May the Best Lover Win

Rick and Blair leaned forward together to read the napkin, then stared absently at each other. Neither spoke.

The remaining time before closing was marked by tense silence between them. They barely acknowledge one another, completing their close out tasks efficiently, then Blair locking the cabinets and killing all but the security lights as Rick walked to his Vespa.

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Saturday - BLAIR

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Blair woke up before dawn, muscles sore from the prior day's workout, which told her she had done well. "If you don't feel it later, it was too easy," she had been taught early in her fitness journey. She was naked below the waste under her sheet, a reminder that she'd masturbated before dozing off. The fact that it was Rick about whom she'd fantasized, she brushed aside. "Enough about him," she thought.

Arriving at work, she was surprised to see that Rick had come in well ahead of her. Barely inside, she was caught off guard as he shouted an apology to her from across the bar. She stood motionless, listening as he fumbled through his excuse for being so irresponsible before.

Blair stared intently at him for a moment. He'd not only arrived early but had completed their prep for Saturday night. And now here he was, looking hopeless and vulnerable, awaiting her reaction to his lame, albeit honest apology. She considered the comments she had heard from the other party goers the previous night, and with his sincerity now, decided to let him off the hook. "I hope you at least got laid... dumbass." Seeking to lighten the moment, she added, "It's fine. No harm done. Customers got served."

She proceeded behind the bar. Blair had picked up some chatter on Friday that in Rick's haste to bring the key to her, he'd irritated one of the local police officers and was likely to get written up for reckless driving. She shared this bad news with him, and observed that he took it all in with surprising calm.

The Saturday night crowd was normal in size, but more boisterous than usual. It made for an energetic and fun vibe as she and Rick ran their normal, well practiced work routine. At one point mid-evening, Blair noticed an attractive female tourist settle into the one available bar seat at the end. She made immediate eye contact with Blair, her bright smile drawing her over as if silently calling her over.

"Hi! I'm Cassandra. I love this bar!" She said to Blair. Captivated by her energy, Blair couldn't help but reach out to shake the woman's hand and introduce herself. Cassandra held Blair's hand longer than necessary, while beaming a smile which Blair felt might melt her on the spot. "Make me the most tropical drink you can think of," she enthusiastically commanded.

Blair felt a rush of energy as she released her hand, acknowledged the request and turned to make the gorgeous woman a traditional rum punch in a freshly cut coconut. She smiled at herself, realizing how instantly smitten she was. Cassandara had natural, wavy blonde hair, but had done nothing special with it, giving her a college coed look, although she was definitely older than college aged. She was not wearing any makeup, but still glowed from a tinge of tropical sunburn on her face and arms. Her emerald eyes were the crowning jewels on her beautiful, vibrant appearance.

She was wearing a snug, black tank top and simple white shorts. She bore no jewelry on her left ring finger, a point that gave Blair hope that Cassandra might be as interested in her as she was in Cassandra. The flirty conversation that followed over the ensuing hour brought Blair to hope that there might be more in store as the night wore on.

At one point, she noticed Rick engaged with Cassandra as he took her next drink order. This was not unusual since they shared the responsibility for caring for customers at the end of the bar. It did seem that Rick was unsettled for a moment though, although it passed before she thought to inquire what was up. Rick produced a martini for Cassandra before Blair found a free moment to reengage with her.

She listened intently as Cassandra told her the story of the inhospitable wedding party with whom she was stuck on the island. Blair commiserated with her at the tale of how her outsider status amongst the bridesmaids made for an unpleasant situation. "But all is good now! I've met you, Blair!" she concluded. Blair couldn't help but blush, her heart racing at the show of interest. Cassandra held her gaze again, as she leaned in and said quietly to Blair, "You're sooo gorgeous. I hope we get to spend more time together before I travel home."

Blair, captivated by the effusive compliment, was hooked. "That would be amazing," she replied.

Later, Blair was smiling to herself subconsciously as she focused on other customers, and saw Rick retrieve Cassandra's empty glass with the intent of making her next martini. Unable to hide her excitement at the attention she was getting, she motioned discretely toward Cassandra in a way Rick would understand their mutual interest. She knew it was uncharacteristic in her relationship with Rick, but didn't mind him knowing this, as much as a show of friendship with her coworker.

