Ben Loves a Challenge Ch. 07

A tremor of sexually charged fear shuddered his whole body. Dean could always keep him from coming again tonight, and with nothing but a few stern words.

The sound of a text caught his attention. 'You said you wanted phone sex before?' A second passed and another text bubble popped up. 'Right?'

He swallowed down his excitement and typed in a single word. 'Yes.'

'You alone?'

'Yes. I miss you.'

Dean sent an annoyed emoji. Ben sent back the smiley face with hearts for eyes.

'Take off all your clothes.'

He couldn't help the big, excited smile on his face, or the stab of fear in his gut. 'Already done,' he replied.

'You're such a slut, DeLuca,' Dean responded. A few seconds ticked by as he tried to think of a response, but then Dean sent him another message. 'Show me.'

His cock was tenting the bedsheet already. Did Dean want a whole body picture? Slipping out of bed, he headed back to the bathroom. The light was brighter than the one next to the bed and he squinted for a second as he acclimated, then frowned at his image in the mirror.

He'd skipped working out for a few days, his little poochy belly proof of that. Ben shifted, trying to find the best angle to make him look sexy. It was harder than it looked. How did all those porn actors do it?

He'd finally found a pose he liked when his phone vibrated. 'Sorry. Nvrmnd.'

Ben frowned, then posed again, trying to give a sexy-tiger kind of look. It was more like a pouty puppy, but he sent it anyway. He followed it up with a text. 'Had to find the right angle. Harder than it looks.'

'Show me your dick.'

He took a quick picture looking down, one hand holding his shaft out while the other one struggled to snap the photo. It was a little blurry, but he didn't want Dean to think he wasn't following directions so he sent it anyway.

There were several seconds where he watched Dean begin to type, then stop, then begin again, only to stop again. 'Show me your ass.'

Heat creeped across his face to his ears. Using the mirror, he tried to take a good picture, but it was hard and the lighting was weird. He did his best, then sent it. He didn't love it, but he didn't want to keep Dean waiting.

'Good job.' Those two words has core clenching and his balls tingly.

'Thank you, sir.' Ben waited for Dean's next instructions. He didn't have to wait long.

'Why are you hard?'

He sent back three question marks, unsure of what Dean meant. Of course he was hard, Dean was playing with him over the phone. He wished Dean were here, that he could see his face and body language. Phone sex was hard.

'Thinking of you,' was what he ended up sending.

'Dirty thoughts about me?'

'Um, yeah?'

'You're a bad boy, aren't you?' Suddenly he understood the game again. Phone sex really was hard.

'I'm sorry, sir. You're too sexy to resist.'

Dean sent back the emoji that looked skeptical. 'I should punish you, since you're my bitch.'

How he was this hard, this excited without even hearing Dean's voice should've scared him, but instead it thrilled him to his core. What was it about Dean that made him like this? He'd never been into submission or anything else more than vanilla sex, but Dean brought out things in him he'd never even considered before.

It was awesome.

'Yes, sir.'

A few seconds passed by as he watched Dean type and pause, then type and pause. He wanted to call, to hear Dean's voice, but if Dean hadn't called him, he didn't want to talk on the phone. He'd be good and wait for directions.

'Get a towel, drape it on the side of the bed.'

'Yes, sir.' He followed Dean's orders, then texted him a picture of the proof.

'Good. Now, you need to be punished. Get on your hands and knees, then put your nose against the wall. You will stay there until you hear three texts in a row from me. Do you understand?'

'Like timeout?' he asked.

'Yes, like timeout,' Dean clarified. 'Except you're going to do your timeout like the bitch you are.'

'Yes sir. Going now, sir.'

It was the most shameful thing he'd ever done. He got on his hands and knees, shivering a little now that the warmth of his shower had faded and he was still naked. The only really good place for him to do it was between the bed and the wall, but it was a tight squeeze. His ass pressed against the mattress and his face ended up smooshed against the wall because there wasn't enough room for his whole body.

He was intensely aware of his cock. It ached and he wanted to touch himself so bad, but he couldn't. He didn't want to ruin his punishment, or earn more punishment. Or did he? The thought of being mischievous ran through his mind, he found he both wanted and dreaded future punishment.

It was confusing, but he accepted it for what it was. He could worry about it later, right now all he could think about was his discomfort, both from his position and from his cock. He tried to shift his position, but wiggling his hips only caused his ass cheeks to spread apart, making him feel ten times more exposed. He wished he could send a picture to Dean, to prove he was following directions, but he couldn't without leaving his position.

