Flirty Holiday Resort Vacation

Flirty Holiday Resort Vacation

Hello Everyone! It's Shea here with you. I posted a story just over a month ago called "Flirty Holiday Hot Tub Party" and this is the sequel. I was very surprised from all the positive feedback. I didn't think that I would ever post a follow up. However, with all the enthusiasm from all the readers and along with the support of my wife, here's the true follow up to our first adventure. If you haven't read "Flirty Holiday Hot Tub Party", I suggest you do, just to get acquainted with myself, my wife and our friends that joined us in this escapade. This story is certified fresh, as it happened just 3 weeks ago!

The Flight

"So, go with the flow?" Lynn asked me.

"Ya. We'll go with the flow." I answered with vague confidence.

"We'll go with the flow." Lynn echoed.

"Yes. We will go, with, the flow." I finalized.

It was last Christmas break, when my wife, Lynn, and I had a face melting sex-capade at a Flirty Holiday Hot Tub Party with our friends Vee, Gavin, Meadow and Davis. It was by far the most adventurous, outrageous, erogenous and scandalous night we ever could have even dreamed. Fast forward 10 months and we're packed up and pumped up to be on a plane for the first time in years to finally blow off some steam at an all-inclusive resort for a quick four-night fun-in-the-sun getaway.

It was Vee who started it all, in more ways than one. My wife and I agree that Vee instigated the impromptu hot tub orgy last December, but it was also Vee who extended the resort invite to Lynn and myself. Now here we are, deciding to "go with the flow" as the half-full 737 touches down on the tarmac of our tropical getaway.

Lynn and I have talked at length about that sizzling, alcohol-fueled, boundary-breaking night in the hot tub, but we still haven't really been able to completely process all that went down. For all our apprehensions, shyness and awkwardness that we felt the next morning, the next week, and the next 10 months, we both felt it was all worth it. Our sex has never been better, our confidence has never been higher, and our outlook?

"Go with the flow" we said in unison staring into each other's eyes as cheeky smiles crept across our faces.

It wasn't that we were completely nervous going to the quaint Caribbean Resort with Vee and Gavin, but we weren't completely chill either. The last time I saw Vee and Lynn together, they were naked, soaking wet, in the middle of a hot tub, taking my hot load all over themselves. Sure, we said our good-byes the next morning, created a text chain to help organize the trip, but we really hadn't done a "couples date night" with Gavin and Vee to address the once in a lifetime, sultry December soft swap.

But maybe it wasn't a once in a lifetime scene. Lynn and I gave each other a long passionate kiss as the plane came to a stop and every passenger stood up way too early to exit. We were truly ready to see if our "go with the flow" attitude would result in a lightning strikes twice moment.

The Arrival

True advice to anyone who travels, get an early flight, try to sleep on the plane or get a Red Bull on arrival, but making the sacrifice of an early departure is worth taking full advantage of a full first day of your vacation. That's a free one from Shea!

Lynn and I crashed into our cute 2

nd

floor room overlooking the surf of the Caribbean and we were quick to heave our suitcases into the corner and get out of our jeans and transform into tropical beach people as soon as possible.

Lynn and I have been together for nearly eight years all in all, and once we got the invitation from Vee, we decided to challenge ourselves to see who could get the best beach body. Nothing but pride and a pair of duty-free liquor bottles was on the line. The competition would be won by whoever garnered the first compliment after arrival. After all the sweat-soaked work autumn workouts and trying to cut back on beers, other than football Sunday of course, I admired my toned body in the floor to ceiling mirror. But hey, nobody wants to hear about me.

As Lynn popped off her top and slid down her jeans with her back turned to me, I took in her stunning results. She looked spectacular and I'm pretty sure that she knew it. Being a proud second-generation Hong Kong woman, losing a competition wasn't in her wheelhouse. I gazed at her coconut-coloured bubble butt and immediately accepted that I was on the hook for a pair of 60 oz bottles of Rum & Tequila.

I wasn't surprised at how good Lynn looked, but I was caught off guard when she reached into her suitcase and tossed a pair of swim trunks towards me. I stood naked, now holding a black spandex pair of boy shorts. Lynn had bought me Daniel Craig short-legged, draw stringed trunks and she gave me the biggest wink possible as I did a double take at what exactly I was holding in my hand.

"Really? C'mon. I don't think I can wear this in public?" I replied as I studied my new apparel with the demeanor of a court judge.

