Stiles Stilinski loves sex.
He doesn’t just casually like sex, though. He fucks and gets fucked for a living. He grew up being told to do what you love and you will never regret your life, so he took that advice and made a name for himself. He went to college, majored in Business, even started to get his Master’s before he decided he didn’t need an MFA to define him. He gave himself the title ‘Personal Consultant’ and started his own business. He may sell his body for money, but that doesn’t mean that this is a life that he merely settled for. This was who he was, what he wanted to do. And he was damned good at his job.
Stiles led a mostly normal day-to-day life. He woke up by his alarm, hitting snooze at least three times before rolling out of bed. He always worked out first thing in the morning, otherwise his day would be thrown off completely. There was a gym in his building, a few floors down, that he went to. Thirty minutes on the treadmill, then weight training for another thirty; he always made a protein shake afterward, to keep his muscles from aching. The last thing he wanted was to be too sore for sex. Then he showered.
Showers were never a short ordeal for Stiles. He prided himself on his shower, with two shower heads and amazing pressure with enough room for two or more people. He tended to take his time when cleaning himself.
With a towel wrapped around his waist, Stiles made his morning coffee. It was rarely actually morning when he made it, more like two in the afternoon, but he called it his morning coffee anyway. It wasn’t until he had a pair of boxer briefs on that he even picked up his phone to check for messages. He didn’t open a single one of them until he was at least three sips into his coffee with the TV on in the background, CNN playing almost too low to hear.
Voicemails were always first, listened to as his Mac booted up. He wrote notes down on post-it notes as he listened. Cancelled appointments, requested kinks to negotiate, tests that had come back negative from possible future clients, numerous voicemails from his father asking him to call home when he got the chance. Stiles opened Google Calendar then, making changes where he needed to. He kept everything organized, using different colors for different clients. Each client had a Google Doc that listed their kinks, likes and dislikes, rate given per hour which differed depending on what was asked of Stiles, as well as their test results.
Stiles was a stickler for his clients being tested. Sometimes they asked for things a normal escort wouldn’t do, not if they wanted to keep clean. Stiles made sure that he stayed clean by having himself tested regularly. His Google Calendar let him know when his appointments to get tested were, since he had to go intermittently for all of the different tests. Stiles groaned to himself when he saw that he had an appointment at 3:30 with Dr. Deaton for some bloodwork.
Dr. Deaton was where Stiles sent all of his clients. It made Stiles feel safer that the same man testing him was testing everyone else that he slept with as well. Dr. Deaton knew Stiles’ profession, but he remained discreet because of the amount of clientele he got based on Stiles’ business. Stiles was almost done with his coffee as he skimmed over some emails when his phone rang. Stiles stood up from his seat at the bar as he answered.
“Morning, Allison,” Stiles said as he cradled his phone between his cheek and his shoulder as he emptied the rest of his cooled coffee down the sink, rinsed it, then put it in the dishwasher.
“Afternoon, boss,” Allison replied with a hint of laughter. She was his personal assistant, along with his best friend’s fiancée. Basically, he couldn’t have asked for someone better to help him keep his life together. Stiles rolled his eyes at her as he made his way into his bedroom.
“I’m on my way to Deaton,” Stiles said, letting her know that he had, in fact, looked at his calendar. He missed one appointment, one, and he can’t be trusted not to fuck up again.
“Aw, I am so proud of you, reading your own calendar like a big boy,” Allison cooed sarcastically. “I was calling you because you have a new request that came in.”
“Keep talking,” Stiles said as he put Allison on speakerphone so that he could get dressed.
“He is early thirties, mysterious, handsome-”
“Allison, is he there right now?” Stiles asked, exasperated as he buttoned up the cuffs of his shirt.
“Mmhm,” Allison drawled. “He’s waiting in the lobby. I told him you weren’t coming in until later, but he said he would wait.” Stiles’ brow furrowed. He didn’t like when john’s were stalkerish, or possessive. It was a total turn off for him, and Allison knew it. Stiles chose his john’s carefully. This one he wanted to talk to personally before he let any paperwork be signed.
“Send him away with my card. I’m not coming in until later today,” he replied. “Snap a picture of him before he leaves, though.”
“Sure thing,” Allison said before she hung up. Stiles messed around in his Google Docs, adding in a few notes to the doc he had of the john he had spent the previous night with. He completely lost track of time, jumping when the picture came through from Allison. The potential john was, in fact, handsome, albeit a bit broody. Stiles frowned at the picture, his face matching the john’s.
He laughed at himself; it was the little things in life that amused him, apparently. He put his shoes on, grabbed his coat and scarf, then headed out the door, making sure to lock it and jiggle the handle twice before walking down the hallway towards the elevator.
Living in New York City had its perks. For instance, Stiles loved that he didn’t need a car. He didn’t like driving with the streets so packed full of people, taxis driving haphazardly and dangerously. He liked that, no matter what the time, he could order in food. Actually, he liked the fact that he could order anything he wanted to be delivered. If he wanted to, he didn’t have to leave his apartment building. Some of his days off, he did exactly that. Being social was what he did for a living. Not all john’s just wanted a fuck. Some wanted a nice dinner, someone to talk to, or not go to the movies alone. Sure, most of the time it ended with Stiles on his knees, but then again that was his favorite part. He didn’t care for the faux dates where older women dangled him off their arms as if he were a pet; a young boy to show off.
