tagRomanceHailey's Vacation

Hailey's Vacation


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.

The band played and Hailey and her co-workers danced and had fun. Hailey was glad she came and figured even if she didn't win, the money went to a good cause. Her friends bought her a strawberry margarita when they noticed she was just drinking water. Hailey was too embarrassed to admit she spent her alcohol and food money on the raffle tickets and accepted the drink. The group also bought some sampler platters and shared them with Hailey. Everyone knew she was a single mother and how she struggled. It was no secret that she'd be the first to volunteer for any overtime offered and the bulk of her spare money went to her son. They all had switched shifts with her at some time so she could attend some event for her son, and her vacations were always spent on an outing for her son. What Hailey didn't know was how everyone knew how hurt she was when Tim chose to spend his first spring break with his friends at a beach resort in Mexico instead of coming home. Yet it was clear how she moped around that week and they knew her words did not match her feelings. This was why they wanted her to win a prize or two in the raffle. In their eyes, no one deserved it or needed it more. Hailey was the one person who never put herself first, and the girls decided it was time for Hailey to be spoiled.

After a few hours of music, samplers and drinks, the raffle begun and the prizes were given away. The MC was an older gentleman with salt and pepper hair and a gentle smile. Hailey thought he was handsome and that some woman was very lucky. That is until she noticed the young man with brown hair helping him and realized that it was some man who was very lucky. She giggled softly as she was impressed with this couple not being afraid to be themselves. The first few prizes went quickly and several people were excited to win the CDs, the movie tickets, and the gift cards for dinner at nice local restaurants. As the evening progressed, the more expensive prizes started to come up including a weekend in Las Vegas and the grand prize, a three-week all-inclusive beach trip at a five-star resort Hailey had never heard of before.

The weekend in Las Vegas went to a young couple who had just gotten married, and they joked it would make a nice honeymoon. Hailey was happy for them and knew the person who'd win the grand prize would have a fabulous time. "And now, for the prize we've all been waiting for. A three-week, all-inclusive stay at the five-star Regale Litore Maris thanks to the generous donation from the Talbott Corporation. The winner is... ME!"

The audience all laughed. "Just kidding folks. Okay, seriously now," he said as he reached into large bin of raffle tickets. "The real winner, the lucky person who will get three wonderfully fun-filled weeks for two to work on their tan is... Hailey Davidson!"

Hailey made the mistake of taking a drink when her name was called and instantly began to choke. Her co-workers all began to scream and cheer at hearing Hailey's name. Once Hailey could breathe again, and regain her composure, she walked up dumbstruck. The audience applauded as she received her prize. It was some time before Hailey could rejoin her friends as there were publicity pictures that were taken with all the lucky winners.

When Hailey returned to her co-workers, she felt sick. It hit her while her picture was being taken that she'd have to give up this amazing prize as she couldn't afford to pay the taxes on it. "Congratulations Hailey!" said Millie.

"What a win Hailey!" said Barbara.

"What's wrong?" asked Kathi.

"N-n-nothing," lied Hailey.

"Hailey," said Millie, "you should be happy."

"Yeah I know but—"

"But what?" asked Barbara.

Tears welled up in Hailey's eyes. "I can't afford the taxes for this prize," she sobbed.

"There are no taxes," said the young man who was aiding the MC.

The women turned to see him standing behind Hailey. "What do you mean?" she asked, wiping her eyes.

"Mr. Talbott arranged to pay all the taxes so the winner could enjoy the trip and not be burdened. I thought you knew that. Same thing for the couple who won the weekend in Vegas. That stay is at the Talbott Tower. Mr. Talbott has been a big supporter of ours for many years. It's how we can afford so many nice prizes for our raffles and put on this amazing fundraiser every year. It was Mr. Talbott's idea to include the trip and pay the taxes and fees. He jokingly told us if he didn't the winner might not get the prize they were promised due to a lack of money."

Hailey wiped her eyes and blushed. "Forgive me for being so silly. I never knew twenty-dollars would win me such an expensive prize."

The young man smiled. "Sweetie, you've got nothing to be sorry for. Just go and have a wonderful time with your man, or your woman for that matter."

Hailey didn't know what to say. This was a trip for two, not one. "Oh... um... yeah... about that."

"Hailey's single," chimed in Millie.

"A single mother no less," said Barbara.

"Well I hope you can find a babysitter cause this is an adults only resort. No one under 21 is allowed."

Kathi laughed, "No worries there, her Eagle Scout is 18."

The young man's smile grew even bigger. "You raised an Eagle Scout? That's amazing! Come, meet my partner. He needs to see not all single mothers are scum."

