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Derek had been doing this job for a while now and was actually pretty good at it. He was actually surprised at how good he was. Even if he’d kind of dove head first into being an escort, there was always that nagging feeling in the back of his mind that he wouldn’t be able to handle. The having sex with strangers and not getting attached in some way, Derek wasn’t sure if he could cut it. Turns out he’s kind of a natural. There were some drawbacks, that he had to admit but he did meet some pretty interesting people.
Every Monday Derek got up at nine and took a shower. He would put on his black suit with accenting red shirt and look over himself in the full sized mirror before heading out of his room. As per usual he would exit to find a face down Isaac draped over the couch. He’d set Isaac’s phone to go off at noon so that he wouldn’t miss his classes for the day and program the coffee pot to brew a full pot for him to attempt to shake off his hangover from the previous night. Derek would always leave a note about him going to an early work meeting and that he would meet him in class even though it wasn’t necessary, by now it was part of their routine.
Derek would head downtown to meet and Duncan and the other boys at Le Deux. They sat in the back away from everyone, just where Duncan liked. He took a seat at the farthest end of the table, facing the door. Duncan sat at the head of the table browsing through his calendar on his phone, most likely waiting for Derek to arrive. He was usually the last to arrive even though he was still early. They were all overly punctual, always were. Derek recalls once after first joining the team they all met at bar for drinks, Duncan’s idea for everyone getting to know each other. Of course he came in right on time to find that all of them had been there for at least thirty minutes.
All of the other men were looking over the menu or checking text messages. They were all dressed in the same black suits except for their shirts which all matched their assigned colors. Duncan pinched the bridge of his nose, narrowing his eyes as he cleared his throat and placed his phone into the small pocket on the inside of his jacket. Without saying a word he opened his briefcase and distributed manila folders with color coded labels and envelopes attached. Duncan slid Derek’s across the table. He removed the envelope with the named Philip written in cursive and looked inside. This was his payment for the week. While all of the boys received their own payment from each client, they were also paid for being a part of the team.
He slipped the envelope into his pocket and watched some of the other men around the table. Some of their faces indifferent, others contorted in a grimace of discontent. Their pay varied on their performance in bringing in business and Derek was one of their hottest additions. While he wasn’t at the top of the list he was pretty close.
Duncan cleared his throat again pressing a closed fist to his lips.
“As you can see from your schedules for the week, there have been some new developments.” He coughed again.
“Are you okay?”
A blonde gentleman sitting to Derek’s right asked. Derek couldn’t recall his name. All he could remember is that he was the group’s highest earner, meaning he was the most requested. He readjusted his teal shirt, looking legitimately concerned about Duncan’s well-being.
“I’m fine. Just a cough that I can’t seem to get rid of.”
Duncan removed a cough drop from its paper popping it into his mouth with a light knocking noise against his molars. Derek could see a brief sense of worry pass over his face before replacing it with his usual smile.
“Be sure to keep your phones on this week. I had to fire my assistant Stephanie or whatever her name was, so I’ll be handling all appointments personally.”
“I guess now she’s gone back to her home in the sea with the rest of the dolphins.”
There was a collective chuckle that seemed to shake all of their shoulders. Derek couldn’t help but join in their laughter. He was never overly fond of her, no one really was. Her voice was too much for most people to stand. Mica was usually one to make a joke at the poor girls expense. He was actually quite funny. Mica was the kind of guy that could see himself being friends with outside of the work place.
Duncan pushed back in his seat, clamping his briefcase shut.
“As usual lunch is on me. Try not to over stuff yourselves. Some of you are working tonight.”
He shot them a smile before stepping away from the table in a hurry. Duncan, for the most part, typically stayed at least halfway through their weekly meetings. So to Derek this seemed a bit out of character.
He’s just your boss. A boss that you don’t even know that well. Derek thought to himself lifting up the menu.
They ate there pretty much every week and Derek never knew what he wanted. Everything on the menu was overpriced and over exaggerated for his taste but he wasn’t paying so he could find SOMETHING edible.
Derek and the other men spent the next hour eating in mostly silence. It was really how they spent most of their lunches. Mica would make and joke and they would all laugh. Pewter, Derek couldn’t recall his name even though he was sure he’d heard it a number of times, would try and make conversation by talking about events that were going on around town but no one would bite. So they just spent the time eating and glancing at their phones.
Derek was usually the last to leave. Mainly because he didn’t want any of his colleagues to see the crappy car he was driving. Today was no exception.
He watched them all get up and leave until it was just him and lavender were the only two left. Derek knew that his name was Donald, at least that was his cover name, but he preferred calling him by his color. He didn’t want to give him the remote idea of familiarity, that they could have the possibility of becoming friends.
Derek wasn’t fond of Donald. He would even go on record to say that he loathed the guy. When he went to his first meeting Don made it his personal mission statement to point out that Derek was the newbie and that he was top dog. Derek made a remark about at actually being Blue that was the top earner and that he was second rate compared to him in looks and worth. Since then the two of them haven’t spoken, just exchanged dirty looks.
