SPN: Mistakes We Make 09
Summary: All-human AU. From the ages of 10 - 15, Dean and Castiel were inseparable. Then Dean's dad died, and rather than lose his brother to CPS, Dean took him and ran. Years later, Castiel's big brother Gabriel finds Dean working as a prostitute, and decides to try and help him - but does Dean want to be saved?
Warnings: Language (is that even worth mentioning by now?), sexual references (for a story about prostitution, there hasn’t been much actual sex yet)… I think that’s it. This one’s fairly tame. Just wait until next chapter though - we’ll be back with Cas and Gabriel.
-MWM-
When they were both sated, Crowley and Dean lay on the bed together. They were most assuredly not cuddling, but Crowley did have a possessive hold on Dean’s hip. There was silence for several minutes, broken only by the sound of their breathing getting back under control, before Crowley spoke.
“Ground rules now, Dean. This isn’t a relationship. This isn’t exclusive, I will be screwing other people and you’re allowed to as well. You ever want me to stop doing something, you speak up. Otherwise I’ll continue to fuck you whenever we’re both in the mood. Understood?”
Dean blinked for a moment, taken aback by Crowley’s straightforward speech. Then again, Crowley had always been upfront about the conditions he placed on things, even if he did have a way of speaking that made the listener want to go along with whatever he said. He’d also been a good first lover, and while Dean knew he’d be sore later, he hadn’t actually been hurt. It had felt amazing, in fact.
So he nodded, making up his mind. Casual sex with Crowley would be okay with him.
“Excellent,” Crowley grinned, then leaned in to kiss him again. Dean was happy to welcome him back, even if he wasn’t ready for another round just yet. Crowley pulled back soon and swept his eyes up and down Dean’s body, appraising him yet again.
“You’re a pretty quick learner. Not bad on the eyes either. Flexible too. If you want to change jobs, I’m sure we won’t have trouble finding customers for you.”
It took a few seconds for the meaning of the words to sink in, and Dean couldn’t help but stare at Crowley.
“I… uh, that is…”
“Just think about it,” Crowley grinned at the noises Dean was making. “I’d rather you make this decision when you’re sober. Now come on, time to get dressed and mingle again.”
Dean groaned and tried to bury his head under the pillow. When he felt a sharp smack to his backside, however, his whole body jerked and he looked at Crowley in shock.
“None of that. Get moving.” The boss was dressed fairly quickly and left, though not before pressing one last kiss to Dean’s lips.
Dean continued to sit on the bed for several minutes, trying to think. In the end he gave up and dressed himself, slipping back to the party. Danni caught his eye not long after and winked at him, causing Dean to flush for a second before winking back. Apparently having sex with Crowley wasn’t uncommon for the workers. He was fairly sure he should be feeling used right about now, but since no one else was making a big deal about it, he figured he’d let it be for now too. There would be plenty of time to freak out tomorrow.
-MWM-
A few days later, Dean was sitting in Crowley’s office. He remembered everything that had happened at the party, since he hadn’t been that drunk, and had been thinking about the offer Crowley had made. He’d thought about it a lot, and had come to a decision.
“You sure?” Crowley raised an eyebrow. “I’m certain you’d be good at it.”
“Thanks sir, but no thanks. I just don’t feel comfortable sleeping with strangers.”
“Fair enough,” Crowley nodded. “It’s not for everyone.” He waited a beat before continuing. “I notice you didn’t say you don’t feel comfortable getting paid to sleep with someone. It’s the being strangers part that you don’t like?”
“Yeah,” Dean shrugged. “After working here so long, money for sex doesn’t seem like such a big deal any more. But I really don’t think I could have sex with a stranger.”
“And what about sleeping with me?” Crowley asked, leaning back in his chair a little. Dean paused, making sure he wasn’t going to say something to offend his boss.
“That’s different, ‘cause you’re not a stranger. I know it’s not a relationship, that there’s no feelings beyond being horny, but I know you. I guess… I feel safer getting into bed with you than with someone I don’t know.”
“Hmm. Okay,” Crowley hummed in agreement. “Good to see you’re being sensible about this. But if you ever change your mind, all you have to do is say the word.”
“Thankyou sir,” Dean grinned in relief. He wouldn’t admit it aloud, but the thought had crossed his mind that Crowley might make him become a prostitute against his will. After all, he was still so far in debt to the older man that it was going to take years to pay off - and until it was paid, he was well aware that Crowley owned him. Thus far however, he’d been a generous boss, so Dean wasn’t going to push his luck.
So when Crowley pushed his chair back from the desk a little and crooked his finger in a ‘get over here’ motion, Dean went willingly and showed Crowley just what he’d learned about giving a good blowjob.
-MWM-
On Sam’s birthday, Dean decided to splurge a little - he had some money saved up - and bought his brother a new laptop of his own. Sam was thrilled, going so far as to hug Dean for several minutes.
