Hailey's Vacation free porn video

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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.

“Hello?”

“Hey big winner!” said her mom.

“We are so proud of you,” said her dad.

“Thanks.”

“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.”

“Oh?”

“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.”

“Mom.”

“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.”

“What?”

“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.

The final stretch that would take her to the island, she found a handsome young man sitting in her seat. “Excuse me,” she said politely. “But I think you’re in my seat.”

The man had black hair and the most amazing green eyes she had ever seen. He was wearing a green Hawaiian floral style shirt that complemented his eyes and khaki shorts. He smiled at her and said, “Really? Let me see your ticket.”

Hailey was hesitant to let this handsome stranger take her ticket when the flight attendant walked up and asked, “Is there a problem?”

“I think this gentleman is in my seat,” said Hailey.

“May I see both of your tickets?” she asked.

Hailey handed the woman her ticket and the man did the same. “Ah yes, Miss Davidson, you are mistaken. This is his seat, yours is behind his.”

Hailey blushed. “Oh, forgive me.”

The man’s smile lit up his face. “Nothing to forgive. It’s an honest mistake and you weren’t even rude about it.”

“It happens all the time Miss Davidson,” said the flight attendant as she returned their tickets.

Hailey sat in her seat and stared out her window when she noticed a shadow over her. She looked up and saw them man she accused of taking her seat staring down at her, smiling. “We were never really introduced. I’m Rick.”

Rick extended his tanned hand down to her. Hailey reached up and said, “Hailey.”

When their hands touched, Hailey was sure she felt sparks. She also noticed the faint scent of his expensive cologne. “Is this your first flight?”

“No, my third today.”

Rick laughed. “I mean, your first trip by plane.”

“Oh, no. But it is my first time in first class.”

“Oh? Win the lottery?”

“Kinda,” giggled Hailey. “I won a trip for two, but since I’m a one, they up graded my ticket.”

“A beautiful woman like you, single? Oh now that’s a crime.”

Hailey blushed at the complement. “Excuse me sir,” said the flight attendant. “I need you to take your seat now.”

Rick smiled. “We’ll chat after we’re in flight. That is, if you’d like.”

“Sure,” said Hailey. “That would be nice.”

Rick sat back down. The flight attendant went over their normal safety spiel and soon the plane was in the air. After a nice meal, Rick stepped around and sat in the empty seat next to Hailey. “So now, where were we?”

“Do you fly often?”

“Yes, my business requires me to fly to different locations all the time.”

“So are you working now?”

“No, now I’m talking to you.”

“No, I mean—”

“I’m teasing,” chuckled Rick “Actually I’m starting a well-deserved vacation.”

“Oh? Where are you going?”

“Regale Litore Maris.”

“Really? Me too!”

“Small world. How long are you staying?”

“Three weeks.”

“You won a three week stay at Regale Litore Maris?”

“Yeah. It was a prize at a charity raffle.”

“How much were the tickets?”

“Five dollars. I bought four as I only had twenty bucks. I found out later my co-workers had put my name on all their tickets except one or two each so it would increase my odds of winning.”

“Nice co-workers.”

“Yeah, they’re great friends. I offered all of them the second ticket, but they’re all married and their husbands didn’t want them to go without them. So, here I am alone.”

“Lucky me then.”

Hailey blushed. “What’s your story? Are you married?”

“Divorced. My wife and I realized early on we weren’t in love and to stay married for the sake of a child is never good. I see my daughter every chance I get. Another reason I fly so much. She’s in her high school’s marching band and they compete all the time so I fly out to see her competitions.”

“Are they any good?”

“Amazing. They win in their division all the time. She’s already received several scholarships and offers for college, though she doesn’t need the scholarships, I can more than cover her tuition.”

Hailey shook her head. Where was this guy when she got pregnant with Tim? Why couldn’t her son’s father be more like this man who obviously puts his daughter first? “How old is your daughter?”

“Fifteen. She wants a new car but her mother and I think a nice used car will be better. Teenagers with new cars are a formula for disaster.”

“My son is eighteen and he drives my old car. I have my mom’s old one and she bought a new one.”

“Why didn’t he get your mom’s?”

“My mom’s car is older and not as big.”

“Big?”

“My son is almost six feet tall and my mom is short like me.”

“Oh, it’s a small car then.”

“Yeah, a very small car. But it’s cheap on gas.”

“I hear ya there. Where’s your son now?”

