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Tarot Series: The Fool

The Fool Keywords: Beginnings, innocence, spontaneity, a free spirit

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JS Lane
Jul 23, 2026
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A tarot card, The Fool specifically, convinced Madeline to go to Jamaica on her own, assuring her that all adventure required a little risk. Strictly speaking Maddy wasn’t generally swayed by tarot or other forms of what she thought of as ‘woo-woo spiritual stuff’. But something felt different about the reading she received totally by chance in the mall one afternoon. This feeling was how Maddy found herself sitting at a bar sipping a Pina Colada waiting out a rainstorm that had rolled in.

It was her first day in Jamaica; having arrived that morning, she had taken a nap to shake off any jet lag. Upon waking, feeling slightly refreshed, she changed her clothes and ventured out to the beach. Mere moments later rain clouds had rolled in and unleashed a sudden storm. The bartender assured her it would be short lived.

A few minutes later he was proven correct as the Caribbean Sea glinted in the bright sunshine. Maddy squinted out towards the water, sliding her sunglasses over her eyes. The waves crashed, loud enough that she could hear the roar of them from her stool at the bar.

She wondered, for what seemed like the thousandth time, if this trip had been a mistake. Perhaps it was too much, too far, too soon. However, the time passing on the calendar and her friends’ encouragement told her it was not.

Maddy hadn’t been on a vacation in over a year. Not since that last trip with Irene, just before her death, which still felt so near. Her throat tightened painfully, and she sipped at her Pina Colada trying to ice the ache away.

“Can I take this to the pool?” she asked the bartender.

“Of course! Enjoy your pool time!” the bartender replied.

She smiled and thanked him before sliding off her seat. She readjusted her sarong, which she had twisted around her hips like a skirt. Although clothing was optional at the resort, she wore a two-piece bathing suit, her hair tied up and tucked under a sun hat. She grabbed her small beach bag which held a book, along with her water bottle and sunscreen. She took another sip of her half-finished drink and walked to the pool.

It was late afternoon, that strange in between time after lunch and before dinner. She was hungry but felt it was too early to take in anything of substance. There was a decent sized crowd at the pool, lounging on chaises, wading in the pool or sitting at the swim up bar. People wandered around in various states of dress. Some were totally nude walking around confidently, a few topless or bottomless, others adorned with sheer garments that covered nothing at all. The one uniformity was that most everyone wore some type of footwear to protect their feet from the concrete surrounding the pool.

Maddy tried not to stare as she procured a towel from a straw covered hut where a smiling woman sat noting room numbers. After readjusting her sunglasses, she searched for an empty lounger with ample shade to protect her pale skin. As much as she enjoyed the sun, her Celtic heritage meant she burned very easily. As soon as she claimed a lounger and spread her towel a devastatingly handsome, dark-skinned man walked up to her. He wore the khaki pants and polo shirt uniform of the waitstaff here.

“Can I bring you another drink? Or something to eat, ma’am?” His voice was deep and carried the melodious accent of the island.

“Oh, um, I haven’t really looked yet,” she admitted grabbing the small plastic stand that showed their menu offerings. Her stomach growled at the choice of snacks.

“No rush, please,” the man said with a wide grin. Maddy returned his smile feeling a glow rise to her cheeks as she scanned the small menu.

“How about some French fries and an Aperol Spritz?” Maddy said quickly.

“Of course,” the man replied with an easy nod, not bothering to write anything down and left.

Maddy took in the sights while sipping the last of her Pina Colada hurriedly, rushing to finish it before her Spritz arrived. Most people were paired up or in groups but there were a few lone solo travelers floating around. Two men kept drawing her eye, not only because they were quite attractive, but also because they continually glanced her way.

They lingered at the shallow end of the pool. One clad in a small yellow Speedo stood swaying in the water, sipping a beer. The other, naked, leaned against the wall of the pool, a sweating wine glass in his hand.

As Maddy glanced at the two handsome men again, she spied her waiter walking past them. The nude man got his attention and the waiter leaned down listening to what he said. The waiter nodded, pulled a pen from his shirt pocket quickly and jotted something on his notepad, then continued his journey back to Maddy.

