Bought And Paid For

TITLE: Bought And Paid For AUTHOR: Midknight CHAPTER: 5 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 FIVE Chuck lounged on his sofa in silk pajama pants and top and watched as room service wheeled in the sushi he had ordered. He glanced through the door to his bedroom and saw that the robe was still on his bed. He frowned and had them arrange the sushi on the coffee table before signing for it. He put his ear to the bathroom door, but didn't hear the sound of running water. He rapped his knuckles on the door. "Jenny? The food's here." He informed her, ignoring the urge to open the door and find out what she was doing. He returned to the living room and a few minutes later she appeared, trying to adjust the short silk robe that barely covered her sex. He gave her an amused look and she seemed to realize, as he did, that after what they had done, her need for modesty was rather ludicrous. "I need to call my dad. It's getting late." She told him quietly and he made a gesture for her to continue. She rummaged in her purse for her mobile. He kept half an ear on the quiet conversation, but it seemed that her father trusted her and she didn't have to work to hard to let her sleep over at a friends with such short notice. Well that boded well for his future plans for her. The 'I love you, Dad.' At the end was quite sweet. Chuck patted the sofa next to him once she stored her phone and she joined him without comment. She nibbled and picked at the selection of sushi and declined his offer of Saki and had water instead. "I could order something else if you like." He offered. "No... I'm... I'm just not very hungry." She declined. He looked at her speculatively. She kept sneaking glances at him and fidgeting. "What's on your mind, Jenny?" he asked lounging back. "What's on my mind? Are you serious? Really? I have to do what ever you want, I have to have sex with you or you'll ruin my life. What do you think is on my mind?" she retorted with fiery exasperation. He reached for her and she flinched away, but he persisted, and slid his hand into her robe to capture her breast at which point she froze. He gently, slowly fondled the firm globe, lightly rubbing his thumb over her nipple feeling it start to slowly swell and stiffen. "I'm guessing you're still wracking your brain to find a way out. But, I meant besides that. You look as if you want to ask me something." He continued unperturbed enjoying the feel of her smooth, warm flesh. "Would you stop that, please?" She asked as he started to pay more attention to the tight, hard tube of her nipple. "Why?" he queried and she groaned as her pinched and rolled her nipple. "It's distracting." She responded, but made no effort to move away or stop him. "Why?" he asked again. The tip of her pink tongue flicked out to wet her lips. "It... It feels... Good." She finally admitted with a sigh. "And that's bad?" he wondered. "No... I mean yes... I mean... It's wrong." She responded, confusion and desperation coloring her tone. "Why?" he asked yet again, watching her intently, keeping his features neutral but interested. "Will you stop asking that... What are you doing to me?" she asked plaintively, finally raising her large light eyes to meet his. Chuck leaned forward. "I thought we'd established that? What I'm doing to you, My Dear, is whatever I want." He responded, searching her eyes before kissing her. He started off soft and slowly increased the pressure. Her eyes fluttered closed and her lips parted under his as she shifted her head, kissing him back and allowed him to plunder her mouth. Her chest heaved breathlessly, pressing her breast into his hand when he broke the kiss. He watched as she lightly wiped her lips with the side of a slender finger. He looked at her expectantly and she worried at her lower lip. "Why didn't you just do it?" she asked in a rush. "Do it. Jenny, trust me I've done it to you and we've done it together." He informed her, his hand slowing, but not stilling in its restless exploration of her breast. "No... I mean... Why didn't you..." she paused, looking away for a moment before taking a deep breath and continuing, "Why didn't you just stick it in my ass earlier?" She blurted and then sighed, her chin dropping, her eyes sliding away from his. He looked at her for a moment, actually considering her question. "I wasn't ready to do that yet. It's a pleasure I'm saving. Did you want me to?" he ended with a question of his own. "No." she replied almost petulantly, offended and he stared at her intently, coolly, letting his eyebrow raise slightly to question the truth of her answer. "No! I didn't... don't want you to do that to me." She told him, scandalized at his implication. "But... But, you're going to. You made that abundantly clear and... and..." she faltered. "You thought you could handle it... Or even better, now you're a little curious, not so sure it would be such a horrible thing." He finished for