He'd never felt his precum before, but now that he was nothing but need, now that he was in this embarrassing position with his ass cheeks spread wide, he felt it. A wet spot on the tip of his cock, and then he could feel it slowly dripping, the thick fluid pulling more from his slit as it succumbed to gravity.

He moaned, but no one was there to hear him. Time passed, it felt like ages. His moans were too loud, he had to stop making noise or he wouldn't hear Dean's texts.

There was the water droplet sound of a text notification, and his heart hammered in his throat. He listened hard, but there were no further sounds. He groaned, wiggling his ass against the bed. His hole pressed against the fabric, sending a pulse of pure pleasure that filled him with longing. He imagined Dean chiding him for enjoying something touching his straight-boy hole. He pressed back harder, teasing himself with the pressure.

This time there were two droplets in a row, and he nearly jumped up to get his phone, but the third one never came. He moaned again, pressing himself hard enough against the bed that the mattress shifted and he lost the delicious pressure against his most intimate of places. It did relieve the pressure of his face smashed against the textured wallpaper, though.

His knees were beginning to ache when he heard three texts in a row, drop, drop, drop, and he was out of his timeout corner in a flash. He grabbed his phone and read the texts from Dean. In order they read, 'You didn't break the rules, did you?', 'Still in timeout?', then three eggplant emojis in a row, then the last text, ''How was timeout?'

He sent back the embarrassed emoji.

'You didn't break the rules, did you?'

'No, sir,' he replied, his heart beating so hard he could feel it in his ears. His cock was a wet mess, the head covered in precum, so hard it was nearly purple.

'Good job,' Dean replied. After another second a second text came. 'Do you wanna cum?'

'Yes, sir. Please,' he said, wanting to type more. He restrained himself, but only just.

Dean sent a devil smiley face emoji. 'Remember the towel?'

'Yes, sir.'

'Lean against it, with your knees on the floor, and your hands over the bed, so that your torso is against the towel.'

He shivered. He couldn't feel the cold anymore, his body seemed to be on fire as Dean shamed him. He moved into position. The towel was rough against his skin, and even the barest brush of it had another surge of precum leaking out. 'Done, sir.'

'No hands, Ben. If you wanna cum, you hump the towel.'

He swallowed hard three times as he tried to figure out what to reply with. He went with his standby. 'Yes, sir.'

He put the phone down next to him, wishing he'd turned the lights out, but the bed and bathroom light were both on, illuminating his shame. He wanted to hear Dean, needed to hear Dean tell him what to do, this wasn't enough. His phone was ringing before he realized what he was doing, and it was too late now.

Would Dean punish him further? He both hoped so and dreaded it.

"Ben, is everything-"

Dean sounded worried. He hadn't intended for him to sound worried. "Sir, I need you to tell me what to do," he begged, cutting Dean off. He sounded so lavacious, his own words added to his shame.

"Oh. Are you against the bed? Turn on speaker phone."

"Okay," he said, following directions. He pushed his phone a little away from him so he didn't knock it off the bed. "I'm in position."

"Describe it to me, I can't see it," Dean demanded.

Ben had to swallow down his shame. "I put the towel over the end of the bed, like you told me. My knees are on the floor and my hands on the bed."

"Your hands need to stay put. If you take them off the bed before I tell you to, you'll earn more punishment. Do you understand?" God, the way Dean spoke to him was maddeningly arousing.

"Yes, sir."

"You need to stay in position, but other than that, you can try to get yourself off however you can."

"Thank you, sir," he said, his hips pressing his dick into the mattress. He was glad he'd put the towel at the foot of the bed, this way he wouldn't shift the mattress any further.

"What are you doing?" Dean asked, sounding almost bored.

"Um... mmm... Humping..." he dropped his voice down lower, unable to stay it louder as shame tightened his asshole. "Humping the bed."

"You're humping the bed, Ben? So naughty."

He moaned, he couldn't help it. "Humping the bed," he whispered. "Cause I'm your bitch."

Dean made a pleased sound. "Yea, you're my bitch, aren'tcha, yea?"

"Yes, sir," he moaned, speeding up his humping. His legs protested from yet a second odd angle, but it didn't take away from how good it felt.

"How's the towel feel against your dick, bitch?"

He was panting now, getting close. "Scratchy," he whispered.

"Good. You've been bad, so you need discipline."

