Bought And Paid For

TITLE: Bought And Paid For

AUTHOR: Midknight

CHAPTER: 7 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 SEVEN
He ordered breakfast for two from room service and then called Victoria Secrets from his mobile and in five minutes he had a private viewing room with items Danielle, his go to gal at VS, would select given his description of Jenny and her understanding of his preferences. Danielle had been a fun one night romp in the sheets with a pleasant surprise. Who would have thought there could be a lingerie model in New York that was beautiful, had a brain, a good personality and the sensibilities of an alley cat. He was sated for the moment, but the thought of her naked and wet in his shower tempted him to join her, but he decided against it. He pulled on a pair of silk boxers and his robe and waited for room service.

“Roger, How’re things?” He greeted the familiar, young bell hop that wheeled in the service cart. “Well, Mr. Bass. Thank you for those tickets to the ballet. My girlfriend really loved it.” He replied as he lifted the covers on several platters, filling the room with the mouth watering aroma of fresh croissants, bacon, eggs, sausage and other assorted dishes. “Did it get you laid?” Chuck asked and Roger grinned. “Like I said: Thank you very much for the tickets to the ballet.” He confirmed surreptitiously and Chuck laughed. “Coffee?” Roger enquired and Chuck nodded and the bell hop poured, black with one sugar, exactly the way Chuck took it. “Will that be all?” Roger asked after setting up two place settings. Chuck signed the room service bill and then grinned. “For me yes, but here’s a little something for you.” He replied, holding his finger to his lips to indicate that Roger was to be quiet.

“Jay? Jenny! Could you come out here, now!” He called having noted that the water had just been shut off. She came out with a towel wrapped around her while drying her hair with another. “What is it now, Chuck?” she asked and froze as she caught sight of Roger. “Roger here needs a tip and I just don’t have any cash on me at the moment, so be a dear and drop the towel.” He informed her, casually sipping his coffee as he saw her eyes widen and the towel fell from her hands. “Not that one, Sweetie. The other one.” He clarified unnecessarily as she remained frozen, her eyes darting from him to the perfect stranger he was asking her to reveal herself to her. “Chuck?” she made a simple appeal. “Jenny.” He used her name to indicate implacability on the subject and watched eyes drop and her shoulders droop.

His smile of amusement became one of genuine approval and grudging respect as after a moment she raised her chin, squared her shoulders and taking a deep breath, loosened the towel and let it fall to the floor. She stood still, her legs slightly apart, a defiant set to her full lips and made no attempt to cover herself. “Exquisite, isn’t she?” he asked Roger, hiding his smirk behind his coffee cup as he noted the front of the bell hop’s uniform now had a distinct bulge. “Don’t be shy. He makes a really good cup of coffee.” He encouraged her to twirl with a circling gesture with his free hand. He saw her eyes narrow with anger, her lips twitching to say something, but she complied and slowly turned, displaying her nudity to the bell hop. Despite her courage and defiance, he could see her skin heat and color with a blush of embarrassment. “That will be all.” He dismissed Roger after she made a complete circle. “Thank you again, Mr Bass. Miss.” Roger retreated, not taking his eyes off Jenny and touching his cap with a slight inclination of his head in her direction with an appreciative grin plastered on his face.

The moment the door clicked shut she reached down and grabbing the towel and clutched it in front of her. “Did I say you could do that?” he enquired, his tone cool. She held onto the towel, but let her hands drop to her sides. He saw her lip quiver. “Go get your robe, or stay el fresco, but your breakfast is getting cold.” He relented gesturing to the spread Roger had brought. “What does it matter?” She murmured barely loud enough for him to hear and dragged the towel along the floor as she headed toward him. He frowned. “It’s a choice… You should be grateful when I give them to you.” He informed her crisply. “He knows who I am.” she wailed and his frown only deepened. “He’ll tell someone and… and… eventually… I’ll be ruined. It’s over.” She explained, her voice rough and furry with the effort of choking back tears he could now see, standing unshed in her eyes.

