Chapter Text
Cas glanced down at his watch as he rode the elevator up to the top floor always dressed casually in his jeans and a loose t-shirt with his mandatory black bag in one hand.
Always punctual.
The elevator dinged before opening and leading him into a long hallway. The room he was looking for was at the end.
The man he was here for was not exactly a regular but he calls often enough that he may just become one.
From what Cas knows of the man, the guys got quite an extensive customer list. He was already really popular with the ladies. His male clientele has been slowly growing from what they've discussed during these last couple of sessions.
Castiel stopped at the door, raising his hand to knock.
It didn't take long for the door to swing open, revealing a handsome man with nothing on but gray sweats, his lightly tanned skinned torso with freckles everywhere, sandy brown hair and the greenest eyes Castiel has ever seen.
"Hello, Dean,"
"Hey Cas, right on time," Dean quipped, holding a hand out, gesturing for Castiel to come in.
After shutting the door, Castiel took in the familiar settings of the apartment. A kitchen set right next to the doorway, the spacious living room before him with a dining room off to the left. The hallway next to the kitchen leading down to the bedroom and bathroom.
"Who is the client today," Castiel questioned as he turned to look towards Dean who was cleaning up the kitchen.
Humming to himself, Dean placed the rag he was using into the sink as he came around the counter to join Cas in the living room.
"He's new, some big corporate bigwig needing some stress relief," Castiel nodded along in understanding. Those secretly gay types. Probably has that apple pie life with a wife, 2.5 kids, white picket fence and dog to boot.
"I see why you'd need me then," already picturing how rough this guy will be. "The couch, as usual?"
Before Castiel made his way to the familiar chocolate loveseat, he heard a low cough, stopping him in his tracks.
"Actually, I was wondering if we could do this in the bedroom?"
Raising a brow at the question, Castiel nodded his head as he was lead down the hall. When Dean first started using their services, Castiel had remembered the man asking if they could use the bedroom.
The more comfortable he got, the less he cared about where he was being prepped.
The room was simple, a queen size bed with a comfortable-looking blue comforter. A lot of fluffy pillows at one end. One nightstand, a dresser, a closest off to the right with an attached bathroom next to it. Pretty plain based on the rooms Castiel has seen since working for the company.
“Have you eaten anything today?” Castiel questioned, starting their usual routine of questions. He turned in time to see Dean pushing down his sweats so they’d pool at his ankles. For a man of his size and structure, he was very well hung. No wonder his female clientele list was long.
“Just water. I ate last night though,”
“Bowel movements?”
“Yes, about an hour ago. I’m all clean, took a shower and everything,” Nodding his head, Castiel walked over to the bed to place his black bag on it.
“Well let’s get started. When are you meeting this guy?” Castiel asked as he watched Dean crawl onto the bed. He moved back on his hands and knees so his knees were inches away from the edge, before dropping to his forearms to present his ass towards Castiel.
“And what a pleasantly plump ass it was.” Castiel thought as he opened his bag that was next to Dean to pull out the lube and black latex gloves.
“In an hour or so, or whenever his business meeting ends. Everyone is supposed to be leaving for lunch today,”
“So you’re having an office fuck. You haven’t had one of those before,” Castiel commented as he pulled the gloves on and moving to place himself directly behind Dean “How are you feeling?” while placing a hand on man’s ass, the other grabbing the lube.
“I’m feeling awesome,” He watched Dean look over his shoulder to wink at him. Castiel rolled his eyes at the comment. “Fine,” in an exaggerated voice. “Everything is good, but I’d feel comfortable going slow today.”
Nodding his head in understanding, Castiel popped the lube cap open and pouring some onto his gloved finger. He rubbed it between his thumb and two fingers to warm it up before placing it at the entrance of the awaiting hole before him.
Slowly he pushed his middle finger in without any resistance. He started slow, in and out, hearing the slight hiss from Dean every now and then. It didn't take long for Castiel to add the second digit.
He pushed the two fingers in, all the way to his knuckles, keeping them there to allow Dean to adjust.
A low moan from the man below signaled that he was getting used to it.
Keeping his two fingers still deep in Dean, his other hand reached into his bag, digging around until his hand felt the cool touch of steel of the item he was looking for.
"How big is this guy?" Castiel questioned, wiggling his fingers around before starting to pull his fingers in and out.
Dean grunted out, letting his head falling between his arms.
"From what I was told," he panted out, "He's bigger than me," Castiel nodded at the information, deciding that Dean was good by pulling his fingers out.
Dean shuddered, his ass leaning back at the loss of contact. Castiel couldn’t help but stare at it. Perfectly round, plump, definitely chiseled from the finest piece of rock known to man. What Castiel wouldn’t give to see it gleaming red from being spanked by his hand.
“Breath,” Castiel thought to himself. Remembering the rules set by his company.
They came to assist in stretching the Male Clients before their Scene or their “Dates”. Giving in to the moment like this could garner a bad reputation for them. Even though this is the only company that does this, positive feedback is what keeps them in business.
“So much for going slow,” Dean commented, glancing over his shoulder and seeing the plug in Castiel’s hand.
“You adjusted quickly. Besides, we’re already ten minutes in,” Castiel replied, uncapping the lube again, squirting a generous amount onto the metal plug. “And you always have trouble with this part,” he rubbed his gloved hand over it, trying to warm it the best he could.
