Disclaimer: I do not own Supernatural. But if I did, I'd get Misha a bodyguard so he doesn't get attacked again!

AN: Hi, all! Here's the next chapter in the Sexcapades of Squirrel. This one was co-written by Gina and I. All the stuff with Jordan is hers, mine is the before and after. LOL. And the song is by Theory of a Deadman. The fic is loosely based on it, if that gives you any hints! Hope you all enjoy!

Warnings: None that I'm aware of. Cursing, smut, alcohol, that's about it.

I Hate My Life – A Sexcapades of Squirrel Story

Dean's eyes narrowed as he walked past the guy begging for change. He dropped a buck in, because, hey, shit happened to people. He noticed Sam dropped a couple of bucks in as well as they walked back to the Impala. "You know, some days, I wish that was us," Dean stated as he looked over the roof of the car at his brother.

"Begging on a street corner?!" Sam asked indignantly.

"Yeah. Beats the hell out of this life sometimes," Dean muttered as he slipped in behind the wheel. Sam blew out a breath as he slid into the passenger seat. "What?"

Sam shook his head.

"Don't do that. You got a problem? Say it."

"Dean, that guy...he's living on the street for crying out loud!"

"Yeah? So? No monsters to hunt, no death tattoo on his arm..."

Sam's eyes cut to Dean's cloth covered arm where The Mark of Cain was perched and Dean sighed. "All I'm saying? He sits on a fucking street corner. That's it. He may be homeless, but he's got a hell of a lot less complicated life than we do."

"You're acting like an ungrateful brat."

Dean glared at him. "And you're bitching at me like you're my wife, Sam! Geez! If I can't bitch and whine to you, who can I?"

Sam rubbed his eyes with his middle finger and thumb. "I'm just saying, we could have it a lot worse."

"I was a demon, Sam. You were Lucifer. Explain to me how much worse our lives can get?!"

Sam shot him the bitchface. "You know what? Forget homicidal, that damn mark is turning you into a whiny bitch!"

"You're the bitch, bitch."

Sam sighed again and rolled his eyes. "Look, let's just..." he sucked in a breath then blew it out. "Look, I'm glad you're attempting to clean up your life a little bit, and I'm glad you're not drinking as much, but, damn it, I think you need to get a drink. Drop me off at the motel, let me do the research. Go get plowed, get laid, and come back in the morning with a better fucking attitude, okay?"

Dean blinked. "You..." He thought a moment. That...didn't sound like a bad idea. "Fine," he bit out, almost grateful for Sam's suggestion. "I'll do that."

"Good."

They didn't speak until Sam got out of the car. He leaned back in and glared at Dean. "I mean it. Don't come back until you're lit and laid."

"Thanks, you're so fucking kind," Dean growled. Sam slammed the door and Dean tore ass out of the parking lot, squealing tires as he went.

He drove to the nearest bar and walked in. It wasn't a dive, it was actually a fairly decent place, complete with a bouncer at the door, checking I.D.'s. Dean sauntered up to the bar and plopped his ass on a bar stool.

"What ya have?" the bartender asked.

Dean ordered a beer, just to get him started, along with a shot of whiskey. He downed the shot, and took a sip of the beer before he looked around. His eyes zeroed in on an ass that wouldn't quit wrapped in denim so tight, he didn't know how she was breathing, but it was working for her. She had on too much makeup, and she was laughing a little too hard at some other chick's joke, but he shrugged and leaned over. "What's so funny?" he asked her.

She turned and gave him a dazzling, toothy grin. "Inside joke between my girl over there and me." She held out a dainty hand. "Jordan."

"Dean."

She looked him up and down and he didn't need Sam's college education to know she was sizing him up. He cleared his throat. "My eyes are up here, honey."

Her grin grew as she licked her lips. "Yeah, but..." she slid closer to him and her hand hit his thigh, then kept going, right up to little Dean, who was growing by the damn second. "No matter how pretty they are, this is what I'm interested in."

His eyebrow shot up. "Direct, huh? I like that. Wanna get out of here?"

"Sure," she purred as she leaned in to kiss him. It started off soft at first, but then she nearly devoured him as she threw her arms around his neck.

He couldn't help the moan as he managed to shove his hands into the back pockets of those jeans, squeezing her ass as she fisted a hand in his hair, tugging a little rougher than he liked.

Suddenly, she was pulled from his arms and a guy about Dean's height and build yelled, "Say goodnight, Jordan!"

"H-Hey!" she shouted as he pulled her roughly toward the door.

Dean instinctively grasped her around the waist, pulling her back to him. "The hell's your problem, pal?" he growled, guarding her as he stepped between the guy and Jordan.

