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Red Robin let out a deep sigh before yawning and running a hand through his already messy, tangled hair. Hours of surveillance had borne no fruitful effect so far, and he was ready to call it a night. Tim had been watching Black Mask for over a week now, following the man everywhere he went and even going so far as to bug several of the man’s residences and remotely hack into his computer. He was starting to think the tip he had received stating that Roman was planning to receive a large shipment of drugs and experimental weapons was incorrect. Outside of the man’s usual shady dealings and strict nightly routine of booze and hookers, nothing seemed amiss.
He tapped into his own comms, lips parting to tell Barbara he was calling it a night when the sound of the office door clicking open caught his attention. He turned the communicator back off and snatched up his headphones, slipping them onto his head and pressing himself against the wall, trying to stay out of sight and silent as he peeked through the window. If Roman had brought another prostitute back to the penthouse, he was going the fuck home. The soft sounds of chatter filled his ears, courtesy of the bug he had placed in Roman’s office, and Tim’s heart dropped at the familiar accent even if he couldn’t quite make out the words.
He had known Jason was likely investigating Sionis as well, especially considering their ongoing cat and mouse relationship, but this was just stupid. Had he really gone undercover with no backup? If he had told Bruce or Barbara about his plan, they would have told Tim and formed a plan for the two of them to work together on this. Instead he watched with a sick feeling in his stomach as Roman sprawled himself into the chair at his desk and Jason slipped between his legs, hopping up to sit on the desk, smiling and parting his legs invitingly. Dark jeans strained across his thighs, so tight they looked painted on and he slipped his coat off to reveal a thin, loose mesh shirt that left nothing to the imagination.
Tim knew he should leave. It was obvious, even to a virginal shut-in like himself, what was most likely going to happen. But what if Jason’s plan went wrong and he needed help? He internally debated his choices. He couldn’t call for help. Even a whisper to the comms could alert Roman to his presence just outside the window and Jason would be hurt. He was distracted from his internal debate as the men inside began to speak.
“You’re special, you know. Most whores are scared of the mask.”
Jason laughed softly and Tim watched him reach out and run a hand up and down Roman’s arm.
“I was raised around here. You live in Gotham long enough and nothing scares you anymore. Besides, a powerful man has always been more attractive to me than just a pretty face.” His hand slid up Roman’s shoulder and rested gently on his neck, tugging the man closer. Jason leaned in close, a seductive smirk on his lips and his eyes half lidded.
“We both know I’m not here to talk, Sir. Tell me, how should I please you?” Roman’s gloved hand tightly gripped the back of Jason’s neck and the other trailed up his thigh, smooth leather against rough denim.
“I like a whore that knows its place. Take these off-“ He pulled at one of the front belt loops on Jason’s jeans.
“and show me what I’m paying for.”
Tim could feel his face heating with a dark blush and he bit down on his lip, eyes widening as he watched Jason nod. Roman leaned back in his chair as Jason stood and slowly turned, hips swaying as he kicked off his shoes and peeled the tight jeans down. They clung to his ass and thighs and Tim watched as every inch revealed more soft, pale skin. His breath hitched at the sight of black lace stretched tight over Jason’s hips as he peeled off his shirt and crawled up onto the desk on hands and knees, shaking his hips.
The sight was obscene in a way that had Tim’s cock swelling beneath his suit. Many of Tim’s nights had been spent fantasizing about his predecessor’s strong thighs and perky ass as he touched himself but seeing the real thing was better than Tim’s wildest dreams. He felt jealousy grip tight in his chest as Roman groped at Jason’s ass, spreading his cheeks around the thin elastic of the thong and humming appreciatively. Tim could only imagine what Sionis must be seeing now as he hooked a finger into the thong and pulled the string aside, which drew a soft shudder from Jason.
Tim’s mouth felt suddenly dry as he watched Jason’s back arch, pushing back into Roman’s hands.
“Like what ya see, Sir?”
Jason was practically purring as Roman’s hands poked and prodded, fingers rubbing at his hole before he let the band of the thong snap back into place. Jason flinched and gasped, his eyes fluttering closed. Roman chuckled and gripped Jason’s ass with both hands, spreading him wide before letting go to watch the flesh jiggle as it fell back into place.
“You’ll do nicely. I trust you’ve adequately prepared yourself already, as I requested?” Jason nodded quickly.
“Yes sir, four fingers like you said.” Roman patted Jason’s back in approval as he stood. Tim swallowed as the image of Jason, fingers slick with lube and deep inside himself came to mind. He pressed the heel of his hand into his crotch, his other hand coming up to cover his mouth and muffle his sharp breaths. He wanted to touch himself so badly but resisted, eyes fixated on the scene unfolding through the window.