“College. He’s working with some foundation to teach poor kids how to play soccer.”

“Very cool. So what was your old car?”

“A small SUV. I got it after my Saturn was stolen. I needed it with my growing boy scout.”

“Your son was a boy scout? That’s cool. How far did he get?”

Hailey grabbed the charm around her neck and said proudly, “Eagle. See, this is my Mother’s Eagle Pride necklace he gave me for Mother’s Day.”

Rick leaned in and smiled. “I see. That is something to be very proud of. Is he your only one?”

“Yeah.”

“So how long have you been divorced? Or are you a widow?”

Hailey sighed. “I was ... um ... never married.”

“Oh.”

“Yeah, his father left me when I was pregnant and basically disappeared.”

“So, he’s never seen his son?”

“Not that I know of.”

Rick shook his head. “I couldn’t imagine not knowing my daughter or not having a relationship with her. Mind you, I don’t see her as often as I’d like, but thanks to things like Skype, I see more of her now than ever before. So, you raised him alone?”

“My parents helped.”

“What about his family?”

“They want nothing to do with me or my son. They think I got pregnant to trap his father.”

“Did you?”

Hailey was taken aback with that question. “No!”

“Forgive me for asking. I didn’t mean to offend you.”

Hailey sighed. “Sorry, it’s just I’ve been accused of it for so many years, and you’re the first person to ever ask.”

“Well, you don’t look old enough to have an eighteen-year-old son. You must have been pretty young.”

“I was almost 21.”

“Wow.”

“Excuse me sir, we need you to fasten to your seatbelt as we’ll be landing shortly,” interrupted the flight attendant.

“Yes, of course,” he said. “Hey, when you get to the resort, ask for the acupressure massage. It will cure your jetlag. Trust me; I get it every time I go there. Look as much as I’m enjoying our chat, I should probably return to my seat and gather my things for when we land.”

Rick stood up as Hailey asked, “Do you go there often?”

“Yeah, at least once a year. I’m sure you’ll have a wonderful time. Maybe we can have lunch together while you’re there.”

“That would be nice.”

Rick returned to his seat and soon the pilot announced they were about to land. Hailey’s excitement grew as she looked out the window at the blue ocean water. The plane landed and she noticed Rick quickly left the plane. She felt disappointed as she was hoping they could resume their talk. After making her way through customs, she gathered her things and found the bus for the resort. Standing outside the bus was a tall, slender black man with a floral shirt and green shorts. “Welcome ma’am. What be ya name?” he asked in a Jamaican accent.

“Hailey Davidson.”

“Ah jes, welcome miss. Take your bags for ya I will. Go and find youself a seat.”

“Thanks.”

Hailey stepped onto the bus and was surprised to not see Rick. She sat in the front row hoping she’d see him board and maybe they could resume their conversation. A few other couples boarded the bus, but there was no sign of Rick. Then a handsome man with black hair and tanned skin wearing a black suit stepped onto the bus and asked loudly, “Is Hailey Davidson on board?”

“I’m Hailey.”

“Come with me ma’am.”

Hailey was confused. “Is something wrong?”

The man spirited off the bus and a confused Hailey followed. Had there been a mistake? Was this trip a joke and she was to be sent back in coach? The bus driver smiled and removed her bags from the bus’s cargo hold. “Hey! Those are mine!”

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We were finally winging our way to our tropical get away. Since, from our northern location, its nearly a five and a half hour flight we had splurged and used airline miles to upgrade to first class. But let me go back and start at the beginning. Lisa and I both work pretty hard and our major payback to ourselves is a vacation at a tropical resort each year. After alternating between the Caribbean and Hawaii for years, we decided to try the Mexican Riviera this time. If you have been...

4 years ago
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Hotwife Brandis Slutty Vacation

Chapter 1“Could you take my case downstairs to the hall please, hon? It's a bit heavy!” asked Brandi.“How can it possibly be heavy?” I asked, with a grin on my face. “All your outfits are so skimpy, they don'tweigh any more than a few feathers!”“Oh, very droll, darling! I've got 3 pairs of kinky thigh boots in there, as well as those pvc chaps that you likeso much!”Brandi had started packing for our vacation almost a week ago and I knew that she would be taking someseriously slutty outfits. She...