The young man grabbed Hailey's hand and took her to meet the MC, and a few others. Hailey shared her story about raising her son without his father, but tried to keep it as polite as possible as she knew anything she said negative could hurt her son. The next day the local paper ran a story that said, "Single Mother Wins Big on Twenty Dollars." There was Hailey's story about raising her son Tim, putting herself though college, and won the grand prize on a twenty-dollar donation. It wasn't long before her phone started to ring.


"Hey big winner!" said her mom.

"We are so proud of you," said her dad.


"When is the trip?" asked Dad.

"I need to speak with my boss and schedule the time off."

"And three-weeks! Oh Hailey, this is just what you need," said Mom.

"And if anyone deserves such a trip it's you kiddo," said Dad.

"Well, I promise to let you all know when I leave."

"Is Tim going with you?" asked Dad.

"Can't," said Hailey. "It's an adults-only resort. He won't be 21 for another two plus years."

"Good!" said Mom. "You need some you time."

After talking with her parents, Tim called. "Hey Mom! Congratulations!"

"Thanks baby!"

"Listen, I am so stoked that you got this, which makes what I need to tell you a bit easier."


"Yeah. Coach says I've got a lot of talent and asked me and some other players to work a soccer clinic for some underprivileged kids this summer. It's a big deal for me to be selected as it usually goes to the juniors and seniors and rarely to sophomores. And, one of my teammates who lives up here said I can crash at his place. I met his family and they are totally cool with it."

Hailey gasped. She had assumed Tim would come home for the summer break, but now he had an opportunity to work with kids and teach them something he loved the most. "Do you want to stay?"

"Yeah Mom, I do. But only if you don't mind."

Hailey did mind. But she also knew that Tim would give this all up for her in a heartbeat so she forced a smile on her face and said, "I don't mind in the least son."

"Really Mom?"

"Really Tim."

"Oh, and the best part is I'll get paid. There's some foundation up here that pays for everything. That's why they hire us from the team, 'cause we're cheaper. And now that I've been selected, I'll be selected every year until I graduate unless I do something stupid and get disqualified."

Hailey laughed. Even at minimum wage, it was a great opportunity for Tim and she knew her Eagle Scout wouldn't do something stupid. "Well, what are you going to do with all your money hon?"

"Well, some of it will go to my friend's family to pay for my food."

"Of course."

"And I guess the rest I'll save for Christmas."

"Good plan son."


"Yeah Tim."

"Why didn't you say more about my father in that article?"

Hailey was taken back. "How do you know what I said?"

"I read it online. Look, I know he's a damn prick leaving us like he did. I also know he never paid a dime of child support."

"How did you know that?"

"I overheard you a few times with Grandma and Grandpa. Plus, some of the scout mothers talked about how hard you'd fundraise so I could go to camp. I didn't mean to eavesdrop, but I wanted to make sure they weren't saying cruel things about you."

"And were they?"

"Naw. They were nice ladies. They always praised you and said nice things."

Hailey smiled. "I'm glad."

"So when are you going Mom?"

"I'll talk with my boss first thing tomorrow and schedule the vacation."

"Great! Oh and one more thing Mom."


"Remember to practice safe sex. I don't need a little brother or sister."

Hailey gasped. "TIMOTHY!"

Tim laughed. "You'd tell me the same thing Mom!"

Hailey laughed, she knew he was right. "Fair enough son. I love you."

"I love you too, Mom."

Monday morning Hailey met with her boss who was already aware of her win. Since she had never taken more than a week of her vacation for summer camps with her son, and the occasional day here and there for other activities, that involved Tim, she had the time built up. They scheduled her to go during their slower time in June. Hailey discovered that since she was going alone, her plane ticket was upgraded from two coach seats to one first class. The ladies who had taken Hailey to the event, took her shopping. Finding shorts and tops were easy, but the quest for a nice bathing suit was less than enjoyable for Hailey. Though she was an attractive blonde with big blue eyes, she was also petite and very curvy. She didn't want a bikini as her stomach was covered in stretch marks from having Tim, and she wanted something that would flatter her curvy figure and petite frame. They found a nice floral suit with a matching pair of shorts that did the trick.

June came quickly and Hailey had her parents take her to the airport. With the first class ticket, she was able to sit in the exclusive first class lounge where she enjoyed a cold drink while she waited for her flight to board. The majority of the people in the lounge were businessmen in expensive suits and Hailey felt out of place in her green shorts and dark pink blouse. She chose this as it was comfortable and she was facing a lengthy flight with two layovers. The first leg of her flight she sat next to a businessman who spent the bulk of the flight with his face buried in his laptop. The second portion she sat next to a woman who complained about everything. Hailey knew this woman had no clue how good sitting in first class was, especially compared to coach.

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