"Thank you, sir," he moaned.

"You're getting off humping the bed, Ben," Dean said. He sounded breathy and slightly distracted, and Ben wondered if he was jerking off. He hoped so.

"May I... May I cum, sir?" he asked, so close that he wasn't sure he could hold it in before he heard Dean's answer.

"Oh god, Ben, you're coming? God, cum, Ben, cum now, cum all over your towel as you hump the bed mmm..." Dean growled, trailing off at the end in a series of low grunts.

Holy shit, did Dean just cum? His own orgasm ripped itself from his cock like the cork on a champagne bottle. His moans were too loud, but he couldn't stop himself from moaning or from humping the bed.

Ben collapsed on the bed, his hands still in place. He realized a second too late that he just smeared his own cum all over his belly. Dean would like that he did, he decided. His spent cock twitched lazily in agreement. He lay there, draped on the side of the bed, waiting for Dean to release him.

His breath was back to normal and Dean still hadn't spoken. "Dean?" he asked, worried they'd disconnected, or worse, that Dean had hung up on him.

"Ben," Dean said, sounding dazed. "You did a good job."

"Thank you, sir," he whispered, his face burning again.

"Clean yourself up and go to bed. You have a busy day tomorrow," Dean said, sounding back to normal.

"Did you..."

"What's that?" Dean asked, warning in his tone. "Did I what?"

"Nothing, good night, Dean."

"Nite Ben," Dean said. There was a brief pause, then his phone disconnected.

He cleaned himself up, proud of himself at having pleased Dean, nearly sure he'd made him cum.

The rest of the week was so busy with the conference and after parties disguised as networking events that Ben wasn't able to talk to Dean again. It wasn't that he didn't want to, he passed out each night from exhaustion just to get up early and start the whole thing over again. The conference ended just after lunch on Friday, and he was on the road as soon as possible.

He wanted to speed, wanted to shave minutes off of his drive to get back to Dean, but he didn't. He hit afternoon traffic, which ended up turning the last hour of his drive into the last two hours. Finally, right around six, he parked his car on the street half a block from Dean's apartment. He sent Dean a text and headed towards his building. A slow saunter turned into an excited jog, and he kinda sorta felt like a dog excited to see his master.

Dean met him at the glass security door. "What would you have done if I wasn't home?" he asked, lips pursed to the side.

"I hadn't thought that far ahead," Ben admitted.

Dean rolled his eyes, then ushered him inside. The first small flakes of snow had begun to fall, the first of the year. "Can't believe it's snowing," Dean complained, hugging his arms around him as they climbed the steps.

"Seems early," Ben agreed. "Why don't we take the elevator? You always take the steps?"

"Yea. Elevator's real old, and it breaks occasionally. Also, kinda sounds like one of the chains might be loose, it scrapes on the roof of the elevator and makes me nervous. I only live on the third floor, it's fine."

"Oh. Okay." He followed Dean quietly until they reached his apartment. Dean stepped to the side to let him in, then closed the door behind them both.

Why was he so nervous? Though nothing changed, the talk about their kinks, the phone sex, it made him feel different. Did Dean feel the same way?

Dean kicked off his shoes and headed towards the kitchen. It looked like he was watching anime, a boy with impossible burgundy hair stood akimbo on screen, looking angry. "You hungry?"

"I could eat," he agreed. "Got stuck in traffic, I'm gonna hit the bathroom."

"Do what you want," Dean dismissed.

This wasn't going the way he'd imagined it. His half a hard-on agreed. The last hour stuck in traffic was pure torture, both in the stuck in traffic way and in the maybe gonna have some fun sexy-times when I get to Dean's kinda way. It took him a few moments to get soft enough to pee, despite the urgency his bladder was communicating to him.

Dean was still in the kitchen when he emerged. "What's for dinner?" He leaned over to see what Dean was working on.

"Nothing special," Dean dismissed. Something crackled in the pan. "Just making chicken burgers."

"Oh, that sounds delicious," Ben said. His stomach growled in agreement. "Can I help with anything?"

Dean gave him kitchen busywork, and the two of them worked in silence. He tried to start a conversation a few times, but they had this weird tension between them. He'd finished his burger before he was able to say anything.

"You okay?"

"Huh?" Dean asked, putting his half-eaten burger down.

"You seem... Did I do something wrong? Should I have not come?"

He didn't know Dean well enough to know how to read his facial expressions. "No, it's fine. I figured you would."

