Work Text:
The bills were starting to pile up. Derek wasn’t sure how the hell he was going to get out of this one. Usually he was a fan of just ignoring a problem until it eventually goes away or at least until someone would step in and offered a helping hand. But those times are few and far between. These weren’t like the annoying frat guys at parties that wouldn’t stop shouting about chugging beers or the countless girls that ask him out on dates. Those were easy problems. Those he could ignore. Not these.
The red stamps on the tops of papers read ‘urgent’ or ‘past due’ kept staring him in the face. His eyes were beginning to gloss over at the vast quantities he owed in tuition. The price of an education was proving to be costly and in his case, tedious. Derek couldn’t help but think that this was the price for switching majors so many times. In his rational mind, he couldn’t very well choose a major without sampling a few others first, right?
Derek tossed the letters on top of the stack that lined the bottom of his nightstand drawer and fell onto his bed with a sigh. He watched the ceiling fan that hung directly over his bed, the blades following each other in a spinning dance. Couldn’t help but let out a sigh. Derek closed his eyes and tried to figure out some sort of grand, obvious solution that he had to be overlooking. How the hell was he going to get out of this situation? Derek had already been fired from his last three jobs for being late or sleeping in the supply closet during his shifts. Trying to juggle school and work had proved to be a lot more difficult that he had original anticipated. With a full course load he could barely find time to study and sleep at a decent time, let alone show up to work on time ready to stock books or brew coffee or remember to change the lining in birdcages.
He lifted his arms behind his head stretching his abdomen, sucking in a yawn. Derek could barely remember if he showered that morning, he wasn’t going to figure out anything tonight. The lack of sleep was starting to run his days together. He looked over to his bulletin board to check the date.
Thursday. Thank God.
Derek had Fridays off. He hated getting up on a Friday morning to rush off to class. Hopefully he could find something to do this weekend to get his mind of everything. Maybe there was a frat party or something. He shoved his hand into this pocket to pull out his phone to scroll through his contacts to find one of his available buddies that might know anything about lively events on campus. Usually he’d just ask Isaac but tonight, he was nowhere to be found. Derek couldn’t be surprised. It was typical Isaac.
11:03PM
He let out another deep sigh before standing up to tug off his jeans. Derek must have forgotten to take his keys and wallet out of the pockets because they flopped onto the floor with a thud. He bent over to pick up all the loose change and cards that’d fallen from his wallet. They were mostly cards he’d gotten from girls at bars with their phone numbers written on them. Numbers he refused to call because he wasn’t interested or didn’t have the time. Rebecca. Lacey. Catherine. Monica. He was quite fond of Monica, she had charisma. That’s when he saw it. The card he’d gotten a few nights back at a bar in town. Derek picked up the light cardstock with raised letters and flattened numbers.
Candid Models.
The name jogged his memory of who he’d gotten it from. Maybe this was the answer he was looking for.
+++
Derek and a few friends had been out drinking most of the night, a celebration for them all passing a huge anthropology test. Their bright idea was bar hopping. It wasn’t really Derek’s style but somehow he let Isaac talk him into it. At the start of the night it seemed like a great idea but by the forth bar, they were beginning to drop off one by one until it was just down to Derek and Isaac.
It had to be around two in the morning when the two of them finally reached their usual haunt, the Lycan Lounge. Isaac was hitting on some girl at the bar while Derek slammed back a few shots. Isaac whispered something to him about going somewhere and that he’d be right back. He must have said bathroom because next thing Derek knew the two of them were disappearing down the dimly lit hallway. Derek felt a smirk tugging at the end of his lips. Isaac was a real crass son of a bitch but they were the best of friends. They’d met sometime during freshman year and hit it off right away. Something about his cocky nature appealed to Derek’s sensibility.
Pressing the glass against his lips he gulped down the last of his beer, motioning the bartender over for more shots. Derek was already feeling loose as it was but he was determined not to leave until he had the worst hangover on the planet the next day. It didn’t matter how much he drank anyway, everything was on Isaac’s infinite tab. His parents were loaded so a tab like his was just a tiny drop in the bucket. Derek would never admit it but he was a little jealous of how easy he had it. Not having to worry about your savings running low and wondering what you were going to eat or figuring out which bills are due sooner to work out a payment system. Compared to him Isaac had an easy life.
