#hooker!dean

[wincestwhispers]

John watching Dean across the parking lot give a random trucker a blow job in a gross alleyway, wishing he could hear the noises he’s making too

[disguting-girl-reads]

i don't think john would directly force a teenager dean into prostitution, but he would totally give it a blind eye and never ask where the money came from so yeah hooker dean is still pretty much alive in my head 😭

[red-meat-my-beloved]

It's been a while, but I'm here with a short (302 words) hooker!dean ficlet

Also on AO3

Not moving an inch from his seat at the bar, Dean checks from his peripheral vision if the man’s still watching him.  

An unsuspecting guy, slight receding hairline, Dean guesses mid to late forties if life has been kind to him, early forties if it hasn’t. He’s dressed unremarkably for the venue -a faded flannel and jeans- but his leather shoes and shiny watch betray he has money. When Dean shifts, the man turns away noticeably, confirming Dean’s theory.

Ever since he was little, he learned how to watch for people watching him, looking for traces of suspicion in their micro-expressions, primed and ready to get out if necessary. It wasn’t until his teens he’d noticed hints of something other than suspicion in the looks of people eyeing him.

He tilts his head back, reveling in the way the last of his beer slides down his throat.

‘Watch out for Sammy’ had been the words John had been leaving them with for as long as he was leaving them. Now with funds running dry, Dean was struggling to do just that. Since he’d been caught stealing and sent off to Sonny’s farm for months, he’d been hesitant to do it again. This meant he needed cash.  

He looks at the man to find him brazenly staring back at him, now with a glint in his eye he’s more familiar with than he’d like these days. They make eye contact and the man nods, getting up from the bar and idling over to the bathrooms.

As Dean watches the door close, he idles for just a moment longer.

Then he thinks of their half a box of stale cornflakes, the two cans of Chef Boyardee in the back of the cabinet, the shriveled cucumber stub in the fridge.

He gets up and follows.

[i-know-like-four-things]

An Archive of Our Own, a project of the Organization for Transformative Works

Chapters: 1/? Fandom: Supernatural Rating: Explicit Warnings: Rape/Non-Con Relationships: Destiel, Castiel/Dean Winchester, Dean Winchester/Original Male Character(s), Dean Winchester/Other(s) Characters: Dean Winchester, Castiel, Charlie Bradbury, Jo Harvelle, Meg Masters, Sam Winchester Additional Tags: Modern AU, Sex Worker, Sex Worker Dean Winchester, Prostitute Dean Winchester, Anal Sex, Angst, Smut, Hurt/Comfort, Emotional Hurt/Comfort, Happy Ending, Top Castiel/Bottom Dean Winchester, Top Castiel (Supernatural), Bottom Dean Winchester Summary: 
Dean is happy with his life as a hooker. He loves feeling the night air on his face every night, and he is good at his job. One day he meets Castiel, the handsomest man he’s ever seen with the ugliest car in the world, and everything changes.
***
Hey y’all! I’m finally posting the fic I was talking about! Im really excited for this, so please let me know what you think!


Dean felt alive tonight. It was a beautiful fall night in Kansas City, Kasas. The breeze was present enough that Dean didn’t feel like he was drowning in his own sweat, but it wasn’t enough to make him cold. Dean was wearing his favorite pair of shorts, – the jean ones that were obscenely short and tight – this little black tight mesh top, and these little black heeled boots. He felt hot, and like he could take the whole world by storm.


Dean was leaning against the building talking to his girls.There were plenty of people working the street, but Dean, Hannah, Jo, and Charlie all stuck together. Dean and Charlie mostly worked regulars, – Charlie the chicks and Dean the gay dudes– while Hannah and Jo picked up most of the stragglers. That wasn’t to say that Dean didn’t leave with a stranger from time to time; he was the only male hooker this side of town.


Dean was chatting with Charlie, trying to look sexy leaning against a building and laughing hysterically at something she had said, and failing miserably, when the ugliest car Dean had ever seen pulled up. Jo sauntered up to the golden continental, exaggerating the swish of her hips, and leaned in the passenger window, wiggling her booty a little bit. Dean could tell the moment Jo got rejected because she dropped the sexy dance and adopted some more practical behaviors, like bending at the knees instead of the waist. She tapped the side of the car and walked back to the group.
“You’re up, Dean-o,” she announced. Dean pushed himself off of the wall he was leaning on and walked over to the car, throwing a wink over his shoulder at his friends.


