Sarah's Cuban Vacation

There is some French-Canadian swearing in this story. While the literal translations have a religious meaning (the tabernacle, the chalice, the ciborium), in this context they mean "OMG", "holy fuck" or "daaaaamn girl."

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My wife Sarah and I usually try to break the winter up with a trip to the Caribbean. Her older sister Jo had recently divorced, and since her 40th birthday was in February, we decided to bring her along to celebrate the milestone.

After spending a couple of weeks shopping around, we stumbled into a good deal that just happened to be for the same Cuban all-inclusive resort we had stayed at the previous winter. Since Sarah is the life of every party we had gotten to know most of the resort workers, and looked forward to reconnecting with several of them.

Rather than have Jo fly alone and meet us down there, we decided to travel the 1000 km to her place, so that we could all fly down together. We arrived at her place around 7 PM and had a pre-vacation cocktail together.

We awoke the next morning to a surprise snowstorm, that lead to a series of delays and resulted in our mid-morning flight being rescheduled to early evening. When we arrived at the airport and cleared customs, there were still another 4-hours until boarding. We found 3 seats together in the departure lounge, and settled in for the wait.

Since I'm an avid reader, I had packed a couple of novels for the week, and figured now was a good time to start one.

"Hey Sarah, can you pass me the Lee Child I packed in the carry-on?" I asked.

"Sure." she replied. The bag was on the floor between her feet, so she bent over and unzipped it. As she felt around for my book, she happened to look down and noticed that her neckline was gaping, and she was putting on quite the downblouse show for anyone who might be looking. She glanced up to check the lay of the land and immediately locked eyes with the gentleman sitting directly across from her.

He was a huge mountain of a man, perhaps 6'-5" or larger, with a ZZ Top beard that was just starting to show flecks of grey. He had two complete sleeves tattooed on his well-muscled arms and was wearing a bandana with a ponytail sticking out the back. He was either a biker or a Viking, and his Harley Davidson t-shirt led her decide it was probably the former.

Sarah's options were cover up, feign ignorance or flirt. Emboldened by 'Biker Dude's' smile, she chose flirt. She passed me my book, then began chatting with her admirer while she continued to be hunched over reaching into the bag.

"Are you heading to Cuba too?" she asked.

"Yes." he replied, speaking with a big bold French-Canadian accent, "I'm meeting up with 4 buddies I've known since kindergarten to celebrate our 25th high school reunion. I'm Marcel."

Sarah finished zipping up the carry-on, then reached across the aisle to shake hands, not exactly increasing her exposure, but giving him a closer look down her cleavage. "I'm Sarah, this is my husband Brian and my sister Jo. We're heading down to celebrate her birthday."

"Nice." he said, "Where are you staying? We're at the Chevy's."

"Same with us." she replied, "Where are your buddies?"

"They all still live back in Montreal, so they flew down together yesterday." he answered. "I was supposed to be a day behind them, but with these delays it'll be almost two by the time we get to the resort."

There was some good banter back-and-forth and we eventually discovered that he used to be a coach on Jo's son's football team.

"Dude is 6'-5..."

"6'-6" corrected Marcel.

"My apologies." replied Sarah, "Dude is 6'-6", handsome, bearded, tattooed and has beautiful hair and it took you 15-minutes to recognize him?"

"He was a defensive coach. Calvin was a running back. We didn't associate much with people from the less talented side of the ball." Jo teased.

"Oof! That hurts." Marcel replied while mockingly rubbing his heart.

When a seat became available, he moved his bags across the aisle to sit with us for the rest of the wait.

When we finally prepared to board, we discovered that we were in different sections of the plane, so the ladies each hugged him, I shook his hand, and we made plans to catch up on the other end. An uneventful 4-hour flight followed.

After clearing customs, we headed out to the parking lot to find the bus that would take us to the resort. The girls got on the bus to find us seats while I stood outside waiting for the bus driver to stow our luggage underneath.

On the bus we found that Marcel had saved an entire row for us. Jo and Sarah were in the two window seats, with Marcel in the aisle beside Sarah, leaving the aisle seat beside Jo for me. All three of them were drinking cans of Cristal beer.

Each bus has a tour guide who doubles as bartender to sell 'bus beer' for the 45-minute ride to the hotel. Marcel had bought 10 cans for our group while he was waiting for us to arrive.

