Singles On The Seven Seas Pt 01

***A note from the author: The people in this story and the story itself are complete fiction. All characters are over the age of 18. These people are not real and the events are not real. Any likeness to anyone or any situation in real life is pure coincidence. ***

6 Months Earlier:

Jake

He sat on his bed, at 11 pm completely drained, but somehow unable to sleep. His laptop on his lap, with the screen glowing brightly as he scanned travel sites trying to find something that would give him an opportunity to relax, let go and maybe- just maybe meet someone to go on future trips with.

Since his divorce 6 years ago, he had traveled with friends, family and co-workers but he hadn't taken a romantic interest- not even a fuck buddy on a trip to anywhere. He missed traveling with a partner. He clicked through travel sites which told him to go to Arizona, Texas and Mexico- probably because he had booked trips to go there for Dune Buggy riding with his buddies in the past through that same site. Too hot, without relief. Then, the site told him to go to the mountains of Ireland- or more locally, he could go to Colorado, Yellowstone, Yosemite. Again, the site algorithm was remembering the last family reunion when everyone rented a giant cabin in the heart of Montana. The view was beautiful, the family drama was not. Also, it was lonesome up there. Which normally wouldn't be a problem, he was a bit more of an introvert than anything else, but he didn't want to be alone this time. Too solitary. Then, the site showed him travel packages for Clearwater, Myrtle Beach, Gulf Coast and San Diego. He enjoyed his beach trips with friends and family in the past. In fact, the beach was kind of an important place for him. He was raised off the Florida coast, raised his kids and the first good years of his marriage there. The beach was nice. Getting closer... He clicked over one more link and saw a perfect solution. SINGLES ON THE SEAS SUMMER CRUISE. A 5-Day/4-Night cruise around Florida and the Gulf. Only singles allowed on board. Passengers filled out a questionnaire, and they were matched with their perfect partner. They still booked their own rooms, no one forced them to room together. Then, they participated in activities, got to know each other and at the very least, they might leave with a good friend at the end of it. He wasn't much of a cruise person, he usually preferred to drive his own smaller boats, but this seemed almost perfect. A fun trip, with an opportunity to meet someone.

The only downside was the timing. The cruise was July 20 through July 25- his oldest daughter, Tessa's birthday was on the 23rd- so he would miss it. She was 22 now, he didn't need to schedule around her birthday- she didn't schedule around his, but he still felt bad for being out of town on those dates. He clicked the link to register anyway.

The questions at first were basic:

Name: Jake Williams

Age: 48

Sign: Libra

Height: 6'3"

Hair Color: Brown

Facial Hair: Yes, Beard

Body Type: Dad Bod (he had learned that term from his daughter).

Likes: Fishing, Photography, Painting

Dislikes: Smoking, Drinking

Then, the questions got a little more intimate:

Sexual Orientation: Straight

Ideal Age Range of Partner: 20-50 years old. (He tended to like being the older one, but he would make an exception for a few years, if he were the younger one).

Is religion important to you? No.

Are you looking for Friends, Dating, Committed Relationships, Marriage, Sex? Any.

Then, the questions got even more intimate:

Favorite sexual position? Girl on top.

Do you like to use toys in the bedroom? Yes, on her.

Common Fantasy you enjoy? Exhibitionism

Darker Fantasy you enjoy? Dad/Babysitter

The questions went on and on for almost an hour before he finally reached the payment screen. It said it was all-inclusive for a somewhat reasonable price. He also opted for a nicer room- he had no interest in being in a small cabin. He wanted something with big windows, so he splurged a little. He entered his credit card information and confirmed his information. He got an email with his confirmation codes on it and then, he closed the laptop and rolled over to try and sleep. Only problem now, he was excited about what might come of this.

Tessa

It was a little after midnight and Tessa sat awake on her bed, staring at her laptop. The curser blinked on a term paper without a single word on it. She was burned out. In desperate need of a vacation- a real one. During the last holiday break, she worked the entire time. It was time away from school, but it wasn't time off. She was just a different kind of busy. She needed to get away- it was winter now- not great vacation weather. But spring and summer will be here soon. Earlier that week, her roommate- and best friend, Allison told her about a cruise she was taking in July. She offered to pay for her ticket and everything. Allison was rich- well her family was rich. They gave her unlimited credit cards when she came to college and she spoiled Tessa a lot. If they went anywhere together, Allison paid. Tessa's parents raised her to save her money and earn her way. Allison didn't agree.