her and she shook her head in denial. "Lie back. I want some dessert." He instructed, grabbing her thigh and pulling her onto the sofa so that she was lying on it, his hand still slowly fondling her breast. "Jeezus, Chuck. Don't you ever get enough?" she asked in dismay as he undid the belt of her robe and parted it exposing her crotch. He let out a short bark of laughter as he let his gaze sweep up her body from her sex to her face. "Ask me that in a little while... If you can." He challenged and before she could respond buried his head in her crotch. "Wha... What are you?..." she asked in protest and then gasped and moaned as he expertly started to lap at her folds before latching his lips onto the flesh around her clit and swirling it around her sensitive pearl. He alternated between long, exploratory swipes of his tongue through her blossoming petals; probing her sweet, juicy channel to seek out the source of her sweet nectar and suckling at her clit. She writhed in reaction, her heel sliding back and forth along his back while the other dug into the leather of the sofa. He reached up, sliding his hands over her fluttering belly, over the slight ridges and valleys of her ribs to blindly capture her breasts, explore them and find her nipples, which he rolled pinched and tweaked. Her moans, groans, gasps and finally soft, mewling cries were music to his ears and the spicy scent of her arousal enveloped him to deliver a complete sensory experience. Chuck grinned as he felt her hands wrap over his, squeezing in encouragement instead of trying to remove them and her hips rocked and pressed her delectable snatch into his mouth. He continued to go down on her with hungry abandon, using the scrape and nip of his teeth to further stimulate her open, flooding sex. He took her to the edge, gauging her closeness to climax with practiced ease and then backed off and slowed down until her panting slowed before revving her up once more. He repeated the process again and again, pleasuring her, just pushing her that little bit further each time, but never far enough. Chuck worked her into another writhing, bucking, panting lather with waves of shudders shaking her body and then raised his head causing her to make a whine of disappointment, her back arching as she lifted her ass in an attempt to follow his mouth and her hands clutching harder at his lest he remove them as well. He licked his lips. Her hair was in wild disarray from thrashing her head about and her eyes were bright and wild, her face flushed and sweaty as if she were running a fever. "I think I've had enough." He informed her calmly and she blinked uncomprehendingly. He tried to release her breasts and her hands held his in place. "N... N... No. Why?" she asked, stammering in confusion with desperate need coloring her pleading tone. "Why not, Jenny? What do you want from me?" he countered staring at her face intently, his eyebrow slightly raised to emphasize his need for an answer. "I...I...I..." she stammered and he saw the realization hit her eyes, saw her swallow heavily, saw shock and dismay war with the need he had instilled in her. "I... I don't want you to stop." She whispered, turning her face away from him in shame. Jenny didn't resist when he shrugged her hand off and reached for her chin and gripping it turned her head to face him once more. "What was that? I couldn't hear you." He asked, slightly cocking her ear in her direction while at the same time sliding the fingers of his other hands through her wet folds sending a shiver running through her petite frame. She closed her eyes for a moment and when she opened them he smiled at the resignation he saw there. "I don't want you to stop. I don't want you to stop!" she admitted repeatedly with increasing volume and voracity. He ran his thumb over her lips and leaned closer. Chuck shifted his head from side to side, making a show of studying her and considering her admission. "Answer this correctly and you might get what you want." He told her softly, but emphasizing the word 'might' as he made her hips jerk by slipping two of his fingers into her and caressing her flexing, intimate flesh. "Does it matter what you want?" he asked coolly applying slow circling pressure to her saliva slick clit with his thumb. "No." she answered on a rush of air. "Why?" he pushed in a low growl, his nose almost touching hers, his dark eyes reflected in her light ones. "Because... Because you... You own me. I belong to you and that... that means what you want is... is the only thing that matters." She answered, working her way through the words in stages and he finally believed she was grasping the full extent of her situation. "Good, Girl." He praised her like a pet that had done a trick, reinforcing her place in relation to him before he captured her lips with a probing kiss. He saw her eyes widen as she tasted herself on his lips and in his mouth as she almost unconsciously returned the