Derek stood up straightening his jacket and wiping small crumb particles from his pants. He motioned towards the exit and heard the scuffle of Don’s chair against the floor. It wasn’t until Derek was outside that he even noticed Don was behind him.
“Hey wait up!”
Derek let out a sigh loud enough the Don could hear his irritation.
“What do you want? I have things to do.”
He turned around to look him in the eye. Derek had to admit that the guy was pretty attractive. He had sandy blonde hair and a chiseled jawline that rivaled his own. Not to mention his piercing blue eyes that most people would kill for.
“Stop stealing my clients.”
His brow was punched together in a frown. Derek couldn’t help but roll his eyes in defiance.
“How do you know it was me?”
It was a fair question.
“There are five other guys besides me. Why do you automatically assume it was me?”
Another fair question. Don looked at him in disbelief, as if he was surprised that Derek would even ask.
Derek lifted his eyebrows adding emphasis to his question and he waited for an answer. Finally he got tired of waiting for a response and left Don standing in front of the restaurant, mouth open trying to find words to combat Derek’s rebuttal.
Fact is Donald was right. Derek had taken some of his regulars, six of them to be exact, but Derek wasn’t going to openly volunteer that information to him. Don had gone out of town a month or so ago so Duncan just kind of dumped them on Derek.
Derek didn’t really mind. Some of his new clients were quite interesting. He’d even given them all monikers to fit their quirks and personalities.
First on his list of appointments this week was ‘The Senator.” Derek named him that for his striking good looks, the kind that you would expect from a politician. They would meet once every two weeks for him to ‘unwind’ as he put it. Derek was pretty sure that he had a wife judging by the tan line on his ring finger. He’d spend somewhere close to an hour fucking his brains out before they’d go their separate ways, ‘the Senator’ leaving a good fifteen minutes before him so not to be seen together.
Then there was ‘the Gym Bunny.’ He was an interesting one. Derek would usually meet him at his place where they would go to his home gym. It must have been a fetish of his or something. He’d watched Derek work out and flex his muscles, even joining in to workout with him until they were both soaked in sweat. That’s when he wanted Derek the most. Gym Bunny, or GB as Derek calls him, was what he learned in the industry to be called a power bottom. GB would push back into his hips with every stroke begging for the length of him to be buried deeper. Derek had to admit that he actually looked forward to these appointments. Not only did he get paid well but he also didn’t have to pay for a gym membership.
‘The Dentist’ was probably one of his most attractive clients if not the most. They typically would meet in his office after closing to fuck. Another one of those fetish guys, the Dentist would always greet him in his doctor jacket and nothing under it. The first time it really threw him on how hot he was especially underneath the jacket. He was well toned and had what looked like an eight pack. The good doctor also had an interesting array of tattoos that Derek made to certain to ask about. Tattoos were a real turn on for Derek and the fact that this guy had them made his dick jump with excitement. Only downside to the doctor was that he was super into oral and not receiving, giving. Now Derek loved a good blowjob as much as the next guy, and take his word for it, the doctor gave some of the best head in the city. The thing the man could do with his mouth was astounding and he smile when he was done, perfectly straight and pearly white. Derek’s only quam was not getting a chance to break in the good doc’s perfect ass.
One of his more laid back meetings was definitely ‘the Professor.’ They always met at a pub for drinks first. He and Derek would spend hours talking about books that they’d read and exchanging ideals. Eventually Derek would go back to his place where they would leave a trail of clothing from the door to the bedroom. The Professor was extremely attentive to his body. He would use his tongue to trace the lines of his figure, while teaching him new tricks that would make orgasms more intense. The guy was super into yoga and all the tantric bullshit that’s supposed to improve your sex life. Sometimes they would just stay up and talk. Derek didn’t really mind he was getting paid regardless, plus it was nice to have intelligent conversation for once.
About once or twice a month Derek would have an appointment with Robert or as he liked to called him, ‘the contortionist.’ Robert was very flexible, like circus freak flexible. The positions this guy could get himself into. Derek tried to limit himself to occasional meetings since every time he’d leave he’d need to take a day off to recuperate. Once he tried this one pose where Robert would sit on his dick and Derek’s legs would be wrapped around his head. It was so confusing but so much fun. He actually went home and told Isaac about it. Of course he had to find a clever way of working around how they’d even met but it was totally worth it. You can’t just have physically exhausting, mind-blowing sex and not tell your best friend about it.
But the client Derek looked forward to seeing the most had to be ‘the husband.’ Derek called him this because whenever they were together it was as if they’d been married for years. They would have a few glasses of wine and maybe talk about how their day had been, sometimes even cuddle on the couch while Derek would read to him. Derek had only seen him a few times but on the first night he introduced himself as Peter. He came to find out that Peter was a widower who’d lost his husband over a year ago. Derek would walked around his masterfully decorated home and see pictures of them together but never ask about, he’d simply wait for Peter to volunteer the information. Derek couldn’t help but think that the reason most of their time was spent not having sex was because of that fact. That maybe he just wanted the companionship, someone to spend cold nights with so that he didn’t have to be reminded that he was alone, that the love of his life was gone and he was still here in the house they shared with the ghost of memories. Either way Derek didn’t mind. He too enjoyed his company and wasn’t shy about letting him know it. Peter was a smart, attractive, witty man that seemed to actually get him on a human level. So much so, that when they did have sex, it was sensual and exhilarating. Sometimes it would go on for hours.
