Naani's Retirement Party

On the surface it felt like any other Wednesday as Kai entered the office where he worked. The same bored-looking receptionist barely managing a "Hello", the same crowded elevator ride to the fifth floor, the same twenty steps to his cubicle. The same scrolling through his work emails and preparing for the day of cold calls and following up on leads. However, Kai knew this day was different. In fact, the whole week was and would be different.

See, his supervisor, Naani, had announced her early retirement from the nonprofit where they worked earlier in the month, and this week would be her last. Though barely fifty years old, through hard work, smart investments, and financial help from her eight siblings, she had bought a two-family house in Connecticut and would be moving there to be closer to her daughter, son-in-law, and two grandchildren. Her last day would be Friday, and everyone in the office would be gathering at a midtown lounge that evening to give her a proper send-off.

Because of the hours he worked in and out of the office, Kai rarely got to go out anymore, which is hell for a 26-year-old who loved to party and missed the days when he and his friends had, in his mind, legendary nights out on the town. It would even be worth being in the same building with David, who was already acting as if Naani's job was his, if he could just get out of the house for once. Not even David could ruin such a party, though not for lack of trying; the man was arrogant, obnoxious, and completely oblivious to the apathy he elicited from everyone around him. Kai liked everyone else in the office a lot, and he was actually sad and somewhat anxious to see Naani go - since she hired him fresh out of college four years before, she proved to be a fair and patient boss, teaching him the ropes of achieving the corporation's stated mission and having a passion for the work, which he found infectious. She was the consummate professional, from her hair to her form-fitting pantsuits down to her heels (or flats, if she expected to be out in the field). To go from working for her to a useless lump like David was making Kai seriously consider looking for work elsewhere.

Kai stepped off the elevator to see Naani and David walking away from each other, evidently having just finished a conversation. As David walked toward his cubicle, he glanced at Kai, barely hiding a sneer and checking his watch, as if he expected to find that Kai was late. Which is stupid, Kai thought to himself. As a rule, Kai always tried to arrive at 8:20 am, ten minutes early. He hated being late and prided himself on his punctuality. He grunted a greeting at David and gave Naani a considerably warmer "Good morning" before sitting down at his cubicle and starting the day.

After an hour, Kai looked up from his computer to see Naani walking towards him from her office. Today, her suit was navy blue with white pinstripes and her greying hair was braided into a crown. The frames of her glasses matched her black pumps. Naani's dark brown skin matched Kai's own, and her face was freckled with small moles, as if someone had sprinkled pepper on it. Kai straightened up in his chair, expecting her to ask him something important and work-related.

"Hey, Kai," she said in a low voice with a pronounced Trinidadian accent, "you know my retirement party is Friday, right?"

"Yeah, I'm looking forward to it," Kai replied. Naani smiled.

"Good." She touched him on the arm, something she'd been doing with increasing frequency lately. "Hopefully I don't get too tired trying to keep up with you young people." Kai chuckled despite himself, and Naani laughed as well.

"I'll try to go easy on you. Promise," Kai said. At this, Naani's smile froze, her eyes flickering around the room, then she cleared her throat.

"Thanks. The reports look good. We'll discuss it more later," Naani said, turning on her heel and returning to her office.

Kai looked after her, wondering if it was just his imagination or his soon-to-be-retired boss really was putting an extra switch in her walk. He didn't normally go for older women, but it was clear that Naani was a real knockout when she was his age, and even now took care of herself; she had a slim build and her curves were well-proportioned. If not for the streaks of grey she proudly displayed in her hair, she could have passed for thirty-five. At times, he thought of her like an older sister, or even a mother or an aunt. Lately, though, he was increasingly seeing her as a woman, and a good-looking one at that. It was too bad; if she wasn't his boss, and they were closer in age, and she wasn't about to move away, who knows what might have happened between them?

