My Cousin, My Escort

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My cousin, my escort

This following is a work of fiction but represents a fantasy I've had for years. It is not a fast read and is character and dialogue driven. If you're looking for a quick piece to breeze through, this might not be for you but if you stick around and get to the action (roughly halfway through), I think it's worth it. Thanks for reading and please let me know what you think below. Special thanks to my editor RandyD1369 for his work on this story. It was beyond helpful.

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It's amazing what little details a person notices when they're trying to think of something, anything, to take their mind off of a stressful situation.

As Tony sat in an unfamiliar bed roughly an hour away from his home, his brain scanned the room around him looking to find something to focus on besides the lump in his throat, his elevated heart rate and the thoughts about why he was there.

He could hear the low hum of a muted television to his left. A half hour or so ago, he was watching a replay of a fairly boring episode of Modern Family and trying, unsuccessfully, not to stare at the clock on his cell phone.

To his right, there was a hint of an orange or yellowish light coming through his hotel room's blinds. It looked like the headlights of a passing car.

"Was that her? Is she here?," he wondered to himself as he got out of bed and looked through the blinds. "No. It's not her. Not yet."

Even though Tony knew this was a tourist hotel, and assumed it would be busy on a week night, he looked around at the cars driving in and out of the parking lot around him and couldn't help but wonder if perhaps this hotel was TOO busy.

Maybe he made a mistake booking it? What if someone he knew saw him check in?

The questions swirled through his mind as the minutes passed. He was nervous, and with good reason.

After 38 years of leading what some would call a "boring" life----one where a person goes to college, meets their partner, gets a job, gets married and buys a house----Tony was about to do something he never thought he'd have the courage to do: He was going to pay for sex.

For over a decade, he's had this particular fantasy and, in just under 20 minutes, he was set to experience it for the first time.

Whenever he pictured this moment, he assumed he'd be excited. He thought he'd find it erotic. But now that it's here, all he can think about is finding a way not to throw up.

=====

Three hours earlier, in a room far warmer and more welcoming than Tony's, Cassie stood in her kitchen and had only one thing on her mind: Text notifications can be a real pain in the ass.

Standing in her kitchen wearing nothing more than a t-shirt and a pair of black leggings, Cassie had just finished washing the last of her dishes from dinner the night before when she heard the familiar buzz of her phone going off.

She was always conflicted when the sound came.

On the one hand, that little black box on the counter that she feels chained to at times makes it possible for her to live in this house. If she doesn't answer a potential inquiry fairly quickly, someone else might and when you're working in the sex industry, the only thing more frustrating than being on the clock all day is being on the clock all day and having nothing to show for it.

This lead was promising. This might actually happen.

Finally.

Thumbing her password into her phone, Cassie jumped over to her email and saw the reply she was waiting for.

It was him. It was Roger.

Roger? What a stupid name.

Well, okay. It's not THAT stupid a name but it's a stupid name for someone to make up as an alias and there's just about no chance the person she's been communicating with for the last week is actually named Roger.

Not that she has some moral high ground to stand on, of course. As far as "Roger" knows, her name is Alyssa. Yeah, it's not terribly creative but in an industry where everyone is named Candy, Fantasia or Destiny, it's easier to be subtle than creative when picking out an alias.

Cassie had run through her screening process dozens of times now and you can just tell when someone is using a fake name. But this guy sounded sweet.

Right from his first email, a bashful inquiry asking for more information on her booking process, she could sense "Roger" was her ideal client. He was well spoken, patient while he waited for her to reply and his requests were about as mundane as you can get in the sex-for-money trade. It's a far cry from what she's used to, she thought as they communicated back and forth.

Maybe that's why she let him get away with the made up name. Maybe that's why she didn't press him to send her references from other escorts or a photocopy of his ID with a link to his Facebook profile and LinkedIn page.

"You're making a mistake." she said to herself, more than once.

If Cassie had followed any of the regular steps of her process, she might have avoided the awkward situation she'd find herself in later tonight. But this guy seemed genuine and, hell, if things went sideways she could just knee him in the balls and take off.