kiss. It no longer seemed to matter though as she moaned and closed her eyes as he diddled her clit faster and with firmer pressure while sawing his fingers back and forth in her steamy, sopping snatch. She gasped and her eyes snapped open, flashing with betrayal as he suddenly broke the kiss and all contact with her, rising off the sofa to stand over her. Her lips parted, protest written on her face as she half-rose and then she abruptly shut her mouth and lowered her face in submission. "Take off the robe, get up on the sofa on your knees and lean forward against the back." He commanded and he fondled her buttocks as she complied with only a slight hesitation. Despite having had two powerful climaxes already, his dick had been hard and throbbing with need since he had tasted her. He freed himself from his pajamas and leaned over her, circling his tongue on her shoulder blade. "I'm a man of my word, Jenny. I'll give you what you want." He purred in her ear and she turned her head to look at him, not quite masking her suspicion. His wicked grin was designed to in no way assuage that suspicion. He grasped the base of his dick and guided it between her swollen folds to her entrance. He grasped her hips and thrust forward, both of them groaning in unison as he filled her and she stretched to accommodate him. "I don't think I'm ever going to get tired of that." He commented on a slow exhalation of breath as he pressed against her ass and luxuriated in her flexing, twisting core as it flooded and adjusted around him while he nibbled and licked at her shoulder and neck. He smiled against her skin as she slowly rocked back onto him, using her hands on the sofa back to brace herself and spreading her legs a little further to allow him to go deeper. "Now you're getting the hang of this." He complimented her as they rocked together until he drew back and out of her. She craned her head over her shoulder to look at him again, the tips of her teeth just visible as they pressed into her lower lip. "Do you know what's going to happen next?" he asked quietly, stroking his dickhead through her folds and then a little higher. He saw her swallow heavily and then nod. He guided the pointed tip of his cock to the rosy starfish of her asshole. "Try to remember to breath and relax... It will hurt less." He advised as he felt her flinch slightly and her asshole tense at his touch. He thought she would protest one last time given her fear of anal penetration, but instead she simply lowered her head and he saw her fingers tense on the leather of the sofa back in response. He started to press forward, apply, slow, steady pressure and then backed off as his cock started to bend without any discernable headway. "Try to relax, Jenny." He repeated and tried again, grasping his cock closer to the head. He concentrated and pressed forward again until he felt her sphincter give slightly and applied more pressure drawing a whimpering groan from her. He wised he'd thought to position a mirror so that he could see her expression. He was almost about to give up when his forward progress once again stalled, thinking it might be physically impossible or that she would need preparation before he could enter her when with a sharp cry from her and a grunt from him, his dickhead suddenly popped through her tight ring and it was pulsing around his cock behind his flared. She mewled as she tried to adjust to his invasion, as shallow as it was and he stayed as still as he could. Her breathing was rapid and panicky and he could see her knuckles were white and her nails had dug into the sofa back. "God she's tight." He thought as he resisted the urge to thrust deeper into her to feel her on more of his cock, but instead he stroked her back and reminded her to breath. Her ass squeezed at him, trying to evict him. He doubted very much she was doing it consciously, but he thrust forward slightly to seat himself deeper. She whimpered and tried to move forward away from him and he tightened his grip on her hips to hold her in place. "It will only take longer that way, Jenny." He half-admonished her as he rocked his hips, going deeper, a quarter inch at a time. She made little gasps, cries, grunts and groans of pain and discomfort as he worked his way through her actively resistant flesh and into her rear. He showed as much restraint as he could, but her tight, rear sheath was an exquisite delight as it flexed around him in a pulsing grip that he couldn't stop himself driving the last inch into her bowel with a single powerful thrust that drew a sharp cry of agony from her. "Breath." He reiterated simply. "Sorry about that. Got a little carried away at the end there." He apologized after a moment as he heard her sniff back tears. She let out a sharp, out-of-place back of laughter and then groaned as her ass clenched around him with the vibration, which made him groan in response. "That's rich... Fuck that stung and it hurt and still kind of