Author’s Note:
This story explores gender roles–who should be the ‘Alpha partner’ in a relationship? Unfortunately, the ‘Golden Rule’ usually means the person with the gold makes the rules.
All the characters in this story are over eighteen years of age.
_____
Cassie Blackstock peered into her ensuite mirror, carefully examining her smooth unblemished complexion and the curves of her naked body. She was bone tired and utterly burned out. It had been a month since her last decent night’s sleep; even her eyes ached. And it showed.
Frowning, she leaned closer to the mirror. In the bright white light of her marble-walled bathroom, she could see dark smudges under her eyes and a hint of swelling. Even her body looked tired and gaunt after months of sixteen-hour days and skipped lunches. She was still pleased with her breasts, which nicely bore their own weight, proudly upright with large dusky pink nipples poised at the upper tips. But she could clearly see each individual rib protruding under the taut skin of her torso. Her pelvic bones were more prominent than ever before. She seldom permitted herself to get this run down and knew she had to do something about it soon.
Being the youngest and possibly only self-made female billionaire in Canada, provided a lot of perks. Her eleven-thousand square foot, fifteen million-dollar penthouse in Vancouver’s downtown core, was the entire top floor of her new sixty-five story, concrete and mirrored-glass office tower. A chauffeured limo was at her disposal at any time of the day or night. Her business offices on the sixty-forth floor and her penthouse were connected via a private elevator. A second private elevator would transport her to the lobby or parking garage in less than a minute. Her Bombardier Global 7000 commuter jet was stored in a private hanger, seven miles south at the Vancouver International Airport. She did not own a helicopter but contracted with a local company to have one on standby. From the helipad on her building’s roof, she could be transported to her hanger in ten minutes. During Vancouver’s crushing rush hour traffic, it might take hours to drive there.
Over the past few weeks, she had been experiencing the old familiar gnawing, deep in the core of her loins. Being single and a workaholic, there was little or no time for romance in Cassie’s life, and the biological need for a man’s body and the pleasure it could provide occasionally became overwhelming. This would have to be addressed soon, too. She knew from experience this primal longing would cause her disciplined concentration to falter. She had taken temporary action last night, but it wasn’t enough. She needed at least a week of rest with a man capable of meeting her needs.
Cassie would be the first to admit she was a loaner. The last surviving member of a dysfunctional family, she had no parents, grandparents, siblings, or even distant relatives to worry about. She worked such long hours she didn’t have time for close female friends. The other issue was trust–when you are one of the wealthiest people in your country, even your close friends can develop ulterior motives. That had happened to her many times; her assistant Wes was the only person in the world with whom she could truly relax.
Her vacation needs were basic; lots of good food and drink, a hot environment, a luxurious place to stay, perhaps some stimulating touristy activities unrelated to her business, and a man with the stamina to bed her two or three times per day or more if possible. Then she would return to work fully invigorated, healthy, and ready for anything the world might throw at her.
Today was going to be an intense, insanely busy day but with a bit of luck, she could escape tomorrow or certainly the next day. She’d call Wes and have him make tentative arrangements. She wasn’t sure where she’d go this time–it was early January and colder than a witch’s tit outside. So it would definitely be somewhere guaranteed to be sunny and hot.
Cassie had visited many of the most luxurious adult-themed resorts in the world. Maybe it was time to go back to her favorite in Costa Rica–the Pasión al Sol, or ‘passion in the sun’, as it translated to English. She’d vacationed there a half-dozen times before. They charged two thousand bucks per night for her favorite cabin, but the price included nearly anything that might occur to their well-heeled guests. Much of the resort was clothing-optional, so guests could enjoy their entire stay without ever dressing during the day if that’s what they liked. The temperature would likely not dip below eighty degrees, day or night.
Finally, the resort had its own airport so Cassie’s jet could fly there nonstop from Vancouver. Her new Bombardier Global 7000–flying near Mach 1–would have her there in five hours. She would sleep the entire way in the comfortable bed of her personal jet cabin. If she left at midnight and with the difference in time, she’d be there for breakfast in her favorite seaside cabin. She made up her mind–this is where she was going. A week at the Pasión al Sol would fix her right up–she’d be as good as new. She was looking forward to it already.
The only remaining question–what about a man? Would she take someone with her? Or perhaps call a friend to meet here there? She had a dozen lovers scattered around the globe who would drop everything and catch a flight there if she called. She had a few contacts within the resort, too. Sometimes she preferred to have a man stay with her; someone she knew and liked. It was therapeutic to talk with a confidant for several days, although there was much about her life she would never disclose to anyone. But other times, she preferred having several men over the course of her vacation; this ensured she would have a good deal of extremely lively sex, with a number of fresh, virile lovers.
She might also choose a local man; there were scores of handsome buff businessmen in Vancouver who would follow her anywhere at the snap of her fingers. Her mind wandered back, reminiscing about a few of them until she felt the spark of heat glowing even brighter and hotter, deep within her loins.
_____
The apartment was still utterly dark at 6:15 AM. November through February were her least favorite months–now in early January, it wouldn’t be fully light until 8:00 AM and nearly dark again by 4:30. She missed having bright sunlight on her wrap-around patio in the morning and running the Stanley Park seawall.
Now wearing only a string thong, the teabag-sized patch barely large enough to cover her labia, she padded down the hall to her private gymnasium and spent an hour working her body on a series of gleaming stainless steel exercise machines. Her lean frame glowed from the exertion–in the wall-to-wall floor-length mirrors, there was no trace of fat on her limbs or torso. As in her ensuite mirror, she could see her body was too thin–she needed to put on at least ten pounds. Her legs and arms rippled with perfectly toned muscle; her stomach was like a washboard. But she had her soft spots too; her lovely large breasts and small firm buttocks were classically shaped and drew admiring male and female scrutiny everywhere she went.
There was movement in the doorway behind her. In the mirrors she could see a tall, well-built sandy-haired man leaning against the door jamb, watching her carefully.
Jesus Christ, this one really is good looking, she thought. What the hell’s his name… Sam I think…?
Having just come from the shower, Sam Ballard had a thick plush bath towel wrapped around his waist and was clearly enjoying the view.
“Morning, sugar butt,” he said to her, smiling.
She returned a thin smile, admiring the sprinkling of blond curls across his chest and belly. His arms and legs were also lightly covered with fuzzy golden hair matching the curls on his head. He had not combed it yet, so it tumbled down over his forehead in a boyish fashion.
“You do this every morning, Cassie?”
The air was warm–she liked it around seventy-five degrees when working out naked, or in panties or a thong. She was just finishing a thirty-minute session on a step machine and her body gleamed in the overhead lights, covered with a light sheen of perspiration. Her bare breasts bobbed and swung rhythmically from side to side as her muscular legs pumped up and down on the machine’s peddles.
“Pretty much. How about you; do you work out?”
She really knew very little about him. Wes had run a quick security check, finding nothing exceptional in the Canadian or international databases. If he’d ever been charged with so much as a misdemeanor or especially some kind of sexual crime in any participating country, she’d know about it. She was amused to see a bump forming under his towel.
“I run the odd marathon and go to the ‘Y’ at least three times a week,” he said. “I also belong to a karate dojo in Seattle where I’ve earned a black belt. You think it’s working for me?”
He pulled his towel open and turned so she caught a quick flash of his naked body in profile. He had the muscles of a professional boxer or quarterback; not the ugly over-developed mass of a bodybuilder. He had the nicest ass she’d seen on a man in some time, too. He was definitely a good-looking son of a bitch. Cassie liked some body hair on a man, as long as his entire body wasn’t covered with coarse black hair that made him look like an ape. Sam’s near-white body hair, thick and curly over the tanned skin beneath, did not grow on his back and ass. She had liked the way it had tickled her nipples when they’d made love last night. She could feel her juices stirring and mentally went over her morning agenda, wondering if she could cancel her first appointment. She decided she couldn’t; if she got back in the sack with this guy, it might be an hour or two before she was ready to send him on his way.
Besides, he was a little on the arrogant side and he’d called her ‘sugar butt’ which had royally pissed her off.
He was from Seattle–a client’s lawyer sent to her firm to personally notarize a contract being signed by Cassie. There was so much money involved, neither party trusted an ‘off the street’ notary. The chemistry between them was instant and powerful. He knew her reputation; if she wanted to be with him, there would be no cutesy, romantic courting. He would go to her bed after their first date, or he’d never see her again. He’d heard of other men who’d dated her once but had been rejected in short order. He wondered if he could be the one to ensnare the legendary Cassie Blackstock.
They were both thinking about their session last night.
She’d invited him to dinner, so rather than flying back to Seattle, he’d met her that evening in an exclusive restaurant in the basement of her building. They were the only people there; the restaurant having closed an hour earlier. You didn’t walk out of this establishment after a dinner for two, without a bill approaching a thousand bucks–maybe more depending on drinks and wine. A shot of single malt scotch was eighty bucks for the good stuff. They sipped wine that sold for hundreds of dollars per bottle and ate Kobe beef, flown directly to the restaurant from Japan. The beef alone was two hundred per plate.
But she owned the restaurant and the entire building, so she didn’t give a shit what the bill came to. She just initialed the chit and left a hundred-dollar tip. No big deal.
She was a smart lady when it came to socializing, too. Now with her thirty-fifth birthday looming ominously on the horizon, she’d been with enough men to understand what gets their attention. They are visual bastards; seldom interested in a lady’s mind until thoroughly satisfied with her ass and lovemaking skills. Cassie was pretty damn spectacular in all departments.
She’d come down to the restaurant, straight from work on the sixty-forth floor–still dressed in her expensively tailored business suit, cut precisely for her body. The skirt was skin tight, fitting her slim form like a rolled-on condom. The material was extremely soft, requiring bra and slip during the day for business or her nipples and buttocks would be clearly outlined. She’d slipped off her blouse and bra before leaving her office, partly because she was more comfortable without them. Also, she wanted to see the lawyer’s reaction to three or four inches of swollen cleavage, peaking out between the lapels of her suit jacket.
It took him about two seconds to notice and he was impressed. First of all, that she’d done it, and second, at how magnificent her body looked in this otherwise formal business apparel. He began to anticipate seeing more of it before the evening was over. His wishes came true. She invited him upstairs for a nightcap and attacked him before he’d finished his first drink.
He was disappointed the next morning. After watching her working out on the step machine, her amazing breasts unrestrained and glossy with sweat and her buttocks utterly exposed thanks to the string thong, he’d attempted to initiate morning sex. But she had ignored him and sent him on his way, cap in hand.
_____
From her ensuite, Cassie padded back to her enormous bedroom where her outfit for the day was spread out on the bed. As she began to dress, she picked up her iPhone and speed-dialed Wes, who answered instantly. Putting him on speaker, she gave him a shopping list of instructions and ended the call.
Wesley Hastings was her personal assistant–she’d gone through several of them early in her career. Just thirty-two years old, tall, and effeminately handsome, Wes was more skilled than all the others combined. He was also built like an NFL linebacker, thanks to thousands of hours in the gym, starting when he was fifteen years old. Back in high school when he’d come out of the closet he was mercilessly teased and bullied by a notorious school gang. A friend convinced him to join a private athletic club that taught its members how to street fight. The Marquess of Queensberry would have disapproved highly of their methods, which were to win at all costs by inflicting brutal injury to an opponent during the opening seconds of the fight. Two years later, one-by-one, Wes methodically hunted down and hospitalized all the young men who had tormented him.
He initially went to work for Cassie as her bodyguard. Being gay, there was no sexual tension between them. Indeed, Wes soon became so fiercely protective of her, she’d come to think of him as a brother and even a mother on occasion–a confidant she could trust with her life. She soon discovered he was extremely intelligent and sent him to college to study business administration, where he excelled. After graduating, he came back to her firm, serving as her personal assistant. She paid him an insane salary and couldn’t imagine running her company or even her life without him.
Over the next hour, Wes accomplished several complex tasks. He ensured her meetings for the morning were still firm and the people she wanted to see would be there on time. He arranged for her Bombardier to be on standby for the next few days–ready to go when Cassie had wrapped up her current projects. Once the departure time was decided, her pilot would file flight plans and have the aircraft fueled and ready to go. Canadian and Costa Rican officials were notified–Cassie would clear customs at the resort’s private runway.
