The Vacation

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Jeremy takes a vacation and meets Stephanie.
7.3k words
4.69
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Part 1 of the 5 part series

Updated 08/11/2023
Created 07/30/2023
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This story is a bit different in that is actually a story and sex is a part of it. It's in 5 chapters. Chapter 1, 2 and 5 have a lot of exposition while 3, and 4 have faster action. This is really a short romance story but it's helping me grow into longer narratives.

*

Jeremy woke up a little groggy and looked at his alarm -- 6:00 AM, on a Sunday of all things. I knew I would be happy about it later but right now I just wanted to go back to bed. Stacy, my 13-year-old daughter came bounding through the double doors into the room and yelled "Dad, time to get up for the vacation!"

I smiled and said "Okay, get dressed and be downstairs in 30 minutes." I was really looking forward to a week in Hawaii on the big island. I knew she was all packed as we had taken care of that last night and went to shave and take a quick shower.

Looking in the mirror I saw a 37-year-old divorced father of one who was 6'3" tall, still athletic looking, and as my daughter frequently told me "reasonably good-looking." I smiled at the thought and started to get ready. 30 minutes later dressed and downstairs, Stacy and I were ready to leave.

The ride to the airport was about 45 minutes and we arrived two hours prior to their departure (I'm a punctuality fanatic and always aspire to the notion that being right on time is the same as being late -- 5 minutes early is my motto). Seattle-Tacoma International Airport, commonly referred to as SeaTac was a disaster as usual. The security lines took forever but fortunately we had checked in early online so that was the only disaster we had to deal with.

Checking our bags was quick and easy and after a 30-minute wait in the security line we were at the gate waiting for the plane to take off. We were flying Hawaiian Air and the departure area, in contrast to the rest of SeaTac was immaculate -- a nice change to some of the more run-down gates.

"Stacy, I'm going to grab some coffee at Starbucks, do you want anything?"

"Yes dad, can I get a Strawberry Smoothie and a toasted bagel with cream cheese please?"

"Yup. Be back in a few minutes."

It seemed like no one in Seattle could survive without a morning cup of Starbucks and the line was particularly long. Pretty much everyone looked like I did -- just waking up, bored and happy to be through the security line. Just another day at the airport. I ordered my coffee and Stacy's food and headed back to the gate.

I saw our carry on but didn't see Stacy anywhere. Looking around more closely I saw the back of her head. She was talking with two girls who appeared to be about the same age as her and who looked like they were sisters. This was starting off as a good trip -- maybe she would make some friends that she could hang out with during the vacation and then have them when we came back. This was the best that I could hope for. That would give me some free time to relax, play golf, go swimming and just unwind.

The resort we were going to was mostly a family type of resort. My research consisted of looking for family resorts on the big island and picking the one with the best rating. After all, this was the big island and there were a bunch of things to do. We ended up picking the Hilton Waikoloa Village which was on the west coast of the island. We decided to fly into Kona since it was the closest airport (Hilo is on the other side of the island -- not a huge drive but I was thinking that wasn't such a great option after flying for five and a half hours). It's just a quick 30-minute drive from Kona International to the hotel.

Boarding time finally rolled around and I called Stacy back over. She came running over and said, "Dad, dad, guess what, I met two girls who are starting Redmond High next year when I start, we're going to be in the same grade together!"

"That's great honey. Where are they staying in Hawaii?"

"That's the best part dad, they're staying at the same hotel we're staying at! Their names are Tracy and Rebecca. Rebecca's older than Tracy be almost a year but they're both 13 also!"

She was obviously super excited about his revelation and I was thrilled -- she had made new friends before we even left and she would have two girls to play with. I just hoped they came from a nice family but I could worry about that later. That's the problem with being a single parent, your whole world consists of making sure your child or children are safe because you don't have time for anything else. This vacation was my time for something else but you can't ever get away from being a parent.

We were sitting in row 10 in the aisle and middle seat (being tall, I almost always have to sit in the aisle seat lest my legs get too cramped). The girls Stacy had met were sitting in row 24 and I heard her tell them she would see them on the plane. When we sat down, I asked Stacy if she had met their parents and she said that they didn't have a father (she didn't elaborate) and they were traveling with their mother but she didn't meet her.

