All Inclusive - Day 01

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Rose enjoys being the only woman on a group vacation.
7.8k words
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Part 1 of the 2 part series

Updated 06/10/2023
Created 09/05/2021
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Based on a true story.

(Brief mention of marijuana use)

"Hey, Rose!"

I turned at the sound of my name. The sun was so bright here, I instantly reached for my sunglasses. Coming from snowy Iowa, I wasn't used to the warm island heat at the all-inclusive resort.

Cole, my boyfriend's best friend, waved me over. In no big rush, I grabbed a drink from the bar before I made my way over, draining it entirely before I reached him. I was going to get my money's worth out of this vacation. Since it had turned into a vacation for one.

"So he really didn't come, huh?" Cole asked once I reached him. Noticing my empty glass, he handed me another drink and I took it gratefully. "Yeah," I replied. "We had this huge fight about it," I told him. Looking sympathetic, Cole signaled the bartender to start on the next round.

Two days before we were scheduled to fly out, my boyfriend, Tyler, got a DUI and can't leave the state until the charge is resolved. He wanted me to stay with him, missing out on thousands of dollars already spent on this all-inclusive resort vacation, since it's nonrefundable so close to departure. He and four of his closest friends had planned this for over a year. I was invited since each dude got a plus one, and I was looking forward to a relaxing vacation after working hard for months. I told him I was still going, and he did not like that. Which lead to me leaving him to stew in his own mess, I was going to get my money's worth. What kind of guy drinks and drives anyway? I was determined to forget him. With the help of all the free drinks.

"Where are the others?" I looked around, but only spotted some of the other guys.

Cole looked nervous. "Well, uh, it turns out you're the only girl here. In our group I mean. The other ladies couldn't make it."

"What happened?"

"Miles' girl insists she's pregnant."

"What's this? Again?" I asked, trying hard not to roll my eyes. This was not the first time his girlfriend either thought she was pregnant or faked a pregnancy. To be honest, the group was a little sick of it by now.

"Yeah, so she is staying away from alcohol, and is staying home. Like you, Miles said 'fuck that' and left her there."

"Are they broken up?" I asked, curious. Miles and Vicky had been on-and-off for a year or two. I didn't know what he saw in her. He was hot, and she was super high maintenance.

"I don't think so, but they're both pretty pissed at each other."

"Ok, what about the others?"

"Nick's fiancé was never coming, remember? She's scared of flying. So he's here solo. And Charlie found out that his girl was cheating on him."

"Yikes." I felt for him, but I wasn't sure how comfortable I was being the only girl. I was already tipsy and Cole was looking even hotter than the last time I saw him. His biceps had filled out, and it suited him really well.

"Don't worry," he noticed my uncertainty. "We're going to still make sure you have a great time!" He said enthusiastically.

"Wait, what happened to your girl? Melina?"

He looked away, "we'll need more shots for that."

I couldn't agree more, so all I said was, "amen."

I purposely packed my skimpiest bikinis, hoping Tyler would see the photos and get jealous. I felt a twinge of regret now, surrounded by some of his friends, most of which were hotter than he was. But, with the more drinks I consumed, I figured that he'd be even more jealous if he saw me wearing them around his friends. Either way, I wanted to get tan and it's not like I brought any other swimsuits.

After dropping my stuff off in the luxury room I'd now be sleeping in alone, I headed straight for the poolside bar where I saw the guys (Cole, Miles, Charlie, and Nick) taking shots. Miles--who I considered the hottest of the group after Cole--had a set of waterproof playing cards out and was teasing the rest of the men into playing drinking games.

Apparently, Cole had filled the guys in on the Tyler situation, because the only comment when I got up to the pool was, "damn, Rose! Did you get hotter?" from Miles. I smiled and made him scooch over for me to slip into the pool. Seeing as we were a group of (mostly) single young adults at a legitimate couple's resort, we had a completely different vibe going on, and had a whole pool section to ourselves, surrounded by exotic plants that offered us even more privacy. We dove right into drinking games, and were soon getting really rowdy.

"Rose!" Nick shouted my name on his way back from the bar. I noticed he couldn't help but skim his eyes up and down my body. Yeah, this guy had a fiancé, but he wasn't blind. "I have more shots!"

"Oh! These ones look tasty!" I tilted back an opened my throat for the colorful, fruity shooter. Despite the number of drinks, I shivered in my string bikini. We had been in the water a long time. "I'm getting in the hot tub!" I announced.