Derek threw back a shot of tequila feeling the burn in the back of his throat as it slid its way down. He pinched the bridge of his nose, taking in a deep breath.
“You look like you’ve got a lot on your mind.”
Derek turned his head to see a man sitting to his right. He had to assume that he said it because it came from his direction but he couldn’t be sure. Derek was drunk after all. The man took a sip from his glass of wine and lit a cigarette.
Weird choice of drink for a bar.
“Yeah. Always do really.” Derek tossed back another shot, slamming the glass onto the counter. “Why do you care?”
He made a noise that was somewhere between a scoff and a snort. Derek remembers it being something annoying because he definitely remembers his nose wrinkling at that sound.
“A good looking guy like you shouldn’t have any problems to worry about.”
Derek turned to look at the man sitting on the stool next to him. He was wearing a grey suit, with a power blue shirt and no tie, a patch of black hair poking out from the V of his neckline. He wore a pair of black dress shoes with solid black socks. He remembers that they were really shiny, the kind of shiny that comes from constant polishing. Sure he most likely never did the polishing himself, but it gave off the message that that person really takes pride in the way that they looked. Derek on the other hand was just wearing the same pair of jeans that he always wore whenever he went out, a ratty old band t-shirt that used to belong to his dad that he’d no doubt worn early that week and his favorite leather jacket he’d gotten from his sister on his eighteenth birthday, accompanied with his trademark boots. He always wore a pair of boots no matter what the weather.
“Well,” Derek started before chugging down the rest of his beer. “School for one. I attend the university so between class and work, which I currently don’t have. Everything seems to be kicking my ass.” He waved over the bartender for another refill. Derek knew he shouldn’t have ordered another with his vision starting to blur and god knows what kind of psycho the stranger next to him was, but it didn’t matter. He was celebrating.
Whoever the man was he must’ve had money because he paid off Derek entire tab before he’d even finished choking down whatever swill the bartender put in his glass.
“You didn’t have to do that.”
“Nonsense. You’re a college student. You should be saving your money for things that matter.” He reached into his pocket and pulled out a small rectangle. Even in Derek’s inebriated state he had to surmise it to be a business card. He placed on the bar and slid it over. “Give me a call sometime and maybe I can see about helping you with your money problems.” He tossed back the little bit of wine in his glass and headed for the door with a wink.
Thank was weird. But he did just pay my tab, so I’m not complaining.
Before Derek was alone with his thoughts for too long Isaac stumbled up next to him, breathing heavy into his ear. He reeked of beer, sweat, and cigarette smoke. Isaac didn’t smoke so it to have been from the girl he’d drunkenly hooked up with in the bathroom. How he never got caught in there situations he’d never know.
“You ready to go?” Isaac wrapped a hand around his glass and finished off what was left of his beer. “Thanks buddy.”
“Well I guess I am now.” Derek didn’t mind, he was getting tired anyway and the smell of the bar was starting to come into focus.
Isaac gave his shoulder a squeeze and headed for the door. Derek pulled out a fifty from Isaac’s wallet and tipped the bartender. Isaac never trusted himself with his wallet when he was drinking so he always had Derek hold onto it. Which was fine him seeing as he was always the responsible or soberest party to actually pay the tab.
Derek picked up the card and glanced over it before remembering that Isaac was somewhere by himself. He shoved card it into his pocket and wobbled steadily to the door. No matter how drunk he was, he knew that Isaac was way worse and god knows what kind of trouble he was getting himself into outside.
+++
Derek hadn’t really thought much about it until just now. He’d been busy so it was the furthest thing from his mind. His thumb grazed over the raised letters: Duncan Hops. It was an odd name but who was he to judge, he didn’t have a choice in the decision process. He reached from his phone on the other side of the mattress and typed in the numbers.
