Ben Loves a Challenge

"Didn't I tell you not to call me?" Dean asked from his rolled down window.

Ben smiled, stepping up to the curb, feeling somewhat back to normal, and drunk, but not terribly drunk. "Did you?"

"Oh, now you're cocky, cause you're drunk. It's too early for your dickhead friends to have left you," Dean said.

He shrugged and pulled the door handle, but the door was locked. "I'm bored."

"You called me because you're bored, surrounded by strippers and booze?" Dean asked. "I'm not here to be your song and dance man, Ben."

"You came," Ben pointed out. He reached into the car and fumbled with the controls on the door in the dark until he heard the doors unlock. Dean crossed his arms as Ben sat down and buckled up.

"Not because..." Dean didn't continue.

"Let's do something," Ben declared.

"Why'd I come?" Dean lamented.

"Cause you like me," he answered. His drunken confidence instantly deflated. "You like me, right?"

"Ben," Dean said with a sigh. "Shit, your asshole friend is looking for you. What'll you tell him?"

"I told him I got an Uber. Be my Uber, Dean, and let's go. I can pay you," Ben said.

Dean pursed his lips, then put his car into drive. Ben tried hard to avoid being seen, but Justin had just been coming outside to smoke. He didn't even look around. Ben felt a little jilted, but it faded almost instantly. Dean had come to get him!

"I'm not taking your money," Dean grumbled.

"Let's do something fun!"

"Nope," Dean said. "You need to sober up. Where's your house?"

Ben crossed his arms over his chest, wrinkling his suit jacket, but he didn't care. "No. I wanna go to your house."

Dean drove on, watching Ben from the corner of his eyes. "You want to enter the layer of the beast?"

Ben snorted a laugh. "Is that what you call your apartment?"

Dean shook his head slightly. "No. You're straight, and I'm gay, and I know what you look like naked. That should bother you. It did bother you."

Ben nodded, feeling wiser than sober. "It did, but now it doesn't. I like your apartment. It's nice. It smells nice, like you smell nice."

Dean's eyes were locked on the street now. "No."

"No?"

"You can't do this," Dean complained. "I'm gay, Ben. You know I'm gay. I don't get involved with straight guys, and definitely not straight guys who wanna feel better about themselves by having a gay friend. I won't be your token gay friend, yea?"

His chest was tight when he spoke again. "I don't wanna be token friends," he complained. "I wanna be friend-friends. Non-token friends."

Dean sighed, leaning his head back on the headrest as he stopped at a red light. "DeLuca, you're exhausting."

"Did you like it?" Ben asked, his alcohol courage making his words leak from his mouth.

"Did I like what?" Dean asked.

Silence filled the space between them for several minutes. Ben recognized the neighborhood, and despite his argument, Dean had taken him back to his apartment. Dean sighed as he turned off his car, then turned to him.

"If you come upstairs, you will be giving me the wrong idea. What's your address? I'm taking you home."

He didn't want to go home. He wanted to know what it felt like to have Dean's heat next to him, wanted Dean's scent to surround him again. He wanted to kiss Dean for real, and the thought had him erotically charged, and ashamed. "You did."

"I did what, Ben?" Dean sighed.

"You took me home," he said, smiling to hide his nervousness.

"Ben, you know, what are you doing? What do you want from me?"

Ben reached out, and something deep inside pushed him to keep going, despite the think-too-much part of his brain fighting against him. Dean flinched when he touched his hand. He screwed up his alcohol-burning courage and opened his mouth.

"Let's hang out. Do you have any booze?" It wasn't what he wanted to say. He didn't want to say what he wanted to say, didn't know how to say it, or even what he felt.

"Ben!" Dean moaned.

"C'mon, Dean!" Ben exclaimed. "Let's be real friends. No tokens."

Dean looked down at Ben's hand, then at his face. "If you come inside, I might kiss you, you idiot. You're exactly my type. Let me take you home, Ben. You don't want that, yea?"

The thought that he was Dean's type pushed him past logical reasoning. His member ached, straining against the stiffness of his jeans. "What if I did?"

Dean swallowed hard. "You don't. You're drunk."

"So what if I'm drunk?"

"You'll regret it, like last time but worse," Dean said.

"I won't," he insisted, shifting to relieve the pressure against his loins. Dean glanced down, then quickly turned to look out his side window. "I won't, Dean. I... Since you..."

"No, Ben. I don't mess with straight guys anymore. Especially not curious straight guys."

"I won't... Can't it just be-"

"No. It can't. You know about Parker. I can't."

