Ben Loves a Challenge Ch. 10

Dean snorted. "Why do you hate them so much?"

Ben looked up, realizing that they were parked in the lot of Dean's apartment building. "We're here already?" Dean nodded, watching Ben from the corner of his eyes.

He took a deep breath. He'd never told anyone this before, and worried it would sound stupid. "Yeah. So, I guess it's cause one time I went to one with Hugh and Justin, I'd never been to one before, just hadn't ever really thought about it. The first one I go to, I'm not kidding. The first one ruined me on then all forever.

"We go and I'm curious, but it was old hat for Justin and Hugh. I'm assuming you know the general idea. Girl comes out and dances. Then she goes around and does public or private lap dances between her stage show. First girl comes out and I don't really think anything of it, but the second girl?

"It was my sister's best friend from high school, the second girl. We both recognized each other. God that was weird. She was hot, I definitely jerked off to her in high school, but seeing her there, humping a brass pole? That really fucked up me up right there.

"Hugh somehow knew something was up with me, so of course he bought a lap dance for me and I hard passed, but he'd already paid so he took it, then he groped her and treated her terribly. Worst part? It wasn't just him. I watched her get pawed all night. It wasn't my proudest moment.

"I just accepted that that was how it was, dudes gave money to strippers for a face-full of tits. I don't know that I've ever really gotten over it, though. Like, those girls are people's friends, sisters, daughters, mothers. Shit like that. They're real people, which I know sounds dumb, but it wasn't something I'd thought about before. Like I know they chose to be there, but did they really? Maybe. I dunno.

"Either way, it makes me feel dirty, like I'm the one who's responsible for the girls. I tip well and never buy dances."

Dean turned to him, his face full of emotion. "I think I love you even more after hearing that, Ben."

"I hope I can keep it up, then," he said, unsure what else to say. He shouldn't have said anything, cause that sounded stupid.

Dean chuckled. "You good?"

"Dean, I'm fucking fantastic. Seriously. Like, better than good, better than great."

"I wanna punish you, and push you up to the next plug. But, when we have sex for the first time, I want that to be just us. Like, just you and me. Not you as my bitch. Just, you know. Like, just us... Is that okay?"

Ben took Dean's hands in his own. "That sounds wonderful." He leaned across the car and caught Dean's mouth in a slow, sensual kiss. Dean's fingers found their way into his hair and they kissed until his back ached from the position and he pulled back. "I'm good."

Dean nodded. "You're gonna go straight to my bedroom. You will undress and present your ass to me for inspection. Do you understand?"

"Yes, Sir."

"Good. Don't say anything unless asked, unless it's a color. Understood?"

He nodded. "Yes, Sir."

Dean nodded, then opened his door and headed towards his apartment without another glance. Ben chased him inside, his dick hard and needy. The second he was in Dean's apartment he ran back to his room and stripped down as quick as he could. He climbed onto Dean's bed and pushed his face against the comforter as he pushed his ass up high.

It felt like forever before Dean mosied into the room. Ben's body shook with trepidation, worried that Dean would leave him like that, but also worried about what Dean was gonna do to him.

"Oh my, a beautiful ass just waiting for me. I could get used to this." He craned his neck to watch Dean move into the room. Dean's chilled hands framed his ass, and he sprinkled kisses across his right cheek as he fell to his knees.

He moved to the left cheek, kissing it, too, before he moved into nips. The nips were pleasant, and then turned into full on bites. Ben moaned as Dean caught his flesh between his teeth. It was shocking when Dean pulled the plug from his ass, he'd been distracted by the kisses. The intensity of the sensations had him dropping his ass down.

Dean chuckled, then his hands and bites were gone. Ben whined at the strange emptiness inside him and Dean chuckled again. "I'm just getting the next size up. Don't worry, bitch, we aren't even close to being finished."

He moaned, closing his eyes when Dean returned with the next butt plug. He lifted his ass back into the air and Dean smacked it lightly, the gesture sending a ripple through his whole body. Kisses began to rain down on his ass again, and again distracted him from the second butt plug. He jumped when it pressed against his hole and Dean laughed.

"Shh, bitch. You're in trouble. I'm going to plant this plug inside you, and then you're gonna get some discipline."

"Yes, Sir," he whispered.

Dean smacked his ass hard enough he could still feel it when his hand lifted. "I told you not to speak unless addressed, didn't I?"

"Sorry, Sir," he apologized. The plug swirled deliciously around the tight ring of muscle all the while, and he pushed slightly back into it, willing Dean to press it deeper.