The phone rang a few times before he got a response. Derek wasn’t expecting anyone to pick up, he was just going to leave a message and wait for this Duncan guy to call him back tomorrow. Somehow he got an actual person. The voice on the other end was quite alarming. It must have been his secretary. Her voice was high, really high. It could probably peel paint off of walls.
“Duncan Hops office. How may I help you?”
“Uh,” His mind went blank. What was he supposed to say? Maybe asking for the guy was the best way to start. “Yeah, may I speak to Mr. Hops.”
“May I ask who’s calling?”
“Yeah, he doesn’t really know who I am.” His tongue flicked over his lips looking for moisture. His throat was starting to go dry. “He gave me his card last week and told me to give him a call.”
“Oh, yes. He told me to keep an ear to the ground for your call. Name?”
“Derek.” He said flatly.
“Hold please.”
Next thing he knew there was cheesy piano music playing a rendition of some old rock song from the seventies. He hated being on hold but found himself humming along just when Duncan answered the phone.
“Hi, Derek?”
“Yes, hello?”
Duncan sighed into the receiver. “I have to say Derek, you kept me waiting quite a while. I was expecting you to call me sooner than this.”
“Well you know how it is sometimes. I didn’t want to come off as too eager.”
He could hear Duncan laughing on the other end of the phone. Derek was unsure if he should join in or if he was in on some joke he wasn’t aware of.
“Well you don’t want to seem disinterested either.” He said with a chuckle. “So Derek, what does your schedule look like tomorrow around noon?”
Derek paused for a moment. He was thinking about blowing it off for a few days. Make Duncan chase him for a while. That was the plan, until he caught a look at the bills in his drawer from the corner of his eye.
“Completely free.”
“Good to hear.”
The rest of their conversation consisted of Derek taking done an address and trying to ease the awkward tension with a bad joke or two. Duncan was nice enough to indulge his horrible sense of humor before finally getting off the phone to take another call. He looked at the address on the post-it by his bed. He’d never heard of the place they were going to be meeting but that was the least of his worries. What was he going to wear? When he met Duncan he was wearing a suit, so maybe he needed to dress professional. Then again when he gave Derek his card he was casual, open shirt-no tie.
Split the difference.
Lucky for him Isaac was out on a date or so he said. It was the perfect time to sneak in and raid his closet to steal something to wear. Everything Derek owned was dirty. He hadn’t gotten the opportunity to do laundry in the past couple of weeks. Any free time he got, Isaac always found an excuse to drag him off somewhere.
Nonetheless Derek liked living with Isaac. He was the ideal roommate: quite, because he was hardly ever there; always stocked the fridge, because he knew that Derek would cook something; and he never asked for rent money. Their relationship was on a barter system or at least that’s how Derek liked to think of it. He would help Isaac with school work and keep him out of trouble while drunk and Isaac would pay the rent. It was a win, win situation.
+++
Derek probably circled the block a good five times before going inside the restaurant. Walking around wasn’t so bad, he hadn’t made it to the gym in over a week and it was good cardio. He hated being too early, came off as too eager. Not ideal when going for an interview. Somehow he still managed to show up thirty minutes before he was supposed to meet Duncan.
When he walked in Derek went directly to the bar. He was still early so it seemed like the logical thing to do. He could spot him as soon as he walked in and also get a drink to calm his nerves. The restaurant was nice and it didn’t seem too busy for the time of day, it must’ve been one of those hidden treasures of the city that Derek always heard his classmates talking about.
The waiter wasted no time in bringing back some fruity concoction Derek picked out of the daily specials menu. It smelled fantastic and looked even better. Derek already hoovered down half of the drink when he saw Duncan walk in. He wore a fit black suit with a magenta shirt underneath and black shades to accessorize. Derek watched him walk over to the bar, taking off his sunglasses to reveal his vibrant green eyes. They were breath taking. He must not have noticed when he first met but then again the guy could’ve had an extra hand and he wouldn’t have noticed. He was pretty hammer that night.
“Derek, nice to see you again.” He said shaking his hand.
