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The Accidental Escort

"She went on a date and ended up with a career."

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Author's Notes

"Alicia had a history of picking the wrong men. Maybe the solution was having them pick her"

Shit, he’s thirty minutes late and still no text. The son of a bitch is ghosting me! Alicia shoved her phone back into her purse, cursing herself for picking the wrong guy.

Again.

I should’ve known better than to trust a guy named Chad! Why didn’t I swipe left on his ass?

But it wasn’t his name that made her swipe right. She’d answered him because he was hot. That was her first mistake. He probably had two dates lined up for tonight and I’m the one he chose to stand up! Ugh!

But while Chad may have been an asshole, he did have nice taste in bars. She had to give him that. Alicia had never heard of the Blue Raven, probably because she would never have been able to afford a club like this on her own. At twenty-two, she was saddled with student debt and a credit card threatening rebellion against her bank account.

In the back of her mind, she’d known he was toxic, but she couldn’t resist his six-foot-two height and a smile that made her knees weak. The Maserati he was leaning against in his photo didn’t hurt either. The problem was, every other woman on the app was probably thinking the same thing.

Now, she was a party of one, pathetically occupying a table for two while nursing a second Cosmo she couldn’t afford. It was humiliating, and she couldn’t quite shake the idea she’d done this to herself.

“The fuck I did,” she self-corrected to her now-empty glass. “The only thing I fucked up was trusting a man to do the right thing for a change.”

It was infuriating, and now she was at a point where her presence at that table was screaming that she’d been stood up, so she decided to head for the bar for one more drink before heading back to her empty apartment.

She’d just signaled the bartender for a refill and was pulling out her credit card when she felt a presence next to her.

“Why don’t you let me get that for you,” the man offered in a voice that was both deep and confident.

Alicia’s bitterness was already coiled like a snake waiting for a target and her entire demeanor turned to ice. “Sure. Whatever, it’s your bill,” she responded dryly, barely looking at him.

The man dropped a fifty when her drink arrived and only then did she turn toward him. He was an older man, maybe twice her age, which in that moment was a plus. Had he been a carbon copy of Chad, she’d have frozen him out for nothing more than spite, but this man had a presence Chad could never have hoped to match.

He was tall, which was a plus, and looked amazing in his suit. His slightly graying hair was perfectly groomed and he carried himself with a confidence that held none of the sleaziness or air of superiority wealthy college boys so often displayed.

“Thanks,” she offered, immediately suppressing the dismissiveness she had previously felt.

“You seem upset. Did your plus one not make it, tonight?”

Ouch, was it that obvious? He was right, of course, but goddamn it, that was the last thing she wanted to admit, so she shook her head and took a drink, hiding her shame behind the glass.

The man smiled, looking at her as if he were reading her mind. “You know, the Blue Raven attracts two kinds of beautiful, unattended women like yourself. The unfortunate young ladies whose date failed to show and one other kind. I’m just wondering which of those you might be.”

Alicia had no idea what he was talking about, but in that moment, she needed a compliment so she smiled back at his appreciation of her appearance. “Well, I wasn’t stood up,” she lied, “so what other reason do you think might have brought me here?”

She knew as soon as she said it that she was opening herself to more disappointment, but failing the admission of her being shamed, she hoped she could bluff him long enough to run with whatever he was talking about.

The man leaned with his back to the bar, holding the drink he hadn’t touched. “Young ladies who know what they have and what they want. So, which are you?”

Alicia took a deeper drink from her glass. She was only about one hundred and five pounds and the alcohol was hitting her harder than she realized. As a result, she completely misunderstood his meaning. “That’s me, I guess. But knowing what I want is easy. It’s getting it that’s the tricky part.”

She, of course, was still talking about being stood up and found herself enjoying his mysterious banter. Meeting his gaze, she decided to call him on the game she assumed he was playing.

“So, now that we’ve established why I’m here, why don’t you tell me what happens next? Why are you here?”

“Ah I see,” he responded. “You need to be careful, but don’t worry, I’m not a cop and they aren’t likely to do something that would upset the Raven's clientele anyway."

