Ben Loves a Challenge

Dean brought him home again, only this time he was sober. Ben was so nervous and excited that he could barely contain it. To be honest, he felt like a teenager again. He only had a week to convince Dean he was serious, so he had to make tonight count.

"What were ya thinking for dinner?" Dean asked, kicking off his shoes near the door.

Ben looked down at his own feet. "Oh, shit, sorry about the shoes, I didn't realize." He knelt down and began untying his dress shoes.

"Don't worry about it," Dean dismissed. "It's fine."

"Sure, sorry. Okay, um... I dunno. What do you want?"

Dean laughed. "Seriously? We're already to the point in our not-a-relationship that we have the 'what do you want for dinner' routine?"

"Do you wanna go out, or would you wanna stay in and order something, or I could cook," Ben offered.

"You cook?" Dean asked.

Ben pretended to be offended. "I've lived alone for the last six months. If I hadn't learned how to cook, I'd probably be dead. I mean, nothing too complicated, and I mostly just follow someone else's directions, but I know how to make basics. Tacos, pasta, eggs and bacon, hamburgers. The four basic food groups."

Dean was amused. "I think I have stuff to make tacos, if you wanted to give it a go. It'll have to be soft-shelled, though. I wasn't planning on making tacos, so I only have tortillas for wraps."

"If you show me where stuff is, I'd love to cook for you."

Dean joined him in the kitchen. It started out a little awkward, bumping into each other until they got into a rhythm. It was nice, cooking with Dean, learning who he was by the way he carried himself. It had Ben falling even harder for him.

The tacos were edible, but they weren't his best. It didn't seem to matter to Dean.

"Slow down," Ben said. "There's more where that came from."

"Starving," Dean barked between bites.

"Please don't choke, I promise I'll make more if you're still hungry. Why are you so hungry?"

"Skipped lunch," Dean said, beginning his second taco.

"Cause of me?" Dean nodded, his cheeks rosy. Ben frowned. "Why? You shoulda told me, I'd have brought you a snack or something."

Dean waved it away. "It's fine, I'm fine. This shit happens all the time."

"The talking to me?" Ben teased.

Dean rolled his eyes. "The skipping lunch part. I don't usually have to deal with straight stalkers."

"I'm not gonna apologize," he said, raising his eyebrow in challenge. Dean shrugged, then finished his second taco and began on his third. "You shouldn't skip lunch. I could bring you lunch, sometimes. You could eat with me, in the car or something. Or outside, if it was nice."

Dean fixed him with a flat stare. "You wanna eat lunch with me? With your cunt-licking friends?"

"No, I didn't mean, I wasn't," he sighed. "Still, I could bring you lunch. What do you like to eat?"

"Ben, seriously," Dean said, his third taco already reunited with the first two. "You can't date me."

"You keep saying that, yet here I am. Don't tell me what I can and can't do, Dean," he snapped. "I want a chance with you."

"Why can't you take a hint?" Dean barked back. "You're not gay. Dating me will ruin your life. I will ruin your life."

Ben grabbed his hand. Dean refused to look at him. "Dean, you're not gonna ruin my life. Do you think I'm attractive?"

"I don't see what that has to do with any of this," he said, his pout adorable.

"Answer my question, Dean."

Dean shifted uncomfortably, trying to pull his hand away. Ben held it tight. He didn't answer.

"Do you think I'm attractive? Do you like doing things with me? Did you enjoy what we did the other day? Cause if you didn't, if you don't, I'll stop. I don't wanna make you uncomfortable."

"Stop!" Dean whispered. "Just, stop."

"Sure. I'm sorry. I'll stop, really, if that's what you really want." The thought had his gut clenching painfully. "I'm sorry I misunderstood."

"That's not what I mean! Of course that's not what I want. The point is that it doesn't matter what I want!" Dean exclaimed.

"Yes, it does! I care what you want! I want you to be happy, I wanna make you happy. I know you're having a hard time taking me seriously, but I think you're handsome. I really, really, really enjoyed what we did together. I wanna do it again. And, it's not just the physical stuff, I wanna get to know you. Stop worrying about all that other shit. Just, for right now, worry about me," he said, squeezing Dean's hand between his own.

"I am worrying about you!" Dean said, his voice tight. "I'll ruin your life, Ben. I couldn't bear it if you hated me."

"Why would I hate you? For ruining my life?"

Dean nodded, then looked down.

"But, you're not gonna ruin my life, Dean. I'm an adult. I make my own decisions. You haven't forced me to do anything. You've humored my antics, and... I dunno. I dunno what I'm trying to say, other than that I can make my own decisions. If anyone ruins my life, it'll be me, or my fault. My decision."