Overconfidence was her second mistake.

Her third was taking his money.

When Roger was hesitant to give her his ID, Cassie told him she wouldn't continue their conversation without a 50% deposit. It was sent moments later. He hesitated to give her too much information but had no trouble sending her half the money up front?

"Yeah," she thought. "He's definitely married."

And that's how she got here. The phone chimed just as Cassie thought it would. He'd just sent the rest of the payment.

A cop wouldn't do that. Someone who might be a risk to your safety wouldn't leave that kind of paper trail, even if it was just electronically. Hell, anyone who knew anything about the sex-for-money business would know paying in advance is just asking to get burned. Clearly, this guy hadn't done this before.

Paying for her services meant there was no turning back for Roger, or whatever his name was. All Cassie had to do was show up.

They could proceed. She was willing to take the chance.

As Cassie looked over at the outfit Roger has requested she wear, she couldn't help but think this would be a good night. Sometimes it's important to build trust with a new client. It's how to create regulars and regulars are a lifeline for girls in the sex trade.

So what if he was married? Her job is to please her clients, not play marriage counselor.

If she knew who she was talking to on the other end of those emails, she might have played things differently.

Then again? Maybe not.

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Tony looked down at his clock again. Barely five minutes had passed since the last time he checked.

He closed his eyes and let the feel of the room overtake him. The hum of a busy parking lot was both comforting and concerning but it was the smell that really stood out.

Even though he knew from the minute he walked into this hotel that his room was clean but it almost felt ... too clean. Like it was too sanitized. Like someone came in and wiped down every inch of the room with Lysol and took any sense of personality with it.

Those were Tony's thoughts as the clock ticked closer to 8 p.m. He looked at his hands and could see beads of sweat forming on his palms. He was nervous.

Tony was trying, and failing, to do whatever he could to stop from focusing on why he was in this room.

Tony was a married man, happily married in fact. And he's not proud of what he's doing here but, honestly, it's for the best. Spiritually. Mentally. Physically.

Kayla would understand.

Tony's wife knew he would end up doing this one day -- he'd been open about this fantasy for most of their marriage -- and while their relationship might not be as physically satisfying as he wanted it to be, it's otherwise absolutely perfect. He loved her. She loved him. But he needed something different.

When you'd been together with someone for close to two decades, that's just the way it was. You could still love each other and be there for each other but, physically, you couldn't expect the excitement to still be there the same way it used to. And if you hadn't lost your need for sex, but your partner had, it's impossible to bury that thought forever.

He's not cheating.

No, really. He's not.

His wife knew this would happen.

There aren't a lot of people who would understand the deal Tony made with Kayla on their last wedding anniversary but it was completely on brand for their relationship. Permission to hire an escort? What kind of wife would allow that? It was practically unheard of in their small Florida town.

But she did. And bless her heart for it. Kayla understood that what her husband was asking for was strictly a physical release. It's really no different than jerking off to porn or using a Fleshlight. In fact, the only rules she put in place were that no one else could know about it and they'd never speak to each other about it.

Kayla's mindset was simple. When the man of your dreams, the one you've built a life with, asked you for something important to him, and explained why he needed it, there's really no reason to say no. Not when you have that level of trust. Not when he's spent his entire adult life giving you everything you wanted and more.

Kayla knew Tony wasn't going to leave her for an escort he slept with once or twice. So, while she didn't want to think about it, she didn't mind saying yes when he asked for that pass almost eight months ago.

He still hadn't used it though. Until tonight.

Maybe he was scared. Maybe he was nervous. For whatever reason, even WITH his wife's blessing, Tony couldn't help but think this whole thing felt wrong.

Wrong.

It felt wrong.

And "feeling wrong" is exactly what led to him contacting Cassie for the first time.

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At 38 years old, Tony was the definition of a simple guy. He worked 9-5. He spent time on the weekends with his wife and his friends and complained on Reddit when the writers of his favorite TV shows botched the ending. He's the quintessential mature, responsible man ... who also happened to love porn. A lot.

