May the Best Lover Win

Author's notes:

I'm trying a new approach with this story, offering you as the reader parallel perspectives on an erotic encounter, by telling it concurrently from the viewpoint of both individuals, Rick and Blair. So, in other words a 2 for 1 of sorts.

The character of Blair was new and interesting for me to develop authentically, so here's a thank you to those LIT writers who offered instructive insight which helped me delve into her mindset respectfully. Rick's character in contrast, coming from this filthy male mind, spilled out on reflex.

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Friday Morning - RICK

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From the thin slices of morning sunlight creeping through the blinds, the small but unmistakable bud of a nipple was visible beneath the sheet covering her body.

Rick lay awake, admiring the beautiful stranger next to him, still piecing together murky fragments of his prior night. He'd slept naked on top of the sheets it seemed, passing out at some point after their tryst had crested, drunk from both alcohol and the intoxicating pleasure they'd enjoyed together. At some point, she'd apparently slipped underneath the sheet. He'd slept through that.

"Her name is.... Jessica. No... it's Jennifer," he thought. "Fuck. I'd better figure it out before she wakes up."

Long, autumn hair covered her face as she slept, her head turned to the side facing him. Rick felt he might remember her name if he could see her face, but wasn't interested in waking her yet. That said, he couldn't resist the urge to glide his hand down along the sheet, over the length of her body, across her hip and down to her thigh. The subtle action aroused him, blood swelling his manhood.

She stirred beneath his touch, an inhale then a sigh emerging from her as she forced open her groggy eyes. She brushed her hair back and smiled, sleepy, but still charming for just waking up. His hand traced up her leg, hip then stomach, continuing across the nipple, testing her body's reaction through the sheet.

"Mmm....You're horny, baby," she groaned and smiled.

In a flourish of movement, she flung the sheet off her, pushed Rick onto his back and landed on top, straddling him. He smiled back, pulled her down to him and kissed her, mouth open. Morning breath be damned.

"Jennifer. Your name is Jennifer," he remembered silently. The helpful recollection came with other salient facts about the prior night; Serving her white wine at the bar where he worked, her flirty demeanor and their mutual attraction, then their walk on the beach after closing time. Most of all, he remembered her eagerness to return with him to his luxurious house up in the hills.

She glided the cleft of her vulva against his erection. He responded with his well practiced alluring gaze and returned the pressure against her. He felt the wetness forming between them. Without foreplay or hesitation, she lowered herself onto his cock.

Physically, Rick was a living portrait of desirable masculinity.

He was tall, naturally muscular, with wavy, sun bleached dirty blonde hair, then darker body hair perfectly sprayed across his chest and down the center of his toned abdomen. He was tan from countless hours of windsurfing and any other outdoor sport available. His energetic blue eyes, when paired with the chiseled jawline he inherited from his father, made him annoyingly handsome. The local girls on the island generally despised him, that is until he showed interest, after which they desired him.

Last night was the same.

It was noon by the time they'd fucked away the morning, made breakfast and she was dressed to leave.

He recalled over his second cup of coffee that Jennifer was a travelling nurse, working on his island for two more weeks before returning stateside. Recalling her situation put him at ease. She was an attractive and deliciously horny woman, who enjoyed his company both in bed and out, but one who wouldn't be around long enough to get attached.

In other words, she was everything Rick wanted in a woman.

He'd brought her to his house that night on the back of his vintage Vespa scooter. She'd loved it. Zipping up the twisting hillside road in the dark, Jennifer described it in the morning as a highlight of her island experience, besides their night of steamy sex.

She took out her phone to call a taxi to transport her back down the hill to the hospital dormitory, her spartan housing while on the island. Even though he had other obligations this day, Rick would have nothing of that, insisting he take her.

Back on the Vespa, traversing the sharp switchbacks down the hill, her hands were wrapped affectionately around his midsection. The warm Caribbean breeze blowing across their faces, Rick transformed into a charming tour guide, pointing out sights and landmarks visible from various high points along the road.