When Dean walked up to the ugly-ass car, he took up Jo’s original position, resting his forearms on the open window. He looked in and was stunned.
The man sitting in the driver’s seat was absolutely breath-taking. He had this thick, dark hair that was sticking up every which way, and Dean couldn’t wait to get his fingers in it. Even sitting hunched over like the man was, Dean could tell the man was built like a ton of bricks. He had these big, elegant hands that were shakily rubbing up and down his thick thighs. His bright blue eyes kept flicking between Dean and the road in front of him, and he kept liking his plump, chapped lips.


Dean looked a little longer that he normally would have before he spoke. When he finally found the air to form words, he said, “Hey handsome. Looking for some company?” It was a cheesy line and he knew it, but Dean didn’t really care.
The man looked up at him hesitantly, meeting his eyes for a second before nodding. Dean opened the passenger side door and slid in. He buckled up and was busying himself with straightening his clothes, and he heard the man put the car in drive.


“So,” Dean began as the man started driving off, “where to?”


The man cleared his throat and said “My place,” and Dean just about died. Fuck, that man had a voice that was like wiskey and gravel and honey. If this guy got any sexier Dean’s soul might just leave his body and ascend to heaven without preamble.


“Okay,” Dean most definitely did not squeak out, “my name’s Dean, by the way.” 


“Castiel,” the man growls by way of response.


“Castiel, that’s a cool name. Mind if I call you Cas?” Dean asks.


The man nodded and said nothing else. Dean suddenly feels awkward, and starts fidgeting with his hands. Dean never gets that way. If someone gives him a bad vibe then he can talk his way out of it, usually, and he can usually make conversation with everyone else, but this was different. Something about Cas was throwing Dean off his game; he felt like a teenager going on a date. And that was dumb because one, Dean was a professional, and two, he didn’t even know the guy or have any personal connection to him, so pre-date jitters shouldn’t be an issue. And yet, Dean’s mouth was as dry as the Sahara and his hands were sweating like crazy.


The two men sat in silence for the rest of the short drive. Cas pulled into a middle-class neighborhood, and pulled his ugly car into the garage of a much prettier house. Cas shut off the car and closed the garage door before he got out, and Dean took that as his cue to do the same.


Cas walked into the house, Dean on his heels, and they made their way to the kitchen. The house was a lot nicer on the inside than the outside. Every surface held expensive knick knacks and the walls were lined with framed artifacts. Some of the frames help pictures, and some held awards, while a couple had diplomas. There was not a speck of dust in sight, and Dean was very impressed. 


“Would you like something to drink?” Cas asked.


“Sure, man,” Dean responded, wringing his hands. He still felt weirdly on-edge with this man.


“So no offence, man,” Dean began, “but you’re a good-looking guy, and I imagine you don’t have any problem scoring. So why do you need me?” Cas handed him a glass of water.


“Frankly, I don’t think that’s any of your business.” Dean raised his hands in an “I surrender” gesture and drank his water. When they were done, Cas walked off and Dean followed. They walked to what Dean assumed was the master bedroom. Cas stood off to one side and waited expectantly.


“Okay, so I charge $150 an hour, anything fancy or not vanilla needs to be discussed beforehand, and we use Pretty Woman rules; no kissing on the lips. Sound good?” 

Cas nodded at Dean’s terms, and went to get his wallet. He pulled out $150 in cash and handed it to Dean. 
“I assume you want me to bottom?” Dean asked. Again, Cas nodded his head. Cas then started using his nimble fingers to unbutton his shirt.
Dean put the cash in the back pocket of his shorts for the time being, and pulled off his top. He was working on the button of his shorts when he caught a glimpse of Cas. His shirt was discarded and he was working on his belt, but his chest is what Dean focused on. The man had well-sculpted pacts and a firm middle. He didn’t look like one of those ‘roided up, dehydrated male models, but he looked like he was carved from marble. His shoulders were thick and well-defined, and they drew Dean’s attention to the man’s perfectly sculpted neck.


And now Dean was really confused. He was just starting to think that maybe Cas’ equipment was lacking, and that was why he needed to buy his pleasure, but then Cas pulled down his pants. He still had his boxer briefs on, but Dean could tell the man was hung.
Dean shook himself out of his trance and continued to undress. He pulled off his boots, then his shorts, and lastly the little g-string he wore. Dean walked over to his shorts and grabbed a condom and a little packet of lube that he always kept in his back pocket.


Dean was always prepared before the night began. He didn’t like to think of himself as a pessimist, but many of the guys he serviced were rough and inconsiderate, and he didn’t want to take chances.


