Chapter Text
When Jay woke, she was alone. She was disoriented at first, confused as to why she was unable to move. Then the memories came flooding back. Being dragged into the alley and drugged. Then shoved into the trunk. And finally, chained up here. In the basement of a man who had apparently been stalking her for a while. She groaned softly, squirming as her chest and cunt throbbed with the reminder of yesterday's "punishment." She was still naked and chained up, but the blankets beneath her were switched for clean, dry ones and the mess had been wiped up from between her legs. Small mercies, she supposed. Her hair had also been taken out of the bun she had thrown it in for work the day before and brushed out. Her stomach curled at the thought of that little creep touching her and brushing her hair as she slept, unaware and unable to even put up the weak resistance she had showed so far.
She was currently debating trying to scream for help in hopes there was someone close enough to hear her when Tim returned. He smiled at the sight of her awake, and hurried over to the bed. He was carrying a bottle of water, and Jay suddenly realized just how thirsty she was. Her throat was dry and sore from all her screaming and crying and so she didn't resist as he carefully lifted her head and held the bottle to her lips.
"Glad to see you're awake. Did you sleep well? You looked so peaceful." She didn't answer, as she was too busy gulping down the water. He pulled it away from her mouth far too soon for her liking and she glared.
"Sure. Nothing ensures a good night's sleep like being kidnapped and raped by a perverted little freak." Tim frowned, but Jay met his disappointed stare with her own displeased expression.
"Don't be crass, Jay. And don't act like you aren't enjoying it." She grimaced as he set down the water on the nightstand and began to play with her chest. Her tits were mottled with bruises from the riding crop, and his fingers dug into the dark splotches, massaging the sore flesh. She gritted her teeth, swallowing any sound of pain that threatened to escape. "How many times did you cum yesterday? You loved what I did to you, no need to be shy about it. I only hurt you because you hurt me. I'd never mistreat you, Jay. I love you. I've loved you since i first laid eyes on you."
Jay's stomach dropped at the confession. Her situation was only becoming more delicate. If she stepped too far out of line, would he kill her? She thought carefully before answering.
"You don't even know me, not really. Sure, you've followed me home from work a few times, but you don't know what kind of person I am. That's not love, it's obsession. You need help." Tim went quiet, hands stilling on her chest. His expression was hard to read, and Jay's heart thudded loudly in her chest. They just stared at each other for a long moment before Tim smiled softly and leaned over, one hand moving to grab Jay's jaw and hold her still. Her eyes widened as he pressed their lips together and climbed on top of her, slotting one clothed knee between her spread legs. She let out a soft sound of protest, but Tim just used the opportunity to deepen the kiss, slipping his tongue into her mouth. By the time he pulled back, Jay was panting softly and he smiled down at her, moving the hand on her jaw to brush a strand of hair out of her face.
"Oh, baby, I've done far more than follow you home. I know everything about you. You love to read, and your favorite book is Pride and Prejudice. You're a great cook, even if half the time you're too tired to eat anything but ramen or cereal." Jay shivered as he leaned down to press soft kisses against her neck, the hand on her face moving back down to play with her nipple, which quickly hardened under the attention. His knee began to grind against her cunt and her breath hitched. "All your books are organized by the authors' last names. Alphabetically, of course. You smoke menthol cigarettes, at least four a day. More if you're stressed. You don't like to go on dates, but if you're really pent up, you dress up and go to that club to find someone to sleep with. You never stay with them until morning, and you never bring anyone back to your place. Should I go on? I know everything, Jay. What laundry detergent you use, what shampoo and conditioner you like, where you grocery shop. I know your credit score, and exactly how much is in your bank account right now."
Jay closed her eyes and shook her head, heart pounding as he kissed his way down her neck, biting and sucking dark hickeys into her soft skin. She gasped as he moved down her collarbone, leaving a dark hickey before lapping at her nipple.
"No, no no stop, please-" Her soft protests went ignored as he sealed his lips around the soft bud and sucked, drawing a soft moan out of her. She trembled as he nipped and sucked on one nipple, his hand still pinching and rolling the other between his fingertips. The worst part was it felt good, and she could feel herself getting wet. His knee still rubbed against her pussy and her juices quickly soaked into the leg of his pants. The rough material almost hurt as it dragged across her sore lips and swollen clit and she couldn't stop herself from squirming and writhing in an attempt to escape the pleasurable sensations. It was futile, and Tim simply continued, sucking and nibbling on her sensitive nipple as she struggled.
