No Room at the Cabana Ch. 02

Story Info
Another day of adventures in uninhibited Key West.
6.9k words
4.7
19.1k
8
0

Part 2 of the 3 part series

Updated 06/08/2023
Created 05/25/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

(Author's note: this is part two of a continuous story. It will make the most sense if you read Chapter 1 first.)

: : : : :

H O L L Y : : : We spent Saturday morning sight-seeing. After a late lunch, we found ourselves back at the pool. Taking off my clothes in front of other people still made my head spin, but I wasn't nearly as uncomfortable as yesterday.

There were several couples there that we hadn't already met. They were very friendly, and very naked. The guys were not too hard on the eyes, mine and Shannon's at least, and our guys seemed to find their ladies quite lovely too.

One of the guys asked if we liked live music, and Shannon said it depends on what kind of music, and how good the band is. He said there was a club nearby that always had great bands. They had two shows today -- the main band for the evening he had never heard of, but there was a matinee set that featured a blues singer he had seen before and liked.

J A S O N : : : His wife said she wasn't particularly a blues fan, but it was the type of blues she liked -- up-tempo and energetic, not the slow, weepy kind, and the singer and his band were great. Their set started in about forty-five minutes, and they invited us to join them there.

It sounded like fun. They went to their room to dress, and we gathered our stuff to head to ours. Right then Cait, Dani, Jessi, and Ally arrived, as uninhibited as ever. They wore tiny bikinis, but shed them as quickly as they could. Cait and Dani did anyway, with Jessi and Ally not too far behind.

They were disappointed we were heading in. I told them about the blues matinee and invited them to join us, but they had just arrived at the pool, and although Dani said maybe they'd join us later, it wasn't very convincing.

They asked if we were going to the club later, and I said, "Probably not. Been there, done that, y'know? Are you?"

Dani said, "Definitely. I mean, when are you ever gonna find another place like that?"

Mark said, "Good point. Maybe we'll see you there."

He sounded about as sincere as Dani had about the blues.

: : : : :

S H A N N O N : : : The blues singer was fantastic, although the matinee -- the club called it a "sound check" -- was only a single one-hour set. He was selling a CD, and we each bought a copy -- it turned out to be excellent.

We had dinner at another place the Australian lady suggested. The food was great, the atmosphere relaxing, and the service attentive. The meal was served in multiple courses, with no rush whatsoever. With appetizers and after-dinner drinks, it was after 11:00 when we left.

Walking back to the guest house, Holly said, "What do you think, hot tub and wine?"

Jason said, "I keep thinking about what Dani said, about when will we ever find another naked dance club? What do you think of going back?"

I didn't want to appear too eager, but I had been thinking about Dani's comment and was feeling drawn to the club, too. Holly said, "Shannon, I'm sure the guys would love to see us dance naked again, but how about you?"

I only paused a second, and said, "Let's do it."

M A R K: When we got to the top of the stairs, we didn't have to wonder if there'd actually be naked people there -- on the second stool, right as we emerged from the stairwell, was a completely naked guy. Same position as yesterday, but a different guy. I said, "Interesting, I wonder if they're employees, or maybe locals who they give free drinks in order to 'set the mood' for the rest of us."

It was later than we had arrived yesterday, and the club was more alive -- plenty of topless and naked people. Cait and the others were already there, naked, of course.

We found an empty spot by a table, and I took off my shirt and shorts. Holly grinned at me and said, "Ooh, aren't you the daring one?" I pulled off my boxer briefs and said, "When in Rome, babe."

She nodded and held her hands up in the air. I pulled her dress over her head, and was startled to find bare titties under it -- I can't believe I hadn't already noticed she was braless. I returned her "Ooh, aren't you the daring one?" comment. She glanced around the club, confirmed that there were several naked ladies already, and with only a trace of hesitation, peeled off her panties. No angst or drama today -- it's amazing what a difference 24 hours can make.

Jason, already naked, was lifting Shannon's dress over her head. She also didn't have on a bra. She dropped her panties, and Jason headed to the bar to get our first round. We hit the dance floor, and I realized I was glad we came back. From the energy of their dancing and the looks on their faces, the others were too.

