Ben Loves a Challenge Ch. 15

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Dean reacts to Ben's tux, and Ben gets hit on at the club.
9.5k words
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Part 15 of the 18 part series

Updated 06/09/2023
Created 10/01/2019
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Ben paced, then tugged at his wine colored tie again. Dean was late, and he was really second guessing this whole tuxedo thing. He felt silly and overdressed, and was beginning to question why he ever thought D'metrius had been serious. Obviously he'd been messing with him, but it was an expensive trick at almost three hundred dollars. How much would it have cost him if he'd bought it? Thank god he hadn't let D'metrius talk him into that.

The shoes were possibly the worst shoes in the world. They rubbed him wrong in ten different ways, and since Dean still wasn't there he wasn't gonna keep wearing them. He sat down on the couch and untied one, then jumped up as his striped grey cat decided that now was the perfect time to sit on his lap.

She was not a lap cat. She was a demon. He tripped as he jumped up, then caught himself, feeling like a complete tool. Tennille looked at him, annoyed, then raised her leg and licked her butthole, making eye contact with him after her first long lick. He kicked off his other shoe, scowling at his cat.

"Sorry, kitty, but I already knew you were evil. Get over it." She licked her butt again, then licked her paw and crossed her face with it. He shrugged, then began to pace again.

Where was Dean? Dean was gonna make so much fun of him when he got here, he just knew it. He should just change now and save himself the humiliation. He took off the tuxedo jacket, then ran his hands down his black tuxedo vest. It was a snug fit. He'd been assured that was the way that they were worn, but he had his reservations. Just a few more minutes wouldn't hurt, right?

He'd been worried that Dean would show up as he was trying to figure out how to wear the tux, but he didn't. Putting on the tux wasn't actually all that hard once he tried. It felt really intimidating at the bridal shop, but that was probably because of the tuxedo tidal wave D'metrius made him wade through.

He checked the time on his phone again, Dean was now almost forty minutes late, and not even a call or a text. He paced harder. Tennille licked her tail wearing a look of feline disapproval. "Sorry if I'm annoying you, princess," he snapped at the cat, feeling dumb.

Nevermind, he'd keep the tux on just until Dean showed up. At least Dean would have a good laugh. He pulled the jacket back on and buttoned it up, then smoothed it out again. If he looked stupid, like, if Dean laughed at him he could change. Yeah, once Dean saw him and got his fill of making fun of him he'd change into something casual and they'd leave, and since he'd asked Dean to be early he'd have time to rectify his naivety and they still wouldn't be late.

If Dean showed up anytime soon, at least. He thought about calling Dean and changed his mind, too embarrassed to call, as if Dean would be able to see his ridiculous tux through the phone.

He heard the sound of gravel crunch in his driveway and then an engine cut. He ran to the window and pulled the curtain aside to catch Dean climbing out of his car. He leaned back inside and grabbed something out, a duffle bag, then shut the door. Ben pulled the curtain closed, but he was sure Dean had seen him being self-conscious.

He went to the front door, then walked away, like he'd be able to trick Dean into thinking he hadn't been pacing like a teenager before prom. Dean knocked. He hesitated, steeled his resolve, swallowed hard, then ran back to the door and pulled it open.

"Hey Ben, sorry I'm late," Dean said, pushing his way into Ben's house. He headed straight to the couch without even looking his way, talking the whole time. "You won't believe the day I had, like, such stupid shit. My brother called me out of the blue, Sean, the middle one, and I didn't answer, then I almost called him back but he didn't leave a message and I was all freaking out about it for like two hours."

Dean threw his duffle bag on the couch and leaned down to pet Tennille. She mewled piteously at him, as if Ben was starving her for both food and attention. Dean paused his monologue and reached out to her. His bossy demoness-cat leaned into Dean's hand, rubbing her face against his palm. Ben shot his cat a glare as she let Dean pet her in a way that she never let Ben pet her.

"Aww, who's a sweet girl?" Dean asked as he scritched her behind the ear. Tennille's loving act was pissing him off. "Yeah, who's a pretty kitty?"

Ben put his face away when he realized he was jealous of the attention Dean was paying to his cat. He couldn't quite shut down his jealousy, though. Dean had him trained well.

Dean stood back up, wiping his hands on his pants before he continued. "So, yeah, there was all that. And then I realized I forgot my bag at home like halfway here, so I went back to get it and then I had to get gas and..."

Dean's monologue trailed off when he finally looked up at Ben. He couldn't read the look on Dean's face and it had him squirming, eyes quickly locking on Dean's shoes. Dean was wearing the new shoes he'd bought him for Christmas, which made him feel a tiny bit better, but it was fleeting.