Finally, he sent a brief email to Sam Ballard in Seattle. Cassie had decided to give the lawyer a second chance. He had performed admirably in bed two nights ago and she recalled what a good-looking bastard he was.
Attention: Samuel Ballard
Cassie Blackstock will be traveling to a resort in Costa Rica over the next few days. The departure time is to be determined.
If on short notice, you can travel to the Vancouver International Airport and meet Ms. Blackstock at the South Terminal, you will be welcome to accompany her on a brief vacation of four to seven days, depending on her schedule.
You will be officially listed as her personal bodyguard. While it is highly unlikely there will be safety issues while there, in the event any danger does arise, you will be expected to defend her with all your skills.
Please respond within the hour so we can make other arrangements if you are unable to commit to any of these terms.
Regards Wes H. (PA for Cassie Blackstock)
_____
Back in Seattle, Sam heard his phone ping mid-morning. He didn’t recognize the sender and almost didn’t open it, but he hadn’t quite finished his coffee. He was sitting in the original Starbucks near the Pike Place Market, a block from his firm’s offices, and still had a few minutes to kill. He touched the message icon and started reading. He felt his pulse quicken as it dawned on him who this was from and what was being offered.
He had a number of clients lined up for meetings that day and felt he could still handle them. He knew Cassie had a crazy schedule ahead of her, possibly including a trip to Edmonton. He would adjust his calendar for the next two days, making it easy to ‘bug out’ at the drop of a hat. He’d have his secretary tentatively book a number of flights, and cancel the unneeded ones later. If that didn’t work out, he’d drive up and leave his car in long-term parking–it would take two and half hours if the border traffic wasn’t too crazy. His Nexus card should get him through quickly. He sure as hell wasn’t going to let anything get in the way of this opportunity.
He called his boss, a senior partner in his firm, and told him what was happening. If the partner was annoyed at Sam leaving for up to a week, possibly with only a few hours notice, he didn’t let on. Having one of his lawyers a close friend of Cassie Blackstock was worth the aggravation of dealing with a few annoyed clients. The partner gave him his blessing and asked him to report on everything when he returned.
Well… almost everything.
_____
Cassie’s schedule that day and the next went utterly off the rails–it was well after midnight before she arrived home. Her firm specialized in buying distressed companies; big ones, worth muti-millions of dollars, for a fraction of their book value. She would keep them for a year or so, tweaking the management of finances, sales, marketing, and R&D. Then once the company was profitable, she’d find a motivated buyer and sell it for an obscene profit.
She’d made a quick flight to Alberta to finalize a deal with the owner of an oil exploration company. The profits for flipping his company could exceed $50 million–probably more, depending on the fluctuating commodity price of crude oil. So it had been well worth a few hours flying back and forth to Edmonton, which she considered a horrible city. Thank god she’d found helicopter service to the downtown core, saving her a twenty-mile limo ride through a desolate, arctic-like landscape.
Her vacation was delayed a day or two. There was some follow-up work today–a number of online video conferences with all the stakeholders on the same screen. She hoped to be finished by eight o’clock this evening.
Wes called. She told him she would now like to depart late tomorrow evening for the Pasión al Sol in Costa Rica. Wes immediately started making concrete plans and sent a second note to Sam.
Attention: Samuel Ballard
Cassie Blackstock’s departure time is tomorrow (Jan. 14) evening at 10:00 PM from the YVR South Terminal. Check-in at the ‘Private Flights Information’ desk.
Please confirm within the hour.
Regards Wes H. (PA for Cassie Blackstock)
_____
Goddamn, Sam thought, It’s about time.
It was mid-day Friday, and he’d been worried the trip was off. He was not about to call Cassie and ask; he knew her well enough to know she’d be annoyed if he did. She had an independent streak, crossed at his peril. Maybe he could be more opinionated down the road when they had a stronger relationship, but sure as hell not yet.
He called his secretary and discovered all remaining flights today were booked. He could wait on stand-by, but decided he simply couldn’t risk not getting a seat. It would be too expensive to charter a flight–he’d never justify that with his boss.
Sam sent Wes a note saying he’d be there by 10:00 PM.
I guess I’m gonna drive.
Sam arrived at the long-term parking lot at 9:45 PM. It was a long way to the terminal and he ran it, arriving a minute after 10:00. He frantically texted Wes, who immediately texted back, saying there was no rush–she’d been delayed. Wes would text more information soon, but it was probably going to be well after midnight.
Now Sam was sitting in an airport bar, drinking beer and finishing a greasy hamburger. He was filled with anticipation, thinking about what was in store for him over the next week. He fantasized about becoming Cassie’s permanent lover. That would be a nice life–moving to Vancouver into her luxury penthouse. He’d be the envy of every lawyer in North America.
He received a text from Wes, saying departure time was delayed until 2:00 AM.
Over the next few hours, Sam made friends with some other single travelers and enjoyed an impromptu party with good conversation and lots of beer. Just after midnight, now with seven or eight beers under his belt, he found a padded bench and lay back to rest his eyes and perhaps have a short nap. He set the alarm on his phone to wake him at 1:45 AM.
Sam slept through his alarm and woke up at 2:15.
Still partially intoxicated and somewhat confused, he quickly composed and sent a text to Wes and the private airline who administered Cassie’s jet. His phone pinged a few seconds later; the crew was looking for him and preparing to leave. But if he could get to a certain desk in the next few minutes, someone would be waiting for him. Sam had to jog two hundred yards through the terminal to get to the meeting spot.
As promised a young woman in orange coveralls and with large bell ear protectors draped around her neck, was waiting impatiently for him. When she saw him, she spoke briefly into her radio. Without speaking to him, she headed for a metal door with a touchpad lock and punched in a code. The door opened onto an open metal deck with stairs leading down to the tarmac. It was bitterly cold with a stiff breeze off the Strait of Georgia and snowing lightly. Cassie’s jet was parked a hundred yards away with one engine idling.
Even in the cold, Sam was clammy with sweat under his suit from running. He ran to the jet, up the short boarding ramp to the closed entry door, and pounded on it. The door opened from the inside and Sam staggered aboard. The co-pilot scowled at him in undisguised disgust, while checking his passport. With Sam in, the man pulled up the folding stairs, and closed the fuselage door, latching it with a long lever recessed into the plastic molding. Before going back into the cockpit, he icily informed Sam that Ms. Blackstock was in her personal cabin and was not to be disturbed.
Sam looked around the main cabin and chose one of the plush luxury seats; minutes later he’d reclined the seat, covered himself with a blanket from an overhead bin, and was gently snoring, filling the air around him with warm boozy breath and the odor of beer spilled on his suit pants. He did not smell good.
_____
Cassie was finally ready to depart for the airport just after 2:00 AM. Her money people were in Taiwan and she’d been on a conference call with them for the past hour. The deal was signed and the funds transferred. Not a bad day’s work, she mused.
With a tiny overnight bag, she stepped into her private elevator which took her up to the helipad on the roof. A small helicopter with a glass bubble surrounding the cockpit awaited her. The weather was terrible but the pilot was skilled with all of the latest electronic navigational aids at his disposal. Eleven minutes after taking off, they landed at Vancouver airport, directly in front of the hanger housing her Global 7000. She loved this aircraft; she’d only had it a year and it had changed her life. She could travel anywhere in the world, arriving fresh and rested, ready for work or play.
As she boarded the Global, her phone pinged. It was Wes, telling her no one had heard from Ballard. She couldn’t believe it. Is the stupid bastard standing me up? She was again pissed at him. An opportunity like this and he can’t even be here on time for the fucking flight? Fuck him… If he actually manages to get here, he’ll sit in the main cabin. No refreshments; no coffee. Nothing…
She told the flight crew if they hadn’t heard from Ballard by 2:30 AM, they were close the doors and leave without him. Also, she was not to be disturbed until they arrived in Costa Rica.
She entered her cabin, stripped off the clothes she’d been wearing for the past nineteen hours, and stuffed them into a laundry bag. Wes had arranged for an assortment of her vacation clothes to be delivered to the plane. Another large package of her vacation gear had been FedExed to the resort and would be awaiting her there. She had a shower in her tiny personal bathroom, pulled on thin sweats, and crawled into her bunk.
It was a double-sized bunk and would have easily accommodated the lawyer too, but she felt she needed sleep more than she needed to listen to any of his bullshit. She slept naked at home but during flights, who knew what might crop up–if there was any kind of emergency, she might not have time to dress. Ten minutes ago she’d taken a fast-acting sleeping pill and could already feel it working. A few minutes later, she was asleep.
_____
Thanks to all the beer he’d consumed the previous evening and with so few hours of sleep, Sam Ballard didn’t awaken when the plane touched down on the resort’s runway in Costa Rica. He was roused from sleep by the co-pilot when he exited the cockpit after their shutdown procedures. So Sam was in the tiny washroom just behind the cockpit, when Cassie emerged from her cabin. Showered and dressed in fresh clothes, looking as fresh as a daisy, she was curious as to how Sam would appear this morning.
He came out of the main washroom a minute later, having shaved, brushed his teeth, and switched into tropical shorts, tee-shirt, and sandals; he looked reasonably presentable. He greeted her brightly with a little peck on the cheek. She was pleasantly surprised, having heard from the flight crew all about his condition when boarding last night.
A Costa Rican customs officer knocked on the side of the fuselage and came up the companionway without being invited. Inside, he had a look around and decided he wasn’t going to harass this woman or any of her crew. He could sense money here; big fucking money that could make his life hell if he pissed off the wrong people without cause. None of the crew nor the bodyguard had set off alarm bells in his computer. He also knew this aircraft had ferried Ms. Blackstock to this resort several times in the past, with no issues. So unless he saw a body or a box of explosives or big packages of drugs right out in the open, he would rubber-stamp their paperwork. He was gone in less than a minute.
Cassie and Sam exited a few minutes later, to a limousine waiting for them just outside the aircraft. It was only a five-minute drive to the resort, which covered just over twenty acres, bordering the Pacific ocean in a wide-sweeping bay. There were dozens of low sprawling cabins, duplexes, and larger multi-room structures, located along the waterfront. In the center of it all was a four-story 5-star hotel surrounded by several swimming pools and manicured landscaping; more luxurious than any other hotel in the world.
At one end of the resort, they’d built thirty cabins on pilings in an erratic line, out into the ocean. Access to these cabins was via a forty-foot-wide wharf, its deck two feet above the high-water mark. The dock was serpentine with subtle curves along its length, and a private access ramp to each cabin.
The cabin furthest out on the wharf had the best view and total privacy on its front deck. It was the most luxurious of them all, with the most expensive furnishings, and many extra perks. The front of the cabin facing the open Pacific was all floor-to-ceiling windows. A ramp from the front deck led down to a floating wharf where guests could moor a boat or be picked up by a charter vessel. This was the only cabin with a private swimming pool built into the deck. There was also an elaborate hot tub sunk into the deck at the ocean end of the pool.
Set into the center of the living room floor was a ten-foot circular window, looking down through a clear plastic tube, also ten feet in diameter, extending into the sea. The tube eliminated light and reflection so it was like peering down into an aquarium. Many hundreds of species of fish were milling about as though putting on a private show for the occupants above.
This was the cabin Wes had reserved for Cassie and her guest. Because it was the furthest walk from shore, it included a custom golf cart with a clear plexiglass cabin and air conditioning. There was a covered spot to park it at the rear of the cabin. The service staff used similar carts for room service. Any order placed by telephone from this cabin would be delivered within minutes.
Cassie and Sam were shown into their cabin by a young man dressed in the resort service staff uniform–light tan shorts and a crisp, white polo shirt with the resort logo at the breast. Cassie thought this guy could be a professional athlete back home–buff, tanned, well-spoken, and clearly in awe of Cassie. To the young man’s delight, she took his hand in both of hers, slipping a large bill into his palm. Then she pulled him in and gave him a hug, promising he’d be well looked after with great service like this. Sam could see the young man blush, obviously enjoying the attention of this beautiful woman, and he felt a distinct twinge of jealousy. Cassie was looking at Sam while she’d hugged the young man, and he was sure she’d noticed his slight frown. He must be more careful.