"And," he continued before Dean could interject, "I don't believe that any of this with you will ruin my life. If my friends are douche bags about it, then they weren't really my friends. If my family can't accept it... I dunno. I'll have them meet you, and then they'll like you. I mean, I do, and I'm an excellent judge of character."

Dean sighed heavily. "I don't understand why you're even interested in me? Cause I took you home and cleaned you up once?"

"Dean..." He sighed. "I dunno. I mean, we never interacted before, or at least never more than business required. That morning... I was an idiot. I know it seems weird, and like I'm infatuated, but I can honestly tell you that I've never felt this way about anyone. Maybe it's love at first morning after, I dunno."

Dean shook his head. "You're still an idiot."

Ben laughed, squeezing Dean's hand again. "I'm your idiot."

"I didn't say that."

"But you wanted to. Tell me, why'd you take care of me that night?"

Dean shook his head. "I don't wanna."

"Now you hafta," Ben insisted. "Please?" He gave his best pouty, puppy dog face. "Please?"

Dean laughed, and it sounded like he'd been fighting off tears. "Do not."

Yes, you wanna," Ben teased. "You know you do..."

"You're so evil," Dean declared. Ben just smiled. "I've..." Dean trailed off, then took a deep breath and began again. "I already told you, you're exactly my type." He shifted uncomfortable. Ben squeezed his hand and he settled down. Rosy pink filled his cheeks and Ben wanted to kiss them.

"I... You were a dream, Ben. My dream. I'd watch you, from a distance. Then, at Sanjay's party, you were there, your friends left without you, and I couldn't just leave you alone. Seriously, I don't know what I was thinking, bringing you back here."

"You're a really nice guy," Ben said.

"I'm not. I'm really not, Ben. I masturbated to you. Regularly. The smell of you on my sheets gave me fuel for a week, even after you were homophobic." Dean's ears were red now, too.

"I've masturbated to you, too. Come on, date me. For a whole week. I'll do whatever you wanna do, and at the end, if you don't wanna keep going, I'll leave."

"I can fuck you?" Dean asked, avoiding eye contact again. "Can a straight guy like you take it up the ass? I don't like bottoming."

"Oh. Well, okay." He swallowed hard. "Straight or not, I'll try it, as long as we work up to it," he agreed. "I trust you."

"Why?"

"Why do I trust you?" He shrugged. "Why shouldn't I trust you?"

"You don't know me, yet you're willing to let me fuck you? Why?" Dean wouldn't look at him.

"Because I want you. I want you to want me, too." He stared at Dean until he finally met his eyes. "I trust you because you worry so much about me, about what might become of us. Trust me, Dean. Please?"

A tense moment passed and neither of them spoke. Dean stood up suddenly, then pulled his hand away. "I wanna shower," he announced. He looked at Ben, his face crimson. "Stay."

"Yes, sir," he answered, his tension turning to lust.

"I'll be right back."

Dean hadn't been kidding, it was less than five minutes before he returned, hair still wet, dressed in pajama pants and a cotton shirt. He put down his phone and looked up at Dean, taking in his tall, lean frame.

"You didn't move," he noted.

"You told me not to," Ben agreed.

"You're such a freak, DeLuca," Dean said. He held his hand out to Ben. "Would you, ah, wanna, um, come to my room?"

Ben took his hand and allowed himself to be pulled up from his seat. "With pleasure." Dean led him to his bedroom. The door was barely closed before Dean pounced, pushing Ben down to the bed.

"Are you sure?" he asked, tucking a stray wet strand of his sandy brown hair back. "You're sure-sure? That you wanna do this with me?"

Instead of answering, Ben leaned up and caught his mouth in a kiss. Dean moaned, not even trying to fight it. He fell into Ben's lap, landing on his knees on the floor, Dean's legs hanging down on either side of him. Dean's mouth was hot, and he'd used mouthwash or brushed his teeth, because it was minty fresh. While he appreciated the gesture, he wanted to taste Dean more.

He pulled Dean into the bed, kissing him slowly, trying to express how serious his feelings were. He didn't seem to be getting through to Dean with his words so far, so maybe Dean was more of a hands-on kind of learner. They kissed for a while before Dean began to get more aggressive.

Dean slid his hand down Ben's side, fingers trailing slowly until he hit the bed. Firm and quick, those fingers slid under his ass, then lifted slightly. His fingers slipped deeper, questing for where his ass cheeks came together. Dean pressed firmly against his hole through his khakis. He instantly wanted to be wearing less clothes, wanted to know what Dean's finger would feel like pressed directly against his most intimate place.

"Dean," he moaned, one hand in his hair, the other around Dean's neck. "Mmm." He felt like he could do anything, as long as Dean kept touching him, kept kissing him. He pressed his ass into Dean's finger, both terrified of being penetrated and excited at the thought.