So Dean laid down on the bed and pulled out his plug that had a big plastic jewel at the end of it. He set the plug next to him on the bed, and he lubed his fingers up just a bit. He was pretty stretched out, but he made sure he could comfortably fit four fingers inside himself, just in case. When he was done, he propped himself up on his elbows and saw Cas looking at him. The man’s eyes were dark, and he had a feral edge to his gaze. If Dean wasn’t turned on by Cas’ physique, that look would have had him rock hard. 
Dean didn’t like intimacy in these situations – he just wanted to get a good fuck and move on with his life – so he turned over onto his hands and knees, facing away from Cas. Cas also seemed like he wasn’t in the mood for pleasantries, because he grabbed Dean’s hips without preamble and lined his cock up with Dean’s entrance. Cas pushed in slowly but firmly, and stilled when he bottomed out. 

Even though Dean was used to this, he still always took a moment at this point to catch his breath. It was easier when he was turned on, but he still always tried to center himself.
Without warning, Cas started to slam in and out of Dean at a blinding pace. His hips slapped against Dean’s ass with every thrust, and for all of Dean’s efforts, he couldn’t breathe. Cas changed his angle slightly and he hit Dean’s prostate so hard that Dean cried out. Dean just sat there, panting and shaking after every one of Cas’ thrusts, only to be blown out of the water again and again.


Cas reached up and grabbed Dean by the neck and shoved his face into the bed. Dean’s breaths were stifled with the bedspread, and between that, the pressure on the back of his neck and the brutal pounding he was taking, Dean was just about in subspace. Dean almost never went there, partially through sheer will, but this was just too good.


As impossible as it seemed, Cas kept fucking harder and faster. Dean was limp at this point, just letting Cas do what he wants. He was so close; he could feel heat curling in his gut, and his toes following suit.
“Cas,” he choked out, barely audible over Cas’ grunting, “I’m close.”
In response, Cas picked up the pace yet again. With one adjustment of his hips, he nailed Dean’s prostate and Dean was flying over the edge. He moaned wantonly, spilling onto the comforter underneath him. As soon as the sensation passed, Dean collapsed under Cas’ weight. Cas just let him lay there, panting, and continued to chase his release. 
After several minutes of Dean feeling blissfully full and overstimulated, Cas’ hips lost their rhythm. He jerked, grinded, and then he stilled. Cas fell on top of Dean. The two men laid there, catching their breaths and coming down from their respective highs.


Eventually, Cas got off Dean. Dean heard him walk around, take the condom off, and throw it away. Dean laid there for just a moment longer, before he lifted himself off of the wet spot he had created.


“Bathroom?” he asked horsley. Cas pointed to an adjoining room. Dean went in there and washed himself off. His head still felt foggy, and he was trying to make all his faculties work again, but he couldn’t seem to pull himself together. It wasn’t that he was complaining; he felt fucking great, it was just different than what he was used to.


When Dean was done, he walked back to the bedroom to get dressed. He found Cas had removed the comforter, and was now laying underneath the sheets. Dean dressed quickly, and pulled some small bills out of his boot, where he kept them. Cas looked about as dead as Dean felt, and Dean didn’t see him moving any time soon.


When Dean was finally dressed and ready to go, he turned to Cas. “You’re a pretty good lay,” he said, “let’s do this again sometime.” With that, Dean threw a wink over his shoulder and sauntered out of the room, scheduling an uber on his way out.

[cleighwrites]

Branching Out - Master List

SPN Fanfic

Characters - Dean, Sam, John (barely), OCs

Summary - Sam and John had been going at it for months. When it’s time for them to move, again, Dean steps in to take some of the brunt off his little brother. Things get physical, again, and this time Dean has had enough. The two of them leave John and finally branch out on their own. Dean finds out exactly what it’s like to support themselves and that he may need to seek alternative means of making money.

Word Count - 23,011 (fin)

A/N - Since this is a prequel to my Wincest Big Bang there will be some wincestual feelings. It starts out the summer before Sam’s junior year in high school. Sam, 16; Dean, 20.

Warnings - ANGST, John being an abusive asshole, prostitution, being broke, anal (first time: fingering and sex), coming out (to oneself), self doubt, and more…

Part 1 ~ Part 2 ~ Part 3 ~ Part 4 ~ Part 5 ~ Part 6 ~ Part 7 ~ Part 8 ~ Part 9 ~ Part 10 ~ Part 11 ~ Part 12 ~ Part 13

[thatsnotwhoifuckingam]

Corruption of the Corrupt Chapter 8 has arrived!