Later, Alicia would be kicking herself for not understanding why that mattered, but she was young and had no experience with such things, and so was mystified as to why he would say that. But she did feel the conversation taking a turn, so she confined herself to being evasive, hoping she would catch up before he realized he’d lost her.

“That’s good to know. I’m Alicia, by the way.”

“Michael, and it’s nice to meet you, Alicia.”

What followed was an awkward pause, as if he were expecting her to say something more, but she had no idea what that might be. So, they stood there looking at each other until an indecipherable smile appeared on his face. “You are new at this, aren’t you? Let’s make this easy. How much do you charge for the night?”

“All night? What?” Her voice died in her throat as understanding began to dawn on her.

“Sure, why not, I prefer to take my time with such things and you won’t have to come back here again tonight. So, how much?”

Oh, my God! He thinks I’m a hooker! What the fuck! It seemed ridiculous and she should have been angry but all she felt was irony. In a night a man had already treated her as badly as she thought possible, she’d managed to find another with even less respect. It was preposterous and insulting, but she was attracted to him, and through the alcohol's haze, it seemed uproariously funny.

All right, smart ass, she thought defiantly, now it’s my turn to embarrass you! “A thousand for the night,” she dared him, never believing he’d accept such a ridiculous amount.

“Done,” he responded without hesitation, leaving her utterly speechless. “I’ve got a suite at the Kensington ten minutes away. I’ll drive.”

Alicia couldn’t believe it. A thousand dollars and he said yes! Holy shit! He wants to fuck me bad enough to pay me a grand for my ass? Hell, I might have fucked him for free!

That and many other thoughts hit her like a thunderbolt, and her mind juggled a dozen conflicting emotions in a microsecond. Could she actually give up her ass for money? Truthfully, she’d had sex with guys for nothing more than a few drinks, and she would have probably gone home with Michael if he’d just asked, so, why not? Besides, she sure as hell needed the money. Still, she couldn’t bring herself to say yes, but she didn’t quite have the will to say no either.

So, when Michael held out his hand, she took it, still not quite believing the mess she’d gotten herself into.

oo0oo

Alicia said little through the ride to the hotel. She’d barely come to her senses by the time the valet brought his car around and that sent her on another wave of confusion. He had to be from out of town, why else stay in a hotel? But what kind of man rented a Ferrari? She just couldn’t believe any of this was happening.

And Michael kept flashing that damn indecipherable smirk, as if he found the entire situation amusing. But he was being incredibly polite, other than thinking she was a whore, of course.

At least he didn’t think I was a cheap one. A thousand bucks to sleep with me? It’s kind of hard to be insulted by that! It was confusing as hell, and by the time they reached the Kensington, she still hadn’t decided if she should be insulted or consider it a compliment.

The hotel itself was as impressive as the Ferrari. It was absolutely beautiful; from its marbled walls to the rich and elegant decor, it screamed excess and sophistication. Had they arrived at someplace horrid, she likely would have backed out, but so far she felt like a lewd version of Cinderella.

Even by the time they reached his suite, they still hadn’t spoken much. Alicia gathered that asking hookers about themselves was rather pointless, and anyway, what could he ask? How long had she been sucking dick? They were there for sex, not to get to know one another.

Alicia did have a million questions, but some she would know if she was what she was pretending to be. Others, like if he was married or had kids, she was afraid to ask. He wasn’t wearing a wedding ring, so she assumed it was a no to the former. All of those questions got put aside when they entered the room.

And calling it a room simply didn’t do it justice. It space was huge, with what must have been two bedrooms and a large and luxurious living space. On the far wall was a wide sliding glass door that led to a balcony outside. One thing was certain, this Michael was rich, and she began to wish she’d asked for more than a grand. Perhaps a lot more.

“You can use the bathroom in the master,” Michael said, gesturing to one of the doors. “I’ll make us a drink. We have all night so take your time.”