“Easy there kiddo,” Dean couldn’t help grinning. “It’s not that great a computer, trust me. I just figured it was about time you had one of your own. After all, pretty sure you don’t want me looking through your porn collection.”
“I don’t have a porn collection!” Sam exclaimed, blushing bright red. Dean raised an eyebrow.
“Seriously? You don’t? What’s wrong with you?”
“Nothing! I’m just not into that stuff.”
“What stuff? Sex? How can you not be into sex? You’re a teenage boy!”
“I’m fourteen,” Sam ground out. “I’m not supposed to be into sex yet.”
“C’mon, my first kiss was only a week after I turned fourteen. We Winchesters mature early.”
Sam opened his mouth to say something, then closed it again. Dean had caught the movement though, and raised an eyebrow.
“Out with it. What were you gonna say?”
“Well… your first kiss. Was it with Cas?”
Dean froze, then slowly nodded. He’d been the one to bring it up, after all, may as well resign himself to talking about it.
“We’re gonna have a chick-flick talk, aren’t we?” Dean asked in a last-ditch effort to avoid the subject. Sam just gave him a Look, and he sighed. “Yeah, it was Cas. He sorta jumpstarted my maturity.”
“What was it like?”
Dean considered carefully before answering. He still remembered, clear as day, everything he’d felt the first time Cas had made a move on him.
“Confusing as all hell. But nice. I mean, I’d never even considered him that way - he was my best friend, and I’d thought that was that. Then he kissed me to make me shut up about how I was worried about you being sick, and I realised how right it felt.”
“Did you love him?” Sam looked a little uncomfortable, though whether it was from talking about Dean’s love life or remembering Castiel was hard to tell.
“Yeah, I think I did. Still do, actually,” Dean admitted.
“So why didn’t we go to him when Dad died?”
“Because he wasn’t talking to me,” Dean looked at the floor, the pain coming back full force. “After him and his brothers left for New York, Cas didn’t call me once, and he didn’t answer when I rang him. Neither did Gabriel. I guess Lucian’s disapproval got too much for him.”
“I thought Lucian liked you?” Sam was clearly confused. Dean sighed, remembering having this conversation right before Castiel left.
“Yeah, but he had issues with Cas. I don’t know all the details, but they didn’t get along well, and he didn’t like that me and Cas were seeing each other as more than friends.”
“Oh.” There was a pause for a moment while Sam considered. “Lucian was a dick.”
Dean couldn’t stop the laughter that erupted at that. Though he and Sammy were different in so many ways, there were some things that they agreed on perfectly. One of them being the douchiness of Lucian Novak.
Prev Next
Warnings: Language (is that even worth mentioning by now?), sexual references (for a story about prostitution, there hasn’t been much actual sex yet)… I think that’s it. This one’s fairly tame. Just wait until next chapter though - we’ll be back with Cas and Gabriel.
-MWM-
When they were both sated, Crowley and Dean lay on the bed together. They were most assuredly not cuddling, but Crowley did have a possessive hold on Dean’s hip. There was silence for several minutes, broken only by the sound of their breathing getting back under control, before Crowley spoke.
“Ground rules now, Dean. This isn’t a relationship. This isn’t exclusive, I will be screwing other people and you’re allowed to as well. You ever want me to stop doing something, you speak up. Otherwise I’ll continue to fuck you whenever we’re both in the mood. Understood?”
Dean blinked for a moment, taken aback by Crowley’s straightforward speech. Then again, Crowley had always been upfront about the conditions he placed on things, even if he did have a way of speaking that made the listener want to go along with whatever he said. He’d also been a good first lover, and while Dean knew he’d be sore later, he hadn’t actually been hurt. It had felt amazing, in fact.
So he nodded, making up his mind. Casual sex with Crowley would be okay with him.
“Excellent,” Crowley grinned, then leaned in to kiss him again. Dean was happy to welcome him back, even if he wasn’t ready for another round just yet. Crowley pulled back soon and swept his eyes up and down Dean’s body, appraising him yet again.
“You’re a pretty quick learner. Not bad on the eyes either. Flexible too. If you want to change jobs, I’m sure we won’t have trouble finding customers for you.”
It took a few seconds for the meaning of the words to sink in, and Dean couldn’t help but stare at Crowley.
“I… uh, that is…”
“Just think about it,” Crowley grinned at the noises Dean was making. “I’d rather you make this decision when you’re sober. Now come on, time to get dressed and mingle again.”
Dean groaned and tried to bury his head under the pillow. When he felt a sharp smack to his backside, however, his whole body jerked and he looked at Crowley in shock.
“None of that. Get moving.” The boss was dressed fairly quickly and left, though not before pressing one last kiss to Dean’s lips.
