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Swinger Vacation Ch. 01

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Father & Daughter's all inclusive vacation with benefits!
12k words
4.55
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Part 1 of the 3 part series

Updated 06/09/2023
Created 09/01/2019
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Written by myself, edited and re-edited by Oldnakeddad.

***Day One - Part One***

I don't know about you other dads out there, but I'm a sucker when it comes to my daughter (Sofia). She has me wrapped around her little finger.

I'm a successful man and have my own business with numerous staff. I hire, fire, and make important decisions on a daily basis, yet, I'm such a soft touch when it comes to my baby girl. She knows exactly how to play me to get what she wants, especially when it comes to spending my money!

Take the other day for instance. She called to tell me she'd split up from her latest boyfriend—Andy, Adam, Anthony, or something like that. I've lost count and stopped trying to remember their names.

"Daddy, I'm traumatized and need a vacation to get over it."

I thought she wanted to take a little trip to Greece or Spain with her friends, but oh no!

"I've found a great place in the Caribbean, Daddy, and I know you'll love it."

"What do you mean, 'I'll' love it?"

"It fits all of the items on your vacation criteria list, Daddy. Seriously, you're going to love it! Not only that, you need a vacation because you work way too hard. It's time for a break."

She could be very persuasive, and she always found a way to make any spending situation into one that'd benefit me. It was true, I hadn't had a vacation in two years, I did work too hard, and I really could've done with some R & R and sunshine on my bones.

I tried not to sound too enthusiastic.

"So, tell me more about the hotel you've found, and how much this trip is going to cost me."

There was so much excitement in her voice, I could tell she'd already made up her mind about the trip and there was no way we weren't going to go.

"Ok, Daddy! It's all inclusive, it's adult only, and it has a private beach. There's a swim up pool, three different restaurants, and a fantastic gym so you can train every day if you want to."

The gym was a must for me because I enjoy my training. It's an important thing in my life. I like to train every day because keeping fit helps me de-stress, helps me focus my mind, and keeps me in shape.

I liked the idea of it being all-inclusive, too. It meant I won't have to think about how much anything is going to cost—we'll just eat and drink as much as we like. The adult only thing was something I liked, too. I have no problem with kids, but I don't want to hear or see them when I'm trying to relax during a vacation.

"Ok, Baby, it sounds perfect. Book it and email all of the details to me."

She had a credit card that I'd given her for such occasions. The two-week trip was only five thousand dollars, including the flights, transfers, hotel, and all we could eat and drink. I thought it seemed to be a good value, considering.

We're very close, and we talk every day, but I never get to see her much these days as she's always so busy with her job or boyfriends. So, it was easy to say yes to two weeks away with her.

Katie is my Personal Assistant.

"Katie, book me out for two weeks, and would you mind coming with me to pick out some new clothes for the vacation?"

***

I know what you're thinking, 'Why don't you do it yourself or go with your wife?' Well, my wife left me eight years ago for another man...my best man, in fact! Not only that, but my taste in clothes is really bad, so I need help.

Besides, my PA is very cute, very sexy, and I enjoy spending time with her. She's only twenty-eight years old, way too young for me, but that doesn't stop me from wanting her. She probably has no interest in me at all, but I'm happy to have any excuse to get her out of the office and be alone with her.

******

Two weeks have passed, my new wardrobe is neatly packed into my suitcase, and I'm waiting at the Miami airport for Sofia to turn up...she's never on time. (Her mother was the same way...always late. She said "it's fashionable", but I found it to be rude). I'm starting to get annoyed, but as soon as I see Sofia and that massive smile on her face, I can't help but forget all of my annoyance.

Typical for her, Sofia has a trolley that has three suitcases on it, but she isn't pushing it herself. There's a good looking guy pushing it for her as she's walking beside him. I'm slightly confused, 'Is this her new boyfriend? Is he coming with us? What's going on?'

As they get closer to me, Sofia starts running toward me with her arms outstretched and ready to receive my embrace. I don't quite know how she manages to run in the heels she's wearing, and neither can I understand how her tits are staying in the strappy dress she's wearing as she's clearly not wearing a bra. She's practically jumping into my arms, and nearly knocking me off of my feet.

I love her enthusiasm for life and, as I hold her in my arms, I feel so happy to be reunited with her. As I lower her back down to the floor, I realize everyone is looking at us. Well, they're looking at Sofia. Her mini dress must've ridden up high enough to expose her ass.

