Bought And Paid For

TITLE: Bought And Paid For AUTHOR: Midknight CHAPTER: 4 of ? FANDOM: Gossip Girl SHIP: Chuck / Jenny RATING: NC-17 CATEGORY: Erotica SPOILERS: Season 1 - A couple. SYNOPSIS: WARNING: HERE BE SPOILERS - SEASON 1. Chuck overhears Jenny's request to Nate for the loan of two thousand dollars and makes her a proposition to give her what she needs when Nate is unable to. DISCLAIMER: I do not own Gossip Girl. None of these characters belong to me. They belong to whoever created them and whoever else does. I pay homage to them and I make no profit from this story in any fashion, way or means. AUTHORS NOTE: I apologize before hand and hope you will forgive any errors or blatant discrepancies. This one's a little darker than my usual fare, so bare with me. FEEDBACK: Yes Please. It helps. It really, really helps. - midknight_tales@yahoo.com CHAPTER FOUR Jenny made no protest as he again leisurely, intimately explored her body under the warm spray in his steamy shower stall under the thin pretext of helping her shower. Chuck had, had access to willing female flesh since his early teens, but he couldn't get enough of her pale, smooth, sumptuous skin and her guilty, shy reactions. Her nipples remained stiff despite the heat of the shower and his light and intermittent attention to them. He turned her back to him and washed her back before taking his tie fondling her ass. She flinched when he let a finger caress the rosebud of her asshole. "You're going to have to get over that, eventually. I am going to screw that tight ass of yours, you'll be better off if you're ready for it." He informed her in a low voice and a matter-of-fact one, reaching around and pulling her back against him, nestling his semi-erect dick in the crack of her ass. "Please don't." she implore quietly and simply. "You know I will if I want to, don't you?" he told her, lowering one hand to caress her sex. "Yes." She replied in a dead voice. "And?" he invited her to continue. "And... There's nothing I can do to stop you." She finished. "Very good, you got it in one." He praised her as he started to finger her and let his other hand cup and fondle her breast, Her cream was thicker and warmer than the water that reached his hand and he smiled against the shell of her ear. He walked them a step forward, so that the spray was on his back. "Lean forward and put your hands on the wall." He instructed, his fingers sawing in and out of her and collecting her sex grease. "Chuck..." she started, but he cut her off by pinching her nipple hard enough to make wince. "Jenny." he rumbled by way of reissuing his command and after a moment she complied. He drew his fingers from her snatch and without pause or warning worked one of them into her tight asshole. She tensed and grunted, the tight ring of muscle clutching at his finger, but he twisted it and worked it all the way in with the help of her unwillingly supplied lubrication. She pulsed around him and he saw her head droop as she breathed raggedly. He twisted his finger slowly and crooked it slightly to caress the tight flesh of her rear channel. Jenny shuddered as he slowly worked his finger back and forth inside her, slowly increasing the length of his strokes while still fondling her breast and rolling and tweaking her nipple. He also pulled her back slightly, getting her to press back onto his finger. He lapped at the water on her shoulder before pressing his lips to the skin of her neck, just below her ear. "Are you ready for another one?" he queried, keeping his voice low, his tone letting her know his question was rhetorical. Her head rose and turned with give him a narrow eyed glare. "Does it really feel that bad." He asked, genuinely curious. She seemed to have a powerful phobia about anal sex and he was even starting to wonder if he might not be the first to try it with her. "It's... It's... It's horrible and... and I want you to stop, but... but I know you won't." she responded petulantly even as his finger now slid easily in and out of her ass and her hips rocked slightly, unconsciously to the same rhythm. "Are you sure, Jenny?" he mused and slowly started to work a second finger into her. She made a soft whimper when her asshole finally surrendered to his constant and unrelenting pressure and he was wriggling and twisting his fingers into her dank depths. "Breath... Just breath." he advised as he explored and stretched tight rhythmically convulsing flesh. She whined when he started to thrust them in and out. "Stop fighting it." He told her as he relinquished her breast and let his hand slide down her torso to attend her clit. She jumped slightly, gasping as she backed up onto his fingers at his touch as he slowly started to frig her clit. He chuckled in her ear as he co-ordinated his efforts, working her clit and driving his fingers in and out of