Ben Loves a Challenge

"God, Ben, I'm doing this all outta order. I'm sorry. I mess everything up." Dean paced up and down his living room as Ben removed his coat and shoes.

"Stop, Dean. Nothing's wrong. Why're you saying that?" Ben asked, feeling more than nervous.

"I shouldn't be collaring you like this. There should be, we should've been dating for a while. I just..."

Ben sighed. "Dean, I asked for this, and you're humoring me."

Dean barked out a harsh laugh. "You don't even understand what this means, not really. We should've talked about it, should've worked it out, but I rushed into it because..." He deflated, then threw himself into the recliner next to the couch.

Ben's eyes rolled up. Dean was being dramatic. "Dean, nothing's out of order."

"We should be at dinner right now. I should be pouring you a nice red wine, we should be eating. Getting to know each other."

Ben stalked forward and dropped to his knees between Dean's legs in front of the recliner. He looked up, Dean's pain hurting his heart. "Dean, I love you. Collar me. I wanna wear your collar. I wanna... um... We don't have to work tomorrow. I wanted to, ah, spend the night. If you don't mind..."

Dean swallowed hard. "You wanna spend the night?"

He nodded. "Is that okay?"

Dean nodded. "We can do whatever you want."

He exhaled. "Dean, please. Stop this. I wanna see the collar you chose for me. Show me? Please?"

Dean looked at him, vulnerable and afraid. "If you stay the night, you'll give me the wrong idea. If you let me collar you now, you'll give me the wrong idea."

"Dean, it's not the wrong idea. I've been waiting all week. I want..." He couldn't say it, it was too embarrassing.

"I wanna make you mine, Ben." It was a statement, a fact, but the way he said it made it seem like he was implying that what he wanted was bad. "If you stay, I'll wanna make you mine."

Ben leaned closer, pushing Dean's legs apart. "I want that, too."

Dean watched him for almost too long, then reached into his pocket. "You'll let me collar you?"

"I want you to collar me," he agreed. "No one at work will know what it means but us, and I totally wanna feel like that. Make me yours, Dean."

Dean's hands were shaking as he pulled out the black metal collar. It had similar metal working, Ben noticed, but the black was shiny and almost iridescent. Ben leaned closer. "I want you so much," Dean whispered, his hands trembling.

Ben took his hands and pulled them closer to inspect the collar when Dean froze up. "It's awesome. Do it, Dean. We can spend all night making me yours. All weekend, if you wanted."

"I'm afraid you won't like being fucked, Ben. It scares me a lot."

"Stop stalling. Even if I don't like anal, I've enjoyed everything else we've done so far. Is no anal sex a deal breaker, in the event that I don't enjoy it?"

Dean shook his head quickly. "No, not at all. I mean, of course not."

"Then stop stalling and collar me, Dean. Then, you need to punish me for coming on the floor when you told me not to." Ben leaned in, then went up on his knees and planted a kiss on Dean's lips before he could say anything else.

Dean snorted, then pulled back, a soft smile on his face. "You're killing me, DeLuca."

Ben smiled, too. "Make me yours, Sir. Please?"

Dean's hands shook as he pulled the collar out. The metal was warm as it wrapped around his neck, and Dean spun it around so that the ends were under his chin as he clasped it. His fingers lingered a little longer, then brushed Ben's adam's apple before he retreated, sitting back to admire the collar.

"It looks so good on you," Dean whispered. His hand cupped Ben's cheek, and then they were kissing. Dean tasted like copper, and Ben wondered if he'd bitten the inside of his cheek until he bled. "Thank you, Ben. So much."

He kissed Dean back. "Thank you, Sir," he said. "Dean. I love you."

Dean leaned his forehead on Ben's. "I love you, too. This's too good to be true."

"Sorry, but you're a Disney princess now. Suck it up."

Dean pulled back to look him in the eye, looking confused, then barked out a laugh. "Sure, sure. Don't you wanna go see it?"

"Absolutely," he said, jumping to his feet. He ran to the bathroom, his fingers tracing the collar. It sat comfortably at the base of his neck, with a quarter-sized hoop just below the hollow of his throat. It made him shiver in pleasure as he traced it with his finger. He was leaning in to inspect the collar closer when Dean came into the bathroom behind him.

"Do you..."

"I love it. How do you take it off?"

Dean bit his lip. "You don't."

"Oh, I know. I was wondering how it works. I wouldn't dream of taking it off."

Dean was worrying his lip now. He reached into his pocket and fished around, then came out with a small black bar. "I press this into this black piece next to the hoop, like this," he said, leaning into Ben's back. Dean watched himself in the mirror as he placed the bar into the small hole in the connection piece. It fell apart easily and Dean caught it.