In a way, he was, but that didn’t deter him.
It was his appeal and he knew it. He had a certain look that he knew others craved. Men liked the shape of his mouth, the hollowness of his cheeks as he sucked them off, the feel of his ass tight in their grip. Women liked his pretty, although masculine, face. He had a few cougars on his list, mostly wanting to be seen with a young man, to be flirted with at a fine restaurant, for him to eat them out for an hour or so.
Stiles licked his lips as he shoved his hands into his coat pockets. It was late fall and the wind was already biting as he walked down the street towards the subway. Deaton’s office was across town, closer to Stiles’ hotel room.
It took Stiles three years, but he bought himself a penthouse to host his clients. It was the complete opposite of his actual apartment, decked out in fine leather couches, a king-sized bed, a fully stocked mini-fridge, and enough condoms and lube to last him a year stashed in the massive bathroom. His own apartment was small in comparison, excluding his shower. He shares his apartment with a subletter by the name of Isaac, but he rarely sees him due to their opposite schedules. Stiles was more of a night owl, for obvious reasons. Stiles thinks he has only seen Isaac a total of five times in the two months that he had been living with Stiles.
Deaton’s waiting room always looked the same with its months old magazines with an address scratched out of the bottom, along with the most uncomfortable chairs known in existence. They always made Stiles squirm in his seat, never finding a position that was the least bit comfortable. The nurse always gave Stiles a look, but he only shrugged it off as she called his name, beckoning him to follow her into a room. He hopped up onto the examining table without a word, giving her a smile as he rolled up his shirt sleeve enough so she could take his blood pressure. She knew why he came in once every two weeks or so. She could judge him all she wanted, but Stiles saw her eyes raking over him. He watched the pump as it took his blood pressure, giving himself a small smile.
“The doctor will be in to see you shortly,” she said before shutting the door, leaving him in the room alone. Stiles pulled out his phone, checking his messages once more. He wasn’t at all surprised to find an email from whom he assumed to be the john who had been loitering his and Allison’s office. It was the normal greeting, awkward and unsure, asking for an appointment. Stiles shot him a reply.
He tended to meet potential new john’s on neutral ground somewhere, like a coffee shop or the park. Since it was cold out, Stiles opted for a Starbucks. He checked his calendar quickly, giving him a few options of meeting times to choose from. By the time he hit send, the door opened and Dr. Deaton walked in.
“Good to see you again, Stiles,” he said with an easy smile. Stiles could never tell if he was being sincere or sarcastic, but he smiled back nonetheless. The doctor’s appointment itself never took long. Drop the pants, get checked over, get blood drawn, chat about being safe (and sometimes not), pay the front desk, stop by Starbucks to get a ‘you did good with the needles’ coffee, head to the office.
Stiles’ office was close to the hotel, just a few blocks away. He mainly needed a place for him and Allison to meet up, somewhere to store paperwork and meet clients if need be. It was small, enough space for desks for himself and Allison and a couch. Stiles loved that couch, a lot. It was his napping couch, as well as his ‘meet the client’ couch.
By the time he walked into the office, it was veering on 5pm. Allison was sitting at her desk, obviously on Facebook. She didn’t even try to pretend that she was working. Stiles shrugged off his coat, hanging it up on the hook behind the door, then handed her a coffee, which he bought her when he bought his own.
“Awww, a ‘Stiles hates needles’ coffee! How sweet of you,” she teased as she took a sip, smiling up at him as she swung back and forth in her swivel chair. Stiles gave her a fake glare as he sat down at his desk, turning on his computer.
“See if I get you a coffee next time,” Stiles mumbled as he typed in his password.
“I mean, I am pretty sure I should be the one getting you coffees.”
“Semantics,” Stiles said, sticking out his tongue. He sighed as he opened his email. He turned to Allison, pointing at the fifteen he got from the time he was at Deaton’s until now. “What the fuck, Allison?”
Allison shrugged, taking another sip from her coffee.
“Someone is Mister Popular.”
Stiles groaned as he raked his fingers through his hair. He pulled up his calendar.
“What have you already figured out without me?” He asked. Allison had access to his work email address, so that she could input dates and appointments into his calendar herself. Stiles would be running around with his head cut off without her, basically, and he knew it.
“Well,” Allison started, pulling up the calendar herself. “I’ve cleared a few dates where there were cancellations, added in the client meeting that you started to set up this afternoon-”
“He responded already?” Stiles asked, clicking through his emails, trying to find a response.
“Mmhm,” Allison said, typing away at something. Stiles’ eyes skimmed across the email. He was meeting this possible future client tomorrow. Stiles raked his teeth across his bottom lip as he read the email that Allison sent as him, stating that tomorrow would work for him. She even said what Stiles would be wearing. He gave her another glare.
“I hate the red shirt.”
“Too bad!” Allison said in a sing-song voice. “You look good in it. He’ll want to just eat you up.”
