Vacation Swap

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Jessica and Jack have an unexpected encounter.
8.3k words
4.3
72.9k
64

Part 1 of the 3 part series

Updated 06/10/2023
Created 06/19/2020
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It was the sixth day of a ten day family vacation with our two kids at our favorite resort in Cancun and we were both pretty revved up, sexually. Vacations do that to you. The stress-free nature of being away from all responsibilities, seeing each other in very little clothing, not to mention the bevy of sexy bodies on display, inevitably leads to heightened arousal. Up until this point, we were enjoying all eye candy from afar and fucking every chance we could get. Thanks to the awesome kids activities the resort provides, we had no issues arranging for alone time and honestly, it's one of the biggest reasons why we love coming here.

Being that it is family-friendly, we usually subdue our kinky side when out of the room, though it has been known to show itself from time to time. And, while finding others to play with is always on our minds, it's not something we actively look for here as we know if we ruffled some feathers, we wouldn't want there to be any awkwardness if we crossed paths later in our stay. Luckily, that would all change on this particular trip.

It was early afternoon, just after lunch, and we were enjoying the pool with our kids. Jessica was relaxing next to me in her black bikini. It showed just enough skin while still being appropriate around our kids, but it didn't stop the various men, young and old from taking in the view. It's always arousing to me to hide behind my sunglasses, seemingly oblivious to all the passers-by trying to sneak a peek, either overtly, or while trying to not get caught by their significant other. I couldn't blame them, though. While Jessica is in her early-forties, she could easily be mistaken for late twenties. Her ample curves are perfectly accentuated by a thin waist, giving her the perfect hourglass figure, not to mention her striking blonde hair, stunning green eyes, and soft tan skin.

The kids were both off splashing and playing around when a Filipino family set up in the lounge chairs next to us. They smiled and said hi as they were setting up, laying out their towels, and slipping out of their cover-ups. I was stealing glances at the wife as much as I could without getting caught while they got settled. I could tell she was about Jessica's height but definitely curvier and without as flat a tummy, with short curly brown hair, pretty brown eyes, and though she was wearing a one piece bathing suit, it perfectly showed off her busty chest and plump ass. The husband was fairly fit, somewhat shorter than I, but since I stand 6'4", most people are, and he definitely caught my wife's attention when he removed his shirt.

The family of four then made their way into the pool, giving me the perfect view of this voluptuous woman's plump ass as it disappeared into the water. My wife and I exchanged looks and smiled, knowing exactly what each other was thinking. After watching the family play in the water a bit, the husband and wife return, him taking one of the lounge chairs closer to us and her staying in the water, propping herself up on the edge of the pool right in front of us as she chatted with her husband. My hidden eyes were glued on this woman's chest, her caramel colored breasts being perfectly pushed together by her arms.

I had to fight the urge to not go rock hard right then and there so I turned to my wife. That certainly didn't help because the first thing that caught my eye was Jessica's fingernail lightly tracing the edge of her bikini top. I smiled at her and quickly turned my attention back to the woman in front of us, only this time it seemed she saw right through my sunglasses as she stared right back at me. My heart nearly jumped out of my chest.

You would think having been in this situation numerous times, obviously minus the kids, I would be calm and collected But, nope! I quickly turn my attention back to Jessica, and nearly knock my drink over. "Real smooth, Jack," Jessica quipped.

I stay silent as I continue watching out of the corner of my eye as the wife mouths something to her husband, followed by her adjusting the top of her bathing suit. My wife nudges my elbow and tells me, "I think that's for you." Just as she finishes, I focus my gaze on the wife's ample cleavage, and the faint hint of dark areola peeking out from the top of her suit. While not normally the one to flat out stare, my eyes were glued on this sultry woman, and I was very glad I did because I was met with a seductive smile and a look in her eyes that told me she was up to something. That's when the husband broke the ice, introducing themselves.

"Hi," he says, "I'm Edwin, and this is Marie." Marie waved while still smiling at me.

"Hello," I reply as I turn towards my wife. "This is Jessica and I'm Jack, nice to meet you guys," I continue as I offer my hand for a shake. Jessica says her 'hellos' as Edwin and I shake.

Edwin starts some small talk, asking where we're all from, how long we've been at the resort, etc and then I get sarcastically confronted about liking the view. My heart sank for a moment but he quickly let on that they knew what they were doing and wanted to gauge our reaction. We all have a chuckle and Edwin tells us that based on both of our reactions, they figured we might be in the lifestyle.

