Ben Loves a Challenge Ch. 16

"Thank you, Sir!" he gasped as Dean's finger sank deeper. He worked to relax, then those clever fingers tickled over his favorite spot and his knees nearly buckled.

"Stand still, bitch," Dean barked, then buried his face between Ben's cheeks again.

"Yessir," he mumbled, focusing on the point of pleasure that was Dean's finger tracing over his prostate. Dean pressed down harder and he moaned. Kisses landed all over his ass cheeks as Dean's finger stroked his prostate. He closed his eyes again, sinking into the sensation. Dean's kisses were frequently interspersed with nips, though none as hard as the bite on his shoulder. It still ached, reminding him of exactly where it was, and who put it there.

He wanted more, more and more of Dean. "Please," he begged.

Dean pulled his finger out and he whined. "Hush," Dean chided right before pushing his tongue in Ben's slightly relaxed hole. Ben moaned as Dean began sucking and licking his most intimate place.

"Yes... yes... yessss..." he moaned, spreading his legs as wide as he could while standing to give Dean better access. "Fuck yessss."

"You like this, bitch? Me rimming you?" Dean dipped his fingers in Ben's ass while he spoke.

Ben thrust his hips back on Dean's digits. "Yes, Sir, I love it."

"You like having your ass rimmed? Aren't you supposed to be straight?"

Ben moaned when Dean started peppering his ass with kisses again, silently wishing that he'd bite him hard. "I am straight, I'm only gay for you," he said, the words punctuated with his pleasured gasps. Dean rewarded him with a bite on his left cheek. It wasn't as hard as he wanted and he whined. "Never knew..." he paused when Dean evened out his bites on the opposite cheek, "that I'd love having my ass eaten. Fuck, Dean. Sir, fuck. Bite me harder, please, Sir. Please bite me harder."

"How'd I get so lucky?" Dean murmured. His teeth sank into Ben's left cheek and he grunted at the pain. The other cheek quickly got the same treatment. "You want more bites, or do you want me to eat your ass some more?"

"Both?" he begged.

Dean chuckled. "You're so greedy. You have to pick one."

He whined. "Um..." It was so easy to say a minute ago, but now it was hard. "Eat, um. Please, sir, um, eat my ass?" The last part was just a throaty whisper, the loudest his embarrassment would allow.

"Good boy," Dean praised. He buried his face between Ben's cheeks and lapped at the puckered skin around his fingers as he thrust in and out.

Ben's knees were weak with pleasure, and also the position he was in, legs spread wide, hands resting on the side of the tub so that his ass was high in the air. Dean's tongue pushed into his hole as his fingers spread him wider and he swayed, almost falling. Dean caught him, his fingers and tongue disappearing instantly.

"Sorry Sir," he whispered, feeling like he'd ruined it.

"Shut up bitch," Dean chided. "Go to your room."

Ben nodded, standing up. He had to step in place a few times to get his legs to unfreeze before he started towards his room. Dean cleared his throat loudly. "Sir?"

"Like the bitch you are," he said. "On all fours." One finger pointed firmly towards the ground.

"Yessir," he said, gasping when Dean's hand landed smartly on his ass, stinging from the quick impact. He dropped to his hands and knees and pushed the bathroom door open, then headed for his bedroom. Dean followed behind him and he nearly died of shame knowing what he must look like to Dean, but also wanting Dean to see him like this.

"Up on the bed," Dean commanded when they got to his room. "Head down, ass up."

He moved quickly into place, then shivered as he waited for Dean to move. Dean let him wait. "Sir?"

"You'll stay like that for as long as I want you to," Dean said. "I'm admiring the view."

"Yes, Sir. Thank you, Sir."

Dean chuckled. "Don't thank me yet," he said, another sharp smack to Ben's other asscheek. He wondered if Dean had left hand prints. He spread Ben wide and plunged his tongue inside him again, his eager licking and sucking melting Ben's mind.

"Sir," he moaned. Dean pushed a finger inside and he moaned again.

"Like a bitch in heat, Ben. You're such a little slut, the way you're pushing your ass back, practically begging for another finger."

"Please, Sir, another finger," he moaned, his mind catching on those words.

"You're not loose enough for three yet," Dean said.

"I want it to hurt a little," Ben whispered. Dean paused, then pushed the two fingers inside Ben as deep as they could go before he began to scissor them. Ben writhed, thankful that he was now on the bed and wouldn't fall. "Dean. Sir, fuck..."

"I never woulda taken you for a pain slut," Dean praised. He pulled his fingers out and rewarded Ben with his tongue again, sucking and licking every inch of Ben's flesh.