“I’m supposed to be eating him up though.”
“I don’t know why I work for you,” Allison said with a roll of her eyes. “The things I know about you-”
“How about,” Stiles said as he swung around in his chair, slouching down in it as he looked at her, “we don’t discuss what we know and don’t know about each other’s sex lives?”
Allison grinned at him.
“So last night Scott and I tried something new-”
“La La La!” Stiles shouted, sticking his fingers in his ears. “I can’t hear you talking about my best friend.”
“And he bought me this toy-”
“Oh my god,” Stiles groaned, turning around. “No.”
“And holy shit, Stiles-”
“Stop, cease, desist,” Stiles begged in faux agony. He started laughing, his head thrown back and hands clenched at his stomach. “No, but what toy was this? Do I want one?”
“I think you might, actually,” Allison said honestly.
For the evening, Stiles was booked for a meal with a middle-aged couple and then a rendezvous with them at his penthouse where the husband liked to watch as Stiles fucked his wife. They were a bimonthly gig that paid handsomely for his time, so he was willing to forego his usual hesitance at voyeurism. He’d rather have everyone in on the fun.
But his job was to do what was asked of him. And he did it well.
Stiles was barely in his office an hour before he left for the penthouse to change and get ready. The good thing about having a place in a hotel is the fact that they cleaned it as if it was just another room in said hotel. Fresh towels and sheets awaited him every time he walked in. Stiles didn’t need to do much in the way of getting ready. He shaved, which he hadn’t done earlier, brushed his teeth, then changed his clothes. The couple he was meeting always dined at five star restaurants that you needed to book reservations at months in advance. Stiles supposed it was to show him how rich they were, how he was a toy for the wife, a fun night out. Stiles didn’t care, though. He always ordered the most expensive wine on the list.
They always ordered the bottle.
Wining and dining was easy. Schmoozing was nothing. All smiles and smartly timed winks, a foot teasing slowly up a leg under the table, fingers grazing along a thigh. Stiles thought of it as foreplay. Foreplay to Stiles was the best part of sex. He liked licking, sucking, fingering, tasting. Everyone was different, had different buttons to push. Stiles excelled at finding those buttons.
This would be Stiles’ fourth ‘date’ with this couple. Before heading out he reread their file, brushing up on Her likes and dislikes. Stiles raised an eyebrow. Apparently He enjoyed it the most when Stiles made eye contact with Him. Stiles would definitely have to remember that later, because this couple tended to tip well the more times Stiles made Her come.
All in all, Stiles’ night was over by eleven. They paid by card, swiped with Stiles’ handy dandy iPad GoPayment processor. Voilá, money in the bank. Afterwards, Stiles laid in bed, covers thrown on top, head propped up on a pillow as the TV played in the background. He had showered, and was laying around naked as he played Candy Crush on his iPad. Eventually, he moved, gathering his things for the night. He took a candy bar from the mini-bar as he walked out.
He dialed his father’s number as he headed towards the elevator, putting his headphones in as it rang.
“I was hoping you would call,” his father’s voice said over the receiver. Stiles couldn’t help but smile.
“Sorry it took me so long.”
“It’s alright, I know you are busy. Late night at the office?” His father asked. Stiles bit his lip as he tapped his foot against the tiled floor.
“You could say that,” Stiles said with a sigh. He never had it in him to tell his dad what he did for a living. There just wasn’t really a way to tell a Sheriff that you grew up to be a escort, albeit a very well-paid one. “How is Miranda doing?” Stiles hated asking about his stepmother, but knew it made his father smile when he did.
“She is doing well, started her new hours at the hospital. We are working the same shifts, so we can spend more time together.”
“That sounds awesome, dad,” Stiles said as his shoulders slumped. His father met Miranda when he got shot while on duty a few years back, when Stiles was away at college. Why Stiles chose Columbia, he didn’t know. It meant being on the opposite side of the country from his father when he had almost died. Miranda had been his doctor. She had been the one to save his life as Stiles sat in his dorm crying because he didn’t have enough money to fly last minute across the country. “You deserve to be happy.”
“And so do you, son. Miranda and I worry about you. Have you met anyone new?” Stiles’ eyebrow quirked upwards as he shook his head, his fingers rubbing at an eye.
“No, no one,” Stiles told him truthfully. “I mean, not in a relationship sense.”
“You don’t have to explain to me,” his father laughed. “I was young once, before I met your mother.”
The conversation went silent at the mention of Stiles’ mother, who died his freshman year of high school. Stiles let out an audible sigh as the elevator dinged, the doors opening at the ground floor.
“I love you,” his father told him. Stiles gave a small smile as he pulled his coat closer to himself.
“I love you too, dad. I will try to call more often.”
“Don’t run yourself into the ground with work.”
By the time Stiles got home, it was barely midnight. Stiles took a quick shower, then pulled on a pair of sweats, an old t-shirt, and a Beacon Hills Sheriff’s Department sweatshirt that he had stolen from his father before he moved across the country. It was way too early to go to bed, so Stiles decided to watch something that he had DVR’d. He got a beer out of the fridge and made himself comfortable on the couch. He fell asleep with his beer in his lap, head tilted back against the couch cushion, mouth hanging open. The door to the apartment opening and closing woke him with a start, his eyes shooting open in surprise.