Simultaneously, she heard Cassandra say something to Rick about "...seductive" and then witnessed her giving Rick a piercing, seductive smile.

Blair's breathing stopped, as her pulse jumped at the implications; Cassandra was flirting with Rick. Her heart sunk.

"Are you fucking kidding me?" She whispered to him.

Whatever contrition he had shown earlier in the day was now gone, as Rick paused briefly, then summoned Blair to a private spot down the side of the bar. With surprising authority, he explained that Cassandra had been hitting on him all evening. Blair countered by offering her own appeal, "She's so pretty, and so nice... I've loved just talking to her," she said.

Rick just listened as she spoke. Knowing Rick as she did, Blair knew that he had every intention of getting naked with Cassandra that night. The realization hit her like a wave, and she felt like a child being told that playtime was over. He ended his short speech and they stared at one another. Then just as quickly the look on Rick's face changed. He glanced away and then back to Blair. She saw compassion and in some way an appreciate for her situation.

Then, before either of them could speak again, his eyes shifted to her left, and she turned to see Cassandra briskly walking toward the two of them. Enthusiastically, she announced, "I'm going back to my rental. It's a cool little condo over in East End."

She placed some cash on the bar along with a napkin on top, an address scribbled on it. "This should cover my tab, and here's the address. I'd really love it if you both came over to hang out tonight. You're both so fun, and so cute! See ya later!"

Cassandra served up another flash of her gorgeous smile, then turned and almost pranced to the parking lot. Blair read the napkin together with Rick. They looked at each other without saying a word.

The rest of their shift, including closeup tasks, were spent in awkward silence. Blair was lost in thought of whether to accept Cassandra's invitation, and face a competition with Rick for her affections, or just ignore it and go home. She was offended that Cassandra had been coming on to them both, but also faulted herself for having been so easily captivated and not aware enough to notice.

Either way, the situation left her uneasy. Her instincts were telling her to stay the hell away. But her attraction to Cassandra would not release her.

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Saturday, After Closing Time - RICK

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Rick's brain was in hyper drive as he started the simple two-stroke engine and took off. So maybe he wouldn't actually have to concede, he thought. Were they both going to fuck around with Cassandra? Would Blair even show up?

Since Blair was gay, a threesome was definitely not happening, although she was hot in Rick's mind. If anything, he considered her even more attractive than Cassandra. Blair's toned body, built from her steadfast commitment to exercise, was always on display in a tank top or tight t shirt. Blocking that impossibility from his mind, he paused at the first intersection past the parking lot. Straight ahead and up the hill was home. Turn right, East End and Cassandra were awaiting him.

He paused for a moment, considered it all, then turned on his blinker.

Ten minutes later, without speeding, he arrived at the location he'd read on the napkin. He dropped the kickstand on his scooter just as Blair pulled up in her older VW Beetle. "Damn. She came," he said out loud to no one in particular. He might have simply hurried to the door, but given that Blair had already spotted him, he waited out of respect.

Rick and Blair sized one another up as she exited her car. He noticed that she'd somehow changed her top in the past few minutes, and was now wearing a floral blouse with her jeans. "She took time to dress up, at least by island standards," he thought.

"Rick, How's this going to work?" She asked as she approached, her normal, confident tone still missing.

Rick just shrugged and held his hands out, in no way certain how to handle the situation, or Blair's involvement. In his mind, he had been invited to the bed of a sexy woman, one that he was seriously ready to fuck. But here was his coworker, and de facto boss, also invited for what was clearly the same experience. "What the fuck...," he shook his head and mumbled.

"Yeah. What the fuck is right," she replied. Rick could sense her nervousness. "Seriously, what are we going to do here, take turns? Pass her around?" Blair shook her head as she continued, "I really like this girl, Rick. She's sweet. She's carefree... and she likes me too. I understand why you're here, for a piece of ass. Which is fine, you do you, asshole. But I didn't come here for a threesome." Blair's expression cried out for reassurance if nothing else.

"I don't know what's going to happen in there either, but It'll be ok." Rick offered. "Yeah, I'd like to fuck her. But I've got your back, Blair. Nobody's going to make you do anything you don't want to." Then the two of them, committed as they were, walked up the steps together. Rick watched as Blair cautiously knocked on the door.