The man looked around Dean to stare Jordan in the eye. "She's leaving. Now!"

"Sorry, bud, you're gonna have to do better than that," Dean stated arrogantly. "She may not have come with me, but she's here with me now, and guess what? She's planning on leaving with me. So, just go on. She's not interested. Go on back home. Unless you wanna try me. Think you could throw me outta here? Be my guest."

The guy narrowed his eyes and stepped so close to Dean, they were almost touching noses. The guy's tone was nothing but dangerous as he growled through clenched teeth; "Well, as her FATHER, trust me when I say it'll be my absolute PLEASURE to kick your ass out of here."

Dean blinked, frozen. The man looked him up and down. "You're still standing between me and my daughter, who happens to be SEVENTEEN, jerkoff. You wanna move? Or are you going to make me put your lights out, first?"

Dean knew a bluff when he saw it, and this was not one. He cleared his throat. He swallowed hard. "No sir," he whispered as he stepped aside. "Sorry."

They guy was still eyeing him as he snatched at Jordan, who pulled Dean in for another searing kiss.

"Young lady, you're in enough trouble already!" her father yelled at her, tugging her away.

She slipped something into Dean's hand. "Call me!" she yelled before sending him a wicked smirk and a wink.

Wide eyed, Dean glanced down at his hand where a phone number was written on a napkin.

He staggered back to his stool and fell onto it. With a sigh and a head shake, he muttered, "Fuck my life."

The next night found him sitting on the same barstool. They'd ganked the monster, saved a civilian, and were big damn heroes. Sam was going back to take a shower, but Dean just needed a little something to take the edge off. After not managing to get laid the night before, coupled with almost feeding some teenager's daddy fetish, he just needed to regroup. He'd gone back to the motel shell-shocked, prompting Sam to look at him worriedly. Well, at least he hadn't murdered anyone, right? That had to count as a damn win. Didn't it?

He ordered a beer along with a couple of shots and was lining them up to drink when he heard a voice purr from behind him, "Hey, you."

Wide eyed, he turned around slowly. Sure enough, it was Jordan, wearing a red dress that fit her like it should be thanking her. His eyebrow shot up. "NO."

"What?" she pouted playfully as she wrapped a lock of hair around her finger, twirling it innocently.

He shook a finger at her. "NAH-uh. Keep movin', Juno. The last thing I need is to star in my own episode of 'Teen Mom'."

She laughed throatily and wrapped an arm around his neck, fingering his hairline lightly as she got into his personal space. She ran a finger down his chest and with a flirty smile, said, "Now, Dean, are you trying to tell me you didn't have fun last night?" Dean stood stock still. Her smile grew predatory as she pushed into him. "Are you trying to say you don't want to take this out for a spin?" She put his hand on her hip. "Trust me, I know what I'm doing. I know how to treat you right, Daddy."

He held up both hands like she had a gun on him. She put a hand on his face and breathed, "I promise, I can make you feel so good."

Dean closed his eyes and muttered to himself, "There's no pie in jail, there's no pie in jail, there's no pie in jail..."

He grabbed both her wrists, forcing her hands to her sides. "First of all," he looked her up and down, unable to help himself. "DAMN. That dress is sin."

With a smile, she began to lean in again.

"No. STAY!" he commanded. He shook his head, trying to rid himself of the mental imagery. And it was oh...so...inventive. "Second of all, if the 'fun' you're referring to is that standoff I had with your old man? Yeah, that was LOADS of fun. Thanks. Can't wait to do it again."

"I didn't peg you as the type to back down from a challenge so easily," she stated with a playful smirk.

He shot her a look. "No way in hell I'm biting THAT hook. A challenge I can handle, trust me, but not one that tacks on five-to-ten." He stared off in thought a moment before looking back at her. "Seriously, how did you even get in here?"

She moved a step closer as she said, "Let's just say the guy working the door doesn't play hard-to-get nearly as well as you do."

"Wow," he stated, feeling a mixture of surprise and pity. He glanced at the dress again. "Red's definitely your color, 'cause you're the devil. And trust me, that's not a compliment. I've met the bastard." At her confused look, he pushed her away with a single fingertip to her shoulder so his intentions couldn't be misread. "And FYI, that information just earned the douchebag at the door a beatdown, not to mention a cell mate named Bubba. Hope he likes it rough..."

For the first time, her composure slipped as she whined, "What?! You can't do that!"

He smiled, feeling back on his game. "Sure I can. It's one of the privileges of being a grown-up." Downing one of the whiskeys behind him, he added, "Consider it an apology to your old man."

"I'll never be able to get in here again!"

He leaned back on one elbow. "And that's a bad thing?"

She just looked at him, wide eyed, mouth all but hanging open, speechless.

