One Night Of Sindi

"Buy a lady a drink?"

Jack looked up from his beer to find the owner of the sultry voice; a beautiful young black woman in a short, skin tight white dress.

Her dark eyes regarded him with a not so subtle invitation. Her smile was warm, and highly suggestive.

It wasn't his first rodeo with these kinds of offers. He'd been attending this business conference annually for several years now, and there were always women like this one in the hotel bars, looking for lonely, bored attendees who might want some female companionship.

For a price, of course.

"And what does buying you a drink do for me?"

Her smile never faltered. "Well, some conversation to start. The rest we can negotiate along the way."

Jack sighed wearily. "Look, I don't wish to appear rude. It's not that I disapprove. But this really isn't my kind of thing. And even if I were tempted, and believe me when I say you certainly are tempting, I can't really afford your...services."

"I see."

Jack expected that to be the end of it; that she would move on and look for another target. The bar was certainly filled with plenty of other men.

To his surprise, though, the alluring, dark skinned woman instead eased herself onto the stool beside him. "I understand that, and I appreciate your honesty. But tell you what; buy me that drink and give me five minutes of your time. I have an offer that might change your mind."

Jack drained the last of his beer while he considered. She was most definitely a beauty; curves in all the right places and full, pouty lips that quickened his pulse as he imagined them doing naughty things to him.

Besides, he was bored. What harm could there be in indulging her for one drink? It had been quite awhile since he'd spent any time with a woman, let alone one as young and sexy.

"Sure," he shrugged. "Why not?"

Jack waved the bartender over. "Another beer for me, please, and..." He gestured to her, silently inviting her to order.

"A vodka and cranberry, please."

With a nod, the bartender went off to fetch the drinks.

Jack took a moment to look her over again. Her long shapely legs crossed in such a way that had her already short dress riding up to expose just a hint of well rounded ass. Leaning slightly forward on the bar, her cleavage was on full display, a lovely contrast of ample ebony flesh beneath the sheer white dress. She knew her assets, and wasn't shy about flaunting them.

Her soft brown eyes twinkled mischievously in the dim light, and when she batted them at him, Jack found himself wondering just how much money he had in his bank account, and what bill he might be able to skip paying this month.

"What's your name, hun?"

Her question stirred him out of his reverie. "Huh? Oh, sorry. Jack."

"Nice to meet you, Jack. I'm Sindi. With an S."

Jack had to chuckle. "Of course you are. Well, nice to meet you too, Sindi with an S."

The bartender returned with their drinks, and Sindi extended her glass. "Thanks, Jack. Cheers."

After a sip of their drinks, Jack asked, "So, I take it you're not a local, just in town for the convention?"

Sindi was surprised. "How did you know?"

"The accent. Northeast, right? New York? Jersey, maybe?"

Sindi laughed softly. "You're very observant, Jack. Yes, I was born in Queens. Currently living in North Jersey."

"Small world," Jack grinned. "Born in South Jersey, but moved to Philly a few years ago."

"Wow. Practically neighbors."

A moment of silence passed as they drank. It was Sindi who broke it this time. "So, I promised an offer; let me explain:

"As you've already guessed, I traveled out here from the east coast for the convention. Normally, when I do this kind of thing, I reserve my own hotel room. This time though, I'd already booked a client in advance. He wanted me for the whole weekend. Had his own room already, and I was supposed to stay with him.

"I met up with him last night, spent the night of course. But today, out of the blue, his wife showed up. Things got... ugly. I got out of there quickly."

"Oh, geez," Jack interjected. "That must have been a mess."

"It was," Sindi nodded. "But, on the upside, my client had already paid for everything in advance, including my travel costs. So I got my money.

"Problem is, my flight home isn't until tomorrow, and I have no place to stay tonight. All the hotels are filled up, of course."

"Ah, I get it now," said Jack. "This is where I come in. You were hoping to find another client staying in a hotel and get an overnight out of it."

"Yes," Sindi confirmed. "So my offer to you is quite simple. Let me stay in your room, and in exchange, you get access to my services for the night. Anything you want."

Jack took a long pull on his beer as he thought it over. It felt too good to be true. "Why me? What's the catch?"

"I don't understand."