"Shit," he swore. "Fuck. I'm sorry, I'm ridiculous, I should get changed. It's, I mean, I asked D'metrius what I should wear, cause I didn't wanna embarrass you tonight, and I shoulda known he was fucking with me, I just didn't-"

"Ben, shut up," Dean said in his bedroom commanding voice.

Ben heard the command but it didn't register right away, he was overwhelmed by how deeply he regretted letting D'metrius mess with him like this. He should've known better. He turned towards the hallway, planning his escape. "Sorry, I really, I mean, I just didn't wanna embarrass you, and now I've gone and... Dean?"

Dean grabbed his arm, interrupting his self depreciation and also preventing him from running. "Ben, shut up, yea?" Dean pulled him by the arm and turned him around. "Oh, fuck." Ben was frozen, unsure what to do, still too ashamed to look up at Dean.

"Sorry..." God, the way that Dean's hand squeezed his forearm, possessive and firm, sent a surge of blood to his loins.

"Ben, are you wearing the extra present I got you for Christmas like you said you would?"

"Sorry, Dean, I mean, yeah, of course I am, cause you told me to, but, like, I can change out of the tux first, just gimme a-"

Dean squeezed on his arm again. "Ben, shut up, yea?"

Ben nodded, still studying the floor. "Yeah. Okay."

"Look at me, yea?" Dean asked, pulling him a step closer. He almost stumbled before his feet worked properly. "Ben, look at me."

He couldn't deny Dean when he asked like that, because he wasn't actually asking. Ben looked up, so worried that he'd disappointed Dean that it was eating a hole in his stomach.

Dean bit his lower lip, then sucked in a deep breath. "Fuck, Ben. You're really wearing them?"

"What? The underwear?" Dean nodded. Ben wasn't entirely sure, but he was slowly changing his mind about D'metrius messing with him. The look on Dean's face had him swallowing hard. "Yea. You, um, told me to."

"Good boy," Dean praised, his tone lower. "Fuck, Ben."

Ben sucked in a deep breath. "Is it okay?"

"Is it okay? Fuck, Ben, show me, yea?"

"What? The underwear?"

Dean released his arm, then was fumbling with the tux coat's buttons. A second later he forced it off Ben's shoulders, then trailed his eyes down his body like he was Dean's favorite food. "Yes, Ben, show me your underwear."

"Okay," Ben said, his hands shaking with all of the anxiety he was feeling in every direction. He reached up to unbutton his vest and Dean slapped his hand away hard enough to sting.

Ben pulled it back and rubbed it. "Leave it," Dean barked. "Don't undress anymore. Just show me your g-string."

"Don't undress?" he asked, confused.

Dean licked his lips. "Unzip and show me," he demanded.

Ben shivered in anticipation, then unbuttoned and unzipped his fly and spread it open. "Is this okay?"

"More," Dean said.

Ben almost whined then caught himself. He wiggled, trying to get the pants pulled down without disconnecting the suspenders.

"You're wearing suspenders?" Dean asked, a purr in his voice that had him looking up. Dean watched him hungrily, and he wasn't sure he'd ever seen Dean like this before. He really, really liked it. "Shit, Ben. You're wearing suspenders. And my underwear. Oh fuck, Ben..."

"Do you... Do you like it?"

Dean dropped to his knees, his fingers tracing over the straps of his g-string all the way back to his ass on both sides. "Do I like it?" Dean exhaled hard. "Oh fuck, Ben, I need your cum right now."

"Wait, what?

Dean didn't answer him, he leaned in and rubbed his face on the silky underwear that had been his "stocking stuffer" from Dean. He wasn't expecting it and staggered back one step. Dean pulled him back by his hips, then spread his fly open wider, tugging his pants as open as he could without taking anything else off.

"Fuck," Dean whispered, then licked Ben's shaft over the pouch of the g-string. Dean moaned as Ben slid his fingers into his hair. "Take it out Ben."

Ben reached for himself and Dean smacked his hand away again with a growl. "I need your cum in my belly, Ben. Now. I need it. Fuck my face, Ben. Just, fuck my face!"

Dean licked his package again and growled in the back of throat. He grazed his teeth over Ben's quickly firming manhood. He looked up, the look in his eyes making Ben moan, then he scraped his teeth down Ben's lower belly until he caught the top of the g-string pouch between them.

Dean continually redefined the definition of sexy in his book, and this was suddenly turning into its very own chapter. Dean yanked forward and down, freeing his now fully erect dick. Before his next breath he was in Dean's mouth. "Dean! Shit, Dean, slow down!""

Dean pulled back, looking frantic. "I need your cum, please, Ben."