After the end of his workday on Friday, Kai hurried home to shower and change before going to the lounge. Checking himself in the mirror - and admiring his outfit, a black slim fit suit with matching loafers and a powder blue shirt - Kai took an Uber to meet his coworkers and say goodbye to Naani. Entering the lounge and passing the bar, he was glad to see that the woman of the hour was not hard to find; she was sitting in the middle of the reserved booth in the rear area, the literal center of attention. She was chatting happily with well-wishers and mixing herself a drink from the bottle service. He had never seen her so relaxed, so happy, so... attractive. Naani was wearing a knee-length leopard print dress with spaghetti straps, black stiletto ankle boots, and had let her braid out into a loose afro. Gone were the glasses Kai knew so well; either she didn't need them that badly, or she was wearing contacts. Her makeup was flawless, the red lipstick complimenting her chocolate-brown complexion. Kai waved as he approached. She saw him and waved back, yelling "Hi!" over the loud music. She put down her drink and stood up, throwing her arms wide open for a hug and beaming at him. They had to lean towards each other to embrace over the table, and Kai couldn't help but inhale her perfume deeply. He'd never been this close to her before, never noticed how soft and warm her skin was, how toned her body was. A coworker fortunately chose this moment to relinquish her seat next to Naani to get up and dance. Kai immediately came around the table and slid in next to her. She leaned over until her lips were practically touching his ear. He barely managed to suppress a tingle at their closeness.

"So glad you could make it," she said.

"Wouldn't miss it for the world," Kai answered. As the night wore on and the two drank, talked, laughed, he began to see her in a new light. He could no longer see Naani as just his boss, but for what she also was: a beautiful, desirable woman. She was kind, funny, easy to talk to, and hardworking. He would definitely miss her. Why couldn't he see what she truly was before? Life was so unfair.

A loud, drunken greeting broke Kai out of his reverie. David had appeared in front of them, clutching what was clearly not his first bottle of beer of the night, given how unsteady he was on his feet. Naani stood and greeted him with a hug as well, though it was considerably shorter than the one she gave Kai. David was clearly engaging in a one-sided conversation, with Naani contributing little besides nods and polite smiles. Finally, he said something that caused her to playfully smack him on the arm and send him away with a laugh. She sat back down and returned her attention to Kai.

He must have looked jealously curious than he thought he did, because she leaned toward him and said, "You know that fool David thinks he's getting my job when I leave? Joke's on him; the president is already bringing in someone from California to take over on Monday. Then he told me I look good and I should go home with him tonight!" She sucked her teeth in disgust and gave a short, harsh laugh. "He can't have my job or me!"

"I'd have a better chance of having you tonight," Kai said before he could stop himself. How many drinks had he had? To his surprise, Naani didn't look the least bit offended, but laughed again, much more warmly this time. She regarded him for a moment, then leaned in to speak.

"You know what? You're right," she said, her voice dropping to a subtle purr over the music. "But you don't want some old lady like me."

Under normal circumstances, Naani would have probably been right, but whether it was due to his tipsy state, or the fact that he knew he would never see her again, Kai had decided to throw caution to the wind. After all, even if she was inclined to, she could hardly fire him for sexual harassment, could she?

He put his hand on her knee and asked, "You're not old. And even if you were, what makes you think I don't want you?"

Her eyes widened in shock before she leaned closer to him, her smile broadening. "What makes you think you can handle me?"

"There's only one way to find out, isn't there?"

Naani's eyebrows rose and she began to answer, but seemed lost for words. She was silent for a moment. Finally, she asked, "Are we really doing this?"

Now sure that they were both on the same page, Kai seized the moment. "Yes, if you want us to. I can call an Uber and we can leave right now." As he spoke, he reached into his pocket for his phone and began to order their ride.

Remembering Kai had roommates, Naani placed a hand on his forearm to stop him. "Let me."

Minutes later, on pretense of being tired, Naani had extracted herself from the gathering and was entering the car, an anxious Kai following close behind. Once seated, they stared at each other for what seemed like forever. Finally, they came together, and their lips met. As the kiss deepened, their hands desperately explored every inch of each other, frustrated by their current state of dress and the knowledge that the driver was surely stealing judgmental glances at them through the rearview mirror.

Finally, Naani broke the kiss and spent the rest of the ride caressing Kai's chest and resting her head on his shoulder, while he wrapped an arm around her and gripped her ass. Once, feeling particularly bold, she let her hand slip down to his lap, running her hand down to his knee and over his inner thigh on the way back up. She let out a small gasp of surprise as she realized her delicate fingers were touching his bulging arousal.