2 years ago
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Cucked on Vacation

It was our first proper vacation in years. I breathed a sigh of relief as I gazed out our suite window towards the calm ocean waters of the gulf. After seven years of marriage and a limited amount of time off it felt the****utic to finally have a week away all to ourselves. We had selected Naples because it was quiet, and peaceful, and a drastic change of scenery from the drab winter we had just suffered through in Ohio. I turned and looked towards the bed, where my wife rested in slumber....

2 years ago
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Once In A Lifetime Vacation

Introduction: Husband and wife go on a Florida vacation leasing a beach house for the entire Month. Their twelve year old daughter is to join them for the last two weeks. This totally fictional story is written by a complete novice from his infertile mind! I make up stories for my own entertainment! If I were a professional writer, Id have a lot more money in the bank! Stan-Husband Debra-Wife Cassie-Daughter, Seventeen yrs. Todd-White stranger David-Black stranger This story is told from the...

4 years ago
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A Kinky Vacation

After 3 years without a vacation for ourselves, my wife and I were finally able to book a cruise in the Caribbean for an entire week. It was to be a much needed break from a stressful job and the full time 24/7 commitment of being parents. I was also hoping that it would be an opportunity to spice things up a bit. Our sex life wasn't bad, but the commitments of work and family rarely left us with the time and energy to play. Even then, we had gotten into a rut of doing pretty much the same...

3 years ago
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Sexy Cuckold Vacation

After 3 years without a vacation for ourselves, my wife and I were finally able to book a cruise in the Caribbean for an entire week. It was to be a much needed break from a stressful job and the full time 24/7 commitment of being parents. I was also hoping that it would be an opportunity to spice things up a bit. Our sex life wasn't bad, but the commitments of work and family rarely left us with the time and energy to play. Even then, we had gotten into a rut of doing pretty much the same...

3 years ago
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Charlottes Vacation

Here we are, the middle of Summer. The peak of blazing hot weather. The sun cooking people who dared to step outside into Mother Nature's oven. People walking the streets with uneven tans, some wearing sunglasses too big for their faces, people splashing around in pools in their backyards, unattractive men jogging in short shorts hidden behind their huge hairy bellies. It was a perfect summer day, and also the day before the vacation of a lifetime.It was a Friday night and I was packing my bags...

Supernatural
2 years ago
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Once In A Lifetime Vacation

Stan-Husband Debra-Wife Cassie-Daughter, Seventeen yrs. Todd-White stranger David-Black stranger This story is told from the view of the wife, Debra. Once In A Lifetime Vacation My husband, Stan and I were on the Florida coast for a long rest and well deserved vacation. We both have been working hard and in a welcome turn of fate, we both had slack time at work and could get vacation at the same time so we could take off together for the first time in years. We took a month’s...

1 year ago
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Accepting My Cuckold Role On A Houseboat Vacation

It was a culture shock moving to Boise, Idaho to attend Boise State University, after being born and raised in a small town in Nebraska, but that’s where I wanted to go to pursue my education for a career in the high-tech industry. I was in the top of my class in high school and studied hard to handle my double majors in electrical engineering and computer engineering.My name is Matt, and I became good friends with Ken and Dave, two boys from small towns in Idaho, since we began college at the...

Cuckold
2 years ago
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What I Did on my Vacation

Chapter 1 Day One I AM ON VACATION I AM ON VACATION I AM ON VACATION!!! This one thought cycles through my head as I pack my overnight bag with only the essentials for the next ten days. Toiletries, brush, makeup, minimal clothing - didn't need much on the beach. No man to impress. No kids to tell me how dorky I look. Only four hours to go. Drive an hour to the airport from my podunk little town in this frigid northern climate then board a plane for sunny Florida. I even got a direct...

3 years ago
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Winter Vacation

There are eight of us. There is my wife Lauren and three of her sorority sisters and me (I’m Al) and three of my fraternity brothers. We all graduated within a year of each other and we all got married within a couple of years after college. We have been fast friends ever since. Every winter we all go on vacation together. We have been to exotic islands, rented houses large enough for all of us on some of the best beaches we can find but this year we had decided to do a winter vacation in a...

1 year ago
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Susan is tricked into taking a 8220swinger8221 vacation

“James and Susan Hullett. That’s H.u.l.l.e.t.t” I said to the pretty red head behind the ticket counter. “Here you are sir. Here is your boarding pass and seat assignment,” she said as she passed me my tickets and smiled. She looked to be about 22 or 23 and I couldn’t help noticing she had either very perky breast or a great push up bra. They were standing hard and proud. She noticed I was looking and her hand instinctively went to her cleavage and...