"Why are you upset?"

"I'm not upset," Dean dismissed.

"Oh. Okay. If I did something-"

"You didn't," Dean cut him off. "I'm just..." He sighed. "You... I'm sorry, about the other night. I get outta control with you."

"About the other? What are you talking about? The phone sex? Jesus, not this again! I thought we were past this!" Dean cringed, his cheeks rosy. Ben sighed. "Dammit, Dean, I really liked it. A lot! Stop worrying about that. We have a safeword, I promise you I'll use it if I don't like what we're doing."

"You're just so submissive," Dean complained, picking the sesame seeds from the top of his bun. "You never balk. I worry that you wouldn't say anything ever, cause you're so submissive."

Ben sighed, then leaned back in his chair, running his hands through his travel-messy hair. "Dean, I'm not submissive. Not at all. I've never been like, never felt, I dunno. Like, I don't like pain, but the idea of you punishing me is hot. I don't, I've never done anything more than vanilla before you."

"I'm sorry," Dean said, the top of his bun quickly becoming a war-torn battlefield.

"Stop being sorry for this," Ben said. "I'm trying to tell you, I like it. A lot. You've opened so many doors for me that I didn't even know about, made me feel ways I've never felt before."

"It's bad enough," Dean said as if he hadn't heard a word Ben had said, "that you're flirting with being gay, but to add in the whole BDSM thing? I'm the worst. I can't control myself around you." His bun was losing major real estate, a small pile of toasted crust piling up next to it.

"Then don't!" Ben insisted. "I don't care what it's called, what we're doing. We're doing the 'Dean and Ben' thing, it doesn't need to be more than that. You've never forced me to do anything I didn't wanna do, Dean. I promise you."

Ben got up, then took Dean's hands, sparing the spongy insides of his bun from any more torment. He pulled Dean up, then hugged him hard. Dean resisted the hug, then gave in with a deep sigh. "You're killing me, DeLuca."

"Love you, too," Ben replied.

They stood there like that, arms wrapped around each other, for almost a minute before Dean broke away. Ben let him go, but reluctantly.

Dean stepped back. "You wanna watch TV or something?" He studied his feet, wringing his hands nervously.

"You're done?" Ben asked, nodding towards the burger Dean had picked into little pieces.

"Yeah," Dean agreed. He took Ben's hand sheepishly, then led them back to the living room.

"What're you watching?"

"One Piece. We don't have to watch that, we can watch Firefly or something," Dean said, grabbing the remote and backing out of the show quickly.

"We could've watched that, I don't mind."

Dean shook his head. "No, let's keep watching Firefly, then we can watch the movie, yea?"

"Yeah, sure," he agreed, disliking the tension between them. He didn't want to watch TV, he wanted to talk things through some more, but he didn't want to push Dean too far. They'd take this in baby steps. At least he felt like he was making some headway.

Dean put on Firefly, they were on the episode where Jayne finds out there's a whole town named after him. Halfway through the episode he scooted his way across the couch until their thighs were touching. Dean didn't pull away, and then he couldn't pay attention to anything but Dean's body cues.

Slowly, as if not to startle a feral cat, he lay down, his head on Dean's thigh. Dean tensed, then sighed and relaxed into it. For a split second, though, Ben was worried he was going to bolt. After a tense minute Dean's fingers began moving through his hair, and he knew everything was okay.

Still, though, he couldn't pay attention to the show. He closed his eyes, focusing on the feel of Dean's fingers through his hair and over his scalp. Ben put one hand on Dean's thigh, testing the waters, and Dean flinched, but quickly resumed his petting. Over the next few minutes he slowly slid his hand up, then slipped it towards Dean's crotch.

As he slid his hand ever so slowly he noticed Dean's legs parting for him, just as slowly. Encouraged, he slid his hand deeper until his knuckles hit something firm. Dean grunted softly as Ben stroked the solid bar in his pants, his fingers now flexing in pleasure.

Ben looked up but Dean was laser focused on the TV. Moving to his elbows for a better angle, he dragged his knuckles up and down Dean's length, tracing it through his track pants. He went too low and pressed down on Dean's testicles and Dean grunted softly. Ben pulled his hand away quickly.

Dean caught his hand and brought it back. He pried Ben's fingers open with one hand and then pressed it against his member. How could he ignore such a direct request? He traced Dean's length with his fingers, but he wanted to feel it directly. He shifted to get a better angle, then dipped his hand into Dean's pants.