"You're getting awful greedy, my little bitch," Dean said sweetly. He pressed the plug until Ben's body tensed with the sharp pain of slightly too much stretching. "Shh," he cooed, pushing the plug in and out, stopping just before the painful area. "You're doing well."

The movements were hypnotic and he lost time as he paid attention to the sensation, and to relaxing so that he could take the next plug. Dean continued to rock it in and out, stopping just before it was painful, only to start again. His attention was drawn back as Dean pressed it a little too far and the pain started again, but just as soon he felt it vacuum seal into his ass again as it seated deep inside him.

"Mmm," Dean moaned. "You're beautiful." For a few breaths Dean didn't say anything, and he didn't touch Ben, either. Just when he was starting to get worried he felt Dean's hand on his lower back again. "Time for punishment. Stand up."

Ben twisted around, intensely aware of the foriegn object in his ass. He stood at attention, his hands at his sides, then behind his back, then at his sides again. He didn't know what to do with them.

"Hands behind your back," Dean commanded, then nodded when he followed direction. "Good." Dean stalked towards him, then reached out. Ben thought he was going to grab his chin, but he reached lower, grabbing the metal ring in the center of his collar. Dean easily looped his finger through the hoop and pulled Ben forward.

The little yelp he let out was embarrassing, but Dean seemed to appreciate it. "Your collar is good for two things." Dean tugged and he took a step forward. "What are they?"

He swallowed hard before he answered. "One's to say I belong to you." Dean nodded. "The second... so you can lead me around, like a dog?"

Dean tugged on his collar again. "Good boy." Dean turned, his finger still looped in Ben's collar and walked towards his bedroom door. Ben only had one option, so he followed Dean. "Wouldn't it be fun," Dean began as they walked up the hallway towards the kitchen and living room, "to go for a walk like this? I could buy you a leash, and we could take you for a walk."

"Yes, Sir," he whimpered.

Dean tugged him forward and paraded him around the living room. "Really, we need a leash, then I can truly walk you like the bitch you are. Would you like that?"

Dean didn't stop to let him talk, he was now looping back to the bedroom. "Yes, Sir."

Dean stopped and looked at him, looking for signs that Ben might be placating him. The idea of him being Dean's bitch was so hot that he was trailing a drop of precum from his slit down the underside of his manhood.

"Woof," he play-barked. Dean looked confused, so he did it again. "Woof!"

A wicked smile bloomed on Dean's lips. "All good bitches need bred, did you know that?"

"If you say so, Sir."

Dean snorted. "Are you a good bitch?"

"I wanna be, Sir," he replied instantly.

"Should I breed you?"

"God, yes, Sir," he said, losing himself to the game for a second.

"Fuck, Ben," Dean said under his breath. He tugged on the chain again and Ben was following him back to his room. "I'm gonna breed you, bitch. You want that?"

"Please," he breathed out. A second later he followed it up with "Sir.".

Dean released his collar when they got back to his bed. "Get back on the bed, bitch. Ass up, head down, show me you're ready to breed."

He quickly followed Dean's instructions, and before he had settled Dean was rocking the plug in his ass. He kissed and nipped the bite-tender flesh of his ass as he rocked, pushing it in and out of Ben's eager hole.

"That's right," Dean coached. "Rock with the plug, get your hole nice and relaxed for the next one. After that one you can finally have your treat."

Ben whined, moving his hips slightly to continue rocking the toy in and out of his ass. Once it slid in and out of him with ease Dean pulled it away. He closed his eyes, eager to master the third one so that he and Dean could finally be together. He never realized it was so much work for men to have sex together.

All thoughts escaped his brain when the third plug pressed its thicker girth against his hungry hole. He whimpered when he felt the now-familiar sharp pain, frustrated that he wasn't more ready.

"Shh," Dean cooed, rocking it in and out of him between delectable swirls around his ring of muscle. "Soon, bitch. I know you want it. You're doing so well. It'll be easier after this, the first time's always the hardest. Yeah, that's it, rock into it and relax. Once you can take this, you can take me. Do you still want me?"

Dean's dom act was over, he could feel it. Dean was growing nervous, too nervous to continue playing. "I want you, Dean. I wanna skip this one, I just want you. Can I? Please? I wanna feel you, not this rubber toy."