2 years ago
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It Happened on Vacation

Chapter 1. While in the car on the way to the mountains for our family vacation my thoughts drifted to what I would be missing for the next week, namely my girlfriend or in other words doing without sex for the next 9 days. When your in your teens you know how it is having to cope with the urges so you masturbate a lot and when you do finally have sex all you think about is the next time. Here is the problem: My parents rented a couple of small camping cabins, they stay in one and I will be...

3 years ago
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My Wife8217s Friend Radhika And Our Vacation

Did I ever tell you that I and my wife have a unique relationship. ? In fact that was what brought us together. We met as working adults and became friends and soon there was no subject we did not discuss or argue about. She was an air hostess and keen to pursue her career, see the world. She also said that her job meant being away from home, having temptations like a normal human being but said that she had never met a man who would accept that. She said that while a man never thought twice...

1 year ago
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Dream Vacation

This story draws on a conversation 'driving home from the Cartwrights' I sketched several years ago, forgot, partly used in "Coupled," then forgot again. I'm embarrassed to see I used some of it here too. With a different POV and leading elsewhere, but still, if a few lines of dialogue early in this story seem a little familiar, that's why. That's not why, as some observe, my other stories also somewhat resemble each other. The reason for that is, I like them that way. ...

2 years ago
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My Florida Vacation

MY FLORIDA VACATION What a bore. This job sucks. For a long time, it has made me depressed and frustrated. Sales were down all over and cutbacks in travel to meet old customers and generate new ones were limited. I was bored and angry, aware that there was no possible improvement in sight... My commissions were almost non-existent. I'd like to open up an artery or something. Business is soooo bad, but even when business is good, the job and the boss suck. I brought a lot of this job...

1 year ago
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Girls Getaway Vacation

Girls Getaway Vacation Friday. I climbed out of the shower and toweled off. "See any stray hairs I might have missed?" I asked. Geena looked over my naked body and then ran her fingers down my chest to my waist. "Looks god to me. Aren't you glad we had you shave all that hair off?" "Absolutely," I agreed. I looked her over, she was putting on makeup standing there in just a bra and panties. "I also like that you are wearing sexier underwear." I traced along the lace front of...

3 years ago
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Our Jamaican Vacation

Disclaimer* The following story is a work of fiction. It has strong sexual content and some of the material may be offensive to some. I hope those that do read it and enjoy it will comment or contact me if you would like to offer any feedback. All the photos except the first two shown at the end are not ours, and are only offered as visual aids to add to the story’s experience. I hope you enjoy! JAMAICAN PLEASURE - My wife and I have always loved to travel. We like to explore...

1 year ago
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Summer Vacation

Chapter 1: First Day My wife really wasn't a prude, I would call her extremely conservative. She was a beautiful woman when we married and she has not lost her beauty. Our marriage of fifteen years has been a good one; I have no complaints, other than Mary being conservative. When I say conservative I mean it and every sense possible, grocery shopping, automobile purchases, necessities for the house and our clothing. Its true, our savings account is much fatter under her guidance where it...

2 years ago
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An activity that wasnt planned on our vacation

I hadn't looked forward to a vacation like this in a long time. Yes, I'd gone on vacations with my wife and kids. Yes, I'd had a pretty good time. Yes, I'd been lucky enough to go different places around the country. But this was different.I was excited because I was going to a vacation spot I'd been to a number of times, staying in a cabin in the mountains. Being outside in the beautiful weather in Tennesse. And most importantly, being in the mountains. It was one of my favorite places in the...

Teen
2 years ago
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Shelbys Dirty Vacation

“You’re such a whore, Shelby! But that’s still fucking hot…” Chelsie said as I briefly mentioned one particular aspect of my vacation to the Cayman Islands. “How were they? Big? Muscular? Come on, Shelby, details!” “Geez, let’s not be too demanding here. It was just sex on the beach with three incredibly hot guys! After all, I was on vacation…” I just stared at Chelsie, hoping she wouldn’t judge me for spilling the contents of my wild and dirty vacation. “Oh, please do tell! And you couldn’t...

Group Sex
3 years ago
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Cuckold Adventure Vacation

Let me just say that I had never really had a threesome before all this happened. I also can't say that I thought about my wife, or my girlfriends before that with other men either. After what happened to us last year though, I don't really know...I had what you would call a totally normal relationship with my wife Jennifer. Boring name, I know, but not a boring girl. We had gotten married soon after I turned 24, and I was working on Wall Street. I was doing really well, and my wife was totally...