When the young man left, they explored the cabin, marveling at its opulence–Sam a bit more than Cassie. She was around this kind of decadent luxury all the time. He tried to not seem like a rube and concentrated on making good impressions–one after another. As he came back out of the huge five-piece ensuite bathroom where he’d just stowed his shave kit, he was shocked to find Cassie naked, leaving the bedroom headed for the front deck.
Not to be outdone, he quickly peeled off his clothes too and headed out after her. As he walked through the ten-foot-wide sliding glass doors to the deck, he saw her dive into the pool and rise to the surface at the far end. He dove in too, enjoying the refreshing bite of the water on his hot skin. He swam to Cassie and side-by-side, they gazed over the end of the pool at the unobstructed view of the pacific.
“This is absolutely perfect Cass; thank you again for inviting me. I don’t think I’ve ever been to a resort as nice as this,” he said.
Cassie smiled, knowing that was true. “For two grand a night, it better be,” she said.
“Ouch… I had no idea we were looking at that kind of dough. No worries–the firm will pick up my end. I’ll figure out a way to call this a business trip. Otherwise, it’ll be a pleasure to cover it myself. By the way, I understand my official role on this trip is as your bodyguard? Let me know if there are any situations I should be prepared for.”
_____
Cassie was disappointed with Sam. The last thing she wanted to talk about was trip finances. She had not planned to ask him for any contribution–she would have come here with or without him. And obviously, his firm knew where he was going and who he was with–he’d likely been bragging about it to his manager. Hell, they’d probably encouraged him, hoping he’d lead to more business with her firm.
Despite the ‘bodyguard’ bullshit, his role here was to be her plaything for the next few days–that was all. She might ask his preferences on a few things, but his unsolicited opinions about their activities would be neither welcome nor tolerated. He’d figure that out pretty soon. If he didn’t like it, he knew where the exit was.
Now she decided it was high time he started paying his way in trade.
“Tell me, Sam,” said Cassie, “Do you know how to make a dry vodka martini? I’ve been assured we’ll find any kind of alcohol we might desire in the bar in the living room. I prefer Gray Goose with Noilly Prat vermouth. Mix and shake it in two cups of ice chips and immediately strain it into the glass. No olive. And very little vermouth–a quarter teaspoon per drink is about right. You can make a small batch, but only one serving at a time so it doesn’t get too diluted in the ice chips. Okay?”
Sam seemed amused as she rattled off her instructions. She turned and draped her arms over the edge of the pool causing the top half of her lovely large breasts to appear above the surface of the water. He felt a stirring in his loins–an erection was imminent. He’d been thinking about making a pass and getting her back into the bedroom but decided it might be too soon–too aggressive. He’d play it by ear; make some drinks, watch her enjoy a few of them, then make his move.
“I’d be delighted”, he said and swam over the edge of the pool alongside the deck. He jumped out, water streaming down through the blond fuzz covering his chest, arms, and legs, feeling her eyes on his bare ass as he strolled back to the cabin.
Ten minutes later he walked back out into the sun with a tray containing a martini glass and an ice-cold Corona. In the fridge, he’d discovered a tray of fresh crackers, dips, segmented fruit, and cheese slices. He brought the tray down to the far end where Cassie was still enjoying the view and set it on the edge of the deck where they could easily reach it. She swam to him, reached up, took her martini, and had a little taste.
“Very nice, Sam. Maybe a bit too long in the ice, but very respectable. What else do you have there?”
She lifted herself out of the water to see the tray of snacks, completely exposing her breasts. Watching from a few feet away, Sam lowered himself back into the water and moved to her side. She was pretty sure of the reason and smiled. He was getting an erection, having just seen her unobstructed boobs for the first time in four days. That was a good thing. She was well-rested after her sleep on the jet, the tropical sun was bathing her body, and was about to have a martini and a snack. There was only one more thing she needed to top this off and decided now was the perfect time to have it. Grasping the edge of the pool, she pulled herself up and climbed onto the deck.
“Sam, sweetie”, she said. “Could I bother you to put some suntan lotion on my back?”
She watched Sam have a careful look around to ensure they had complete privacy–they did. Two bamboo privacy screens covered with climbing ivy at either side of the cabin extended out far enough to ensure they couldn’t be seen from anywhere else on the wharf or from shore. There were boats out in the bay that might see them, but they were far enough away they wouldn’t be recognized.
There were two very plush chaise lounges side-by-side next to the pool and she stretched out one, laying on her stomach. There was a small table between them and she asked him to set the snack tray on it, next to her martini.
“Come to me, baby… I won’t bite,” she said, smiling seductively.
Sam jumped out of the pool and came to her side. He took the tube of lotion, squirted a large dollop in the center of her back, and began rubbing it into her skin, his hands more caressing her body than simply rubbing. He let his palm slide down the sides of her ribcage, finding and rubbing the sides of her breasts. He moved downward and generously rubbed the cream into her backside, apparently not having the nerve to run his fingertips deep down into the cleft between them. Instead, he moved to her thighs and massaged the cream along the length of her legs.
Cassie was enjoying this immensely. As Sam rubbed her back, ass, and legs, she drained her half-finished martini, feeling the warmth of the alcohol streaming through her body, relaxing her muscles and her brain. When Sam finished her legs, she nonchalantly rolled onto her back, her legs partially spread, presenting her naked body to his gaze. He couldn’t help himself and stared unabashedly at her breasts and pussy. He had given up trying to hide his erection which now protruded straight out from his groin, twitching rhythmically to the now rapid beat of his heart. She reached out and gave his cock a quick rub with her fingertips. She could feel the heat building in her own loins as she imagined how this big beautiful cock would look and feel, slamming into her depths. She shivered in anticipation.
But she was going to make him work for it. It was going to be incredibly hot, making him suffer for a while before letting him take her.
“I guess I better do you too, Sam. We don’t want you out of commission with sunburn. Stand here, with your back to me.”
She rose and rubbed a quick application of the lotion into his back, ass, and the backs of his legs. She used her hands to turn him so he was facing her, applying lotion to his chest and arms, then sat back down on her lounge, facing him. His cock was now aimed directly at her face but she ignored it. Squirting out more lotion, she quickly did the fronts of his legs, concentrating on his inner thighs and the skin of his scrotum, carefully avoiding touching his cock.
“Sam darling, would you run into the ensuite and bring me the zippered pink bag on the counter?”
She could see the disappointment and frustration in his eyes but he turned and went, saying he’d delighted. A minute later he was back.
“I have a little favor to ask,” she said. “I’m getting a bit of four-o’clock shadow and I wonder if you’d mind helping me with it.”
She opened the kit and took out some soft doughy sticky pads, showing him how they were used. She peeled off a small wad and pushed it tightly against a patch of skin just above her pussy. A few seconds later she tore it off, ripping away all the tiny fine hairs beneath.
“Before you start baby, would you mind refilling my martini? I’ll need it to dull the pain.”
Sam did as he was asked–a few minutes later, he placed a fresh martini in front of her and a second Corona for himself. Cassie spread her legs and pulled her knees up to her shoulders, utterly exposing her entire groin. Sam took a piece of the sticky, putty-like material and got to work. It took him fifteen minutes to complete the task, which he greatly enjoyed doing. It permitted him to carefully examine her entire nether region in considerable detail, and he found every wrinkle, crevice, and fold absolutely captivating. Even deep between her lovely ass cheeks where he pressed the sticky compound in patches all around her puckered little butthole. Especially there, in fact.
While performing this service for Cassie, he had managed to caress the folds of her labia, running his fingers between them, finding the hard little bud inside. By the time he was finished, he had a painfully raging hard-on and Cassie was leaking slippery clear fluids from the core of her pussy.
He put the wad of sticky material to one side and lowered his face to her pussy, spending another ten minutes licking and sucking every fleshy fold, now bright pink and utterly bare. With his darting tongue, he probed everywhere–every crevice, slit, and slippery hole from her buttocks to her pelvic bone, forcing his tongue deep inside. Finally, he concentrated on her bright pink little clit.
Through all of this, Cassie laid back on her lounge, writhing and moaning constantly. When she had an orgasm, her body stiffened and she folded her arms tightly over her breasts, hugging herself with every muscle in her body straining. Then there was a long rattling exhale of breath and her body relaxed.
Finally, Sam laid her back into the lounge, crawled up her body, licking and sucking the whole way, until he was astride her. She parted her legs and pulled her knees high, just under her chin, utterly presenting her loins to him. She reached down between their bodies, grasping his cock, aiming it directly at the weeping entrance to her core, and thrust her hips violently forward while pulling his hips to her with all her strength.
He felt the length of his cock slide into her and tried to go slow but she was having none of it, bucking wildly, and forcing him to rapidly drive himself into her. Even though there had been no foreplay for him, he was so desperately horny after rubbing her naked body over the past half hour, he couldn’t hold back and pounded himself into her with all his strength. It was all over in less than a minute. He grunted and moaned as he came, sounding as though he had just suffered a painful injury. They lay on the lounge, Sam sprawled on top of her, for several minutes while they caught their breath.
Sam thought that while it had been a really good fuck, there hadn’t been much in it for him other than the actual brief act of fornicating, which was over in a heartbeat. He hoped this wasn’t an indicator of things to come.
_____
As Cassie recovered her breath after Sam climbed off and lay panting beside her, she felt a wave of satisfaction flow throughout her body. This had been an excellent start to her vacation. She felt relaxed and loose–some good food, a couple of martinis, and a really good fuck-session. Life was good. She could feel thirst and hunger and some energy flowing back into her muscles.
Her mind was running through some activities they might do tomorrow. And of course, she was looking forward to dinner in the resort’s extravagant dining room this evening. She also planned to get Sam cranked up for another session before bed, only longer and with some very special foreplay.
Now she could feel Sam’s clammy, sweaty body beside her on the chaise lounge and she rose, diving into the pool for a swim. It would be nice if men just left her alone for a while after providing their very necessary services–that would make it perfect.
Ah well, she could put up with it if he performed like that for a few more days.
_____
They napped after their lovemaking out on the deck, each on their own chaise lounge pulled back into the shade of the cabin. Sam was exhausted after his late-night, all the booze, and sleeping in a reclining seat on the plane rather than a comfortable bed. As he dozed out on the deck, he analyzed the trip so far. He’d never been with a woman like this; she obviously liked to call the shots and he found it slightly annoying. Normally when he was with girlfriends and with his ex-wife before their divorce, it had been just the opposite. He’d been the lead dog.
Thinking about the divorce still made him burn with anger. Thanks to his position in the law firm, he’d made his first million dollars before turning thirty, and was working on his second, when his wife’s private detective photographed him in a sleazy ‘no tell’ motel bed with a client. The fallout had been spectacular; his boss was fond of tormenting him with the old line, “Hell hath no fury like a woman scorned…”.
His wife posted the photos online for all to see and immediately sued for divorce, taking him to the cleaners. He’d lost the house and furnishings, their beamer, most of their investments, and he had to pay her six thousand a month in alimony. He was living like a university student again, struggling to keep his head above the rising waters of insolvency.
Cassie Blackstock could be the answer to all his problems. A few power issues in the pending relationship were not worth fretting about. He could always make changes once he was well established in her life and she depended on him. He would bide his time.
After napping for an hour and still naked, Cassie asked Sam to make fresh martinis and ordered a tray of snacks to tide them over until dinner. The waiter arrived ten minutes later driving a golf cart. From a large cooler, he set platters of hors d’oeuvres on the deck table. Sam was surprised when Cassie didn’t cover herself. She sat up as the young man finished his work and initialed the chit. Sam couldn’t help noticing the waiter’s eyes taking in every inch of Cassie’s body–there was even a slight bulge at the young man’s groin as he collected his cooler and let himself out.
Cassie noticed Sam’s slight frown. “Don’t forget Sam, much of this resort is clothing optional, so he’s seen it all.”
Sam realized she was right. In this resort, guests would dress lightly to pass through the ‘clothed’ areas, but were probably nude all day long in their own cabins, rooms, and out in the common areas. But he suspected there had been a spark between the waiter and Cassie. He hoped it was his imagination.
They were now back on the deck lounges, enjoying their drinks, and nibbling the ‘appies’, which were delicious. Cassie was in a buoyant mood and they chatted amicably. It was late afternoon, too soon for dinner. Cassie suddenly stood and headed for the cabin.