J A S O N : : : An older guy, completely naked, walked up and applauded us. It was a very odd moment, to say the least. I was afraid he was some sort of loony toon, but he turned out to be a gem. He was a motivator, an instigator. "Thank you," he said, more to Shannon and Holly than Mark and me, "for being brave enough to take off your clothes." He gestured at a cluster of clothed people and said, "There are so many fraidy-cats here tonight. And it's such a lovely night to be naked!" With that, he moved on.

He didn't seem to be a dancer, but he was constantly in motion, walking around the edges of the dance floor. He'd stop and interact with anyone who was receptive. He offered encouragement to those who needed it, and gently goaded those who seemed to need that. "You haven't really been here if you don't take your clothes off," he'd say to those fully dressed. "It's only difficult the first time," he'd say to someone who looked like they were having trouble getting a key piece of clothing off. Cait and her friends seemed to know him -- they called him "cheerleader guy."

H O L L Y : : : When we first encountered him, I wasn't sure if his elevator quite reached the top floor. But he turned out to be priceless -- he not only encouraged people, he chastised people who needed it. I saw him approach a group of five or six guys who had arrived together. They didn't buy drinks, they didn't even take off their shirts, they just settled on the side and blatantly gawked at the naked girls -- very creepy.

"It's amazing," he said to them.

"Huh?" one of them responded. "What is?"

"The more guys who leave their clothes on," and he glared at them, "the fewer girls take their clothes off." Then he walked away.

Barely a minute later, they left -- I think he made them realize they weren't invisible.

J A S O N : : : When we compared stories later, it turned out we had each noticed cheerleader guy doing something extraordinary.

I was standing at the bar, waiting to order our next round of drinks, and I saw him talking to a girl who wore a simple, but elegant, ankle-length dress. It would be easy to lift over her head, and I had seen her pull the hem up to mid-thigh several times, like she was going to take it off, but she never did.

He said to her, "I thought you were going to go for it, but I guess I was wrong."

Grinning coyly, she said, "What do you mean, 'go for it'?"

"You know, what people do here."

"Dance?" she asked, laughing.

"The other thing people do here."

"Drink?"

Now he laughed, and rather than press her further, he walked away. That impressed me -- saying much more would have been too much.

The next time I saw her, she still had her dress on, but she had stopped dancing, and was staring intently at him. I couldn't tell if the guy she had been dancing with was her boyfriend, her date, or a stranger. Whoever he was, she had him completely tuned out.

She made eye contact with cheerleader guy and held his gaze. She gripped her dress at the waist and began raising it, hoisting the hem up from her feet. Slowly, inch by inch, she gathered it into her hands, while she bored holes in his eyes with hers. She pulled the entire length up to her waist, revealing a tiny pair of lace panties.

She continued lifting, revealing her tummy, eyes still locked on cheerleader guy. She kept lifting, and her boobs popped free, unencumbered by a bra. She only broke eye contact for a moment to lift the dress over her head.

Cheerleader guy applauded her, and yelled "Bravo." She glowed, and dipped her eyes. I thought that was about the sexiest thing I'd ever seen, but I was wrong -- they weren't done.

When she looked back up, he pointed at her panties. He wiggled his finger from side to side, tracing an imaginary path down her leg -- ingenious: "Take them off" in a single gesture.

She shook her head, "No."

He repeated the gesture, with both hands this time, and nodded, "Yes."

She pierced his eyes with hers, and hooked her thumbs in the waist of her panties. Almost imperceptibly, she began to lower them. Glaciers move faster; her eyes and his stayed locked.

When she finally reached her mound, she revealed a rich thatch of short curly hair. She had trimmed the sides, so it wouldn't leak out of her bikini, and rounded the upper corners, but as she lowered her panties, a fairly wide triangle emerged. When she got near the bottom, though, her bush ended -- she had shaved the area around her slit. It peeked out from behind the lace, then was completely uncovered. When she got her panties below her crotch and the elastic no longer gripped, she let go, letting them fall to the dance floor. She stood stock still, letting the warm tropical air -- and everyone's eyeballs -- waft over all her private parts, and letting cheerleader guy absorb her complete nudity at his leisure.

He broke the spell and took a step toward her, offering her a high five. Rather than slapping his hand, she grabbed it and tugged him closer. She pulled his neck down, and gave him an amazingly delicate kiss on the cheek. "Good job," he said as she released him. She stashed her clothes on the side and returned to her guy -- I wonder what he was thinking -- and resumed dancing, as if nothing had changed. That's the sexiest thing I've ever seen. Cheerleader guy, indeed.