1 year ago
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Shellys Vacation

I was so bored. It seemed nothing was happening where I lived. During the summer it hadn’t been so bad with lots of boat activity on the lake. But, after that, nothing. It’s a dull life.  I was restless and knew I had to do something or I would scream and go mad. A light came on. I decided to take a vacation. I had no idea where I would go but I knew I had to get away from this dead zone. So I packed a suitcase and, the next morning, I told my room-mate I was going on a vacation. She asked...

Straight Sex
2 years ago
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A free Vacation

byjealouscuck©The first full night there, the men had the opportunity to fuck their wives. As with Dan, the guys had no idea that unless something out of the ordinary happened, they would not be fucking them for the duration of the vacation. Dan was definitely turned on watching Valerie dancing so closely with her dance partner. Obviously, she was equally aroused and ready to fuck. The other guests were there and watched the interaction of the white wives with the black men. Several of the...

3 years ago
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What a vacation

We always had a great sex life. We liked all kinds of sex. Toys, role playing, anal sex, the works.We even liked to fantasize of having sex with the same sex. My wife told me maybe this year on vacation we would be able to fulfill a fantasy or two. Boy I sure hoped so.We left late and drove late into the night. It was about midnight when we stopped at a rest area. No one was there when we stopped. We got out and used the restrooms. When we got back to the car Sue, my wife, reached over and...

3 years ago
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The Vacation

The Vacation**I and Nadiya and her husband have been talking for a little over a year. As well as exchanging emails and photos. We decided to go on vacation together and for them to come to the United States. We agreed to meet and rent a beach house just north of Bangor, Maine. They were so excited about their first trip to the states.**** When they arrived they went to retrieve the rental car. We met at one of the stores I researched and found so she can buy her some sexy clothes. I called...

4 years ago
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The Big Vacation

Straight out of high school, I went to work as a rodman for the state. The time? Set it as 1980. I had been working as an assistant surveyor for 24 years with never a day off for sick time or vacation. The legislature decided in their wisdom that accumulations of more than 4 months combined sick and vacation would be forfeit if the employee didn't start using the time before the beginning of the fiscal year 1981. Several of my peers had retired with 26 years and used their accumulated time to...

1 year ago
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What a vacation

We always had a great sex life. We liked all kinds of sex. Toys, role playing, anal sex, the works.We even liked to fantasize of having sex with the same sex. My wife told me maybe this year on vacation we would be able to fulfill a fantasy or two. Boy I sure hoped so. We left late and drove late into the night. It was about midnight when we stopped at a rest area. No one was there when we stopped. We got out and used the restrooms. When we got back to the car Sue, my wife, reached over and...

Bisexual
3 years ago
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looking back vacation

aThe internet opened up whole new worlds for people, myself included.My first pc was put together from spare parts collecting dust in a friend's garage, he brought it over to the house showed me how to put it together and loaded and aol trial disk. That's all it took. The worldwide web was now opened to me, including porn, of course. The biggest thrill was when I figured out how to get in gay/bi chat rooms and use instant messenger.Dating sites had my attention also. I loved being able to...

3 years ago
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My Wife Her Bull THEIR Vacation

If your read my last story, "Our First Night In The Cuckold Lifestyle", you were introduced to three characters. My wife, Liz, her bull, Darren, and myself. You can read up on all the details about us in that story. If you're still reading to this point I assume you're all caught up and ready for this story.This takes place last summer. "But honey you promised you were going to be able to get off work for our beach vacation next week?", my wife, Liz, asked me. I felt terrible--honestly I never...

4 years ago
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Colorado Vacation

Colorado VacationI grew up in a small town in Texas on the gulf coast and worked hard for everything I had to my name. Mom was widowed when I was s*******n and I stayed at home with her to help pay bills and take care of the forty acre property we lived on. I dated girls my age, but they were never what I wanted as I would go out to the over forty Country Western club and dance there. I was now twenty two years only, six foot tall and well muscled from hard work. I had saved up for several...

3 years ago
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Having A Swinging Adventure On Vacation

My husband and I are swingers. We've been married for the last twenty years. We weren’t always swingers, but after our children left to go to college, we became empty- nesters. We were looking for other ideas, and when we went on vacation, we met two very interesting people, who were living the swinging lifestyle.We really enjoy meeting people and having sex all together. It's very erotic to watch each other have sex, with somebody else. We both get very excited, when we're hooking up with...