"How'd you know how to do that?" he asked, jealousy blooming in his chest.

Dean kissed the side of his cheek, still watching them in the mirror. "Sheila taught me. I've always wanted..." He looked down. "I've always wanted to do this to someone. Someone special."

Ben's butterflies danced in his stomach. He reached back and pulled Dean against his body. "Thank you."

Dean reattached the collar around his neck, then kissed his cheek. "Do you... Do you like it?"

"Have you been listening? It's awesome. I really, really like it."

It tickled as Dean traced the metal around his neck with his lips, eyes locked on Ben's in the mirror. "You're supposed to be in trouble, aren't you?"

It amazed him how quickly Dean could switch from normal Dean to Dom Dean. "Yes, Sir," he said, turning away from his reflection.

Dean stepped back, then pulled him by his hands from the bathroom and back into his bedroom. "I know I asked you to dress up, but take it all off. Now."

Ben swallowed. "Yes, Sir," he said, his throat raw. He took his tie off and put it on the dresser, then started unbuttoning his shirt, Dean closely supervising his increasing exposure.

"I'm going to fuck you tonight. Do you understand?"

He swallowed hard and shrugged off his shirt, folding it half-assed before he put it on Dean's dresser, too. "Yes, Sir."

"I'm going to slip my cock inside your ass and thrust into you until I come. Do you want that?"

His pants slid down his legs, and he pushed his underwear to follow. "Yes, Sir," he whispered.

"I'm sorry, bitch, I didn't hear you, yea?"

"Yes, Sir. I want you to," he cleared his throat here as a squeak came out. "I want you to fuck me. I want you to... make me yours." He swallowed hard again, then took his socks off. He stood back up, dressed only in Dean's collar. It was so freaking sexy he could barely stand it.

Dean moaned appreciatively. "Shit, Ben. You're wearing my collar."

"Do you like it, Sir?" he asked, barely audible, his throat tight with lust, embarrassment, and nerves.

"It's perfect. You look so hot right now," Dean breathed out. He stalked over to Ben, then fell to his knees before him. "You don't even know."

Ben's cock was in Dean's mouth before he could think of a response. "Mmm," he moaned out, losing the ability to form words as Dean's lips sealed around his shaft and his tongue pressed against his slit.

Ben watched Dean suck him down, then release him to lavish kisses up and down his length. Dean's glasses were super hot, totally hitting some buttons he'd already had preprogrammed. He'd been into nerdy girls with glasses, and now he was into Dean with glasses, too.

"I like..." he panted out breathlessly when Dean pulled back into kisses again.

Dean gripped his cock hard. "You like? What do you like?"

"You in glasses," he said, feeling light-headed from his growing desire. "It feels intimate, and it's always been a turn-on for me."

Dean smirked. "You like nerds?"

Ben snorted. "What can I say, I'm attracted to intelligence."

Dean gripped harder. "Glasses don't mean someone is intelligent. They'll give them to anyone, yea?"

Ben nodded. "I didn't know you wore glasses until tonight. Like I said, attracted to intelligence."

Dean snorted out a laugh. "Sure, sure." He plunged his head down Ben's shaft again, and rose up off it just as fast. "Ben?"

Suddenly Dean looked apprehensive. "Dean, it's okay. I'm good."

He shook his head. "Are you sure you wanna... You sure you... I wanna have sex with you so much, but I'm so afraid you'll hate it. That you'll realize you made a mistake."

Ben smiled softly, cupping Dean's face between his hands. "I'd be lying if I said I wasn't scared. I am. It's exciting, though. It's good scared. It's planning the future scary, and pain scary, and honestly? I'm worried that I won't be good at it and I'll disappoint you."

"You won't," Dean insisted.

Ben shrugged. "We won't know until we try. What should I do? To get ready?"

"No regrets?" Dean asked, looking up at him with so much vulnerability that it hurt his heart.

He shook his head. "None so far. I want you to punish me, get me ready, I wanna do this. With you. Everything we've done so far has been awesome. I'm enjoying everything, I promise that's not a lie. Dean, I won't lie to you, not ever, I swear it. I fucked up my last relationship cause I was bad at communicating, which made it seem like I was lying.

"Oh, and also cause I was selfish, and an asshole. I hope I'm better in all those categories. I wanna be better, for you. To be worthy of you. Aisha told me today that everyone at work though I was an asshat because I hung out with Hugh. She called it 'Hugh's Posse'. She's right. I was."

Dean's face soured at the mention of Aisha. "I don't know if I like her paying so much attention to you all of a sudden."