"That long curved beach you see to the right, the one with the sailboats moored,... that's Cowpet Beach," he instructed. "It's one of my favorite spots on the island." He continued, although with a deliberately non-committal tone, "We could go there sometime. It's private access but I have a friend who lets me use his access code." Jennifer nodded back enthusiastically.

He carried on. "Over there is Bolongo Bay. That's where Mr. Busby's, my beach bar is. You remember that place, right?" Rick grinned confidently as she squeezed his belly and shouted into the wind, "Of course I do silly!"

Rick parked his scooter in front of her building, an older, traditional Caribbean structure adjacent to the newer, more modern hospital. They both got off and Rick embraced her warmly, kissed her on the forehead and said goodbye, for how long he hadn't really considered.

Rick was not born on the island, but had definitely come of age on island time.

He had moved there with his parents in his mid teens. The family officially migrated to the island to adopt a new and relaxed lifestyle, although his mother joked in private that they came to avoid the prying eyes of the tax man. Rick had graduated from the island's only private prep school and convinced his parents to let him start college on the island to complete basic course work before transferring stateside to complete his education later.

Rick's real objective was never to leave.

He loved island life, the carefree pace, the weather, the water sports, but most of all the women; island women, tourists, they all held their own special attraction for him. Six years later, college had become more of a hobby than a commitment, though he kept just enough on his plate to convince his parents he was still trying. They'd returned stateside three years ago and left him in charge of their stylish hilltop home with its sweeping views, private pool and prestigious location. Between having the run of the house and tending bar four nights a week, he was living his own dream.

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Friday Morning - BLAIR

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She was sweating profusely, which validated the sheer difficulty of her effort and what was still to come. The boiling tropic conditions, from the confluence of direct sun, ocean borne humidity and temperatures in the high eighties, created a sauna like environment for Blair's workout. Today was Friday, which meant suffering through a solo cross-fit program outdoors. The beach park on the north side of the island was rarely visited by tourists, and the locals never showed up till afternoon. In that sense, it was her own private outdoor gym.

She paused to catch her breath, physically spent, hurting, especially her upper body. But she was only two-thirds through the scripted workout she'd written out the night before. At least the pull ups were behind her now. Next came jump squats, alternated with up-downs, and thirty yard sprints sequenced in between, in the soft sand. "Suck it up, sweetheart. Let's go," she said out loud to no one in particular.

Daily exercise, and in Blair's case, grueling, painful, exhausting exercise, had evolved into a sacred ritual in her life. The harder the workout, the more concentration it demanded, therefore the more it would carry her away from anything in her day-to-day world that might emotionally wear her down. When working out, she was calm, safe. And when she wasn't, the physical results of her regimen gave her added confidence. This wasn't just a phase. She had years ago resolved that she would continue, to whatever degree physically possible, for the rest of her life.

She finished her final sequence, then carried the twenty pound dumbbells, along with the sand covered exercise mat to her island car, an older VW Beetle. Island cars were those that had been exclusively owned on the island, and because of the minuscule geography, were driven limited miles and stayed in operation forever. She loved hers, even though it was a bit of a chick car. She saw it as a subtle reminder that despite her tough persona, she was, after all, still a girl.

Driving home she passed her ex-lover Kara's apartment building, and resisted the urge to look. They'd shared a sixteen month, loving and caring relationship, and had been deeply committed to one another. But for reasons she still wasn't clear about, it had fizzled. In their final weeks together, Kara had rambled through a myriad of feelings, which grew into reasons, little of which seemed to reflect the reality of their relationship, and none of which made sense to Blair. She summed it up in her heart that Kara had simply fallen out of love with her.

Life as a gay woman in a hetero world wasn't a cake walk for anyone. But living it solo, without a partner, made it tougher for Blair. She was known by all, and knew in herself, that she was a strong, confident woman. That was not a question. But more than most people, she simply craved affection and companionship.

