"Hello pet. Didn't expect to find you here." The demon laughed softly as the Winchester whirled.
"Crowley! What are you doing here?"
"Whoring yourself, darling? Come on. Don't tell me you're that desperate."
Dean's cheeks colored softly before glaring at the other. "It's none of your business."
"Actually, it is. Lips that just beg to be wrapped around a cock and a pretty little ass." Crowley surveyed the hunter's body, slapping Dean's ass. "What are your prices?"
The man glared even more, yelping in shocked horror at the slap. "Y-you can't get me!"
"Are you so lucky as to be able to choose whom you whore for?" The crossroad king laughed softly, pulling the hunter to him.
Dean only glared, not fighting Crowley's hand around his wrist.
"Ah…Pouting? Ashamed I found you here? Well, here's the deal. You don't whore for me, I tell Sam. You whore for me, I have never seen you doing anything remotely like this and Sam doesn't know. What do you say, pet?"
Dean had blanched at the mention of Sam's name and he gave in. "F-fine…Fifty for a blowjob, hundred for a fuck. Condoms must be used." He pulled the demon to his car, sliding in and watching him slide after.
"I'm allergic to latex, darling. It must be bare, but I can't carry any sort of disease, perk of being a demon."
"Then get out!"
"Right. I'll just be telling your boyfriend." Crowley moved for the handle of the door.
"Fuck! Stop! Fine! But if you get me diseased, I'm killing you."
"Alright. Now suck!" Pushing the man's head to his crotch, he groaned as Dean nuzzled him, his hands working at Crowley's belt.
It was quick work and Dean found himself staring at a thick cock that would definitely leave him aching. At another push from the demon, the blond licked hesitantly over the slit, his eyes on Crowley's.
"Mmm. Good pet."
Gaining confidence, the hunter turned prostitute sank down around the demon, barely able to fit the cock's girth down his throat.
Crowley held still, letting Dean work his throat around him. "Dean! N-need to fuck your mouth."
The inner slut in Dean let out a moan and the demon's hips jerked forward, burying himself deeper down the blond's throat as his fingers tangled in the short spikes. "G-good pet. So fucking good."
Dean whimpered but didn't fight the thrusts, letting Crowley own his mouth with each powerful shove. The demon increased his pace, forcing Dean to take everything he gave him.
The blond gagged and moaned, tears filling his eyes at the pain, but he didn't struggle, not even once.
It wasn't long before Crowley was coming hard down the man's throat, crying out in pleasure. He released Dean swiftly, letting the hunter collapse to the floor. Swallowing as much come as he could, the blond gasped, coughing as he stared up at the other's face. "A-are you still gonna fuck me?" He couldn't keep the fear from his voice.
"Yes, darling. When you're stretched, I want you to impale yourself on me." Smirking, Crowley began to strip him the unresisting hunter, who trembled at the touch of the demon's fingertips to his ass. "Relax, pet. Or I will hurt you."
Nodding softly, he forced himself to relax as Crowley eased a spit-slicked finger into him. Closing his eyes against the feeling, Dean was glad he'd stretched himself beforehand as the demon slipped in a second finger without much resistance.
"Stretched yourself well." Adding the final finger, Crowley groaned.
"Y-yes…but you're bigger than the usual guys."
"Let me guess. Overweight, middle aged businessmen, married with children?" He crooked his fingers, angling for the hunter's prostate.
He was soon rewarded with a soft cry and Dean bucking up into him. "F-fuck!" The blond moaned, trying to force Crowley's fingers into his sweet spot. "E-exactly. Please! Please do it again!" He whined in desperation, starting to lose himself in his need.
"Mmm. So I'm bigger?" The demon tilted his head, on the verge of giving in to the Winchester's plea.
"Y-yes. Fucking HUGE!" He screamed the last two words as Crowley drove his fingers hard into his spot, twisting them. "H-holy fuck! Please Crowley!"
"You want it now?"
"N-no. Need it. Please."
"Hands and knees, darling." With a grin, Crowley stripped himself completely.
Before Crowley had gotten out "darling," Dean was in position, whining his want.
Laughing, the demon lined up his slicked cock to Dean's hole, pushing the fat head in a little. "Do it, babe."
Gulping, the blond relaxed every muscle he could before shoving himself back. He was halfway on before he couldn't go farther because of the pain. "Please don't. I need t-to-"
"Breathe! I don't want you passing out on me." Crowley spoke in his usual authoritative voice but kept still, something that wasn't lost on Dean.
Taking a shaky breath, the hunter slowly adjusted to Crowley's size, shaking beneath him.
With a quick thrust, the demon was completely buried in the Winchester. Unable to hold back his whimpers, Dean tried to adjust.
"So tight. Good boy." Crowley petted at the other's side, giving him more time to relax. Once Dean was relaxed enough, he began to thrust shallowly.
It hurt the man, but he forced himself to stay quiet, each thrust of Crowley's sending pain shooting up his spine.
Crowley increased his pace, soon pounding in and out of the submissive hunter. Knowing the blond was hurting, the demon slowly cut off the pain, and soon it was only pleasure.
Resulting in a deliciously desperate Dean who pushed back hard. "P-please. Harder, Crowley!"
Doing as the other asked, the king of the crossroads growled as he started to stroke Dean, surprising the hunter.
The way he cried his name pushed the demon closer to the edge. "S-so close!"
"G-god. Wanna feel you. Feel you come! Please." Dean's babbling only aroused the other more, and he came with a wordless cry.
Moments later, the hunter came screaming the other's name as he came, coating the demon's hand and the leather seat beneath him.
They collapsed to the seat, tangled up in each other. It was silent but for their harsh breathing for many minutes. Finally, Dean spoke up. "C-Crowley?"
"Yes?" He shifted, letting his softened cock slip from the man's ass.
Dean whined softly at the loss, making the demon grin. "W-why did you let me come?"
"Oh." Not wanting to lose face, he made up some excuse. "I have a kink."
"For making prostitutes come."
"Oh…Weird. But I like it!"
"Here's your money." Crowley pulled out his wallet, counting out some bills. Once he set them down, he started dressing.
Dean counted out the money slowly, gasping in shock at the total. "C-Crowley? That's three-fifty! I only worked one-fifty. Why-" Looking over his shoulder revealed that the demon had vanished. Muttering, Dean sat up as he grabbed at his clothes, wiping himself clean before dressing.
Crowley went on his way, making a few deals, his thoughts on a certain hunter.
Neither knew what awaited them.