“Here you are ma’am.” The waiter handed Maddy her Aperol Spritz and placed a plate of steaming French fries on the small table next to her. He put down a plastic bottle of ketchup and pulled a small stack of napkins from his apron. “The gentlemen in the pool would like to put your order on their room.”

“Oh!” Maddy exclaimed, glancing at the men. “I don’t… I mean, I don’t know them or anything.” The waiter smiled.

“I thought you might not.” He sat down on the empty lounger next to Maddy. “I think you’re new to this.”

Maddy’s face reddened but she nodded. She gulped down the rest of her frozen beverage quickly.

“Well, this type of thing will happen here. You do not owe them anything. They thought you were attractive and wanted to cover your order.” Maddy bit her lip.

“What’s your name?” Maddy asked abruptly.

“D’Angelo, ma’am,” he said.

“D’Angelo, I’m Maddy.” She paused. “What’s usually done in these situations?”

“Generally, ma’am,” D’Angelo started.

“Maddy, please,” she said with a smile, which D’Angelo readily returned.

“Maddy. Generally, if you are interested in talking to them you can wave them over or go to them. If you are not, you can simply nod and smile. Maybe raise your glass in toast. That is the general etiquette here.”

“If I…don’t invite them over, will they be… well, will they harass me for the rest of my stay?” Maddy asked.

D’Angelo chuckled and shook his head quickly.

“No, they won’t. These two have been visiting here for years. They are very respectful and kind,” D’Angelo said.

“Alright, well, thank you,” she said and smiled.

“Of course! I’ll be back to check on you in a little while,” D’Angelo said. “Can I take your glass?” He gestured to her empty drink cup. She nodded quickly holding it up to him. After he placed it on his tray, he departed to attend to other guests.

Maddy sipped her Spritz, then turned her gaze to the men. They were watching her, each with a small smile on their faces. She lifted her glass towards them, and they returned the gesture then sipped. She chewed the corner of her lip for a moment, thinking as she watched them. Would it be so bad to invite them over? She glanced down at her book as her mind flicked back to what she now thought of as her tarot card, her Fool. What would The Fool do, she wondered. A small grin spread over her lips as she contemplated the question, already knowing the answer.

The men had gone back to their conversation but when she gave a small wave they looked over. She timidly motioned them over. The two men looked at each other, then waded to the steps where they climbed out of the pool. They toweled off a little before making their way to Maddy’s lounger.

“Hi,” said Mr. Yellow Speedo as he walked up.

“Hello,” Maddy replied, a small tremor in her voice she hoped they hadn’t noticed.

“Do you mind if we sit down?” the nude man asked.

“Please do,” Maddy said gesturing to the empty lounger beside her.

The men tossed down their towels and sat on the lounger. Maddy was grateful for her mirrored sunglasses as her gaze darted down to the men’s laps. It was embarrassingly difficult to ignore the member hanging between the nude man’s legs. Especially while Mr. Yellow Speedo was sporting a generous bulge in his wet swimwear.

“I’m Patrick, Tricky,” the nude man said holding out hand.

“Tricky?” Maddy asked. He smiled and nodded. “I’m Maddy.”

“Maddy, I’m Robert. You can call me Bobby.” Mr. Yellow Speedo took a turn shaking her hand.

“Thank you for…” she held up her drink.

“Of course! I hope you enjoy it!” Tricky said, sipping his drink from his glass.

“Please, help yourself to some fries,” Maddy said. She turned in her chair and grabbed one.

“Thanks,” Bobby said popping one in his mouth. “Oh! They’re hot.”

“Careful, hon,” Tricky said trailing his fingers over Bobby’s shoulders. He turned back to Maddy. “Is this your first time here?”

“It is,” she admitted.

She sipped her Aperol spritz and was surprised by how much was already gone from the glass. Her head was beginning to spin a little. She grabbed another fry and ate it, then pulled her water bottle from her bag and took a swig. “Um, D’Angelo said you two have been here a few times?”

“Oh yes, we try to come yearly. Jamaica is one of our favorite getaways,” Tricky said.

“It’s really lovely,” she replied.

“First time at a clothing optional resort?” Bobby asked.