He probably could have handled it better, but his hearty laughter did manage to bring the fire back into her eyes. “Oh my dear, sweet, Jenny… Nothing’s over. He won’t tell anyone. He knows better than that. Do you really think I would jeopardize having that sweet ass of yours at my beck and call for such a simple, uncomplicated thrill as having you give the help an eyeful? I’m almost insulted. I could turn his life into a living hell even easier than I could yours if he so much as uttered a word. Now, get over here and eat, we have an appointment at Victoria Secrets in an hour.” He explained away her fear as the utter absurdity it was. She turned slightly, looking back at the bedroom. “Drop the towel and sit down, the robe option is off the table.” He growled with a little irritation and set about getting his breakfast as she slowly, meekly complied.

Present day, the back of Chuck’s limo…

Chuck groaned and hissed with waves of pleasure that clenched his butt and made the tension in his balls spike as she buried her nose in his pubes and holding him snugly in the confines of her throat, rippled it around him by swallowing. Her head started to rise and he quickly changed his grip on her hair to apply pressure and hold her head and her pleasurable mouth exactly where it was. She resisted, struggling for a moment, more out of instinct than anything else, he thought as he challenged her to hold him deep for longer than was comfortable for her. He finally released her and to his surprise and her credit, she slowly dragged her lips up along his length instead of hastily retreating. She did give him a dirty look as she drew in a shuddering breath to which he just gave her an impudent grin as it didn’t really bother him as her fist continued to skim up and down his length. He raised an eyebrow to ask her what she was waiting for and she simply shook her head slightly before rolling her eyes and once again lowering her head and engulfing him in her wonderful mouth.

Several days earlier…

He walked up behind her and lightly placed his hand on her shoulder as he greeted her, his lips close to her ear in the crowded hallway at her locker. Using his body to shield the action from view, he slid his other hand up under her skirt and ran his fingertips lightly along the inside of her thigh to caress her naked sex drawing a soft squeak from her. “Very good. You got my text.” He complimented her as she tried to remain still and look natural as he massaged her folds amongst the swirl of passing students. “How does that feel?” he enquired, keeping his voice low and sultry. “It…It feels g…good… P…Please stop ” she stuttered and he saw her hand flex and grip the edge of her locker door hard as she squirmed slightly. He chuckled, the irony of her reply amusing him “You really need to enjoy yourself, but since you asked so nicely.” He commented as he removed his hand from her. “Room three oh seven… Lunch break… Don’t be late. You know how I hate being kept waiting.” He instructed, not giving her time to reply or acknowledge her understanding before stepping away from her and letting the sea of humanity that was the halls of Constance sweep him away to his own classes.

He rubbed his thumb across his fingers. They were slick and slippery and with a smile and a glance to make sure that no one was watching, licked Jenny’s cream off them. She’d been wet when he had first touched her. He had known it would both scare and excite her to have her come to school sans panties. He’d given her some time to get used to their arrangement, restricting his games to his suite, but now he felt like testing her limits. The room he had chosen for their rendezvous had a large bay window overlooking the quad, which would be crowded at lunch break and his classes seemed to drag and he was inattentive with anticipation. Nate even commented on it as they moved from one class to another and Chuck just passed it off as the affects of a hangover, it wouldn’t be the first time and Nate bought it without question.

Yet, when the time came, he sauntered up the stairs to the third floor. He peered around the corner at the head of the stairs to find her standing nervously at the door to the room he had specified, checking her watch. He waited a few minutes more and then briskly turned the corner. Her reaction was adorably comical as nervous tension gave way to relief and then spiked back to tension in a blink of an eye. “It’s locked.” She informed him as if to explain her loitering in the hall. “That’s what this is for.” He quipped as he produced a key from his blazer’s inner pocket and unlocked the door before ushering her in. “Why don’t you get a little more comfortable and take off you blouse and bra.” He suggested in a tone that made it no suggestion at all. She glanced at him over her shoulder and only reached for the buttons of her blouse once she saw him shut and lock the door. He removed his blazer and draped it over the back of the chair that accompanied the desk which was the only piece of furniture in the room as he walked over to the curtains that covered the window at the other end of the room. He casually slid his hand under her skirt to fondle her bare ass when he passed her. He surreptitiously adjusted his throbbing hard on for what little comfort he could get before pulling the curtains aside to reveal the large, single paned window, letting light flood into the room. The sill just barely came to midway up his thigh. He turned in time to find Jenny reaching around behind her to unclasp her bra. It was white and lacey, one of the pieces he’d picked out for her at Victoria’s Secrets.

