Flirty Holiday Resort Vacation

We kissed again, longer, more passionately. Lynn had wrapped her hand behind my neck and was making a point to prolong this caress. I had to break our lip lock by grabbing her hips and lifting her up to me. She wrapped her legs around my back. We looked at each other and laughed.

Alcohol was playing a factor here, but Lynn was surely feeling herself. She was letting loose this entire trip and it was awesome to see. I can't believe that I was the one in this instance to pump the brakes, if ever so slightly.

As we made our way back to the table, we were greeted by guys holding up their napkins written like makeshift score cards, with a printed 10 from Devin and a 9.5 from Xander.

"9.5?!?" I exclaimed in mock rage.

"Technical Merit deduction. An obvious misstep on the lift element of the routine" Xander said with a straight face.

McKenna was fanning herself with her hand and Selena playfully wiped her brow with the back of hand, both in jest, but both as a compliment of how hot they thought our little number went on the dance floor.

The evening seemed to tick by at double time. We had so much fun laughing, drinking and flirting together. I think we each drew a lot of positive energy from each other. The young couples seemed to be enamored with us, like an older sibling's coolest friend.

McKenna even slid sexily into me for a song as Xander wasn't much of a dancer. She had moves and I enjoyed my firm grip on her slender waist. Lynn slyly smiled my way as she enjoyed the show. Lynn and I secretly named our four new friends the "Buckeyes", being that they were from Ohio. We felt that they looked at us and were trying to game out what the next 7 or 8 years into their future may look like for themselves.

However, in the present, Selena's phone started beeping at an implausible noisy level. "Oh my god! The Shuttle! Ozzie!" she shouted into her glowing phone. Our chariot had arrived.

We all crashed into white shuttle van. Xander sat up front with Ozzie and the trio of Selena, Devin and McKenna filled out the middle section and Lynn and I slid into the back. Lynn was momentarily surprised when she bumped against a dozing security guard that was taking a snooze in the corner seat. Malik, or so his nametag indicated, hardly flinched when the six of us squeezed into the van.

The ride to back to our resort was probably 15 or 20 minutes away and those in the front started a conversation with our lovable driver, Ozzie. He put on some music, assuming our little party troop would be appreciative, and he was completely correct.

I slid my hand up Lynn's smooth inner thigh while giving her a soft kiss on her neck, just under her ear. She let out a deep breath and closed her eyes. My hand continued to move up her legs and my kiss turned into a harmless bite on Lynn's neck, just to see how she would react. React she did, in all positivity, with a quiet exhale. Our dancing wasn't just for fun.

I peaked over to Malik, to verify that he was still in dreamland, and slid my hand up against Lynn's panties. They were already wet. I gave her pussy a soft circular rub over the moist fabric to illicit a soft moan.

"Ozzie? Do you mind turning up the music a little bit?" I asked. He followed suit without even acknowledging my question, clearly, he was enjoying the attention of the kids up front.

With the music louder and the darkened back seats of the late-night shuttle ride, I made a quick and deliberate move. Reaching down with my other hand, I hooked my fingers on the hips of Lynn's panties and slid them down and off her legs in a mere second, then stuffed them into my pocket. Lynn opened her eyes wide, surprised at the suddenness in which she found herself commando under her skirt.

I went back for a deep kiss and while sliding my right hand over her smooth and now slippery pussy. I loved the way her soft lips and wet clit felt on my fingertips but could only imagine the sensation Lynn was feeling as the cool seaside air blew in through the open windows up against her bare legs and exposed pussy.

Despite the music being played much more loudly, Lynn buried her head into my shoulder and bit the collar of my dress shirt to stifle another moan. She reached down and aggressively started at undoing my belt and zipper of my pants. It's way easier to subtly rub a pussy than to jack off a cock, but in the dimly lit back seat of the van, Lynn apparently felt the risk was worth it, and I wasn't going to argue.

Within seconds, my swollen vanilla creamsicle was out and being treated by Lynn's delicate strokes. I focused on trying to keep my forefingers rubbing Lynn's velveteen clit as her skirt slid further up her legs. That's when McKenna turned her head around and said, "Do you think the snack bar is still open at the resort?"

"Not sure. We're just taking a quick snooze" I replied lazily as possible.