“Whoa, sorry,” Isaac said as he shrugged off his coat. “You aren’t normally home.”
“It’s fine,” Stiles said as he wiped at his mouth. He looked at the clock on the microwave in the kitchen. It was one. “I got home a bit early, must have dozed off.” Stiles stood up, walking over to the sink to pour out his now warm beer. He hated warm beer. It reminded him of college when no one had enough money to buy good beer so they always ended up getting drunk on Miller Lite, or something equally as gross. “You’re out late,” Stiles pointed out as he raked his fingers through his hair as he leaned against the kitchen counter.
“Had drinks with some friends, I’m going to regret it when I have to be up in five hours though,” Isaac said with a smile as he walked into his room. “Night.”
“Night,” Stiles called out after Isaac’s door was already shut. Stiles took a deep breath before he pushed himself away from the counter. He locked the door, turned off the TV and all the lights, then headed to bed. Stiles never fell asleep easily. He curled up underneath the sheets, his iPad making his room glow in a cool light as he read until he fell asleep two hours later.
The next day, he showed up at the coffee shop fifteen minutes early, ordering himself a venti. He wore the red dress shirt, just like Allison told him to, along with grey slacks and a tie. His jacket was folded over the back of his seat, his sleeves rolled up and legs crossed as he sat waiting, sipping at his coffee as his eyes scanned Google Calendar for the rest of his day’s appointments. He had dinner with Scott and Allison planned, then an appointment set at nine with a client whose paperwork had just gone through a few days ago.
Someone cleared his throat, causing Stiles to look up. The man whose picture Allison had sent to Stiles stood above him with a cool smile across his lips.
“You look... stunning,” the man said with ease. Stiles stood up to shake his hand.
“Nice to meet you, Deucalion?” Stiles asked, in case he had said the name incorrectly. His potential client nodded at the pronounciation, his thumb stroking the back of Stiles’ hand before he released it. Stiles sat back down, straightening his tie before motioning for Deucalion to join him. Stiles put his hands in his lap, head tilting to one side as he looked Deucalion over. He had a number of johns just like him. Stiles looked to Deucalion’s left hand, noting that he didn’t have a wedding ring on. Most clients were married, looking for an escape for a short time, or someone to be rougher with, someone that would do the things that their significant other wouldn’t.
There was something about the fact that others trusted Stiles with their kinks and the fact that they didn’t trust anyone else with them that made everything worth it. Stiles appraised Deucalion for a moment, wondering what exactly was going to be asked of him this time.
“Your assistant tells me that you have experience with BDSM,” Deucalion starts. Stiles smirks, his head nodding only once.
“With both being a Dom and a Sub,” Stiles states as he sips his coffee. “Which role are you looking for me to fulfill for you?”
“Sub,” he responds immediately. Stiles closes his eyes momentarily, imagining himself under Deucalion, collared, hands bound behind his back.
“That can be arranged,” he said easily. “Allison can write up a contract. How often were you thinking, monthly, bimonthly?” Stiles asked as he pulled his iPad out of his bag.
“Weekly.” Stiles’ eyebrows arched upwards in surprise as his fingers slid across his calendar.
“That may be a problem, but let me see.” He hadn’t been expecting that. “Are evenings the only time you are available?” His evenings were what always filled up the fastest.
“Actually, mid-morning to early afternoon would work best for me.” That certainly was doable. Stiles scanned his calendar quickly. He knew from experience what Deucalion was going to be like in bed: fierce, unrepentant, unyielding. He needed to make sure he had a day to recover afterwards.
“Do Tuesdays at noon work for you?” Stiles asked. He almost always took Wednesdays off.
“We can pencil you in for Tuesdays, then. Tell me more about what you want from me, and then we can discuss testing, safety, and our meeting place.”
The meeting itself lasted almost an hour. Stiles gave Deucalion one of Deaton’s cards for a referral. He made it known that there would be no appointment with him until the paperwork came in, but that his Tuesdays at noon would remain blocked out for him. They decided that Stiles’ hotel suite would work for what Deucalion was looking for. It wasn’t uncommon for Doms to want to be in their own spaces, but he was open to Stiles’. They discussed payment, deciding on cash. Stiles didn’t mind cash, although getting over a thousand dollars all at once was a bit cumbersome. He asked for larger bills, to make it easier.
On the way to his office, Stiles stopped and picked up a late lunch for himself and Allison. When he got to the office, he was greeted by his best friend.
“Scotty! I wasn’t expecting you,” Stiles said as he put down his and Allison’s lunches in order to wrap his arms around Scott, who did the same to him. “I would have brought you a sandwich, too.”
“I’ll just eat half of yours,” Scott teased. “I just stopped by to say that tonight is about celebration!” Scott clapped his hands together, looking at Stiles expectantly. Stiles rolled his eyes then turned to his desk to drum roll. Once Scott was fully satisfied with Stiles’ drum rolling skills, he pat Stiles’ back.