The plane took off right on time and as soon as we hit 10,000 feet Stacy said, "Dad, can I go back and talk with Tracy and Rebecca?"

"Sure honey, just be careful of any carts coming down the aisle and be respectful of their mom."

"Yes dad." And away she went.

I closed my eyes to try to get a little bit more sleep. Less than 10 minutes later I could feel someone looking down at me and I cracked an eye. Standing in the aisle next to me was a woman I could only describe as stunning (at least to me since I believe beauty is always in the eye of the beholder). She was approximately 5'9" tall with what looked like an hourglass figure (hard to tell since she was wearing a loose fitting top and a lighter weight white skirt that went down to her knees). She was wearing stylish black glasses that looked like reading glasses and gave her a sexy librarian look. Glasses always did it for me -- I think they make a woman look amazing. She had brunette hair that was wavy and shoulder length. Her eyes were a deep blue that looked the color of the ocean and that's pretty much where I stopped -- she was captivating.

"Excuse me, are you Jeremy?"

"Yes, do I know you?"

"No, no you don't. I'm Tracy and Rebecca's mom."

"Oh, the girls my daughter just met."

"Yes, all three of them begged me to switch seats with Stacy so they could talk. I figured that it might give me a bit of peace and quiet on the flight and I thought it would be weird for your daughter to stand in the aisle the whole flight."

"Please, please take a seat." I got up out of my seat and brushed past her to make room. There was something about her that just fired up my imagination and I felt my pulse increase. What were the odds of meeting a single mother on the way to a vacation staying at the same hotel I was staying at with daughters who were the same age as my daughter? It had to be a million to one but I would take it any day of the week.

"Well, you have a leg up on me as it were -- you know my name, only fair if I know yours" I said lightly with a smile.

She grinned at me and said, "It's nice to meet you Jeremy, my name's Stephanie."

"Hi Stephanie, it's nice to meet you also. Not that this is a bar or anything, but what's a pretty girl like you doing in a place like this?" I knew it was corny when I said it but I've been out of practice making casual conversation with the opposite sex and I wanted to start off on a light foot. I may have gone a bit too far to the dorky side though.

"That's a fair question. I take this flight every week in search of men to pick up." I must have looked like I was dumbfounded because she laughed lightly and gave me a big smile. Her laughter was like music and I was hooked. She had a great sense of humor, was quick on her feet and gave as well as she got. Her laugh was infectious and I started chuckling.

"Seriously though, my daughter said something about Tracy and Rebecca not having a father. I don't mean to pry but the way my daughter put it made it sound strange and I was just curious. Please don't feel as though you have to answer as I know I'm a complete stranger."

She looked at me and furrowed her brow a bit and I could see the gears turning. It was almost like a "I just met him, how much should I open up to him" type of moment.

"My late husband was killed in a car crash six years ago."

"Oh, I'm so terribly sorry. I really didn't mean to pry."

"It's okay, you didn't know, and I know you were just trying to make conversation. It doesn't hurt as much as it used to, but I try not to think about it anymore. It was -- and still can be -- painful, but I figured I have to live my life, or it isn't going to be much of a life. Besides, I have my two beautiful daughters and they're my life now."

"Well, for what it's worth, I am sorry. Sometimes my curiosity really causes me to put my foot in my mouth."

"That's okay. Let's try it with the shoe on the other foot. Stacy said she didn't have a mom anymore either. What's your story if you don't mind me prying?"

"It's okay. One good turn deserves another. I got divorced, about four years ago. My wife was apparently having an affair with someone who was much richer than I was and that was apparently more important to her than anything as silly as love. Fortunately, she filed for divorce and the judge hit her with alimony. She didn't even want custody of Stacy which is the thing that hurt the most I think."

"Still single though?"

That was an interesting, if not loaded question I thought. The way she asked it, it was almost a prelude to something else.