"Sir, Sir," he said, panting as he rode Dean's tongue in his ass. His tongue was good, but he suddenly wanted Dean's cock, wanted to feel so full it hurt, but in a good way. "Please."

Dean pulled back, his fingers circling Ben's hole again. He pushed them in and Ben whined, he'd only used two again. Dean smacked his ass. "I'll decide what you get and when, bitch."

"Yessir," he said, the words melting together as Dean petted his prostate. "Thank you, Sir."

He grunted when a third finger pushed inside him. It hurt, he clenched down. "It doesn't have to hurt, Ben," Dean whispered, his other hand coming to rest comfortably on Ben's back.

"I want it to," Ben whispered. "I want your cock, want you to fuck me so hard."

"Then let me warm you up the right way, and maybe I'll fuck you, and maybe as hard as you want, or at least as hard as you deserve. If we don't do it right, if we rush it you could tear, then we would have to wait until you healed before we could do it again."

"Sorry," he whispered. "I just want you so bad."

"Fuck," Dean growled, hugging him from behind in a way that put his hard cock right in Ben's crack again. It felt like it belonged there. Dean kissed his back and shoulders, then his neck up to his jaw. "I want you, too, bitch. Be patient, I'll take care of you."

"Thank you, Dean," he whispered back. "Love you."

"Love you, too," Dean whispered into his ear. He caught Ben's lobe and nibbled, not hard enough to hurt. "So much." Dean stayed there for a few breaths, then pulled away again. Ben heard him moving and turned to look over his shoulder. "Lube," he said, reaching into the drawer Ben used to store what he referred to as his 'Dean stuff'.

Once Dean's fingers were lubed they slid inside much easier, and he was able to take three, though Dean took it slow. "You're so tight," Dean praised, pushing his fingers in and out of Ben's ass. "No moving." Dean held his hip firmly with his other hand and Ben whined.

Dean's evil chuckle made his dick bob. It felt wet, and when he looked down his body he saw he'd leaked so much precum it was dripping to the bed. Dean paused, his fingers as deep inside as they could go, then moved to look at what Ben was looking at.

"Oh my," Dean said, tisking again. "Look at what a mess you are." His hand snaked in and caught the long strand of hanging precum, then brought it to his lips. "You taste so naughty, Ben. Like you're desperate for cock."

Ben moaned, pressing his ass back into Dean's hand. Dean scissored his fingers and he started whining, unable to stop his hips from moving. He wished Dean would grab his cock again, but he didn't.

"Are you, bitch?" Dean asked, pulling his fingers out.

He whined again. "Am I what, Sir?"

"Desperate for cock?"

He swallowed hard, the words locked up in his throat. "Yes," he whispered.

"What? I can't hear you," Dean said, moving away from Ben.

"Please, Sir," he begged.

Dean snorted. "What are you asking me for, bitch? I won't know unless you say it right.

"Please, Sir... I..."

"Are you desperate for cock, bitch?"

"Yes," Ben gasped, his ass waggling, missing Dean's fingers.

"Say it," Dean demanded.

"I'm..." He had to swallow hard again. "Sir, I'm desperate for your cock."

"Ask me to fuck your tight ass."

"Please, fuck my ass, Sir. I need your cock." Ben heard Dean's zipper and looked back to find Dean taking his perfect, mouth watering cock from his pants. "Please, fuck my ass Sir. Breed me, please breed your bitch."

"Uh-uh-uh," Dean said, shaking his head. He reached into his pocket and pulled something out. Ben whined when he saw it, the neon pink condom from the party. "You're getting punished." He caught the edge of the wrapper with his teeth and ripped it open.

"Please, Sir, no condom!" he begged as a tremor shook his body.

"Yes, bitch. A condom. Your punishment. You don't get my cum."

Ben whined. "Please, Sir!"

Dean pulled out the condom and rolled it down his dick so smoothly it looked practiced. "Yes, bitch." Dean pulled him around and up, off the bed, then pushed him down to his knees. "Suck it, Ben. Suck my cock, show me how much you like being my bitch."

He whined, leaning forward. The smell of the latex was gross, he didn't want to taste it, but he wanted Dean's cock so bad. Wanted to be Dean's good little bitch. He hesitated too long, Dean's fingers threaded into his hair and pulled his head forward until his dick was pressing against Ben's nose.

"Suck it, bitch," Dean repeated. "Now."

He opened up and Dean thrust his member into his mouth. He instantly regretted ever having a woman blow him while he was wearing a condom, the taste of the pre-lubed condom was really unsexy. He whined and Dean pressed deeper.

"What's the matter, bitch?" Dean asked. "Don't like the taste?"

He whined again, leaning his head back as he tried to take Dean deeper even as his whole mouth filled with the chemical taste of the condom. Dean pulled back a bit and he took a deep breath with his nose, then plunged his head forward, sucking Dean back inside.