Over time, Blair had developed a public persona as a tough, physically impressive female, To the point that being gay had for some become a side note. Not that she'd ever harmed anyone or even come close to a physical altercation, she simply gave off an aura of someone you would never want to mess with. She liked this result. Add in that island culture was largely supportive of its gay community, and she had become more at ease about her sexuality than at any point in her life.

She'd moved to the island three years prior, admittedly on the run from an abject lack of acceptance by her family of her decision to come out. Her parents had united against her with a mixed message of "It's Ok honey, we love you. Just don't go out and tell everybody." For her, after years of masquerading as the person her family preferred, it was the final straw.

After landing on the island, with no friends, and nothing but an apartment lease and two suitcases to ground her, she'd occasionally sought and found companionship in the form of one-night stands. Visiting tourists, both women and men, were frequently on the hunt for a little vacation sex and came to her willingly whenever she showed interest.

Since her early years, Blair had known that she was attracted to women and desired relationships with the same sex. Nonetheless, she still appreciated the rush of a hard cock and the strength of a masculine lover in her bed. After all, human biology works as well as it does for a reason, she believed. She just had no desire for a relationship with any man.

In most social circles, this would label her as bi, but Blair kept this part of her sexuality to herself. She believed that most of her gay friends, not to mention a lover, might not understand. As for the heterosexual world she lived in, it was simply easier to be known as a gay woman, than to deal with uninformed and oversexualized questions about why or which or when.

Arriving at her apartment, she noted her sixty plus, retired neighbor sitting in the lawn chair on his side porch, which is where she usually found him. As had become their routine, Blair stopped to chat, her tight workout clothes accentuating the muscular curves of her body. As usual, he faked his way through the conversation while mentally undressing her, his aroused grin unmistakable as always.

She viewed him as a harmless, older man, albeit unabashed with his objectified view of her, and was happy to let him gawk. She departed in a manner that offered him a full view of her butt. "Dudes are such predictable idiots," she thought and smiled to herself as she strutted to her apartment.

After downing an energy shake, Blair connected her phone to her music system, selected Love is a Bitch by Two Feet and turned the volume up loud. The heavy bass rattling her windows, she headed to her simple bathroom for the hottest shower a human could tolerate, at least thats what Kara had often said. Steam filling the tiny room, her skin turned a bright shade of pink from the intense heat as the water cascaded off her head, around her neck and down her body.

She looked down to admire the hard, rippled surface of her stomach and the defined muscles in her thighs. Her hands drifted down the center of her belly, stopping to linger on the sensuous, subtle valley between her thighs and her lower abdomen. Fingers gliding lightly, she reached behind and caressed her ass, then back around and up to tease her nipples.

Blair lifted her face to the hot shower as she caressed and pulled at the firm buttons protruding from her breasts. Petite in stature, yet lean and athletic in physique, her nipples were outsized in proportion to her small breasts. She was aroused by her own touch.

Legs spread and knees slightly bent, she dropped her gaze downward, where the water fell across her womanhood, and where her wanton pussy now demanded attention. Working a middle finger into the wet, dark hair, Blair teased and rubbed circles around her clit, as the other hand slid lower, fingers slipping inside of her slick opening. Fucking herself as she touched her clit, her passion rose easily.

Blair's pelvis grinding hard against her hands, her pace and intensity grew, until she raised her face back up to the spray of the shower and climaxed, screaming into the flow of water, hands clutching her pulsing cunt.

As her flow of energy subsided, she relaxed, and stood calmly under the water. She took a deep breath followed by a long, slow exhale, as she'd mastered from years of practicing yoga.

She'd not had sex since her breakup with Kara months earlier. She was, for the most part, emotionally past the loss of her lover, but her unsatisfied libido was building, and she found herself masturbating more frequently, often in the shower like today, but also in places or situations that surprised her in hindsight. She had recently pleasured herself in the ladies room at work, during midday in her kitchen, and even once in her car, in the dark parking lot at work after her shift ended.

Companionship aside, Blair needed sex, and it was starting to show.

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Friday Afternoon - RICK

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Scooting back home, he rounded the final hairpin turn before reaching his house, and noticed the elderly, retired couple next door out at the end of their driveway, both standing with hands on hips, staring at their car. Rick stopped. "Hey Sam. Hey Dolores. What's happening?"

