Chapter Text
It was an uncharacteristically quiet night for Gotham. There were the usual sounds of traffic and sirens in the far distance, but there were far fewer people out tonight than normal. It was the perfect night to enact his plan. The alley Tim concealed himself in was shrouded in inky darkness, the perfect spot to lie in wait for his unsuspecting prey. His car was parked just outside the alley, only a few steps away. Tonight, he did not wear the Red Robin uniform. Black cargo pants and a hoodie were far less conspicuous. The hood pulled up over his head and the black cloth mask were enough to conceal his identity from any potential witnesses. It's like fate itself was smiling upon him, providing such perfect circumstances to execute his plan. The object of months of desire and obsession would pass by at any moment now, and he was ready to make her his.
As he stood quietly, concealed by shadows, he heard the long awaited footsteps of his prey. He knew her gait, the sound of her work shoes, simple black kitten heels, against the pavement. After all, he had followed her along this exact route countless times by now. He clutched the syringe in his gloved hand, filled with a fast acting paralytic. She would surely put up a fight, not that a civilian girl could stand a chance against his years of vigilante work and rigorous training. He held his breath, unable to keep himself from smiling beneath the mask as his prey finally stepped into view.
Jay Todd was as gorgeous as always. It was a shame her figure was currently hidden by a bulky jacket, but he understood. Someone as beautiful as her had to be careful in a city like Gotham. Especially when her work uniform from the diner a few blocks away was so tantalizing. The apron cinched at her waist perfectly, and the buttons at the top of the light blue dress constantly strained to contain her ample breasts to the point that Tim was surprised they hadn't popped off yet. Her dark, wavy hair was pulled up tonight, her bun messy and bangs falling out from a night of busy work. A cigarette hung between her soft, plush lips. It was such a disgusting habit, but she somehow made it look erotic. He watched eagerly, waiting for her to take a few more steps.
Once she reached the center of the alley, he struck. It took little effort for Tim to step out behind her and wrap an arm around her neck. He felt her gasp in shock against him, the cigarette falling to the concrete. Before she could scream, he slapped a hand over her mouth and drove the syringe into her side, dragging her against him as he backed quickly into the dark alley. He felt her jerk in pain as he squeezed the plunger, his heart racing as she clawed at the gloved hand on her face with an enraged cry. As soon as the medication was administered he withdrew the syringe and let it fall to the ground. His newly freed arm wrapped around her chest, holding her tightly as she writhed and grunted. He ignored the growing heat in his gut and the sudden tightness of his pants as she squirmed against him. His hand on her chest found her breast and he squeezed it tightly, and Tim out a breathy groan. Her struggling only stimulated him more as her squirming only served to rub her ass against his hardening cock. He couldn't resist rutting against her as he waited for the drug to take effect. She let out a muffled sound of fear and anger at the realization of what he was doing, but it was too late now. Her struggling became weaker and it wasn't long before she was sagging against him, her writhing reduced to the occasional weak twitch.
He had done it. She was finally in his grasp, unable to resist as he dragged her deeper into the alley and draped her face down onto a rusted, whirring AC unit. She attempted to push herself up, but her hands only managed to weakly press against the dirty, rusted metal before falling entirely limp. The paralytic was in full effect now, leaving her conscious but unable to move as Tim executed the next step of his plan. His mind whirled excitedly as he took in the sight of her, the object of his obsessions helpless in his clutches. Her face was turned to the side and Tim could see her glaring at him out of the corner of her eye. He couldn't stop smiling beneath the mask as he retrieved a small black duffel bag he had stashed behind the rusted out unit, setting it next to her prone body and quickly unzipping it. The alley was so dark that he wasn't worried about anyone seeing them, but he didn't want to waste too much time here.
The first thing he retrieved was a roll of silver duct tape. It was easy for him to remove her baggy jacket and pull Jay's limp arms behind her back, wrapping the tape around her wrists and up to her elbows to ensure it would be secure. He flipped her over onto her back, just to see the way her chest jutted out even more obscenely than usual with her arms and shoulders forced back. Jay's head rolled limply to the side, even as her eyes remained trained on her captor, bright with anger. But Tim could see the underlying fear, and it only excited him more.
"Don't worry, Jay. I'm not going to hurt you." If she was shocked that he knew her name, she didn't show it. His eyes trailed down to her chest, both gloved hands reaching to grab and squeeze at her tits. He couldn't resist, and his fingers quickly found the buttons, undoing the top few and pushing her bra down to let her tits spill out if the plain black cups. Her nipples quickly hardened in the cold night air and Tim eagerly groped her further, pinching and tugging at the perky, dusky buds. She whimpered softly and Tim shuddered with arousal.
