Hailey's Vacation

by

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, Fiction, Oral Sex, Slow, .

Desc: Romantic Sex Story: When single mother Hailey wins the vacation of a lifetime, she meets a mysterious single father who sweeps her off her feet. But when a figure from her past appears, will it derail what she is building?

When Hailey Davidson was a 20-year-old college sophomore, her biggest worries were getting to class on time, knowing where the next party was, making sure she did her homework, styling her long, blonde hair, finding the right eye shadow for her blue eyes, and making time for her boyfriend, Alan Bryant. Alan was taller than the curvy and petite, 5’3” Hailey; standing 5’11”, with brown hair, brown eyes, muscular build. They had been dating a few months. Alan very much wanted to move forward in the relationship, specifically sexually, but Hailey, who already had one pregnancy scare a year before with a now ex-boyfriend, wanted to prevent such an occurrence from happening again. The challenge was keeping this from her parents whom she feared would become enraged and cut all financial support and contact with her. She decided to use the school’s health clinic as they promised confidentiality, especially in the realm of birth control. The problem she ran into was a two-month wait to get an appointment due to limited funds.

She shared with Alan the delay in getting on the pill and suggested in the meantime they use condoms if he didn’t want to wait. Alan said he was allergic to latex and insisted they use lambskin ones. However, during their first attempt, they discovered that Hailey was allergic to the lambskin. Hailey asked around and learned if they used both, they would both increase the protection and neither would be in contact with the product they had issues with. Alan however, found this to be wasteful and decreased his enjoyment. He insisted they go bareback and promised to pull out when he climaxed. His pre-med friend told him the safest time for them to have sex and not get Hailey pregnant. Armed with this information, Alan convinced Hailey to “trust him” and have unprotected sex.

On the day of Hailey’s appointment to get birth control pills, she made a horrid discovery. Alan’s sure-fire pregnancy prevention information was anything but accurate. The doctor politely informed Hailey she was indeed six weeks pregnant. Hailey’s world crumbled around her. She spent the bulk of the day in shock, processing the information the doctor had shared. Now she had some decisions to make. Did she keep the child and raise it with Alan, a man she wasn’t sure she wanted to marry, give the child up for adoption, or terminate the pregnancy? None were options she liked. That evening, she told him. Alan’s reaction wasn’t what she expected. Instead of discussing their options, he accused her of being unfaithful and trying to trick him into marriage. She didn’t want to marry Alan, the sex they had wasn’t that great, and she didn’t like how he treated her. It devastated her that he didn’t know her better and thought so little of her.

As she lay awake staring at the ceiling, she debated about her options. She knew Alan was the father, and that was the only thing she knew for sure. Devastated and confused, she made an appointment at her college health clinic to discuss her options and make a decision. The earliest one available was a week away so she spent the time thinking about her options, but felt lost. She had too many questions, and not enough answers. The night before her appointment and her dreaded deadline with Alan, her parents called. Hailey hadn’t planned on telling them, but as soon as she heard her mom’s voice, she burst into tears and told them everything about the pregnancy and Alan’s reaction. Her parents listened in disappointed silence, then told Hailey they’d support any decision she made, no matter what. It was what helped her decide barring a life and death situation, she would keep the baby.

Hailey saw the doctor who confirmed everything was fine, predicted her due date for late October, and wrote her a prescription for some prenatal vitamins he wanted her to start taking. Her parents helped her find a good OB/GYN. However, Alan didn’t take the news well. He maintained his accusations of Hailey being unfaithful and refused to be a part of hers and the baby’s life. When Hailey shared this with her parents, they decided to hire a lawyer to make Alan pay child support. Alan hired his own lawyer and thus began an almost three-year court battle over the paternity of the healthy, 6lb, 9oz baby boy Hailey had just weeks before her 21st birthday.

Despite numerous court orders, Alan refused to take the necessary DNA test to prove he was the boy’s father. Ultimately, the judge determined that after three years of delays and Alan’s refusal to take the test, that Alan was the father by default, and the only way to change his ruling was to submit to the test. If he was found to not be the father, Hailey would be made to pay back every dime paid with interest. However, if Alan was found to be the father, after all, the payments were to be doubled and it would be retroactive to the day the boy was born. That would be the last time Hailey saw Alan for over fifteen years.