"Yup. Being a single parent, as you know, takes up all of your time. No woman wants to go out on a date and then find out that you have a teenage girl. For some reason that's a lot of baggage for women, maybe because they don't want to have to try and bond with the daughter while they still aren't sure if they want to be with the father. So, I haven't gone out on many dates in the last few years. It's always rushing off to softball practice or volleyball or some social event. I find it consumes all of my time. The benefit is that I have a good honest relationship with my daughter, we have lots of long discussions about everything from boys to politics. Not that I'm keen on the boy's discussion but it's going to happen eventually, might as well make sure she's prepared. It never seemed worth my while to spend time with women who weren't ready to commit to Stacy and her life like I do -- the idea of a one-night stand just wasn't any part of an agenda that I wanted."

I paused for a second and realized I just went somewhere I shouldn't have.

"I'm sorry, that was probably a bit more than you wanted to hear. I'm a little out of practice with having a normal conversation with a woman. I tend to be a bit more honest and upfront than I should be."

"It's okay Jeremy, I understand." She put her hand on my arm in understanding.

"Soooo, what are you doing in Hawaii? Just a chance to get away?"

It was a lame way of changing the direction of the conversation, but I was getting a bit uncomfortable with where this was going. Mostly because I think I had the hots for Stephanie and I didn't want it to be that obvious at this point, after all we had only met around ten minutes ago.

"Well, remember when I said I needed to live my life?"

I nodded.

"I haven't actually been doing that. Like you, my girls have been everything to me and I haven't really had a moment to rest. In fact, I haven't been on a vacation in years. I finally put my foot down and decided to take some time off so here we are. I figured a family style resort would be a good place to get away and have an uncomplicated week to myself and let the girls do whatever it is they want to do."

Just then the stewardess came down the aisle with the cart which gave me a nice break because I didn't know what to say. My first thought was that I really wanted to complicate her vacation, but my second thought was that I was a gentleman and I wanted to respect her space.

Stephanie ordered a red wine as did I. For whatever reason I also said to the stewardess, "there are three girls in row 24, please let them order whatever they want, and I'll pay for it."

The stewardess said "okay" and continued with the beverage service.

"That's very kind of you, you don't even know me."

"Well, since there are three girls the same age, I had no way to disambiguate Stacy from Tracy and Rebecca -- I figured it would just be easier to take care of everything. After all, how much can three girls eat?"

She smiled at me and said, "You might be sorry you did that but I still appreciate it."

I laughed and said, "honestly though, I did have an ulterior motive."

"What's that?" I hesitated a little bit and she said, "Come on, you brought it up."

"You're right. I don't know you, but if it isn't too forward of me, I would like to get to know you. I, you, well, you just seem like a really well put together woman and I'm enjoying our conversation. Wait, that didn't come out right -- I didn't mean well put together, I meant, I mean... I'm really screwing this up, aren't I?"

"Jeremy, it's okay. I completely understand."

"You do? Because right now I must either sound like some sort of imbecile or a pick-up-artist."

"To start off with, no pick-up-artist would ever have taken the approach you just did. I think you're a really sweet guy who's really, really out of practice with women. But I won't hold that against you."

"You won't?"

"Tell you what, since we're staying at the same hotel and you're renting a car, how about you give us a lift to the hotel, and we'll go from there?"

"How did you know that I was renting a car?"

"You aren't the only person who was curious and asked questions. Of course, I asked Stacy questions when she was talking with my daughters."

"You're on."

For the rest of the flight, we bantered back and forth and I learned a whole lot about Stephanie and I revealed a lot to her as well. It was maybe the first conversation I had with a woman since Meredith left us. While it was a five-and-a-half-hour flight, it seemed like it went way faster than it really did.

As we got ready to land, Stephanie took my hand and said, "It was a real pleasure meeting you Jeremy. We'll meet you at baggage claim, okay?"

"Absolutely, we'll be there waiting."

Stacy returned to her seat and asked, "How was Stephanie? Did you two talk a lot? Or were you your usual self and quiet and embarrassed the whole time?"

"What?"

"Come on dad. You know how you get when you meet a woman -- any woman -- much less one as pretty as Stephanie."

"What is this, some sort of setup?"

"No, it's me taking advantage of an opportunity for you that you didn't know about."

"I'll have you know that I can take care of myself young lady."

"No you can't. You can take care of me just great; I mean really, you are a great dad. You don't do anything for yourself. You're the most selfless dad I know, and I love that about you. This week is time for you to enjoy yourself as well, not just make sure I enjoy myself. Silly. Go with it."