As if burned, she began to jerk her hand back, but Kai caught her wrist and held it there with a gentle, yet firm grip. Naani looked up at him with overwhelming anticipation, her impatient body now fidgeting and squirming. He responded by kissing her softly and probing her mouth with his tongue. He released her hand and pinched and tugged at a nipple through her dress. She inhaled sharply and moaned into his mouth, her nails digging into his shaft.

After an interminable car ride, they arrived outside the brightly-lit courtyard of an apartment building. Judging by the lights seen through the windows, only a handful of tenants were awake at this late hour. No one was loitering on the grounds; in fact, the street was practically empty other than a passing jogger and an old man walking his dog. Manicured grass and well-tended flower beds spoke of money - or, at least, more money than Kai was making. It must be nice to be the boss, he thought. He heard Naani thank the driver as she maneuvered to get out of the car. He held out his hand to help her, and she took it. He closed the door and barely had time to watch the car drive away in search of its next fare when he felt Naani, still holding his hand, pull him towards the front door, past the vestibule, and into the elevator.

In one fluid motion, she pressed the button for her floor and leaned into his body. He took her into his arms, grateful for the privacy with which he could now explore more of her with his hands and mouth. A thrill went up Naani's spine as she felt his lips and tongue on her face, neck, shoulders, arms, and chest, and his hands groping everywhere he could reach; she couldn't remember the last time she felt so desired and desirable. She responded in kind, gripping the back of his head with one hand and rubbing his crotch with the other. It seemed to have gotten bigger and harder since the car ride, and her juices flowed even more freely imagining what pleasures awaited her once she got him home. Still kissing her, he backed her out of the elevator as the doors opened. Even though her apartment was, thankfully, only a few feet away, it was all Kai could do to restrain himself and let her unlock the door.

A strong scent of flowers brought Kai more to his senses, and he slowly followed Naani inside her home. The walls were a shade of cream, save one lavender-colored accent wall in the living room. Pictures adorned the cream walls. Kai presumed they were of Naani and her family. On the glass-topped coffee table were two 3.5" x 5" picture frames, one of which held an old photo of Naani as a young woman in her 20s. The other picture seemed to be fairly recent and depicted a couple with two small children, twin boys. The woman was the spitting image of Naani - her daughter, obviously, thought Kai. If she aged like her mother, her husband would have no reason to complain.

So engrossed was he in his speculations, he didn't notice Naani calling him till she tapped him on the shoulder. He whirled around, startled, to see her holding an opened, half-full bottle of red wine and two glasses. She giggled and asked, clearly not for the first time, "Would you like some wine?" Kai smiled weakly, a little embarrassed. "Umm, yeah, thanks."

As she poured, she pointed her jaw towards his feet. "Shoes, please." Kai understood immediately; like many people from the Caribbean, Naani did not like guests to wear their shoes in the house. He slipped off his loafers, and his jacket soon followed. He placed his shoes neatly by the door and hung the jacket on a peg nearby. When he came back, Naani handed him his glass and invited him to sit on the couch, taking her own place next to him so closely their thighs touched. He raised his glass in thanks and drank deeply. She fixed him with an intense look, her hunger clear.

"So," Naani said after a moment, caressing his leg with her free hand. "Here we are."

"Yeah, here we are." He began to plant soft kisses on her neck, cheek, and lips. He could hear her breath grow faster and shallower from the touch of his lips on her fragrant skin. Suddenly, she stood up and walked towards the bedroom, slipping the straps of her dress off her shoulders along the way. Kai felt his heart pounding in his chest; as he rose to follow, he began to unbutton his shirt. By the time he'd finished, he was standing in the doorway and was met by the sight of Naani's dress lying on the floor, and the lady herself wearing nothing but a black lace thong.

The room was dimly lit by the streetlights outside, but even in the low illumination, Kai could tell that the effort Naani put into her figure paid off. Though age and gravity had had their way with her B-cup breasts, they didn't sag obscenely. Her stomach was lined with stretch marks from carrying her daughter all those years ago, but still flat. Her body was lean and toned, like a runner's. She had every reason to be proud of her nude form. Yet there was a hint of hesitation in her eyes, as if she was self-conscious about being so exposed in front of a much younger man, afraid Kai might mentally compare her to a woman half her age and find her wanting.