Swingers
4 years ago
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The Way to Start a Vacation

It all started a few hours ago. Violet and I had just got off the plane and had walked into the terminal when the realization that we were on vacation sunk in. After reaching baggage claim and waiting what seemed like an hour or two for both of our bags, we walked out onto the sidewalk. Then another hour or two seemed to pass as we flagged down a cabbie and made it up to our rented flat for the next month or so. As we walked through the door on the top of the stairs, I finally sat down on the...

Group Sex
2 years ago
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Beach Vacation

I don't know how many of you have read about the skiing vacation I took lastlast winter. It was a rather boring until my boyfriend Dave and his friend Jimdecided to do some very kinky things to Jim's girlfriend Cathy and me, ofcourse. None of the individual activities were new to me, but the combinationof things did get me very excited. Cathy on the other hand was quite innocentof these kinky entertainments. The vacation turned out to include her firstassfuck, her first time naked in front of...

2 years ago
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The Vacation

IntroThis story is about a lustful encounter in one of the most peaceful countries in the world, Costa Rica. Known for its amazing tropical forests, gorgeous beaches, and beautiful women. A fantasy about your average male tourist and a beautiful young local lady. An unforgettable connection and the most amazing sexual adventure to experience... Enjoy!Summer is near, and the exhaustion from work and life is taking a beat out of me. Its early June of 2015 and I decided that I needed a vacation!...

2 years ago
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Beach vacation

I don't know how many of you have read about the skiing vacation I took last last winter. It was a rather boring until my boyfriend Dave and his friend Jim decided to do some very kinky things to Jim's girlfriend Cathy and me, of course. None of the individual activities were new to me, but the combination of things did get me very excited. Cathy on the other hand was quite innocent of these kinky entertainments. The vacation turned out to include her first assfuck, her first time naked in...

4 years ago
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The Vacation

I recently ended a relationship with my boyfriend. I have been feeling down and booked a vacation to cheer myself up. I am going to St. Lucia to an all inclusive resort. I cannot wait to go. The door bell is ringing, and transportation is here to take me to the airport. The driver puts my luggage in the trunk, and I sit in the backseat. I close my eyes, and take a nap on the way to the airport. When we arrive at the airport, I get checked in, and go through the necessary security checks. There...

Group Sex
2 years ago
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The Surprise Vacation

The Surprise Vacation by an unknown author and Tristmegistus 1. Chapter - Innocent Beginnings "Did you take your vitamin, dear?" Ellen called from the bathroom. I rubbed sleep from my eyes and picked up the pill bottle, rolling a bigtablet into my palm. "My horse pill? I'm doing it now." "Have you noticed any difference yet?" "Nah. Vitamins are pretty much all alike." She'd gone on a minor healthkick a month before, insisting that I needed to lose a little weight andtake better...

2 years ago
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Ritas vacation

There's a picture out there posted by the username : smithmp12 in his gallery titled Mom sexy pics, photo # 4 (or all of them for that matter). In fact that reminds me of a vacation I took once with my aunt Rita. That looks so much like her that I'm tempted to say it IS her, but I really know it is not. Go take a look b.o.y.s and g.i.r.l.s it is worth the detour.Rita is my dad's sister and when my mom died in a car crash she almost took over the mom duties - except for taking car of my dad, I...

3 years ago
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What I Did On My Summer Vacation

WHAT I DID ON MY SUMMER VACATION. BY JANICE My name is Ross, I am sixteen years old, and due to a bout with Scarlet Fever when I was young, I stand four feet eleven and a half inches tall and weigh in at just less than one hundred pounds. To add to my problems, my mother has a few brain cells missing and for some reason known only to her she has been dressing me as a little girl since I can remember. I liked wearing...

4 years ago
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Sexciting Goa Vacation

Hi friends, I am Bikash again to tell you another story. I have been writing for ISS for quite some time and thanks to your hundreds of mails and I am getting inspired to write more and more stories. If you find this story nice do please mail me at This happened a few days back on a vacation when I went on to visit the beach capital of India, Goa with my family. We were not alone as we were going there with a big group of known and unknown people, which included Lina. She was newly married and...