From that point, the discussion was focused on the lifestyle, as much as it can be with kids and other people all around, and it soon became obvious we were all very hot and bothered by our discussion. It didn't take long but we were soon setting up some play time for later that evening, Marie suggesting that our kids might enjoy hanging out in the resort's game room while we joined them back in their room. We all agreed and after another hour of swimming and hanging out with our new friends, we eventually headed back to our room to get ready for dinner.

Back at our room, Jess, I, and the kids take turns in the shower, getting ready for dinner. As usual, I go last, right after Jess, and immediately notice her razor and shaving cream, sending a rush of blood down to my cock. Without fail, my mind is immediately filled with visions of my sexy wife shaving her pussy bare in anticipation of the night's activities. I quickly soap up my body and wash my hair, mixing in some strokes of my growing cock along the way. A few times, I bring myself right to the edge with my soap covered hand, picturing Jessica's slick cunt devouring my cock, only to back off at the last second, wanting to save my load for later.

Dinner is a frustratingly slow affair, although it probably didn't take any longer than normal. Given what lay ahead, Jessica and I stole numerous glances and touches under the table, teasing each other and giggling, and confusing our kids in the process. It didn't help that my wife looked incredibly sexy in her white summer dress and heels. We kept the meal light and when we all finally finished, the kids announced that they were heading to the game room to meet their new friends. We told them to enjoy themselves and to not worry if they came back to an empty room as we might be out dancing.

We finally arrive at our new friend's room, the door opening only a brief second after knocking, and they invite us in. Right away, Edwin is complementing Jessica on her dress and I do the same for Marie. Marie looks stunning in her white and blue summer dress, which is very low cut, perfectly framing her large breasts and showing an ample amount of that cleavage that I've come to desire, while complimenting the rest of her curvy body perfectly. They have the same room as us, two double beds separated by a small table, keeping them about 3 feet apart. Edwin offers us drinks from the fully stocked mini-bar and we all place our orders. There's not much for seating, so Edwin guides us to between the beds, ladies first, sitting opposite each other and the guys next, with Edwin taking the initiative to sit next to Jessica while I take his lead and sit next to Marie.

Not wasting any time, Marie's hand falls to my thigh and she announces she'd like to play a little game to get things started.

I raise my eyebrows at Jessica and she giggles before taking another sip of her drink before I announce that I think we're all up for playing along.

Marie chuckles and squeezes my thigh as she says, "I figured you guys would. So ... I thought we could get started with a little game of 'truth or dare'."

My cock was already starting to stir when her hand fell to my thigh, but hearing her say we're going to play 'truth or dare' nearly brings it to full attention. I look over at Jess and she's started to massage Edwin's inner-thigh, taking a cue from Marie as she eagerly listens to the sexy woman beside me.

Marie announces that I'll go first, and that I get to ask her 'truth or dare'. Then we'll circle around, with Marie asking Jessica, Jessica asking Edwin, and he asking me.

My cock was already awake but now my heart is beating loudly in my ears as I contemplate the possibilities. I guess I must have gone blank because the next thing I know, I hear, "Hun!? Uh, babe, c'mon, you're up!" Looking up at Jessica, I quickly snap to as everyone has a laugh. "Oh, right...I'm up...I'm definitely up!" I exclaim as I adjust myself. Marie lets her hand move from my inner-thigh to my cock, coming to rest right on the tip. "Yep!," she exclaims. "He's definitely up!"

We all have a laugh while I regain my composure. "Okay, ready?" I ask.

"We've been ready, Jack!," Edwin laughingly blurts out, turning my attention towards him and his arm wrapped around my wife's waist.

"Okay, Marie, 'truth' or 'dare'?" I ask.

"Hmmmmm ... I choose 'truth'," she cheerfully responds.

"Okay then ... what is your biggest turn-on?"

"Oh, jumping right into it, are we?" Marie then turns her body towards me and places both her hands on mine. "Well, Jack, since you asked, I'm going to give you the honest truth ... My biggest turn-on is when the person I'm with completely submits to me and is only interested in my pleasure. Almost like you're my personal sexy toy whose sole purpose is to get me off."