her ass. "I don't think you're being truthful, Jenny. With, me or yourself." He stated as her sex grew hotter and wetter as he caressed her folds and his fingers in her ass moved with longer, deeper strokes and with less resistance although her tight flesh remained a snug, warm caress around his digits. "I think that you're confused, that you want it to feel bad, to be horrible, that it can't possibly feel good or be exciting because that would be wrong, that would make you bad, a deviant." He proposed while kissing her neck and continuing to explore her with his fingers. "N...N...No." she protested, but he ignored her. "You're wrong, of course. You might not like it at first. It will hurt. I have a big dick and you have a sweet tight little ass, but I can make it feel good, if you let me. I am going to fuck that sweet ass of yours. We've established that as a given and we know I'll have fun and enjoy doing it irrespective of how you feel about it. It's going to be up to you whether you get something enjoyable out of it." He continued nipping lightly at her skin as she rocked against his fingers in her snatch and inadvertently against the ones in her ass. "So why don't you just do it already? You know I can't stop you. Just... just get it over with already." She asked angrily after she groaned and her sex pulsed around his fingers. "Do what?" he countered with a question of his own. "Fuck me in the ass." She answered. "Are you answering or asking?" he queried, letting amusement color his tone. "You're a real bastard, Chuck." She groaned as he applied more circling pressure to her clit and worked his fingers deeper and faster into her ass. "I know, Jenny." He admitted with a wicked chuckle and slipped his fingers out of her ass. His dick was hard and throbbing against the taut planes of his stomach. The idea of taking the last of her virtue excited him and the temptation was nearly more than he could withstand, but he managed. "Bend further forward and brace yourself." He instructed in a tight, clipped tone, gripping her hip with one hand to pull her back while he grasped the base of his cock with the other and urged her to spread her legs further by tapping his foot against the inside of her ankle. He felt Jenny shiver despite the heat of the water and billowing steam around them, but she did as he told her. He guided himself to the puckered starfish of her asshole and she inhaled sharply and tense as he pressed his tip into it until he met resistance and stopped. She was trembling in waves as she fought her desire to pull away from him he remained poised against her. He bent over her back, applying a little pressure and drawing a whimper from her. "Are you ready, Jenny?" he asked, blowing lightly on the shell of her ear and he felt her draw a shuddering breath. "Yes." She finally whispered with apprehensive resignation as the moment drew out and the only sound was the hiss of the shower and their breathing. "Remember you said that." He told her as he backed up slightly and quickly guided his dickhead lower and through her folds to drive himself into her with a single, hard thrust. She let out a gasped cry and he grunted as the heat of her sex enveloped him and her tight flesh slid along his length, clutching and flexing as he lanced into her core. Chuck guided her hips in tight little circles with both hands as he ground into her and against the firm curves of her ass cheeks. Chuck felt his eyes droop slightly, the small of his back pulsing and his dropping back as waves of pleasure radiated through him. "Fuck that feels good." He growled as her sex squeezed and twisted around his shaft as she adjusted to his sudden invasion. He stepped forward, forcing her to straighten. He slid a hand up her back as he shook water from his face and hair. He wound his fingers into her hair and the twisted her head to the side and back until he could lean forward and capture her lips in a hard, forceful kiss. her lips opened under his and he stormed the ramparts of her teeth with his tongue to tangle and twist with hers. Her lips vibrated against his as she moaned and unbidden pressed down and back onto him. He wondered if she felt him smile. He broke the kiss nipping at her full lower lip. "Fuck me, Jenny. Fuck me good." He instructed into the shell of her ear before lightly nipping her earlobe. Jenny stared at him over her shoulder for a moment and then letting her eyelids dip for a moment pressed back and down onto his cock with purpose and circled her hips. Chuck groaned and pressed his forehead on the smooth wet skin between her shoulder blades as he thrust and matched her rhythm and pace. He clutched at one of her breasts, pinching and pulling at the nipple while he let the other hand drift down to cup her and roughly diddle her clit as she worked herself up and down his length. Her