Ben Loves a Challenge

He was up before Dean the next morning, the first day of a new year. He took the opportunity to shower and clean up, then make breakfast, feeling nervous for no good reason. He peeked in when he was finished with breakfast to find a half-awake Dean petting a very lovey-dovey Tennille.

"She's such a bitch," he noted. "She's never like that with me."

Dean looked up and smiled. "You should be happy your roommate likes me, you know, if I'm maybe gonna move in."

His heart skipped a beat. "You're thinking about it?"

Dean sucked in his bottom lip. "I am. I still... I haven't decided." He reached over and grabbed his glasses off the side table and slid them on. "I'm sorry, I just need some time."

Ben nodded, hiding his disappointment by focusing on how cute bed-head and glasses Dean was. "I get it. Hey, I made breakfast, if you wanted some."

"What time is it?"

"Um, like almost one?" Ben said, looking over to where his alarm clock used to be, even though he hadn't used it in years. He pulled his phone out and confirmed. "It's five to one."

Dean nodded, then stretched his arms above his head, knocking the blanket to his lap. Dean was bare chested, and he wished the lack of clothing continued south, but he remembered Dean went to bed in pajama pants. He flushed when Dean caught him looking, but he didn't look away.

The cat stood up, clearly unhappy with the change in her petting situation, then walked away with her tail twitching. She looked at Ben and yowled, then hopped down to the floor and walked past him out the door.

"What's for breakfast? I smell... something sweet. Smells good," Dean said, sliding out of bed. He was naked! When had he taken his pajama pants off?

Holy shit, it was so hot that Dean had slept in his bed naked. He wasn't gonna change his sheets for weeks now, he was gonna wrap himself in Dean's scent the minute he left.

"Eggs and cinnamon buns," Ben said, forcing himself to avoid thinking about his naked boyfriend, which was hard to do when he couldn't stop looking. "Coffee."

Dean didn't seem to notice. He wasn't sure if he was glad for that or not. "Good, all of those things. You care if I just wear my sweats and shower after?"

Ben's eyes locked on Dean's ass as he bent over and rummaged around in his bag. "Do whatever you want," he said. "Mi casa es su casa." He blushed when he realized what he said had deeper context between them.

Dean didn't pay it any attention, or if he did, he didn't show it. He pulled sweatpants on, without underwear, then pulled a shirt over his head. Ben loved his bedhead, it was... intimate. Like, something he'd only ever get to see because Dean spent the night.

They ate breakfast and reminisced about the night before, then Dean took a shower. The day went by surprisingly fast, somehow moving from their breakfast-lunch to dinner without much effort. It was perfect, just hanging out with Dean on a lazy day off.

When the sun disappeared from the sky they ordered dinner from the Thai place down the street.

"What are you gonna do, after we eat?" Ben asked. The question had been sitting heavy in his stomach for the better part of the day.

"What'dya mean?" Dean asked, picking at his pad thai. "You like onions?"

"Yeah, I guess."

"Want mine?"

"Um, sure, if you aren't gonna eat them." Dean lifted his plate and slid the small pile of onions onto the edge of Ben's plate. "So, like, do you wanna stay the night again? Or were you gonna go home?"

"What do you want me to do?" he asked, looking up, completely serious. "I'll do whatever. I don't have any plans tomorrow."

Ben swallowed hard. "Dean, I never want you to leave. You're welcome here whenever you want. I mean, I want you to stay, of course I want you to stay."

"Okay. Then I'll stay." Ben smiled, trying to hide how happy it made him. Dean ate a few more bites. "What'dya wanna do?"

"Tonight? Um... I dunno. We could watch something, or go out, whatever you want."

"Sure, sure," Dean agreed. "Or, we could stay in. Maybe shop for some suits online?"

Ben snorted. "You aren't serious about buying me a tuxedo, are you?"

Dean looked up, a coy smile on his face. "I am one hundred percent serious. I want you to dress up in your tux again tonight, but I know we'd ruin it and I won't let you pay the stupid fee they charge. I'm buying you one, so you can either look with me, or I can measure you myself and just pick one out without you."

"I just want one that you like," he admitted. "I really don't know much about that kinda thing."

Dean nodded. "Do you mind if I measure you, then? I mean, we'd go to a tailor to have one made really nice, but I plan on using it hard so maybe a cheaper one would be better. You really don't mind if I pick one out for you? You'd wear it for me? This doesn't creep you out or anything?"

"Dean, with the way you looked at me last night, I'd wear a tux every day for you for the rest of forever."

"Stop saying things like that, Ben. You can't promise you'll feel like this forever," Dean chided, but he was smiling softly.