Duncan led him over towards a table a few feet away from the bar towards that back. He must have called ahead and reserved a table. Which made sense to Derek; he came off like the type that would make reservations.
Derek took nervous sips of his mojito, trying to ease little nerves he had left. It wasn’t long until he reached the bottom and made that horrible slurping sound straws make.
“Refill?” Before Derek could tell him no, the busboy was bringing over another and whisking the empty glass away to be cleaned. He was impressed at the power Duncan seemed to have over the staff. Something about it was sort of terrifying.
Derek didn’t say much, he just gave one syllable responses whenever Duncan would ask anything. He was sure that at some point the guy was going to wonder if he had a disability of some sort.
Get a hold of yourself. This is just a job interview. He closed his eyes breathing in deep. Exhale.
“So what exactly is this position that I’m interviewing for?” Derek blurted out. He couldn’t hold it in anymore; maybe he was a little too loose now.
“You get right to the point don’t you?” He laughed. “Well you would be working directly under me, for now on a trial basis, as a, let’s say courtesan. To be paid for your services accordingly.”
Derek was silent. He sucked on the straw to retrieve what little liquid was left at the base of the glass. Something about the word rang in his memory; so familiar but foreign at the same time.
“Courtesan…” He pursed his lips at the word as he thought. Suddenly it all clicked “You mean a prostitute?!” Derek clapped his hand over his mouth, trying to force the words back in but it was too late.
“Shhhh! The whole restaurant doesn’t need to hear you. And we prefer the term escort. Prostitute is so passé.”
“Look I don’t know where you got the idea that I might be interested in your line of work but I don’t think I’m really cut out for that sort of thing.”
“Why not?” He pulled a silver case from the inner lining of his pocket, popping it open to retrieve a cigarette. The filter was gold and the paper a light pastel pink. Duncan rubbed the gold over his lips before lighting and taking a long drag.
“I think you’re an attractive young man with a nice build and gorgeous eyes. I actually have a list of clients prepared for you if you agree to come on.”
Derek watched his lips as smoke escaped after every word. Did he really want to do something like this? Sure one could say he was good at sex, he’d certainly never had any complaints from previous partners but was this something he really want to get mixed up in.
“I don’t know.”
“Look. Before you write me off and say no, you should know that our clients pay very well for your services and sometimes don’t even ask for anything sexual. As escorts you work a level above the common whore. You have the luxury of setting your own hours and doing only what you feel comfortable doing. I can tell you that can’t beat that.”
Duncan reclined into the chair taking another drag on his cigarette. He looked at his watch and stamped out the half smoked butt into what was left of the key lime pie he was eating.
“I’m sorry I have to cut this short. I have another appointment in twenty minutes. I usually never double book but I’m running short handed since one of my employees got married and quit. Good for him, bad for me.” Duncan stood up and straightened out his jacket. He pulled out another business card and scribbled something on in before placing it on the table.
“That’s my personal phone. Give me a call if you change your mind. Lunch is on me, order whatever you want and they’ll charge it to my tab.” He winked and put on his sunglasses before walking towards the exit with a wave.
“A real charmer that one.” Derek had to admit that he had a confidence about him that he kind of admired.
When he got home Isaac was there, his body thrown over the couch as usual. He’d most likely just gotten in a good twenty minutes before Derek had walked in the door. Derek made his way over to the fridge and put the leftovers away. He made sure to slam the fridge door, rousing his slumbering roommate.
“Did you just get home?” He heard a muffled reply that sounded like an affirmation of his suspicions. Isaac lifted his head for a moment, black shades covering his eyes. Derek assumed it was to ease the light intake on his throbbing handover.
“By the way, Stacy or Gwen or whatever is having a party later tonight and said we should come.”
“Oh. No no no. You know you can’t go to her party. You slept with her sorority sisters last week. Like three of them.”
“Yeah I don’t remember that.” He said before he dropped his head back into the cushion. “Besides if she can forgive me why not go and drink her booze.”