"Dean." Ben shifted, moving his hand to Dean's shoulder. Dean flinched, staring straight out the windshield. "Dean, look at me."

"Ben, you're drunk. Stop this. Let's go, we can go upstairs, and you can take my bed again. Come on, yea?" Dean said, accepting that Ben wasn't going to give him his address.

"Okay," he said. Dean lifted his hand off of his shoulder, then got out of the car.

He heard Dean mutter under his breath. "You're killing me."

He was steadier than he'd been before Dean had picked him up. He followed Dean to a dimly lit stairwell just on the inside of the glass security door.. "Come on," Dean said, motioning for him to go first.

"You have an elevator," Ben remarked, but started up the steps anyway.

"Healthier," Dean said, following a fair distance behind him.

"You trying to tire me out?" he asked. "Sober me up?

"Maybe," Dean replied from behind him. "Both maybe."

He wanted to ask if Dean liked his ass, but he didn't. He also wanted to look back, but he didn't do that either, but not because of Dean. He worried it would make him feel sick. He was slightly winded by the first flight, and had to slow down on the second flight. Dean pushed him with a hand on the small of his back up the third flight, and he wouldn't say it aloud, but he intentionally slowed down just to keep Dean's hand there longer.

He felt mostly sober when they reached Dean's door. Despite the relative sobriety, his resolve grew stronger. He wanted to know what that kiss would've felt like, when Dean had smooshed his face the other day.

"Welcome," Dean said, as he slipped the key into the lock and pushed the door open. He flicked on the light, and Ben saw he'd interrupted some game that Dean had been playing, the screen still on, showing a pause screen with tons of options.

"Hey, Dean?"

Dean sighed, hanging his keys and taking off his hoodie. "'I'm an idiot. What Ben?"

"Thanks, for coming to get me, even though you said you wouldn't."

"Yes, I'm an idiot," Dean confirmed.

Ben turned, stepping closer to Dean. Dean backed up and Ben advanced until Dean's back was against the door. "Stop," Dean begged. "Please. You're sexy, Ben, and I'm weak. Stop playing with me."

He leaned in, pressing their bodies together. Dean was trembling. "I'm not playing."

"Yes, you are," Dean said, turning away. "I can't do this."

"I'm not," he insisted, catching Dean's face between his palms. "Did you like it?"

"You asked that already," Dean complained, unable to turn away from him now. "Did I like what?"

"My body."

Dean trembled again. "Stop tormenting me! I already told you you're my type. Stop, Ben, cause this is worse than your reaction last time. Don't mess with me like this."

Ben leaned up to kiss Dean, but Dean caught his face again, holding his jaw with one hand. "Dean," he whined.

"You're playing with fire," Dean growled.

Ben could feel something hard against his belly, and his loins clenched excitedly. "You can take pictures of me, and you can do whatever you want. Spread them around the office, I don't care. I don't care, really."

"Ben..." Dean moaned. He hesitated, conflicted, his eyes studying Ben's face.

"Dean?" he asked, teasing Dean from before.

"Fine. If you can kiss me, that is. Can you kiss me, Ben? Can a straight, formerly homophobic guy like you actually kiss-"

Ben pushed past Dean's hand and caught his lips, then pulled him down so he could kiss him properly. His heart was beating a million miles a minute, and Dean was stiff as a board, but he kissed him, forcing his way into Dean's mouth. After a few one sided kisses he pulled away, looking for Dean's response.

"Ben," Dean moaned softly. "You're killing me."

"I did it, Dean," he said, feeling light, so aroused it was growing painful. "Let me stay? Kiss me back."

"You're an idiot, Ben DeLuca, but I'm an even bigger one," Dean sighed. He leaned down and kissed him, first just firm press of his lips to Bens, then deeper when Ben opened to him. Dean's hand wrapped around the back of his head, pulling him closer, and then they were kissing for real, Dean moaning between breaths.

After a few breathless moments Dean danced them to the couch, then pushed Ben down onto the cushions. Ben's lips felt puffy as he struggled to catch his breath. Dean standing above him, looking down on him like that made his cock jump. "You're really handsome," he said.

Dean's cheeks grew those cute, rosy spots that he liked. "You're an idiot," he said again. He fell to his knees on the floor, his eyes never leaving Ben's.

"Can we kiss some more?" he asked.

"It's not fair. You're so freaking hot," Dean growled. Ben sat up and caught Dean's head again, kissing him with the pent up frustration of the last six months of pining after a woman who didn't love him. After a few seconds of kissing he realized he didn't love Laura anymore, either. His chest filled with a yearning for Dean like he'd never felt before.