She's not shy when it comes to showing off some flesh, and today's outfit is no exception. The dress is a skin-tight, floral number that barely covers her ass and is showing off her beautiful, long, tanned legs. The top part of her dress is exposing a great deal of her cleavage, and it has two thin straps that look as though they could break at any time and allow her tits to spill out.

"Hi, Daddy! I'm so excited. I can't wait to get going."

She's turning around to face the young man. I'm thinking, 'She's going to introduce me to him', but she doesn't.

"Thanks, Chuck."

The young man is embarrassed by the fact that she didn't remember his name.

"Eh, it's Chad. My name's Chad."

Sofia's voice is dismissive since he'd served his purpose.

"Yeah, well thanks for your help, Chad. I can take it from here."

He isn't getting the hint. He's still awkwardly standing here as if he's expecting a tip.

Sofia is clearly annoyed that he's still here.

"What?"

Chad is awkwardly looking at me, then back at Sofia.

"I thought you were going to give me your number?"

By this time, Sofia has clearly had enough.

"Oh, yeah! I'll tell you what, why don't you give me yours."

She's taking a pen and a note pad from her handbag.

"Write it on there, and I'll call you when I get back."

Poor Chad. Sofia does this all of the time. She has no intention of ever calling him. She only needed him to carry her bags for her. It turns out that isn't all! The poor guy had actually given her a ride to the airport, and he'd carried her bags, under the pretense that he was going to get a date. She's so much like her mother.

***

Sofia is incredibly beautiful. She's twenty-five years old; five feet, seven inches tall; weighs one hundred ten pounds; has the body of a goddess; and has long, thick, black hair. She's every man's "girl next door" dream girl. She has the face of a model and has been approached (many times) to join model agencies or do promotional work, but she wants to be an interior designer and takes it very seriously.

***

Having said that, she knows exactly how to put her good looks to use and always gets what she wants. So poor Chad is only the latest in a long line of poor guys that have fallen for her charms.

Chad is walking away.

"Sofia, I thought you were bringing him with you?"

Sofia is hooking her arm into mine as I add my suitcase to the trolley and start to push it toward the check-in desk.

"No, Daddy, this trip is only for you and me. We're going to have a nice, chilled time while getting some sun and catching up. I'm all yours, I promise.

There was a hint of flirtation in that last sentence, which slightly confuses me, and I'm wondering 'Is she after something? Does she need more money?' I don't care because whatever it is will come out during the next two weeks. I'm just happy to have my baby girl all to myself, so I brush it aside.

As we check-in for the flight, the girl behind the desk is repeatedly calling us Mr. and Mrs. Jacobs. I've started to correct her a couple of times, but Sofia spoke over me. It isn't until we're sitting on our seats, and the flight attendant also addresses us as Mr. and Mrs., when I finally find out why.

"Daddy, I got us a good deal by pretending to be honeymooners."

This makes me laugh because she loves a bargain as much as I do...she got that from me! She's saved me quite a lot of money, so I can't be annoyed.

I feel slightly uneasy, though, as there's twenty years between us—I probably look like a dirty old man—but Sofia puts my mind at ease.

"You look so much younger than your age, and I look a lot older, so it's not a problem. We also have the same surname on our passports, so it's an easy ruse to pull off."

***

The flight has only taken about three hours, which is a shame as we're sitting in First Class. I would've liked to have gotten more of my money's worth, but it went very smoothly.

After we land, it doesn't take long before we're standing at the reception desk to check-in.

"Welcome to Paradise Mr. and Mrs. Jacobs. Here are your keys. Michael will take you to your room."

The receptionist has a twinkle in her eye as if she knows something we don't.

"Enjoy your honeymoon!"

I'm guessing she's thinking we probably won't leave the room for two weeks because we'll be fucking every minute of the day during our honeymoon.

Michael is driving us, by golf buggy, to our room. It turns out all of the rooms are suites. They either have direct access to the free pool, or they're on the floors above and have a balcony looking down onto the pool. We have one with direct pool access, which means we can practically swim our way around the resort.

We're being given a tour en-route to our room, past the restaurants and bars, with a little detour past the health club, tennis courts, and the private beach. It's idyllic. It's the perfect place to spend a honeymoon, and I'm sure there are a lot of couples here on theirs, but I'm with "my daughter." This isn't going to be easy. We need a plan, and we need to chat!

