelve years older than her. Or having a mother at all. Hailey's mother had never been a part of her life, and her dad was always reluctant to talk about her except to tell Hailey how much he had loved her mother. When Hailey was young and asked about her mom, Mitch would always deflect. Hailey soon sensed it was because it was painful for her father and she stopped asking.

Hailey's mom, Helena, had been in and out of their lives after Hailey was born. Hailey's few memories of her real mom were mostly negative; yelling, shouting, crying, being gone for long periods, then suddenly appearing and promising everything would be different, then disappearing again as suddenly. Helena had eventually been diagnosed as rapid cycling manic-depressive. It was believed that postpartum depression had triggered an uncontrollable escalation of an existing, undiagnosed, mental illness.

Years of attempts at treatment and medication were of no effect and Helena had been gone from all their lives permanently since Hailey was five years old, except for one incident when Hailey was nine. Helena had shown up at Hailey's school, out of the blue, after years of no contact. Her behavior was wild and scary. Her appearance was heartbreaking; she had obviously been living very hard. Mitch managed to get her into a treatment center but Helena left the second week and was effectively missing until many years later when they were notified that she had been found dead in a motel in west Texas, shot twice. There was a person of interest but no one has ever been arrested or charged.

Mitch's sister McKayla had acted as Hailey's surrogate mother for several years when Hailey was young, and remained Hailey's second favorite person, next to her dad. McKayla Riley Andrews Bondurant McPherson Holden was beautiful and smart and funny and always involved in something interesting. She remembers her Aunt living with them when she was young, cooking and eating, watching movies and TV, making chocolate chip pancakes in the morning, until she suddenly announced she was getting married and moved away when Hailey was 11. McKayla has been married and divorced three more times since, but always kept in touch, never missing a special occasion, but Hailey still missed her and always wondered why she left so abruptly.

Hailey's relationship with her stepmother Janel was always awkward. With Janel being only 12 years older sometimes it was like they were sisters, which could be fun. They often went shopping together. Janel always encouraged Hailey to flaunt herself more, always suggesting something more formal or stylish and smaller or tighter when they went clothes shopping, always pressing the importance of image, but Hailey was a laid-back Florida college student and Janel was a take-no-prisoners, self-made businesswoman. And sexy. It was obvious why her father fell for her, but she was a fiery Cuban and her Dad was quiet and unassuming, and typically didn't like people who talked a lot, and Janel rarely was silent. They were a weird mix, but Hailey thought maybe that would work for them, and at least for a while it seemed to, but over the past year it was noticeable they were growing apart, their relationship resembling a business partnership more and more, rather than a romantic one.

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Hailey couldn't help but feel partly responsible for Janel leaving. She was pleasant enough, but when Hailey moved back in Janel soon seemed annoyed at her always being around. Especially while things were shut down because of Covid, it was a big house, but apparently not big enough for three people with too much spare time. Hailey seemed to get on Janel's nerves easily despite her best efforts not to. Growing up Hailey typically lounged around in just panties and a t-shirt or a bikini all day and she had just assumed, given her step mother's previous encouragement and own sexy style, that Janel wouldn't object to Hailey picking up where she left off before she moved out and Janel moved in.

However, it was quickly evident Janel was bothered having a scantily clad stepdaughter always around the house, often telling Hailey to put on more clothes or pestering Mitch to say something. Though Mitch would always refuse, telling Janel she was being silly. As Hailey's resentment towards Janel grew, her wardrobe shrank. Hailey knew it was a childish reaction, but she couldn't help engaging in the passive-aggressive tug-of-war for female dominance within the home.