He turned and asked the bartender, "Buddy! Can you call a cab? I'm pretty sure I'm about five seconds from a meltdown here."

The bartender nodded and Dean turned back to the girl as she screamed, "You...YOU ASSHOLE!" She stomped her foot. "I'm not a kid, and not you, not my dad, NO ONE is gonna tell me what to do!"

He finished his beer then got to his feet. "See? THAT'S how a teenager's supposed to act." He grasped her arm and began moving.

"What the hell do you think you're doing?!"

"You're going home. It's past your bedtime."

"Like hell!" she spat as she pulled her arm away from him. "You may be as old as my dad, but you ain't him, so let. Me. GO!"

"HEY!" he barked. He started to argue but instead, popped an eyebrow. "I may not be Bieber or whoever, but it sure as hell worked for you."

Her mouth fell open. "Oh! You mother..." she slapped his face. Hard.

"Ow, dammit!" he growled, rubbing his cheek. She moved to swing again and he grabbed her wrist. He leaned in close and warned, "Don't let this pretty face fool you, honey. I ain't above carrying you outta here unconscious if I have to. So? You done yet?"

She jerked her wrist out of his hand and squared her shoulders. "Jerk," she muttered.

Like a reflex, Dean shot back, "Bi-ahhh..." He winced and rubbed the back of his neck.

Her eyes narrowed. "What did you just say?!"

He cleared his throat. "Never mind. Let's go."

Surprisingly, she let him lead her to the door. As they approached the bouncer, Dean pointed at the girl next to him. "You know her?"

The bouncer chuckled nervously. "So many girls are in and out of here, man, it's hard to keep track, you know?"

Dean had been trained in reading bullshit since he was a child and he read the recognition in the guy's eyes immediately. "Yeah, I bet," Dean murmured. They moved through the door and Dean threw an elbow into the guy's face, knocking him against the wall. The bouncer slid down to the floor, clearly unconscious. With a sneer down at the body, Dean stated, "Don't move. I'll be right back to finish this."

Dean was surprised to find the cab already waiting outside. He opened the back door and shoved Jordan into it. Squatting down, he pointed at her. "Don't think I won't find out if you end up anywhere but home."

"Whatever, Grandpa," Jordan replied, crossing her arms.

"You're welcome, by the way," Dean growled as he slammed the door. He walked around to the driver's window. He leaned in and waved a fifty in the driver's face. "See this? TAKE. HER. HOME. Don't pass go, don't...well, you know the rest."

"You got it," the driver said, dropping the money into his shirt pocket.

Dean took a step back as he watched the cab pull away. He scrubbed his hand over his face and groaned, "Holy shit. What a night."

He walked back into the bar and moaned as he saw the bouncer, still out of it. "Hell, I'll deal with you later," he sighed, swatting his hand in the idiot's direction. He stepped over the body and plopped back down at his seat. He looked at where the shot glasses had been lined up. Apparently the bartender hadn't figured he was coming back. "Damn." he waved a hand at the bartender and pleaded, "Whiskey. Double."

He heard a feminine giggle coming beside him. He downed the drink and glanced over. She was wearing jeans that fit her just right and a top that showed off cleavage you could die happy in. The woman smiled at him.

"Well, hello there," he stated with a smile to match.

She leaned into him and whispered, "You look like you could use a little company."

He opened his mouth to accept her offer before he remembered the night's event's thus far. "Wait...are you over twenty-one?"

Laughing throatily, she replied, "Wow. You flatter me. Yeah, I am. And then some." She looked him up and down. "I'm probably older than you are, gorgeous."

He flashed her a boyish grin. "Is that so? Well then, by all means, let me buy you a drink."

They sat and talked a while. She was flirty, fun, sexy...he needed in her pants. So by the time the bar closed, and she purred, "Let's get out of here," into his ear, he was all too willing to comply.

He followed her back to her car and slid into the passenger seat, to let her run the show. She tried to give him the whole 'I don't normally do this kind of thing' line and he half bought it until she pulled up at the motel he and Sam were staying in. She smiled and said, "I think we should get a room, don't you?"

How could he argue? He could cut glass with his dick. He needed this. Now. But he didn't want to appear too eager. "Sure, sugar. Want me to...?"

She shook her head and winked. "I got this."

He watched her walk in and he whimpered before sending Sam a text; "About to be a very happy boy, Sammy. See you when I see you."

Sam sent a green faced sick emoji and Dean chuckled. It was followed by the comment, "Stay safe."

Dean rolled his eyes. Like he didn't know how to stay safe. He snorted and sent back, "I've got my angel blade."

This time Sam just sent back a colon and a capital P - two eyes with a tongue sticking out. Dean was still chortling when she came back. "Something funny?" she asked.