Summoning his nerve, he faced her directly. "Look, you have to see this from my perspective. This bar is full of younger, way better looking guys, probably with a lot more money than me. You could easily find one more than willing to pay for your services and still get a place to stay out of it too. So why make this offer to an old, average looking dude who's already told you he can't afford you? You could have just moved on, found a guy with a bigger wallet."

"I suppose you're right," Sindi acknowledged. "But, and this might surprise you; it's not always about money. Sure, I could have spent the next hour or two scouring the bar, flirting and soliciting the patrons. But what if I couldn't find someone willing to pay my usual rates for an overnight? I'd be stuck with no room. Besides, I already got paid full price for the weekend, so I don't need the money, just the room."

Jack looked skeptical. "Yeah, but if that's the case, you probably could have just gone to any guy here and offered to hook up with them. I'm sure somebody here would have taken you up on a One Nighter."

"True. But isn't that what I've done with you? Offered you one night? Just been more honest about my reasons?"

"I guess. But again I have to ask; why me? There's guys here far closer to your age than me, and way better looking. So why did you pick me?"

Sindi sighed. "You want an honest answer? Because I prefer older men in my line of work. Young guys are too cocky. Or too disrespectful. They see 'hooker' and think it gives them carte blanche to treat me like a piece of meat.

"Older men are more respectful; they treat me right. They aren't overly demanding. And they're not trying to renegotiate prices in the middle of things."

"I see your point there," said Jack, "but if you're offering a freebie anyway, why not pick a younger, better looking guy?"

Sindi took his hand. "Jack, you're way too hard on yourself. You're more handsome than you give yourself credit for. Think about it; given my situation, do you honestly think I'd choose a guy I found physically repulsive to make this offer to? I may be a sex worker, but I'm still selective. I screen my clients. I'm not super picky, of course. But if I can't find something interesting or attractive about them, I don't take them on as a client.

"I have sex for money, yes. But I don't just fuck anyone. I choose who. I choose when. And I chose you."

"I still don't understand. Why?"

"Jack, I sat in this bar for over an hour before I approached you. You never noticed me, because you never once looked up from your drink. You looked bored. You looked stressed. But most of all, you looked lonely."

"Ah," Jack grimaced. "Lonely old guy alone at the bar, so, you figured you'd offer me a pity fuck? Is that it?"

"Not at all." Sindi looked perturbed. "Look, I can just move on, if that's what you really want. Because you're right, I can probably find someone else. But you asked, I answered. I need a place to stay. And while I usually get paid for sex, I also really enjoy it.

"You looked like you could use some company. I thought you might actually enjoy the offer; a chance to spend the night with me, no strings, no charge. I'm good at what I do, Jack, and I meant it when I said 'anything you want.' So, what do you say? Are you interested? Because it's getting late and I need to know if I'm still looking for other options."

Jack swirled his beer in the glass as he contemplated her words. And her offer.

Finally, he turned to her with an embarrassed smile. "Look, I'm sorry. I didn't mean to be an asshole about it. And I really appreciate your honest answer."

He took another gulp of his beer. "This is without a doubt the craziest thing to ever happen to me. But okay, I accept your offer."

Sindi smiled, her face once again warm, kind and alluring. "Good. You won't regret it, Jack, I promise. Now, tell you what, buy me one more drink, and maybe some snacks, I'm starving."

Her hand landed on his thigh, very close to his already stirring cock. "We can sit here a little while longer, chat, drink, no rush. Then, when we're ready..."

Her hand slid up, cupping his bulge. "...we can go upstairs and have ourselves some fun."

🍹🍺🍽

After retrieving the suitcase she'd checked earlier with the hotel concierge after a flirty smile and generous tip, Sindi and Jack went up to his room.

"Mind if I take a shower?" Sindi asked. "Been a long day. I wanna freshen up a bit."

"Of course," said Jack. Then, after a nervous pause, "Um, mind if I, um, join you?"

Sindi slipped into his arms; his hands found the small of her back. "Maybe later, hun," she purred softly in his ear, "after we've had our fun. But let me have some privacy this time, okay?"

Her lips found his earlobe and nibbled it gently. "It'll be worth the wait, trust me."

"Of course. No problem." Jack reluctantly let go of her.

With a sexy smile, Sindi carried her bag into the bathroom, closing the door behind her.

She paused there for a moment, taking a deep breath. She'd been doing this for several years now, but never under circumstances like this. While she'd felt comfortable with Jack in the bar, there were always those deep seated fears that would crop up whenever she was alone with someone new for the first time.