The room is spectacular and has a huge bed as the centerpiece. Everything is open plan, even the bathroom, which has a large window between it and the bedroom. It means we can be in the bath or shower and look into the room (or vice versa) and the pool beyond. Not only that, but when the curtains are fully open, people can see into our bathroom from the pool and gardens, too. The shower door is clear glass, too, so there isn't a lot of privacy except the toilet area, which is separate from the rest of the bathroom.

There's a dressing area next to the toilet area, and a lounge area just before you step onto the terrace. The terrace has a table and two chairs, two sun-beds, and steps that lead into the pool. This is lovely, but there's one problem—we only have one bed, and the sofas are way too small to sleep on.

I'm tipping the bell boy, who's sweating profusely after carrying all of Sofia's suitcases to the room, before I sit Sofia down.

"This is gorgeous, Baby, and I love it. But there's only one bed!"

Sofia is laughing.

"The bed is massive, Daddy. We could put some pillows down the middle or, if you're really freaked out by sharing a bed with me, I can sleep on the sofa!"

I can't have her sleep on the sofa, it's not the gentlemanly thing to do.

"That's not right, Baby. If anyone is going to sleep on the sofa, it'll be me. Unfortunately, they're so small, I'm not sure I'll fit?"

I'm protesting.

"No, I'm not freaked out by sharing a bed with you. You used to do it all of the time. It's just that you're all grown up now, but I'm sure it'll be fine."

She looks happier.

"That's sorted then. Please don't worry, it'll be fine. We're both adults!"

She changes the subject.

"What do you think of the resort? It's even better than the pictures, right?"

She's right. The pictures don't do it justice.

"I love it, Baby. It's beautiful. Did you know it's for couples only when you booked it? We're not a couple. What are we going to tell everyone?"

Sofia is giving me her cheeky smile.

"Don't worry about it, Daddy. Just play it by ear...we can wing it. We're both good at that. Just tell everyone we're on our honeymoon."

I'm still not convinced.

"It's all very well telling people, but couples behave differently than fathers and daughters. It's going to be strange, and you can't call me Daddy because they'll soon realize we're not married and think we're weirdos."

Sofia is finding this hilarious.

"Ok, Daddy, I'll try not to. So, what should I call you? I've never called you by your name, it'll be weird. I could call you Honey, or Sugar, or something like that?"

She's right. It will be weird to hear her call me anything other than daddy.

"Just try to call me Jack. I know it'll feel weird for you, but I don't like silly lover's names. It's going to be easier for me because I can still call you Baby, as I always have."

As Sofia wants to move on, she over emphasizes my name.

"I'm sure it'll be fine...JACK! I'll get used to it. Shall we go for a dip...JACK?"

I'm desperate to get out of my clothes and have a dip, so I'm very happy with Sofia's suggestion.

"That sounds like a great idea. Why don't we swim around to the swim up bar by the beach and grab some cocktails?"

As we're looking around, we realize it's not going to be easy to have any privacy in our room. Apart from the toilet area, there isn't anywhere you can get dressed, or undressed, without seeing each other.

"Sofia, why don't you get changed in the toilet area first, then I'll go in afterward?"

It seems like a good solution to me.

"Thank you, Daddy, but I'll need a little time to find my bikini, and I'll also need to adjust my hair, so it's better that you go first."

I'm putting on a pair of my new shorts because Katie said I look good in them, and they're all the new rage now. They're a lot shorter than the fashion a few years ago. I prefer the board shorts because these look more like little running shorts, but as I'm looking at myself the mirror, I like how they look. I've been training (hard) of late, and my body looks ripped. I'm thinking, 'Not bad for a forty-five year old.'

As I'm walking out, Sofia is blowing me a wolf whistle and over emphasizes my name again.

"Wow, Daddy! I mean, JACK! You look really fit in those. The girls are going to love you. Who knows, you might find yourself a new girlfriend?"

I don't want to point out the obvious (we're in a couple's only resort!) because Sofia seems really happy about the idea of me finding a new girlfriend. So, I'll just play it down.

"Of course, Baby, but I'm here to spend some time with you!"

Sofia is kissing me on the cheek.