Arguing with Isaac was pointless especially if he was nursing a hangover. Derek made a point to stomp his was to his room before slamming his door. He could hear Isaac shouting something along the lines of ‘you’re a dick’ back at him through the door.
He could see that Isaac had taken the initiative to check the mail and the liberty of putting his one his bed. How sweet of him, my own delivery service. One was a letter from his sister Laura telling him about her moving into Manhattan after getting a raise. She’d even sent him a check for his half of the rent for this month. He never had the heart to tell her that he never paid rent and all of her money goes to him drowning his money woes in cheap vodka.
There was also a letter from his Uncle Peter which he didn’t bother opening. It was always something he didn’t want to hear about, him traveling to India and finding religion or going to Africa and being told he couldn’t bring back any diamonds. You’d think with family like Laura and Peter he’d be able to pay his bills on time but he didn’t want to burden them with his problems. The first two years of college he received a partial scholarship so working to pay the other half was nothing. Now he was in year four of college, he’d lost his scholarship to his slippage in grades and lost jobs due to poor time management skills.
No surprise to him, at the bottom of the stack was another statement saying that this semester’s payment was past due. Derek plopped into his mattress, limbs dangling over the sides. His body numb. It was that kind of feeling one would get right before they’d go into a panic about what you were going to do. Derek pulled the card from his pocket and stared at Duncan’s number.
What have you got to lose?
+++
Duncan told him that he would be meeting his “date” at one of the fanciest hotel in town. Derek couldn’t help but feel out of place in the lobby of a place that nice.
Even the bellhops have suits on.
Duncan had paid for the suit that he was wearing. He called it a ‘gift’ for him signing on. With the way he phrased it, Derek was starting to think there were strings attached somewhere. All he had to do was pull.
Derek went to bar, as he usually did in an uncomfortable situation, and ordered a drink. Again he needed to ease his nerves.
It’s okay to have a few drinks. It’s not every day you start a new exciting career as a prostitute. No, that’s not right. Escort.
He wouldn’t be hard to find for whomever he was supposed to be meeting. Duncan told his client what he would be wearing, an all-black suit a silk red shirt for accent. Derek wasn’t feeling all too comfy in his new attire. Sure it was nice and fit well in all the right places and was free, just something about it felt weird. Duncan said something to him on the phone about him being the new red boy. He had to assume that they all had their particular colors and code names. It made sense. You couldn’t very well just be handing out your real name and number to strangers all the time.
It’s actually pretty ingenious if you think about it.
He stroked a hand over the lapel of his suit. Derek’s color was red, which he didn’t mind. He looked good in red. It was his code name that bothered him. Philip. He never really liked the name and now he was stuck with it. Duncan was pretty set on him being Philip.
Maybe I can just shorten it to Phil if anyone asks.
Derek was flying blind. He had no clue what his client was supposed to look like. When asked, numerous times, Duncan simply replied that ‘it’s an adventure, roll the dice.’ Derek was hoping for a woman. Preferably tall and brunette, like the one that was taking a seat at the end of the bar. She was elegant with perfect curls falling over her shoulders, which accented her silhouette figure in the all black night gown that hugged in all the right places.
His eyes glanced up from his glass over to her. She smiled back at him from under her hair before getting up and walking in his direction. Derek straightened his posture, waiting to greet her, when she walked past him to a blonde standing behind him.
Why would it be her? That would be too perfect.
While he was lost in thought, a gentleman wearing a baseball cap took a seat next to him. He had shaggy brown hair that stuck out from under his cap and stubble that looked like it needed a trim. But that wasn’t his most interesting feature. The real kicker was that he wore cowboy boots with his slacks and blazer.
Everyone has their own personal style I guess. He kind of looks like a cowboy if you think about it.
“So you must be Phil.” He said turning towards him.
FUCK.
“Yes. I am.” Derek said extending a shaky hand. It was the polite thing to do. He didn’t really know what to do in these kinds of situations. He’d never been in a situation like this one before, let alone with another guy.
“Should we take this conversation up to my suite?” He gestured a thumb over his shoulder to the elevators.