Tessa sighed, looking at the blinking cursor again. Frustrated, she closed the word document, and went to the link that Allison had sent her earlier that week. The cruise dates were during her birthday. Perfect. That was the final straw for her, and she started to book her room. She booked her regular room; she was okay without the luxury- she liked luxury but could live without it. How long would I even be in the room? She thought to herself. It was a cruise, there were activities and bars and lots of stuff to do outside of the room. If she met someone, she would just go to his room. She giggled to herself at the prospect of having a room and never being in it. She got to the question-and-answer part of the application and filled it out as well. At first, the questions were tame and then they got a little spicier.

The questions at first were basic:

Name: Tessa Rose (the name she always preferred- She liked her mom's maiden name more than her dad's last name).

Age: 22

Sign: Leo

Height: 5'5""

Hair Color: Brown

Eyes: Blue

Body Type: Curvy

Likes: Art, beaches, horseback riding

Dislikes: Smoking

Then, the questions got a little more intimate:

Sexual Orientation: 60% Straight

Ideal Age Range of Partner: 30-50 years old.

Is religion important to you? No.

Are you looking for Friends, Dating, Committed Relationships, Marriage, Sex? Any.

Then, the questions got even more intimate:

Favorite sexual position? On my side or shower.

Do you like to use toys in the bedroom? Never have, but I'm open to it.

After all the questions had been answered, she put in Allison's credit card info.

Flash Forward:

Present Day

Jake

When Jake arrived at the check-in spot for the cruise, he was greeted by a very attractive blond in a SINGLES ON THE SEVEN SEAS polo and a name tag. Katie. If everything else failed, at least he might get to look at her during this trip. He gave her his name and she gave him a token that had the number '44' on it. Two younger men picked up his luggage and put it on a cart at the front door.

"They are going to take your luggage to your room. Here is your keycard. Your room is on the Emerald Level, its room number 5. It will be ready in about an hour." She handed him his keycard and made a note with her well-manicured finger on the touchscreen of the tablet. Keep this number, the person we matched you with will have a matching number." She made another note on her tablet. "When you get onto the ship, show the hostess your number and she'll direct you where to go next." She made a few quick clicks on her tablet and looked up at him with a pleasant smile. "I hope you have a magical trip." She bit her lip and held his look a little longer than necessary. He smiled at her a little bit then forced herself to move on to the next guest. If that was the energy of this place, it will be a magical trip indeed. He walked up the walkway and got to the main door.

The hostess greeted him with a big open smile and a strong southern accent. "Welcome aboard, Mr..." She took his token and his ticket "Mr. Williams." She locked eyes with him, they were a warm amber brown on a small, delicate little face that he was instantly attracted to.

"Thank you, I'm happy to be here." She typed some information into her computer and then reached into the drawer toward the bottom of her podium. She pulled up a goodie bag full of stuff and handed it to him.

"As you will be our guest for the next 5 days and 4 nights, here is a pack of essentials you may need. The pools, game rooms, theatres and such will open in about an hour. We set sail in about 3 hours. For now, while everyone is boarding, you can lounge on the deck, hang out at the bar or walk around the ship and get comfortable here. At 5pm, you will go to the main dining room and go to table..." She grabbed his hand and looked at his token with "44" on it. "44. The person we matched you with will be sent to that same table. Tonight, you will have dinner with a total stranger, but statistically, they are your perfect match." That thought both excited and terrified him. She handed him the goodie bag, smiled and the doors opened behind her. "Have a wonderful trip, Mr. Williams. My name is Kendall, if you need anything, you can come to any of the staff members on board, and we'll get you taken care of."