"That's not fair," Dean said, panting slightly as he pulled away.

Ben whined. "What's not fair? Come back and kiss me. More kisses."

"The way you say my name, it's not fair. Like-"

Ben pressed a finger over Dean's lips. "Dean, stop thinking you know all the answers for a second. Just... relax. Do what you want now, and I promise that I'll stick around, or leave, whatever you want me to do afterwards. Forget about gay or straight or any of that shit. Right now, it's just you and me. Two people, connecting both physically and emotionally. And I really, really, really wanna take off some of those clothes you're wearing. Purely for connecting purposes, of course."

Dean hesitated, then relented with a snort. "You're such a pain in the ass, you know that?" He accented his statement with a squeeze to Ben's ass cheeks.

He laughed, then pulled Dean back into another kiss. Dean melted against him and they kissed until his lips felt puffy and his head was fuzzy with lust. At some point Dean's shirt had come off, but he was still wearing his. He rolled away, wiggling himself free.

"Hey," Dean protested.

"What, you want me to take the pants off, too?" he teased, unbuttoning his dress shirt.

"No, ah, yeah, I mean, ah..."

Ben loved how flustered he could make Dean. "What do we need, if we're gonna have sex? Is there anything, like, extra?"

Dean's cheeks bloomed pink. "Extra? Jesus, Ben. Sex is sex, but I don't have any condoms. I haven't had a... It's been a while, yea?" he said, looking down.

"Should I go buy some?" he asked.

"What? No, we don't need to have sex right now," Dean dismissed. "I'll just blow you."

"I wanna do something together. Where we both feel good." He was distracted by Dean's erection lifting the inseam of his dress pants. "You look uncomfortable." Dean tried to push him away. He deflected, settling between Dean's thighs, kneeling on the floor as he began working on breaking Dean's manhood out of its polyester-cotton blend prison.

Dean moaned as Ben's hands wrapped around him, lifting his hips up off the bed to yank the pants down his legs. "Ben," Dean whined. His pants slid off, leaving him in a pair of silky black boxers briefs. Part of him wondered why he found the shape of Dean's bulge so arousing, but he did. It didn't really matter why.

"Dean," he said, now working on his own pants. He had an idea, though he wasn't sure if it was gonna work. "Hold on..." His erection bounced as he pulled down his pants and underwear together. Dean's eyes were locked on his member, a mix of longing and fear on his face. "Hey, Dean, sit up. I wanna try something."

He reached out and Dean took his hands, pulling until he sat up, then sat on his lap, knees to either side of Dean's hips. "What?" Dean asked, one eyebrow up.

Ben caught both of their cocks, then shifted his hips until they lined up perfectly. Dean had at least an inch on him, length wise, but they leveled out nicely in this position.

"Together," he said, smiling at Dean.

"You're an idiot, DeLuca," Dean said. He shuddered as Ben slid his hand, overly full with their girths, up the shafts. "You're killing me."

"No sir," Ben said. "I'm loving you."

"Same difference with you," Dean muttered, shifting his hips to pull Ben closer. They kissed again, and it was nice being at the same height as Dean, boosted up on his lap like he was. Ben's hands moved to his ass cheeks and he pulled himself forward, moving his hips in time to the stroking on their shafts. "God, Ben..."

"I really do think I love you," Ben whispered.

Dean moaned and sped up his hips. Ben took the hint, moving his hand faster, too. Dean's cock was hot against his, silky steel, but he didn't have enough friction. He added his other hand, squeezing the cocks firmly between them. The sounds Dean made were encouraging, so he squeezed harder. It felt wonderful, and it had him wondering why people were so homophobic. This was fantastic.

He could feel Dean's pulse throbbing along the length of his cock. "Are you gonna cum?" he whispered into Dean's ear.

Dean shivered, then thrust his hips forward. His head fell forward, landing on Ben's shoulder. "I'm not usually this easy," he moaned.

"I don't know that this... has been particularly easy," he said, his breath ragged. "I wanna make you cum."

Dean shivered. He kissed Ben's shoulder and shivered again. He felt Dean's cock throb just before teeth sank into the skin and muscle at the base of his neck. Dean moaned as he came, his hot ejaculate coating Ben's hand, making it both slick and more sensuous. "Dean, Christ, Dean," he moaned, the pain in his shoulder and the thought of masturbating with Dean's cum pushing him to his finishing point. He shot off a few seconds later in time to the cadence of Dean's hips.

Dean's hips slowed, but he didn't release his bite. Ben shuddered, enjoying the afterglow of his orgasm. Finally, Dean released his bite, then pulled Ben down with him onto the bed. Dean's eyes were closed, a content look on his face. He liked that he put it there.

