James was sure he would need to redo his nails after this. He could already picture the chips in the red polish at the tips of them from the way they were digging into the leather of the car seats. His pantyhose were hanging around his ankles while he could feel the stubble along Len’s jaw rubbing up against the inside of his thighs. 

He was hard, his skirt hiding none of it. And from where his leg was being pushed up into Len's crotch from the awkward position in the back seat of the car, he could tell Len was just the same. 

The leather creaked under them as Len moved up from between his legs. Lips found their way to his neck as his skirt was hoisted up and Len’s finger rubbed at his entrance. 

A moan louder than he anticipated came out of him.

How had he ended up here? James had just wanted a nice night out. Nothing big, just a nice dinner to treat himself. The only thing in the way was being recognized as James Jesse The Trickster. Ergo; Trixie was pulled out of the closet! 

A dinner planned for him alone, everything was set for a nice evening.

Until he ran into Len in the restaurant's parking lot. And for the first time since all those years ago, he regretted tricking Len with Trixie. 

Lisa, double date, Len had said. The lack of a date on his arm was the dead give away too.

One fake date later—that he was sure Lisa and Roscoe both recognized him—one thing led to another, he and Len had broken into a random car in the parking lot with a backseat they had deemed big enough and well…

“Cold…” he moaned out, as Len's finger pushed past his rim. He'd find the irony of it later considering how freezing Len's hands were as ever. Should have been a turn off… as if he wasn't getting harder by the second just feeling each and every touch of his hands on his body.

The hand that was curled around his thigh tightened, pulling his legs open wider. Len’s hips were rutting into James’ still awkwardly bent knee, the pace matching as he started pumping his finger in and out of him. 

His moans grew louder, he started to pant with every finger Len pushed into him. The leather seats creaked further under his grip as he braced himself.

James wanted to tease. Throw off some quick one-liners to mess with him. But he found himself out of any taunts or anything quick and witty; his mind a haze and his patience wearing thin.

“Lenny,” he panted, “hurry.”

Before he knew it, the friction from his fingers was gone. There was the sound of a belt and zipper being undone, then his leg was being thrown over Len's shoulder. He threw his head back with a deep moan, the pressure building as Len pushed into him.

James forced out a breath, trying to breathe evenly. He heard a groan from Len. The hand on his thighs tightening. His pantyhose was digging into his skin as his ankles were forced apart but kept close together by the garment.

He didn't have to beg anymore for Len to start moving. Something slow progressed into something faster and faster as quickly as he could. James pressed down with every thrust, quickening the pace, wanting more. He couldn't control himself anymore, moaning with every movement. Len’s name on his tongue with every breath.

“Len—lenny.” He reached for the hand resting on his leg not thrown over Len's shoulder. “Please. Please, Lenny.”

He pushed into him harder.

James knew his wig was going to be a hassle to detangle later, probably needing to be washed as well. Every item of clothing he was wearing would need to be washed with the way his cock was leaking, pinned between him and Cold. He needed some type of friction. Both of his hands were busy marking up the leather, and both of Lens’ hands were busy holding his legs in place as he pounded into him.

He arched his stomach forward, pressing his cock to touch his and Len’s chest. He loudly moaned in pleasure from the needed friction. No surprise if the whole parking lot and restaurateurs were hearing every second of it. 

“Cold,” he whined, shamelessly. “Lenny. Len, I need you.” He wasn't going to last any longer. ”Please, Lenny… please, I'm gonna—im gonna, Len—”

He could hear his moans bounce off the interior of the car as he came, practically shouting for anyone to hear. His abdomen tightened; spasming as Len continued to pound into him. Every muscle from his finger to his toes tingled and burned.

Len came with a deep groan, riding his orgasm out inside of him with small little thrusts till he stopped.

Their panting filled the car. Still pressed up against each other till Len pulled out. James could feel how wet his thighs were as everything began to cool. His own come a mess on his blouse, skirt, and Len’s shirt.