“I got the job! I am officially quitting that shit show and moving on up to the world of marketing!” Stiles beamed as Allison screamed, clapping her hands as she stood up in order to give Scott a hug and a kiss. “I get my own office and everything.”
“I am so getting you a desk plant,” Stiles joked.
“I don’t want a desk plant,” Scott said seriously.
“Then I’m buying you some scotch to keep in the bottom drawer of your desk for when I visit.”
“That sounds more like it,” Scott said as he put an arm around Allison. “So I made reservations tonight at seven, since Allison told me you had an appointment at nine.”
“Perfect,” Stiles said as he sat down to dig into his lunch. He was starving. “I’ll be there.” Before Scott left, though, he took a bite out of Stiles’ sandwich.
“So,” Allison said as she unwrapped hers. “How’d it go?”
“I need you to write up a BDSM contract for me,” Stiles said as he chewed, then swallowed. He wiped at his mouth with his thumb, then licked it. Allison didn’t look pleased.
“Last time that didn’t go well,” she pointed out. Stiles shrugged his shoulders.
“Maybe we should assess the contract or hire a security guard for the night, just in case.”
“Hmm,” Allison said as she used her mouse to click around her computer as she held her sandwich with the other hand. “Boyd does private security.” Stiles blanched.
“I am not having Boyd around while I am on all fours, tied down, or collared or-- no. Just no.”
Allison laughed openly, twisting in her chair.
“Well, I guess I have my afternoon cut out for me.”
“Also block out Tuesdays at noon for me for the foreseeable future.”
“Noon? Really?” Allison asked, clearly judging the timing. “Did he mention what he wanted?”
“Rough play,” Stiles said after swallowing a bite of his sandwich. He walked over to their mini-fridge, grabbing a bottle of water for himself. He offered it to Allison first, before taking a sip.
“You have a Tuesday evening...”
“Yeah, well...” Stiles said as he sat down, brow furrowed. “But that is dinner, fully clothed, and all about me servicing them. They like toys,” Stiles pointed out. “It will be fine,” he assured her. “If it doesn’t work out, it doesn’t work out. I will drop them if they are too rough,” he said with a shrug. It was as simple as that, really. It would take at least a week for Deucalion to see Deaton, then a few weeks for the results to come back. He had time, and even then he could always refuse the client. But he was at least willing to give him one appointment.
After finishing his sandwich, Stiles took a nap on his couch. He fell asleep to the sound of Allison typing. She shook him awake at five by pinching his nose. Stiles swatted at her as he groaned.
“No,” he mumbled.
“Yes, let’s lock up. Shower then meet me at the restaurant. I sent you an email with the address to give the cabbie.”
“You’re amazing,” Stiles said as he sat up, yawning. He gathered his things then waited as Allison locked the door, hailing a cab for her before walking himself to the subway. He had time for a quick shower. He dressed for his appointment, ridding himself of the red button up, going for a more relaxing dress shirt and cardigan combo.
As he walked out of his room, he noticed that Isaac and a friend were watching TV in the living room.
“You look snazzy,” the guest said.
“Thanks,” Stiles said as he grabbed his coat from the rack by the door.
“This is Cora,” Isaac said by way of introduction. “She lives next door.” Stiles smiled at her.
“Nice to meet you, Cora.”
“The pleasure’s all mine,” she practically purred as she gave him a once over. Isaac rolled his eyes as Stiles wrapped a scarf around his neck, one eyebrow cocked.
“I’m going to dinner... my best friend got a job promotion.”
“Tell him I said congrats,” Isaac said out of politeness. Stiles nodded as he grabbed the doorknob. Maybe he should try to include Isaac more, ask him to do things with him. But not tonight; tonight was about Scott.
“Will do,” Stiles said as he walked out the door.
Stiles arrived at the restaurant five minutes late and was ushered straight to a table, as his coat was taken from him, where he found himself faced with not only Scott and Allison, but also Boyd and Erica, two mutual acquaintances.
“Boyd, Erica,” Stiles said with a smile. Before sitting down he kissed Erica on the cheek, then patted Boyd on the back. “Wasn’t expecting to see you two here.”
“When I called Boyd’s work looking for the security detail I told him about Scott’s promotion and told him to bring Erica,” Allison said as Stiles took his seat. They ordered drinks to start with, Stiles got his Jack and Coke, which he nursed until their food arrived. With dinner he had a glass of wine, cutting himself off with just the one. The last thing he wanted was to show up to an appointment smelling of alcohol.
“How is the business going, Stiles?” Erica asked, mid-sip for Stiles. Stiles choked a bit, holding his hand to his chest. He looked to Allison to cover for him.
“It’s going well, pretty much booked solid. Stiles is an amazing consultant.”
Stiles grinned at her, winking.
“Are you taking referrals?” Erica asked. “Because I have a friend who needs to get laid, like, yesterday.” Stiles coughed, shaking his head. He really shouldn’t have taken that bite. Erica always gave him cheek. “What?” She teased, rubbing his back. “I heard you’re pretty good.”
“Oh, I am,” Stiles assured her. “But I think my plate is currently full,” he joked, pointing down at his empty plate. “Besides, that would be weird.” Erica shrugged nonchalantly.