Dean's hips moved in time to his bobbing. There were so many things he didn't like about the condom. He couldn't taste Dean's skin, something he really missed right now. He couldn't taste Dean's precum, couldn't tell how much of it was spilling out of the sexy little slit across the top of his crown. He couldn't push his tongue into the slit, couldn't trace his tongue around the edge of his cockhead, couldn't feel the pulsing of Dean's heartbeat in his cock.

It made him frustrated beyond belief. He sucked Dean hard, bobbing faster because he couldn't do anything else. "Touch yourself," Dean panted, his eyes locked on Ben. "Stroke yourself as you're denied the pleasure of touching me directly."

He whined, but his hand eagerly wrapped around his burning member. He stroked himself slowly, knowing if he got off he'd be in trouble, but it was hard to move his head one way and his hand the other.

"You can't have it," Dean said huskily, rocking his hips a little deeper than before. He pulled Ben's head off his cock on the next thrust and forced him to look into his eyes. He didn't know if he could feel more sexy-shamed than he did right now, on his knees, Dean's latex covered cock inches from his mouth, dripping with his saliva as his own cock dripped with lust. "How does that make you feel?"

"Please," he moaned, his eyes moving back to Dean's neon-cloaked cock. "I wanna taste you, Sir!"

"Nope," Dean growled. "Beg me."

"Please, Sir, let me taste you," he moaned.

Dean rubbed his spit-soaked cock against Ben's cheek, making him whine again. "No. You want my cum?"

"Yes, please, Sir!"

"You're my little cum-slut, aren't you?"

He was trembling. Dean moved his cock to stroke the other side of his face, very obviously avoiding his mouth. "Yes, Sir," he replied, a tremble in his voice.

"Say it," Dean demanded, pulling his gaze up again with his hand in Ben's hair. It hurt and he wanted more.

"I'm your cum-slut," he gasped as Dean tugged his hair again. "I want your cum!"

"Good boy," Dean praised, relaxing his hold in Ben's hair a little. "But, too bad. This's punishment." He whined and Dean laughed. "Make me cum, bitch," Dean demanded.

Ben went to nod, but Dean shoved his condom covered cock back into his mouth. He began bobbing, but Dean apparently didn't like his pace, or was just too far gone to his lust that he began thrusting. His thrusts quickly grew stronger and Ben's world quickly narrowed down into the pain of Dean's tugging his hair and the nearly choking sensation of having Dean fuck his mouth.

He was so close to coming from just this. Dean rode his face, the action sexy as hell. It also made him feel sexy, that Dean was enjoying it so much, that Dean was using him. That it was punishment made it even better.

"Coming, bitch," Dean moaned. "Swallow it all." He whined in the back of his throat while Dean's thrusts grew more frantic. "That's right, you can't. Oh, fuck, Ben. Coming, so good. Suck, suck me harder, fuck, yes!" He sucked and angled his head, trying to take Dean deeper, his head pickled in lust. "Coming and you can't have it!"

He whined as he continued to take Dean's rod. He felt it as Dean came, and felt the tip of the condom swell with the cum he wasn't allowed to have. It was embarrassing how much he was whining, and how frustrated he was. He sucked harder, hoping the condom would break and spill Dean's creamy seed into his mouth, but it didn't.

Dean's hand relaxed in his hair, but Ben kept on bobbing and sucking. "Yes, bitch," Dean moaned, still lost in his afterglow. "Keep trying to get my cum. If you're lucky you might get me hard enough again to fuck your ass."

He looked up, eager to have Dean cream his ass. He hated the taste of the latex, but he felt like he could almost taste Dean through it, if he just kept sucking maybe...

Dean pulled away from him, holding Ben's head back with his fist in his hair again. "Look what you did," Dean said, sounding dreamy. He forced his drooping cock against Ben's face, the tip of the condom bloated with ejaculate. "You still want my cum?"

"Yes, please," he begged, trying to shift his head enough to suck Dean back in his mouth, the only thought in his mind was that of Dean's cock in his greedy ass. "Dean! Sir!"

Dean rubbed his wet cock over Ben's face, then pulled his head back to look at it. He tugged the condom off with his other hand. There was a squelching noise when it finally came free, and it was close enough to Ben's nose that he could smell Dean's pungent spunk. How much he wanted Dean's cum filled him with shame, made him feel like a slut, and sent a pulse of desire to his dick.

"Eat it, then," he said, offering the open end of the condom to Ben. Ben looked at it, confused for a minute.

"Eat it?"

Dean pressed the open end of the condom against Ben's lips and he licked by impulse alone. "Eat the cum you wanted so much, Ben. Eat it out of the condom."

