CHAPTER TWO
Jimmy walked back into the room as he shoved his phone back in his pocket. "He'll be here in 30."
"Minutes?" Dean squeaked. He coughed and cleared his throat. "We're doing this tonight?"
Jimmy looked hesitant. "Is that not okay? I can call him back."
Castiel sighed and placed a finger over Dean's lips, earning a glare. "That's fine, Jimmy. Dean will talk himself out of it if we wait."
Dean nipped Castiel's finger lightly before puffing out his lower lip in a pout. "Dick."
Cas shook his head and unfolded himself from the bed. Dean could all but see the Dom roll through him as he approached Jimmy. "What do you need?"
Jimmy blew out a short breath and ran a hand over his face. "Water for sure. Juice is good but I prefer a sports drink if you have it." He raised his eyes to meet Castiel's. "I'm a fan of chocolate after too."
Cas tilted his head back in thought. "I can offer you most of those. I believe we're out of chocolate."
"Chips!" Dean interrupted. He had to swallow hard and tilt his hips to avoid showing the erection he started sporting when those twin sets of blue eyes locked on him. "We have chocolate chips. I bought some to make cookies."
Jimmy's eyes danced with mirth as he flicked his gaze toward Dean's crotch briefly before winking. "That's acceptable."
"Do not encourage him," Cas said to Jimmy as he bit back a grin.
Jimmy only licked his lips. "He knows it'll never happen, dear brother. But he's fun to tease."
To Dean's absolute horror Cas began nodding. "You have a point. I'll have to keep that in mind. I'm sure he'll earn a punishment at some point."
Dean would deny the whimper that left his lips until he died. Shit. Like Castiel's sex voice doing regular dirty talk wasn't enough? The next time Dean wasn't allowed to come he'd have to listen to twin fantasies? Fuck.
Dean cleared his throat again. "So, what, uh, what's the plan?"
Jimmy leaned on the doorframe and checked his phone for the time. "This guy knows all my buttons. My hope is that you'll see it's okay to like some of the more intense stuff. And maybe seeing it in person, with someone you trust to not lie to you, will make you more comfortable. Who knows? Maybe you'll walk away with an idea or two."
Dean frowned. "And you're cool with this? Just inviting some guy over and letting him hurt you?"
Jimmy shook his head. "He's not just some guy off the street. We scened regularly when I was still doing it."
"I thought you didn't fuck the same guy twice," Dean said.
Jimmy opened his mouth to answer when a knock sounded at the door. He shut his mouth and went to answer it.
Dean scrambled off the bed. It was his apartment after all. He should have some idea in the kind of people being given his address.
He stopped short when he realized who was standing in his doorway holding a duffle bag and wearing a shit-eating-grin.
"Benny?!" Dean exploded.
"Wait, you two know each other?" Jimmy said in between giggles.
"We work together," Benny confirmed.
Castiel leaned against the wall and smirked. "You didn't say anything."
Benny rolled his eyes and dropped the bag on the floor. "Because 'hey, your boyfriend looks like this guy I used to whip and fuck sometimes' is a real great icebreaker."
"I didn't know you were into this kind of stuff," Dean mumbled.
"It's not exactly a work topic, cher. I had my suspicions when you came in sportin' that nice collar of yours but it wasn't my place to say anything."
Jimmy turned his baby blues on Dean. "You're still okay with this? I would have asked if I'd known."
Dean shook himself and smiled. "I'm surprised but it's cool. It's actually better. I trust Benny too so it's not some random dude in here."
Benny turned to Jimmy. "Boxers. Move the table and wait for me in the living room."
Dean watched as Jimmy ducked his head in acknowledgment before hurrying off.
"Normally I gag his smart mouth but it's been awhile so I want him to be able to safeword easier." Benny shifted his eyes toward Dean. "And I don't like to freak out newbies."
Dean couldn't find it in himself to be offended at the accusation. He was a newbie comparatively speaking and he was a little freaked out.
Cas took Dean's face in his hands. "Your safeword works here tonight as well. If you're uncomfortable do not hesitate to let me know." At Dean's nod he placed a kiss on his forehead. "Go wait for me on the couch. I want to chat with Benny."
Dean stumbled into the living room, glad to be instructed to sit before he fell. He made eye contact with a grinning Jimmy as his ass hit cushion. Jimmy shot him a wink as he raised up on his knees and placed folded hands behind his head. He almost looked like he was getting arrested but Dean could see how the position showed off his body.
He made a mental note to try it next time he was alone with Cas.
Benny and Cas entered the room and Dean made a split second decision to toss a pillow on the floor before kneeling. Cas settled onto the couch and ran a hand through Dean's hair with a pleased sound that wrapped around Dean like a blanket. Out of the corner of his eye, he caught the look of approval that Benny shot Cas.
Jimmy trained his eyes to the floor but didn't stop the grin that spread across his face.
"Been a long time, Jimmy," Benny's deep voice rumbled out.
"Yes, sir."
"Do you remember your safewords?"
Jimmy nodded. "Red to stop. Yellow to slow down. Green is good."
"Arms down." Benny reached into his bag and brought out a flogger. He trailed the leather pieces over Jimmy's shoulder, smiling when Jimmy hummed and leaned to expose more skin.
"Did you miss me, cher?" Benny asked as he continued to pet Jimmy with the flogger.
"Yes," Jimmy whispered, his eyes closed.
"Stand up."
Jimmy obeyed, huffing lightly as he pushed to his feet. Benny let him have a moment to shake out his legs and regain blood flow. At Jimmy's nod, he began to flick over his skin with the flogger.
Dean watched, entranced. He had no idea how Benny could be so precise with something that covered so much area with each blow, but he could tell the man was avoiding sensitive areas like Jimmy's spine and kidneys.