Dean shivered and then the toy was gone. "I can't hold back if you're gonna say shit like that," Dean complained. Ben heard the familiar sound of a condom package ripping open and he turned to watch Dean slide the translucent sleeve over his erection. Once it was seated at the base he threw his jacket off, then pushed his pants down and stepped out of them.

He was unbuttoning the neck of his polo shirt as he approached the bed. "Ben, come here please?"

Ben rolled onto his side, then pushed himself up from the bed, his knees achy from the length of time in the same position. Dean shrugged out of his shirt as Ben stepped into his personal space. For a brief moment neither of them said anything, just stood there so close to one another, but not touching.

Dean's fingers caressed his cheek, a hesitant touch. "Are you sure?"

"Shut up, Dean," he said, stepping closer as he wrapped his hands around Dean's neck and pulled him down into a kiss. Dean kissed him back, needy and desperate, one of his hands catching the back of his neck while the other squeezed his ass firmly.

He couldn't have said who took the first step, but they were moving clumsily towards the bed without breaking away from the kissing. Dean was a good kisser, even when he was clumsy. Ben's cock grew even harder when Dean pushed him to the bed, then mounted his body, pushing him up the bed. Once Ben was where he wanted, Dean lowered his body down, catching Ben beneath him.

Ben spread his legs slightly, mostly distracted by the kisses, but slightly worried about what was next. Not because he was worried it would hurt, that worry had long stopped being a concern. No, he was worried he'd mess it up, since he didn't know what to do. Was there ettiquite to this, was he about to commit some gay faux pas? He didn't want to disappoint Dean, this was important. They'd never have another first time.

Dean broke away from their kiss, lifting his upper body from Ben's. "I love kissing you," Dean said, his eyes full of hunger.

"I'm ready," Ben said, hoping for direction. "Tell me what to do."

Dean nodded, then pushed himself up and rolled off of Ben. Had he done something wrong? Ice water flowed down his spine into his stomach. Meanwhile, Dean crawled to the top of the bed and moved some pillows behind his back.

"Come here," Dean said. It wasn't a command, but it was firm enough that Ben jumped eagerly to comply. "Get on my lap. You won't get that deep, and you can control it yourself, until you get used to it."

Ben exhaled the worry he'd been growing inside. Dean bit his lower lip, and before he could start to worry, Ben crawled towards him.

"I'm not gonna be any good at this," he forewarned.

"You'll be perfect no matter what happens," Dean whispered as he watched Ben climb onto his lap. "Ride me, Ben. Slowly. Hold up, one second," Dean asked nervously. "More lube," he explained as he groped across the bed towards the clear bottle.

He wasn't gonna reach it from there, so Ben leaned back, stretching to grab it. Dean took the opportunity to run his hands over Ben's skin, up his belly to his pecs. "Use a lot, just pump it right onto the condom."

Once Dean seemed to feel there was enough lube on his dick, Ben climbed into his lap again. He was shaking as nearly every emotion flitted through him, one after another after another. Dean grabbed the base of his cock and lined it up, and Ben slowly lowered himself onto the waiting shaft.

"Oh, Ben," Dean moaned as the tip of his cock slipped into his relaxed hole. He felt the muscles try to tense up again and he took three deep breaths before lowering himself ever so slightly down Dean's shaft.

"Don't take this the wrong way," Ben panted out as he backed off Dean's dick. "But you're a lot bigger than I thought."

Dean chuckled nervously. "The first time's like that. You okay?"

"Fantastic," he moaned, sliding Dean's cock deeper inside him. It was so completely different then the plugs had been, so much more real. Dean's rod was harder, but it was also warmer, too. Dean stretched him farther than he'd been stretched and he felt the sharp pain again, but he was tired of waiting, tired of working towards it. He wanted Dean inside him now, wanted to feel what he'd been fantasizing about for so long.

He pushed himself down farther, but Dean caught his hips and stopped him. "Don't rush. We have time. Don't hurt yourself, or we can't do this again later, it'll hurt till it heals."

Ben frowned. "I'm sorry, I'm doing this wrong. Me, not you. I know how important this is."

"Listen, thank you for even trying this with me. I can't even tell you how much it means to me. The sex isn't what's imporant. This, all of this," he said, running his hands down Ben's back, "this's what's important. You're what's important."

It was too emotional for him. He leaned in and caught Dean in a kiss and one of Dean's hands roamed up his back and ended gripping his neck possessively. Dean's other hand rocked Ben's hips slowly and carefully back and forth, not pushing him down but moving the length that was already inside around. Ben lifted his hips slightly and rocked back down onto Dean's shaft, stopping just as it stretched him slightly too much.