“Come on, Sam… let’s go for a ride in the golf cart and check this place out.”
Sam thought that was a great idea and followed her, pulling on a swimsuit and leather sandals. Cassie slipped into a string bikini, fancy sandals, and headed for the entry. Sam had to hurry to catch her. Each of them was wearing a resort key-card on a cord around their necks; these cards would permit them to enjoy any amenities offered by the resort. He was startled when Cassie jumped into the cart’s driver’s seat, leaving him no choice. He climbed into the passenger side and leaned back into the comfortable bucket seat.
As they drove the narrow lanes through manicured gardens, cabins surrounded by lush tropical growth, shops, bars, and tennis courts, Sam began to get a sense of how high-end this place was. No expense had been spared in its design, construction, and landscaping. This was Disneyland for grown-ups, providing they were in the top 1% of the wealthiest people in the world and could afford it. He felt a wave of pleasure just being here; a place he would otherwise never have set foot in, without the friendship of Cassie Blackstock.
_____
Cassie could feel her body continuing to unwind and the stress flowing from her mind. She was feeling stronger and looking forward to the days ahead. She was still pleased with the waiter, at least ten years her junior; how he’d been googly-eyed seeing her naked, and developed a ‘semi’ under his uniform shorts. He was a distinct possibility in the days ahead. She knew from experience that if very discreet, resort management looked the other way if an employee ‘fraternized’ with a guest. For that very reason, they were very fussy about who they hired. Cassie planned to ‘fraternize the begeezus out of him’ before this trip was over.
The cart was fun to drive and she took secret delight that Sam had assumed he’d be ‘captain’. Maybe if he was paying for all this, she might’ve let him. But this was all her nickel, so fuck him. He was now pouting beside her in the passenger seat. She could also see he was stunned by the opulence of this resort, his jaw hanging partially open at the luxury of it all.
“Hey Sammie, let’s check out the clothing-optional area.”
“I thought you’d never ask,” he said, grinning.
They came to a small parking lot next to a passageway through a ten-foot-high hedge of brilliant multi-colored bougainvillea. Cassie parked the cart.
“Come on, Sam,” she said, leading the way through the passage into the park-like area behind. There was a discreet stand with a rack of little numbered cupboards–Cassie immediately peeled off her bikini and stuck it in one of them. Sam did the same with his bathing suit and they strolled off together.
Feeling the need to tease him a bit, Cassie hooked her arm through his and proceeded to rub a breast against the side of his bicep. She lowered her arm and reached around stroking his ass and slipping some fingers between his thighs, rubbing his scrotum. She could see the desired effect; his cock was swelling and rising slowly from its usual flaccid state. Sam was obviously embarrassed to be walking among so many naked people with his partially inflated cock standing at half-mast.
Sammy abruptly left him standing there and popped into a washroom. Sam found himself all alone on the pathway, his cock at forty-five degrees, and people smiling at his discomfort. As quickly as it had appeared, mercifully it began to subside. Cassie rejoined him a few minutes later and they carried on as she pantomimed being curious about where his big cock might have gone.
“Ha ha… very funny,” he said, causing Cassie to laugh uproariously at his discomfort.
Sam was now getting a sense of the size of this place. It took them twenty minutes to cover less than half of the clothing-optional area. There was plenty to do here; swim in the ocean or in one of several swimming pools, have a drink, a meal or snack, play any of a number of sports including volleyball, basketball, tennis, badminton, pickleball, or golf. There were hundreds of people having a wonderful time availing themselves of all the venues.
Cassie and Sam found a bar in the middle of a swimming pool which required swimming fifteen or twenty feet to reach the submerged stools. Soon they were sitting waist-deep at the pool-bar with its quaint thatched roof, chatting to the young woman bartender. She was a character and regaled them with many stories of the resort and the funny things that had happened on her watch. They were enjoying themselves, immensely.
_____
Sam couldn’t believe his good fortune. Not only was it beyond belief he was with such a beautiful woman, naked in the middle of a pool bar, but there were dozens of gorgeous naked young women everywhere he looked.
Finally, it was time to head back to the cabin and prepare for dinner. Twenty minutes later as they pulled on their swimsuits and headed out through the passageway in the bougainvillea hedge, Cassie quickly jumped back into the driver’s seat. They chatted as they rolled along. Quite conversationally as though making idle chit-chat, Cassie asked Sam a question.
“Hey Sam, I’d really like you to fuck me again before dinner–really pound the shit out of my ass. Know what I mean? And I’ll tell you what… I’ll give you a nice BJ before you do it. Could I interest you in that, big guy?”
She took one hand off the wheel and reached down to Sam’s thighs, running her palm up the insides from his knees to his groin. She cupped the bulge growing beneath and massaged it, delighted to feel some considerable swelling beneath her palm. Sam felt almost embarrassed, doing this while driving down a lane with couples walking alongside. They would not be able to see what she was doing unless they looked directly through the open sides of the cart. He suspected she was trying to embarrass him but the fact was, his cock wouldn’t be getting hard if he didn’t like it.
He reached for her, doing the same as she had, slowly running a hand up the inside of her thighs and rubbing her pussy through her tiny bikini. He could feel her grinding herself against his fingers.
“I’m up for anything you can imagine,” said Sam, feeling the folds of her labia through the paper-thin material of her bikini bottom.
Cassie was squirming now, enjoying the sensations of Sam’s fingers. She now had both hands back on the wheel, concentrating on her driving. A minute later, they pulled into the little parking spot behind their cabin. There was no one on the wharf behind them for a hundred feet–she reached out and slid her hand down the top of Sam’s bathing suit, finding his cock fully erect. She bent over and pulled the front of his suit down as far as she could and took his cock into her mouth. Sam’s head went back and he moaned in pure pleasure as the length of his cock slipped deep inside her mouth.
Sam was watching the side mirror and saw a couple strolling up the pier towards them. He warned Cassie but she ignored him and kept her head moving, sliding him in and out between her lips. The couple didn’t notice until they were nearly ten feet away. Then smiling, they turned and walked back in the opposite direction. But Cassie had now stopped, leaving Sam rock-hard and twitching, several seconds away from a powerful orgasm.
“Come on baby, let’s go inside,” she said, gathering her things and climbing out of the cart. Sam adjusted the front of his suit and followed, gasping in frustration, the tip of his cock peeking out the top of his waistband.
They went straight to the bedroom where Cassie immediately tore off her bikini and knelt on the end of the bed, exposing her perfect bare ass to Sam. He ripped off his bathing suit too, and moved behind her, his erection full and hard as a broom handle.
“Fuck me, baby,” said Cassie. “Let’s see what you’ve got…”
And Sam rose to the occasion in more ways than one. While he would have enjoyed a bit more time exploring Cassie’s body and her exploring his, the sight of her muscular beautiful buns presented for his pleasure, made him forget all that. He moved behind her and for several seconds took his cock in his hand, using his glans to rub up and down through the entire area of her pussy. He concentrated on grinding it hard against her clit and through the inside folds of her labia, Cassie moaning lewdly he did it.
He rolled her onto her back, her ass protruding slightly over the end of the mattress, and pushed her knees forward so the skin over her buttocks and loins was stretched taut. He positioned his glans tightly against the threshold of her pussy and using his full weight, thrust himself violently inside her until his pelvic bone fetched up tightly against the flesh on either side of her quim. She lay on her back hugging her breasts with a look of ecstasy on her face and cried out loudly. She reached out and grasped his hips, pulling them hard against her loins, her fingernails digging into his buttocks, scraping his skin. He slammed into her again and Cassie cried out even louder.
He lost control and began rapidly pounding himself into her with all his weight and strength, each slam of his body seeming to drive her body up the mattress a bit further. He grabbed her legs and pulled her back, and spread them, pulling them to either side of his chest, her knees hooked over his shoulders. All the while he hammered himself into her with such violence their loins made loud slapping sounds, reverberating through the room.
This was too intense to last–in just over a minute, he felt himself exploding inside her and his knees weakening from the outrageous pleasure of it. Cassie’s face was twisted in what might be intense pain or pleasure, and she wailed in a long strangled cry. He collapsed on her, utterly spent, feeling the blood slowly draining from his cock, causing it to soften, become flaccid, and finally slip out of her.
After lying several minutes and catching her breath, Cassie arose languidly from the bed without saying anything to Sam and went to the bathroom. He heard the shower briefly and she padded back out, rubbing her midsection and legs with a towel.
“That was nice, baby,” she said and headed for the living room. A few minutes later, Sam got up and peeked through the door to see where she’d gone. She was stretched out naked on a very plush, soft sofa, and already appeared to be asleep. He wondered why she hadn’t come back to the bed they’d just made love in, and stretched out with him.
He went back to their bed and lay down. In minutes he was asleep.
_____
Sam awoke at 8:30 PM when he heard Cassie moving around the room–he’d been asleep for over an hour. He felt groggy from the drinks they’d had late afternoon and his mouth tasted like shit. He got up and walked into the ensuite intending to shower. He was slightly irritated to find a retractable clothesline stretched through the center of their large shower stall with several of Cassie’s ‘delicates’ and her bikini hanging from it.
She’s a billionaire and she still washes her own fucking panties? Give me a break…
Just then, still naked, she walked into the bathroom behind him. “I don’t want to move those just yet baby. There’s a shower out on the deck by the pool. Would you mind using it?” She went up on tiptoes and gave him a little peck on the cheek, rubbing her boobs against his chest while she did it.
Why doesn’t she hang all this shit out on the patio?
He knew the pool shower wasn’t heated and was greatly annoyed she was not going to move her things for him. He knew it would be a big mistake to make a scene, so he grabbed a bar of soap and his shampoo. Minutes later he was standing naked out on the deck, rinsing his hair under the tepid deck shower. It was okay but hot water sure would have been nicer.
As he dried himself, he heard her call out.
“Our dinner reservation is for 9:00–black tie, baby.”
Fortunately, he’d anticipated this and packed his best tux, which was in fact, his only tux. Someone had come into their cabin today and steamed it, so it looked nearly as good as new. As he came out of the bedroom adjusting his black bow tie, he looked up and saw Cassie standing in the center of the living room, modeling her dress.
It was spectacular; strapless, sleeveless, made from a black, sheer, near-translucent material like gossamer. Her nipples stood out boldly, pressed against the material from the inside. The dress was utterly smooth, hugging her body like a sheath, with no evidence of bra, panties, thong, or anything else beneath. The plunging vee at the bodice exposed half her breasts in a stunning display of cleavage. It had a slit up the side nearly to her hip. If she moved in a certain way, he was sure her pussy would be exposed. He stared in disbelief at this unbelievably sexy garment.
Cassie was smiling at his reaction–he suspected this is what she’d been trying for. There was a beep on the house phone and Cassie looked at the display.
“Our ride’s here. I ordered an enclosed air-conditioned cart so we’re fresh when we get there.” The driver was the young man who’d brought the drinks and snacks to their cabin earlier today. There were lots of smiles and long stares between the young man and Cassie, who’d slipped into the front passenger seat. Sam had to crawl into the rather cramped back seat by himself, again triggering thoughts of annoyance and piqué.
They arrived at the spectacular dining room in the resort’s main building a few minutes later. All the patrons and staff were in tuxes and gowns. There were no menus–diners simply told their waiter what they desired, and a half-hour later it was served. Their personal waiter was a man in his early thirties, slim, fit, attractive, and obviously enthralled with Cassie. She made a point of being very nice to him–flirting would not be too strong a word–smiling broadly whenever he came near their table. This did not help Sam quash his ongoing sense of frustration.
While waiting for their dinner to arrive, Cassie stood and held her hand out to Sam, indicating she wished to go out onto the dance floor in the center of the room. Sam could see eyes all around them swiveling to check out Cassie and her amazing dress. On the dance floor, they moved well together and Sam could see everyone at every table, watching them. As she danced, Sam was sure she was moving her legs so the slit in the side of the dress would widen, baring her entire right thigh. She was also gently pressing her loins against his, subtly rubbing herself against him, until the inevitable–a stiffening of his cock under his tux trousers. After a few minutes, it occurred to him he had very little to do with their movements out here on the floor–Cassie was leading so skillfully, it appeared to everyone watching that Sam was in charge.