Michael was opening his wallet as he spoke and set a thick stack of bills on the bar. He said nothing about it but causally gestured toward it as he went behind the counter. Alicia gathered that it was her pay, so she picked up the cash and headed into the bath.

oo0oo

As Alicia glared at her reflection, she debated whether she would still respect the person she saw if she went through with this. But the cash was real, and it represented a significant portion of her monthly bills. It was so much to her in fact that she reasonably couldn’t turn it down. Her mom might not approve, but her mom wasn’t paying her bills, either.

“Okay, Alicia,” she told herself. “You're doing this, so you might as well do it right. Maybe you’ll even enjoy it.” With that, she ran through a mental checklist, considering what she would need to please her ‘John’.

She had condoms, thank God. She thought she’d probably have sex with Chad and she knew a guy like him wouldn’t bring any. After all, a girl learned to be prepared and that wouldn’t have been the first time she fucked a guy on the first date.

A bigger issue was that she didn’t feel aroused at all. It wasn’t that she wasn’t attracted to Michael, she was, but the situation was far too stressful for her to be moist. If he wanted to simply fuck her without foreplay, she’d likely not be ready for him.

Unfortunately, she didn’t have lube and the bathroom offered no alternatives. She’d just have to make the best of it. After brushing her teeth with one of the hotel's sterile brushes, she fixed her hair and looked at her reflection again.

She looked good, at 5’2 and in a dress meant to show off her trim body, she was pleased with what she saw. Adjusting her boobs in her bra, she took a breath and went out to meet Michael.

She found the bedroom empty and undisturbed, which was a relief. She’d feared he would be naked on the bed, or some other presumptuous shit, but he’d apparently given her some space. She was about to move out of the room when she stopped and made a decision. Okay, girl. If you are doing this, then make it good.

Heading deeper into the room, she took off her dress and laid it carefully on the bed. She left her heels on and appraised her look in the mirror. Her blonde hair flowed down, partially covering her shoulders, and her black bra and panties that she’d worn for Chad looked stunning against her pale skin. “There we go,” she whispered. “If that doesn’t do it for him, he’s either gay or dead.”

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She was feeling better about it all by the time she met him in the living room where he was sitting on the couch, and the way he gazed at her sent her confidence soaring.

“Wow, you look amazing,” he said as he stood, greeting her at the couch. Handing her a cocktail, he gestured to the couch, inviting her to sit next to him.

Thank you. You look great too,” she responded as she took the drink and sat. She was about to cross her legs but chose not to. She was there to turn him on, after all, so modesty seemed out of place

So, what would you like to do?” Alicia winced at having to ask, but frankly, she had no idea what else to say.

“What I’d like is to sit here for a while and look at you. You are absolutely gorgeous. The rest will come when we are ready."

“Really? Most guys would be all over me by now.”

She knew this from experience. The guys she’d dated were always in a hurry to get into panties and patience wasn’t at all what she was expecting now. The very fact that he wasn’t, even after paying her for it, caused her respect for him to grow immensely.

“Probably so. But that’s why I wanted the night. I hate rushing into it and most working girls want to get it done and leave as quickly as they can. I hope you understand.”

“Of course. Like you said, I’m here for the night. There is no need to rush.” Alicia was surprised and relieved by this. She didn’t want to rush either and this was feeling more like a date now than most of the real dates she’d been on.

They spent the next couple of hours talking about him, which was fine. She understood that escorts probably didn’t want to reveal much about themselves anyway. But she learned quite a bit about Michael. He was in imports and had been married with three kids. His divorce had been messy though and that’s why he now avoided relationships.

That was why he preferred escorts, because that way he got what a man needed without the attachments he wasn’t ready for.

But those hours weren’t without intimacy. Somewhere in there he began caressing her bare leg, letting his touch slowly build the mood. Soon, she was feeling her attraction for him grow and her body responded in kind.

She was getting hot, and so allowed herself to return his touch. When he kissed her, it felt natural and she returned it with the same need and passion with which it was offered. She was the first to go farther, sliding her small hand up until she felt his erection under his pants.

Michael’s breath came deep as she squeezed him, and she was happily impressed by what she felt in her hand. He was ready and so was she, so she unhooked her bra, and let it fall away, revealing her breasts.