He let that yearning drive his kisses, move his hands. He wanted to claim Dean, but more than that, he wanted to be claimed by Dean. He knew it would confuse him later, but the answer seemed so clear to him now. Dean tasted good, and he kissed him more, tasted him more as he probed deeper.

Dean broke away, his pupils dilated and his hair disheveled. Ben realized it was his fault, the feeling of Dean's soft hair still between his fingers. "Ben, last chance," he said. Dean's words were firm, but his eyes were begging him to stay.

"I'm not leaving," Ben declared, reaching out for Dean again.

Dean dodged his reach, then pushed Ben onto his back. Confused, he tried to sit up, but Dean pushed him down again, then easily broke into his pants. Breathing heavily, Dean pulled out his manhood, his touch sending enough electricity to his brain to practically reset it. He lifted his hips to allow Dean better access.

"Close your eyes and imagine someone else," Dean said, looking into Ben's eyes.

He shook his head, the sight of Dean holding his cock burning into his brain, of Dean's face so close to his member. "It's one thing to kiss. This... It's another level. You'll regret it, and I want you to enjoy it."

"Dean, I wanna watch," he said.

Dean squirmed. Ben saw the exact second he gave up, and then Dean's lips were on the tip of his cock. He was squirming now, unable to keep still as Dean's tongue flicked the precum from his slit. He caught Dean's eyes. Dean blushed hard, then turned his head to take Ben's aching manhood into his mouth.

He didn't know if it was in his head or not, but it felt completely different from a woman's blowjob. Dean sucked hard, sensitizing every centimeter of his cock inside Dean's sexy mouth. He ran his fingers through Dean's soft hair, allowing the pleasure to fill his whole body.

He moaned Dean's name and Dean flinched, then sucked him deeper. The hint of teeth was thrilling, and too soon he was ready to burst. He used his hands in Dean's hair to pull him back. Dean looked up at him, afraid. "Too close," he moaned as Dean squeezed down on his cock. "Gonna cum."

Dean's fear dissipated. "Then cum."

"Not, don't wanna, in your mouth," he said, focusing on Dean to bring himself back from the brink.

"You don't want to cum in my mouth?" Dean asked, trailing his finger around the sensitive frenulum. Ben shivered.

"Not if you don't like it," Ben found enough focus to say before Dean teased him even more. He couldn't be still, then Dean smiled and ruined chance of him calming down.

"Don't worry about me," Dean said, dipping his head back down to Ben's cock. He licked from root to tip, and it took everything he had not to thrust his hips upwards to increase the pressure. "Just cum." Dean looked up at him, the lust in his eyes a physical force.

Dean's lips closed around his cock again, sliding halfway down before slipping back up. Dean did it again, slowly, going a little deeper on each following descent. Ben only lasted four rounds of this before he was cumming so hard that he could feel it hit the back of Dean's throat. Dean moaned, speeding up, bringing more and more waves of orgasm to him, forcing his crescendo higher and higher.

"Dean," he moaned, his hips moving on their own. "God, Dean. Don't stop."

Dean didn't stop, he kept bobbing until Ben pushed him away, soft and sated. "Thank you, Ben," Dean whispered, then stood up and walked away.

His energy was sapped, he wasn't fully back online yet. "Dean?"

"Go to sleep, Ben," Dean said. "This was just a weird dream."

Ben fell off the couch, his soft dick still hanging out of his pants like a lazy elephant's trunk. "Dean, stop, please," he said, unable to make his pants come up while standing up. He failed at both and fell to his knees.

Dean hesitated, his back to him. "How many lines do you wanna cross tonight, Ben? You're gonna find one that you can't come back from, if you're not careful."

"You didn't cum. I saw you were hard, I could see your tent. I can't, we aren't even, I need to-"

Dean laughed, but it sounded scared. "Since when was this about being even?"

"Dean," he whined.

Dean was too still. Ben struggled with his pants, finally tucking himself back inside, then stood up. "Go to bed, you can sleep in my bed," Dean said, his voice hard.

"You come with me, then," he said.

"How are you so confident? You aren't even drunk anymore!"

"I've never felt like this, but Dean, I like it," he said. "I don't understand, but-"

"I can't do this with a straight guy, Ben, and you're a straight guy. I can't do one night stands, either, so don't even ask. I got you off, now go to bed. Forget this ever happened."

"If I did, this would be a one night stand!" Ben could see Dean shaking. "No. I don't wanna forget. I wanna do more with you. I dreamt about you, I think about you, wondered what it would feel like to kiss you. To feel you against my body. Give me a chance, Dean."

"You don't even know me," Dean said, his voice wavering.