"I know, Daddy. I'm just saying, I don't mind if you want to chat with other women."

And off she goes to the toilet area.

As she finally emerges from the toilet area, my tongue is nearly hitting the floor. She's wearing the tiniest string-bikini I've ever seen! It's bright-yellow and consists of two, tiny triangles that "barely" cover her nipples, and another triangle that "barely" covers her pussy.

It's so small, I'm wondering, 'Is she completely shaved?' Almost all of my girlfriends had a Brazilian with hair above their slits, but I don't think Sofia has one like that because it'd be showing above the hem of her bikini, that's for sure!

The shock on my face must say it all because Sofia defends her outfit without me saying a word.

"Daddy, it's a Wicked Weasel bikini. It's what everyone wears down in the Caribbean these days. I read up on it. It allows you to get an all over tan!"

It's hard to look her in the eyes.

"Isn't it a little revealing, Baby? I mean, we don't want to give anyone a heart attack on our first day here. I just think it might be better to start off with something a little more...conservative?"

Sofia looks offended and she puts on her sulky face.

"Daddy, I don't have anything more conservative. They're all like this, so you better get used to it!"

Well, she told me! Sofia has always been hot-headed. There's no way you'll ever win an argument with her, so it's always better to back down and let her have her own way. Today is no exception. We're on vacation and I want us to have a great time. There's no point arguing over a bikini, no matter how tiny it is!

Sofia is turning and walking toward the terrace door. This is when I see her bikini from behind. The string is so small, it looks as if she's naked. I'm just about to say something, but think better of it.

She looks incredible, though. She's obviously been working out, too. Her body is in perfect shape. I can't help but notice her ass, as firm as it is, still gives a beautiful wiggle as she walks. It's swaying in time with her long, black ponytail that comes down to almost meet it.

She has a beautiful skin colour and looks as though she's been tanning before we got here—that's the beauty of living in Florida—yet, I can't see any tan lines? It probably isn't the time to ask her about it, so I'll save it for later. Or maybe not because if I do, she'll know I've been checking out her ass.

After closing the door on the terrace, we're walking down the steps and into the pool. We're partly swimming and partly walking around to the bar at the front of the beach. Even though it's nearly six o'clock, the sun is still beating down.

By the time we get to the bar, I really need a drink. By chance, a couple is getting up to leave as we're approaching, which leaves two stools available for us. As we start walking toward the bar in the shallow water, I notice Sofia's bikini has gone completely transparent.

I'm grabbing Sofia by the arm and trying not to make too much of a scene, or speak too loudly.

"Baby, your bikini! It's gone completely see-through!"

Sofia doesn't even flinch.

"I wondered if that might happen. Oh well, it's nothing they haven't seen before. Besides, that lady at the bar is topless, so I think it's allowed here."

I'm turning around to see the lady she's talking about. She's sitting with her back to us, but you can see she's topless. Her ass is almost completely exposed, too, as she's wearing a thong like Sofia's. She's obviously been here for a while because she has a fantastic tan.

She's slim with long, blonde hair in a ponytail. Although I can't see her face, I just know she's going to be attractive. I'm not disappointed when she turns toward us and, with a Texas drawl, offers us the seats next to her for us to sit down.

"Why don't you guys sit up here and have a drink with us?"

She isn't only attractive, she's actually very pretty. She's friendly, too. Her husband stands up as we approach the bar stools and introduces himself and her as Pete and Lacy.

***

Pete is maybe six feet-one or six feet-two inches tall, well-built, and has a good body. He looks ex-military with a short buzz cut. I'll say he's probably in his fifties, definitely a lot older than Lacy.

I'll guess Lacy is probably thirty to thirty-five years old—it's difficult to tell. She's perfectly groomed, with a full face of makeup, even in the sun. She clearly cares a great deal about her appearance, that's for sure.

***

We introduce ourselves and sit down next to them. Sofia is sitting next to Lacy, which means Pete and I are sandwiching the girls. I notice Pete is having a good look at Sofia's tits. They do look amazing! She has such a slim waist, so her 34C tits look much bigger than their actual size.

He's also having a good look at her legs, or maybe her pussy, I'm not sure. I'm starting to wonder, 'Is the bottom of her bikini as see-through as the top? If so, he's in the perfect position to see, as Sofia is facing him.' I want to look myself, but I don't want to draw attention to it, just in case.



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