Alicia had no reservations now. She wanted him as badly as he wanted her. Even better was the fact that she felt no need to be shy or coy anymore. She was there to fuck, and they both knew it. It was liberating, and she decided for once to take the initiative. Placing his hand on her breasts, she sucked in a breath, reveling in how it felt to be fondled.

They kissed again, deeply, caressing each other's tongues with heated desire. Then she rose, offering him her tit, and inviting him to suck it, or bite, as much as it pleased him.

Michael did both, flicking his tongue over her nipple and sucking it between his teeth. The sting was sharp and exciting and she cooed to him as she held his head to her breast.

The freedom she felt at being paid to be with a man she didn’t know and would likely never see again was incredible. For the first time in her young life, she felt like she could let go and be as slutty as she wanted to be. She was hotter than she could remember being and she moved over him, straddling his lap as she kissed him again.

Then came the wrestling with his suit. She peeled off his jacket and they were giggling in excitement as she untied his tie. And every chance he got, he fondled and played with her boobs, driving her wild as he did. But it was only when she unbuttoned his shirt that she realized just how delicious his body was.

He wasn’t overly muscular, but she could still make out his pecs. What really got her though, was the wispy hair trailing down to his stomach. Kissing his nipples, she moved downward, following that trail until it disappeared under his belt.

Alicia wasn’t a huge fan of sucking cock, but in that moment she had an uncontrollable urge to taste his musky flavor. Gazing up and into his eyes, she dropped to her knees in front of him and unbuckled his belt. Biting her lips, and feeling shy and excited, she had no need to tell him what she was about to do.

Michael’s breath came deep as she unzipped him and settled deeply into the couch as she reached into his pants and found his cock. Alicia watched his reaction, growing more needy as she saw how she was affecting him. When she found his hard shaft, she pulled it out and smiled at how fucking sexy it was in her hand. Then, with her eyes on his, she opened her mouth and slid it over his thick and purple head.

His taste was musky and masculine, and for the first time, she thoroughly enjoyed the sensation of it filling her mouth. She felt incredibly naughty, and might have been ashamed of herself because of why she was doing it, but she couldn’t deny how hot it was making her. Closing her lips around his head, she explored it with her tongue until his skin was wet with saliva. Pulling back and then taking more, she began sucking him in earnest.

Alicia was getting lost in the act. She’d finally let herself go and she worked his cock with a passion that shocked her to her core. She had no fear of his cum, and actively wanted to taste it when he filled her mouth. And all the while she kept her eyes on him, becoming even more aroused by the sight of him getting his cock sucked. It wasn’t until he spoke that she came out of her lustful trance.

“Alicia, please, slow down, you're going to make me pop, and I want to do so much more with you.” His voice was husky and strained, letting her know just how close she’d gotten him.

Reluctantly, she pulled off of his cock, rubbing it on her face and smiling brightly. “You are the boss,” she said, “but I’d love to taste your cum.”

“Oh, my God, you are killing me, but I want to fuck you first.”

“Mmm,” she laughed. “Finally I meet an honest man.” Then she guided him to his feet and lowered his pants to the floor. Once he stepped out of them, she pushed him back onto the couch and removed her heels. In an inspired moment, she opted not to remove her panties. Instead, she stood on the couch between his legs and with her pussy inched from his face.

“Take them off me and you can fuck me all you want.” Alicia felt like an entirely different girl and she was shaking as he hooked his thumbs under the hem and dragged her panties down her slim legs. She was dripping wet and she spread her legs wider when he slipped his hands over her slit.

The sensation was electric and became more so as he separated her lips with his finger. She felt unstable there and leaned in, bracing herself on his shoulders as he teased her clit. Being fingered like that was driving her mad and she already felt the distant stirrings of a massive orgasm. Her eyes closed and her head tilted as she searched and concentrated on that impending bliss.

All of that must have been getting to Michael as well, for in an unexpected moment, he scooped her up effortlessly and laid her on the end of the couch. Without waiting, he slid up and dropped his mouth right on her puffy sex.