He took the bag and walked through the doors behind her. He immediately walked into the lounge area. There was a huge bar that spanned the entire back of the hall. The main area had lots of pool tables, some lounging couches, t.v.'s and small bar tables and stools. It looked like an upscale bar in its décor. He saw a huge set of doors that led to the dining room, which was currently being set up. Then, he saw another set of doors that led to the boat deck. He headed that way. There were a lot of people around already. Small groups of well-dressed, attractive people were chatting around the bar, some were playing games, but it was mostly pretty quiet so far.

He made it to the deck, and he walked over to the rail. He took a little peak through his goodie bag. There were vouchers for drinks at the bar, some edibles, some condoms- which wouldn't fit him, some vouchers for snacks, desserts and non-alcoholic drinks, a map of the ship, and a complete list of every activity they could do, which were pretty much running 24/7 on different floors of the ship.

He looked to his left and right. Two very attractive older women met his gaze and grinned. He nodded to them and grabbed one of the deck chairs. He wondered if his perfect match was one of the people that were already here. He wondered what she might look like, or what she might be like. He was hoping for curves. He loved big hips, big asses, round and soft bellies, thick thighs. He was a very physical lover, and he liked his partners to have a body he could hold on to and take handfuls of. He reclined back in his deck chair and sighed as he looked out over the beautiful water. Even if this whole trip was a bust and he didn't meet anyone, he was still happy to be here on the water.

Tessa

In her small cabin room, she pulled and tugged at her light green sundress, and assessed her look in the mirror. The sundress had thin straps over the shoulders, a decently low-cut chest piece, that showed off her full cleavage. The mid-section was tight and form-fitting. Then, the skirt was loose, but hung in a way that was very flattering. She wore a pair of nude colored, open toed, platforms. She wore no jewelry- just in case they ended up wanting to go to the pool or the beach later. She opted to wear her hair down and her makeup light. She just looked like a usual college student. Somewhat innocent- but still 15% sex kitten.

She grabbed her room key and her little purse and checked the time. 4:50. She didn't want to be late or rude, but she didn't want to be early. She gave the room one more look, not sure if she would see it again after that night. The thought made her laugh, she would surely be back here tonight. She closed the door behind her and headed toward the elevator. They had put her on the 5th floor, which was okay. All the luxury rooms were on floors named after gemstones; she was just on a regular numbered floor. Allison was in the conjoining room and came out of her room just a second or two after Tessa.

"Are you ready to meet your perfect match?" Allison said in a sing-songy tone as she caught up to Tessa.

"Ready or not, its about to happen." Tessa replied through a little bit of a laugh. Allison immediately put her hands in Tessa's hair, that was her thing. She loved running her hands through her hair.

"I'm so nervous." Allison said in a whispered tone. She stroked Tessa's hair a little more urgently, like it was an emotional support blanket.

"I know, me too" Tessa whispered back. Tessa weaved her arm through Allison's, and Allison dropped her hair, and they continued walking together down the hallway together.

"Well, just remember, if your perfect match is a failure, you can always come share my bed." Allison giggled. Tessa laughed. They got in the elevator and began their descent.

"Well, I don't think you'll be alone. You look incredible." And she did. Allison had a look that always made Tessa jealous. She was thin, short and fucking adorable. She looked like a real-life anime character. She had a very cute, young look, small- but full breasts, bigger hips, cute features on her face, big blue eyes and she had super long hair that she usually wore in a series in intricate designs and lively colors. She liked to wear braids and use hair accessories. Currently, her hair was a pretty light blue color and cascaded down her shoulders. Allison turned Tessa's body toward hers and gave her a thorough look over. She pulled the chest piece of her dress down a little bit, straightened the skirt of her sundress and pushed her breasts up, so they bulged from the dress a little bit.

"We aren't picking up Church men tonight, Tessa." She said with a slight giggle. "But I meant what I said. I am here if this goes badly." She held Tessa's gaze just a beat longer than usual so she knew she was serious. Allison moved in close and kissed Tessa. It was an innocent kiss- but full of emotion.

"I love you too." Tessa whispered. It was true. Allison was a great friend, and if Tessa knew she would never miss men, she would probably marry Allison and never be single again. And Allison felt the same way.