Roman grabbed and pulled at Jason, adjusting his position. He ended up bent over the desk, feet planted firmly on the floor and spread wide enough for Roman to stand between them. Roman pulled off his belt and wrapped it around Jason’s wrists, which he had pulled above the man’s head.
“Grab the edge of the desk. If you let go before I say, you’ll be punished. Understand that, whore?” Jason nodded, breaths quickening as his wingers wrapped around the edge of the wood. Tim could see Jason’s cock hardening against the desk, the head peeking out of the obscenely small panties.
“Yes Sir, I understand.” Jason squirmed as Roman’s hands explored his body for a moment before he let go and stepped away, drawing a confused sound from Jason’s parted lips. Roman just shushed him and crossed the room, retrieving a bottle of liquor and a glass. He sat back down in his chair and watched Jason shift with anticipation as he poured himself a glass of the dark liquid and drained it in one go, his free hand running up and down Jason’s thigh, pinching and squeezing. Tim could hear each sharp breath Jason took and was mesmerized by the nearly imperceptible tremble of his legs.
He couldn’t take it anymore. Tim fumbled at his belt, unclipping it and shoving a gloved hand down his pants. He was already hard and leaking precum, which he used to lubricate his hand as he started to teasingly pump himself. He wanted to rush but maintained his self control, determined to make it last. His breath and Jason’s both hitched softly when Roman stood, unzipping his pants to let his cock flop out and smack against Jason’s cheeks.
It was huge. No wonder he had requested that Jason open himself with four fingers. Tim’s gaze was trained on Jason’s face as Roman pulled the thong aside and wasted no time sinking his cock into Jason’s twitching hole. Jason’s face screwed up in pleasure and he groaned softly, back arching as he wiggled his hips back onto Roman, who chuckled at the lewd display.
“You like that, you bitch?” Jason nodded and moaned as Roman began to thrust, filling Tim’s ears with the sound of skin slapping and Jason’s lewd moans as he nodded.
“Yes sir! Fuck, s’ so big! Fuck me!” Jason cried out when Roman slapped his ass harshly, eyes widening and lips parting softly. Tim trembled excitedly as he stroked himself, keeping the hand on his mouth to muffle his soft pants and groans watching the object of his desires writhe and moan in pleasure. Every powerful thrust had Jason sliding against the desk and crying out, cheek pressed to the wood and legs trembling. It was beautiful.
Roman must have angled himself to hit Jason’s prostate because his cries and moans got louder, his eyes closing and mouth hanging open as his nails dug into the wood where he had been gripping it. Drool dripped out of his open mouth and Tim imagined he was the one bringing Jason this much pleasure. That it was his cock spearing the other vigilante open and fucking him to pieces. Tim had to squeeze the base of his cock to keep himself from coming at the thought.
Roman continued to pound Jason’s hole, grunting as he chased his own pleasure. A heavy hand slammed down on Jason’s ass and the man cried out in pain but that only egged him on. He continued to deliver sharp blows across Jason’s ass and thighs until the skin was a deep red and Jason trembled beneath him, tears in the vigilante’s bright blue eyes as he moaned and pushed back into every hard thrust.
Tim watched, enraptured as he began to stroke himself again, his gloved hand tight around his cock as he fixed his eyes on the handprints left on Jason’s pale skin. He panted softly, a quiet groan of his own escaping, but thankfully the men inside were too caught up in their activities to notice him.
Suddenly, Roman pulled out, his cock glistening with the lube that Jason had used to open himself, and grabbed him by the waist. Jason allowed himself to be flipped over, ankles slung over Roman’s shoulders as the man re-entered him and continued his brutal pace. Jason’s head tilted back as he moaned, cock straining and leaking against the panties. Each thrust bounced his pecs and Tim nearly drooled at the sight. Jason’s back arched off the desk when Roman grabbed his cock, sliding his hand across it quickly. Jason’s head rolled to the side and his eyes were half lidded.
Tim gasped as they made eye contact. There’s no way Jason didn’t see him, blushing with his hand down his pants.
But he didn’t stop, even as Jason’s eyes widened in shock at the discovery that he was being watched, and by Tim no less. Tim stroked himself faster, his grip tightening as Roman groaned and came, fucking him cum deep into Jason who was staring at Tim, bewildered and with an embarrassed flush creeping up his neck.
But he couldn’t help the moans that continued to spill out as Roman stroked him and he quickly came as well, crying out and legs trembling as he writhed in pleasure.
The sight was too much and Tim came as well, stroking himself through his orgasm. His underwear was quickly soaked in cum and he panted, leaning against the wall to catch his breath for a moment.
Jason had seen him.
He was gonna fucking kill Tim.
If he rushed home, he could probably jerk off a few more times to the footage his mask had collected before Jason blew his brains out. That seemed like a good decision so Tim quickly wiped the cum off of his glove and clicked his belt closed before leaping off the ledge.