“Very nice.” He commented as she dropped the undergarment on top of her blouse which already rested on the desktop. “Now come here.” He instructed, loosening his tie and the top button on his shirt. He watched her start to comply and then hesitate as she noted the window and what it looked out over. With, the position of the sun and the shadows of the surrounding buildings there was no way someone could actually see anything happening at the window, but she didn’t know that, it was something he was counting on. “Are you deaf or did I stutter?” he asked by way of repeating his instruction, letting just a touch of irritation creep into his tone, not that he was in any hurry. The sight of Jenny Humphrey’s, lithe, lush, nubile body in nothing but a tartan school skirt, knee high socks and shoes, and knowing that was all she was wearing was a sight to savor. He could see the worry in her eyes as they darted from his face to behind him, but she slowly stepped closer until she was standing in front of him.

Chuck casually unbuckled his belt. “Why don’t you get down on your knees, take out my dick and… do what comes naturally to a great cocksucker like you?” he told her in a calm, almost bored voice, although his dick had lurched in the confines of his boxers at the idea. He saw her spine stiffen at what he called her, but she slowly sunk to her knees. She undid and unzipped his trousers and fished his cock out of the fly of his boxers. Her hand felt delightfully warm and smooth as she wrapped it around him and slowly skimmed his length before grasping him at the base. She flicked her eyes up at him, a silent plea in her beautiful, big eyes, which he returned with a cool, unwavering stare. Finding her plea denied, she lowered her head and her sweet lips wrapped around his dickhead before she sucked him into her mouth. He couldn’t quite maintain his casual demeanor as the warm, wet pressure of her mouth slowly engulfed more of his throbbing member sending a shiver of pleasure up his spine, tightening his balls and dragging deep groan from his throat.

Her tongue swirled and slithered along his skin as she started bobbing her head, not swallowing him, but letting him press into the entrance to her throat while her hand took care of the rest. Her technique and co-ordination were increasing each time he had her blow him and he briefly wondered if she even realized she was honing her raw talent. His anticipation throughout the morning caught up with him as he felt himself rather quickly reaching the point of release, but he hadn’t brought her here simply for a quickie blowjob. He wound his fingers into her hair and when next her head rose up, he tightened his grip and pulled her off him. She squeaked in surprise and pain as he dragged her up to her feet while deftly spinning her so that she was between him and the window facing out. He let go of her hair and grasped her shoulders as she started to struggle and try to back away from the window. Over her shoulder, he could see her panicked reflection overlaying the students merrily going on about their lunchtime business.

He shifted his hold to the nape of her neck to free his hand so that he could grasp the base of his cock and guide it under her skirt. Her struggle intensified and he slid his foot forward between hers before she could find the presence of mind to close her legs. Her fingers scrabbled at the glass as she tried to push away from it, but she couldn’t quite get the leverage she needed. His dickhead brushed through her folds, finding them swollen, open and slick. He smiled as he rubbed himself back and forth, enjoying the wet warmth, her struggles adding to his enjoyment. He found her entrance and seated himself, causing her to try and squirm away. “No, Chuck! Not here! Someone could look up and see!” she wailed.

Jenny cried out in pain as he roughly crushed her cheek and breasts against the glass as he leaned all his weight against her back and held his forearm across the back of her neck. “What did you just tell me?” he growled in her ear with anger that burned with cool fire and made her freeze. “I’m… I’m sorry… I… Didn’t… I…” She stammered and then cried out as he rapidly changed his position and with a rough, violent thrust drove himself into her ass instead of her snatch. He humped hard, two more jabbing thrusts to drive himself all the way into her tight resisting rear channel, drawing further cries from her. He pressed hard against her ass, feeling her clench and twist around him whether to adjust to his rough invasion or repel it, he did not care as he rested his weight across her back, his mouth next to her ear. He grasped her hips and drawing back slightly pulled her roughly back onto him again.