Ben shrugged. "I'll say what I want. And, I mean it."

Dean exhaled slowly. "I know. And I know you mean it." He sighed, then pulled his phone out. "Care if I start looking now?"

Ben shook his head, but Dean was already lost in his phone. He cleaned up the dishes then headed to his living room. Dean followed him, completely distracted, then sat down next to him on the couch as he turned the TV on and flipped through movies on Hulu. Every now and then he'd peek over and check Dean's phone to find different parts of tuxedos or suits up, or colors of ties and vests.

An hour later Dean pushed his shoulder into Ben's. "What'dya think about this one?" he asked, showing the screen of his phone to Ben.

It looked nice, but he didn't really care what it looked like as long as it made Dean happy. Ben noticed that Dean conveniently hid the price just off screen. "As long as you like it, Dean, I like it."

"Are you just messing with me?" Dean asked, pulling his phone away.

"No, no, not like that. I don't know the first thing about dressing up. You already know that D'Metrius took me since I was so clueless, and he made me try on at least fifteen different ones. So, if there's one you think would look good on me, it probably will, and that's the one I want. You don't have to buy it, I don't mind paying."

Dean sighed. "No, I'm buying my boyfriend a present. Not negotiable."

Ben bit his bottom lip, everytime Dean called him his boyfriend it felt like a little victory. "If you insist."

"I do. Okay. Do you have a cloth measuring tape, by chance?"

Ben smirked at him. "Um, no. I do not. We could go buy one, I'm pretty sure Michael's is still open for a little while."

Fifty minutes later they came back with a cloth measuring tape and some clearanced Christmas decorations. "I need to measure you, before I can order it," Dean announced after they took their shoes and coats off. "In your underwear, if you don't mind."

"Oh no, I'll have to strip down for my boyfriend, whatever will I do?" Ben fake lamented, holding his hand over his forehead dramatically.

Dean bumped him with his shoulder and laughed. "Seems like Zion and Bambi are rubbing off on you a little, you know, with the flair for the dramatic."

Ben snorted. "Don't get your hopes up, not interested in drag. No offense, of course."

Dean smiled. "That's a relief. I don't know if I could handle a third drama queen in my inner circle."

"You'll just have to make due with me being your bitch," Ben said, then flushed once it left his mouth.

Dean flushed, too, then swallowed hard. "Yeah," he said with a snort, looking shy. "Um, can I measure you?"

"Sure, you wanna do it now?"

"Um, yea. I wanna, like, yea. Please."

Dean supervised him as he undressed down to boxers, then began measuring him. He wrapped the cloth measuring tape around his neck, then measured the length of his arms, and the length from his armpit to his waist. He intentionally brushed his knuckles over Ben's nipples during two out of three of those measurements. He then moved to measure around his waist, and then his in-seam. He wasn't even trying to hide his caresses anymore, he trailed his fingers down Ben's belly to just above where his dick began, then brushed his knuckles over his package as he pushed Ben's legs slightly apart.

Once he was done with the measurements he looked up from his kneeling position. "I'll, ah, I'm thinking about maybe moving in," he announced, meeting Ben's eyes. "After my lease is up." His cheeks were rosy.

"What?" Ben said, gagging on the word a bit. "Really? What changed your mind?"

"You did," Dean admitted. "Today was really nice. It sounds stupid, but it felt like we're a real couple today. I liked it. Last night was awesome, today was awesome. Christmas and the New Year's Eve party were awesome. I mean, your cat already likes me, so, um, you know. It just, like, feels right? I dunno, I'm embracing my inner Ben right now, and I'm not used to it, so maybe cut me a break, yea?"

Ben cupped Dean's cheeks. "I'm so freaking happy, Dean. I know this is moving fast, but I feel like it was supposed to happen this way." He released Dean's face and began pacing just to burn off some of the instant energy that Dean's words filled him with. "Okay. So, I'll clean up, did you want your own room? Yeah, you'll need a computer room for sure, that can be the last room down the hall, and if you wanted your own bedroom it would be right-"

"Ben," Dean said, catching his hand and pulling him to a stop. "We can figure it out later. Right now, um... Maybe we could celebrate?" He took Ben's hand and brushed it over the obvious rise in his khakis. Ben wasn't sure how he hadn't noticed it before.

"You're hard?"

"Ever since I started looking for a suit for you. I decided on a suit, not a tux, but a really, really nice one. With a vest and a tie. Black suit, magenta tie, the jacket is checkered black and white. Suspenders." Dean swallowed hard, then bit his bottom lip. "I also got a forest green tie and an aqua tie. So you could pick, you know, the one you like."