aches. It feels like you're ripping me apart." She noted as she steadied her breathing by taking deep breaths and letting them out slowly. "And I'm not done, yet, Pet. Not by a long shot." He half promised, half threatened in her ear as he ground his hips against her ass making her whine. "Jeezus, Chuck... Give me a moment... Please?" she asked, her voice modulating from pained anger to pleading and he was surprised to find himself having to bite back another apology. "You're so tight and hot back here it's a bit hard to resist." He admitted instead and reached around and started to lightly fondle he breasts and toy with her nipples. She started to squirm slightly and he felt her adjust to him, the pressure of her tight ass easing around him, if only relatively. He drew back slowly drawing a hiss from her, but no other protest. He rocked his hips slowly, enjoying the caress of her smooth pulsing flesh and the snug grip of her sphincter along his length. He increased the range movements until he was taking long, slow, steady strokes. She continued to make little sounds of discomfort, but they grew further apart until she was panting softly as he drove into her again and again. Despite how good it felt, he was in no danger of climaxing anytime soon and he was simply enjoying the slow build up of tension in his nuts. He leaned over her again. "I think it's time for you to do some of the work, J." he whispered in her ear, nipping at her earlobe for good measure as he took his hands of her breasts and grasped her hips once more. He drew back and when he thrust forward, he guided her back. She grunted, but it only took one more demonstration for her to get the idea. "That's it." He encouraged as she rocked back to impale herself on his thick, throbbing shaft, her firm ass jiggling with the impact. He reached around and found her clit and started rubbing and rolling it, as he picked up the pace and she matched him. She gasped and started to make soft, breathy cries that held no hint of pain as he diddled her clit with his thumb and slid two of his fingers into her hot, steamy snatch and sawed them back and forth in synch with his cock delving the dank depths of her ass. He could feel himself inside her as her vagina fluttered around his digits. It was wicked and it quickened the pace of his building climax. Chuck used his free hand to turn her face until with a little effort he could capture her lips for a short, but intense kiss, gratified when she returned it with matching hunger. He kept his face near hers as he ground against her ass. "I said I would give you what you want, My Little J. You want to feel good... don't you? You want to come, like you did before. I want that too, Jenny. Don't get me wrong. I like it even more when I come, but you are a magnificent sight when you do. You never in your wildest nightmares thought it could happen, did you? Not with me balls deep in your ass, that forbidden place, that is now becoming a dark pleasure. You're surprised, maybe even a little ashamed, but you can feel it building, growing deep inside you, and threatening to erupt. Let it, Jenny. Just let it." He breathed in a low, coaxing, intimate tone as he drove into her harder with both his cock and his fingers. "Chuck... You're a bastard." She moaned with a lot less venom than he had expected as he made her body betray her again and her snatch clutched at his fingers and flooded around them with liquid heat as she came with a hoarse, stuttering cry. Her back arched and she inadvertently slammed back onto him with a sharper cry as she shuddered. He felt a surge in his own desire and with the need for restraint removed he started to make furious use of her ass with a need of his own. He pulled her toward him by the convenient handholds of her shoulders as he thrust into her with fast, forceful thrusts. He no longer cared if her cries were from pain or pleasure as he drove himself toward climax. She offered him a modicum of co-operation, bracing herself as he slammed into her and sooner than he would have thought he found himself on the brink. He jack-hammered into her, thrusting with his feet and all his weight, trying to get deeper into her, driving the air from he lungs in heavy grunts as his ass clenched and he gritted his teeth, straining to hold on and enjoy her for just a few moments more. Chuck was breathing hard through his nose, his chest feeling hot and tight as if he'd been running a marathon or in the fourth quarter of a basketball game. His dick was on fire, each stroke a delicious torture as her still tight, buttery flesh gripped and dragged at his sensitive shaft and sending sizzling sparks of pleasure snaking into his loins to curl and twine around his balls to add to the tension building there. He ground against the firm globes of her ass, buried as deep as he could when she tensed with a whining cry, her blonde head thrashing from side to side and he could see her arms trembling