After ten courses of salads, appetizers, main courses, desserts, a bottle of German wine, and another of French champagne, by midnight neither of them was feeling any pain. Cassie asked the waiter to arrange for the cart to take them back to their cabin. While entering the cart, Cassie hiked up her dress and thrust a knee forward. Even in the dim light, Sam got a quick glance at her bare pussy beneath. He was pretty sure the driver had seen, too. Sam was again randy with his cock partially engorged, filling the front of his pants. He was looking forward to getting Cassie back inside their cabin.
During the short drive home, a tipsy Cassie seductively rubbed the driver’s hand and kissed him on the cheek. Once inside, she stripped off her dress before reaching the bedroom door. After removing her jewelry, she headed for the large sliding door out to the deck. There was a ramp at the far end, down to a small floating wharf where guests could easily enter the ocean, instead of swimming in the pool. Sam was right behind her, naked as well. They dove into the black ocean, enjoying the feeling of the cool saltwater on their skin.
As they floated on the surface, they noticed their bodies and the turbulence they made in the water around them, glowing with green phosphorescence, framing Cassie’s breasts in streams of tiny glowing green bubbles. It was quite beautiful.
“Sam,” said Cassie, seductively. “I wonder if you’d like to do something very special for me.”
She pulled him to her and putting her hands on his shoulders, pushed him underwater, pulling his face to her groin. Sam tackled the job with great enthusiasm, hungrily licking and sucking her clit, and rubbing his fingers everywhere around her ass and pussy. When he came up for air, she let him take a few deep breaths and pushed him down again. By the third and fourth time, he was breathing heavily, struggling for breath, so she swam to the low dock and hopped up, sitting on the edge of the float with her legs spread wide. Sam spent several more minutes, his tongue embedded deep inside her core, feeling her body stiffen in pleasure at least three times as she enjoyed powerful orgasms.
Finally, she pushed his face away, indicating she’d had enough, and he pulled himself up onto the wharf from the ocean, water streaming from his body. She rose to her feet, gave him a peck on the cheek, and headed for the cabin. Sam asked if she’d like anything to drink and she said no.
He got himself a beer and went to a chaise lounge near the pool. After fifteen minutes, he’d finished his beer but Cassie had not appeared. He went inside and peeked in the bedroom. There she was in bed, apparently asleep. He slipped into the other side of the bed and gently sidled over to her, spooning himself to her so she could feel his erection pressing into the deep cleft between her buttocks. He was extremely horny after seeing her pussy in the cart on the way home and swimming naked with her in the ocean.
She groaned and pushed him back with her hands on his stomach.
“I’m tired, Sam. Go to sleep–you’ve already been fucked twice today. Rub it out yourself if you really need it. There’ll be lots more tomorrow.”
And that was that.
_____
Cassie awoke just before 7:00 AM. She was so conditioned to arising early, it was difficult to break the habit while on vacation. She could hear Sam on the far side of the king-size bed snoring lightly, so she slipped quietly out from under the covers and went for a pee. Minutes later, still naked, she was in the living room, looking down through the glass floor watching the amazing marine life directly beneath. She decided this was better than the Monterey Bay Aquarium and there weren’t a thousand other people milling around.
While she was enjoying the underwater view, she made a phone call to room service and spoke for several minutes.
She found a Keurig machine in the small kitchen–in a drawer below it were twenty or thirty different brands of coffee pods. She chose one, popping it into the machine. She was still drinking her coffee when she heard Sam noisily urinating in the ensuite. She decided to give him a bit of a show. There was a pad of paper on a counter–she ripped off a piece and wrote ‘Watch Me’ on it, then laid it on the glass-floor section. She walked briskly out to the deck, down to the little floating dock. She watched through the big glass windows until she saw Sam wander into the living room and find the note; then she dove in.
Cassie was an excellent swimmer and in a few seconds had swum underwater like a porpoise, until she was directly beneath the glass floor. She came up for a breath of air in the tunnel then dove again, twisting and turning, giving Sam a spectacular underwater ballet with her naked body, only five or six feet below his feet. She did this for about a minute, before diving and swimming underwater back to the little floating dock. She came up the ramp and stood under the shower by the pool, washing the saltwater from her body. After drying off, she wandered into the cabin.
Sam was making a coffee for himself, grinning, with a half-erect cock protruding below his tanned belly.
“I’d of paid good money to watch that spectacular show, darlin’,” he said, smiling. “You looked gorgeous down there, Cass.”
Cassie noticed he made no overt ‘pass’ at her, nor attempt to initiate sex. She suspected he was still a bit pissed after being turned down last night. He’d been pissy yesterday too, when she drove the golf cart, and again when they’d been dancing.
Poor baby… fuck him.
He’d had some outrageously great sex yesterday and would again today if he stopped being such an asshole. He was about to have an experience most men would kill for, so she wasn’t prepared to listen to any whining.
“Sammy, we’re going to have a guest for breakfast,” she said.
“Oh, who might that be?” he asked.
“A friend who works here at the resort. We became friends on a couple of previous trips so we always get together when I’m here. Even though she’s much higher up the food chain than a waitress, she’s going to deliver breakfast and enjoy it with us. She’s actually a personal assistant to the owners and has passed along some interesting information. There is a deal brewing I might be interested in and I’ll need an hour or so to discuss it with her.”
“Any friend of yours…,” said Sam.
“I’ll just mention before she arrives, while she won’t mind you being here, she’s one hundred percent lesbian. If she and I were to become, ahhhhh, intimate, you can be close to us and watch, but you can’t touch her unless she specifically asks you to. Okay?”
“Yeah, sure,” he said, looking bewildered, curious, and intrigued at the same time.
_____
Right on cue, there was a knock at the door and Cassie called ‘come in’. The woman entered pushing a cart with many stainless steel thermal contains on top. She was stunning; medium height, slim, with long jet-black hair pulled back into a thick ponytail hanging to the small of her back. She was of middle-east descent with perfect olive skin, darkened by the sun. She was wearing a resort uniform–shorts and polo shirt. Judging from her nipples thrusting aggressively from inside, she was braless.
Cassie went to her and they hugged like old friends. She introduced the woman to Sam as Lea… no last name. Sam and Cassie were still naked–he had taken Cassie’s cue and left his shorts slung over a nearby chair. Lea looked them both over and said she felt overdressed. She immediately shucked off her shorts and shirt. She was not wearing underwear.
I could really learn to love this fucking place, thought Sam, trying mostly unsuccessfully, not to stare at Lea.
Lea laid out their meal on a coffee table in front of a large, plush sofa in the living room and asked them to sit. Cassie sat between Sam and Lea, who was now spooning hot breakfast items onto small plates. She and Cassie ate their meals quickly–Cassie eagerly anticipating whatever came next.
Lea set her empty plate down and took Cassie’s from her. Then she moved closer to Cassie and took her in a full-body hug, pulling her down until they both lay side-by-side and settled into the plush cushions of the sofa. This left Sam at the other end with their feet nearly in his lap. They kissed deeply for a full minute before their hands started wandering over their respective bodies.
Sam was enjoying a spectacular view; two stunning female bodies with their backsides pretty much aimed him–legs twisting around each other, providing flashes of buttocks, pussies, and breasts. Cassie was the first to crawl down Lea’s body until she was lustily licking and sucking Lea’s labia. To Sam’s delight, Cassie reached to Sam, grabbed his hand, and pulled it to her own beautiful ass, encouraging him to caress and massage her lower body. He did so with great enthusiasm for several minutes as Cassie provided Lea with spectacular oral pleasure.
Both women were writhing and moaning; Sam had an enormous erection and gently slid across the sofa, positioning himself directly behind Cassie so she could feel his cock slip between her lower buttocks. He expected her to move her ass into position so he could ram himself into her. Instead, he was shocked as she twisted her body, moving her ass and legs to the other side of the couch, making it very clear she was not interested in having him mount her.
Her hand again reached behind her, grasping his right hand. This time instead of moving it to her ass, she moved it to his own wood-like cock, obviously encouraging him to pleasure himself as he watched them. Sam was shocked and greatly disappointed–he backed up a bit. He watched them for several more seconds and arose from the couch, taking his half-finished coffee and heading out to the deck.
_____
Lea had just departed with the serving cart and their breakfast remnants. Cassie jumped in the shower and washed away the residues of her amazing session with Lea. When she came back out of the ensuite, Sam was nowhere to be seen.
Goddamn him, she thought. He’s off sulking again–what a total asshole he’s turning out to be.
He’d made a huge mistake leaving when he did. She hadn’t wanted his cock inside her until after Lea had given her pussy a really powerful session with her lips and tongue. But while Lea was not interested in sleeping with men, she liked them watching when she made love to another woman. And she liked watching a beautiful couple making love. The plan had been for Sam to pound the living shit out of Cassie while Lea lay alongside them, massaging them both while he did it. Cassie knew from experience Lea liked to massage Cassie’s pussy, as her partner slowly fucked her. Lea loved the feel of a big hard cock, slipping back and forth between a well-stretched quim. Once he’d left, Cassie brought out a couple of toys and they’d still had a fine time. But it would have been a lot better if ‘shit-for-brains’ had been there with them.
She was trying to decide what to do about Sam when she heard him on the porch outside their entry. The door opened and he came in smiling, holding two Starbuck’s insulated cups, and set them on the coffee table.
“The Keurig is good, but it ain’t Starbucks,” he said.
Cassie was pleased; Starbucks was her favorite coffee and she had been craving one. She took the cup and had a long sip from up.
“Thank you, Sam. This is damn good… where on earth did you find it?”
“I noticed it yesterday, not far from the entrance to our dock. It’s a five-minute walk from here.”
“I’ll remember that–let’s walk there tomorrow morning and have one,” she said.
After a brief silence, Sam said, “I ahhh, left you two alone so you could have your business conversation. I hope you had enough time?”
Cassie knew this was at least partly bullshit, but found herself warming to him again. He seemed to have lost the pissy attitude and looked good in his shorts and sleeveless ‘wife-beater’ shirt. He looked young and robust–his arms and legs as fuzzy as a teddy bear with his near-white curly body hair. The same curls peaked over the top of his shirt, set off nicely against the deeply tanned skin of his muscled chest.
He really is a good-looking son-of-a-bitch. Maybe I should jump his bones right now before we go exploring. Aw fuck it; I’ve just cum about ten times and my pussy is a bit sore… I’ll give it some time to recover.
It was now early afternoon; Cassie announced she’d like to go for a long walk–no golf cart this time. He’d probably like that, not being stuck in the oh-so-humiliating passenger seat. Off they went, Cassie wearing a different, even skimpier bikini than yesterday, and Sam in baggy sports shorts. Before leaving they rubbed suntan lotion onto each others’ backs.
They explored the entire resort; the ‘clothed’ area first, then the ‘clothing optional, having left their swimsuits in one of the cupboards at the entry. They covered the rest of the grounds they’d missed yesterday and had lunch at an outdoor café, the tables filled with dozens of naked couples of varying ages. The manager of the café recognized Cassie and seated them at the café’s best table, with a bit more privacy and a great view of the ocean.
After the lunch dishes were cleared, they lingered over a second beer, having a nice conversation. Sam told her a bit about his early years and attending Law School at McGill University in Toronto, even though he was an American citizen. Cassie gave him a sketchy outline of her past, leaving out most details of her previous family life and background. But they both learned a good deal about each other, and Cassie felt herself warming to him even more. He really could be a charming bastard when he set his mind to it.
They resumed their walk, now along the beach. Sam wasn’t the only good-looking guy around–Cassie was attracted to many of the naked young men playing tennis, volleyball, and practicing putting on a series of greens along the edge of a nine-hole golf course. Many naked young women they encountered were just as desirable, and she fanaticized about several of them, too. Cassie was once again feeling the special glow deep in her loins and decided to deal with it just as quickly as possible.
Now they were walking along the beach with hundreds of couples spread out on towels and beach blankets all around them. Sam couldn’t help checking out many of the very desirable women and was doing some mental exercises to avoid getting an erection. He was barely succeeding. Cassie could see a slight swelling of his cock and was delighted.
Then she noticed a long row of resort beach cabanas and knew she’d found what they were looking for. A young employee working this section of beach walked by and she caught his attention. The name of his ID badge was ‘Carlos’.