Derek could feel a lump starting to form in his throat. He and the Cowboy left the bar and entered the elevator. His companion pressed the number 7. At this point Derek was on the verge of full on panic watching the number light up. A million thought raced through his head as the small room began moving.
Not only am I about to have sex for money, I’m about to have my first man-on-man experience. I don’t even really know how these things work. Do I take the lead? Does he? Oh god I don’t know if I can be on the receiving end.
It was all starting to become too much. There were so many thoughts rushing around at once, the biggest becoming how great the elevator smelled.
I mean really, how do you get an elevator to smell just like lilac?
The elevator stopped abruptly, the door sliding open to reveal the beautiful carpet of the hallway. Cowboy stepped out first, while Derek stood in place.
“You coming?” He asked tipping his hat.
“Yeah. I uh…just lost in thought.”
Derek followed him down the hallway until they stopped in front of a plain white door. 705. The Cowboy slid his card into the electronic lock and turned the knob. Stepping in, the first thing that crossed Derek’s mind was how big the room was.
“Are all the rooms this big or are you just trying to impress me by kicking out some extra cash?” Derek often liked to defuse tension with a joke. And at the moment he was feeling pretty tense.
“This is usually my room whenever I come to town on business. If I’m going to be away from home I’d at least like to be comfortable.”
He didn’t hear it at down in the bar but the Cowboy had a little bit of an accent. You could only hear it in certain words. It was the way he said ‘comfortable’. Derek couldn’t help but think that it was kind of cute. Not in an attractive way but in the way puppies were cute.
Oh god how am I ever going to get through this.
The Cowboy took a seat on the bed and stared at Derek standing motionless by the wall near the door. He patted a hand on the spot next to him calling him over. Derek couldn’t very well refuse him; he’d rented his services for the evening. Not just a few hours, the entire evening. The Cowboy had Derek until midnight and according to Derek’s watch that was still five hours away.
Maybe he’ll just want to talk or something. Please dear god, let him be the talkative type.
That’s when he started unbuttoning his blazer and toss over the arm of a nearby chair. Derek’s eyes grew wide, a tiny bead of sweat cascading from his forehead to his brow. The Cowboy must’ve seen the look on his face.
“Ha ha. Calm down. I’m just talking my jacket off.” He got up and sauntered over the mini fridge. Derek hadn’t even noticed it was there. He was in too much shock to really notice the décor.
The Cowboy returned with two glasses and a vintage bottle wine.
“You have to give it just the right amount of time to breathe.” He said swirling the dark liquid around in its container. “Are you a wine drinker?”
“Uh, no. More of a beer and whiskey man myself.” An overly friendly laugh filled their silence.
Calm down. You’re making an ass of yourself.
The Cowboy smiled and handed him a glass. “Cheers to us.” He said.
Their glasses clanged together with a chime. Derek took an apprehensive sip from his glass. He was in a hotel room with a stranger, who knows what kind of funny business he might pull.
If he was going to do anything he probably would have done it by now. The hard part was getting me up here.
Derek quietly sipped his glass of wine. He could tell that their elongated silence was beginning to make his client uncomfortable. The Cowboy was starting walk around and inspect random furnishings. Maybe the biggest obstacle of doing his new line of work was for him not to be Derek but become to Philip the escort.
“Well, here goes nothing.” Derek knocking back what was left in his glass.
After three more glasses of wine Derek had gotten to know a bit about Cowboy. He learned that his name was Jackson and that he worked in textiles. He learned that Jackson was often in town for business and requested the services of escorts often. After a while he’d forgotten that Jackson was even paying him, he was just enjoying his company. He was so comfortable with Jackson that he openly admitted that he’d never been with another guy before.
“Really? Not even once?”
Derek shook his head.
“Wow. So I’m going to be your first?”
“I guess you can say you’re my maiden voyage.” Derek laughed.
“So, you’ve never even kissed a guy before.”