"Brian, here's a Cristal." said Sarah, who stood up and reached across Marcel to pass the can, her boobs were an inch from his face. She paused and looked down, noticing that she had indeed caught his attention.

It was approaching midnight, but the mood on the bus was light as everyone was finally on vacation.

"We're in Cuba!" Sarah toasted and put a hand on Marcel's thigh so she could reach across and cheers Jo and I, then turned to cheers him, affording him a very close up view of her cleavage. She then sat back down, but faced sideways so that she could continue to talk with us, her hand remaining on Marcel's thigh.

When we arrived at the resort, we stood in line to check-in. Marcel's buddy Denis was there to meet him.

"Tabarnak Marcel, we didn't think you were ever getting here." he declared, adding "We're all down at the 24-hour snack bar waiting for you."

"I'll be down as soon as I get my bags to the room." Marcel replied, before looking toward us. "Are you joining us?"

"Definitely." Sarah replied.

After check-in, we took a shuttle to our rooms. Sarah and I shared a room with Jo. We were supposed to have two queen beds, but we ended up with two singles and a cot. We decided to take turns on the cot so no one had to spend a week on it.

After a full day of travel, Sarah decided to put on a fresh tank shirt. It afforded plenty of cleavage under normal conditions, but combined with her push-up bra the effect was almost 'over the top.' As we left, Jo stayed behind to get ready for bed.

Sarah and I met Marcel in the hallway. He had the room beside ours. We walked to the snack bar and found that Denis had gotten us drinks, so we sat at their table and were introduced to Ricky, Bart and Ti-Jean.

Sarah hugged everyone as the introductions were made. Her cleavage did not go unnoticed, and she became the center of attention at the table.

"So how did you guys meet up with Marcel?" inquired Bart.

"I caught him looking down my shirt." Sarah teased, getting a laugh from everyone at the table.

"So you have a weakness for perverts?" joked Ricky, "Good to know."

"No, I'm just good at reading people." she replied.

"Do us then." challenged Denis.

"Ok." she said. She moved around the table studying them all, occasionally stopping to get one of them to stick out their tongue or let her check their pulse. I half expected her to get someone to turn their head and cough, as I knew it was all an excuse to flirt a bit. In reality she was only looking at two things: their eyes and their ring finger.

"Ti-Jean looks like the kind of guy his wife would trust to have a little fun with the boys without crossing the line. Bart looks like the kind of guy you were all afraid would secretly bring his wife on the guy's trip."

They all roared laughing, before Bart added, "I asked but she said 'no'. She's flying in the day the boys leave and I'm staying an extra week."

Sarah nodded then continued, "Denis is on the prowl. Some sort of rebound perhaps? Marcel is also freshly single, looking for a little fun, but isn't ready for anything serious. And Ricky...you're going to be in trouble if your missus discovers no tan line under your wedding ring."

This resulted in some clapping for Sarah's performance before their attention turned to razzing Ricky.

Eventually Bart looked at his watch and noticed the time. "Guys, we have to be in the lobby in about 4-hours if we're going fishing. I think we should call it a night."

"Fishing?" asked Sarah.

"Yes, we're going deep-sea fishing for marlin." replied Ti-Jean. "Booking this excursion seemed like a good idea when Marcel was supposed to arrive early this afternoon. It's feeling like a miscalculation now."

Bart stood up, expecting everyone to follow his lead, but with Sarah being her flirtatious self, he had no takers. Wagging his finger he announced, "Every one of you guys had better be in the lobby at 5:30 AM.", then headed off to his room.

Marcel headed to the bar to get the next round, and since Sarah and I recognized the bartenders, we went up with him.

Carlos and Guillermo recognized her too, and their eyes lit up. "Hola mi amor" shouted Carlos, as he signaled her to come around behind the bar. Carlos gave her a big bear hug, then kissed her on both cheeks. After he released her, she got the same treatment from Guillermo.

"You arrived tonight?" asked Carlos, "Just one week?"

"Yes," responded Sarah, "Sadly, only one week this year."

Guillermo took Marcel's drink order for the table, and both bartenders started mixing drinks.

"I have this guy." Sarah said and started mixing my Cuba Libre. About one night every trip to Cuba, she ends up spending time tending bar. Apparently tonight was the night. She sat my drink on the bar in front of me, then stuck out her chest.