He sucked his lower lip into his mouth, eyes locked with Dean's. "Yes, Sir," he whispered, threading his fingers through Dean's hair again. Dean kissed the tip of his cock, looking up and meeting his eyes again. "Shit, Dean. You're so freaking sexy."

"Don't lie," Dean chided, then snorted before he pushed his mouth down on his shaft. Ben pulled him down further, slightly rocking his hips as he pushed his way down Dean's throat.

"Not lying," he gasped as Dean did something with his tongue and some suction that had his toes curling. He swayed and Dean caught him, then pushed him towards the couch without breaking suction on his cock. Ben went to sit but Dean bit him hard enough to freeze him, then continued bobbing. The message delivered, Ben leaned against the side of the couch, still standing because Dean wanted him standing.

He moved Dean's head with his fingers buried in that silky hair, and with small rotations of his hips. Unfortunately, it had been a few days since they'd last been together, and with Dean acting like Ben was his drug of choice and he needed a hit like he'd never needed one before, he wasn't going to last. He slowed down and stopped moving his hips, trying not to cum way too soon.

Dean obviously didn't like Ben's hesitation because he slapped one of his hands out of his hair and began going to town on his rod. Dean growled and sucked hard, then scraped his teeth gently down his shaft as he pulled back. Dean looked up at him when only the head of his dick was between his lips and the message in his eyes was clear. Dean was in charge. He swallowed hard and gave into Dean completely.

"Shit, Dean, you look so good sucking my cock," Ben whispered. "Shit, so good. You make me feel sexy, Dean." Dean growled and moved faster, and the way Dean was going to town on his cock was way too good. "Dean, slow down... I'm can't... I'm gonna cum," he begged, gasping for breath between every few words.

Dean moaned, then sped up. His fingers were flexing on Ben's ass over his trousers, pulling his hips in time with his sucking. Dean made eye contact with him again and it was too much.

"Coming," he gasped. His orgasm pulsed, he could feel Dean swallow just before his next surge of cum. "Dean. Oh, shit, Dean," he gasped. Dean moaned then swallowed again, the contraction of his throat muscles making it even better. "Fuck, Dean. Don't stop, please, Sir, don't stop."

His hips were bouncing off the couch and into Dean's face, and he held Dean's head like a lifeline as his orgasm slowly receded. Once he caught his breath he looked down at Dean, still sucking gently on his flagging member. The sight of cum leaking from the corners of Dean's lips had his spent dick twitching again.

Dean really did have him trained, he realized as his asshole twitched along with his dick. Dean pulled off his cock and stood up, his hands trailing up his vest. He didn't say anything, just wrapped his cold hands around Ben's neck and pulled him close, then broke his way into his mouth. Ben was mildly disappointed to find that Dean hadn't snowballed him.

That thought should have messed him up, that he'd wanted to be snowballed, but he couldn't find the energy to spend on being upset about it. Instead, he kissed Dean back.

"Thought you were gonna make me eat my cum," Ben whispered when Dean pulled away. Dean still had that frantic look in his eyes, and Ben's asshole twitched again.

"I needed it," Dean said, his tone velvety. "Wanna fuck you, Ben. Wanna be inside you. Wanna cum inside you. Wanna make you mine, mark you. I want you so much, Ben."

Even though he just came, he felt blood returning to his cock. He was such a greedy bitch. He leaned in and kissed Dean's neck, then kissed his way down to his collar. "We're gonna be late," he noted with a small nip to Dean's throat.

Dean caught his chin between his fingers and dragged Ben back to his mouth. "Don't care." He kissed him hard and Ben licked and sucked, enjoying the residual taste of cum in Dean's mouth. Dean's fingers forced their way down the back of his pants, but the tux was a slim fit and Dean's hands couldn't dip as deep as he wanted. "Is this yours?"

"Hmm?" Ben asked, kissing Dean's jawline. It was smooth, he must have shaved just before he'd come.

"The tux, did you buy it?" Dean growled, his fingers wiggling as they tried to slip deeper.

He shook his head. "Rented. Due back on the second."

"Shit. Okay. Suck my cock then? I don't wanna ruin this."

Ben pulled back. "Huh?"

"It's hella expensive if you fuck up a rental tux. I'll buy you one, so for now just suck my cock so I can cum down your throat." Dean pulled his hands out of Ben's pants, then wrapped them around the back of his neck so possessively that if Ben wasn't leaning on the couch he would've staggered.

"You want me to wear this again?"