“How do we get one of those cabanas, Carlos?” she asked him. She held out her key card and the young man noticed a special code symbol after her name, informing employees she was an A-list guest who must immediately receive the best treatment available at the resort. Anything she requested was to be immediately supplied or arranged with no questions asked. Carlos looked at his clipboard and gave her the numbers of all the vacant cabanas. She chose one–she and Sam headed for it right away.
“Thank you, Ms. Blackstock,” said the young man. “Is there anything I can bring you?”
“Ahhh, yes–an ice-cold Corona for me. You Sam?”
Sam ordered a Corona too.
The cabanas were essentially small fancy tents about ten feet square, just tall enough to stand in. The tent material was a light fabric in a bright tropical floral design. Inside there was a shelf full of towels, a big tub of ice with a range of soft drinks, and two very comfortable looking recliners with thick soft mattresses, nearly the size of single beds. A gossamer-like curtain could be pulled across the entrance and tied closed, providing ‘one-way’ vision. Cassie and Sam could see the beach clearly through it from inside the tent, but they were invisible to anyone walking by, trying to see in. The tent had a number of slits and vents permitting fresh air to circulate inside. It was still warmer in here than back under the beach palms, but quite bearable.
Cassie dragged one of the recliners into the center of the tent until one end was perhaps a foot from the see-through curtain. She lay on her stomach full length with her head nearest the entrance. From here she could still people-watch out on the beach but in perfect privacy.
“Sam, I have another favor to ask if you don’t mind, baby.”
Sam didn’t mind at all and sat next to her on the recliner, running his hands over her muscular buttocks, enjoying their perfect shape and firmness. These were the buns of a long-distance runner.
“Okay baby, what I’d love you to do is lay on top of me on your stomach, straddling me with your legs outside mine, and slip into me from behind. I’m really wet so you’ll slide right in–that beautiful big cock of yours won’t have any trouble finding the way. I don’t need any fooling around beforehand.”
Sam did as asked and with no preamble or foreplay, positioned himself so his cock was pressing gently into the cleft at the base of her buttocks. As she predicted, with one gentle push, his cock slid the short distance between her ass cheeks, into the heat of her saturated pussy. He moaned quietly as his cock penetrated even deeper until his pelvis pressed tightly against her ass cheeks.
“I have a challenge for you, Sammy. If you can do this for thirty minutes without cumming, I’ll promise you a long sensual beginning-to-end BJ, anytime and anywhere you want it. Think you can do it, baby?”
The thought of that was an immediate turn-on for Sam. He couldn’t imagine where or when he might ask her to carry out her promise. Maybe under a table at a bar or restaurant–he’d have to give this some careful thought.
“I’d be delighted to try,” he said. Then something occurred to him. “What if I can’t last that long, Cass? What will I have to do for you? Not that it matters–I can’t imagine you asking for anything I wouldn’t enjoy doing for you.”
“Well, let’s see… what could I ask for? By the way, according to my watch, you’ve been fucking me for a whole two minutes now–you might want to pace yourself, baby.”
Sam did slow down, actually stopping with his cock buried inside her to the hilt. This was feeling so good, he suddenly worried he might not last the full thirty minutes. Although he’d done things like this with previous partners, Cassie was so hot, it was not going to be as easy.
Just then there was movement outside the translucent curtain–it was Carlos with a tray.
“Here are your drinks, Ms. Blackstock,” he said through the curtain. “Okay to bring them in?”
“Hey Carlos, just before coming in here, tell me–while working the beach cabanas, do you often see guests in compromising situations?”
“Sorry, Ms. Blackstock?”
“You know, fooling around with one another, making love, and so forth?”
Carlos chuckled nervously. “Ah yes Ma’am, quite often actually. We are trained not to look and to immediately forget anything we might see.”
“I see… that’s great Carlos,” she said. “Just one more little thing, please don’t call me Ma’am–my first name Cassie would be just fine. Please come in now–do you have a little stand we can set our beers on? It will be a bit awkward reaching down to the sand.”
The curtain was gently pulled aside, just enough for Carlos to enter. His eyes momentarily widened at the sight of Sam laying on Cassie’s back, obviously making love to her from behind. But he recovered nicely, setting a small stool-like bench directly at the head of their recliner, then slowly backing out the way he’d come in.
“Thank you, Carlos. You saw my keycard for the billing?”
“Yes I did, Cassie. No problem at all.”
“Carlos, please add a fifty-dollar tip to this bill for yourself. You’ve done well and I appreciate your help.”
“Ahh Cassie, guests don’t have to tip here but thank you so much for offering. I am honored.”
“I know I don’t have to, Carlos, but I want to. In your training, did they ever mention the old phrase, ‘the customer is always right’?” She could see Carlos smile through the now closed curtain.
“Yes, they certainly did. Many, many thanks, Miss Cassie. Please let me know if you need anything else today, or anytime for the rest of your stay.” He scurried back up the beach towards the bar.
Coming from anyone else, ‘Miss Cassie’ might have annoyed her, but from Carlos for some reason, it was actually quite endearing.
Sam had kept quite still while Carlos had been inside the cabana. Now he felt Cassie’s ass moving a bit, suggesting she needed him to start thrusting inside her again. He slowly pulled his cock back several inches, then allowed it to slide back in. He was relieved there was no mounting heat and pressure deep within his loins, signaling a pending orgasm. But he had to start being more careful–everything about this experience was powerfully erotic and might overload his safety valve at any moment.
Twenty-five minutes after he began, Sam discovered something about Cassie he wished he’d known before he’d made the bet with her. One of her daily exercises was a series of kegel strength-building techniques, permitting her to squeeze the muscles surrounding her vaginal opening. She couldn’t grip a penis hard enough to entrap it, but plenty hard enough to cause considerably more friction to any cock lucky enough to be inside her when she decided to put her skills to work.
Sam was suddenly surprised to feel the pressure around his cock increase in powerful pulses. He was in a push-up position above Cassie, watching his cock sliding rhythmically through the cleft at the base of her beautifully sculpted ass cheeks, and was nearly overcome with the incredible pleasure of the grip-strength of Cassie’s pussy. He sped up a bit, his eyes squeezed closed as she clamped and relaxed, clamped and relaxed, squeezing his cock like a tight, well-lubricated fist.
Before he knew it, after twenty-eight minutes of glorious fucking, he felt the pressure building deep within his loins. Seconds later, before he could even hope to slow himself down, it was happening–spasm after spasm of his thick creamy spunk erupting deep inside Cassie’s pussy, now leaking copiously out the sides, coating his ball sack as he continued to drive himself into her.
Oh jumping Jesus on a pogostick, thought Sam. What have I done… what have I done? What’s this going to cost me?
Cassie pulled her ass away from him and rolled over, lifting one leg. She ran her fingers over her pussy, lifting them dripping with Sam’s semen.
“Well, well, well… what do we have here?” she asked Sam, grinning with delight. “I think that load arrived at the twenty-nine-minute mark. Nice try buddy; close but no cigar. Your ass is mine tonight.” And she laughed out loud at his obvious chagrin.
_____
Late that afternoon when they returned to the cabin from the beach, they had a swim and a nap. Cassie actually slept with Sam on the settee outside on the deck, both of them naked and Sam spooned lightly against her back. He was quite surprised and hoped this meant Cassie was getting even fonder of him.
He was still having difficulty with being her whipping boy. He’d never experienced anything like this before–playing second fiddle to a woman. He’d always been the dominant one in his past relationships and if there was ever any issue, he found a reason to get out of it. He suspected he tended to be a bit overbearing with the women in his life–perhaps like Cassie was being with him. He had to smile, having reached that conclusion.
She’d awoken first and gone into the bathroom, closing the door behind her. He heard the shower running and various clattering at the long brightly lit counter beside the sink. They were going into town for dinner–she had avoided telling him where, wanting it to be a surprise. All she told him was it was going to be a private club with some dinner theatre. Sam was intrigued.
He was quite shaken when they arrived at the building, in a semi-industrial neighborhood on the outskirts of the resort town. There were no cars parked in the area, suggesting customers arrived by taxi. There was no sign suggesting what kind of business existed within if any. The building might have been vacant, it looked so plain.
Cassie had worn a sundress and light sandals, quite modest in comparison to other outfits she’d worn on this trip. Sam was in slightly dressier shorts, a golf shirt, and sandals. Immediately upon climbing out of the taxi onto the poorly maintained sidewalk, the car accelerated away from the curb and disappeared around a corner.
Cassie walked to a large rusty steel door and pushed a button in the ancient cinder block wall beside it. Immediately a small metal gate the size of a postcard opened and a set of eyes looked out at them. They could hear locks clicking inside and the door slowly swung open. The man inside wore a suit and tie and beckoned them to enter.
The entry hall was draped in cheap black curtains. The man in the suit parted them at the end, indicating this was where they were to go and handed Cassie a numbered key. During all of this, he did not say a word.
Passing through the curtains, they entered a shabby hallway with numbered doors. After fitting the key, they opened their door and entered what appeared to be a small locker room, approximately eight feet square. There were rows of shelves and hooks where clothes could be hung. On the bench was a small cardboard box and beside it, a very expensive-looking overnight bag. Cassie picked up the cardboard box and handed it to Sam.
“Sam, please put this on and don’t ask any questions. There’s a photo in the box showing where the various pieces go and how they are worn. I have my own outfit here already. I selected this one for you.”
Sam was feeling some trepidation and didn’t like the feel of this. “What is this, Cassie?”, he asked.
“No questions,” she said abruptly. She pointed to another door on the far wall of the room. “That door leads into the dining room. I’m going to dress faster than you so when you get your outfit on, go through this door. I’ll be in there sitting at one of the tables by myself–come and join me.”
With that, she pulled a tracked curtain he hadn’t noticed, directly across the room, essentially dividing it into two. He immediately heard Cassie opening her case and much rustling, gentle swishing, and clicking as she removed her dress and changed into whatever her outfit was. Sam pulled open the folded flaps of his box and dumped the contents onto the wooden bench along with the instructional photo. He was shocked at what he was seeing.
His outfit was comprised of black, studded leather straps, encircling his neck, shoulders, chest, waist, and ass. A small leather cup with a zipper around the edge would barely hide his cock and balls. His ass would be utterly exposed. The photo showed the order the items should be put on–it looked fairly straightforward.
Sam was feeling highly embarrassed about wearing this in public. He had no idea who would be on the other side of that door. He was shocked Cassie would expect him to wear it in public–even a bit angry. Then he wondered what her outfit looked like? He had two choices; he could simply walk out of here and call a taxi, or he could put on the fucking outfit and see what happened. Just up and leaving would be disastrous–almost certainly the end of his relationship with Cassie. Maybe he would actually enjoy whatever was planned in the other room. How bad could it be?
As he slowly removed his clothes and hung them on hooks, he heard the second door open, and Cassie walk out of the locker room, leaving him alone behind the curtain. It took him five minutes to get his costume on and all the buckles correctly adjusted. There was no mirror, but he could imagine what he looked like. He was afraid it was going to be a gay bar with all sorts of big hairy gay bikers dressed in elaborate leather costumes, hitting on him. He almost changed his mind, thinking he’d be smarter to leave. But a minute later, he held his breath, opened the door, and walked through.
Sam could not believe what he was seeing. There were perhaps twenty couples in a large. nicely decorated dining room, some seated and others moving about the tables–waiters and waitresses. He’d been wrong about the gay bikers; he immediately recognized this theme as dominants and submissives.
She wants me to play at BDSM, he thought. He again considered beating a hasty retreat–getting the fuck out of here. He could see her across the room and instantly understood he was going to be the submissive. With Cassie, what else would he be?
The room was dimly lit, the wooden tables and chairs old and mismatched. The walls were covered with artsy posters featuring black and white photography of old BDSM scenes. At the far end of the room were black, floor-to-ceiling curtains pulled closed, apparently hiding some kind of stage behind.
He made his way through the room to Cassie’s table and made eye contact. She looked up at him disdainfully, as he started to pull a chair out to sit on.
“No!” she said, stopping him instantly. No one around them seemed to notice her sharp tone and paid no attention as though this was quite normal. “You will ask permission before doing anything in here tonight. Understand?”
Sam thought this was almost comical but knew it would be a mistake to laugh or even smile or smirk. “Mind if I sit down, Cassie?”