“Fine with me,” she said as she took another sip of her wine.
It wasn’t that Stiles was surprised whenever friends of his who knew what he did tried to set him up with appointments of acquaintances, it was more that they never seemed to stop doing it. One would think that the fact that he fucked for money would be the white elephant in the room, that no one would mention it, but no. It was brought up all the time, as if it was nothing. He should feel at ease, knowing his friends didn’t care what he was doing with his life, that they were okay with it, but he wasn’t. Something just felt off about it, like Erica’s insistence about this so called friend of hers who needed a lay.
It always felt as though she was trying to set him up on a date, rather than to fill his calendar with another appointment. That was where he felt off with the entire situation because Stiles didn’t do relationships. He didn’t fuck people and have feelings for them, he never did. He tried dating in high school and in college but it wasn’t for him. Dates where you held hands, took walks, snuggled and cuddled after sex just wasn’t for him. He didn’t even like kissing that much, if he was being completely honest with himself. It was a means to an end, a build up to sex that wasn’t a blowjob and most certainly wasn’t rimming. He’d rather lick someone until they screamed than play tonsil hockey with them.
“This was fun,” Stiles said as he finished his glass of wine. “But I have to get to my nine o’clock.” He shook Boyd’s hand, kissed both Erica and Allison’s cheeks, then hugged Scott. “Congrats, man.”
“Thanks, bro,” Scott said as he sat back down after their hug. “We need to hang out sometime!”
“Have Allison block off some bro time!” Stiles called over his shoulder. He checked the time on his phone, realizing he didn’t have much time before nine.
He made it to the suite ten minutes before his appointment was due. He hung up his coat and scarf, then practically ran into the bathroom to brush his teeth. As he gargled mouthwash he opened a bottle of wine to let it breathe, in case the john wanted a glass. Stiles even thought about pouring himself a glass. This john was someone whom he had been looking forward to finally having an appointment with.
His initial meeting with him had been awkward, but in a way that Stiles found rather endearing. It was obvious the guy knew exactly what he wanted, but had been embarrassed to talk about it. As if Stiles would turn him down. Sometimes johns came to Stiles with out of the norm requests, like Deucalion. Stiles was not a BDSM escort, but he had done it in the past and had no problem with being a Dom or a Sub to someone. But this john asked for something rarer for Stiles.
As an escort, usually come play was out of the question. Barebacking was dangerous, even while in a relationship. The guy had a kink, and Stiles could tell that he wasn’t getting off with whoever they were currently with, if anyone. Something about him piqued Stiles’ interest. It could have been his surly face set in a pout, or the size of his muscles that could be seen through his shirt easily, or the unique color of his eyes. Whatever it was, it got Stiles to agree.
They set the terms and the price. The paperwork all came through clear, everything was a go.
And now Stiles had to wait for him to arrive. It was almost five past when there was a knock at the door. Stiles answered it like he always did: barefoot. There was something about being dressed up, sans shoes and socks, that made him feel more comfortable.
“Mr. Hale,” Stiles greeted with a smile. He got a brief nod in response as he opened the door wider to invite him in. “Would you like a glass of wine?” Stiles offered. He was met with silence, so he walked over to the counter where it was breathing, holding up a glass to Mr. Hale.
“Sure.” It was a curt response, but Stiles didn’t take it personally. He poured the glass, offering it to Mr. Hale.
“Would you like me to call you Mr. Hale, or do you prefer something else?” Stiles asked in an attempt to break the tension he felt rising in the room. He was used to new clients being uncomfortable with how to get things started.
“Derek is fine,” he replied. “What... what should I call you?”
“You can call me whatever you want,” Stiles said warmly. “But I prefer ‘Stiles’.”
“Okay,” Derek said with a gulp. Stiles poured himself a small glass, ushering them to the couch.
“Did you find the penthouse alright?” Stiles asked, trying to break down Derek’s walls a bit. It was always easier to segue into sex if they talked a bit beforehand, reminding the client what they had negotiated, what they were getting. It always seemed to set the mood.
Stiles sat down after Derek, close to him, with a knee up on the couch. He was practically in Derek’s lap, with a hand near Derek’s shoulder, a finger trailing across his shirt. He was wearing a plain black t-shirt and dark jeans. Stiles’ eyes honed in on Derek’s lips as he licked them before taking a sip of wine as he nodded his head.
“The directions that were given worked.”
“Good,” Stiles said with a smile. He set his untouched glass down on the coffee table. He wanted use of both his hands. “I know we discussed terms at our previous meeting,” he started to say as his hand slid across the expanse of Derek’s shoulders, fingers catching for only a moment on the nape of Derek’s neck, his lips brushing against Derek’s ear. “But I want everything out on the table before we start.” Stiles placed his free hand on Derek’s thigh, palm rubbing lightly up and down.
“Okay,” Derek rasped, clearing his throat afterwards, watching Stiles’ hand move with rapt attention. Stiles didn’t hide his smirk, instead he nipped Derek’s ear, then kissed it as his hand slid further up Derek’s thigh. Derek spread his legs in response. With eyes lidded, Stiles breathed him in.