Thankfully, McKenna turned back around and continued her conversation with the others. In the back seat, my cock was at full length being stroked by Lynn's aggressive right hand. We suddenly heard Malik clear his throat and give a sleepy cough. Lynn and I froze in our scandalous position. We both peered over at him from the very corners of our eyes to see him shift slightly in his seat and place his right hand on his lap.

Unexpectedly, Lynn started stroking my cock again. Slowly, surely, up and down. With the green light given, I slide my fingertips in slow concentric movement on her weeping cleft. I knew that I was growing close as Lynn picked up the pace and she wasn't that far off either as she began to purse her lips to conceal a wail.

Movement! Malik began to shift in his seat in the corner and we could feel his jostling clearly in the cramped back seat. It seemed like 30 seconds of tossing and turning in his corner spot of the van and it was difficult to tell if he was awake. As we both tilted our heads to see if we had been busted for the second time in two days. We got a huge surprise as the van passed under one of the rare streetlights on the island.

Malik had his entire cock out of his black security slacks, and he was secretly rubbing it up and down with his finger. He was busted. We were busted. We were both busted. His eyes appeared closed, but really, were they? Upon this discovery, Lynn looked up at me and we kissed, and we both resumed our acts. It was crazy, but I think that we were both too horny to stop. Also, there was nothing about Malik spying on us that was unsexy.

Lynn brought her right hand up to her mouth and gave her palm a wet lick and wrapped it back around my shaft. Then, she made a point to earn my gaze as she did the same thing to her left hand. Licking her hand more slowly, more deliberate and with a faux innocent facial expression, as if asking for permission. With my cock as hard as it could get, while rubbing Lynn's pussy as smooth as it could get, I managed a small gasp with a slight eye roll that indicated "we've gone this far, so..."

In a moment, Lynn's lubricated left hand reached over and wrapped it around Malik's throbbing meat. He sighed loudly. We knew that we were on the clock until arriving at our destination, so Lynn picked up the pace. Sitting in the middle, I couldn't believe that I was watching my sweet innocent wife stroke two big cocks in unison with her little island skirt up around her waist with her bare pussy on display. The sporadic rhythm of the streetlights lit up our lewd backseat lovefest like a filthy peep show.

I knew that we were now about 5 minutes from our destination, as the van hit a very bumpy section of the road that we experienced on the initial trip. With each bump, Lynn's hand squeezed our shafts harder and more erratically. With each bump, the straps of Lynn's silk tank top slid down her smooth Asian shoulders. I licked my fingers once more and gave Lynn's clit a final ferocious swirl. She buried her head in my shoulder as she began to cum.

As she intentionally muffled her orgasmic cries in my shoulder, one last giant pothole jostled the van so hard that Lynn's perky tanned titty popped out of her silk top. Malik's eyes went wide staring at her dark rubbery nipple, now completely exposed in the backseat as she cranked his chocolate-colored baton with vigour.

As streetlights illuminated the van with increased frequency. I knew that we were getting close to home. I grabbed the back of Lynn's head and forced her down on my cock and she knew why. I filled her warm sweet mouth with all my cum. Interlocking my fingers behind my head, I let out the longest sigh possible. I had to look over at Malik to judge where his status was at, as Lynn was still pumping his swollen cock and doing her best to swallow my load discreetly.

Malik nearly froze but found the strength to reach down and angle his thick monster to a lower trajectory so not blow his load onto the shoulders of the innocent bystanders seated ahead of him. I'm glad I asked Ozzie to turn the music louder as Malik's blast hit the back of the seat like rain on a tin roof. He tried to stifle a gasp with a courtesy cough.

"Malik my man! You awake now? I worked the graveyard shift too. It will all be worth it my friend." Ozzie proclaimed from the front seat as the van slowed and then parked in the roundabout of our resort entrance.

Lynn pulled her tank top back up and her skirt back down. Malik and I tucked ourselves back in and zipped up as we waited for everyone to exit, before sheepishly stepping out of the shuttle.

"Ozzie? Can you pass me those wipes? I think I smudged the windows back here during my nap" Malik asked with the politeness of a medieval squire. I, Lynn and Malik all made a knowing, approving, awkward but accepting head nod of acknowledgement to one another.

"Hey hotties, you have it in you for a night cap?" McKenna asked.

I spoke for the both of us, "Thanks, but I think we're spent for the night. Super fun night! Maybe see ya'll tomorrow."