Jay desperately wished she could cover her mouth, or that he would gag her again to stifle her moans. It disgusted her that she could behave so wantonly as she was getting assaulted by someone that had clearly been stalking her for months. She was relieved when Tim pulled off of her tit and his knee left her cunt, sagging against the bed and panting. He was looking over her body hungrily, his lips reddened and wet from kissing and sucking dark hickeys into her skin. His cock bulged obscenely in his pants and he palmed at it roughly as he moved to kneel between her spread legs. As he pushed his pants and underwear down in one smooth motion, she realized what he was doing and began to writhe once again.
"Please, stop! You're a disgusting fucking pervert, don't you fucking dare-" Before she could finish, Tim was lifting her hips, pulling her so harshly that her limbs strained against the cuffs. She cried out as he lined up his cock and buried himself to the hilt in one smooth thrust, immediately setting a rough, fast pace as he rutted into her. Jay let out a choked moan, her eyes rolling back as her pussy spasmed around the sudden intrusion. Tim groaned loudly as she pulsed and fluttered around him, his fingers digging harshly into her hips to hold her in place. With every thrust, the bed shook and so did Jay. Her sore tits bounced every time Tim slammed into her cunt and she couldn't help but let out sharp, choked off moans through her clenched teeth.
"Fuck, Jay, you were made for this-" She shook her head and opened her mouth to protest, but another rough thrust turned any words she was trying to form into another whiny moan. She tried to gain control of herself, but it was an impossible task. Tim's cock bullied its way deeper inside her with every thrust, dragging against her most sensitive spots. Each time he pulled out her pussy clenched, trying to suck his cock back in. It was like her body was entirely out of her control. She could feel the familiar sensation of her orgasm building and tried to hold it in, which only resulted in her clenching down harder and bringing the man inside of her even more pleasure.
In the end, what drove her over the edge was the kiss of his cock against the deepest part of her. The tight muscle of her cervix kept him from entering, but it was such an intense mix of pain and pleasure that she had never experienced before. She writhed against her bindings and against Tim's hands on her waist as she came, gushing around his cock. His pants were soaked but he didn't seem to care as he continued to fuck her through her orgasm, taking in the sight of her squirming in pleasure and squirting on his cock. Finally, he buried himself as deep as he could and came inside her, and despite all her protests her pussy milked him for every last drop. His hips twitched as he grinded against her, forcing his cum as feel as he could get it.
By now Jay had gone limp, only twitching slightly as she felt him cumming inside her. She whimpered softly as he lowered back down and laid on top of her, his softening cock still buried deep inside her as they both panted and tried to catch their breaths. Tim's hand ran through her hair, and she didn't have the strength or will to fight against it. He played with the soft, silky strands and enjoyed the feeling of her pussy twitching around his now soft cock.
"You did so well, Jay. You're so beautiful." He mumbled softly, pressing a chaste kiss to her soft lips as he eased himself out of her and admired the sight of her, fucked out and leaking his seed. "I can't wait until you're pregnant. You'll be such a beautiful mother."
Jay's eyes filled with tears again but she didn't dignify him with a response as he climbed off of her and began to clean up the mess they had made. All she could do was lie still and quiet, even as he slipped a thick, long plug into her cunt to ensure the majority of his cum stayed inside. Once they were both wiped clean, he pressed another kiss to her cheek. Tim moved across the room and Jay let her mind wander. It had only been a single night and she already felt like she would never get back to her regular life. Did he really plan to keep her locked up forever? The Drakes had money, so that wouldn't be an issue. But what if he got bored?
She was so lost in her own thoughts that she hardly registered his return until he was placing a hand on her jaw, slipping a thumb into her mouth and prying it open. She tried to pull away, but there was nowhere to go and soon he was shoving a silicone ball into her mouth. It had a strap that he buckled behind her head and she let out a muffled sound of confusion. Tim gave her an apologetic look.
"Sorry Jay, I've got to go. Can't have you making too much noise." Hope sparked in her chest. If he needed to keep her quiet, then there was a chance someone would hear her. Maybe a housekeeper or something. She squirmed, letting out a muffled protest as he pulled out a roll of tape from his pocket, along with three small bullet shaped vibrators. He taped two to her nipples and the third to her clit before slipping a thick blindfold over her head. Her heart raced as she was plunged into darkness. "This will keep you busy. Don't want you getting bored."
Jay shook her head, pulling against the cufffs once again but Tim's mind was made up. Suddenly all the toys buzzed to life, and she heard his footsteps recede. The door slammed closed with a loud thud, and she was left alone, legs shaking and muffled moans echoing in the otherwise silent basement.