After nearly a full minute of toying with her chest, Tim slid his hands down in favor of flipping up her skirt. She was wearing plain black cotton underwear, and Tim groaned softly as he forced her thighs open to step between them. Her legs twitched, but that was the only resistance she could provide. She was breathing heavily now, causing her tits to rise and fall quickly. Even now, scared and angry, she was sinfully erotic in his eyes. Tim rubbed a gloved hand over her clothed cunt, tracing her plush lips and the moist seam between them. She wasn't wet, not yet, but he knew she could feel everything he did to her like this, despite the drug coursing through her veins. He quickly unzipped his pants, just enough to pull out his cock. It was almost painfully hard now, throbbing as he took it in one gloved hand and rubbed the tip against the seam of her twitching lips. Precum smeared across her panties and he groaned softly, pushing the moist fabric to the side. Her pussy was bared to him, puffy lips covered with neatly trimmed hair. He rocked forward, sliding his cock between those soft lips and grinding the tip hard against her clit. Jay let out a soft sob, and Tim looked up to see tears forming in those angry blue eyes. He shuddered and groaned, thrusting against her harder. Her entire body rocked with the force of it, her tits bouncing with the movement and Tim used his free hand to grope her chest, playing with her harder nipples as his cock slid back and forth against her clit.
He could feel her body reacting to the stimulation, coating his cock in her juices as he rocked against her cunt. She let out helpless little sobs as Tim lined his cock up with her entrance. She wasn't wet enough just yet, but he was in a hurry. In one slow, steady thrust he pushed his cock inside her, hips twitching excitedly as he let out a shuddering breath. She was so tight around him, squeezing his cock mercilessly as he began to thrust. Now both hands groped at her chest as he rutted into her, ignoring her pained whimpers and soft cries. They weren't loud enough to draw attention of any passerby.
Tim wasn't quite sure how long he lasted, but it couldn't have been more than a few minutes. Every thrust filled the alley with the loud smack of his hips against her thighs and the squelch of his cock invading her fluttering pussy. His grunts and her cries mixed, and as he drew closer to cumming he was forced to put a hand over her mouth as his rougher thrusts made her cry louder. That was how he finished, one hand on her tit and the other over her mouth as he desperately fucked into her tight cunt. He buried himself deep as he came, hips twitching forward as he spilled his seed inside her. He shuddered as he panted, quickly recovering from the intensity of the orgasm.
He reluctantly pulled out his cock, retrieving a long, thick vibrator from the bag and shoving it inside to keep his load from leaking out. Once he tucked his cock back into his pants, he admired his handiwork. Only a few drops of cum had escaped, and now her lips were stretched obscenely around the hot pink toy shoved deep inside. Another strip of duct tape secured the toy and his cum inside her. Her ruined panties would serve as a lovely gag, and he quickly stripped her of them in favor of shoving them in her mouth and taping it shut as well. Now all that is left it to tape Jay's legs together, ensuring she can't run if the paralytic wears off sooner than anticipated. Tim wrapped her ankles with several layers of the tape, admiring the way her work heels force her feet to arch. He made a mental note to buy her more pairs of taller heels later. He wrapped a few layers of tape around her thighs as well before putting the rest of the roll back into the bag. He retrieved the remote for the vibrator and turns the device on, relishing in the way Jay's eyes fly open in shock at the sudden pleasure forced upon her stuffed and taped cunt. She can't even squirm thanks to the paralytic drug, and is simply forced to lie still and accept the pleasure Tim bestows upon her. For the final touch, Tim clipped two small clamps to her nipples, watching in awe as they immediately begin to redden under the pressure.
He left her like that for a few moments as he cleaned up, shoving her jacket into his bag and retrieving the empty syringe. He was careful to rid the alley of all evidence of their scuffle before checking up and down the street. It was thankfully empty, no potential witnesses to be seen, and he had disabled all security cameras earlier in the evening. He slung his duffel bag over one shoulder, and hoisted Jay into his arms, carrying her princess style to his awaiting car. She folded up perfectly in the small trunk, bound gagged and stuffed full of his cum and the buzzing vibrator. He tossed the bag in on top of her before slamming the lid closed. He was still grinning like a fool, humming a cheerful tune to himself as he locked the trunk and made his way to the driver's seat. Their next stop would be Jay's new home. Tim felt himself getting excited once again, his cock twitching in his pants as he thought over all the plans he had in store for his new girlfriend.