"Oh, if you're uncomfortable with wearing that, I probably won't be comfortable wearing this." Lynn replied with all the sarcasm in the world.

Lynn, still with her naked body turned away from me, daintily reached into her suitcase and pulled out some white material. Dramatically, she pirouetted around holding both pieces in each hand and I took in her perfectly petite body all at once with a bit of a shock. I stood in naked awe as I admired her perky tits, dark nipples and suddenly totally bare pussy.

As a woman, Lynn easily traced my man gaze, and where it was directed. Sure, I was holding James Bond swim trunks in my hand, but I was certainly not a super-spy.

"Do you like my new look? I'm wearing white, and you're wearing black"

I nodded in agreement as I marvelled at my wife's pussy that had been waxed clean for the first time in her life. Lynn shimmied herself slowly into her brand-new bikini. She looked incredible as she slid her bottoms up and asked me to tie her top behind her back. I made sure that my immediate hard-on landed between her tight cheeks.

"No time for that big boy, we're beach bound!" she rudely exclaimed, and I stuffed myself into her version of a joke disguised as a bathing suit and followed her to the beckoning beach.

The Beach

We made our way down the white sand pathway and towards the lone beach that was the signature setting of the mildly outdated resort. I kept a towel wrapped around my waist to hide my new-found European look as Lynn sashayed under a floral cover up. I was feeling nearly every emotion between petrified and ecstatic. We hadn't traveled in years and we hadn't seen Gavin and Vee and I have never worn a "hot-guy" swimsuit and I was worried that I....

"Oh hello. What are you doing here?" Vee cooed from a lounge chair.

Here we go. Vee, in sunglasses with her wavy red hair, was reclined comfortably and was also comfortably showing off her curves in her green bikini. Of course, she looked amazing wearing green. Of course, her pale white skin was shiny and smooth, lathered with an extra layer of sunscreen. And of course, she popped up to embrace Lynn in a full hug.

I accepted my squeeze from Vee gratefully and then extended a handshake to Gavin, receiving a hearty return. Gavin popped up and gave Lynn a full hug and we were off and running. They even had a beer and cocktail waiting for us. After some small talk, Lynn and I made eyes and prepared ourselves for our "big reveal" and to see if there would be a winner of our bet!

I dropped my towel and Lynn shed her cover-up simultaneously, waiting for the first compliment. Bottles are at stake.

"Whoa. Are we not the hottest couple here? This is very concerning to me." Vee sarcastically observed as she grabbed Gavin's arm.

"That's a tie! That's an equal compliment!" I announced and then took a chug of beer and ran into the waves with college boy enthusiasm. "It's a tie!!!!!" I yelled again as my voice surely faded away with each sandy step towards the sea.

It was so nice to be in the ocean for the first time in years. It was so nice to see the waves wage war on Lynn's and Vee's bikini coverage. Lynn looked incredible in her white, sleek, low-cut top and half bottom.

I made small talk with Gavin, but I was having trouble keeping focus. It was too much to see Lynn and Vee bobbing up and down in the ocean. Lynn was adjusting her small triangles to keep brown nipples hidden and Vee was a little too quick to help Lynn out in this regard. I could tell Lynn was slightly embarrassed to have Vee pawing all over her new suit, so she took to the offensive. Lynn pulled Vee's top down and her massive creamy white tits spilled out for all to see.

"Am I helping, Vee?!?!?" Lynn chided, like they had been 4-year college dorm mates.

Gavin and I immediately swam towards our wives, but with unknown intent. Were we gonna separate them? Fuck them? or both? Vee proudly left her beautiful, freckled breasts out on display, floating happily in the salt water for a few moments.

"Can you too compose yourselves?" Gavin asked, as Vee meticulously worked her green bikini top back over her floating rack. After laughs and a few more splashes against the waves, Lynn and I made our way back in. Done towelling off, Lynn led the way back to our room and it wasn't the route I would have planned.

Lynn eagerly strutted her tight tanned body through the beachfront restaurant turning nearly every head as she went. Wrapped in my towel, I was happy to enjoy the view from behind. Lynn, who has been full of surprises lately, stopped at the patio exit and reached down to adjust her sandal strap. Was she kidding me? Her beautiful little ass nearly on full display for the dozen guests relaxing at the patio. Turns out, she was kidding me! As I approached her, she tore off my towel and quickly wrapped it up in her hair. My rock-hard cock, pressed to the right side of my hip, was as obvious as all hell. My sunburned face turned a darker shade of red as I heard gasps and laughs as I tried to calmly pursue Lynn back to the room.