Derek would often catch himself lying in Peter’s arms, absorbing his scent, unaware of what time it was and forgetting that he had to return to reality. Tonight was no exception. Derek would maneuver himself off of the bed as not to rose Peter with his movements and quickly get dressed. He’d stumble his way to his car trying to put his shoes on in the process and make his way back to the apartment he shared with Isaac. Once in his room he’d strip back down until his was naked, take a shower and throw himself onto his bed. He’d look up at the blank ceiling and just think to himself.
Derek heard his doorknob turn and his door fly wide open. It was Isaac, of course, and he was drunk, something else that was to be expected.
“Dude you have got to get a new job, I feel like I never see you anymore.”
Derek laughed a bit under his breath.
“Aww! Do you miss me?”
“I didn’t say that.”
Isaac staggered over to Derek’s bed and kneeled down, taking a seat on the side facing the door.
“But I do you know.”
“You do what?”
Derek’s eyes were closed and voice was flat. He was halfway listening while trying to fall asleep. Isaac would often drunkenly wander into his room and try to have heart to heart talks when he was like this.
“Miss you.”
He turned to look at the back of his head. Isaac’s eyes glossed over as he stared into the darkness outside of Derek’s door.
“You’re my best friend but I feel like I never see you anymore.”
As annoyed as Derek was by the fact that Isaac picked now to come into his room and try tell him how he was feeling, he couldn’t help but feel bad. He had been working a lot and with the exception of classes, they hadn’t really seen each other in like a week.
“Well, maybe we can do something this weekend.”
“I’d like that.”
Isaac threw his head back onto his bed.
Well that didn’t take long.
He’d passed out on his bed. It wasn’t the first time and it probably wouldn’t be the last. Derek pulled on a clean pair of boxer briefs and lifted him onto his bed. Isaac really wasn’t that heavy so it wasn’t a hassle, plus his bed was plenty big enough for the two of them to share.
Derek was actually looking forward to having the weekend off. It’d been a while since he’d had time for his personal life. Between escorting and school he was fully booked. Luckily for him, with his new client list he didn’t have to deal with random John’s out of the blue.
His eyes had only closed for about a second but of course that’s all the time it needed. He was jerked back awake by the buzz of his phone against his nightstand.
[1 NEW TEXT MESSAGE]
Duncan: last minute job Saturday. 9PM Beacon Hills.
Looks like he was going to have to cancel again.
--
Stiles stared at the e-mail of escort ads at least once a day for a good fifteen minutes. When Scott first suggested it, the idea was out of the question absurd. But now, approaching the end of senior year, all bets were off. There was no way in hell Stiles was going to go his entire high school life a virgin. At least not when there was something he could do about it.
It took him awhile to warm up to the idea. Hell it’d taken him a full week after deciding to go through with it to even call and set up an appointment with Red.
Stiles could barely remember the conversation. It was all just a blur, as if his mind was trying to block out a trauma. The bits he did remember were that the person’s name was Red or maybe that their color was red? It was fuzzy. He remembers that they were going to be at his house at 9PM sharp, they were sticklers for punctuality. That’s pretty much it.
Stiles was lucky enough for his dad to be pulling an all-nighter working with State Police to try and find some criminal that was going around cutting people in half. He was alone pretty much all day which gave him the perfect opportunity to clean and rearrange his room.
He had to have moved the bed a good ten times before settling it back where it started off. He was nervous. Anyone with a pulse could tell that. He needed everything to be perfect: he’d taken a shower (twice), changed clothes (four times), checked the box of condoms for punctures (three times) and brushed his teeth (four times). If anything was going to go wrong it wasn’t going to be his fault.
The doorbell rang with a ding that seemed to resonate through Stiles whole body.
Okay. This is it Stiles. Don’t blow it.
He raced down the hallway and gotten right at the head of the stairs when he heard the second ding. His feet were clumsy; he walked half of the way and fell down the rest, hitting the floor at the bottom with a loud thud. Stiles was glad no one was around to see that as he picked himself up and dusted off his shirt.
Stiles took in a deep breath, placing his hand on the knob and turning it slightly. Breathing out, he tugged the door open to reveal a young man bathed in the light of his porch. He wore a black leather jacket and a red t-shirt with worn black jeans. His hair had a shine to it from the light, most likely reflecting off of a product that he used. The man wasn’t looking at him but down at his feet, his hand inside one another as if to conceal something.
Without looking up he greeted Stiles.
“Hi, my name is Philip and I’ll be you pleasurer this ev—“
His words cut off as he slowly lifted his gaze up to get a look at the boy in the doorway.
Stiles couldn’t believe his eyes.
It can’t be, could it?
“Derek?”
“Stiles?!”