Ben smiled. "You being all possessive's hot. She's a dominatrix, invited us to come check out the dungeon she works at." Dean's face darkened. "Not like that. Cause she thinks we're into BDSM."

"Maybe don't talk about her now, yea?"

He sniffed out a laugh. "You're right. I'm just saying, I was not a great person when I was in Hugh's Posse. Is that really what everyone called us?"

Dean bit his lip, then nodded. "Kinda."

"Whatever. I'm not anymore. You made me wanna be better. I wanna be the me I am now, with you."

Dean's eyes looked a little watery and he turned away. "You're really sentimental, aren't you?"

"Is that bad?"

Dean shook his head. "I'm killing the mood, aren't I?"

He shook his head. "No, no," he said. There was no way he was going to let Dean start getting down on himself, even if he was right. "I'm good. This's good. What do we need to do to get me ready for you?" He shivered a tiny bit, both aroused and afraid.

Dean's arms wrapped around his ass, pressing his face into his belly. Ben threaded his fingers through his silky hair. "I bought some different sized plugs, to stretch you out slowly."

Just as Dean pulled away, Ben's stomach betrayed him by gurgling loudly. "Sorry," he said, looking down at his half-mast manhood.

"I really am doing this all wrong. Dinner, of course you're hungry. We basically skipped lunch today. Okay," he said, pushing himself up from the ground. "Let's do this."

"Dean?" he asked as Dean stepped behind him. He didn't turn, unsure if they were playing or not.

"Ben, we need to relax you, get you ready so it doesn't hurt. I thought we'd use plugs," he said, digging through the bottom dresser drawer. He pulled out a hard, clear plastic package with three black, tulip shaped bulbs with wide flat bases arranged from small to large. "These."

Ben swallowed hard. "Plugs?"

"Butt plugs," Dean said, prying open the package. It came open easier than it looked like it would. "We'll start with this small one first." He picked it up and held it out for Ben to appraise.

Ben took it, his hand shaking a little. "This goes inside me?"

Dean flushed. "Yeah. Helps you get used to the size, then we'll go up to the next one, once you're comfortable. Are you sure, I mean, we don't have to have sex, we can just-"

"Don't you wanna?" Ben asked, turning the plug over in his hand. It seemed small enough, but he had no idea how these things worked. Well, he had the general idea, but not of the size to pain ratio of it.

"Of course, but I wanna make sure you're, I mean, you, it's, I don't want, you know..."

Ben handed the plug back to Dean. "I wanna have sex with you, so help me get ready. I don't know how to use this."

It was Dean's turn to swallow hard. He took the plug back and pulled something else from the bottom drawer, a clear bottle with a pump top. "Get on my bed," he directed, though it wasn't the same tone he used when they played. "Put your head down on the bed and your ass in the air. Good," he said when Ben followed his directions. His ass was up in the air and his knees spread so that his cheeks spread wide enough to make him feel the most exposed he'd ever felt.

Dean fiddled with stuff behind him. "Dean?"

"Ben? Are you okay? Did you change your mind?"

"No, I'm good. Just, can you explain what you're doing? I'm super nervous," he asked.

"Oh. Yeah. Sure. Yeah. So, I'm putting a lot of lube on the plug, you don't get wet like a woman would, so we need to make sure it's nice and wet back here." Dean pressed one finger to Ben's hole.

His whole body shuddered and Dean pulled away. "Please don't stop," he begged.

"Sorry. Let me know if I hurt you, please? Don't try to act all tough, this doesn't have to hurt, yea?"

He forced himself to take deep, even breaths. "Okay."

"Okay," Dean said, pressing his finger against Ben's hole again. It was slippery, and he gasped when it pressed its way inside of him. "Okay. I'm gonna put some lube in here, too." He wiggled his finger around. "You okay?"

Ben nodded, all of his attention locked onto that finger knuckle deep into his ass. "Yah," he gasped out. It was a weird feeling, but also naughty. It was good. "Isss good."

Dean froze up, then circled his finger just on the inside of the tight ring of muscles. "Relax, Ben."

"Yah," he agreed, forcing his ass to unclench.

Dean's finger slipped a little deeper. "Good. You're doing good." He wiggled it some more, then sank it even deeper, not stopping until the rest of his fingers were against Ben's crack. He curled his finger down and pressed against something inside that made Ben's toes curl up. "That's your prostate," Dean informed him. "This right here is why getting fucked as a man feels good. You feel this?" He punctuated his question with another firm caress.

"Yah. Feels good," he said, face hot from the shame of his position, and being fingered.