Janel and her dad began fighting occasionally a few months after Hailey moved back in and the arguments slowly escalated in frequency and veracity until they finally had a big, loud blowout about six months ago. Hailey couldn't make out much, but Janel said something about her dad wanting to fuck someone else that made Hailey snicker. She knew her father wasn't the type to have an affair, but it hadn't gone unnoticed by Hailey that the sounds of fucking coming from her father's bedroom had grown much less frequent over the previous months. The day Janel moved out she was contrite and tender, telling Hailey that despite her and Mitch's relationship failing, as far as she was concerned they would always be family and Hailey could always come to her for anything. They hugged and promised to keep in touch. Hailey was genuinely moved by Janel's statement, but couldn't help feeling a tremendous relief the woman was gone.

Hailey told her dad she was sorry, especially if her moving back had anything to do with Janel leaving. He was paying her the same as her previous job and she said she could start looking for an apartment. But Mitch wouldn't hear of it. He told Hailey it was inevitable and having her home made him happier than Janel ever had. Hailey couldn't lie; she really liked it better with Janel gone. Her dad would typically be gone before she got up and wouldn't come home until after 3 or 4 pm. She essentially had the house to herself all day.

Technically, Hailey's title was Purchasing and Accounts Receivables and Payables Manager for her dad's company. It would look good combined with her MBA on her resume. In actuality, she knew her dad was being extremely generous paying her to sit around in her underwear and do stuff he had always done himself. Monday's and Friday's were her only actually busy days, the rest of the week Hailey was killing time, reacting to anything that might require her attention as it happened.

****

Closing YouTube, Hailey checks the time, 11:29 am.

Fuck

, she blows an exaggerated breath. Her work was basically done; anything coming in could wait for a response. Time to play she smiles, opening her Father's personal partition on the desktop computer. She still feels a twinge of guilt even after more than a year of invading his privacy almost daily. Really though, it's his fault for making it so easy she rationalizes, entering 'Hazy Hailey,' her childhood nickname, in his password field.

Her dad's desktop boots and she immediately clicks the browser history. The office computer was only used for his business but it was still backed up to his cloud the same as his laptop, IPad, and phone. Hailey had discovered this by accident one day when her dad left later than usual and she found his side of the partition running. Curiosity had gotten the best of her and she snooped.

Hailey feels the familiar tingle as she scrolls through her father's weekend internet history. She smiles seeing the familiar blue 'L' icon, and lowers a hand to her pussy; pressing two fingers into her damp folds as she begins to read the incest story her father had opened the previous morning.

****

Hailey was no stranger to fantasy or role-play. She had tried her hand at camming for a while when she first got her own place. She liked the idea of being watched and briefly flirted with becoming a full-time 'cam girl' but found it to be too much work. The girls who made good money were tireless self-promoters who kept set schedules and developed regular, loyal fans. Hailey just wanted to get off from being watched and would hop on whenever she got horny, but camming had quickly introduced her to older men and their fantasies.

Truthfully, Hailey hadn't discovered much if anything about sex that she didn't enjoy, but she had found dating tedious and attempts at experimenting with guys her own age were often more frustrating than rewarding. The idea of falling in love and growing together and accruing experiences with your partner was certainly appealing, but reality was much more daunting. Hailey couldn't imagine falling in love with anyone she'd been with and she was far too horny and enthusiastic to wait for 'Mr. Right.' So she had done as most people her age and used apps to find as varied a field of casual sexual partners as she could.

Hailey spent her college freshman and sophomore years 'hooking up' regularly in between dating a few times, but never for more than a month or two. Being young, a lot of things were new and therefore 'fun' and distracting, but Hailey was already starting to grow tired of guys her age and had a gnawing feeling she was missing out on a lot.

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Towards the end of her junior year, a younger classmate, Kimmy, confided she was working as an escort to pay her way through college and though Hailey didn't need the money, she found her friend's stories exciting and decided she wanted to know what is was like to be paid to have sex with a stranger. Hailey went on a few 'dates' and quickly found the 'profession' provided opportunities for meeting older men and for rapid and varied sexual exploration far beyond normal dating. She found the experiences thrilling and decided to continue, acting as a paid companion as her schedule allowed, usually at least once or twice a week.