Alicia was completely shocked and felt his tongue penetrating her before she could react. The sensation was soft, wet, and insistent and that distant storm exploded in her body, causing her to cum hard and writhe uncontrollably in his grip. Her vision had barely cleared when he moved up and brought his cock to her entrance.

They were on instinct now, both needed to feel each other in the most intimate way possible. She was so wet he had no trouble sliding into her and the feeling of being stretched and filled made her moan with a feral passion. He was fucking her hard and still increasing his speed when she remembered she’d never given him the condom.

But, at that point, she no longer cared. If she had to, she’d get the morning-after pill in the morning, but for now, she just held his hips, guiding him in a rhythm that made her pant with need. This was what she needed, to be ridden without restraint and that’s exactly what he was doing.

Watching him closely, she could tell he was close. She wasn’t going to cum again, but that was fine. It let her concentrate on him and knowing he was so lost in her was incredibly satisfying all by itself. “Come on, that’s it, Michael. Fuck me like you mean it. Fuck me hard!”

And he was. She marveled at him as he rode high in her saddle, holding him tightly as he took her. Just before he came, he shocked her one last time.

“I’m gonna cum,” he grunted. "Should I come inside you or pull out?”

Alicia couldn’t believe it. He’d paid her fat to fuck her, and now he was asking if he should pull it? None of her boyfriends had ever done that. In that moment she couldn’t imagine making him stop and she just held him tighter. “Inside me, Michael, fuck me until you cum.”

In a moment, his thrusting became wild and erratic, and his body flexed hard as his cum exploded into her.

oo0oo

Later that night, she got her wish by tasting his cum. It felt like a rite of passage to her and the taste stayed with her for the rest of the night. The next morning, they fucked again before getting out of bed.

By the time Alicia showered and dressed, Michael had made coffee, handing her a cup, he asked her to sit for a minute before she left.

“Be honest with me. You weren’t there to hook last night, were you?”

It wasn’t really a question and Alicia felt her face redden in embarrassment, “No, I wasn’t. I got stood up, but I just couldn’t admit it. The next thing I knew you were offering so much money and you were so attractive I just couldn’t say no. I’m sorry if that disappointed you.”

Michael smiled. “I’m not disappointed at all. I figured all along you weren’t and once you accepted an all-nighter for an hour's pay, I was sure.”

Alicia's eyes widened at that. An hour's pay? You mean they get a thousand an hour?” She didn’t think it was possible but he just nodded yes.

“For girls with your looks at a place like that, absolutely. That’s common for a high-end escort, and believe me, I’ve paid for it enough times to know.”

Michael opened a box and pulled out a massive stack of cash. “That’s ten grand more, and believe me, you’ve earned it. Frankly, I feel like I’m insulting you by offering it, but I would also feel like shit if I stiffed you.”

“Holy shit,” Alicia said quietly. That stack of hundreds was more than enough to pay off her credit card and leave her flush for the month. She was stunned and had no idea what to say besides, “Thank you.”

Michael just smiled and gave her his card. “I don’t know if you intend on pursuing this business, but if you do, give me a call and I’d be glad to set up another date.

"I’ve also written a number on the back. It’s an agency that would treat you right and keep you safe. Whether you use it is up to you, but I’ll give them your reference in case you do decide to call.”

Alicia put the card and cash in her purse and got ready to leave. “Before I go, how did you know I wasn’t a pro. Wasn’t I good enough?”

Michael took her hand. “You were too good. Even the best escorts put up an emotional wall that makes it almost impossible to connect with them. You didn’t, you were as into it as I was. That made you incredibly special. I don’t know if it’s even possible for a woman in that field to maintain that, but if you can, you’ll never have to worry about being good enough. And if you don’t, well, you are going to make some lucky guy very happy.”

oo0oo

Michael called her a cab and thirty minutes later, she was in her car in the Blue Raven's parking lot. Staring at the card, she had no idea what lay ahead for her, but she’d learned a huge amount about herself and she knew she had to try.

Published 
Written by David_LeRoy
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