A/N I don't own Supernatural. Written for a youtube comment. Based on the video: Dean Winchester; Ex's and Oh's created by Roarkshop
Dean Smith had three ways of staying sane, drinkin',brawlin' , and a long slew of one night stands. He only really remembered eight. The only names he remembered out of hundreds, Sam Wesson, Castiel Novak, Crowley MacLeod, Benny Laffite, Meg Masters, Cain Mark, Rowena MacLeod, and Abaddon Knight. Out of those eight he only missed four. Out of those four he only still harbored romantic feelings for two. Benny and Meg were the best friends a psychiatrist for criminals could ask for. Benny had been through hell with a gang of chain smokers called, The Vampires. He had done a lot for the gang, they were his family, then they beat him within an inch of his life and left him to die behind a club called Purgatory. Dean had found him there and had taken the man to the hospital. Then they started screwing. They stayed together for half a year and then Dean left him. Feelings were dangerous when you were Dean Smith, he always fucked up relationships. Meg Masters was a nurse at his mental hospital. She quit when she saw Dean making out with another nurse in his office. Sam and Cas were the best people to ever have a romantic relationship with. He still loved them. He knew he had no right to after what he did.
He met Sam when the kid was barely twenty one. He had been twenty five and had been drawn to the innocence in Sam's eyes. He taught him everything in that month they had been having sex. He remembered the look on Sam's face after a round of sex.
"Hey,where are you going?' Sam asked when Dean rolled out of bed the first night they screwed.
"Just the bathroom, I'll be back in a minute sugar.Nature calls."Dean quickly went to the bathroom and was done in a minute.When he came out Sam had this puppy eyed look on.Exuding innocence, though no one still believed he was innocent after that wonderful bout of sex.
"You said something about another round?" Dean growled and Sam laughed as Dean launched onto the bed.The laugh quickly turned to a moan as Dean's teeth latched onto his neck.
Dean had only left because Sam mentioned Dean moving in. The thought of getting that attached terrified him. So he ran out to his Baby, a '67 Impala, with Sam hot on his heels. He jumped into the driver's seat and drove away with Sam calling after them.
Dean met Cas on a vacation to California. He had left South Dakota to get away from Sam for a month or two until the boy gave up on him. Everyone else did, so Sam would to. He had been at a bar when he saw this man with messy brown hair and the bluest eyes Dean had ever seen. He thought a one night stand would help him get over Sam. They had sex and a pretty good relationship until Cas saw Dean's laptop internet dating with Crowley from the U.K. It had been hacked ,but Cas didn't believe him. Dean went back to South Dakota and quickly sent some emails from Sam to Cas and got them to start dating. At least someone was happy.
Dean started dating Crowley to get back at Cas, even though the blue eyed angel of a man wouldn't know. However, Crowley turned out to be a possesive jerk so Dean stopped seeing him. In anger, Crowley leaked nudes of Dean on the internet. Dean decided to get payback of the worst kind and started to have sex with Crowley's mother, Rowena. The older woman was attractive enough and Dean spammed Crowley's inbox with pictures of him and Rowena having sex.
Abaddon and Cain had been two dominants he met at a BDSM club. He decided, however, that he didn't like all the knife and blood play they were into, but only drew the line when Cain wanted to give him a brand. Not just a tattoo, but a full on white hot metal brand.
Dean started to think about what he'd done with his life, the slew of men and women alike he'd banged and left. The amount of times he had bought a drink and gotten a quickie behind a bar in payment. All the times he had stared unfeelingly into the eyes of one of his lovers as they cried. All the times he had looked at someone and thought 'I will have them tonight'. All the physically painful fights he'd had with angry dates. All the times he ran away from a date he remembered. All the times he had gotten slapped or punched by one he didn't.
"I'm done," he said aloud. He needed to man up and deal with his life. He quickly looked up the next AA meeting and wrote it down on his calendar. Then he grabbed his cell and dialed a number he hadn't called in a year. It rang about five times before the recipient answered.
"Give me one reason I shouldn't tell you to fuck off and go back to watching Star Wars with my boyfriend."
"I'm sorry Sam. Look, I just want to talk to you both. Can you ask Cas to pause it and put the phone on speaker? Just listen to what I have to say then you can either come over to my apartment and punch me or not," Dean heard and audible sigh then a muttered "Hold" from Sam. He heard Cas start yelling and then a defeated sigh.
"What the fuck do you want Smith?" Dean winced at the coldness of Cas' voice.
"Hello, Castiel. I just want to talk, I know you don't believe me, but I wasn't internet dating Crowley. A girl named Lilith hacked into my computer and started dating Crowley, to hide it from her parents she used my computer. I have the messages to prove that I wasn't dating him. I did date him afterward because I was mad at you," Cas deserved the whole truth, "but I didn't cheat on you."
"I don't quite believe you, but alright."
"Then why did you leave me?" Sam's angry voice said steadily into Dean's ear.
"I was afraid of commitment, every time I get too attached something bad happens. I was engaged to a woman named Lisa once and we, her, her son Ben, and I, were driving and got into an accident. Her and her son lost their memories. I had another girlfriend who broke up with me because, frankly, I'm a mess. I spend all day listening to criminals that are so messed up they need drugs. No one ever stays, and when you asked me to move in with you I got scared. I'm sorry. You can come over and punch me if you like I'm at apartment 2E at Harvelle's apartment complex." There was a long silence.
"You know what? How about you come over to our apartment, 4D at Paradise apartment building and we all marathon the Indiana Jones movies. We can talk more after," Cas' quiet voice shyly suggested.
"Really? I mean…Really?" Dean was flabbergasted. "Thank you…"
"Yeah, yeah just come over ya'big jerk," Sam lightly chuckled.
"Bitch." Dean was so happy. He quickly said goodbye and rushed to Baby. He smiled as hestarted to drive to Paradise apartment building. "Things are lookin' up Baby, things are looking up."