She looked at herself in the mirror. "You sure about this, Cynthia?" she asked herself. "Because if you're not, you can always just catch an Uber to the airport and sleep in the terminal."

Shaking her head, she laughed inwardly. "Yeah, like you really wanna do that. Just chill. You've done this a million times. Trust your gut. He's been nothing but a gentleman so far. Just relax and show him a good time."

Peeling off her dress, she admired herself in the mirror. Despite her nerves at the moment, her arousal was obvious. Her dark brown nipples were swollen and hard, her chocolate skin awash with goosebumps.

She couldn't wait to show this stranger her body, to watch his desire for her grow, to fuel his passion, stroke the flames of his lust, to make him crazy with it.

Because she got off on that. Always had.

But first, the shower. Sindi tucked her hair carefully under her shower cap before turning on the water, adjusting the temperature, and slipping under the warm spray.

🛁🧼💄

Jack sat on the bed, heart and mind both racing a mile a minute. He was still dressed except for his shoes and socks. He'd briefly considered undressing completely, but decided that would be rushing things. Plus,he still felt somewhat self conscious about his body and figured he'd wait to get naked til the lights were down low.

Not that he was in terrible shape, of course. For his age, his weight was moderate, and he wasn't completely out of shape.

While his chest hair had gone gray, the hair on his head was still a full and lustrous dirty blonde. The fact that it wasn't thinning or balding yet was also a plus, and many people he'd met at the conference thought he was younger than he was.

Still, he worried, although he couldn't rationalize why. Even if she was lying about finding him attractive, just playing to his ego, it didn't really matter, did it? She wasn't a potential girlfriend, someone he might wish to form a long term relationship with. This was a one night thing. He'd probably never see her again. So what difference did it make what she thought of his looks, really?

His thoughts were interrupted as the bathroom door opened. Sindi stepped out, wrapped in a hotel towel. Approaching the bed, she stood before him and, flashing that alluring smile, dropped the towel to the floor.

What he saw took his breath away.

Her long, dark hair flowed in waves around her oval face. Her makeup was tasteful, smokey mascara highlighting her dark brown eyes, adorned with long, thick lashes. A dark cherry lipstick made her already full lips pop still more.

Her body was a masterpiece. Her breasts stood firm and proud beneath the sheer fishnet top. Her bare stomach was flat, smoothed and toned, with well defined abs that drew his eyes lower, to the matching fishnet thong that covered her hairless mound.

Her dark chocolate skin glowed with a silky sheen, and he could already smell the sweet coconut scent of the lotion she must have used to oil up her body in the bathroom.

Spinning around, she bent forward, showing off her full round booty, shapely cheeks curving down and meeting at the bottom, with a hint of the puffy folds of her vulva just below.

Turning back to him, she cocked her head coyly. "So, what do you think?"

"You're... you're stunning."

"Why, thank you, Jack." Sindi moved to the bed, gliding her way over him. In moments they were face to face, her hair tickling his neck as their lips met, his hands moving to her hips, pulling her to him.

She took the hint and started to grind on his lap as they continued the kiss. His hands felt good on her as they traveled along her lower back, ass, and thighs. His touch was strong but gentle, and he trembled when his fingers brushed the edges of her cleft, her pulse quickening.

She needed to feel his skin. Long, perfectly manicured fingers undid the buttons to his navy blue shirt, revealing wiry tufts of chest hair.

Sindi found his pecs, squeezing them before moving her hands to his broad shoulders, pulling the shirt away, helping him shrug it off.

Sindi continued to hump herself against his lap, but to her surprise, Jack wasn't reciprocating. His hands had been busy, yes, exploring her curves and exposed skin, but he lay strangely still beneath her.

She decided to encourage him, and her hands moved quickly to the clasp of his trousers. She tugged them down and off, but when she next reached for his boxers, Jack stopped her. "Wait, just... wait."

Sindi was surprised. "What's wrong, hun?"

Jack flushed a deep red. He avoided her eyes. "Maybe... maybe this isn't such a good idea."

"What do you mean? I thought you wanted this."

"I did. I do. It's just..."

"Just tell me, hun."

With a frustrated sigh, Jack finally spit it out. "It's been a long time. I'm nervous. And... fuck, this is embarrassing, but my... body... isn't... cooperating."

