"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?"