Having witnessed her bartending before, I knew the drill. I removed a bill from my wallet and folded it. I then stuck my finger into her bra and pulled it out just enough so I could see the top half of her areola. I paused to look at her face. She was staring directly at me with the beginnings of a smirk. When I didn't immediately continue, she raised an eyebrow. I then deposited the bill while releasing her bra.

She then turned to Carlos. He put his hands on her hips, leaned in close to her cleavage, removed the bill with his teeth, then dropped it in the tip cup.

"Umm..." Marcel interrupted, "I also have a tip for the bartenders."

Sarah turned toward him, and I could see a hint of mischief in her eye. "My husband is a big tipper. Do you have a big...'tip' for me?"

The innuendo wasn't lost on Marcel, who chuckled and swore, "Tabarnouche!"

Sarah put her hands on the bar, then leaned forward, thrusting her cleavage toward him. He removed a bill from his pocket and folded it like I had. He put his finger into her bra and gently pulled it away from her breast, took a brief peek at her nipple and nodded in appreciation. He then reached inside, cupping her entire breast and depositing the tip at the very bottom of the bra. He lowered her breast onto the bill, then removed his hand, dragging his fingers across her nipple on the way out.

Sarah raised one eyebrow to Marcel, even as she began to turn toward Guillermo.

The bartender reached into Sarah's top, while biting his tongue and looking skyward, as if he hadn't seen the bill being deposited and had to blindly grope around to search for it, and grope around he did. Eventually he removed the bill and held it in the air like a trophy, earning a playful slap on the shoulder from Sarah.

I helped Marcel carry the drinks back to the table, but when the boys heard about Sarah bartending, they all decided to go stand along the bar. When she saw us approaching, she unhooked her bra, pulled her arms through the straps and removed it through the arm hole of her tank top.

"Getting rid of this before it gets stretched out of shape." she said as she hung the bra from a bottle on the back shelf.

The tank top had a large logo on the front that prevented her nipples from being visible through the thin fabric, but with the way the tips were being delivered, this wasn't really a concern for anyone.

With the resort disco still hopping, there was a bit of a lull at the snack bar, so the 5 of us kept ourselves entertained by ordering different drinks from the menu, while the bartenders offered Sarah guidance. Then the drink recipient would make sure to tip generously.

"I'd like a pina colada." Ti-Jean said.

Carlos grabbed the blender and gave it a quick rinse, then handed it to Sarah. "If you go to the lobby bar they'll make it from scratch, but here at the snack-bar, we have to take shortcuts."

Sarah started off by using the scoop to reach deep into the ice chest to fill the blender with ice cubes. When she did this her shirt gaped out, rewarding Ricky with an explicit downblouse view. The rest of the crew started to crowd around the area of the bar immediately in front of the ice chest, anticipating this to be the best seat in the house.

Following Carlos' advice Sarah used the blender to mix the ice and a premixed drink pouch to create the frothy drink. Then she free-poured rum the Cuban way: locking eyes with Ti-Jean and pouring until he nodded. Using the mix from the blender, she topped off the glass. Finally, she leaned forward and waited to be tipped.

Staying true to Sarah's prediction, Ti-Jean didn't cross any lines and simply stuck the folded bill into her cleavage.

"I'll have a banana mama." ordered Denis.

"At the lobby bar they'll also make this from scratch, but here we'll just add a little grenadine and a splash of banana liqueur to the pina colada." explained Guillermo. "However, you don't want the customer to know that he's just drinking a red pina colada, so you distract him." Guillermo then spun and flipped the rum bottle like Tom Cruise in 'Cocktail'.

He handed the rum bottle to Sarah, as we all looked on expectantly. After a brief pause while she considered how badly this could go, she shrugged and adjusted her neckline so her right tit was completely exposed. Then she free-poured until Denis nodded for her to stop.

"Very good distraction." said Guillermo as we all laughed.

Sarah finished preparing the drink with her boob out, set the drink in front of Denis, then waited for her tip.

Denis folded a bill and leaned forward toward her boob, paused to look at Sarah and myself to make sure there were no objections, then planted a kiss on her exposed nipple while tucking his tip into her shirt in front of the opposite breast.

Sarah turned toward Guillermo, who also bent down and kissed her nipple while he retrieved the tip. She then turned toward Ricky while her right boob continued to be free.

"I want Sex on the Beach!" he exclaimed.

"Of course you do Ricky." countered Sarah.