sex was a delectable, moist, hot massage that sent wave after pleasure into his belly and up along his nerves, tightening and setting his balls to churning, ratcheting up the tension and his need for release. Her breasts fit perfectly into his hand and he had to concentrate in order not to permanently mark the firm flesh as his fingers tested it. Not that he wouldn't love to leave his mark on her, but it might be a bit hard fro her to explain in the girls locker room. Her breathing changed to the heavy, moaning pant and then to the little cries, which he had heard earlier as she rode him in the recliner. He smiled and nipped at the skin of her shoulder as he thrust harder, feeling the shockwave of their colliding bodies run through her as he took his pleasure from her with rougher abandon and she strained to match him stroke for stroke. The spray cascaded down on them both, an added indulgence, an added caress on his skin. Chuck, nipped, sucked and licked at the skin of her neck until his lips were near her ear again. "This feels so good. You're good at this, Jenny. Better than I ever would have thought. And... And I think it's because you like it. It's surprising and strange and scary, but you like sex, you like fucking." He ground out from between clenched teeth as he dragged in heavy breaths through his flared nostrils. She shook her head to negate his statement, spraying fine drops of water to either side, but her rhythm never faltered, even with the quivers he could feel running through her. "You're worth every penny. I got an even better bargain than I thought." He continued and she raised and turned her head to glare at him for a moment before dropping it with a heavy groan as he slammed into her, pinched her nipple and apply pressure to her clit at the same time, making her sex clutch at his shaft. "You can deny it for as long as you like, My Sweet, but you like it. You hate me with every fibre of your being, for things I have done, you'll find it in you to hate me even more for the things I am still going to do and have you do, but this..." he drove himself into her and ground against the firm globes of her ass, "But, his you like... You can't help yourself, it shames you." He told her in a cool measured tone even as his eyelids drooped and his ass clenched as he battled back his climax. "You might even hate yourself as much as you hate me because of it, but you really shouldn't. There is nothing sexier, more admirable than a woman who can enjoy sex." He informed her. "I hate you." she wailed as he felt her sex flutter around him. "We've established that, Pet, but the fact remains that I'll be the one that gives you your second orgasm and, Jenny, the night is still young." He rasped in her ear before grasping her hips and pounding into her with hard, deep, rapid thrusts. She cried out sharply and then cried out again, a long drawn out howl as she arched back against him as her spine bowed in climax and her sex squeezed and twisted around him in a flooding vice-like grip, which with a grunt he continued to pound into as he gave into his desire. He threw his head back and roared his release, letting the spray run over his face and into his mouth as he humped and pumped his seed into Jenny for the second time that evening. Her snatch rippled and flexed around him, milking him as pleasure coursed through him like a flood of electricity that energized every part of him and set his nerves on fire as his muscles tensed and released in quick succession and erratic waves. He lowered his head and spat out water to drag in air. He could feel Jenny shake as she rode out the delightful upheaval of her climax she would rather deny. Her shudders moved her channel around him sending more sparks of enjoyable sensation sizzled along his spine and drawing the last of his essence from him. Chuck ground and humped against her for a few moments more and then slowly withdrew. Jenny whimpered as he did and collapsed to her knees and then dragged herself away from him and against the tiles of the wall underneath the showerhead, her face hidden by her hands. "The truth hurts, Jenny. Almost as much as getting fucked in the ass for the first time." He informed her as he rinsed himself under the spray. He felt he was being just a little cruel being so blunt as he looked down at the huddled blonde girl, but as the song went: 'Cruel to be kind in the right measure.' He had plans for her and he needed her to become comfortable with her sexuality in order to maximize his use of her. "Finish your shower and call your dad." He instructed. "I'll leave a robe for you on the bed before I order dinner from room service. Come out when, you're ready." He continued and waited until she slowly rose to her feet, her eyes not meeting his and nodded sullen understanding before leaving the shower. TO BE CONTINUED