He moaned, then thrust his tongue into the still warm sleeve that had just covered Dean's scepter. The taste of latex ruined the taste of Dean's cum, which just had him even more frustrated. Too soon Dean pulled the condom away and looked inside it, then clucked his tongue.

"You're such a greedy cum-slut," Dean praised. "Maybe I'll buy some condoms and we can do this all the time."

"No!" he cried. "Please, Sir, no! This's just supposed to be punishment!"

"Good boy," Dean praised, releasing his hair then scratching his head gently. It felt incredible. He took his hand away too soon. "Stand up."

Ben did, stretching his knees out as he did so. He looked at Dean for more direction. Dean sat down on the floor with his back to the foot of Ben's bed. "Now I want your cum," Dean said, a dreamy look of contentment on his face.

"Should I get the other condom?" Ben asked, a tremor in his tone.

Dean snorted. "Get over here, bitch." Ben didn't hesitate, he walked to Dean's side. Dean shook his head, then pulled him by his hips. "Legs on either side of me, Ben," he said, adjusting his stance until he was pleased with it. "Spread 'em." Dean's hand smacked the inside of his thighs. "Oh, wow. Look at all this precum."

Ben whined. "Sorry, Sir."

Dean smacked the inside of his thighs again, sharper this time. "Hush." Ben almost answered, then just nodded his head. "Good boy." Dean's lips closed over the tip of his manhood and his eyes rolled back in his head as his whole body swayed. "Lean forward, Ben, hands on the bed."

"Yessir," he hummed, moving into place. Dean's finger trailed down his dick and between his testicles, and he squeaked when it continued up his taint until it reached his still relaxed hole.

"This part of you is so honest," he said, dipping a finger inside. "You want me in here?" He pushed a second finger inside and scissored them.

Ben whimpered, his hips thrusting reflexively. "Yessir," he whispered, his throat tight. "Please."

"No. Don't forget, Ben," Dean said, his tone both sweet and threatening at the same time. "We still have another condom."

"No!" he exclaimed. He clamped down on Dean's fingers accidentally, but it felt really nice. "Please, no!"

"Oh, yes," Dean hummed, pleased with himself. "Not right now, I'm gonna suck you off while I plunge my fingers in your tight, greedy asshole. You want that?"

"Fuck yes, Sir. I want it."

"Beg me to suck your straight-boy cock," Dean demanded. "I love hearing how much you like being fucked by a man."

His cock danced and his asshole twitched like crazy, he was nothing but need. Dean would have him coming the second his lips sucked him deep. "I love getting fucked by you, Dean," he breathed. "I love everything you do to me. I love you so much."

Dean's hand stilled for a second. Ben opened his eyes, but he was behind Dean's head so he couldn't see the look on his lover's face. Warm lips closed around the tip of his cockhead and he wanted to push deeper, but clever fingers in his ass controlled him like a puppet. Dean snorted around his cock, then pushed his tongue into the slit and licked hard.

His knees buckled and he was grateful for the position he was in, his head and arms on the bed bracing him so that Dean had full access to his cock and ass. Fingers pressed in deeper then pulled out, leaving him gaping for a second before they returned with a third one, stretching him out. Dean's tongue wrapped around his cockhead as he sucked hard, thrusting deep into his ass at the same time.

"Fuck, Dean!" he exclaimed. "I'm so close, you're so good at this. I want you, I want you to fuck me so bad. Dean, shit, yes, oh, shit, Dean so good..."

Dean sucked hard and pulled his dick deeper into his mouth then bit down, stilling Ben's hips. He hadn't even realized he'd been moving, riding Dean's fingers. Those same fingers spread wide and he gasped as he felt himself stretched, the tiniest twinge of pain accompanied by a wave of pleasure as Dean released his bite, sucking hard.

His whole body was trembling as Dean held him still, stretching his asshole wide on his fingers. Dean pressed a fourth finger against his whole but didn't push it in and he whined. "Yes, please, Sir, fuck my asshole with your fingers, please, Sir!"

Dean groaned and pulled back, then plunged his head down Ben's length again, thrusting his three fingers in and out of Ben's asshole, hooking his prostate each time. He was coming after the fourth rotation of this, thrusting his hips against Dean's fingers as he ached for something more. His balls pulled up as he unloaded in Dean's mouth, the velvety suction narrowing down his entire world to just Dean's fingers and mouth.

He was moaning and panting, his whole body trembling as Dean sucked more and more cum from him. His hips eventually stilled and Dean pulled back, but his fingers stayed in Ben's ass. He clenched down on them, unable to stop himself. Dean went to pull his fingers out but Ben caught his hand, holding it in place.