Hailey became a hard working single mother who never took a vacation for herself, by herself, in her life. Her son, Timothy, whom she named after her father, had never met his father because he took off to finish his education and fought paying any child support claiming the boy wasn’t his. She moved back in with her parents and worked several menial jobs until her son started school. She refused to take any government aid aside from health insurance for Tim, WIC, and food stamps. She took classes when she could, and thanks to the support of her parents, was able to earn a degree and get a job that paid well enough for a nice two-bedroom apartment.

Since Hailey had to be both mother and father to Tim, she tried to make his life as normal as possible. She signed him up for local sports leagues and cub scouts to find what would best hold his interest and provide him interaction with other children. It was during these times he asked about his father. Hailey tried to keep a civil tongue whenever she spoke of the man whose sperm created the child she loved more than life itself, but often she’d just change the subject in lieu of saying something she’d later regret. Little league baseball, soccer, basketball, and scouting helped occupy her son’s time but always chewed a serious hole in her already meager savings. Yet, to Hailey it was investment in his future and worth every penny and hours of overtime or fundraising she had to do.

Over the years, Hailey dated, but never brought a new man into her home or into Tim’s life. When she admitted she had a son, many stopped calling. The few who didn’t go running, often didn’t accept that Hailey would rather spend a Saturday with a group of dirty boys camping or on a soccer field than out dancing and seeing a movie. Though, truth be told, Hailey hated camping and all the outdoors activities that came with scouting, and more than once she got sick from sitting out in the rain or extreme cold during a late soccer game. But she joked with the other mothers about it and made the best of the situation. In her mind, Tim’s happiness was the only thing that mattered.

As Tim got older, he asked if Hailey minded if he gave up some of the sports he didn’t like as much. She didn’t, especially since all the sports put a lot of stress on her already tight budget and she wanted Tim to be happy. He gave up baseball and basketball to focus more on scouting and soccer. When Tim entered high school, things changed rather quickly. He signed up for the school’s ROTC program and really thrived. He loved the structure and discipline this provided and he began to make plans for college. Hailey’s meager savings wouldn’t pay for more than a year at a local junior college, and she knew she’d need help. But the economy was bad and her boss couldn’t give her raise, so once again she sought out her son’s birth father. Unfortunately, he was still difficult to find and the lawyer who had helped her in the past, couldn’t afford to do much without being paid, even though he did donate as much time as he could afford to spare.

Tim’s involvement with soccer, ROTC, and boy scouts lead to college scholarships Hailey hadn’t even considered. Tim earned his Eagle Scout, played for the high school’s soccer team for four years, and thus, was recruited by an in-state university to play soccer, and entered their ROTC program after graduating high school. These programs paid for the bulk of Tim’s education and Hailey could cover the remaining costs allowing Tim to focus on his education and not have to get a part-time job.

It wasn’t until part way though Tim’s first year of college that Hailey realized how much of her life had been tied to her son’s. Suddenly, her once busy weekends were free and she had no plans for the summer the way she had before for so many years. After some persuasion, she went out with some co-workers to a charity event with a live band and a raffle. All the money collected was to go to the charity and they were assured that none would pay for events like this as many of the services were donated. The event was held at a local bar and even a percentage of the drinks and food were going toward the charity. There were a variety of prizes including passes to the local movie theaters, dinners for two, and the grand prize was a three-week trip to an all-inclusive five-star beach resort. Though Hailey didn’t have a lot of spare money, she decided instead of buying an alcoholic drink and something to eat, she’d put her money toward the charity instead. She bought twenty-dollars worth of tickets and joked that if she won the trip it would be the cheapest vacation she’d ever have. What Hailey didn’t know, was her friends had put her name on most of their raffle tickets to increase her odds of winning a prize.

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Story tagged with:
Ma/Fa / Consensual / Romantic / Heterosexual / Fiction / Oral Sex / Slow /