Chapter Text
“Hey, what can I get you?”
“A bourbon Manhattan would be great, thanks.”
Not what Eddie would have expected from the pocket-sized woman sitting on the other side of the bar, but ok. He pulls a bottle of Makers off the shelf behind him and stops in his tracks when she corrects him.
“Not that shit. Buffalo Trace, please.”
He turns his head and raises an eyebrow at her. A woman of good taste. It’s not an overly expensive liquor, but it’s fucking delicious. “You got it.”
Eddie puts the wax covered bottle back and grabs the Trace, pouring it into a glass with one of those big ice blocks in it, adds a few shakes of some locally made orange bitters, a splash of the good vermouth, gives it a stir, and garnishes it with a Luxardo cherry. Sliding it across the glossy bar top, he grabs the card she’s already got set out and asks, “You want to leave it open?”
She gingerly takes the glass first, holds eye contact while she takes a sip, licks her lips, and nods. “Keep it open.”
He taps the card once on the bar in acknowledgement and takes it over to the register to start her tab. He doesn’t think he’s seen her here before, but being a busy bar in Chicago, she could have been in here a thousand times and he might not have noticed. He’s been working here for a few years now, and after a while the faces all just started to blend together.
Tonight though, she has his attention. Not like that. He’s as queer as a three dollar bill, but this woman just has some kind of presence that sort of demands attention. She’s sitting alone, completely unbothered by that fact, just enjoying a fucking well made cocktail if he does say so himself, and silently watching Eddie as he works. She’s tiny. Big eyes, small frame, dressed well as far as he can tell, and has this aura of confidence that’s almost bewildering.
She asks for another after sipping the drink slowly, and Eddie gets her a fresh glass. The corner of her mouth ticks up like she appreciates that he didn’t just refill the glass she already had. As he works the bar and slings drinks left and right, he can’t help but notice her eyes on him. She’s looked him up and down with an analyzing gaze that kind of makes him feel like a piece of meat. He gets hit on by women pretty often, and Eddie is mentally preparing himself for having to tell her “sorry darling, you’re barking up the wrong tree.”
When she finishes her second drink, he makes his way over to ask if she’d like another, totally bracing himself for some kind of pickup line.
“Is this your only job?”
Ok, not at all what he thought she’d say. Furrowing his brow he tells her, “Yeah, I’m here about four nights a week.”
“And does it pay well?”
Seriously, what is going on? He can’t imagine why she would be asking him such a weird (and ok, kind of invasive) question. “It pays the bills, yeah.” Eddie gestures towards her glass. “Did you want another?”
“Have you considered going into another line of work?”
What the hell? If this lady is trying to scam him into some MLM scheme, he’s absolutely not interested. Selling leggings or candles or some shit is not appealing in the slightest. He’s trying to think of a way to kindly tell her to fuck off without screwing himself out of a tip when she leans in.
“I own a business that I think would suit you very well. You’ve got the look for it. The charm. Something my clients would definitely be interested in.”
Eddie looks her over again. She sort of oozes power, and with the cryptic way she’s propositioning him, he can’t help but be curious as to what the fuck this pint sized boss bitch does for a living. “I’m closing up in 30. Hang back and we can talk?”
She smirks at him like she already won and nods, pushing her glass back across the bar. He makes her another Manhattan and announces that it’s last call.
Once the bar is cleared out, the door locked, and the sign turned off, Eddie approaches the patron side of the bar and takes a seat next to this mystery woman. “Ok, you’ve piqued my interest. What exactly is this business of yours?”
“I own an escort service.”
Eddie immediately barks out a laugh. “Fuck off!”
She just looks at him, unimpressed.
“Fuck off. Are you serious?”
“Dead serious.”
Eddie scoffs, not quite believing that she isn’t fucking with him. “So what, you’re looking for hookers or something?”
She rolls her eyes. “I’m not a pimp. And it’s not sex work. Not unless you’d want it to be. It’s a companion agency and there’s an untapped market for gay male escorts.”
“How do you even know I’m gay?”
She raises an eyebrow at him, which…ok fine. “I clocked you the minute I sat down. Don’t play dumb with me, it’s not a good look for you. And you do look good. I can think of a handful of clients off the top of my head who you would be perfect for. And these clients? They have money. A lot of money. I don’t run some shoddy operation that’s just a cover for prostitution. This is a legit high end business, and there’s money to be made for someone like you.”
Eddie is fucking baffled. He’s just a bartender. Yeah, the bar is nice and he has to dress in black slacks and a white button up every day, so sure he looks alright. But what the fuck is this lady thinking? “What…why me?”
“You’re a good looking guy. Young. Fit, if maybe a bit on the skinny side. Might need to trim some of that hair, but the look works for you. And I’ve been watching you. You’re good with strangers. You banter well with them, listen, engage, and get good reactions out of them. You’re charming. And intuitive. Don’t think I didn’t notice how you made my drinks with the good ingredients rather than the rail shit after I asked for a better bourbon. You notice what your clients want and you make adjustments to give them just that. I really think you’d be a good fit for this line of work.”
“And uh…what exactly does this work entail?”
She smirks again like she won. “The clientele varies, but it’s usually men who are looking to have someone accompany them to events. Charity balls, galas, gallery openings. These men have class. We would just need to clean you up a bit. Get you a nice wardrobe, which would be provided for you…a little grooming. You’ve got potential.”
“Are you trying to tell me I need to chop my hair off? Because that’s non-negotiable.” He can’t believe he’s even considering this.
“Not entirely. I can tell it’s a part of your whole look. It could just stand to be cleaned up a bit. Think sort of…70’s Mick Jagger length.”
Ok. Yeah. Eddie could work with that. Jagger was a fucking fox with that shag. He could do that. Wait, is he actually considering this? “Ok, so…you’re telling me I’d just basically go on dates with rich assholes and then…what? I get paid for it? No expectations?”
“That’s exactly what I’m telling you. This is a legal business. All of the clientele is vetted, they send their requests through the agency, we find the most suitable matches for them, handle all the details of where and when, and you would just have to show up. This isn’t some back alley shit. These are classy events, or sometimes just men who want someone to dine with them at a fancy restaurant. They pay for your services through the agency, and you get your cut when the date is done. Simple as that.”
Services. His services. She’s making it sound totally legit and not shady at all, but that word sticks out like a sore thumb. “What do you mean by ‘services?’ You said it’s not sex work.”
“It’s not. You’re providing companionship for an evening.”
“So none of your…escorts or whatever sleep with the clients?”
“If the clients are inclined to provide a tip for additional services, that’s outside of the agency. We don’t ask questions, and it’s not expected. Most dates are just cut and dry, accompanying the client to the event, and that’s it.” Her stoic, professional demeanor cracks just a bit. “Look, some of our escorts do provide those types of services, but not all of them. It would never be expected of you to do that. And we would never push. It would be entirely your choice if that’s something you would feel comfortable with. But honestly…I have watched you tonight, and I really think you’d be great at this. It could be an excellent opportunity for you, and I guarantee you’d be making a hell of a lot more being served drinks at a gala than slinging drinks behind this bar.”
Eddie should have known from that first smirk she gave him that she would be getting what she wanted. This is the most tempting offer he’s ever received. He could try it out, right? Just like…one time and see how it goes?
“Let me think about it.”
She reaches into her handbag and slides a black business card across the bar.
Nancy Wheeler
Chicago Connections
“I look forward to hearing from you.”