To Jack's surprise, Sindi offered a relieved smile. "Ah. Is that all? I thought it was something serious."

Jack was taken aback. "Pretty serious to me!"

Sindi stroked his chest as she responded. "I'm sorry, that came out wrong. What I meant to say was this isn't that big a deal. You're not the first guy I've been with that had... performance anxiety. It's okay, hun. Just relax. We're in no rush here. You're stuck with me the whole night, remember?"

Jack had to chuckle. "I suppose I am, aren't I? A deal is a deal, after all."

"It is." Sindi's breath was warm on his neck. "So let's just lay here, relax, take a moment. Just... be."

Resting her head on his shoulder, Sindi snuggled close into him, laying an arm across his stomach, intertwining her legs with his. Jack wrapped an arm around her, rubbing her back as they lay together in silence.

"So, how long were you married, Jack?" Sindi finally spoke.

"How'd you know?"

"You're not the only one good at observing people," Sindi smirked. "I've done this before, remember? And I've gotten pretty good at reading men. And most of them have the same story."

"I suppose we do," Jack sighed. "We were married nineteen years. The divorce was finalized four months before our twentieth anniversary. But the sex life had evaporated long before that. At least for me it had. Found out eventually she'd been cheating on me with a guy half my age. That ended things pretty quick."

"I'm sorry," Sindi offered.

"Don't be," Jack shrugged. "It sucked, but I'm glad to be free of her."

"So, no girlfriends since?"

"No. It's been... tough. Getting back out there. Trying to meet people is so much harder these days. And don't even get me started about online dating."

"Oh, trust me, I get it." Sindi continued to rub his chest for a few moments, then sat up to meet his eyes. "I have an idea, if you're interested. Would you like a massage? It would help relax you."

Sindi was encouraged when he didn't hesitate. "Sure. That sounds wonderful."

Jumping up, Sindi retrieved a bottle from her bag. "You'll like this lotion, soft and silky but not too greasy, won't leave a mess all over the bedspread."

Returning to the bed, Sindi knelt beside him. "I know you're still a little nervous, but if you're comfortable enough, we should probably remove your boxers."

"Um, sure." Blushing, Jack lifted his hips as Sindi pulled his underwear down and off. While still not erect, Sindi was heartened by its plumpness. It wouldn't take much to coax it to its full potential.

But she was in no rush. "Roll over."

Jack flipped to his stomach and Sindi straddled his legs. Squirting a healthy dollop of lotion into her hand, she rubbed it into her palms, warming it, before moving to Jack's body.

While most clients wanted an "erotic" massage, Sindi was also well versed in actual techniques to help work out the tension in muscles and fully relax them. And so she firmly kneaded his shoulders, his deltoids and lats, working her way down to the small of his back and then, of course, his glutes.

Jack groaned happily at her efforts. Sindi moved to his inner thighs, working them with her fingers, "accidentally" brushing along his testicles several times.

Her thumbs found his perineum, and pushed down with gentle pressure. His body jumped involuntarily. "Jesus Christ!" There was no objection in his exclamation, only surprise and apparent pleasure.

"You like that?"

"Fuck yes!"

Sindi continued with her thumbs, working them in very small circles in opposite directions while steadily pressing and relaxing over the sensitive spot.

His hips swayed with her movements. She felt something twitching beneath her fingers and knew he was ready.

"Turn over."

Jack obeyed immediately and Sindi met his fully aroused cock for the first time. "Oh my, that's lovely hun."

Jack looked both proud and doubtful. "I bet you say that to all your clients."

"I do," Sindi admitted. Reaching down between her legs, her fingers explored her slick folds for a moment before reaching out and holding her fingers to his face. "But I only gush like this when I mean it, Jack. See how wet I am? Can't fake that, hun."

Jack sniffed at her fingers eagerly. "Ohmygod, you smell incredible!"

"Ah," Sindi thought, "he's got a scent fetish. This will be easier than I thought."

Out loud, she responded, "I'm glad you like it, hun. Want a better sniff?"

His eyes lit up with understanding as she moved forward, now just over his face, her sex mere inches from his nose. Pulling aside the fishnet panties, she parted her folds with two fingers. A sheen of thick white cream hung between them.

Jack licked his lips hungrily. Sindi knew what he wanted, but decided to tease him just a little more first. Rocking above him, she spread herself wider, exposing her engorged clit as well as the opening to her dark pink insides.