Dean rewarded him with another caress. "I'm glad," he breathed out, barely a whisper. "Okay. I'm gonna put the plug in now," he said in his normal tone. He pulled his finger from Ben's ass and he suddenly had a strange feeling of emptiness that he didn't like. Before he could say anything the slippery tip of the plug danced over his hole.

"Dean," he gasped, his body trembling again.

"I won't hurt you," Dean said, placing his palm firmly on the small of Ben's back. It was intensely soothing. "Relax. I'll go slow. If you wanna stop, just say it and we will. Like, the colors, remember when we talked about the colors?"

"Green," Ben moaned out, pressing his ass into the lubed-up plug.

Dean's hand pressed firmly against his back before the tip of the plug began to press into his anus. It slowly pushed its way inside, stretching him a tiny bit at a time. Even so, Ben realized he was panting, and he flinched as a sharp pain had him clenching reflexively. "Sorry, sorry," he moaned.

"Shh," Dean soothed, pulling the plug back a little. "Let me know when it hurts. This takes time, so relax. If you aren't enjoying it, tell me." He pushed the plug forward again, just to the point before the pain started, then backed it off again. Next he swirled it around his hole, still pushing it in slightly.

"That's nice," Ben admitted. "It's bigger than I realized," he said with a nervous chuckle.

Dean didn't say anything, just rocked the plug back and forth over his opening, pushing and receding in a soothing rhythm. He jumped when Dean's lips touched his left asscheek, the relaxed again when Dean kissed him there. As if encouraged, Dean began peppering his ass with kisses and small nips.

"You really like biting me, don't-" he was cut off as the plug sank deep, then seemed to pull itself inside him the rest of the way. "Oh, god."

"Fuck, Ben. You are so goddamn sexy. I'm not gonna make it, I wanna cum so bad. I wanna jerk off and cum right on the plug in your ass," Dean said between kisses and nips. "You still need stretched more. I don't want it to hurt."

"We have all weekend," he reminded. "Cum if you want."

Dean's hand on his back tensed, then disappeared. He turned to look, worried Dean was fretting about it. Cock in hand, Dean was staring at his ass with a look of determination. "I wanna take my time with you, but I want you so bad."

"Cum on the plug. I want you to. I'll beg you, or you can do it as punishment, or just because you wanna. But, don't hold back. Not now, let's enjoy ourselves."

Dean's hand began jerking, hard and fast. The other hand returned to the small of his back. The sound of his masturbating was too sexy, he wanted to touch himself. "Ben," Dean moaned. "I love you so much."

"Can I touch myself?" he asked.

"I want you to cum," Dean grunted. The noises he made grew steadily louder as his hand moved faster. "I'm so close."

"Sir, are you gonna cum on the plug in my ass?" Ben asked, shifting up on his hands and knees to grab his cock before he dropped back down to one shoulder.

"Fuck yes," Dean moaned. "I'm gonna paint your ass with my cum."

"Please," Ben begged, his hand moving awkwardly at that angle. Still, Dean's dirty talk was making him so hot, along with the full pressure of the plug in his ass. "Cum on my ass, Sir."

Dean's fingers clenched up on his back, then Dean's hips pressed into Ben's ass. Dean's cock rubbed against him in time to his jerking. He shuddered before Ben felt the first warm rope of cum land between his asscrack. His hand sped up, he was so close, too. He wanted to cum before Dean was finished, wanted to cum as Dean coated him, but he couldn't.

He whined, his arm still moving, but he couldn't find the right angle, couldn't get enough friction to bring him. Dean flipped him over roughly, then dropped to the floor between his legs again, breathing hard from his own orgasm.

"Dean!" he exclaimed. Dean sucked his cock inside and took him deep, deeper than he'd ever been able to do. He felt a rush of jealousy that was soon dashed by a wave of pleasure pushing him closer to the crest of his orgasm. "Dammit, don't stop. Please."

Dean sucked harder and his toes curled as his hips pushed up. Cold fingers pushed his hips back to the bed and he whined, but then he came and his whining turned into pleased moans. Dean rode him the whole time, his fingers digging into Ben's hips hard to keep him from thrusting up.

Finally Dean pulled off him, but didn't say anything. Ben opened heavy eyelids and found Dean staring at him. "You okay? That was fun."

Dean nodded, then pushed Ben's back to the bed and mounted him. Ben smiled as Dean came in for a kiss. His mouth instantly filled with the taste of cum as Dean kissed him with a mouth full of it. It filled his mouth and he tried to move away by instinct alone, but Dean held his head and continued kissing him. Hard.

Dean traced his finger over Ben's adam's apple and he swallowed automatically. Dean moaned and Ben understood, but he wanted to hear it. He pushed Dean up a little. Both of them were breathing hard.