“For the remainder of evening while here, you will address me as Madam. Understood?”
“Yes Madam,” said Sam, just to get things started. He could play along with this shit for a while.
As he sat, he took careful note of Cassie’s outfit, which was as sexy as hell–all mirror-bright black patent leather. On her legs were skin-tight boots that came to mid-thigh. Around her hips was a thong with a complex series of black straps holding it in place–her buttocks essentially bare. Over her torso, she wore a skimpy leather corset, with a wide laced gap up the front. A bit of black lace at the top hid her nipples until she moved, causing them to pop in and out of sight. Over her upper face, she wore a matching patent leather mask. He would not have recognized her outside this room. In spite of being very self-conscious in this ridiculous outfit and situation, Sam could feel a slight thickening of his cock under the leather cup. Cassie made no indication she noticed.
He looked around the room taking in the various couples seated at the tables. All wore similar outfits–even the wait staff who all appeared to be submissive. Their waiter could only be described as a beautiful young man with a perfectly sculpted physique, his entire body shaved smooth and lightly oiled. Cassie treated him as a slave, making him kneel in front of her as he took their order.
Towards the end of the meal, the curtains slowly opened revealing a pitch-black stage. A demonstration began by a middle-aged couple in excellent physical condition. For an hour, they role-played a love-making session between a BDSM couple, with lots of crawling and groveling on the part of the submissive woman. As they began their foreplay, everything she did was criticized and corrected by the man until the woman did it precisely as he wanted it. During their actual fornication, it was the same. They made love in multiple positions, each of which required many corrections by the man until she got it right. Each time she did something that displeased him, she was humiliated with much scolding, eye-rolls to the audience, and a spirited paddling of her bare ass.
Sam had to admit it was very sexy although definitely not his cup of tea. When the show ended, there was an hour when all the dominants bossed around their submissives, including Cassie with Sam. He found it silly but did everything she required. They didn’t actually fornicate in the restaurant. Sam suspected this would carry on when they got back to their cabin.
But when they finally left, he was instructed to remove the leather outfit and dress in the clothes he’d arrived in. They took a taxi back to the cabin, with little or no reference to the evening. To Sam’s great annoyance, Cassie didn’t feel like making love when they went to bed around midnight, but she did sleep with him in the bedroom.
Sam was startled awake in the wee hours of the morning–he couldn’t tell what the fuck was going on in the room and tried to jump out of bed. But he couldn’t get up and became frantic, waving his arms and trying to roll–nothing was working. The overhead light snapped on.
With his eyes pinched nearly shut in the bright light, Sam saw Cassie standing at the foot of the bed, dressed in her dominatrix outfit from the club. She was pulling and adjusting ropes at the corners of the mattress. As Sam finally came completely awake, he found himself spread-eagled on his back, his arms and legs pointing at the mattress corners, each held securely with a soft half-inch braided cord. He felt strangely groggy and wondered if Cassie had given him a drug to accomplish this. If so, it was dissipating quickly and he felt okay.
She came to his side, checking her handiwork. She moved her hand in front of his face so he could see a small tablet between her fingertips. It was triangular and blue–he recognized it as a Viagra tablet. He kept a few of them at home just in case he needed to perform if he was tired or had already had a couple of orgasms. He liked that the drug gave him a boner like a teenager. The tablet she held looked like fifty milligrams, about double what he required. Before he could react, she popped the pill into his mouth and poured some water in behind it. Sam sputtered and swallowed before he could decide whether he wanted to or not.
Then Cassie was on the bed on her hands and knees, slowly moving around him. She alternated between rubbing different parts of his body from his widely spread legs to the top of his head, using her breasts, groin, and hands to slowly stimulate him. Sam now had a full-blown erection and wondered why she’s given him the Viagra. He was a bit pissed and worried about that–fifty milligrams was more than he’d ever taken.
Cassie swung a leg over Sam’s torso straddling him, facing his head. She moved back until her labia were directly over his cock which was laying flat against his belly, the tip reaching his navel. She suddenly sat hard down, grinding her ass so Sam could feel the weight of her, squirming on his hard-on. Looking down, he could see the tiny leather patch of her leather thong, pressing against his cock, her labia protruding past the edges of the patch. Cassie undid some clasps holding the thong in place and made a show of slowly pulling it out through the gap in the top of her thighs. Her labia were now bright pink and shiny with her fluids, unobstructed by the patch. She lowered herself again so her pussy was pressed down onto the center of Sam’s horizontal penis, and rubbed herself up and down his length.
Now she moved up his body, letting him watch her, apparently enjoying the look in his eyes. When she reached his head, she raised her torso again and lowered herself so her pussy settled on Sam’s lower face. His tongue probed into her, finding her little bud and rubbing it vigorously causing her to moan deep inside her chest. She pushed her groin forward so her pussy slid over Sam’s nose, pushing down so the tip of his nose entered her pussy and she rubbed it hard, moving her hips up and down his face. As she did this, she reached back, wrapping her fist around Sam’s rock-hard cock, still slick with her juices. She squeezed until he found it a bit painful, and he squirmed under her in discomfort. She relaxed her grip and slid her pussy back down over his mouth.
Twenty minutes had gone by since he’d swallowed the Viagra and Sam could feel the effects. His face was hot and his cock was so hard, it was actually becoming uncomfortable, not quite painful, but he was certainly feeling a great deal of internal pressure.
Sam was experiencing mixed emotions. While everything Cassie was doing was incredibly sexy and he wished this experience could last all night, he knew he needed to cum soon or the blood pressure in his cock might cause damage. But he suspected the bitch was being careful not to overstimulate him so he wouldn’t cum. He strained against his restraints but could tell the rope was too thick to break and her all knots would hold.
Sam could see Cassie was getting off on having him bound beneath her like this. She was luxuriating in crawling around him, using his various body parts to rub against and stimulate hers. Reaching into a side drawer, she produced an electric razer and set about shaving every trace of hair growing on his entire nether region. She was very careful, especially on the soft wrinkled skin of his scrotum. Sam did some manscaping at home but nothing like this. Looking down, he was shocked at how different his privates looked with all his hair removed.
Next, Cassie picked up a bottle of massage oil and methodically squirted it up and down the length of his body, then spent ten minutes slowly and firmly rubbing it into his skin, especially the recently shaved skin of his privates, giving his entire body a delightful sheen. She had gotten a good deal of it on herself as she’d rubbed it into him.
Still wearing her boots, she undid a few clasps and slowly removed her skimpy patent leather corset, throwing it to one side. The boots followed after a stripper-like performance to remove them. Now unrestrained, her large breasts stood up proudly, the dark pink nipples hard and puckered. She stretched out full length on top of Sam on her stomach and slid up and down his slick oiled torso. Each time she slid down, he could feel the tip of his cock bump and press against the threshold of her pussy. She avoided sliding back so far that he would penetrate her. But that was not the objective here; she clearly wanted to torture him so he would never forget this.
She reached over to a night table for a large vibrating latex cock, very realistic with prominent veins and a bulbous glans. Now on her knees with her pussy just above Sam’s face, she lubricated the toy, switched it on, and positioned the vibrating glans against her clit. After a few minutes of this, she moved the bulbous head downward until properly positioned, and slowly slipped it upward into her shiny-wet pussy until only a few inches and the battery pod remained in her hand.
Sam’s eyes only six inches below were fixated on this performance, his face now blood red with excitement. She spent several more minutes fucking herself with the latex phallus until she’d had a number of powerful orgasms. Sam watched her body stiffen with each of them and heard her wails of pleasure.
Cassie stood now directly above him and removed the final piece of her dominatrix outfit, the facemask. Her face was ruddy with excitement as she stared down, first into Sam’s eyes, then directly at his blood-red cock, twitching rhythmically in excitement.
“Sam,” she said. “I am going to fuck you like you have never been fucked before in your entire life. Would you like that, Sam?”
He was afraid to answer, not wanting this to end but praying it did soon. His cock was aching now–the pain of it worrisome. The pressure inside was so intense, he felt like it might explode.
Cassie bent and picked up a bottle of water from the bedside table. She opened it, drinking deeply and pouring the rest over her head, shoulders, breasts, and down her back. Sam could see it running down her body, running in a rivulet between her buttocks and stream down her legs. Much of it spilled onto his body and it felt good on his over-heated skin.
Now Cassie lowered herself, bending deeply at the knees until they were just under her chin. This caused the skin and muscular flesh under her ass to stretch tightly, the bottoms of her buttocks stretched tautly over her hip sockets, as hard as fists. She positioned herself so her ass was directly over Sam’s cock. Reaching under her ass, she lifted his cock and positioned it at the threshold to her core, suddenly slamming down her entire body weight, driving Sam’s shaft deep inside her. She’d learned she could handle all of Sam’s length with no discomfort. She raised herself slowly and when his glans was just starting to slide out of her, she rammed herself down on him again, the bottoms of her buttocks driving deeply into the flesh alongside Sam’s rock-hard cock.
She kept this up for several minutes, slowing when she felt Sam was getting close, giving him a rest, then doing it again. She moved her body so one of her feet was positioned on the mattress between his legs and the other alongside his hip, facing his feet and presenting Sam with the spectacle of her magnificent ass. Then she once more started smashing her loins down onto him, impaling herself with his cock violently, again and again. His face was bright red and contorted as though he was in pain.
Sam really was uncomfortable. The bottoms of her hard little buns were striking the upper flesh of his thighs hard enough that it was really fucking hurting. Now she adjusted her position so her ass cheeks were at forty-five degrees to his body. He watched as she rose again, drilling herself down on him with all of her body weight. In his adult life, Sam had never pounded himself into any sexual partner as hard as this, fearing he might do physical damage. Yet here it was happening to him.
Cassie picked up the pace. She was in top physical condition and like a finely tuned athlete, she began a marathon of pounding her ass down against Sam’s lower belly. She tightened her squat position so her ass cheeks were stretched even tighter and harder and began to rhythmically fuck Sam with all her strength. With each frantic stroke, her hard little buns slammed down onto his lower belly on either side of his cock with hundreds of pounds of pressure.
Once Cassie started fucking him at this pace, Sam came quickly. It was a powerful orgasm that built deep inside him, spewing up spasm after spasm of hot surging cum. With Cassie’s back to him, he could see it flowing down his cock, coating the insides of her thighs, and feel it running down between his ass cheeks. Cassie picked up the pace a bit and continued fucking him even harder.
Thanks to the overdose of Viagra, his erection did not subside and Cassie continued pounding her body down onto it. She was perspiring heavily now, sweat running freely down her back and arms. Now barely slowing, she spun around so she was facing him and continued with the onslaught. It was an awkward position she was in with her knees under her chin, and her body folded at her hips. It was as though she was trying to hurt him by driving the bones of her pelvis and hip sockets so brutally against him.
The pain was now so intense, Sam tried to twist his body to deflect her buttocks as they continuously slammed into him. She wouldn’t let him, pressing her palms into his mid-section, preventing him from bucking her off. She kept this pace up for several more minutes as Sam watched her entire body color change, reddening as her final monstrous orgasm built. Even though he was now in great pain, he felt his own body responding, and a second orgasm surged up through him. As with the first, because of the incredible stimulation and Viagra, his cock remained rock hard.
Now Cassie’s orgasm was past the point of no return and she hammered herself down onto Sam’s loins with even greater force, if that was possible. Suddenly her body froze and all the muscles in her torso, arms, and legs seized and stood out like ropes, straining against her skin, as a long primal wail escaped her throat. Her entire weight was on her hard little buns, pressed down into the abused flesh on either side of Sam’s cock. Her body vibrated as the orgasm passed through her and slowly dissipated. She fell forward onto Sam’s chest, her legs finally straightening, her arms encircling him. She was almost sobbing with pleasure. In a minute, they were both asleep.
Sam awoke alone sometime later, the room darkened. The ropes were still attached to his wrists and ankles but the knots had been untied at the corners of the bed. His joints were so stiff, it was difficult and painful to move, but he managed to remove the cords from his extremities. He arose, found his way to the ensuite, and relieved himself. The muscles of his lower belly and upper thighs felt like he’d been pounded with a sledgehammer. He didn’t give a shit where Cassie was and went back to bed.