Incest
2 years ago
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Blacken Vacation

My two-week vacation had just begun alone in The Dominican Republic without my husband Carter. While I was happy to be on vacation, I couldn't really believe I was here without him.Our fight started when Carter came to me two days before we were to arrive in The Dominican. He nervously told me we would have to move our vacation because he needed to go on a business trip the same day we were to leave. The fight ended with me angrily telling him I was going without him.Here I was in my hotel...

2 years ago
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Island Vacation

Welcome to the next multi-chapter story! Like Mistaken Identity, you will find chapters alternating between two protagonists: Stanley and Delphina. Unlike MI, I won't do chapter 1A and 1B, instead I will simply tell Stanley's chapters in the odd numbered ones, and Delphina in the even numbered ones. Disclaimer: This story is my intellectual property, and should be treated as such, do not plagiarize, or post without permission. If it is not legal to view writings that are sexually...

2 years ago
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Family Vacation

It must have been an alignment of the sun, moon and stars otherwise I don't know how this could have happened. It was early July and as such it was time for our annual family vacation. My husband Bill had made the reservation for the beach house months ago and as it happened my daughter Elizabeth had found a new boyfriend towards the end of her sophomore year, a young man named Josh who was a junior at the same high school. By the time the summer finally arrived they were going steady and she...

1 year ago
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Vacation

Vacation! God how long has it been? This will be wonderful ... going to a romantic place with the man you love and - for a whole week - you don't have to cut up anyone else's meat ... no bedtime stories (unless you count the Penthouse Letters.) No hurt knees or feelings to soothe. Only you and Michael and your fantasies. You got lucky; the plane isn't crowded. You settle in - Michael by the window, you by the aisle and no one in between. The plane takes off and Michael lifts the armrests...

4 years ago
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The SmithChapter 16 Vacation

“Master?” asked an uneasy teen. “Yes?” “Rachel. I’m not sure I understand why she was included in my torment.” “It seems Rachel is similar to you in some aspects of behavior. Her grandmother wanted to send a message that got out of hand with Moria’s inclusion. “Rachel was really worried about her job.” “You can tell her that she has nothing to worry about. Moria never mixes business with pleasure. She will treat her as she always had. But will take note if something unexpected happens...

1 year ago
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I guess I really DID need a vacation

Being alone is all right. Sometimes, it's preferable to being with people who bore you or annoy you. Sometimes you just want to be alone. That's okay. Everyone needs a little space now and then. But I had been alone for a year. My solitude had progressed into abject loneliness, and it sucked. I decided to treat myself to a summer vacation. I was going alone, but, hopefully, a change of scenery would help. When the initial anger of my breakup with Karen faded, being alone was...

1 year ago
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Precious Gem Twin Sisters Ch 6 On Vacation

Well after the Sybian Night at the strip club success, the owner begged us to do another due to demands from customers, so we did another but featuring Diamond as the center of attention, and we pulled nearly $40,000 profit for ourselves that night, a couple weeks after the first one. We also came up with plans to have a monthly 'party' that guaranteed me a nice monthly bonus, so i was looking forward to hosting that. The girls and I ended up booking a 3 week vacation at a big resort in...

1 year ago
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David Takes a Vacation

Master PC: David Takes a Vacation At the urging of my assistant, Julia, I decided to take a vacation. I own points in a resort system, and it seemed likely that a couple of weeks in Florida’s sunshine would do me no harm. ‘Who knows, boss,’ Julia said, laughing, ‘maybe you’ll get laid.’ So, that was how I had come to be strolling through the gate to the ‘quiet pool’ at the Tuscany Village in Orlando. I had a copy of the third volume of ‘The Last Chronicles of Thomas Covenant’ in one hand...

4 years ago
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Charlottes Vacation

Here we are, the middle of Summer. The peak of blazing hot weather. The sun cooking people who dared to step outside into Mother Nature’s oven. People walking the streets with uneven tans, some wearing sunglasses too big for their faces, people splashing around in pools in their backyards, unattractive men jogging in short shorts hidden behind their huge hairy bellies. It was a perfect summer day, and also the day before the vacation of a lifetime. It was a Friday night and I was packing my...

1 year ago
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Jamaica Vacation

While watching interracial porn, where white ladies on vacation in Jamaica were long dicked by natives, my girlfriend Cindy admitted to me that she had been fucked by a black guy while in high school. After watching the porn, she related the following story to me.She told me a black guy would catch her alone and repeatedly tell her he was going to fuck her. The rumor around school was that he was on a quest to fuck as many white girls as possible. Rumor also had it that he had been very...

Interracial

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