The elevator doors slowly opened to the main hall. The doors to the dining area were open and it looked like a 5-star restaurant inside. Each table had a number on it. The booths had curtains and candlelight. Very intimate, private and upscale. Some tables had 2 people already, but most only had one person there- one very nervous looking person waiting to meet their perfect match. "What number do you have?" Allison whispered.

"44, what's yours?" Tessa whispered back.

"60" Allison replied. They walked through the tables, in reverse sequential order.

"God, everyone is so fucking attractive, but we still might be the hottest people here." Allison giggled.

"I think we might also be the youngest." Tessa scanned the tables for their numbers as they walked. Allison nodded as she considered the ages of everyone they could see and had seen so far.

"You might be right." Allison whispered back. As they approached table 60, they slowed down. The gentleman waiting there looked to be about 30, he was well dressed and attractive. He looked about 6 feet tall, long dark hair and a long-braided beard. He was the definition of tall, dark and handsome. He looked like the guitarist of a rock band. Sexy, confident and tall. He initially stood up to greet both them, his eyes excited and full when he looked at the two of them

"Did I win the lottery?" he asked as he opened his arms to both. Tessa laughed.

"You did when you matched with me." Allison responded quickly. She stepped forward and shook his hand. His hands were so large, and she was so small and fragile next to him. He smiled and laughed with her, as he locked his attention on her. Allison turned to Tessa, gave her a peck on the cheek and unclasped her arm from Tessa's. "Good luck. Call me if you need me." She whispered and then took a seat across from her match in the small leather booth. Tessa continued her walk through the tables. When she reached the 40's, she got nervous, but she kept walking. When she walked by tables with only one person, they got excited to see her and then realized she wasn't there for them and became a little disappointed. She imagined she probably would be doing the same thing.

Table #44. She stared at the embossed gold number on the card on the table for a second longer before she looked to see who was there. There was so much riding on the moment. She hoped for someone attractive and sexy- but also kind. Someone she could get along with, someone who would be protective. She had an extensive wish list and over the past few months, she had built up this moment in her mind. When she saw who was there, all thoughts left her mind. There must be a mistake.

Jake

What the actual fuck? "Tessa?" he asked in a hushed tone. She sat down in the opposite booth and pulled the privacy curtain closed. He matched her and pulled the curtain on his side of the table closed as well. They could still hear other people, and they could hear them, but they couldn't see them.

"Dad?" she asked in an equally hushed tone. "What are you doing here?" Her cheeks were reddened, and she put her face in her hands, as if to cover up the mortification.

"This is the cruise I told you about. What are you doing here?" He started to laugh a little. Of course this would happen to him. He was the most unlucky person to have ever existed.

"This is the trip I was talking about." She answered. "Oh my god..." she groaned and put her head in her hands. "This is so embarrassing!" She said in a screaming whisper. "This is my table!" She held up the token with #44 on it. "They matched us together!"

"It's okay." He said quietly. He instantly went into Dad-mode to try and fix the situation. "Look, its fine." He said, only half believing it. "Tessa, look at me." He reached out to her and touched her arm. He pulled her hands from her face. She slowly raised her gaze to him and tilted her head to the side- kind of like she used to when she was a teenager and he was trying to explain something, but she wasn't hearing it. "It looks like everyone is partnered up, so we can't go breaking couples up so they can re-work the numbering. Let's just have dinner. It's not a big deal." She settled back in his booth and folded his hands in front of him.

"Dad, we matched with each other. It is a huge deal."

"No, its not. I just wanted a vacation. I was hoping to meet someone, but seeing you is great. I hardly ever get to see you anymore. Besides, there are beach days, we're on a beautiful boat, there are plenty of fun things to do in the meantime." He looked at his daughter and for a second, saw her as an adult- and not his child. She wore a dress that exposed more of her body than he had seen before. Even on the beach on family trips, she usually wore a t-shirt over herself. But tonight, she wore a dress, with a lower cut neckline. She was tan, her hair was down, makeup was done lightly. She was very pretty- even though she was on the verge of dying from embarrassment.

"Look, I can be plenty happy by the pool for 5 days. But I ruined your cruise. You should have been matched with someone you would enjoy being with." She crossed her arms and in a pouty gesture pushed herself back against the back of the booth.