“No.” He paused, “Well, that’s not true actually. There was one boy.” He took a sip from his glass. Derek could feel a smile pulling at the corners of his lips just thinking about him. “He was actually one of my best friends growing up. He was this goofy, hyper-active eccentric kid. I don’t know what it was about him, he just kind of complimented my I guess. He-”
Derek waved a hand as if the swat away the memories. “I don’t want to talk about him. He’s just a ghost of my childhood.” He didn’t want to dredge up anymore of his past than he needed to. Derek knocked back the rest of his wine and placed the glass on the nightstand. His head was lucid and clouded with thoughts that made his brow tighten.
Jackson slowly walked over to the bed, stopping right in front of Derek. He placed his hands on either side his body and crept closer to his face.
“Let’s take this slow. Okay?”
Derek watched his lips as he moved in closer, the distance between them narrowing. Jackson licked his tongue over Derek’s lips before pulling away. Their eyes watched each other’s every movement. Jackson placed a kiss on his lips, pulling back once more. His method of easing into kisses was proving too slow for Derek. He grabbed the back of his head, devouring his mouth.
Derek leaned back and allowing Jackson’s body to topple onto his. He could feel Jackson’s muscles tense and flex against his, skin contracting trying to match body motions. They moved almost in unison, almost as if they knew exactly what the other wanted.
Jackson traced the lining of Derek’s jaw with his teeth. He sucked his earlobe into his mouth biting down gently before tonguing invisible lines over his neck leaving suckling kisses on his way down to his collar.
“I’m going to be your guru. Just follow my lead.”
He kissed him deep, undoing the buttons of his shirt in the process. Derek worked his shirt off with ease, running his hand over Jackson’s back, gripping his shirt to pull him closer. His palms slowly moved down to grab perfect curvature of his ass. Derek could feel Jackson grind his hips into his in approval.
“Rip off my clothes.” Jackson whispered.
Derek wasted no time adhering to the request. His fingers tucked into the spaces between buttons and pulled full force, exposing his perfectly chiseled body. Derek pulled his nails over the multitude of abs muscles that didn’t seem to end. Taking the extra initiative, he licked from Jackson’s treasure trail to his neck, biting an indention every so often so he’d remember he was there.
He felt Jackson shudder against him as he sucked in a gasp and let out a FUCK through gritted teeth. Derek was starting to realize that Jackson was another him. Whatever Derek liked during sex he should turn up to eleven for this cowboy.
Jackson started fumbling with the buckle of his pants, trying to free his throbbing cock from its prison. By the time he’d worked them off Derek was already in his underwear. Jackson kicked off the white brief that was wearing until he was naked in his cowboy boots.
Derek couldn’t help but think of it as a turn on. He never knew that he had a thing for cowboys. Jackson lowered himself to hover over Derek’s almost naked form, his cock smearing precome all over his thigh as he rocked into him. Jackson puffed his warm breath over Derek’s skin, watching him writhe as he traveled from his pectorals down to the girth twitching in the red briefs he was wearing (another idea of Duncan’s).
Jackson slipped his index fingers into the waistband as his lips traced the shape of his cock trapped behind cotton. He nuzzled his nose over the head of Derek’s cock, a sticky puddle beginning to form in the middle. Jackson took a deep breath, inhaling his scent.
“You smell amazing.” He mewed with baited breath.
Derek let out a near silent whimper. Jackson smiled, licking from balls to tip, pulling the red prison past his thighs. His fingers pulled down on cock releasing it with a slap against Derek’s stomach. Jackson fisted his girth with a tight squeeze, taking in the size, as if it were an appraisal. He wasted no time swallowing Derek down to the base.
Derek clenched his eyes tightly, arching his back in a moan of desire. “OH MY—“
He’d never felt anything like it before, Jackson’s mouth like a vacuum around his cock, his head bobbing up and down as he slurped back and forth, looking up at Derek every so often to see how well he was doing. Jackson wrapped a hand around himself, jerking feverishly to match the motions of his mouth. With his free hand, he pressed against Derek’s virgin entrance, making his dick twitch.
He popped Derek out of his mouth with a loud slurp, jerking at the base while licking at his balls. Derek could barely catch his breath. He’d never experienced anything of this magnitude before. His skin was on fire, ever touch felt like a surge that led straight to his cock, bringing him closer to climax.