Chuck breathed heavily through his nose, his teeth clenched as he felt her shudder and whine as he circled his hips to his cock in her bowels. He didn’t know what felt better, the feel of her snug rear channel pulsing around him or the power he felt dominating her. He could see the shock and fear in her eyes and it pleased him. “You know why you’re being punished?” he asked, his voice a tense, ragged growl as he drew his hips back. She sniffed back tears and nodded, even as she grimaced as he slammed into her ass again. “You…Don’t… Ever… Get… To… Say… NO!... To… Me!” he ground out, emphasizing his words with a hard, brutal, full-length thrust, the slap of him colliding with her ass separating each word, driving the breath from her in heavy bursts that misted the window in front of her. “Say it!” he commanded. “I don’t… don’t ever get to say no to you.” She whimpered as he continued to grind into her.

“I can’t hear you.” He admonished and reached around to roughly maul her breast, squeezing her flesh before pinching and pulling her nipple causing her to gasp in pain. “I don’t ever get to say no to you.” She sang out in a loud rush and after a moment he released her breast. The hot friction of driving into her had his balls boiling and the sweet tension holding back his release heightened the anticipation of his climax. “Here’s hoping you’re not as fast a learner as I give you credit for, because I will love to keep teaching you these little lessons.” He told her as he lifted his weight off her back. “Now fuck me, and make it fast. I don’t want to be late for class.” He instructed, shifting to gave her enough room to maneuver. She looked at his reflection and the students moving about unperturbed and oblivious below them and he raised an eyebrow to ask what she was waiting for.

She took a deep breath and splaying her fingers on the glass, spread her legs a little further and pushed back and down onto him. He couldn’t quite stifle the groan of enjoyment as she build a steady rhythm and pace, impaling her ass on his throbbing, tingling cock with sizzling pleasurable friction. He had intended for her to do all the work, but as his climax built, he found inactivity impossible. He slid his hands under her bunched up skirt and onto the smooth curves of her ass cheeks, fondling the firm flesh before using it to pull her onto his thrusts as he added strength to her pace and rhythm. She grunted and whined, breathing hard as she exerted herself to meet his expectations. His eyes were half-lidded, his spine tense and occasionally wracked with shivers. His buttocks clenched as he resisted the urge to orgasm, wanting to make her work for it.

Chuck closed his eyes for a moment as she added a slow circling of her hips, corkscrewing onto him with exquisite pressure and then it was too much. His fingers bit into the smooth skin of her hips as he held her tight against him as with a soft cry and a series of satisfied grunts he pumped his seed into her dank depths. His hips thrust as his spine tensed and relaxed with the pulsing charges of delight created by each burst of release. He blinked as the back of Jenny’s head and his world went a little blurry as his sense processed the bliss of his release. She collapsed forward until she was sprawled against the expanse of glass in front of them and he followed her. They were both breathing heavily and it took him a moment to find the strength to take his weight back onto his feet. She stifled a cry and groaned, as he pulled free of her.

“You’re going to need to clean up. There’s a bathroom at the end of the hall. I’ll see you at my suite at four. Don’t be late or I might have to teach you another lesson.” He told her, waiting for her to turn so that she could see the look of delight on his face at the idea. She stared at him with silent anger, her lips twitching to say something, yet with the consequences he had just demonstrated unable to and under the onslaught of his smug stare, she wilted and her shoulders drooped in resignation. He watched her gingerly run her finger over her abused asshole to collect some of his seed that had started to leak out of it, a look of disgust on her face. “You might want to hurry. Lunch is almost over.” He prompted, as he used his handkerchief to clean himself up before tucking away his now sated and limp dick away. He tossed the monogrammed square to her. “Use it, keep it or burn it. I don’t care. He suggested. He straightened his clothes while she collected hers and dressed. He unlocked the door and after a quick surreptitious check of the hallway gesture her out of the room. “Four o’clock, and don’t be late.” He reminded her and she nodded meekly as she slipped past him and headed to the bathroom he had mentioned.

He watched the sway of her ass as she walked with what seemed exaggerated care. He smiled to himself. She would most likely still be a little sore by the time she got to his suite at The Palace later he concluded. His smile broadened and he reached for his mobile, having though of the perfect way to combine both the carrot and the stick in Jenny’s training.

TO BE CONTINUED