“Oh, uh yeah,” Maddy said with a slightly hysterical titter. “First time for a few things actually.”

“Really?” Tricky asked. “Care to share?”

“Oh, uhm…” Maddy paused. She took another large sip of her drink. Suddenly D’Angelo was behind her.

“Another Aperol Spritz Maddy?” he asked.

“Well, I dunno,” she said. “The first one sort of went to my head.”

“Oh, go on!” Bobby said. “We’ll get your second round too. One more for us as well D’Angelo.”

“Please!” Maddy said quickly. “Let me get the second round!” Tricky smiled at her.

“If you insist,” he said with a wink. A hot blush rose to her cheeks.

“One more,” she smiled up at D’Angelo. The drinks did make for a good social lubricant.

“You were saying,” Bobby prompted when D’Angelo had left.

“Oh,” Maddy sighed a little. “I’m sorry it’s a bit of a downer. This is my first vacation on my own.” She grabbed a fry as tears pricked her eyes. Social lubricant and emotional dam breaker she thought of the drinks.

“My wife…passed about a year and half ago; cancer,” Maddy finished.

The two men looked stricken, their merry, slightly teasing smiles melted away to frowns.

“Jesus I’m so sorry,” Tricky said. “I didn’t mean to pry.”

“It’s fine, it’s fine,” Maddy insisted, wiping tears before they escaped her sunglasses. “It’s sort of silly, but I got a tarot reading, just a one card draw in the mall of all places. I got The Fool, which apparently means it’s time for new adventures so here I am.”

Bobby put a hand to his heart.

“I’m truly sorry for your loss,” he said. “How long were you married?”

“We had just celebrated 20 years,” Maddy said. “We’d been together five years before that, dating, living together.”

“Oh. My god,” Tricky grabbed Bobby’s hand and squeezed it. “We just celebrated 20 years together.” Maddy glanced down at their hands. “Oh, we’re not ‘officially’ married. Bobby doesn’t believe in marriage so we’re just…together. But we still celebrate each other, our relationship.”

“That’s lovely, truly,” Maddy said.

“So, you’re here on your own?” Bobby asked.

“I am. First vacation I ever planned. I was a bit of a passenger princess,” Maddy said with a slight chuckle.

“When did you arrive?” Tricky asked, sipping his drink.

“This morning,” Maddy said.

“Are you serious? This is fucking fate Bobby. Fucking fate!” Tricky said, whapping the back of his hand enthusiastically to Bobby’s shoulder.

“Calm down, Tricks,” Bobby said with a small smile, grabbing his hand and kissing the back.

“What? What’s fate?” Maddy asked.

“We arrived this morning!” Tricky said. “I noticed you right away when you came to the pool. You were too hot to ignore.”

“Oh!” Maddy blushed and adjusted her hat. “I’m not even topless.” Tricky waved his hand dismissively.

“There’s more to attraction than simply seeing some naked tits!” Tricky said loudly, before sipping his drink again.

“Seriously Tricks you need to bring it down a few notches,” Bobby said reaching for his drink. “This is what you get for drinking champagne in a wine glass.”

“That’s champagne?” Maddy asked.

“It is!” Tricky said holding his glass out of Bobby’s reach and taking another hearty sip. Bobby laughed and tried again to grab his glass.

“You two settle down,” D’Angelo said good naturedly as he brought their second round of drinks. “Or I’ll have to take your drinks back to the bar.”

“You wouldn’t dare!” Tricky said, then downed the rest of his champagne quickly.

“Don’t test me,” D’Angelo said with a cheeky wink. “Here you are Maddy.” He handed her a wine glass.

“Thank you!” Maddy said.

After D’Angelo left with their empty glasses Tricky turned his attention back to Maddy.

“Will you join us for dinner tonight?” he asked.

“Uhm,” she looked at Bobby.

“No pressure. It would be nice to have some extra company,” Bobby said with a smile.

What would The Fool do? Maddy asked herself again. She stifled the urge to stay holed up in her hotel room, alone, with too much room service and a mini bar.

“I would love to,” Maddy said.