Her fears turned out be unfounded - Kai shrugged off his shirt and crossed the room towards her, eyes blazing with desire. He took her in his arms and kissed her, running his hands all over her silky skin and paying special attention to her ass. When he broke the kiss, Naani took the opportunity to explore him. She planted a trail of kisses from his neck to his collarbone, stopping briefly to lick his nipple. Kai gasped and closed his eyes as a jolt of pleasure ran up his spine - he didn't even know he was sensitive there. He barely had to register this new fact when he felt Naani's hands undoing his belt and slacks. When he opened his eyes, she was on her knees, face alight with anticipation.

"Let's see what you've got in here," she whispered as if to herself. In one swift motion, she tugged his pants and boxer briefs down around his ankles, unleashing a fully erect, eight-inch dick. She smiled and made a throaty sound of approval as she took it in her hands and slowly stroked it. Through his euphoric haze, Kai could no longer recognize the woman in front of him; she certainly looked like the kind, friendly person who'd supervised and mentored him for four years, but he never dreamed that she could or would act like some kind of sex goddess. Naani took him in her mouth and Kai's capacity for coherent thought crumbled into dust.

She sucked him with experienced gusto, mouth and hand moving in sync up and down his shaft, while her other hand gently massaged his sack, all the while fixing him with an erotic stare. Kai moaned and sighed despite himself, and when his normally-deep voice began to rise a few octaves, Naani began to slow down her efforts, and eventually released him from her mouth with an audible pop. She kissed the tip and giggled as she lifted his shaft and licked and suckled his balls, gently jerking him.

"Can't have you cumming just yet," she said as she finally stood up. "We've got all night."

Naani peeled her thong off, releasing the subtle but heady fragrance of her arousal throughout the room. Kai inhaled deeply as she crawled onto the bed and lay on her back, noting how she almost smelled... like flowers. He followed as if in a trance, parting her already splayed legs even further. He took a moment to appreciate the landing strip adorning her otherwise hairless pussy before diving in and giving her long licks from bottom to top. Naani squealed in surprise, then cooed and moaned encouragement to the younger man. He was clearly eager to please, and seemed to be paying attention to her body's reactions to his efforts; she liked that in a man. She reached down and caressed his head lovingly.

"If I knew you could suck a pussy like this, I would've taken you home a long time ago, you know," Naani said lewdly. Kai responded with a moan of his own; she tasted wonderful. A part of him wished he could do this all night. He slipped a finger inside her and focused on licking and lightly sucking her clit. Naani arched her back off the bed and squeezed one of her tits.

"Ooooh shit, that's it!" she exclaimed. "Right there... don't stop... don't stop..." She emitted another squealed, this time higher in pitch and more drawn out. Her legs quivered and tried to clamp shut around Kai's head, but he held them firmly open. He began to slowly and gently lap up her nectar as she came down from her climax, panting and grinning like the Cheshire cat. After a moment, she rolled over, propped herself up on one elbow, and began rummaging through one of her nightstands.

"Did you like that?" Kai asked with a smile of his own, already knowing the answer.

"What do you think?" Naani answered with an edge of sarcasm. "Here, put this on." She fished out a condom from the nightstand and tossed it to him. His smile widened as he tore off the gold foil wrapper and did as she asked. Hopefully there's more where this came from, he thought. They locked eyes as he climbed on top of her, and with only a moment's hesitation, pushed himself inside.

A long, drawn-out moan escaped her lips. As much as she braced herself for the first thrust, Naani was still unprepared for how full she would feel as Kai buried himself inside her. She briefly shut her eyes dreamily before a second, deeper thrust forced them back open and showed her he had only been halfway inside her. She gave a small scream as her body tensed and she clutched him tightly as a third pump bottomed him out. This was more than Naani had bargained for; she knew she hadn't been fucked in a long time, and that a young cub like Kai would be up to the task, but she thought she could handle it.