"I want to," he said.

"You don't even know if you wanna know me," Dean said with a cold laugh. "Why are you doing this? Is this punishment? Is it some mean game you're playing with your dumb-ass friends?"

"I told you to take a picture of me, naked or doing something gay, and you could use it as blackmail. Maybe I shoulda called it insurance. You can use it against me, if I hurt you, or something. I'm willing to, no, I want you to. That's how serious I am."

"What if I posted it right now, to Instagram or something?"

Ben shrugged, but Dean still wasn't looking at him. "If you wanted to," he said.

Dean turned around quickly. "What is wrong with you?"

"I dunno," he admitted. "Why would this mean there's something wrong with me?"

"Why are you doing this?" Dean's hands were tight fists, the skin white around his knuckles. Ben wanted to kiss each white knuckle.

"I dunno," he said again. "But, it feels right."

"Is that how you base all the decisions in your life? If something feels right?" Dean spun away from him again.

He nodded. "Yeah, kinda. Dean, turn around and talk to me, please?"

Dean shook his head. "No."

He sighed, and pushed himself up off the floor. Dean jumped forward when he tried to wrap his arms around him from behind. "Dean. Give me a chance."

"Ben, I didn't sleep with Parker. We had drinks. He confessed that he was bi-curious, over text messages. Then his wife found out, and destroyed him. Your friends will destroy you, no matter how curious you are, or how much I want..."

"What do you want?" Ben asked.

"Why do you care?"

He stepped up to Dean again and slipped his arms through, forcing Dean against him. Dean struggled, but he held him tight. "I can't stop thinking about you. I dunno why. I wanna get to know you."

"I'm not here to satisfy your bi-curiousity," Dean snapped, his body pure tension. "See where it got Parker?"

"I'm not Parker."

"You're worse."

"Please, Dean? Give me a chance. I'll do anything. Give me a week, and if you tell me to go to hell at the end of it, if you post lewd pictures of me on the internet, I'll leave you alone."

Dean didn't say anything. Ben leaned in closer, pressing himself against Dean's back, resting his head on his shoulder. They both nearly toppled to the ground when Dean relaxed, but Ben caught him and absorbed his weight.

"You said anything," Dean said after a moment.

"Yeah," Ben said. "I mean, I'm not gonna kill myself or throw myself off a building, but shy of that, sure."

Dean pushed his hands off, then turned around, his face a cold mask. "Fine. I'll give you a week to change my mind, and if you don't, I'll ruin you. Understood?"

Ben's smile was huge. He nodded, holding his hands against his sides. "Yes sir."

Dean watched him carefully. "Strip," he commanded after a contemplative moment.

Ben didn't understand the command at first. Dean frowned, and he jumped into motion, removing the recently readjusted jeans first. They slid to the floor with a gentle swooshing sound, taking his underwear with them. As he pulled his feet free he removed his shoes and socks, leaving everything in a big heaping pile. His jacket slid from his shoulders and he worked to unbutton his shirt, but now his nerves were getting to him and his fingers fumbled.

He looked up excitedly, but the look on Dean's face was neutral as he watched. The last two buttons were the hardest, he was shaking too much to keep his fingers steady. He threw it in the pile, too, then stood at attention for Dean's inspection, hands behind his back.

Dean's eyes traveled the length of his body, and Ben wished it was his hands. He knew he should question this newfound obsession with Dean, should be thinking about what it meant, the things he was doing, but he found he didn't want to. Whatever this was, with Dean, was exciting.

"You're already half-hard again? You're such a freak," Dean chastised, his voice firm. The tone was the exact same as from when he imagined Dean spanking him the other, and he felt his cock firm faster. "Are you a freak, Ben? Do you like me being mean?"

He swallowed hard, then nodded his head, looking down to his feet.

Dean's finger slipped under his chin and brought his head back up. "I didn't hear you, Ben. Do you like me being mean to you?"

It was his turn to tremble. A shiver rolled through his body. Dean pulled his hand back, worry on his face. Ben didn't like it, he liked when Dean was firm and in charge. "Yes, sir," he whispered.

"I like that, you calling me 'sir'," Dean announced. "I like it a lot. Hmm... Let's see... Ben, follow me."

"Yes, sir," he said, his throat tight, his cock hard. Dean didn't wait to see if he followed directions, he strode confidently to his room. Ben followed, careful to keep enough distance between them so that he didn't bump into Dean if he stopped suddenly.

Dean's room smelled good, better than he remembered. The light was off, and Dean made no move to change that as he shut the door behind them. "On your hands and knees, Ben."