Though her 'dates' typically fell into two categories, an actual date somewhere public followed by sex, or just sex, there were enough assignations that fell outside that norm to keep things exciting and Hailey found her 'work' rapidly expanding her sexual horizons. Hailey found role-play and Light BDSM were popular requests. Threesomes were commonplace, most with couples, but there were a few with two men. One of her regulars was an older couple, the man was a state senator and Hailey was paid generously and had to sign an N.D.A. before going to their house. The husband and wife paid Hailey to pretend to be their daughter and had sex with her in their daughter's bedroom while she was away at college. The experience was naughty and intense and Hailey willingly repeated it several times until a bad experience with the man's driver late one night nearly made her quit escorting altogether.

Despite that bad experience, and a couple of others, Hailey continued to escort for several more months, including joining her friend Kimmy for a 'retirement party' where the two girls first had sex with each other in front of their audience before taking on all 17 men in attendance. Hailey had made six thousand dollars that night. She also considered quitting again, fearful that the money was too seductive. She enjoyed the illicit nature of 'the business' and the ability to explorer her sexuality, but she found herself using the money to justify tolerating bad experiences and increasingly agreeing to do things she didn't necessarily

want

to do.

However, the allure of illicit pleasure and easy money kept its seductive hold on Hailey and she continued to escort even after she graduated and began a 'regular' job. At least until the sudden onslaught of Covid in the spring of 2020 helped make her decision for her and Hailey left sex work behind for good.

It was a rough time for everyone Hailey kept reminding herself, but the spring and summer of 2020 was almost unbearable for the 22 year old. The unknown danger of the new disease, not being able to go anywhere or maintain a social life, the sudden loss of regular sex, and the financial uncertainty of her just begun professional career all built up until Hailey broke down, calling her father in tears and readily agreeing to his insistence she move back home.

****

I: Shifting boundaries.

October 2020

Hailey was grateful to be back home. The safety, security, and regular schedule of a job were a welcome relief. And the companionship of her father and stepmother helped distract from the boredom of being stuck at home. But of course nothing distracted from the loss of sexual contact, and simply masturbating to porn, her usual fantasies, or even the memories of her own experiences soon became stale.

Having catered to primarily much older men, Hailey couldn't help seeing how powerfully the daddy-daughter incest kink had affected some of the men she had been with. She had been a willing participant in their fantasies, but justified her involvement as strictly business, a taboo product to meet a perverted demand for financial gain. However, the truth was more complicated, Hailey was frightened to explore that part of her own psyche, having seen the emotional burden forbidden desires bore on those affected and she remained hesitant of pulling on any personal taboo threads less they unravel the only permanent relationship in her life.

And so Hailey ignored and resisted and distracted herself from acknowledging the possible existence of any form of sexual attraction to her own father, until one day, frustrated and desperate after months without sex, and unable to 'get off' to her satisfaction using normal means, Hailey Riley gave in and made the conscious decision to think about her dad when she masturbated. She rationalized it as just something naughty to try, almost like a dare to herself, just to see what it was like.

Though in the back of her mind the daughter knew that was a lie, the idea had been poking at her for a couple of years, the possibility or likelihood that she might like it, that it might turn her on. She had done her best to suppress that impulse, distracting herself with casual sex and sex work and frequent masturbation, but during that Covid spring and summer and then fall, - back under the same roof as her father, and in daily physical contact again - the idea festered and grew, working its way to the surface, like a sexual infection, the pressure demanding relief.

So Hailey made her fateful decision, assuring herself it would be harmless, just a little naughty fun to get off to, and the daughter laid in her bed and imagined having sex with her father. It was nervous and awkward, but also exhilarating and powerful in ways she hadn't imagined. It was also deeply and profoundly emotional; tears fell from Hailey's scrunched tight eyes, wetly rolling across her cheeks as she plunged her fingers in and out of her heated opening, imagining it was her father's hard cock that was stretching, pushing, probing... pounding.

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