Derek pulled Jackson up to his mouth, gorging himself on the taste on his own cock. He flipped him, hovering over Jackson’s smaller frame. Derek pulled his legs up exposing his hungry hole.
Jackson, without missing a beat, reached in and pulled out a condom and small bottle of lube from the inside of his boot.
“That’s where you keep your condoms?” Derek asked with a laugh.
“They can be very handy.” His replied.
Derek tore open the wrapper with his teeth. He rolled the latex over his cock, applying a generous amount of lubricant to himself and Jackson before pressing the head of this dick into him. Jackson sucked in a deep breath as Derek slid inside slowly. Their foreheads pressed against one another, Derek could hear his tiny moans with every thrust, each one giving him approval to go faster and harder.
Derek rocked his hips in a steady motion, feeling Jackson writhe underneath him. He buried himself into the crook of his neck, taking in the sweet smell of sweet and whatever cologne he was wearing as he thrust himself to the hilt.
“Ha-harder.”
Derek rammed his hips with ferocity into his hole as if he were trying to break him in half. Jackson didn’t care. He dug claw marks into Derek’s back with every motion, bucking himself to meet every thrust, begging for more.
Jackson wrapped his legs around Derek’s torso, giving him leverage to push himself even deeper. Jackson cried out in ecstasy.
“DON’T. STOP.”
Derek could feel to copious amount of precome leaking from Jackson’s cock onto abdomen. The feeling of knowing how much he was getting off made him harder. The extra blood surging to his cock made Jackson scream loader. Derek clenched a fist into Jackson’s hair, pulling back to exposed his neck. He ran his longue over his adam’s apple, biting tiny crescents into his skin.
Jackson flipped the two of them over, hover over Derek’s cock before taking to inside. He tweaked one of Derek’s nipples, as he wrapped his hand around his own cock jerking to match his movements. Derek could feel himself getting close, he never imagined watching a guy impale himself on his dick would get him off so much.
Jackson came first, hard and without warning. His come soaking Derek’s chest all the way up to his neck, the hot ropes searing his skin as his bucked up into the man’s hole for his own release. He slammed in harder and harder, Jackson still moaning and riding out the remnants of his own climax. He hopped off, snatching the condom in one motion and suck Derek’s dick into his mouth.
Derek let out a string of curse words as Jackson’s tongue swirled around the base of his dick.
“Oh holy shit, I’m so close, don’t stop.”
Derek bucked his hips up, grabbing the back of Jackson head in fistfuls. He slammed Jackson’s head into his lap as he came down his throat. Jackson swallowed his load, suckling at the head of his cock, making his body shudder with aftershock.
Jackson rest his head on Derek’s come soaked stomach, drawing little circles in the residue, Derek hands playing loosely with his hair as their breathing slowly got back to normal.
“You know that you’re not usually supposed to do that. Come in a client’s mouth, I mean. But because it’s your first time, I’ll let it slide.”
“Oh. Sorry.” Derek could feel himself blush. He was hoping it was just on his face.
“It’s okay.” Jackson ran a hand over the head of Derek’s cock, making him jump. “You think you can go again?”
+++
Before he knew it, it was midnight and they’d fucked twice. Three times if you count Jackson teaching him how to give a rimjob. After a shower and another glass of wine the two men part, Jackson promising to only ask for his service whenever he’s in town.
When Derek home Isaac is passed out on the couch.
How does he do this every night?
After a few minutes of staring and drawing a penis on the side of Isaac’s face, he abandons the thought and maneuvers his way over empty beer bottles to him room. Derek collapses onto his bed, exhausted, his eyes heavy from a hard day’s work and some of the best sex he’s ever had. Taking off his jacket, he found the envelope Jackson had given him at the beginning of the night. They were having such a good time Derek almost forgot that he’d gotten paid for it. Looking at the amount he couldn’t believe his eyes. If this was what his new job was going to be like, he wasn’t going to have a problem at all paying tuition.
Hell I might even quit school all together.