Day 3

Today started the way I wished that every day would start for me, with my stiff morning wood deep inside Lynn's warm mouth. The sun spilled into our room, illuminating Lynn's naked body on all fours as I took in her cute tan lines on her shapely buns. I knew exactly what she wanted. We had a give and take relationship. She was giving me a good morning blowjob and she was getting ready to take a good afternoon slamming.

As much as I was enjoying pulling her short dark hair into my throbbing good-morning cock, I popped up on the queen size bed and pushed Lynn onto her back and sild my soaking wet serpent into her brazenly bare cunt. Grabbing both her wrists above her head, I started to plow away as my wife started to gasp and whimper.

I loved looking down on Lynn from above to see her cute tits bounce with every thrust. I was still having flashbacks of her wanking off a stranger and myself in the back of the van last night. I pumped her hard and fast and she clearly didn't care or didn't remember that the windows were left wide open as yelled out "Don't stop! Don't' stop! Right there. I'm cummmming!!"

This was the point when I looked down at my wife's bare Asian pussy and knew that I was gonna make her tight little body dirty. I pulled my firm schlong out and exploded my milky white cum all over her writhing torso. God, she looked good covered in my cum, and didn't she know it. Lynn gave me a satisfied smile as she lay sweat-soaked on top of the sheets in our seaside suite.

After a morning sex session like that, it's sort of difficult to really get after the rest of the day with the same enthusiasm. However, we shambled ourselves to the private beach to see Vee and we somehow found the inspiration to continue the day. Vee's yellow bikini bottoms were an afterthought of coverage and her top was untied as her slick creamy skin was doused with sunscreen.

Gavin emerged from the little beachside tiki bar with a couple of mimosas. Great timing. We spent the day talking, swimming, laughing and generally having a flirty good time. Gav and Vee were excited to here about our night out with "The Buckeyes". We couldn't keep it a secret about how much fun we had. We did keep the secret of Lynn's "rowboat" experience with Malik and me.

I was happy to deliver a little surprise as I booked a sunset horse ride for the four of us. It was an incredible experience as not one of us had ever ridden a horse before. Our guides were a riot and they seemed to make extra sure that Vee's voluptuous body was safe and secure atop of her caramel-coloured stallion. I don't blame the guides in any way. The rest of us kind of figured it out on our own. Watching Vee's red hair flow in the wind and her tits bounce in unison with the trotting equine was delightful. Lynn and I rolled our eyes in amazement at the exact same time and burst out laughing.

"What's so funny?" Vee questioned with suspicion.

"Nothing. I just think that we should ride horses more often" I replied with my best attempt at keeping a straight face.

"I also agree with more horse riding." Gavin replied.

"Nope, not for me!!!" Lynn yelled as her brown and white speckled mare wandered aimlessly into the ocean.

The guides quickly corralled the wayward horse to get Lynn back to the beach and we all took amazing photos holding the reigns of our new four-legged friends as the sun set in the distance.

That Night

We had a delicious fish dinner that warranted second and third servings. Lynn and I decided to call it a night around midnight as the wine hit her a little harder than she was ready for. On our beachside walk back to our room, I noticed a familiar figure wrapped in a blanket on a lounger in the sand.

"I think that's McKenna?" I mentioned to Lynn. I could see a glowing ember that indicated a lit cigarette or maybe a joint and became curious to the scene. Lynn's focus was on getting home and getting into bed, but she gave me the go ahead to check on her.

"Hey, what's up McKenna? It's me, Shea." I said as I cautiously approached.

"Oh hey, how are you? What's up? How's your night going? You good?" she questioned in rapid succession, clearly surprised by presence while wiping her eyes.

"I'm good. All good. You good?" I asked.

McKenna, with her teary doe-eyes, explained how her and Xander had a fight. I was suddenly in their drama and wasn't super excited about it. She offered me a cigarette as I took a seat at the end of the lounger. I enjoyed my first smoke since my bachelor party. She explained that Xander and her had broken up before the trip but being that they already had paid for the entire package, decided to come together as friends. The "friends" part clearly wasn't working for McKenna as Xander was flirting with every girl on the island and was no where to be found tonight. She still had feelings for him.

The young sweet girl stopped mid-sentence and leaned forward and gave me a hug and thanked me for listening. I reassured her that she had Lynn and I's number and to shoot us text if she needed anything at all. I reminder her that she was in paradise and she made the right decision to got through with the trip. Savour these memories, good and bad, and to sweet fuck with regrets.