~~

Tricky and Bobby asked Maddy to meet them at the restaurant that night. She was relieved that they didn’t ask to meet her at her room. She was up for adventures and understood the risk but wasn’t quite ready to give her room number out to strangers, no matter how kind or handsome they were. Just because she was following The Fool’s advice didn’t mean she needed to be overly reckless.

She chose a soft sundress to wear, laced up her back, with skinny straps over her shoulders. The hem line was short in the front, growing longer in the back making the dress feel elegant and much fancier than it actually was. She elected to go braless, since the tiny straps wouldn’t hide the undergarment and she didn’t even own a strapless bra. She wasn’t overly endowed in the breast area in any case.

Her stomach growled as she applied a little bit of makeup. She, Tricky and Bobby had finished off all the French fries, but shared between the three of them, they barely counted as a snack. When she had returned to her room a slight throb had begun to grow at her temple. Typical after three afternoon drinks with very little food or water. She drank a large glass of water along with a hydration supplement to take the edge off her tipsiness. To combat the slight ache in her head she took a couple of pills with her second glass of water, which she drank more slowly.

It wasn’t long before it was time to meet her new friends at the restaurant. Tricky and Bobby stood outside the restaurant looking dapper in their casual elegant clothing. She suddenly realized in all their conversation by the pool she had never asked what either of them do for work.

A wave of shame washed through her at her self-centeredness. The two men had been the ones asking question after question. Still, she thought she could have thrown in a “how about you?” or something at the end of nearly any of her replies. Nevertheless, both men smiled as she walked up.

“Maddy! You look amazing!” Bobby said.

“Oh, thank you!” she replied a slight blush rising to her cheeks.

It had been a very long time since she had felt attraction to a man. Regardless of her marriage to Irene she had clung to her bisexual label with an iron grip. It had been one of the few things that annoyed Irene, how often she would correct people when they referred to her as a lesbian. Maddy always pointed out that Irene would do the same thing if people automatically assumed she was bi.

“Shall we go inside? Our reservation is in a few minutes,” Tricky said holding out his arm for Maddy to take.

“Certainly,” Maddy said as she slid her arm through his.

Bobby crooked his arm in similar fashion and Maddy let out a little giggle as she slipped her other arm through his.

They checked in at the hostess podium and were taken to their table immediately. It sat out on the balcony in the warm night air, overlooking the darkly sparkling ocean. The moon was bright and full, fat clouds rolling across it now and then. The water reflected it brightly on the rippled surface of the gently rolling waves making it look as though there were two skies, one above and one below.

“What a gorgeous night,” Maddy said with a wistful sigh.

“It really is,” Tricky agreed.

Their waiter came by and took their drink order, bustling off once more while they perused the menu. After deciding on what to eat Maddy put her menu down.

“You know I was feeling a little guilty after this afternoon,” she began. “I realize I didn’t ask anything about you two.”

“Bobby told me I was asking too many questions,” Tricky said with a smile. “That’ll happen after a couple wineglasses of champagne.” Maddy laughed lightly, her hand falling to Tricky’s arm for a moment.

“I hope you weren’t put off. Although, we’re all together now so I guess I’ve got a second chance,” Maddy said. Her hand still rested on Tricky’s arm, and her mind flashed briefly to his penis, which she’d had plenty of time to steal glances at this afternoon.

“Not at all!” Bobby said. He leaned a little closer to Maddy. “It was nice to get to know you. We’ve got all week to talk about ourselves.” He gave her a little wink, and she blushed deeply.

“Well, what do you two do?” Maddy asked.

“I’m an influencer,” Tricky said with a roguish smile. Bobby rolled his eyes, but his smirk gave away his delight.

“I’ve just got a boring office job that I’ve had since college,” Bobby said. “Tricks is the main breadwinner. He makes more in his influencing than I do at the office.”

“Really?” Maddy said. “That’s fascinating. I didn’t realize there was so much money in influencing.”

“Well, there’s not really,” Tricky said. “I supplement it with other things.”

“Other things?” Maddy asked.

Tricky raised his eyebrows and smiled a little. “Think Only Fans, Feet Finder, that type of thing.”

“Oh!” Maddy exclaimed. “Well, this just got even more fascinating!”

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