No one else was in there, probably having been scared off by our drunken, loud antics. I dipped my toe in, and it was shockingly hot! I yanked it out, but overbalanced and almost fell in. Flailing, I knew I was about to plunge straight into the hot tub, and while it wasn't going to hurt, it was going to be extremely embarrassing in front of the guys. I was saved from falling in however, by someone's strong hands steadying me and pulling me back upright.

I gasped and looked up. Cole was smirking down at me. His dark hair was in stark contrast to his deep blue eyes, and it was mesmerizing. Several heartbeats went by before I broke eye contact. It felt a little too long. He let me go, and we both settled into the hot tub.

"Are you ok?"

"Yeah, just a little too tipsy, I guess. I haven't stood up in a while."

"You might want to slow down," he suggested.

"I know, but whenever I think about Tyler and our fight, I want to drink more. Might as well, right? It's included in the package, and we paid for two." I emphasized this by grabbing his drink and taking a sip. It was surprisingly delicious and fruity.

"What is this?"

"A Sex on the Beach."

I almost choked on the drink. I couldn't help but sneak a glance at him. I flushed red, and I hoped that if noticed, he'd think it was the heat from the jacuzzi.

"It's really good," was (lamely) all I could think of to say.

He signaled to one of the servers, always walking around and looking for whoever needed more drinks. He ordered another for himself and one for me.

"You want to talk about it?" he asked as we waited for the drinks. I knew he meant the Tyler situation.

"Not really, I know he's your friend."

"Yeah, but he's a fucking idiot. Drinking and driving is so stupid. He could lose his license and his job, in addition to all the money you two spent on this trip."

"Well, I don't plan on wasting it," I said, taking the drink the waiter offered when he returned. I took a sip, and Cole couldn't take his eyes off my lips, I could tell. I was horny as hell--Tyler was still in jail for the stupid DUI when I left--so it had been a while since I had gotten laid. And considering our relationship was in flux... I really wanted it. I had always had a thing for Cole, he was flirty and forward, but I've had to tamp it down over the months.

But I couldn't quite close the gap between us and kiss him. I knew he wanted it, and I could tell that he knew that I wanted it. He was waiting for a signal. But needed a few more drinks first, my inhibitions weren't quite free yet.

I took a big gulp of the Sex on the Beach, breaking the moment. "Where are the other guys?" I asked, noticing we were still alone.

"They're still in the pool. I told them to, uh, give us a minute."

I gave him a side glance.

"In case you needed to talk, that is." He quickly added.

I laughed. "Yeah, right!"

Miles' voice carried over from the pool. "Hey, quit hogging all the boobs! I have shots! Come play drinking games!"

I splashed out of the hot tub and Cole--looking a little reluctant--soon followed. I saw the guys had some kind of inflatable table and had set up the cards. Miles had the shots lined up outside the pool.

"Truth or Dare?" Miles suggested, waggling his eyebrows.

I laughed out right. "Isn't that a little childish?"

"How about strip poker then?" Nick asked.

"Truth or Dare sounds just fine thank you," I quickly interjected before strip poker got out of hand. We already didn't have many clothes on.

"Ok here are the rules," Miles explained. "You each get three strikes, or three shots. You can pass on a Truth or a Dare, but you have to take a shot. So, once you take three shots, you lose!"

Cole looked intrigued. "What do I get if I win?"

"Bragging rights?" Charlie suggested. I smiled at him. While handsome, Charlie was not the most creative of the bunch.

"I have an idea," Cole looked mischievous. He leapt out of the pool to grab something from his bag. "Whoever wins," he said, taunting us, "gets this." He whipped something out from behind his back. It was a huge joint.

The guys hooted and clapped. "Where did you even get that?" I asked, reluctantly impressed.

"It's easy down here. Come on, Rose, you saying you've never tried weed?"

"If I smoke that whole thing, I'd fall asleep within seconds!"

"I never said you had to smoke the whole thing, Rose. You can always share." He winked again, but with the support of the majority of the gang, the joint was put up as the prize. I didn't care, that just meant there was no pressure to win. I'd have a hit or two, but that thing was huge, and I didn't trust these guys not to draw a mustache on my face if I passed out around them. They were huge pranksters. I know none of them would go further than that if I passed out, but I'd be taking heat from the prank for the rest of the trip.

"Shouldn't the loser have to have some sort of punishment as well?" Cole asked, and I swear, he shot a glance at me, as if predicting I'd balk under the Truths and Dares they'd ask of me.