Unfortunately for everyone patiently waiting by the ice box, the snack bar version of Ricky's drink was made using the slushy machine, so she wouldn't be needing ice cubes. She did however need to free-pour two different types of alcohol, all while under close observation by Ricky.

When Sarah was finished, she placed the drink in front of him and announced, " Ricky, I offer you Sex on the Beach."

"I accept your generous offer." he replied with a chuckle as he folded his bill. Then he bent across the bar as Denis had and took her nipple into his mouth and suckled until Sarah finally pulled away. He then casually dropped his tip onto the bar.

Around 2:30 people started to filter in from the disco and Sarah tucked her boob away, ending her extended exposure. With her spell broken the boys realized that their fishing trip started in less than two-and-a-half hours. We all reluctantly decided to call it a night.

Sarah gave hugs to Carlos and Guillermo and told them we'd see them tomorrow. Then she grabbed her bra and draped it across her shoulder while coming around from behind the bar. She gave Denis, Ricky and Ti-Jean each a hug since they were headed to a different building, and we both wished them good luck fishing.

With that we headed off toward our building, with Sarah arm-and-arm between Marcel and I.

When we reached the third floor, we bid adieu to Marcel and entered our room quietly so as not to disturb a sleeping Jo.

I entered the bathroom and got changed into a pair of boxers to sleep in. When I came out Sarah was waiting for me.

"We actually have a 3-bottle drink dispenser mounted on the wall." she whispered, "Let's take a drink out on the balcony and unwind before bed."

"Sure, what would you like?" I asked.

"Just pour me a small glass of the amaretto please." she replied, then went in the bathroom to change.

I put three shots of amaretto into a cup for her. Our other two options were white rum and vodka. I planned on having another Cuba Libre, however the fridge only contained orange Fanta and bottled water. So I decided to experiment and mixed the Fanta with vodka, and it actually worked. By midweek everyone in our group had tried my newly created drink.

I grabbed our drinks and went out on the balcony.

"Hola my friend."

I turned to see Marcel sitting on his balcony, which was only separated from ours by a waist high concrete balustrade railing.

"It looks like we had the same idea." I said, noticing that he was wearing pjs and holding a drink.

"Yes," he replied, "I was just going to have a quick drink before bed. Sarah call it a night?"

"I feel my ears burning." Sarah said as she breezed through the doorway. This was the first time I had seen the nightgown she was wearing. There was some very enticing cleavage on display, but nothing excessive. Marcel had certainly seen more tonight already. It was thin enough to easily locate her erect nipples, but not thin enough to be see-through.

What made this nightgown eye-catching were the two generous side slits that reached from the below her knee, all the way up to the bottom of her ribcage. Combined with her hourglass figure, the result was that her hips were completely exposed, creating the illusion that her legs were nearly 5 feet long.

It was obvious that she wasn't wearing panties, a fact not lost on Marcel when I heard him mutter "Ciboire" under his breath.

"What are you drinking Marcel?" Sarah inquired, as she took a sip of her amaretto.

"Gin and tonic." he replied.

"Really?" she mused, "That wasn't an option for us, they must put different bottles in each room. What else did you have?"

"I'm drunk and have been awake for 21-hours," he explained, "I didn't really pay that much attention."

"Ok, let's have a look then." Sarah said. She approached the railing and briefly considered the logistics of getting across it. "Could you move one of those chairs closer?"

Marcel and I each moved a patio chair close to the railing. I then held out my hand to help Sarah climb onto it. She led with her right foot causing the front of her nightgown to shift. While her modesty stayed intact, I started to have doubts that this would continue.

She brought her other foot up onto the chair. I then released her hand, and she took Marcel's hand to stabilize her while crossing to his side. Just before she stepped, she turned to look at me, bit her lip and winked. I wasn't sure what was in store but anticipated a case of "Que sera, Sarah.", which was a code of sorts between us. It basically meant 'I'm about to be seen naked because it's mildly inconvenient to avoid that outcome.'

She began to step across to the opposite chair, but as she did so the front portion of her nightgown, from one side slit to the other, was held back by the railing. The further she moved, the wider the gap became, her exposure gradually increasing. As her center-of-gravity crossed the railing, there was no turning back, momentum had now taken control. Her foot landed on the chair. With her back to me I couldn't view the exposure, but I knew from her bellybutton down it was total. This was confirmed by the smirk on Marcel's face. With her pussy nearly at eye level, he would have only had to lean forward a foot to bury his face into it.