"Ben, you're so tight," Dean praised between kisses. "I can't... believe..."

"Maybe I should call you Cinderella. If the shoe fits..."

"You're loco." Dean chuckled and gripped Ben's neck more firmly, pulling him into more kisses. Ben hadn't felt his muscles relax, but he did feel Dean's shaft slowly sinking into his ass. It was tight and took his breath away, but it didn't hurt. Well, it hurt a little, but not in a bad way.

"So full," he moaned as he continued to slip Dean's cock deeper into his ass. He leaned his forehead on Dean's shoulder, breathing carefully as he grew accustomed to the pressure in his ass.

"I want more," Dean whispered. "Once isn't enough."

Ben chuckled, then gasped as the very last inch of Dean's member slipped inside him. "You're in all the way."

Dean's hands danced over his skin, rubbing up and down his back, through his hair, over his ass, up his chest, all between kisses and bites along his collarbone and neck. "Move when you're ready. Tell me if it hurts or you're uncomfortable."

"K," he ground out, forcing himself to relax further. He was tired of waiting, he wanted to push Dean's cockhead over that fun little spot he'd been shown earlier. Just as slowly as he went down he rode back up until just the tip was inside him, then he pushed it back inside himself, concentrating on the movements, on Dean's reactions, and on avoiding the slight twinges of pain here and there.

Everything clicked into place like a switch in his head. The pain disappeared and suddenly Dean's hard rod in his ass was a pleasure he'd never known before. Dean noticed it, too. "You okay?"

"Perfect," he breathed as he pulled himself up Dean's cock, then pushed himself down again.

"You got softer," Dean noted. "But, here, too." There was a frown in his voice and Ben opened his eyes. Dean cupped Ben's cock, only half mast. "Don't force yourself, please. If it's not good for you-"

"Shut up," he said, putting a finger over Dean's lips. "I had to concentrate on this," he said, squeezing down on Dean inside him. Dean rewarded him with a moan. "I'm good. But, if you're worried, you could always play with it for a while."

"I'll play with it for as long as you let me," Dean breathed. "How's your ass?"

Ben smiled playfully, then began to rock himself around the shaft inside his ass. He rocked and slid up and down it until he found the perfect angle to rub the spot that made his toes curl and eyes roll back. Once he found it he couldn't let it alone, he began shifting, using Dean to rub over it nearly constantly.

"Mmm," Dean moaned just before a sharp nip landed on Ben's shoulder. "You found your prostate? You've grown here again, too."

"Feels so good," he cooed. "Dean, I want you to cum."

Dean bit him again as he moaned out in frustration. "Ben," he growled, his cold fingers slipping to Ben's hips. Dean pushed him down, then up, his cold, firm fingers setting the pace. "I won't last long, I've wanted this too long."

"Cum, please," Ben begged. "Cum inside me."

Dean moaned again. "You're killing me, DeLuca."

Ben squeezed down with his ass again and Dean pumped his hips twice as fast, but Ben noticed his movements were shallow. He almost said something, but he knew they had time, so he allowed himself the pleasure of sinking into making Dean come.

Dean's eyes slipped shut and then he was groaning and bouncing his hips up into Ben's ass. God, it felt good, and he had a fleeting thought that getting pounded by Dean might be incredible. Dean cried out as he came, then bit Ben's shoulder hard.

Ben pumped his shaft, already so turned on, Dean's orgasm fueling his own pending orgasm. "That's right," Dean gasped, sounding spacey, "Cum for me, Ben. I want you to get it all over me."

He growled and his hand quickened, his hips still rocking on Dean's cock. "Fuck," he growled, the pressure on his prostate and the look of pure satisfaction on Dean's face pushing him to the peak. "Dean," he moaned, leaning forward to rub his prostate while also landing his first surge of cum on Dean's chest. The second surge hit his belly just above his belly button. The third oozed out onto his hand, which he rubbed onto Dean as well.

He collapsed onto Dean's body, getting his own spunk on himself, but he felt so good he didn't care. His head was ten feet above his body, floating in a blissful cloud of thoughtlessness. Dean's fingers traced his spine, then traced the collar around his neck.

"You're mine," Dean whispered.

Ben chuckled, suddenly feeling sleepy. "Mmm-hmm," he moaned.

"Was it okay?"

"Perfect," Ben said, his voice thick with exhaustion. "I'm so tired now."