"Agreed!" Said Nick, who seemed to think of himself as master of the games.

"Loser has to pee in the ocean?" Charlie again suggested un-creatively.

I instantly turned red. All eyes swung my way. "I thought it was okay! They told me it was allowed!"

They all burst out laughing. Cole slapped me on the back, still trying to control his laughter. "It is, it's fine, Rose. We're just laughing at how red your face got!"

"Who is this mysterious 'they' that told you about peeing in oceans?" Nick pointed out. I just groaned.

After a little more laughter at my expense, they finally got around to the fact that Charlie actually suggested peeing in the ocean as a punishment and started to tease him about how lame it was.

"I got it!" Miles perked up. "Loser has to streak!"

"No way!" I protested. "You'd all gang up on me, I'd lose for sure!"

"Ok how about this," Miles tried one more time. "If you lose, you only have to take off your top or your bottoms. You don't have to go fully naked."

I considered for a minute. It still didn't sound fair, and it didn't prevent them from ganging up on me Before I could respond, Cole pushed a drink into my hand, encouraged me to take a sip, and while my mouth was occupied, he said, "she's in!"

Before I could protest, Miles graciously said, "and just so you know we're playing fair, we'll let you go first! Pick whoever you want."

"Charlie," I had debated a bit, but as the first person to request a Truth or a Dare from someone, it was a lot of pressure. I wanted to start things off easy, to set the tone on a playful note.

Charlie looked a bit nervous, but after some encouragement from Nick, he chose Dare.

"I dare you to pee in the ocean."

Miles almost dropped his drink; he was laughing so hard at Charlie's face.

"I, uh, don't have to go right now." Now everyone was laughing at how red Charlie's face was getting. While attractive, he hadn't spent enough time in the sun yet to darken his pale skin tone. And he blushed easy.

"Ok, well when you do have to go, you go in the ocean, or you take a shot."

Charlie was going to have a long night trying to hold it.

The night grew rowdier and rowdier. After my first Dare, Charlie dared Nick to moon the bartender, which he did proudly. The bartender, being a man, was not as pleased, but considering this was a couple's resort, I'm sure he has seen worse, because he handled it with grace. When Nick asked Miles, he chose Truth.

"So... Is your girlfriend really pregnant?"

"News flash: no!" He laughed. Vicky's constant pregnancy fakes and other drama were a routine joke amongst the guys, I could see. Tyler had mentioned it a few times, but I didn't want to think about Tyler at all right now.

"So, what," I interjected, "she let thousands of dollars go down the drain because she thinks she's pregnant? Did the test come back positive or something?"

"No, that's the thing. She didn't even take a test. It's just her instincts or whatever." I could tell Miles was fighting hard not to roll his eyes. "She's late, and she's convinced."

"How many times has she been convinced though, Nick?" I could tell Cole asked it in a rhetorical way. It was clear they all knew she's done this many times.

"Three." He reluctantly admitted.

"Don't you use condoms?" I asked. The alcohol was getting to my head a little, I was not expecting to be openly talking about sex with a bunch of dudes on this trip.

"Yes, but she still freaks out. She texted me an hour ago that she just got her period. I swear, she's looking for something to be stressed about. It's almost nice not to have her on this trip." The group got a little quiet at that, it was clear Miles was getting drunk too. Hoping to distract Miles from realizing that his comment was basically an insult to his girlfriend, I jumped in. "Ok Miles, it's your turn to ask someone!"

"Alright, Rose. Truth or Dare?"

I was feeling pretty uninhibited at this point, and chose Dare.

"I dare you to light up that joint and take the first puff."

I looked over at Cole for permission. There was something in his gaze... it was like he was relishing me asking for permission, and relishing making me wait. After a few moments, he signaled me over. "Since our little Rose here said she can't smoke the whole thing anyway, I guess it's alright to light it up now and give her a little taste."

I had smoked a few times before, but not recently. Still, a joint was much easier for me to handle than a pipe. I lit it, inhaled probably a little too much, and blew it all in Miles' face.

"Now we both get to be high," I laughed. All thoughts of Miles' girlfriend's pregnancy scare disappeared with the sweet smell of marijuana. Despite that it was only a dare for me, the rest of the guys took a hit each before putting it out, to be smoked by the winner later. When all the coughing was done, I dared Nick to go to the bathroom, get hard, and send a dick pic to his fiancé, who was still stuck statewide, due to her fear of flying. Honestly, I was just trying to get him to take a shot, but to my surprise, he didn't back down. He said he missed her anyways. While he was gone, Charlie finally couldn't hold it any longer, and rushed to the ocean.