Dolores pointed. Sam only offered one word, "Flat."

Rick knew very well what that meant on the island, waiting. There wasn't a dependable roadside assistance option that wasn't already married to the rental car companies. So having a flat tire meant waiting for an eternity for assistance, or taking care of it on your own. It was clear that Sam was not in physical shape to change a tire.

Rick knew the right thing to do was help his neighbors where he could, so he parked his scooter, stripped off his shirt and went to work. While the couple didn't hold Rick and his playboy lifestyle in high regard, they both were gracious with their appreciation.

Dolores discretely surveyed Rick's physique, swooning silently while trying not to let Sam catch her gawking. "I'll bring you a cobbler over this evening, Rick. Thank you so much!" Rick was polite in return. "Thanks Dolores, I'll be at a friends birthday party later down at the marina, so just leave it on the table on the porch if I'm not there."

Sweating in the tropical heat, his shirt still beneath him on the seat, Rick motored the additional hundred yards home and walked inside. He thought to check his phone and confirm the plans for tonight. He'd taken off work, a busy Friday at that, for a good friend's birthday event. It was going to be a memorable occasion if the party went as planned.

He realized his phone wasn't in his pocket, searching around the house before locating it on the kitchen counter where he and Jennifer had made coffee earlier in the day.

One look at the screen and he yelled out, "SHIT!"

He had five missed calls, two voice mails and four unanswered texts from Blair, the other bartender at Mr. Busby's Beach Bar. He only read the text messages.

RICK, WHERE IS THE KEY TO THE 2ND LIQUOR CABINENT? I'M HERE TO TO OPEN

RICK DID YOU GET MY VOICE MESSAGES? WHERE IS THE KEY?

RICK?????

WTF!!!!!

Rick scrambled around his bedroom, rummaging through his unmade bed, finally locating the shorts he'd worn the night before, hidden partway under the nightstand. Sure enough, there was the key labeled CABINET #2 in his front left pocket. He voiced a text message back to Blair as he raced out the door and jumped back on his scooter.

In any other location, a handsome shirtless man flying around on a moped might have drawn some attention. Not so on this island, as it would be just another common sight in paradise. However, Rick stirred up plenty of attention, as he ran three stop signs and passed multiple cars on the shoulder as he frantically sped to Mr. Busby's.

As the two main bartenders, he and Blair split up most of the shifts for slow nights and shared the responsibilities on busy ones. While he had been working there almost two years longer, Blair had become the de facto senior between them. She was older, more committed to her work, and better with the details. Not that Rick wasn't a reliable employee, it was more a matter of who was the natural leader between them.

Right now, with the key in his pocket, he was just scared to death of her and the unavoidable confrontation he knew was coming.

Mr. Busby's Beach Bar was an island staple for both locals and well informed visitors. It was set on an idyllic beach, forty or so yards away from the water's edge and separated from the tranquil bay by a grove of tall, random palm trees. It offered tables scattered about on the shady patch of sand, along with several hammocks, plus a low, wood deck directly on the sand as a dance floor.

Under a broad tin roof, the centerpiece of the open air establishment was the traditional rectangular bar, with the liquor and supplies displayed down the center, its own faux tiki-hut roof above and old school, wood bar stools around. A dozen or so tables surrounded the perimeter, the entire structure rising a few steps above the sand.

Mr. Busby's was already open with a handful of customers scattered around as Rick barreled up the side steps to the open air space, still shirtless, breathing heavy. Everyone heard the commotion and looked over. The soothing sound of Bob Marley's Is this Love filled the silence, in jarring contrast to the visible tension between Rick and the woman behind the bar.

Blair didn't say a word. She just held out her hand from behind the bar, her edgy style, buzz cut hair, along with the fierce look on her face intimidating him even more than he'd expected.

"That is a pissed off woman," Rick overheard a customer say, "Poor dude."

Rick placed the key in her hand and waited for the bomb to drop.