As soon as we got to the suite, Lynn burst out laughing at how embarrassed I was and how she got payback for me calling "tie" on the beach. I wasn't in the mood for jokes. I was in the mood to fuck.

Lynn stepped out on the sun-soaked balcony to set the beach towels out to dry and I followed her, grabbing her small waist and pulling her in to kiss her soft neck from behind, easily done under her short haircut. After a breathy exhale from Lynn, I spun her around and dropped to my knees all while sliding her bikini bottoms down in one swift motion. Her smooth caramel skin and coffee colored pussy was too appetizing for me to resist.

Lynn didn't totally submit immediately, as she leaned back against the railing and swivelled her sightline from side to side to survey the situation. With no obvious on-lookers in sight, she relaxed and grabbed the back of my head and pulled me deeper into her pussy. Working her wet clit with my tongue and squeezing her toned ass, I could tell that my efforts were paying off as her legs started to tremble and her grip on the back of my head tightened.

Lynn started to pant and moan between heavy breaths as she adjusted her grip on the aluminum railing of the balcony. I steadied myself and slid two fingers into her damp bare pussy, slowly but surely. Pumping in and out while lapping her aroused bean sensually, Lynn was doing everything that she could to contain her screams. I looked up to see her covering her mouth with her hand. I could feel her moisture run down my wrist, run down my arm, run down the inside of her legs creating a rendition of a Jackson Pollock on floor of the tile balcony.

It was my time now. I popped up to my feet and easily spun my tiny wife back around to align her sopping wet puss with my stiff laser. Quickly, I popped my cock out of my ridiculous bathing suit, I slid it immediately inside Lynn's wanting cunt. I pulled down her bikini top so that I could squeeze her sweet handfuls as we both faced out over the balcony.

It was an overlapping cum for her as she screamed loudly while bracing herself with both hands on the railing. That's when we both became aware of the smiling faces of the resort staff cruising by extra slowly in their golf cart below. Busted! Lynn twisted away and bolted back into the room faster than I anticipated leaving me alone, fumbling to get my full mast back into my Scandinavian suit. 007, eat your heart out. I was shaken, but not stirred.

The first night of our first vacation in years left our cheeks hurting from laughter. A double date with Vee and Gavin began at the torch lit patio restaurant and ended with the sand between our toes as the full moon lit the sea. We comfortably joked about our sultry past, which was a welcome surprise. Also, Lynn and I made them both gasp with our dual re-telling of our balcony blunder. Ah, tropical nights.

Day 2

It seemed way too early in the morning for the athletic feat of taking a running leap from a solid dock onto the bobbing platform of a boat, but here we are! Gavin set up an island circumnavigation on a 75-foot catamaran and our bags were packed and we were game.

What a tour. With 20 guests and 7 hardworking crew, it was a perfect day. The food was delicious, the drinks tasty, the sun was toasty, and the scenery was special... and that included nature itself. Amid the aquamarine waves, rocky cliffs arose, dotted with the deepest of green flora that sat proudly under a marble blue sky that happily hosted friendly fluffy clouds.

Sunglasses were in order to appreciate the true beauties on this boat. Lynn's swimsuit, version 2.0, was a scandalous 1-piece. It was a sleek yellow and white argyle pattern that disappeared into her round tanned cheeks. I saw her hold it up before packing it, but to see the fabric hug her subtle womanly curves was certainly a pleasure. Who was this proud exhibitionist, comfortable with her fit little ass on display and a neckline that fell to nearly her belly button? Not the woman I married, but the woman who she'd become... since meeting Vee.

Lynn's competitiveness was showing as clearly as her cleavage. Vee will never be outdone, looking like a Playboy Vargas Girl circa 1965. Her hip-hugging floral bikini was hanging on to dear life with each bouncy step on the deck of the yacht. It was all capped with a pair of Jackie-O sunglasses and a floppy sun hat, that was destined to be blown overboard at some point.

Our day was full. Swimming was soothing, snorkeling was frightening, tanning was blissful, and relaxing was relaxing. I was now feeling much more like myself in a pair of grey skater style trunks and was having a great time chatting with the crew and other guests.