Dean continued to sit on the bed for several minutes, trying to think. In the end he gave up and dressed himself, slipping back to the party. Danni caught his eye not long after and winked at him, causing Dean to flush for a second before winking back. Apparently having sex with Crowley wasn’t uncommon for the workers. He was fairly sure he should be feeling used right about now, but since no one else was making a big deal about it, he figured he’d let it be for now too. There would be plenty of time to freak out tomorrow.
-MWM-
A few days later, Dean was sitting in Crowley’s office. He remembered everything that had happened at the party, since he hadn’t been that drunk, and had been thinking about the offer Crowley had made. He’d thought about it a lot, and had come to a decision.
“You sure?” Crowley raised an eyebrow. “I’m certain you’d be good at it.”
“Thanks sir, but no thanks. I just don’t feel comfortable sleeping with strangers.”
“Fair enough,” Crowley nodded. “It’s not for everyone.” He waited a beat before continuing. “I notice you didn’t say you don’t feel comfortable getting paid to sleep with someone. It’s the being strangers part that you don’t like?”
“Yeah,” Dean shrugged. “After working here so long, money for sex doesn’t seem like such a big deal any more. But I really don’t think I could have sex with a stranger.”
“And what about sleeping with me?” Crowley asked, leaning back in his chair a little. Dean paused, making sure he wasn’t going to say something to offend his boss.
“That’s different, ‘cause you’re not a stranger. I know it’s not a relationship, that there’s no feelings beyond being horny, but I know you. I guess… I feel safer getting into bed with you than with someone I don’t know.”
“Hmm. Okay,” Crowley hummed in agreement. “Good to see you’re being sensible about this. But if you ever change your mind, all you have to do is say the word.”
“Thankyou sir,” Dean grinned in relief. He wouldn’t admit it aloud, but the thought had crossed his mind that Crowley might make him become a prostitute against his will. After all, he was still so far in debt to the older man that it was going to take years to pay off - and until it was paid, he was well aware that Crowley owned him. Thus far however, he’d been a generous boss, so Dean wasn’t going to push his luck.
So when Crowley pushed his chair back from the desk a little and crooked his finger in a ‘get over here’ motion, Dean went willingly and showed Crowley just what he’d learned about giving a good blowjob.
-MWM-
On Sam’s birthday, Dean decided to splurge a little - he had some money saved up - and bought his brother a new laptop of his own. Sam was thrilled, going so far as to hug Dean for several minutes.
“Easy there kiddo,” Dean couldn’t help grinning. “It’s not that great a computer, trust me. I just figured it was about time you had one of your own. After all, pretty sure you don’t want me looking through your porn collection.”
“I don’t have a porn collection!” Sam exclaimed, blushing bright red. Dean raised an eyebrow.
“Seriously? You don’t? What’s wrong with you?”
“Nothing! I’m just not into that stuff.”
“What stuff? Sex? How can you not be into sex? You’re a teenage boy!”
“I’m fourteen,” Sam ground out. “I’m not supposed to be into sex yet.”
“C’mon, my first kiss was only a week after I turned fourteen. We Winchesters mature early.”
Sam opened his mouth to say something, then closed it again. Dean had caught the movement though, and raised an eyebrow.
“Out with it. What were you gonna say?”
“Well… your first kiss. Was it with Cas?”
Dean froze, then slowly nodded. He’d been the one to bring it up, after all, may as well resign himself to talking about it.
“We’re gonna have a chick-flick talk, aren’t we?” Dean asked in a last-ditch effort to avoid the subject. Sam just gave him a Look, and he sighed. “Yeah, it was Cas. He sorta jumpstarted my maturity.”
“What was it like?”
Dean considered carefully before answering. He still remembered, clear as day, everything he’d felt the first time Cas had made a move on him.
“Confusing as all hell. But nice. I mean, I’d never even considered him that way - he was my best friend, and I’d thought that was that. Then he kissed me to make me shut up about how I was worried about you being sick, and I realised how right it felt.”
“Did you love him?” Sam looked a little uncomfortable, though whether it was from talking about Dean’s love life or remembering Castiel was hard to tell.
“Yeah, I think I did. Still do, actually,” Dean admitted.
“So why didn’t we go to him when Dad died?”
“Because he wasn’t talking to me,” Dean looked at the floor, the pain coming back full force. “After him and his brothers left for New York, Cas didn’t call me once, and he didn’t answer when I rang him. Neither did Gabriel. I guess Lucian’s disapproval got too much for him.”
“I thought Lucian liked you?” Sam was clearly confused. Dean sighed, remembering having this conversation right before Castiel left.
“Yeah, but he had issues with Cas. I don’t know all the details, but they didn’t get along well, and he didn’t like that me and Cas were seeing each other as more than friends.”
“Oh.” There was a pause for a moment while Sam considered. “Lucian was a dick.”
Dean couldn’t stop the laughter that erupted at that. Though he and Sammy were different in so many ways, there were some things that they agreed on perfectly. One of them being the douchiness of Lucian Novak.
Prev Next