Dean’s a retired gigolo, Cas is the hot priest at the local church that he can’t stop daydreaming about.  Once disgraced, Cas moves away and Dean can’t get him out of his head.  Can Dean get through to him before Mick Davies steals Cas heart?

New to the story?  Click here for Chapter 1.

Dean grabbed the stack of towels from the dresser in his room and couldn’t help but smile.  Everything was perfectly in place. Cas didn’t appear to be anything close to a neat freak but this place was spotless and it made him want to break Cas out of that sense of order.  To take him apart until all he wanted was sex and the air he needed to breathe. Realization of such carnal intentions made his stomach turn. Frustrated by his inability to think past his dick, he slammed the door just a touch too hard on his way to the bathroom and shocked Cas out of his daydreaming.

Castiel jolted upright from his position in his bed wondering if something had happened.  Maybe it was too much to ask Dean to go out after such a long flight, or worse, maybe the formality of an actual date was upsetting him. He weighed what to do and listened to the shower start up in the bathroom.

Dean scrubbed a little too hard on his skin in frustration, the pain slowly bringing him back to himself. He could do this. He could stay away from Cas long enough to prove himself. Cas deserved all the effort he could drum up so come hell or high water, he’d keep his dick in his pants.  After a quick rub of his hair, he toweled off, popped in his ear buds and cranked up the music while he brushed his teeth and rushed through a quick shave. He gave himself a long look in the half fogged mirror. If the tented towel he was wearing was any indication, his body was going to make this hell.

Once Cas had worked himself into a nervous mess over analyzing every little thing that had happened since that kiss in the airport, he decided he needed to check on Dean.

He padded down the hall to the bathroom door in his socks and knocked softly. “Hey, Dean, if you don’t want to go out, I don’t want to push you…” the door popped open as he spoke.  As the steam billowed out of the tiny bathroom, Dean’s half naked and startled form filled the doorway. Towel tied so low around his hips the neatly trimmed curls just peeked out, wet hair rubbed into a sexy riot on his head, and a look that said he had no idea Cas had been at the door.  Hands full of dirty clothes and toiletries he struggled with what to do and how to make this look less like a cheap porno.

“Fuck.” Cas whimpered but Dean couldn’t hear him any more than Cas wanted him to.  Dean turned his cheek to show Cas the earbud so Cas plucked it from his ear and dropped it onto his damp, freckled shoulder. Jesus. He swallowed hard, willing his erection away and glad it was pinned down by a layer of denim.  Dean wasn’t so fortunate.

“Cas, hey, uh...I’m sorry. I hear you knocking. Did you need the bathroom?” He cleared his throat and thought about anything he could think of to deflate his desire.  Grandma. Dead folks. Festering wounds. There we go….

Cas’ face was flushed and words weren’t coming easy.  His fingers itched to give that towel a quick tug. “Uh, no, I just wanted you to know that it was absolutely fine if you didn’t want to go out.  I was a little concerned that maybe you felt coerced.”

“Coerced?  Aw, Cas, no.  I can’t wait to just relax and spend time with you and have my first official date.” Dean’s smirk spread into a full blown grin as Cas looked away and tried to hide his embarrassment.  Flattery wasn’t something he was used to. When Mick did it, it made him uncomfortable but when Dean does it he just craves more.

Cas blushed and looked at the floor to try to hide a grin before turning to walk back to his own room.  Keeping his hands to himself was hard but Dean had a point. They were trying to decide if this could really go somewhere.  He needed to find some self control.

Dean almost ran back to his room and locked the door behind him. If he was gonna make it through this night, he was gonna need to give his dick some relief or it would never calm down. Dropping everything into a pile on the floor, he all but threw the towel across the room and leaned back against the door, taking his defiant cock in his hand. That first easy stroke curled his hips and stole his breath as his mind painted a picture of Castiel’s perfect mouth wrapped around him.

Read more of Chapter 8 here!

[kansaskissedlips]

Do you think Dean ever prostituted himself out when he was a teenager just so he could let Sam have a childhood? How do u think Sam would react if he found out now as adults and as a couple? Like upset but touched or angry? Ahhhh. My heads running away with how Sam would be holding back tears as Dean tells him. And oh my god the slow sex afterwards to reassure Dean he doesn't think less of him and he wishes he didn't have to do it.

AHHHHHH. 

[wincestwhispers]

stanford era Dean could’ve charged $1000 per hole and people would’ve gladly paid for it