The door opened and there was Cassandra, beaming her same bright smile, wearing only yellow boy shorts and sports bra. "Yay! You both came!... This is so awesome!" She giggled as she stepped out to hug Rick and Blair with both arms around their necks simultaneously. "Come on! Let's have some fun!" she said as she turned and pseudo-skipped into the house. Rick and Blair exchanged a shared, uncertain look as they entered the condo and closed the door behind them.

Cassandra was into the first floor bedroom in an instant, not looking back, obviously expecting them to follow her. Blair entered first and was immediately embraced by Cassandra, her arms wrapping around Blair's torso and caressing her. Blair melted into her, hands touching her waist, their mouths and tongues dancing and teasing. Rick could see Blair's shoulders rise and fall as her breath quickened. It was both intriguing and comforting to see his stern coworker show a little passion.

Cassandra broke off their kiss, and turned to Rick. With greater enthusiasm, she came for him, reaching behind his neck to pull his mouth down to meet hers. Eyes closed, he felt a rush of energy as her tongue dove deep into his mouth, taking charge of their kiss and pressing her lips forcefully against his. Rick cracked open his eyes and noticed Blair, observing their embrace, albeit in a less than approving way, judging from her body language.

Cassandra released Rick, turned and dove headfirst onto the bed, landing on her stomach and gracefully flipping onto her back. She looked to the two of them, bent her knees and spread her feet apart, inviting them to join her with a view of the prize that awaited between her legs. "Come on, guys. Let's fuck the shit out of each other!" Rick knew exactly what to do next, but held back, wanting to observe Blair and how this might all play out.

Cassandra, oblivious to anything but her own excited anticipation, waited impatiently.

Blair looked to Rick as if she might burst into tears. She appeared somewhere between panic and embarrassment, frozen, her glance shifting between Cassandra and him. It pulled his attention away from Cassandra and her waiting pussy as he took a step towards Blair and took her hand. "It's OK." He said quietly. He smiled warmly, paused, then continued, " It's going to be OK, Blair." He motioned toward the bed. "Go ahead. Just you and her."

Blair, silently mouthed "Thank you" to him. Visibly relieved, she knelt, then crawled forward on the bed, up and on top of Cassandra and kissed her softly.

Rick took a place on the edge of the bed and watched in silence as Blair and Cassandra kissed in a way that reunited lovers might embrace, taking time to explore one another, stop to make eye contact, to smile and kiss again. Blair sat up and removed her blouse and bra, revealing her perfect, athletic frame. Rick had seen and appreciated the detailed and elaborate tattoos on her arms, but did not know that her breasts, stomach and back were adorned with extensive, and beautiful art as well. He was surprised and aroused by the sensual beauty underneath her tough exterior.

Soon Cassandra's undergarments had been removed, and Blair began kissing the entirety of her body, starting with her toes, up her legs, teasing across her shaved pussy, up her torso and finally letting her mouth wander aimlessly around her breasts and nipples. Cassandra writhed with delight, seemingly oblivious to Rick's presence.

It was a new experience for him, witnessing such an encounter as only a spectator. He was struck by the deep and instant chemistry between these two women; by the calm, patient way in which they explored and reveled in each other's bodies.

Blair slid downward, her mouth exploring the flesh between Cassandra's legs. Rick observed how slowly and purposefully she licked and kissed all around her bare pussy, putting off for an eternity the moment when her lips would finally find her prize. He was humbled as he watched, and considered his own, practiced methods of eating pussy as crude, almost comical in comparison. He'd presumed himself a skilled lover. But watching them, he felt more like an amateur.

As Blair licked and sucked her button, a finger deep inside her cavern, Cassandra rocked her hips up, offering more of herself. She spread her legs, inviting Blair deeper inside her. Soon her body tensed, she whimpered as she came, waves of pleasure rippling across her body. She twitched and gasped, as a string of soft cries filled the room as the waves diminished and passed over her. Blair's mouth again found Cassandra's, as they kissed and caressed one other, their affection seemingly to grow as they did.