violently, her grip on the sofa back, so hard her fingers shook. He would have laughed with satisfied glee if the sweet pressure of her rear sheath didn't relax and tense around him in rapid succession. And, instead, his head was suddenly thrown back as he roared his release to the ceiling. His ass cheeks relaxing and tensing as the small of his back twitched and his spine bowed to keep him pressed firmly into her as he pumped his seed into the furnace of her bowels with stabbing spikes of pleasure cascaded across his system. One minute he felt like the most powerful man in the world and the next he could barely stand as his orgasm ran it's course and took his strength with it. He slumped forward onto her back, feeling his legs tremble and twitch and she collapsed forward as well, the sofa tipping precariously for a moment, but then righting itself. His chest heaved, pressing into her smooth back and he could feel sweat between their skin and trickling down his back. Chuck mustered his strength and straightened with a groan and then hissed as he pulled out of her the friction now more painful than pleasurable on his sensitized, shrinking penis. Jenny grunted and whimpered softly as well as she remained draped over the back of the sofa. He was surprised at the well-used ache in his muscles and fleetingly wondered if Jenny would be any good as a masseuse. He sat down and after a moment pulled her to him and into his arms, half on his lap. She complied without protest, groaning as she straightened out, her eyes closed, her chest slowly rising and falling, her breasts glistening with sweat, their pink tips still hard. He could see the tracks of dried tears on her cheeks. He leaned forward and bowed his head, while lifting hers until he could each her lips. He kissed her slowly softly until her mouth opened under his urging and his tongue danced with hers. He raised his head and let hers fall back as well and she blinked open her eyes. "I hope you got at least some enjoyment out of that, Jenny, because I am going to have to tap that sweet ass of yours on a regular basis whether you did or not." He informed, casually fondling her breast with his hand and her nipple with his thumb. Jenny was quiet for a moment, squirming her hips and shifting her legs. "It still feels like you're still in there. It's... It's strange and... and squishy and slippery and uncomfortable." She noted with an introspective little frown creasing her brow under stray tendrils of her pale, blonde hair. "You came again while I was really fucking your ass, didn't you?" he enquired and she turned her face a way from his, but not before he saw the truth in her eyes. He chuckled. "It's okay, Little J. We're going to do lots of things that will make you feel shameful for enjoying them." Chuck absolved her and promised at the same time. "Fuck you." She mumbled petulantly and he smiled. "Maybe in the morning. The spirit might be willing, but the flesh is weak." He responded, pinching and pulled her nipple, making her turn back to face him. "A quick shower to rinse off the sweat and... what hasn't leaked out onto the sofa, and then to bed." He told her. "To sleep." He clarified as he felt her tense. She raised her head and sat up slightly, spreading her legs and pulled a face of disgust at what had puddle on the leather between them. "Yeah... Goodwill will know how to deal with the stain and the holes. They'll still be glad of the donation." He commented. "Holes?" she asked confused and he directed her gaze up to the eight crescent shaped holes her nails had managed to make in the leather. "Oh." She muttered with embarrassed understanding. "I thin we better take that shower separately as well. I seem to have a hard time, pun intended, not molesting you when you're all wet. He suggested, letting his hands slide over her smooth flank, dipping into the valley of her waist and then up onto the rise of her hip. "You first." He stipulated with a nod of his head in the direction of the bathroom. "Thanks... I feel kinda dirty." She said before she rose slowly, swinging her legs to the floor with care. They had made quite a mess of the sofa. "Get used to it." He commented under his breath, but just loud enough for her to hear. She said nothing more, but grunted as she got up and took a few gingerly steps. Grimacing slightly. She stopped when he called her name and turned back toward him in time to catch the robe he tossed to her before disappearing into his bedroom. He pulled his pajama pants back on and got up and poured himself a fifth of Scotch. He called maintenance to remove the sofa in the morning. They knew better than to ask any questions beyond when it would be convenient to do so. He did wipe up the worst of the mess with a couple of paper towels, which he disposed of in the trash before settling down in his recliner to sip his drink and contemplate just how much of a bargain he'd gotten with Jenny Humphreys. TO BE CONTINUED...