“You want to use my mouth,” Stiles began, his thumb rubbing across Derek’s crotch, “you want to hold me still as you fuck it, you want to come on me.” Derek groaned, his eyes closing, his mouth open, Adam’s apple bobbing up and down as he swallowed. Stiles licked up his neck, his hand gliding away from Derek’s crotch to his wine glass. Fluidly, Stiles took it from him and set it down on the coffee table, then straddled Derek. Stiles cupped Derek’s face in his hands as Derek grabbed him by the hips. Stiles pressed a thumb against Derek’s lips, letting out a short gasp when Derek’s mouth opened for him, sucking in his thumb greedily. Stiles rolled his hips down, grinding himself against Derek. “Is that what you want?” Stiles asked him as he bent forward, taking his thumb out of Derek’s mouth in order to hover his own lips over Derek’s, teasing him.
“Yes,” Derek replied. Stiles kissed him then. Derek’s hands immediately slid down and back, cupping Stiles’ ass. Stiles groaned into the kiss, tugging on Derek’s hair. He couldn’t help but register the groan of pleasure that escaped from Derek’s lips as he did it. Just for good measure, Stiles did it again. Derek bucked his hips upwards, showing Stiles just how hard he was already. “I want your mouth,” Derek growled.
Stiles bit down on Derek’s lip, tugging it as he ended the kiss. Derek’s grip on his ass hadn’t let up, and he had a finger pressed against his hole, right through the fabric. Stiles pushed back, raking his teeth across his bottom lip.
“You wanted to hold me down, right?” Stiles asked, feigning being coy as he got off of Derek. He took hold of Derek’s hand, guiding him over to the king-sized bed. Stiles stood in front of him, taking his time unbuttoning Derek’s shirt and discarding it. He appraised Derek’s muscled form, his fingers grazing over a nipple before kissing Derek again, opening his mouth for him. Derek moved, his hands cupping Stiles’ face to deepen the kiss further. Stiles tugged on Derek’s belt, then, flinging it across the room as Derek backed Stiles up against the bed. He bent his knees, falling until he sat on the bed, his fingers deftly ridding Derek of his pants, shoving them down his thighs. Stiles looked up at him, his mouth hanging open slightly, to take a look at his face.
Derek already looked blissed out, his fingers raking through Stiles’ hair as Stiles leaned forward, mouthing at the fabric of Derek’s boxer briefs, outlining Derek’s erection with his tongue. Stiles grinned against him as his fingers hooked around the fabric, inching it down just enough to reveal the head of Derek’s uncut cock. Stiles’ mouth watered at the sight, his tongue darting out to lick at it. He pushed the fabric down Derek’s thighs, his fingers wrapping around the shaft, stroking it. He watched the head of Derek’s cock appear only to disappear seconds later. On a downward stroke, Stiles put his mouth around Derek’s cock as he cupped Derek’s balls with his other hand.
With a snap of his hips, Derek slid himself down Stiles’ throat. Stiles pulled back, gasping for air as he looked up at Derek. Without a word, Stiles went back down, taking Derek into his mouth again, opening his throat for him. Derek’s grip on Stiles’ hair tightened as he started fucking into Stiles’ mouth. Stiles’ hands dropped to Derek’s thighs, holding on as his eyes began to water. This was what Derek wanted, this is what got him off. Stiles tried to breath in through his nose, but Derek’s pistoning hips were too much. Stiles tapped Derek’s thighs, asking for air. Derek obliged him.
Stiles coughed, sucking in as much air as he could as spit and precome slid down his chin. He wiped at his mouth all the while continuing to jack Derek off.
“Thought you wanted to pin me down,” Stiles said through heavy-lidded eyes as he looked up at Derek. He stuck his tongue out to lick up Derek’s shaft, but at the last moment Derek yanked Stiles’ head back, pulling him away from his erection. Stiles moaned open-mouthed as Derek stepped further away from him. His grip on Derek’s erection slipped away as well, leaving him on the bed alone.
“On your back, then, head facing this way.” Stiles practically jumped onto the bed, still fully clothed. “Take your shirt off,” Derek demanded as he started jacking himself off. Stiles complied, tossing the cardigan first, then unbuttoning his collared shirt with quick, nimble fingers. He was hard, almost achingly so, but did nothing to relieve himself. This was about the client, it always was. This was no different.
Stiles made himself comfortable, giving enough room so that his hands could grip the edge of the bed, he gave Derek a look, then opened his mouth. Derek crawled onto the bed, knees on either side of Stiles’ shoulders.
“You ready?” Derek asked as he looked down at Stiles. Stiles nodded his head, extending his neck just a bit so that he could lick at the head of Derek’s cock playfully.
“Fuck my mouth,” Stiles pleaded as he pressed his head against the mattress, getting a good angle for Derek’s cock to slide down his throat. Stiles breathed in through his mouth, before Derek’s cock was there, filling him. He relaxed his throat, not letting himself choke on him. Derek’s hands were on Stiles’ body, holding him in place as he began to move. Stiles’ hands moved to wrap around Derek’s thighs, fingernails digging into the flesh as his pace quickened.