Ben watched him for a second, then kissed him on his neck. Dean tensed up, but he didn't relent, he just moved down to Dean's collarbone. "Ben," Dean said, voice lazy with contentment.

"Mmm?" he asked, still kissing Dean's bony collarbone. He really was too thin, Ben could see his ribs, too.

"Ben," Dean said, more forcefully. "Stop."

"Don't wanna," he complained, rolling off Dean to spoon into his side.

Dean sighed. "Thank you," he said as he pushed Ben away. "But, stop."

He frowned, unsure of what he did wrong, but he recognized the look on Dean's face. "Yeah. Okay." He sat up, then moved to give Dean space. Dean got up and walked to the closet. He bent over and Ben watched his ass, not entirely sure if he was aroused or appreciative. Dean cleaned himself off, then threw the towel to Ben.

Dean had his black boxers on, and was digging in his drawer. He pulled out a pair of track pants and slid them on, then grabbed a shirt from the closet and slid it over his head. Ben didn't move, he just watched Dean, trying to glean some reason he'd turned so cold again.

"Are you gonna get dressed? Or just sit there naked all night?"

"You're upset. Did I do something wrong?"

"No, you didn't do anything wrong," Dean growled.

I don't understand," Ben admitted.

Dean exhaled, turning away from him. "Why, Ben? Why'd you do that with me? I'm the one who doesn't understand!"

"Jesus, Dean! We just had some nice sexy-fun-times and you're gonna go right back to 'Ben, you're not gay'? Fuck that, Dean. I just put our cocks together and stroked us until we both came. You enjoyed it, right?"

"It's called frot," Dean deflected.

"Frot? What?"

"Rubbing our dicks together. It's called frot," Dean explained, his back to Ben.

Ben rolled his eyes. "Dean, did you enjoy it? I enjoyed it. Stop thinking so much, just, like, enjoy it, okay?"

Dean flinched. "Yeah, sure," he said, but his heart wasn't in it.

He needed to try something else, because Dean wasn't getting it, for whatever reason. "Dean?"

"Yea, Ben?" Dean asked, turning back to him.

Ben patted the bed. "Come here, I wanna cuddle."

"I'm not a woman, Ben," Dean said, rosy cheeks shining.

"Never thought you were, Dean. I just held your cock in my hand. Hell, I'm still partially covered in your cum." He brought his hand up to his face, then licked the cooling wet spot on the backside. "Yup, definitely ejaculate and not lady-cum."

"God, Ben, that's gross," Dean said, flushing from his rosy color to a deeper red.

Ben shrugged. "It's not filet mingon, but it's not terrible, either. It's sexy. Come here, Dean. I wanna cuddle, and I wanna talk. No, I wanna listen, you're gonna talk."

Dean hesitated, then gave in. Ben slid up the bed and slipped under the covers, then pulled Dean down when he got close enough. "Why do you wanna cuddle with a dude?" Dean asked, not really expecting an answer.

"Not a dude, I wanna cuddle with you," he clarified. Dean was stiff as Ben molded himself to his body. "Jesus, Dean. Relax. You're the first person I've ever met that gets more tense after an orgasm. Did you like it? The frot?"

Dean looked away, stifling a snort. "I came, didn't I?"

Ben sniffed. Obviously he didn't understand how to use the term frot. "Yeah, but that could just be from stimulation. Did you enjoy it?"

"You're a tyrant!" Dean snapped. "I enjoyed it. Watching you lick my cum off your hand has me half-hard again. Of course I enjoyed it, I've wanted you for so-" Dean covered his mouth with his hand, obviously realizing he'd said more than he'd wanted to.

"You have me, Dean. I'll do anything you want me to, we'll date for a week. That can mean whatever you want it to, as long as you give me a chance," Ben said, tracing a line on Dean's shirt over his chest.

"It's too good to be true," Dean complained, but he also relaxed. Ben snuggled deeper, resting his still naked junk on top of Dean's clothed thigh. "You're too good to be true. There's gotta be a catch."

Ben shook his head. "No catch. I promise. Here, grab your phone." He pointed over to the floor where Dean's discarded pants were piled up.

"What?"

"Just do it," he insisted. Dean got up reluctantly, then dug in his pants until he found his phone. He turned back to the bed, holding it out to Ben. "No. You're gonna take a picture of me sucking your dick. Just a head-down shot, so that no one can identify it's you. Then, you'll have it, and you can use it against me if I break your trust."

Dean shook his head. "I can't," he said, holding the phone to his chest. "I couldn't do that to you."

"Yes, you can. Yes, you will. I can't do it myself, or I would." Ben crawled out from under the covers and out of bed. He tugged Dean's track pants down around his knees, then caught Dean's hips before he could jump away. "Take the picture, Dean."