"I'd probably have to try them all out, on different occasions," he teased. Dean bit his lower lip and Ben loved that he could make Dean look that happy. "Yeah, let's celebrate."

"Are you, would you wanna be my bitch tonight?" Dean asked, looking nervous again.

"Fuck yes," Ben said, not even hesitating. "I mean, yes Sir."

Dean nodded, then smiled. He moved into Ben's personal space and slid his fingers under the black chain collar, then yanked Ben forward by it. "Good boy. You're my bitch, aren't you?"

"Yes Sir," he whispered, moving closer to Dean to relieve the pressure on his collar.

Dean chuckled. "You're such a good bitch. Do you like being my bitch?"

"I fucking love it, Sir," Ben answered. He shivered in anticipation.

"Good boy. Go shower, and wash your ass out extra good. Understand?"

"Yes Sir," he agreed, rushing to do what Dean had told him, forgetting that Dean had him by the collar for a second. Dean pulled him back and kissed his cheek before he released him. He speed-walked to the shower. Dean followed behind him more lackadaisical.

"Hey bitch?" Dean asked just as he was pulling his shirt over his head, the shower started already to warm up.

"Yes Sir?" he responded, his throat tight as he threw his shirt to the ground.

"Remember those condoms you got from the party?"

He swallowed hard before answering. "Yes, Sir."

"You still wanna know why I had you take them?"

He nodded, looking at the ground, which made his boner harder to ignore as it tented his underpants. He pushed them down and his erection got caught on the band, then bounced up and hit his lower belly when he got them low enough.

Dean chuckled. "Don't worry, bitch. I'm gonna show you what I wanted them for when you get out of the shower."

He nodded again. "Thank you, Sir."

Dean laughed, his mean laugh. "Don't thank me yet, bitch. Now, wash that ass." Dean smacked his bare cheek just as he was getting ready to step into the shower and he jumped.

"Yes, Sir," he yelped as he stepped into the hot water.

"Hey bitch?"

"Yes, Sir?" he replied, getting more sexy-nervous by the second as he washed his body quickly, knowing Dean was waiting.

Dean chuckled. "I really like it when you call me Sir. Turn off the shower when you're done, step out, and wait."

"Wait, Sir?"

"Don't get a towel. Don't dry yourself. You'll stand at attention for my inspection. Do you understand?"

Ben nodded, then realized that Dean couldn't see him. "Yes, Sir."

"Hurry up, then. Don't make me wait, but that ass better be sparkling."

His dick throbbed, and now that he was washing that area, his asshole started twitching, too. He did a quick once over on the rest of his body, he knew Dean wouldn't be happy if he didn't, then washed his ass with soap, his finger rubbing suds over his hole. "Sir?" he asked, so nervous and excited it was making his voice tremble.

"Bitch?" Dean replied.

"How do I wash..."

Dean let him trail off for a few seconds. "What was that?"

"How do I... wash my ass?" He nearly choked trying to say it. "Like, just the, um, outside?"

Dean's laugh made him shiver. "No, bitch. Squeaky clean, inside and out. Understand?"

"Yes, Sir," he whispered.

"With your finger," Dean continued. "Inside your hole."

Ben gagged. "Yes, Sir."

Dean laughed again as he pierced himself with his soapy digit. He whimpered and Dean moaned. "What a good bitch you are."

"Thank you, Sir," he whispered as he pushed his finger in and out, washing his most intimate of places. "You're the only person I want to be a bitch for." He washed himself out a third time, then rinsed as best he could. He hesitated for only a moment before rinsing his whole body down one final time before he shut the water off and pulling open the curtain. The way Dean was leaning in the doorframe watching him made him flush with shame and arousal.

"You're so sexy," Dean praised, his eyes travelling up and down Ben's body. "Why're you hard?"

"Because of you," Ben whispered.

"I didn't hear you, bitch. Why are you hard?"

"Because of you, Sir," he said louder, though it was difficult with how embarrassed he was.

"Step out of the tub, bitch," Dean directed.

He did, reaching for a towel by habit alone. He pulled his hand back when he realized it, avoiding Dean's gaze. He shivered as water dripped off his body.

"Good boy," Dean praised. "Come here." He followed Dean's direction. Dean picked up a towel Ben hadn't seen on the sink and reached for him, brushing it against his wet skin. "Whose bitch are you?"

"Yours, Sir," he whispered as Dean moved over his left calf and up his thigh with the towel, his touch gentle, but also firm.

"I feel like punishing you, bitch," Dean said. His gaze was focused on Ben's thigh as he moved over to the right one, avoiding Ben's boner.

"Why?" he whined. "Did I do something wrong, Sir?"