"Fuck yea," Dean grunted. "On your knees, bitch. It'll be quick. I'm not gonna last, you're too damn sexy." Dean pushed him down with that possessive grip until he dropped to the floor on his knees. Dean's hungry eyes had him eager to please, and he reached forward without being told and unbuckled Dean's belt, then began breaking him out of his pants. Dean's cock was perfect, but it always was. He closed his mouth over the tip and sucked up his precum. Dean hummed in approval. "Don't spill a drop, don't ruin this tux. You'll be punished if you do."

Ben pulled back and smiled. "That's not really giving me incentive not to, you like punishing me, and so do I."

"I do, but you're not supposed to like being punished. I'll have to discipline you better," Dean said, pulling Ben's head back towards his drool-inducing scepter.

Ben moaned. "Yes, please, Sir," he said before Dean's hardness pierced his lips. The trail of precum had him sinking deeper. He wished he could deepthroat like Dean could, he wanted to make Dean feel the absolute best.

"You're incorrigible," Dean chided. "Fuck, Ben. You're my every wet dream come to life."

Hearing that made him feel incredible, like his whole body was a tool for Dean's enjoyment. He licked the underside of Dean's cock and grazed his teeth along the top side of it. Dean moaned, his fingers flexing in Ben's hair. His hips bucked and Ben tried hard not to gag on Dean's dick, but he failed.

Dean pulled back quickly, and almost pulled himself from Ben's mouth, but grabbed Dean's hips and held him still while he recovered. It didn't take long until he was back on Dean's shaft, sucking it as deep as he could go. One day he'd learn to deepthroat, but today wasn't that day.

"Sorry, sorry, yea?" Dean whispered. Ben shook his head in a micromovement, then sped up his pace, bobbing eagerly up and down on his flesh-flavored treat. "Ben," Dean moaned. "Love you, Ben. Gonna cum, don't spill it, don't..."

Dean moaned just as his first shot of cum sprayed with enough force for Ben to feel it against the back of his throat. He hummed as he swallowed it down just in time for his mouth to fill with Dean's second shot. His asshole was twitching, he couldn't stop it from spasming each time Dean loaded his mouth with another serving of his bitter, creamy seed.

Dean's hands were wrapped around his neck, pulling him forward until Dean's shaft was almost gagging him. Another shot of cum had him choking as it shot against the back of his throat. He felt some of it go up his nose and knew he'd be smelling Dean's cum all night. It made him want to come again, made him so hard that it hurt, and his ass feeling so empty that he didn't care about anything other than Dean.

"God, Ben. You're so sexy, so fucking sexy." Dean pulled him back and he sucked hard, cleaning Dean's dick until it popped from his lips. Dean's cock was quickly becoming his favorite thing in the whole world, just behind Dean. "Show me you swallowed it all, yea?"

Ben opened his mouth for Dean's inspection. Dean made a show of looking into his mouth, then dropped to his knees and kissed him hard. It was demanding and frantic, but also passionate and loving all at the same time. Ben lost himself to Dean's mouth and hands for some unmeasurable amount of time.

Eventually Dean pulled away, standing up. He took Ben's hands and pulled him up, too, then tucked Ben back into his pouch. Ben readjusted, all the shifting had pulled the string very much into his ass, then went to zip back up but Dean touched his hand.

"Can I, I just wanna look, yea?"

"We really are gonna be late."

Dean sighed. "I know, but... I don't wanna go anymore. I wanna stay here and look at you all night. Forever."

"Why not just take a picture?"

Dean looked up at him in surprise. "You'd let me take a pic?"

Ben shrugged. "Why not? I'm still kinda hard, but probably not as hard as before. Will it ruin the pic?"

"You're serious? You're seriously gonna let me take a picture of you?"

Ben narrowed his eyes. "Is this a trick? Why wouldn't I?"

Dean looked a little stunned. "Cause of a million reasons. Cause you weren't gay before me. Because it's a sexy picture of you and the internet exists. Cause we've only been dating for a few months. Cause-"

"Well, if you don't wanna take the picture I can just put it away..."

"No, wait!" Dean interjected. "Please!"

Ben chuckled. "You can take pictures of me all you want. But, ah, maybe not of my face in this one?"

"Are you sure?" Ben nodded. "For sure-sure?"

"Take the picture!" Ben barked.

The smile on Dean's face made it worth it. Made everything worth it. "Yea. Sure." He adjusted himself and pulled his phone out, then knelt down in front of Ben again. Ben sucked in his gut, hoping he didn't look too pudgy. "Stay there, right there. Just..." Ben heard the camera app on Dean's phone snap a few pictures. "You said Metri told you to get this?"

Dean pushed himself up off the floor, reviewing the pics he'd taken. "Yeah. I called him and asked him what I should wear, then he met me at a bridal shop and I tried on a million and a half tuxes until he said this was the one. I fucking hate the shoes, by the way. I really, really don't wanna wear them."

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