M A R K : : : Shannon and Holly were taking a break from the dance floor, so Jason and I were dancing with Dani and Jessi. Right next to us was a couple, approximately my age. She was dancing in only her panties, even though he still had on his shirt, shorts, shoes, everything. She was pretty -- maybe not in a league with Cait and her friends or Shannon and Holly, but she had a good figure and a lovely face. Her boobs were nice, pert, medium-sized, and her ass was firm, framed nicely by her panties, which weren't a thong but didn't cover much of her cheeks. He wasn't exactly chubby, but let's just say he obviously wasn't a runner -- he seemed to have an extra roll or two around his middle. He had been working on getting her panties off for five or ten minutes, but she wasn't going for it.

Right as cheerleader guy walked past us, still-dressed guy lost his patience, and reached over to yank her panties down himself. She held them in place, and barked, "Quit it!" Cheerleader guy saw the whole thing.

He said, "Dude, help her out, at least take your shirt off!"

The guy looked at him like he had missed something painfully obvious. He gestured at his own torso, and retorted, "You don't understand, my boobs are bigger than hers."

Jessi whispered, "Awkward!" and we all laughed.

Now, it was obvious to me that the guy wasn't trying to insult his lady. He was being derogatory about himself, to explain why he kept himself covered. But that's not what a lady would hear, at least any that I know.

Cheerleader guy suppressed a chuckle, and looked at the guy, incredulous. "You're from out of town, right?"

The guy looked at him like, "what does that have to do with anything?" and said, "Yeah, why?"

"Your hotel room -- does it have a couch?"

"I don't know. I guess so. Why?"

Cheerleader guy glanced over at the entrance, where the lady, with all her clothes back on, was disappearing down the stairs. "Because I'm pretty sure that's where you're sleeping."

"SHIT!" the guy yelled, and ran after her. "Madison, wait!"

We all laughed as he disappeared. Jessi said, "We should take up a collection, buy him a clue..."

H O L L Y : : : I was standing at the side, sipping my drink. Cheerleader guy was next to me, and a young couple was next to him, looking more nervous than anyone I had seen there. Obviously they wanted to take their clothes off, but were finding it impossible to get started. They were both medium height, slender, very attractive, and very young -- they looked barely drinking age. He wore a shirt and shorts, she had on one of those strapless dresses that is tight stretchy fabric from the waist up. Its texture was so coarse I couldn't tell if she had on a strapless bra or not. Her boobs weren't large, but she was so petite, they stood tall and proud from her chest -- perfect for her size. Cheerleader guy noticed their nervousness and asked them, "First time here?"

They nodded. "It's our honeymoon," the girl said.

Cheerleader held his cup up to them in a toast and said, "Congratulations." They smiled and nodded their thanks. "You found the best spot in town for a great evening."

"What's it like?" the guy asked, too nervous to even say the word "naked."

Cheerleader guy paused, and said, "Some people like it, some don't. Obviously," and he gestured at his own body, "I like it. A lot. Are you gonna go for it?"

"I don't know," he answered, his voice almost a whisper. "We've been talking about it."

Cheerleader guy waited several minutes, and I hoped he wasn't going to use one of his usual litany of one-liners, "It's only difficult the first time" and such, which I didn't think would work on them -- they were too tense. He surprised me, saying, "The great thing is, you don't have to do it all at once." He gestured at two couples who were dancing in their underwear, one of the girls in her bra, one topless. At the sight of the topless girl, honeymoon girl gulped.

Cheerleader guy paused again, and said to the guy, "This is one time where it's gentlemanly NOT to let the lady go first." The girl looked deeply relieved, but the guy looked utterly panicked. Cheerleader guy repeated, "You don't have to do it all at once." Seeing the guy look somewhat relieved, he walked away to take one of his laps around the floor, leaving the couple to contemplate what they were going to do. They clearly didn't want to leave without overcoming their inhibitions, but the reality of undressing was proving to be far more difficult than they imagined.

They stared straight ahead, each grappling with their own shyness, complicated by not wanting to disappoint each other. He stood straight, steeled himself to action, and unbuttoned his shirt. He slipped it off his shoulders, and handed it to her. She folded it, and placed it on an empty space near our pile. She gazed at him admiringly, and he stared straight ahead, a pleased smile crossing his face.