Dean looked up at him, biting his lip. "Do I need a reason to punish you, bitch?"

Ben swallowed hard, meeting Dean's eyes. "No Sir."

"I'm gonna punish you because you're mine. To remind you who you belong to."

Ben's fingers traced the collar around his neck as Dean dried his right leg down to the top of his foot. "I know who I belong to, Sir."

Dean caught him tracing the collar and he flushed. "I see you do," Dean agreed. He stood up and began wiping the water from Ben's chest, then moved to his left arm. "A little reinforcement never hurts."

"Yes, Sir," he whispered. Dean's face was close enough that he could lean in and kiss him, but he didn't. Dean wrapped his hands over the towel on Ben's arm and firmly pulled from his bicep until his fingers. He did the same thing on the other side, then turned Ben around and dried his back. "Could you punish me for, ah..."

"Hmm?" Dean asked, his touch growing lighter.

"Could you punish me for letting Liam touch your bitch, sir?"

Dean looked up at him sharply, pausing. "Ben?"

"Please, Sir? I need to be punished for letting another man touch your bitch." He swallowed hard. "He made me dirty, Sir."

Dean watched him carefully for a few breaths, then nodded. "Of course. Spread your legs," Dean commanded. He didn't hesitate. "Fuck, Ben," he whispered, leaning into his body. Ben felt the brush of Dean's lips on his shoulder just before the sharp pain of Dean's bite.

He moaned. Even though it hurt, he loved how it felt, and how possessive Dean was. "Sir," He whispered.

Dean's finger trailed down his spine, his teeth still clamped onto the muscles in his shoulder. The finger trailed lower, stopping just above the cleft of his butt. He whined and Dean laughed, then released his bite. "What's wrong, bitch?" he asked, his tone wicked in just the right way.

"You stopped," he whispered.

"Stopped biting, or stopped touching?"

"Both, Sir."

Dean chuckled. "The night's still young, bitch. Hands on the edge of the tub." Ben didn't move fast enough, slightly confused by the direction, so Dean pushed his lower back down. "Spread your legs more."

He did, feeling incredibly vulnerable when he realized his asshole was on display for Dean. Dean's fingers brushed over the back of his balls and he gasped in surprise. Dean laughed, then stroked him again. He felt the skin scrunch up under Dean's attention, which didn't help the sudden aching need that was his dick.

"I want you, Sir," he gasped as Dean's finger trailed from his sack up his taint, and then to his rosebud.

"You've gotten quite greedy, haven't you?" Dean asked, tisking loudly. "I've probably spoiled you too much." He pushed his finger against Ben's hole, not enough to pierce him, just a bit of pressure. Ben squeaked and clenched instinctively, then forced himself to relax.

"No, Sir," he begged, pressing his ass back into Dean's finger. It disappeared and he whined.

"You want this?" Dean asked, pressing his finger against Ben's hole again.

"Yes," he said, his voice barely a whisper.

"You want my finger in your straight-boy hole?" Dean asked. He shivered when Dean wrapped himself around Ben's body from behind. Dean's smell was stronger this close, it made his mouth water. Dean was hard, too, he could feel the shape of his cock against his ass, hidden behind fabric. It didn't fit into his crack properly, angled due to the confines of his pants, and Ben found he was slightly disappointed.

He wanted to feel Dean properly. Before he even thought it through he reached back and adjusted Dean's member, then pressed his ass against it, grinding until it fell into place. It felt good, naughty and comforting at the same time.

"Mmm, Ben," Dean hummed into his ear. "You're so perfect." Dean's cold fingers wrapped around his cock, his other hand around his chest holding him close. He slowly pumped Ben's cock, too slow. It was more about the sensation as Dean's hand slowly crested and waned. A second later he began grinding himself against Ben's ass, pressing his hot cock into his crack, thrusting in time to his hand.

"Dean," he moaned.

"You like this?" Dean asked, emphasizing his words with a hard squeeze to his manhood.

"Yes," Ben agreed, eyes closed so he could experience the sensations better.

Dean thrust against Ben once more before he let go and stepped back. Ben's backside was cold where Dean had been. "Stay," Dean commanded.

"Yes Sir."

Dean's fingers pried his asscheeks apart. Ben didn't have time to react before Dean's tongue traced his crack and circled his tight bud. He whimpered, his hips moving forward by reflex alone, but Dean held him firmly with one hand. A sharp smack landed on his left cheek, leaving a stingy sensation in its wake.

"Stay still." Dean returned to his ass, his tongue dancing over the super-sensitive flesh. Ben tried hard to stand still, but he failed. Dean snorted, then used a finger to pierce Ben's hole. "Good job, bitch. You taste nice and clean."