Ever since Tony was a teenager, he'd watched porn almost every day. Sure, that's not surprising. A lot of men do. But what started as a fun way to spend a few minutes forgetting about the tasks and world around him quickly turned into a hobby. There's not a day when he wasn't at least scrolling through videos on his favorite tube sites to see what's new, even if he didn't always masturbate to them.

Tony loved amateur videos more than overly-produced ones but, really, his interests tended to fall into videos that had a story or could at least be plausible.

That's where he got his fetish for sex workers. It's a popular genre. A guy hires an escort, pays her an undisclosed amount of money, gets what he wants and they leave.

It's a simple concept on the surface but deep down? It's wrong. Or, at least, the stigma around paying for sex and sexual exploration as a whole makes it "feel wrong." That's also what makes it exciting.

When done properly, escort porn takes the time to develop the relationship between the guy and girl before the sex starts and it makes the inevitable action between the sheets much more rewarding. You can't just get right down to the sex. If you did, why would you bother creating a storyline in the first place? Why wouldn't you just get your actors to smile, look at the camera and start fucking?

Escort porn is different. It takes the time to slowly build the erotic excitement that makes that sweet release feel special. That's why he's here, in the middle of a nondescript hotel room with a raging erection, waiting for the first escort he's ever had the guts to contact for a real-life appointment.

It was bound to happen. You don't fantasize about something for as long as he has thought about this without eventually giving in.

And fantasizing was what he's been doing nonstop since Alyssa agreed to meet him.

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It all started with an ad.

Bored one day and looking to find something exciting to jerk off to while his wife was at the grocery store, Tony checked out the local board on a website where men from his area gathered to talk about sex workers.

From time to time, he went on this site to fill his fantasies and let his mind wonder. Most of what's on there is bullshit and he knows it but readers could usually figure out what's real and what's not and they almost always provided links to real escort ads, which are a great resource when you want to roleplay in your head and imagine hiring someone for sex.

Inevitably, Tony would read a description of one of the local girls, check out her ad and spend the next 10 minutes or so fantasizing how he would contact them, what he would say and how their entire sexual encounter would go.

Most of the ads were crap. Blurred out photos with piss-poor writing and obvious scams were all too abundant on the mainstream escort sites. But every now and again, if he was willing to sift through the garbage, he could find something worth thinking about.

Tony knew the minute he saw Alyssa's ad that something was different. Instead of cheesy non-specific titles like "Sweet girl wants to make you feel great," Alyssa's ad was poignant and direct and oozed a certain type of sexual confidence that Tony couldn't get enough of. Right from the title of the ad ("This is so much more than sex,") he was intrigued.

"You're not buying sex. You're buying an experience —

Are you bored? Lonely? In a sexless marriage? Missing that spark that only comes from a new experience in an otherwise boring life? Hi. I'm Alyssa.

I'm a real, independent, brunette 35-year-old and I don't have time for games. You know what you want and why you're looking at my ad. I know how to make it worth your time and your money.

If you're looking for a quick and easy fuck, I'm not the person for you. But if you want the type of experience you'll still be thinking about in 20 years, I'm worth. every. penny."

If there was ever an ad written specifically for Tony, this was it. And if the ad didn't catch his attention, the photos sure did.

Alyssa's profile had a handful of clearly well thought out photos on display and, unlike every other ad he'd seen on this site, they weren't taken with a shitty cell phone in front of a mirror.

No, these were more than selfies meant to show tits and ass. These were art. The first three showed Alyssa wearing high-end lingerie, a black and white top that showed her curves. The next two were a little more risque and shot from behind her, showing one of the sexiest asses Tony had ever seen. There were two topless photos, where she hid her nipples from view in an implied-nude and the last few were full body, head to toe shots of her wearing dark lingerie, fish net stockings and sexy high heels.

The only thing missing was her face but, if you'd seen enough of these ads, you'd know it's pretty common for girls to hide their faces to protect their identity from those looking to out them, harass them, or ruin their private lives.