After several passes, the sound of leather hitting skin intensified. Dean could hear the pattering pick up as Benny used more force.
Jimmy was swaying in place. He made little punched out sounds of pleasure each time the flogger connected with his skin.
"Warm?" Benny asked.
"Green," came Jimmy's reply.
"We don't have my bench here so you'll have to bend over the arm of the couch."
Jimmy nodded in a dazed way as he moved into position. Dean could see his eyes were already a bit glassy with pleasure and he looked utterly relaxed. He folded himself along the arm of the couch, arms outstretched enough to grip the edge of the cushion. His head tilted to one side and Dean could see his eyes blinking in a slow pattern.
Benny stepped behind him and placed one hand at his lower back. "Can I go ahead and remove these?"
"Green," Jimmy replied.
Dean tilted his head to look at Cas with an eyebrow raise. Cas only shook his head and tapped a finger to his own lips to indicate they were to stay quiet.
The sound of skin slapping skin brought Dean's attention back. Jimmy groaned long and low as he melted further into the couch. The sound of each spank Benny laid out was loud and Dean could tell he was hitting with quite a bit of force.
Each spank was followed by a gasp and groan from Jimmy. His body would tighten with each blow before relaxing again.
When the whimpers began, Dean realized he was hard. Motherfucker. He was getting off on watching his friend beat on his fiance's twin brother.
Next up, on Maury.
Benny ran a hand up and down Jimmy's spine a few times like he was soothing a skittish horse.
"Please," Jimmy rasped out.
Dean's brow furrowed in confusion. Please what? No one had asked anything.
But when Benny moved to the bag Dean realized no one had to. Jimmy said he and Benny had scened together several times. Dean bet Benny could read Jimmy like Cas read Dean.
Benny returned with a coiled length of supple leather in his hands. Oh, a belt. He was folding a worn leather belt in half.
"Ten," Benny said as he dragged the belt down Jimmy's spine. "Count."
The sharp crack that split the air made Dean jump. The harsh gasp it pulled from Jimmy made Dean want to jump up and rip the belt from Benny's hands. . .
Until the man across the couch moaned. "One."
The air stilled in Dean's lungs. Holy fuck. Jimmy liked it. He fucking liked it. There was no way he was faking that pleased as punch moan.
Dean didn't realize he'd stopped breathing until Castiel's hand came down on the back of his neck. He sucked in a fast breath and let it out audibly enough that Cas relaxed.
They were up to six and Jimmy was all out humping the edge of the couch. Dean had a fleeting thought of wishing they'd put down a towel.
Seven and eight cracked down in rapid succession and Jimmy said the numbers on a sobbing moan.
The moan after nine had Dean's hand flashing down to grip his cock to relieve some of the pressure. What were the odds that Cas would let him run to the bathroom and jerk off? The brief hint of pressure at the back of his neck said his Dom knew what he was thinking.
He was so caught up in his horny thoughts he almost missed the final crack of belt across skin. He couldn't, however, ignore the shout of "TEN!" followed by harsh breathing that came from knowing you weren't going to get to come that night. Dean knew that pattern quite well.
"Dean," Cas said quietly. "Please go to our room and get the aloe gel for Benny."
Dean didn't hesitate to comply. He leaped up, as much as he could with his raging hard-on, and raced to their room.
The gel stayed in the side table with the lube and toys for easy access so it was a quick grab. He made his way back to Benny and stopped dead in his tracks.
Jimmy's poor ass.
Wordlessly, Dean handed over the gel as he stepped closer. Benny moved enough for Dean to survey his work while still staying close enough to tend to Jimmy.
Jimmy's entire backside was a brilliant red. Dean could see the crisscrossing welts from the belt along with a few finger outlines along the edges. Dean leaned in the best he could but he couldn't find any bruising or bleeding. Damn. Benny was good.
Jimmy whimpered and writhed as Benny applied the gel with gentle motions and whispered praise. Dean went to the kitchen to help Cas get recovery snacks. He felt like he was intruding on something.
Cas greeted him with a gentle kiss. "Doing okay?"
"Is Jimmy gonna be okay?" Dean whispered.
Cas smiled. "He'll be sore and he might have some light bruises but he's fine." He handed Dean a bottle of sports drink before rooting around in the pantry for the chocolate chips. He poured a few into a small bowl and gestured for Dean to lead the way back to the living room.
Benny was seated on the couch with Jimmy curled in his lap covered by a blanket. His hand ran rhythmic circles on the dark haired man's back. Occasionally Jimmy would make a small contented noise and nuzzle into Benny's neck.
Dean handed him the sports drink while Cas put the bowl of chocolate on a side table. Benny accepted both with a head nod and grin.
Jimmy started to rouse a bit with the new presences. Benny helped him sip the drink before hand feeding him individual chocolate chips until he was more aware. The two shared a few sweet kisses that made Dean blush.
Jimmy blinked slowly at Dean. "You okay over there, Adonis?"
"I think I should be asking you that," Dean replied.
Jimmy stretched and sighed. "I'm awesome."
Benny dropped a kiss to his neck. "Do you have someone to drive you home?"
"He's staying here tonight," Castiel interrupted.
Jimmy shook is head with a smile. "You heard the Dom."
"You know the drill," Benny said.
"Call in the morning and text throughout the day." Jimmy stood slowly, keeping the blanket wrapped around himself.
Benny cupped his face in a large hand. "It's been a while. I don't want you to drop too hard, cher."
"Thank you," Jimmy whispered as he leaned in for a kiss.
Cas walked Benny out while Dean helped Jimmy get set up in their extra room. He worked in silence, unsure of what to say or how to organize his thoughts.
One thing kept replaying in his mind, however.
He wanted to try.