James dropped his hands and looked down at his candy red nails. Not chipped. 

He looked up at Len, who was breathing less heavily than a minute ago. Eyes looking over his face, looking speechless. Not many things could leave Len looking like that.

Len looked down, making James feel more naked than he realized he was. Seeming to take notice, Len shifted, smoothing down his skirt first before tucking himself back into his boxers.

“Thanks.” 

Len hummed, avoiding eye contact. Looking anywhere other than the scene of what just happened. He shook his head and sighed. “Look, James—”

And he expected a quick rebuttal, an excuse, or a promise that this never happened between them. All things he was prepared to handle. It was Len after all; mister no feelings, and no sentiment. He was surprised that the gentle James he spoke wasn't just a curt Trickster and an unspoken this never happened.

He didn't blame the guy, considering what his and Lisa’s childhood consisted of. Still, he knew Len cared in his own way through his rules and tough love. James would be lying if the semblance of family he had with the Rogues wasn't one of the reasons it made it so hard for him to stay reformed.

Sure Len was rough around the edges with miles long rough of trauma, but weren't they all? Len was always nice on him compared to the others. It had been them two to begin with. One team up one day out of chance. 

Besides… it's not that Len was bad looking. Maybe they could talk about things. Right? 

Then came the knock on the window.

“Ready?”

The rod pressing up against the head of his cock was cold. Both things were slathered in an obscene amount of lube. Something Adam said was necessary to help guide it easier and make it less painful, even though he reminded him pain wasn't a factor in this for him. Still, he insisted.

The heart in the vessel he was in was drumming faster and faster. Nervousness and arousal, both key factors as he further assessed the situation. Adam was sat on his knees between his splayed legs completely clothed; while he laid bare naked on the bed, with his half erect dick in Adam's hand and a metal rod in the other.

He would refuse to feeling nervous, if only that meant he could too refuse knowing what arousal felt like. Something at one point he didn't, but now, Adam was teaching him well.

He looked at him. Adam cocked an eyebrow, waiting for an okay to shove the rod down his urethra. The metal cage that the rod belongs to sat on the bed next to them. He wanted him locked back up, at all times; something Michael hadn't protested, but still refused to admit enjoying.

A twitch from his cock at the thought let him know all he needed to know. He cleared his throat as Adam smiled down at the twitching dick in his hand.

“Okay…”

“What was that, Michael?” He pressed the rod harder against the tip. 

Michael stifled a groan as he squirmed and gripped at the sheets. 

“Yes.”

Adam repositioned his hold. “Take a deep breath for me.”

“I don't need—” He hissed as the rod was pushed a bit of the way in. The sheets bunched up under his hands, slipping under his heels as he kicked. Pressure built amongst the discomfort, masking the new feeling and sensations.

“What were you saying?”

Adam cocked his head, acting innocent as he pulled on the sound. He moved his dick then pushed it further in.

Michael let out a keening noise, not failing to feel how aroused he was getting with every little movement.

“The harder you get the more tough this is going to be to get in.” 

Coldness spread across the tip of his dick. Lube spread more as the sound was tugged back again then pushed, sliding in deeper, making him feel full. He groaned, thrashing more as Adam held everything still and shushed him gently.

His chest felt tight, not from the discomfort, not from pain. He felt small, weak; nothing he was used to feeling. Something he’d only felt next to his father.

“Adam.” He bit back a cry. The pressure continued to build, a lump in his throat formed, his toes snagged on the sheets as he couldn't stay still.

“You’re okay. Just a bit more.” He spoke gently. 

And gentle words or not, Michael couldn't shake that building feeling slowly turning to panic. “Adam!” 

“All done.” 

Adam kept one hand holding his cock, and used his free hand to grab his. He rubbed his thumb on the back of his hand as Michael took ragged breaths.

“Good?” He checked in.

He nodded. Still wanting.

Adam slowly started to move his hand around his dick. “Full for me, Michael?”

A small whimper was the only thing that came out of him as he gripped Adam's hand tighter.