The moment Tony saw Alyssa's photos, he had a raging hard on that demanded attention. It wasn't just the way this girl wrote her ad that struck him, it was the overall presentation from top to literal bottom.

This was clearly a girl who knew what she was doing. He did not.

It took Tony nearly seven hours, and two jerk off sessions in the bathroom, to work up the courage to actually send Alyssa an email through her own personal escort site linked in the ad. He chickened out at least four times, but once he sent that first message, he knew immediately he was in trouble if she responded.

She did.

And he was.

=====

That first email came to Cassie the way they always do. In the middle of the night, while she was sleeping. Guys love sending these initial inquiries at ungodly late times.

It makes sense. You're up late, winding down from work and ready to go to sleep so your brain turns to sex. Maybe you slog through another boring missionary-only, lights off session with your partner. Or maybe you jerk off alone.

Either way, it's prime time for reaching out to a sex worker for your unfulfilled fantasy and while Cassie knew "Roger's" inquiry was probably a waste of time like the other nine she got that day, it's always worth responding to see where things go.

The key was to keep it simple, short and sweet. Never get specific about sex acts in an email, never tie sex acts to money. Set up a couple of obstacles to trip up your time-wasters or law enforcement officers looking to set up a sting.

It was a time tested system Cassie worked out from weeks of research on a sex worker Reddit board and DMs to real-life escorts who appeared friendly on Twitter. For a bunch of strangers selling their bodies, the sex worker community can be oddly reassuring at times and it helped her immensely when she was just started out.

Cassie's first reply to Tony fit all her criteria. It took 30 seconds to send and she immediately put it out of mind. It wasn't until he answered that email, paid half her rate up front and they actually set up a time to meet that this felt real.

That was a week ago. Tonight's the night they agreed to get together and Cassie was ready to make quick work of her latest client. The faster you get them off, the faster you can go home. With a body like hers, that was never much of a challenge. It wasn't always that way.

Cassie grew up as the youngest of three sisters and never felt particularly great about her appearance. For the first 16 years of her life, she looked like a stereotypical awkward teenage tomboy. She wore baseball caps, baggy t-shirts and ragged jeans and could not have cared less about her appearance.

It wasn't until she caught a late growth spurt and suddenly had bigger tits and a shapelier ass than either of her siblings that things really changed, both physically and mentally. In a span of one summer, she went from being invisible to the opposite sex to the girl everyone of both sexes snuck a peek at when they thought she wasn't looking.

And the boys? The same ones who used to be mean and make fun of her for her flat chest and awkward clothes were the ones suddenly tripping over themselves to have a chance at her.

Cassie's attitude didn't change too much internally as she grew up but she wasn't stupid. She was always the same girl at her core but she knew her appearance was an advantage and she used it as such. In college, she always wore lower cut shirts when she was out with friends and she NEVER paid for a drink.

In fact, college was the first time she was ever asked if she'd trade sex for money.

His name was Greg. He was an ex-boyfriend but not someone you'd ever take seriously. Months after they broke up, Cassie ran into him on a night out at the local Irish dive bar. It's a night she won't forget and she still occasionally laughed about it when it popped in her mind.

"Hey Cass, I miss you," Greg slurred. "Let's hook up tonight. Come on. I just wanna have fun."

"You're drunk," she replied, waiving him away. "Go home."

"Come on," he insisted. "I miss you. Let's have fun. I'll, like, give you some money or whatever."

"I'm not a whore, asshole," Cassie said, taking a drag from a half-smoked cigarette. "If you want a hooker, go online and get one."

Cassie never fucked Greg again but she thought about his offer for longer than she'd ever admit.

Why not? She liked sex. She liked making money. And, hell, it was 2014. Sex work isn't even that frowned upon anymore. Chances are, if you asked enough people, you'll find someone who had sold nudes or stripped before. If they haven't and they're under 30, they've probably taken the photos and sent them to someone for free anyway. Why not make some cash while you're doing it?