They worked on their drinks for several minutes, finishing them. He set off in the direction of the bar, but came right back. She looked at him questioningly. He got some money out of his shorts, unzipped them, and stepped out of them. He handed them to her, and set off toward the bar in his briefs, which were low-rise, a deep red. She watched him disappear into the crowd, her face a mixture of admiration of his bravery, and panic that it was nearing her turn to take something off.

I resumed dancing, and lost track of them. I don't know if it was fifteen minutes, or maybe half an hour later, Jason and I were dancing with a couple of the girls, and I noticed honeymoon couple dancing near us. She hadn't taken anything off, but at least was experimenting a bit. She lifted the hem of her dress several times, bunching it in her hands, but always stopping short of exposing her panties. I was beginning to think she wasn't going to find the courage to take anything off before the evening was over. Cheerleader guy passed, and they flagged him down. The girl said, sounding rather desperate, "There are so many people here..."

Cheerleader guy looked around, and nodded. He gestured at a couple of girls dancing nearby as they pulled their dresses off, revealing tiny thongs and no bras. He said, "Check it out, though, I don't see anyone who even noticed. Definitely no one is gawking at them." The couple looked closely at the girls he pointed out, and honeymoon girl especially looked around to confirm that what he said, that no one was ogling them, was true. She nodded at cheerleader guy, and he wandered off.

The girl nodded and asked her guy, "Are you sure you're sure?" He nodded. She pulled the hem of her dress up to her waist. Her panties were sweet, tiny things, sky blue satin with dark blue elastic edges. They danced on, while she nervously checked to see if anyone was watching -- as cheerleader guy said, a person or two may have glanced their way, but nobody stared.

She visibly took a deep breath, dropped her hem, hooked her thumbs in the elastic under her arms, and started lowering her dress. The stretchy part hung on her nipples, which were hyper-extended. They popped free, and she visibly gulped. She danced like that for a few minutes, the top part of her dress bunched around her waist, her sweet little titties out. When her world didn't implode, and the current song ended (I bet that will be her "topless" song forever), she lowered the dress past her hips, stepped out of it, stashed it on their pile, and finished her drink.

She sent him to the bar for more drinks. While she waited, she was so nervous she actually wrung her hands. Her hands kept spontaneously covering her breasts, then she'd catch herself and force them down to her sides. When he returned, she held her drink against her forehead, took a huge sip, set it down, and led him back onto the dance floor, near us again. Their dancing gained energy as they adapted to being without their clothes. Three or four songs later, she stopped dancing in mid-song, pulled his head forward, and whispered into his ear. He nodded, and held stock still. She knelt in front of him.

She grasped the waist of his briefs and slowly slid them down his legs to the floor. He stepped out of them, grinning, and she stood, looking rather grim. They gazed into each other's eyes, oblivious to the world around them. She nodded, almost imperceptibly. He knelt in front of her and slowly, gently pulled her panties down and off. He stood, and hugged her tightly, shielding her front from the crowd. He waited for her to end the hug, and stashed their underwear. They resumed dancing, both of their faces with uncontrollably huge smiles.

They channeled the energy from their nervousness into their dancing. The next time cheerleader guy passed, he didn't have to give them high fives, they gave them to him. He had said all the right things to them at exactly the right times, giving them an evening of adventure that, without him, they would have missed. They were still there, dancing vigorously, when we left. I can only imagine the ferocity of their love-making when they got back to their room.

S H A N N O N : : : A bachelorette party arrived, six or seven girls. The bride -- we knew that because she wore a beauty-pageant-type sash that said "bride" -- was a short blonde, slightly stocky, but very pretty. Her friends, though, were all stunning. Jason and Mark couldn't take their eyes off them. The thing was, they didn't seem inclined to get undressed. A couple of them shed an outer layer, but that still left them in proper street garments, not even any underwear showing.

Cheerleader guy went to work on them, dropping all sorts of hints, encouragements, and challenges. After almost an hour, he got the prettiest one, a tall slender brunette, to take her dress off. Over the next few minutes, the others did the same, although they kept their panties and bras on. They danced near us, continually glaring at us and anyone else who wore less than they did.

12