Stiles tapped out when he needed to breathe. Derek only let him breathe in once before plummeting back in. Stiles arched his body upwards as spit poured out of his mouth with each gasp of air that was allowed to him. Tears were streaming from his eyes as Derek fucked his mouth relentlessly.
“God you feel so good,” Derek preened as his palm rest against Stiles’ throat so he could feel the movement of his cock sliding up and down Stiles’ throat. “Your mouth is so fucking perfect.” Stiles raked his fingernails up Derek’s thighs as he spread his own legs further apart. The pressure in his groin was becoming unbearable, he needed release. “You’re doing so good.”
Stiles dug his toes into the bed, pushing at Derek’s thighs. He sputtered for breath as Derek backed away enough for him to get air, his cock dangling inches from his mouth, dripping wet with spit and precome. Stiles coughed, his chest heaving from the lack of air. He was sure that Derek was going to fuck his face more, but he was surprised when, instead, Derek took hold of his erection and began stroking himself. “Going to come on you,” he rasped. Stiles licked his lips, closing his eyes as he ran his fingers up and down Derek’s hairy thighs, his nails catching every so often.
“I want that, come on Derek,” he pleaded. Hot, sticky come shot across his face, catching on his lips and nose. Stiles could feel it dripping down his chin, his lips parting as Derek spasmed above him, moaning his name. He let Derek ride his high, his finger smearing come across Stiles’ cheek. Stiles turned his head enough to catch Derek’s index finger, tasting him. He moaned, his own hand sliding down his chest as he took Derek’s finger further into his own mouth, his tongue swirling around it. Stiles cupped himself through the fabric of his pants. He could feel the dampness of his precome. He soaked through his briefs completely.
Derek’s eyes flickered to Stiles’ apparent erection. Without another word, Stiles released Derek’s finger, then sat up. That was not part of the deal, not tonight. Derek paid for a blowjob and a facial. No matter how hungry his eyes looked for a taste of Stiles, he wouldn’t break protocol. He would need to schedule another appointment if he wanted something else.
Stiles walked into the massive bathroom, grabbing a washcloth to clean himself off with. He grabbed himself a plain white t-shirt to put on, always finding it easier to end the night clothed, to let the john know the evening was over. When Stiles walked back out into the room, Derek was almost fully dressed again. Stiles grabbed his iPad and his glass of wine, taking a sip of it. It tasted weird after having come in his mouth, but he ignored it.
Derek walked up to him, his face flushed from either their escapades or a sign of remorse for what he had just done. Either way, it wasn’t Stiles’ business. He handed Derek the iPad with the GoPayment app open, showing how much Derek owed him.
“If you liked that, be sure to call my assistant to make another appointment.” It was always awkward, the first time afterwards and Derek was no exception. He handed Stiles a card, which he swiped then handed back. Derek signed the receipt electronically. Stiles then sent it to Derek’s email address, which he had stored via Allison.
“Can’t we just make one now?” Derek asked him. Stiles’ lip quirked upwards slightly, pleased. He nodded his head, pulling up his Google Calendar.
“Of course we can,” he said congenially. He tapped around, finding a free evening. “Is this time good for you? Or-”
“I can do earlier. I work early in the mornings, until around three usually.” Stiles nodded, searching.
“How soon?” Stiles asked.
“How soon are you available?” Stiles’ cock twitched in his pants. He bit his lip to keep from moaning. Derek didn’t seem to notice, though, which was good.
“I am booked this week,” Stiles mumbled as he quickly searched into early the following week. Derek stepped nearer, looking over Stiles’ shoulder. Stiles leaned back against him, just because it felt good. Derek radiated heat, and Stiles always got cold after sex, even though his own erection was throbbing and on fire.
“Why not there?” Derek asked, pointing at a three-thirty spot the next Thursday. Stiles tapped it, then filled it in with Derek’s name.
“You have me for two hours,” Stiles said, catching Derek’s gaze with his own. “What do you want to fill it with?” It was Derek’s turn to grin.
“Do I have time to think about it?” He asked. Stiles was busy staring at Derek’s lips, but he nodded nonetheless.
“Email me any time this week and we can discuss what you want,” he said, shaking his own head slightly, breaking himself of his trance. Derek chuckled to himself, his hand grazing across Stiles’ back as he walked towards the entrance. Stiles put his iPad down, then rushed to join Derek to let him out.
“Next time, I am touching you,” Derek stated, his eyes flicking up and down Stiles’ body.
“Sounds fun,” Stiles admitted aloud. Derek and he shared a look, and then he was gone, walking down the hallway towards the elevator. Stiles shut the door, leaning against it for a moment before stripping off his clothes and getting into the shower where he jacked off, coming with two fingers in his ass, his forehead pressed up against the tiles of the shower as he panted.
He ended up balling his underwear up and shoving it into his coat pocket, going commando instead of wearing wet briefs on the subway. When he got home, he took two ibuprofen for his jaw, brushed his teeth, then crawled into bed even though it wasn’t even midnight. Before he went to bed, he saw that he already had an email waiting for him from Derek. With a smile, he shut off his iPad and went to sleep.