“Do you want to come?”

He nodded more frantically. “Please.”

Adam stopped and reached beside him. The ring of the cock cage in his hand as he put it around his dick and started fitting his balls through.

“Adam, please…”

He didn't answer. Instead, once the ring was secured, he raised the metal cage and pressed it to the head of his cock. Michael gasped as he pushed down. The cool metal doing its job, his erection went down enough for him to hold the cage in place and intact.

“Good boy.”

Michael bristled. And watch as the key was raised up between Adams fingers. He made a show of locking it, giving it a few tugs before he looked satisfied with his work.

Michael took a few deep breaths. Something calming and grounding as he reached for Adam again. His needs were met and more as Adam climbed over and laid beside him. 

Adam reached down, taking his caged dick and balls in hand, fondling them. 

It had been David’s idea first.

David would argue that entire argument to his grave. 

In reality, it had started as a joke when David had asked Hartley what he wanted for his birthday.

A threesome with you and Trickster.

They had both laughed at the time. Their relationship was open, not that either of them did much stepping out of it to begin with. Still, they both liked the idea as much as the threesome with Trickster was just that—

A joke. 

Well… after all, jokes were James’ thing.

Hartley could hear the subtle creaking of the bed with every thrust as David pushed into him. Normally David liked to be gentle with him, treating him like something delicate, something he had teased him about but otherwise found endearing about the man.

But normally James Jesse wasn't lying in bed with them either.

He rocked forward with every thrust, a hand gripping his hips, hearing David's every breath and groan as he took him deep, fast, and rough. All the while he took James’ cock deep to the back of his mouth. The same cock he had thought about and stared at through those striped spandex pants all those years.

Not that he'd ever have admitted it. James was his best friend.

His best friend who he had watched get fucked by his fiance not fifteen minutes earlier. 

Again, as much as he loved David’s gentleness, he couldn't argue that his soon to be husband ordering, and yanking them both around wasn't going straight to his dick.

The way all of James' jokes and quips turned to nothing but unintelligible moans. Being forced to his knees first thing through their bedroom door so that he could suck David off. His own saliva used as lube as David bent him over their bed and used him. 

Both he and James were left wanting as James was left hard, half fucked, and naked on their bed. All the while, Hartley was hard not even a minute into watching as he used his hand for some relief. Then it was his turn.

Stripped the rest of the way down and forced to his knees to taste what was left of Trickster off David's cock. He was there just for a minute before he was guided to Trickster's dick and David was pressed up behind him.

Best of friends.

He felt the hand on the back of his head grip his hair tighter. He took a sharp breath out through his nose as he was forced down. James pushed his hips up, a loud moan coming from him as he hit the back of his throat. He groaned around his dick, watching as James threw his head back. David pulled out before pushing himself back in at an angle, making him moan more which only sent James over the edge as he continued to hit the back of his throat.

“Piper… Hartley.”

He came first, followed by Trickster not two seconds later, then finally David. His legs shook, he knew his knees, throat, and who knew what else would be sore soon. For now, he enjoyed the haze, the warmth from James and David, and the panting coming from both of them.

The thrusting slowed to a stop, just as the hand gripping his hair gently pulled. He was lifted off James' dick, his tongue running up the underside, leaving a fresh trail of saliva and cum. He took the opportunity to catch his breath, his mind too fuzzy to think to do anything else.

James' hand relaxed, carefully rubbing the area where he had been yanking. He felt David doing much the same, caressing where he had been grabbing his hip; probably hoping he wouldn't leave a mark even though Hartley wanted the exact opposite.

He looked up, seeing crystal blue eyes slightly covered by his mess of tousled hair—courtesy of David. He collapsed on the bed. The bedsheet was used by both James and David to clean him up. His chest and mouth wiped clean before they left him to catch his breath.

The tickle of kisses being pressed to his spine brought him back, and made him smile. Trickster rubbed his scalp as another kiss from David found the shell of his ear with a whisper.