It's not lost on me that she said 'the person' and not 'the man' and I can feel my throat tighten as she speaks and the room goes silent for a moment afterwards. And, although I'm usually the dominant one in the bedroom, my cock stirs at the thought of being this sexy woman's sex slave. Jess eventually breaks this silence. "Phew! Is it getting hot in here?", eliciting a laugh from all of us.

"I'd say so," Edwin answers as he looks my wife up and down. "Okay, Marie," he continues, "your turn."

Turning away from me, towards Jessica. "Okay, Jessica, 'truth' or 'dare'?", Marie asks.

"Truth!"

"Wow, no hesitation...I like it. Okay, let's keep the theme going. You heard mine, now what is your biggest turn on?"

"Well ... of course it turns me on when my lover is only interested in getting me off, but what really does it for me is completely submitting to their every desire. Not necessarily the opposite of you, but I love when someone has their way with me."

Marie's eyes light up instantly. 'Mmmmm ... I knew we'd love you before, but now I'm even more sure. Don't you agree, sweetie?" she asks of her husband.

"Mmmmm hmmmm."

Taking the lead, Marie tells Jessica that it's her turn.

Jessica turns to face Edwin and asks, "'truth or dare'."

"I'll take 'truth', as well, Don't want to mess up a good thing, right?" he asks.

"No, we certainly don't," Jess answers. "Okay, Edwin, what is your biggest turn on?"

"Oh, that's easy," he begins. "I love a woman that loves to suck cock!"

We all laugh in unison before he continues. "I know, who doesn't, right? But in all seriousness, I love when a woman is truly into it, like she really loves sucking cock, is confident in that fact, and gives it her all. And of course, the messier the better."

"A'men to that!" I exclaim, eliciting another round of laughter.

"Okay, Edwin, your turn," Marie says.

"Right, okay, Jack, 'truth or dare'?"

"Well, not that I have anything to hide, but I"ll take 'dare'," I say, at the risk of being shamed for not playing along.

Jess lets out a little 'boo' but I can see Marie and Edwin eyeing each other and I can tell they're glad I chose 'dare.'

Edwin seems pleased by this and proceeds. "Okay, Jack, I dare you to kiss my wife."

"I wouldn't really call that a 'dare'!," I exclaim.

Edwin chuckles. "True, but when you see where it leads, you might."

For a split second, I wonder what I've gotten my wife and I into but I figure there's only one way to find out. I turn towards Marie and lean in to kiss her, her soft lips meeting mine, opening in unison as our tongues soon find each other. While my hands start roaming her backside, pulling our bodies together, Marie aggressively kisses me back, sucking hard on my tongue before releasing it and biting my lip.

It takes me by surprise and I pull back only to be greeted by a look of pure lust. Out of the corner of my eye I can see that Jess and Edwin are now doing the same, his hands fondling my wife's ample tits through the thin material of her dress. Just as I see him pull one of the straps of my wife's dress down, exposing her breast and taking her hard nipple into his mouth, Marie turns my attention back to her.

We kiss some more as my hands start to explore her front-side as well, my cock swelling even further at the feeling of this voluptuous woman's huge breasts in my hands. She moans in my mouth as our tongues dance in and out and she occasionally bites my bottom lip. On the last bite, she tugs hard before moving her mouth to my ear. I love when a woman sucks on my earlobe and kisses my neck so I was more than excited when she leaned in. Except, she didn't kiss or lick or suck. Instead, I hear her whisper, "lay on your back, Jack. I want to ride your face until I cum."

"Holy fuck!" I let out, only to see Jessica and Edwin stop their kissing and turn their attention towards us.

"Now!", Marie demands as she motions for me to lay across the bed, pointing to where she wants my head.

"Yes, ma'am."

I lay across the bed as instructed, my head pointed towards an intently watching Jessica and Edwin, as my cock pitched a tent in my shorts. Marie then stands between the beds, facing our spouses. Looking up and back, I see Marie's plump caramel-colored ass come into full view as she lifts her dress and spreads her legs to straddle my face, before letting her dress fall back into place.

It's dark and musky and I can feel the heat emanating from this woman's cunt before she lowers it to my mouth. I savor the taste of her smooth cunt as she starts to rock her hips back and forth, coating my face in her sweet juices.