"Yeah, fuck regrets. I'm on holiday!" McKenna yelled proudly with confidence and tequila breath.

She expressed her appreciation for my guidance, and we exchanged another embrace. Under the full moon and the lapping waves, I felt nostalgic talking about relationship troubles, almost like I was back in college.

"You think we can still get a drink at the bar?" McKenna questioned.

"Maybe? It'll just be one for me. Let's check it out." I replied.

Walking back to the resort, I was hoping that Vee and Gavin were still there so that we could join them. No such luck. McKenna instructed me to grab a seat as she would get drinks. The terrace table I choose overlooked the crescent beach and the starry sky and McKenna quickly returned with two pints and two shots. I was very sure that I said one drink.

McKenna lit up as the shots were downed and the conversations continued. We talked about her and Xander, me and Lynn and growing up in the mid-west. Her older brother worked at the Six Flags when Lynn and I saw a punk concert there years ago. Six-Degrees, right?

After our pints were vanquished, the lights of the patio were dimmed, I started into my goodnight sentiments. I asked if McKenna needed an escort to her room and she readily agreed. She clung to my right arm to steady herself as we ambled along the path to her room. I could tell that it was at least half intentional that she was rubbing braless tits against me as her pace slowed.

As we arrived at her front door, I said my good nights and good lucks as she fumbled to find her room key in her clutch. As soon as she found it, she looked up to me and went in for a kiss. I was slow to react. I let it land. She went for it and got what she wanted. Before I moved her away, I admit that I enjoyed the taste of her peach lip gloss and her tequila flavoured tongue. I did end the kiss, but with the slow subtly that didn't express complete rejection. McKenna didn't need that tonight.

I reminded her that she was cool, funny, smart, and absurdly attractive. I also reminded her that I was a married man. With that said, I did reiterate that she had Lynn and I's phone number and she could call us if she needed space from her Xander drama.

I started the walk home hoping that Lynn would still be up so that I could get this entire story off my chest, in its freshest form. No such luck. When I arrived, Lynn was snuggled into the blankets and merely mumbled at my presence back into the bed. One of these holiday nights will be normal, right?

Last Day

"Wow!" Lynn exclaimed with leaving her mouth agape in shock.

"Yep. I guess I still got it" I joked as I scanned Lynn's face for anger.

"I could tell at the club that she had a thing for you. I'm not surprised at all. That damn salt & pepper look of yours is a girl magnet." Lynn mocked as she held my beard and squeezed my cheeks together like I was a little kid who just ate a forbidden cookie.

"Clearly, you aren't that mad. That's good." I said hopefully.

"No, not really. I might be mad if I see McKenna, but whatever. Who can blame her? Fight with her boyfriend on a tropical island. She shot her shot with my sexy husband. C'mon. It's our last day, let's make it count!" Lynn said as she intentionally bent over extra slowly to show off her tanned caboose as she picked up our beach bag.

The sun belted down with extra force today as I admired Lynn's shiny body absorbing the afternoon rays. Her tiny black bikini looked amazing on her tight curves. She was looking like a character in a James Bond movie today. Her perky breasts pointed beautifully to the sky and just beyond those sweet treats were the beautiful curves of Vee's cheeks lathered in sunscreen. Vee's body was only covered by her red thong and SPF 40. Her round breasts were crushed to the lounger as her top was strewn on the sand, draped over an airport paperback.

I wasn't happy that Lynn forced me to re-tell the story of last night with McKenna for Gavin and Vee to hear. Vee made sarcastic jokes and riffed on the situation. She had a sharp sense of humor. I felt bad for McKenna though and hoped that she was doing okay, but also realized that the best plan of action was to avoid any further drama.

The four of us celebrated our final day with a last island excursion that was highlighted by a scenic sunset tour that concluded atop a rocky terrace that looked out across the Caribbean. Lynn and I gave each other a knowing look when we slid into the backseat of the van and burst out laughing. It had been thoroughly cleaned since our last trip.

The champagne sunset celebration was needed as we couldn't help but feel some growing sexual tension building as the hours began to tick away. The rum shots were also needed at dinner as well when we returned to the resort. With everyone feeling a little more relaxed, a little more comfortable, leave it to Vee to become a little more bold.