We met a pair of young couples from Ohio that were excited toss back beers and toss a football back and forth. The dudes, Devin and Xander were impressed by my arm. I was more than happy to sling a couple of sharp passes to them on the beach. With a few early grey hairs in my brown and black beard, maybe they were just more surprised than impressed.

Vee and Lynn were happy to meet their girlfriends, McKenna and Selena, and even more happy about making fun of the guys.

"Ugh! Pass me the ball! I'm open!" Vee imitated in her lowest voice possible.

"I coulda played for the Cowboys, ya know?" Lynn yelled in her most jock-tacular accent.

Embracing the trash talk, I cranked out a "Blue-42, Omaha! Hut Hut!" dropped back and lobbed a 25-yard pass toward the huddle of girls. Three backed away from the nerf football like it was a live grenade, but Selena, while holding a seltzer, snagged it easily with one hand.

I had to run over and give her a high-5. Devin screamed "Nice catch babe!"

Devin and Selena, Xander and McKenna, were on their first couple's vacation and were having the time of their life. We shared laughs, stories and phone numbers as we created a WhatsApp group named "The Magnificent 7...and Vee."

That was Gavin's title choice and it earned him a shot in the arm from Vee, that did eventually bruise. However, the name remained.

The day ended with a splash in the salty water and a fabulous fish-fry on the beach that was lit by the slowly setting sun. Then the night began with an invitation from McKenna and Selena.

"You guys want to come out with us tonight?" McKenna asked, squeezing Lynn's arm with sophomoric enthusiasm.

The Beach Club

"When was the last time we danced?" I asked Lynn as we hopped out of the resort shuttle van. "Must have been at a wedding." I pondered as I answered my own question.

Lynn and I agreed to checkout the beach club excursion that McKenna had arranged for the squad earlier in the day. Lynn and I took them up on the offer, but Gavin and Vee bowed out. Not a surprise as they both were napping on their loungers by the pool at 7pm.

"You have successfully arrived at your destination! Just walk towards the main entrance and follow the torch lights down the path on the left side and tell them Ozzie says hello!" The driver laughed heartily in his welcoming island accent.

The six of us were off. I embraced the smell of the sea air while walking under the beauty of the foliage-built archway that sloped down to the growing sounds of laughter and bass music. It all gave me chills.

Lynn moved seductively in her 3-inch wedge sandals that emphasised her toned smooth legs that flowed up into a flowy floral-print skirt that was probably 2-inches too short to be worn in the daylight hours. It matched her silk white tank tap and the bandeau that she popped into her hair. Her outfit made her look like a too sexy Hawaiian travel model.

Devin and Xander may have co-ordinated their outfits. Both dudes were wearing flip flops with shorts and loud, but stylish, patterned short sleeve shirts. They were lucky men as Selena and McKenna were stunning as they playfully held each other's hands while leading the way like half drunk explorers.

McKenna pranced happily in her black jumper with a plunging neckline that showed off her thin runner's body. Her strawberry blonde hair, now in bouncy curls, bobbed with each careful step. Selena was rocking a beautiful long red dress that showed off her Latin curves. Her body could do much more that catch a nerf football. Selena's straightened dark hair fell halfway down her back, just short of her ass that moved with the healthiest jiggle.

The night was a blast. Out of politeness, Lynn and I agreed not to tell Vee and Gavin tomorrow about how much fun we were having. The stars shone overhead as sweat shone off our skin. We had a pair of patio tables pushed together for ourselves that was served as our home base as our empty glasses and bottles grew like a miniature skyline.

We took turns admiring our dance moves, talking about our hometowns and downing shots. At one point Lynn grabbed my arm and pulled me back out to the floor for a sultry Rhianna song. We always had loved to dance together, and we were back in the vibe tonight. She moved so well, twirling her hips seductively, making her skirt spin into the air showing off her bare legs, and probably the cheeks of her ass. If you were lucky enough to be at right angle while sitting on the sidelines, I'm sure that you would have appreciated the view.

I pulled Lynn into me on rhythm, pressing my growing bulge into her rump. Grinding tightly, sliding my hands up and down her sides, being sure to tease her braless tits in her silky top. I planted a kiss on her neck and appreciated the salty taste of her sweat. I spun her back around to face me, grabbing hold of Lynn's butt and pulling her back into my hard cock that was restrained by my khaki pants.