_____
Right after breakfast, Sam and Cassie were whisked into the town adjacent to the resort in a resort limo. Sam was hurting this morning after Cassie’s incredible performance last night–an apparent continuation of her dominatrix kink. This morning, he noticed there was a lot of bruising in the skin around his lower belly and loins. She had really beat the shit out of him.
He’d been cool with her so far today and in response, she was equally quiet. She’d noticed he was out of sorts this morning but simply ignored him, and obviously didn’t care. Now here they were, headed for yet another destination she had not shared with him.
She was dressed a bit differently today… long pants for the first time since they’d arrived. She wore a tee-shirt with a light jacket, jeans, and stylish leather shoes, even though it was in the high seventies and would certainly rise into the high eighties by afternoon. He was wearing his usual outfit; cargo shorts, a polo shirt, and new cross-trainers with no socks.
They rounded a corner and the limo stopped directly in front of a Harley Davidson dealership with a long row of gleaming Harleys parked outside the main entry.
“Hey Sugar,” she said. “I’m in the mood to rent one of these bad boys. What do you think?”
Sam looked surprised. “Do you ride, Cassie?” he asked.
“Of course… l have a couple of them back in Vancouver and I’ve ridden right across Canada and the US on a variety of hogs. I think we should do some exploring up the coast–it’s a great day for it. Maybe we can find a private place somewhere for a swim.”
That struck Sam as an excellent idea. Then, something she’d said earlier raised concern in the back of his mind.
“Just one?” he asked.
“Sure,” she said. “Don’t worry… I have hundreds of hours with a passenger on the back. You’re going to love it. You can even reach around have your way with me when there’s no traffic coming at us.” She smiled at him lecherously.
“No, that’s not what I meant Cassie, I’d like to have my own bike so we can ride together–not ride on the back of yours.”
Cassie looked concerned. “Have you ever ridden a big Harley before or anything comparable?” she asked.
“Well no, but I’ve got lots of experience with a range of smaller bikes. When we were kids, we’d take them out into the countryside and spend hours on them.”
“What’s the largest you’ve ridden and how long ago?”
“Let’s see… I guess it was a 400 cc Yamaha trail bike when I was back in high school. It went like a son of a bitch,” he said.
“Well Sam, these big Harleys are a completely different critter. They are three or four times heavier with at least triple the power. It takes a lot of training and time before going out in heavy traffic like it’s going to be here. And of course, this is a foreign country where people drive differently than back home.”
Sam could feel his temper flaring. He’d managed to keep it in check so far during this trip, but this was really starting to piss him off.
“Cassie, you’ve pretty much ignored everything I’ve suggested on this trip. We’ve done everything the way you want to do it. I’ve been playing second fiddle the entire time. Goddamn it, I am going to get my own bike and I’ll put it on my own credit card. And that’s fucking that.”
In the heat of his outburst, Sam barely noticed the change in Cassie’s eyes. Thinking about it later, he knew he hadn’t paid enough attention to her as he’d run his mouth. He sensed this was the instant they were finished in every way–friends, lovers, business associates. It was all over–he just didn’t know it yet.
He knew he needed to cool down and stalked off across the parking lot to a display of motorcycles on a wooden platform. As he pretended to examine the bikes, in his peripheral vision he noticed two homeless-looking men approach her, apparently harassing her, probably for a handout. Fuck her, he thought and pretended not to notice what was happening fifty feet away.
The main entry door of the Harley dealership flew open and a large middle-aged man strode briskly to where Cassie was trying to ignore the homeless men. They were no contest for the large man and immediately scurried away down the street. Sam could hear the man talking to Cassie.
“I’m very sorry about that Ms. Blackstock… we occasionally get people like that in this area. Next time, let me know you’re coming and I’ll arrange to have a security man travel with you.”
Sam realized he’d made a second spectacular blunder. He was supposed to be Cassie’s bodyguard, and he’d just allowed two potentially dangerous street people to harass her. A stranger from the motorcycle shop had stepped in and saved her. An ominous dread settled over him as the consequences of his lack of action burned in his mind.
He walked back towards her but noticed her eyes had transformed from the sparkling vivacious woman he’d been with for the past few days, to the flat unblinking stare of a mamba. He suspected this look was what her business rivals saw when down to the crunch over a hard-fought business deal. This ice-cold glare telegraphed ‘do not fuck with Cassie Blackstock’, and was the reason she was a self-made billionaire.
Ignoring his approach, she spun around and walked into the Harley shop. The big guy who would turn out to be the manager directed her to a private windowed office where she sat at a desk. Sam stood back several feet waiting to see what was going to happen next. In the office, the big man picked up a phone and made a quick call. Seconds later, a younger clerk appeared from the back and approached Sam.
“Sam Ballard…?” he asked. Sam put up his hand in greeting.
“That’s me.”
“I’ll help you over here, Sir. Please come with me,” and he headed for another service counter twenty feet away.
Cassie’s bike was all ready and after signing something on the manager’s desk, she headed out the door without waiting or even looking at Sam. It was a truly beautiful machine outfitted with a range of gleaming chromed accessories. Sitting on the bike, she pulled on a matching helmet and pressed the starter button, causing the bike to roar to life. She slowly took off into an adjacent lot to go around a practice track and get a feel for her new ride. As she negotiated the painted lines and tight corners, she managed to do them all without her feet leaving the pegs or the tires wandering over the painted lines. She’d made it look easy.
Still watching through the shop windows, Sam saw her run the bike back to the front parking lot, kill the engine, and swing out the kickstand. She dug in a pocket for her phone, placing two calls, each five minutes in length. She spoke steadily, issuing what seemed to be a series of orders. There was anger in her face as she spoke. Sam continued to watch her while awaiting his paperwork to be prepared from scratch and worried about who the calls may have been to.
Sam’s contract was finally complete and signed. He walked out to the bike he had just rented and climbed onto it. He decided he wasn’t going to use the helmet nor go around the little kiddy track Cassie had used. Once he had the bike running, he pushed back the kickstand with one foot and checking to see that Cassie was watching, cranked the throttle and roared out into the street.
Fuck that, he thought. Time to get this show on the road and show this bitch a thing or two.
He was surprised at how responsive the bike was to the throttle and enjoyed the deafening roar from the exhaust pipes, even though he was struggling to control the machine, after nearly striking a car parked on the opposite side of the street. He glanced in his mirror and a hundred yards back could see Cassie pulling out onto the road at a much more subdued speed than him.
This side street entered a roundabout providing access to a more heavily congested street with bumper-to-bumper traffic. Sam entered the roundabout much faster than he should have. He lowered his left leg from the peg in case he had to steady the bike, much like he used to do with the nimble trail bikes of his youth. But his new cross-trainers had an aggressive sole and instead of sliding along the hot pavement, they grabbed, pulling his body to one side and causing the bike to lurch to the left. As the bike swerved, his right hand twisted the throttle causing the engine to roar and the bike to sling-shot forward.
Sam hit the taxi in front of him at over thirty miles per hour, caving in its bumper and trunk lid, and buckling the bike’s front forks. After shoving the taxi ahead several feet, the bike fell over flinging Sam sideways, the side of his head contacting a concrete curb around the inside of the roundabout. As the bike came to rest on its side, Sam’s left leg was pinned beneath, although he couldn’t feel it, having been instantly knocked unconscious. He would have no further memory of his accident until an hour later when he awoke in the hospital.
_____
Cassie was enraged when Sam lost his temper at the Harley dealership. The ungrateful bastard–he’s in paradise, staying in a five-star cabin, eating at five-star restaurants, and hanging out with some of the most beautiful and wealthy people in the world. I’m not exactly chopped liver either and he’s been fucking me for two days. There was no ‘spoiled-fucking-brat’ rants about that. And to top it off, the chicken-shit bastard ignored the two miscreants trying to rob me.
These black thoughts raced through her mind as she watched him enter the roundabout a half block in front of her. He was going considerably faster than he should be, so she was not surprised to see him lose control and smash into the ass-end of a taxi.
She slowed down and nearly stopped as she approached the accident scene. A policeman who had been directing traffic and the taxi driver were attempting to lift the Harley off Sam’s leg, which appeared to be bleeding profusely. He didn’t seem to mind though, as he was obviously unconscious.
Fuck him. Things are under control here. I’ll have Wes call the hospital later and deal with the stupid bastard.
In her mind, she continued to rage. What a stupid fucking asshole–how did I not see that sooner? What did the stupid fuck expect, not wearing a helmet? How could someone smart enough to become a lawyer, fuck up this royally? How could he stand by and let those two fuckers harass me?
Knowing he was being attended to, she pulled back out into traffic, now in gridlock thanks to Sam’s accident. She ran the bike between the stalled lines of cars until she found an alleyway that would get her out of this congestion. Minutes later, she was headed back to the resort. She had several chores to carry out and needed to get there quickly. This bike would be fastest–if she didn’t need it again, the dealer could come and pick it up in the resort parking lot.
_____
The accident wasn’t the only thing that would ruin Sam’s day and many days to follow. He awoke in the town’s tiny emergency ward, a doctor standing on one side of his gurney and a nurse on the other. As foggy details of the accident slowly came back to him, he was hit with waves of staggering pain, radiating from his left knee and his head which felt like it was being crushed in an enormous vice. He couldn’t constrain a moan which alerted the doctor that he was awake.
“Hello Mr. Ballard, I’m Doctor Sanchez and we are going to take excellent care of you today. How do you feel… are you in pain?”
Sam told him he was indeed hurting terribly–the doctor immediately ordered a morphine drip into his IV line. Sam felt a warm happy wave spreading throughout his body while the doctor continued talking to him. Among other things, they asked whether he had medical insurance. He explained the woman he was traveling with had arranged all of that. She was probably out in the waiting area and would explain everything.
The nurse shook her head, saying there had been no one asking about him since he’d arrived. He told them his legal firm would look after everything and that seemed to satisfy them. The doctor told him he may require surgery–they’d know after running some tests. At that point, Sam passed out, this time in a pleasant narcotically induced coma.
He awoke six hours later. The same nurse was in the room attending to machines alongside his bed. The pain in his knee and head was still terrible. When the nurse noticed he was awake, she explained that no bones were broken, so he did not require immediate surgery. However, he should see his American Doctor immediately–there was tendon and soft tissue damage that would likely require surgery back in the states. They would keep him overnight and release him in the morning with a knee brace. Also with a prescription for narcotic pain killers which she assured him he would need.
He asked if Cassie Blackstock had been here to see him. The nurse said there had been no visitors or calls. Then as an afterthought, she said a large package had arrived for him, and an envelope. Across the ward, he could see a cardboard box, neatly sealed with packing tape. The nurse read the label to him–‘Personal property of Sam Ballard’.
She handed him the envelope and he tore it open. Inside was a single sheet of printer paper with details of a flight reservation, leaving tomorrow afternoon at 4:45 PM, to Vancouver, BC. It was in coach, in the middle seat of a row of five. There would be five landings to pick up more passengers in Nicaragua, El Salvador, Honduras, Guatemala, and Mexico City. The flight would terminate in Los Angeles twelve hours after departing San Jose, with a six-hour layover until the next available connecting flight to Vancouver. Sam could not believe what he was reading.
Why Vancouver? he wondered. Then he recalled his car was in long-term parking there. How the fuck am I going to drive it?
This must be a mistake. He’d take a taxi over to the resort tomorrow morning and talk to Cassie about it. He’d get it sorted out.
Mid-morning the following day, Sam’s knee was still throbbing in excruciating pain–his headache was still there but a bit subdued from yesterday. The taxi pulled up to the resort’s main entrance and Sam carefully exited, struggling with his new aluminum crutches. The driver lifted out his cardboard box and set it on the ground, clearly unhappy about being paid with a credit card. Sam had no cash in his wallet.
As the taxi roared off, Sam made his way to the resort entrance, where he was surprised to see a resort security officer. Sam pulled out his plastic key-card and approached the man, who instantly recognized Sam, holding up a hand to stop him. In excellent English, the officer informed Sam his key-card was canceled, and he was no longer permitted to enter the grounds.
Sam asked to speak to Cassie Blackstock and gave him their cabin number. The officer told him Ms. Blackstock had checked out of that cabin and new guests had checked in. The man had no idea of how Sam might contact her. Sam gave up and hobbled back to the parking lot where he’d left his cardboard box.