He shook his head. "I just wanted to check in with my brother. He worries."

She eyed him but didn't comment as she drove and parked a few parking spaces down from the Impala. He glanced at his baby before he followed the woman into the room. "You know," he stated as he broached the door, "I usually make it a point to know the names of the women I'm having sex with."

She sidled up to him. "What do you want it to be?"

He shot her a deadpan look. "Okay, listen, I've been burned before. I don't do cash for ass, you feel me?"

She gave him that throaty laugh again and tossed her hair. "No cash, just...anonymity."

"You got a mob husband or something?"

"Or...something."

"You're not married, are you?"

Again, with the laugh. "No. I just have a reputation that doesn't lead to having a late night rendezvous with a stranger."

He nodded. "Fine. No names. I'm cool with that."

"Really?"

He gave her a soft smile and put his hands on her hips, pulling her to him. "Sugar, sweetheart, cupcake, I can call you all the names you want."

"Sounds like a plan to me," she whispered only a moment before her tongue snaked into his ear. "Let's get naked."

She gave him a push and he landed on the bed, propped up on his elbows. His mouth ran dry as she pulled her shirt over her head, revealing those glorious tits to him. "Fuck, you're beautiful," he murmured as she straddled his waist.

She smirked and bent down to take his mouth, and take she did. She definitely knew what she was doing, and she did things with that mouth that made him question his sanity. This was just what he needed.

She unbuttoned his shirt at lightening speed and bit as his chest as she moved down, down down, "HOLY FUCK!" he cried as she deep-throated him. When did she unfasten his pants?! He felt her hand on his and she moved it to her head. His eyebrow popped. Dirty girl likes it rough. Okay. I can work with that...

He fucked her mouth and she took him like a champ as he continued thrusting. She nipped, sucked, tongued, he'd never had his cock and balls worshiped quite as thoroughly as she did. Finally, when he was almost at his breaking point, she pulled away.

His eyes rolled back in his head as he fell to his back. "Fuck. That was...damn. You're good."

She smirked and stood, stripping naked for him. He sat up and slid his pants the rest of the way down, toed off his boots and socks, threw his shirt off, and crooked a finger for her.

She slithered on top of him and he rolled them. "My turn," he commanded as he moved down, down, down, her body.

He returned the favor twice over, enjoying her tart flavor on his tongue as she came before he reached into the pocket of his discarded jeans for the condom. "You ready, sweetheart?"

She bit her lip and nodded before she turned over and put her ass in the air. His eyebrow went up, but he shrugged and went with it. Chick knew what she wanted. He could respect that.

He kissed her shoulders as he slid the condom on and kissed down her spine. She let out a moan of pleasure as he bit both globes of her ass before he kissed back up to her neck. "Do you want it rough? I don't usually do that, but you seem to..."

"Yes!" she cried. "Fuck me hard and leave me bruised."

He blinked. He was no stranger to sex, but usually it was the other way around. He was the one wearing the bruises (not that he was complaining) but still... "If you're sure..."

Instead of answering, she pushed back, impaling her self on his cock. "Fuck," he hissed as he grabbed her hips. He gave her what she wanted, the fuck of her life as he pounded into her while she cursed and bucked. It was one hell of a wild ass ride.

When it was finally over, the long day of hunting, Jordan, the booze, and the excellent sex lulled him to sleep almost immediately, but not before he saw a self-satisfied smirk on her face.

The next morning, Dean woke alone, which wasn't quite a surprise. He'd gotten used to doing the leaving, but about a third of the time, it was the chick that left. Such was life. He stood and went to find his clothes, which weren't by his side of the bed. She cleans, too? Wow.

He searched the bathroom, the drawers, under the bed, nothing. He was as naked as the day he was born. And with his clothes... "Son of a bitch!" he yelled. She stole his wallet, his cell phone, everything. "FUCK!"

He looked out the window at the just breaking dawn and sighed. Her car was, naturally, gone. Luckily for him, he was in the same motel as Sammy. So, with a hit to his pride, he wrapped the sheet around his waist and walked barefoot a few doors down and pounded on the door.

Sam opened it wide eyed, gun in his hand. Dean just shot him a look. "Don't fucking ask."

Sam's lip quirked. "Please tell me you at least got laid."

He gave a self depreciating chuckle. "Yeah, I did."

"She take everything?"

"Yes. Damn it. My phone. My fucking phone. I just beat that next level of Candy Crush, too."

"Sucks to be you," Sam chortled as he opened the door wide to allow his brother in.

"Fuck you, Sam. Fuck you." He knew he'd never live this one down. Man, some days, I fucking hate my life...