“What can I say? You have gentle hands,” Castiel looked down at the man, the tip of the plug already placed at the puckering hole, slowly pushing it in. "Except for that" Dean ground out, head falling back between his arms.
And this was the smallest one Castiel had.
Watching the small silver plug inch it's way deeper into the man, Castiel had to look away.
"S-slow," Dean uttered out under his breath.
And Castiel did. Slowly pulling the plug out and pushing it back in. Dean’s head lifted, followed by the rest of his torso so that he was on all fours.
In doing so gave Castiel a clear view of the hard, weeping cock Dean was sporting.
“You’re good,” Dean commented after taking a deep breath.
Castiel gripped the plug again, pulling it completely out. He stared at the puckering hole once again as he placed the used item on the towel he just produced from his bag.
With his clean hand, the one without lube on it, he opened his bag by the handle to look at his options.
“Is he bigger by length or girth?” Castiel questioned, staring at what he had.
“I don’t know,” Dean glanced over his shoulder at Castiel. “Girth probably.”
Choosing the next item, he lathered it extensively. This is as big as anyone could get so it should be good.
“Move up,” Castiel ordered, watching Dean move farther up on the bed. Shifting out of his shoes, Castiel moved onto the bed as well, one knee between Dean’s legs and the other on the outside. Placing one hand on Dean’s lower back, he placed the instrument at the entrance.
“Take a deep breath and relax,” Castiel warned as he added pressure to get the item past the ring of muscle. He heard Dean grunt at the intrusion, panting a little as he fought to control his breathing.
“Dean,” How long has it been since their last session? Probably two weeks ago? Shaking his head, he pulled the item back and then pushing it in a little more. He was met with little resistance after each thrust. He was getting used to it. Good.
Castiel had just managed to get the toy up the hilt when he heard a strangled noise. He paused.
“Stop,” Dean forced out, dropping to his elbows, forehead resting on the bed.
Castiel looked down, hand seizing its movement of pulling out. He let go of the flat hilt part, his eyes glancing down towards the man's feet. His toes are curled tight, looking around, the hands were clenched as well.
That's when he noticed the problem. There was an obvious stain from all the precum dripping from the man's weeping cock, straining hard from lack of contact.
Stuff like this does happen. The easiest way is to either help them relax or stop until the problem relieves itself.
"J-just give me a moment," Dean said, a little breathless, one of his hands coming up to cover his face.
“Would you like my assistance?” Castiel asked, a little taken aback at the situation. He’s been assisting Dean for the past year and a half and never has this happened with him before. Generally, it’s been casual, simple and downright friendly.
Dean always keeping the situation light between them with jokes and entertaining stories. But this was different.
“Dean,” Castiel asked again.
“P-please,” the man managed out, completely out of character for Dean.
Castiel starred. He’s done this before. Both professionally and to the other men, he’s been with personally. But this was Dean.
Taking a moment to compose himself at the new scenario, he slipped
back into 'professional' mode as he moved closer.
Reaching down for the lube, he uncapped it and squirt a generous amount into his hand. Tossing the bottle back into his bag, he took the mans’ length in his left hand, swiping his thumb over the slit to smear the precum there and moved his hand around the length to smear the lube.
Hearing Dean whimper at the contact right as Castiel started his slow strokes along his length, allowed him to use his right to slowly pull the toy out again.
Having someone ejaculate during these sessions is not uncommon. Like Castiel thought earlier, he’s had to do it professionally before. It’s one thing to see Dean’s dick, but to have it in his hand now. Castiel had to work on his breathing, trying not to get caught up in the moment. He kept his focus on the matter at hand, eventually getting the toy in sync with the stroking of Dean’s length.
The man’s breathing became ragged, whimpering from the assault, as he got up on his hands so that he was on all fours, again, so that he could start pushing back into the toy and forward into Castiel’s hand.
It didn’t take long.
Dean bit his lip, muffling a cry as he came all over Castiel’s hand and comforter, his body shuddering through his orgasm.
Hands freezing in place as the man before him slowly dropped to his elbows, Castiel could see the man’s torso expanding and collapsing as Dean tried to regain his breathing.
It was quiet.
Neither one speaking. Of course, what could Castiel say in a situation like this...
“Y-you can...you can take it out,” Dean ground out, turning his head to peer at Castiel.
Without a word, Castiel grabbed the hilt of the toy and slowly pulled it out. Dean grunting at the feeling, groaning once it was completely out.
Placing the toy with the plug on the towel, he folded the cloth over them nicely before placing the bundle into his bag.
Removing the gloves, turning them inside out, he walked into the attached bathroom to dispose of them into the trash. When he walked out, Dean was completely stretched out flat on his bed, his head buried into his pillow.
“Make sure to drink plenty of water,” Castiel commented, walking back to his bag that was next to Dean.
A grunt was his only response.
“Do I need to stay to make sure you’re ok?” Castiel questioned, watching the man not move.
His response was Dean lifting his arm to wave at him.
Taking his cue to exit, Castiel grabbed his bag and headed for the bedroom door.
It wasn’t until he got to the front door, Castiel’s hand keeping it open so he could lock it behind him, as he was grateful that Dean hadn’t seen the bulge that Castiel was sporting from the noises and the beautiful view of the man cumming had done to him.
Never had he had a client affect him the way Dean did just then?