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DC Rarepair Rumble (Rarer Edition) Round 2, Part 23
James Jesse/Leonard Snart
Jason Todd/Rena
Voting ended onAug 6, 2025
propaganda:
James Jesse/Leonard Snart:
First things first, the thing everyone knows, James canonically honeytraps Len and Len isn't even that mad over it.
Kings of being weird about each other. Len names James as one of the Rogues he likes best, James is about to throw hands with Len's sister in a crowded cinema when she implies she might have hurt him.
James is one of the few people who can get away with calling Len "Lenny", and one of the few people who can get away with making cold puns around Len, and one of the few people who can get away with calling Len "Mister Freeze" (although he was disguised at the time), and one of the few people who can get away with inviting the Flash to Len's "congratulations on getting out of the Suicide Squad alive" party. Honestly the amount of times Len has been legitimately mad at James can be counted on one finger, even though he does A Lot All The Time to deserve it.
James spread calling Len "Lenny" to Catwoman. Catwoman says that she met Lenny "in New York" when she was being annoyed by James, which implies that Lenny went to pick him up when he was done, because Lenny was not in those issues. Lenny says "yeah, you were getting chummy with the Trickster" with jealous body language and then proceeds to show absolutely no romantic interest in Catwoman whatsoever. What this could mean is a mystery.
They were the first Rogues ever to team up, and after they agreed to they were chummy for the entire issue, it was genuinely so cute. Given this status, it is also interesting that when Geoff Johns split the Rogues Len was the leader of the Crime Rogues and James ended up leading the Reformed Rogues (there could be homoerotic tension here, I believe, they need to have fucked in the FBI offices over it).
Jason Todd/Rena:
THEY WERE CUTE AND I MISS THEM. Also I miss Jason having people that weren’t associated with a different bat first
Additional Tags: Car Sex, Outdoor Sex, Anal Sex, Anal Fingering, Crossdressing, James Jesse dressed as Trixie, Porn with Feelings, Crossdressing James Jesse
Word Count: 1,149
Summary:
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.
How had he ended up here?
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Based on This Post by @brainwavejrsoldermankink (and for them) and for Day 6 of @kinktober-2025 prompt "Outdoor Sex" (kinda sorta)
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.
He supposed maybe their little chat would have to wait after another stint at Iron Heights.