I can barely hear what's going on, having my ears covered by this sexy woman's thick thighs, but I can tell she's moaning and getting into it, slowly rocking her hips back and forth along my tongue and nose. Her smell and taste is intoxicating and the fact that I'm being used as her sex toy only makes it hotter. My cock strains against my shorts, wanting to escape, wanting its freedom, freedom to be touched. But I hold back from gripping it, not for fear of punishment, but because I want to focus on the woman above me.

Marie continues to grind her hot cunt down onto my face, pressing harder and harder as her pussy glides from my chin to my forehead, momentarily giving my tongue access to her puckered asshole. Sadly, I feel her slow her grinding before pulling off my face and the rush of cool air lets me know my entire face must be covered in her nectar. That's confirmed by Jessica's reaction. "Wow! She really got you good, Jack!"

I lick my lips in response, savoring the sweet taste of this sexy woman. "Mmmmm...yes...she...did." Looking up at Marie, I see her smile at her handiwork before she lifts her dress over her head, revealing her luscious body to all in the room. She then climbs back on top of me, but this time, facing away from our spouses, in a 69 position. Just as she does, she chuckles and says, "seems like someone else enjoyed that just as much as I did," as she presses her finger into the pre-cum soaked wet spot on the front of my shorts.

Another round of laughter from the room before Marie lowers her pussy to my face once more, grinding her fat pussy up and down the length of my face. I do my best to tongue her cunt but I can tell that's not what she's interested in. She's clearly in charge of her own pleasure and that shows by how she fucks my face. At the same time, I'm wishing she'd pull out my cock and suck it while she rides my face, only to be disappointed.

After a few minutes she says she's getting close and commands me to suck on her clit and not to let go. I do as I'm told and suck for all I'm worth as she grinds and wiggles her pussy down on my face, making it difficult to stay latched on to her plump clit. In a matter of seconds, she lets out a loud moan as she squeezes her soft thighs around my head and her pussy begins to spasm, leaking her girl cum all over my face.

Once Marie finishes we're all silent, me not by choice, but the others by astonishment. Marie then rolls off me and sits up before telling Jessica, "Wow, you've quite the obedient man, here."

"I suppose I do," she responded before getting up and disappearing to the bathroom, returning to her and Edwin's bed with a towel. "Now let's see if we can take care of your man," she says to Marie.

Jessica then pulled the other strap of her dress off her shoulder and let it fall to the ground, exposing her perfect C cups, flat tummy, shaved pussy, and deliciously round ass.

Edwin's eyes light up as she does and he starts pulling his shorts and underwear off before Jessica could get her hands on his shirt, helping him slide it over his head. Jessica has him sit on the towel so he's propped up against the headboard.

At the same time, Marie tells me to undress and then guides me to spoon her from behind as we lay on our sides so we can watch the show, my cock nestling perfectly between her plump ass cheeks. I'm slightly perturbed that she isn't going to copy my wife but excited to watch.

As Jessica gets into position between Edwin's legs, Marie reaches between hers, grabbing my cock and pulling it between her thighs, the top of it pressed to her pussy, and squeezes, holding me tightly in place. My free hand instinctively glides up Marie's front side, coming to rest on her plump breast..

The three of us watch intently as Jessica takes the base of his cock in her hand and I can tell she's sizing him up. Even from over here I can tell he's fairly large and Jessica confirms when she looks him in the eye and tells him, "impressive," before lowering her mouth, taking the head of his dick between her lips. She then swirls her tongue around the spongy tip before sliding a couple inches into her mouth. Edwin moans out in response, making Marie squeeze my cock tighter between her thighs.

Jessica then pulls him from her mouth and licks down his shaft, moving her hand under his balls so she can get to them. With her other hand, she grips the head of his cock and strokes as she alternates sucking each of his balls into her mouth.

Watching my wife pleasure Edwin with her mouth makes my cock throb, knowing exactly what he's feeling. I try to hump my cock in and out of Marie's thighs in response, only for her to clamp down harder.

Jessica then licks back up his shaft. Regripping the base of Edwin's cock, Jessica hovers her mouth over it and lets her saliva fall from her mouth, thoroughly coating the head and dripping down the shaft, before taking him back into her mouth.

My wife then goes to work on Edwin's cock, bobbing her head up and down while stroking his shaft in unison, saliva and precum leaking from her mouth and running down his shaft and over his balls.

Apparently, my cock liked what my eyes were seeing because it started oozing precum of its own all over Marie's thigh. And, it didn't go unnoticed.