"Remember, you can't just pee off the side of the dock! You have to be submerged!" I yelled after him, giggling.

This left me alone between Miles and Cole.

"Damn, it's really too bad we didn't play strip poker, eh Cole?" He shot Cole a meaningful glance. It wasn't hard to interpret. I playfully nudged both of them.

Cole didn't answer Miles, but instead turned to me. "Rose, Truth or Dare?"

"Isn't it Nick's turn? And he isn't back yet."

"This is just for fun! Just for us. Come on."

Rising to the challenge, I chose Dare.

"I dare you to take off your top."

Miles hooted. "Now I see! Strip Truth or Dare is a genius idea."

"Dude, she's not going to do it," Cole said, looking me in the eye. "She's going to end up taking her first shot. The first shot of the game."

I wanted so badly to prove them wrong, and what the hell? We were in an honest to God paradise, I was drunk, high, and surrounded by super-hot guys. I know I've had fantasies about this very scenario. Cole may have even been featured in one or two of them. So in a moment of spontaneity, I pulled at the strings holding my bikini together and quickly ripped it off.

I was quite chesty, and my bikini had been supporting my breasts as much as covering them. My tits now bounced free, and I could tell the guys enjoyed it much more than they thought they would.

Miles and Cole both were whooping and definitely openly staring. "Cheers, Rose! I did not think you had the guts to do that." They each grabbed a shot and toasted me. "Quick, here comes Charlie, back from his little piss in the ocean. If you don't want him to see your tits, Rose, I'd suggest putting that back on."

I turned away, my cheeks slightly aflame, hoping Charlie didn't see my breasts, or worse, my nipples, which were hard, to my surprise. I quickly retied the back of my string bikini and slipped the top not over my head. I don't think he noticed; he was way too drunk.

"You were gone a long time buddy," Miles remarked good-naturedly.

"I haven't peed since we got in the pool! I had like a gallon inside me!" Charlie shot back.

We all laughed.

A few minutes later, Nick walks back, his boner startlingly obvious in his swim trunks.

"Whoa dude, you didn't want to wait a few minutes? The Dare wasn't to show us your boner," Charlie laughed.

"Nah, who gives a fuck, huh?" Smiling, he slid back into the hot tub. "We'll see what she sends back later."

"Oh we will?" Miles asked, an implication in his words.

"Go to hell, Miles, I'm not showing you shit!"

Miles grinned. "It's fine, I suppose I may have got my fair share of titties already today."

Before Nick could ask what that meant, I yelled, "Nick it's your turn!"

"I dare Rose to take her top off," he said, not missing a beat.

"Hey!" I had no way of knowing if it was a coincidence or if he knew I had just taken my top off five minutes earlier, but it was eerie. "You didn't give me a chance to even choose Dare! So now I'm choosing Truth."

He grinned. "So... truthfully... will you tell us why you won't take your top off?" He laughed. Exasperated but high on booze, weed, and life, and I was enjoying all the attention. I hadn't had this much male attention in a while, and I felt like the hottest girl there. I had certainly noticed a few other women giving me some envious glances here and there. Clearly, they didn't know I was just here with friends. But still, it was fun to bask in it.

"We're all topless Rose, come on!" Charlie chimed in.

"We're in public!" I responded.

"So, is that your answer? The reason you won't take your top off is because we're in public?" That can easily be remedied, Rose. We all have a block of rooms in that building right over there." He nodded toward the beautiful exterior of our luxury rooms, where you can swim right up to the back door to your room.

"Come on guys, it's getting late, let's continue this tomorrow?" Cole asked. Since he had already seen me topless moments before, he was less invested in this Dare.

"Fine," Nick agreed amicably. "But we're picking up right where we left off tomorrow!" He winked.

"Only after a few drinks, Nick!" I winked back.

Instead of swimming up to the rooms, I walked back to the dry side to pick up my bags and other things. Cole joined me; his backpack was on the dry side as well.

"You look like you could use a hand back," he said.

He was right. I hadn't stood up in a while and now that I was, I was swaying a bit. I didn't want a repeat of the hot tub. "Sure, thanks."

We walked a few minutes, it was longer this way, but we were dry. "So why didn't Melina join you?" I asked. Melina was Cole's new girlfriend.

He took a sip of the drink still in his hand. Something fruity and delicious, it looked like another Sex on the Beach.