Like her new lover, Blair appeared oblivious to Rick's presence. She made no eye contact with him as she removed her jeans and panties in a swift, combined action. Now naked, she slithered her way up the length of Cassandra's relaxed body, continuing higher, until she was poised above cassandra, pussy hovering over Cassandra's mouth. She raised her head slightly, her lips touching Blair's pussy.

Rick grew more aroused watching the toned muscles of Blair's butt flex as she rubbed herself against Cassandra's lips and tongue. He couldn't see it from his angle, but could hear licking, sucking, along with Blair's moans and words, "Yes... Yes.....Ohhh.... Yes," her familiar tone of authority returning. He watched as Blair reached down to pull Cassandra's head up, hard against her cunt, grinding against her mouth. "That's the Blair I know," Rick thought.

Cassandra, reasserting control, pushed her lover up and told her to lie down on her back. "I'm going to eat your pussy my way, sweetheart," she instructed. Blair complied silently, a look of expectation and submission blended together on her face. She lie back, head propped on a pillow, watching as Cassandra kissed up the insides of her legs, around her belly, then pushing Blair's legs up and apart, licking her ass, her tongue gliding up to the already wet flesh of her untrimmed pussy. Then back down and teasing her ass.

Her lips surrounded Blair's clit...sucking...licking, as she pushed Blair's legs forcefully, farther up and apart. As Cassandra's tongue lapped wildly on her, Blair's passion rose, a welcome crescendo rising deep within her until she tilted her head back and screamed in ecstasy. Her roar filled the room as her body clenched and strained, muscles flexed and frozen.

Rick was astonished. He'd brought women to orgasm and had also witnessed plenty of what he was certain had been faked orgasms. But he didn't know such a physical reaction to sexual pleasure was even possible. As he saw Blair begin to relax, he realized he'd been holding his breath, and sucked in a huge gulp of air.

While Blair was still in her own world, lost in post orgasm delirium, Cassandra noticed Rick and reached to take his leg. "Hey gorgeous, feeling left out?" she said. "Let's do you, baby." She disengaged from Blair and moved to lift Rick's t shirt up and off. "Lie down, baby. We've got to get you naked. I want to see that cock you have inside there."

Rick lie down next to Blair, arm touching arm. She scooted slightly to the side, and Rick was uncertain if she did so to make room, or simply to avoid the close contact. Cassandra removed his shorts and boxers and gleamed excitedly at Rick's erect cock before her. She took him in her hand, and without hesitation, buried her face into his loins, engulfing his erection.

Rick watched as Cassandra's head bobbed steadily up and down on him, slurping sounds mixing with the approving "mmmm's" she was making. She stroked his balls while she licked slowly up and down the length of his shaft, enjoying his lustful gaze as she did. He noticed Blair's breathing next to him, her face next to his shoulder, her hand resting on his chest. Cassandra reached for Blair, touching her arm. "Come on. Kiss him, baby. He needs us both."

Blair hesitated. She looked to Cassandra, who stopped what she was doing, confused by the pause, then to Rick, who offered her a comforting smile and brought his arm to the back of her shoulder, inviting her to him. Then she leaned over, her lips finding his, and closed her eyes. Their embrace finally commenced, Cassandra returned to her worship of Rick's rigid cock.

Her apprehension dissolving, Blair kissed him more assertively, her hand caressing his face, as Rick became lost in arousal, lifting his hips up, pushing his cock into Cassandra's mouth. He was moaning into Blair's mouth as her lips and tongue ravaged him. Rick had never been in a threesome, so had few pre-conceived ideas of what to expect, other than twice the sex in his testosterone laden mind. As it happened, the combination of their attention overwhelmed his senses. Yes, it was twice the sex, so to speak, but the electricity flowing between the three of them was so much greater.

Blair interrupted the dynamic as she broke off their kiss, putting her hand to Cassandra's forehead. "I want you... I want you inside me, Rick," she said to him.

Cassandra silently acknowledged and moved back. Blair responded by straddling him, the slick folds of her pussy resting against his aching cock. Knees spread, her body upright, she ground her pussy against him, his shaft pressing against her, his swollen head touching her clit. Rick felt Cassandra's hand from below, caressing his balls, then gripping his cock as Blair lifted herself up. Cassandra rubbed his tip around the lips of her pussy, until Blair could wait no longer, and lowered herself down, Rick's erection penetrating deep inside of her.