"Okay smarty-pants. I'll just have you know that we're driving Stephanie, Tracy and Rebecca to the hotel. Apparently, you mentioned where we were staying and that we're renting a car."

"I did? Well, I'm sure I didn't mean to. Way to go dad." She gave me a peck on the cheek and grinned like a Cheshire cat all the way to the terminal. Sometimes my daughter was way too clever for her own good. On the other hand, I couldn't get mad at her as this was starting off to be a very good vacation.

Once we exited the plane, we made our way to baggage claim and waited for the bags to come down. Stacy and I are light packers, even for a week in Hawaii. We had one large bag that had Stacy's stuff and the carry on which was full of my clothes. Stephanie and the girls showed up a few minutes later and Stephanie went to get their suitcases. She came back with the first one which was huge, and I said, "Is that it?"

"For three women? Are you kidding? This is my bag. Tracy and Rebecca each have larger bags."

Oh boy I thought to myself -- we aren't going to be able to fit all of the luggage in even a full-size car. Guess I have to upgrade to an SUV I thought. "Okay, let me come with you. You point out the bags and I'll grab them."

We waited for the girls' bags to come around and Stephanie wasn't kidding -- these suitcases were big and heavy.

"What could two girls pack that was this heavy?"

"You have no idea how much makeup weighs do you? Not to mention two sets of clothes for each day of the trip."

I started wondering what I was getting myself into. But one smile from Stephanie got that out of my head really quickly. I just didn't care at that moment. "Alright everyone, off to the rental car. We got a car from Alamo, so we have to take a shuttle."

After we got to Alamo, I tipped the driver ten bucks and went inside while the women waited with the luggage. I upgraded to a Ford Explorer, grabbed the keys and headed outside.

"If you will follow me, the car is right this way."

Everyone piled into the car, and I loaded the luggage. The hotel was north of the airport by about 20 miles on the Queen Kaahumanu Highway. It was an easy, picturesque drive and for most of it we could see the ocean off to our left.

"Did you girls enjoy the flight?"

"Yes, we talked the whole way here. Did you know we're going to the same school as Stacy this year? It's going to be so much fun. We just moved from Arizona a few months ago and since we haven't been in school it's been hard to make friends and Stacy has been super friendly."

"She is friendly to a fault. And she did mention you would be in the same school. I'm sure she'll be happy to introduce you to, well, Stacy seems to know everybody, so she'll introduce to you everybody."

"Dad, it's a new school for me too and there are going to be other kids there from other middle schools, so I won't know everybody. Geez."

I looked at Stephanie and whispered, "It'll take a day or two, then she'll know everybody."

Stephanie laughed and again it was music to my ears.

"What are you three doing for dinner tonight?"

"I don't know. We've never been here before, and I haven't spent a bunch of time on research. I figured we would just eat at the hotel."

"Actually, um, mom?"

"Yes Rebecca?"

"Since it's only 1:30, we, all three of us, were hoping we could go to the beach and then we saw online that there was a mixer for teenagers tonight at 5:30. Is it okay if we all go to that together?"

Stephanie looked at me. Stacy looked at me. Rebecca and Tracy looked at me.

"It's okay with me as long as it's okay with Stacy's dad. When does the mixer end?"

"It ends at 10:00 and it's on the beach with a whole bunch of other people so we'll be safe and we won't go off with anyone since we don't know anyone."

"Jeremy?"

"I'm okay with that as long as the three of you stick together."

This was unexpected but then I could spend more time with Stephanie. "How about you? Care to have dinner with me? I did a little bit of research, there's a nice restaurant at the resort that overlooks the beach."

"Absolutely. What time should we meet there?"

"How about 5:30? Sunset is at 6." I said with a smile.

"Okay then, it's a dinner date." I swear I saw all three girls smile in the rear-view mirror and wondered what kind of conspiracy was going on.

We arrived at the hotel a few minutes later and checked in. Stephanie was in the same tower we were, but five floors higher meaning they had a way better view of the ocean than we did. Stacy and I were in a single room with two King size beds. We headed up and Stacy said to Rebecca and Tracy, "I'll meet you down here in 30 minutes?"

"Make it 15!" and they ran off with Stephanie.

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