This is a story about characters from the television show Gossip Girl. It is a work of fiction and the author does not claim any knowledge about the private lives of actors Chase Crawford, Pen Badgley, and Ed Westwick, and this story implies nothing about their sexuality. I do not own these characters, adapted for television by Josh Schwartz and Stephanie Savage and produced by CSB Paramount Network Television, Warner Bros. Television, College Hill Productions, and Alloy Entertainment.
Chuck Bass laid in his king sized bed in his suite in his parent's hotel, the Palace. Next to him, sleeping Nate Archibald actually looked like an angel. Chuck could see why Nate was the subject of every boy and girl on the Upper East Side's wet dreams. But Chuck was spoiled. He'd conquered Nathaniel Archibald, future business tycoon/United States presidential candidate, and he'd made him his bottom bitch. Chuck wanted a new challenge. And he knew just who was up for the challenge.
Dan Humphrey. Dan was a nobody, a pauper really. His dad played in some never-was rock band in the 90s and he lived in Brooklyn for God's sake. Then why did Humphrey have such balls? While Nate followed Chuck blindly, Dan stood up to him. Hell, when Chuck tried to take what he wanted from little Jenny Humphrey, Dan's sister, Dan actually hit him. Hard. Thinking of it, Dan placed a hand on his swollen black eye. It hurt, yes. But Chuck was fucked up. It made Chuck want Dan. Despite Dan's entrenched poverty (Brooklyn!), it also didn't hurt that he had innocent brown puppy dog eyes, cheek bones that never quit, and a pouty mouth that any girl would kill for.
Even though he had just fucked Nate, thinking of Dan made Chuck's dick stand at full attention and salute. The fat joint he had just smoked alone while Nate slept only added to it Chuck nudged Nate awake. Nate pushed Chuck away, struggling to cling to sleep. Chuck started nibbling on Nate's ear and neck, seducing him awake. Soon, Chuck was giving Nate a wake up fuck, but his thoughts were not on the youthful beauty under his body. No, he was thinking of his next conquest.
Dan Humphrey at first seemed like a difficult project. He hated the rich and he had no friends that Chuck could exploit. He wasn't into sailing or sports or money or anything else relatable. Plus, there was the fact that he had punched Chuck in the face. Chuck knew Dan had nothing he could work with to get in close to him. So then Chuck realized that he could work with what Dan didn't have. Unlike every other boy at St. Jude's School for Boys, Dan Humphrey was not born with a silver spoon in his mouth and a guarantee of an Ivy League education. That was the entire reason he attended St. Jude's instead of some public school in the barrio Chuck decided Dan lived in. With Ivy Week, when representatives of the Ivy League would come to visit St. Jude's, coming up, it would be the perfect chance to exploit the class difference between them.
Dan was in his room reading "Being Dead" by Jim Crace. He loved the honest, gruesome depictions of death used by Crace. This week, he had mean Serena Van der Woodson, almost gone on a date or two with her, and found out that she is just as shallow and empty as everyone he goes to school with. He couldn't stomach romance right now, but he could handle decaying flesh.
He was listening to Johnny Cash. Normally, Dan liked to be above the cutting edge with music. Everything everyone else listened to was so mainstream and devoid of soul. But he had to admit that nothing the post-modern, post-emo bands were cranking out could touch his pain quite like the Man in Black.
Dan's dad came in the room. Without knocking. Dan's dad handed him the phone and told him "It's one of your friends from school." Dan paused before saying anything. He didn't have any friends at school.
"Hello?" he asked, a little confused as to who would be calling.
"Daniel," replied Chuck on the other end. Dan recognized that voice anywhere. He should have known it was a trick. As he was about to hang up, Chuck pleaded, "Wait, don't hang up!"
Dan was kind of intrigued. "What do you want Chuck?"
"Look, after you shoved me at brunch, which you weren't even invited to by the way, my dad pieced everything together and realized that you gave me the black eye," lied Chuck. As long as Chuck stayed out of jail and the newspapers, Bart Bass could care less about his son. He was too busy chasing America's Next Top Model from a few seasons back.
"You're dad figured out everything?" Dan asked. "So he knows I punched you because you tried to rape my little sister."
Chuck paused. He reminded himself that he liked the challenge Dan presented, and killing him would make it more difficult, though not impossible, for them to sleep together. "OK, so maybe he doesn't know everything. But he wants me to make it up to you."
"And how are you going to do that?" Chuck snapped. "Kill yourself?"
"Why if I did that, Humphrey, I couldn't help you, now could I?"
"What could I need from you?" asked Dan, annoyed and genuinely unable to think of anything.
"A future for starters. I understand you have lowered yourself to matriculate with us trust fund babies so you could have a chance at the Ivies. Well it takes more than being second-in-the-class, and you know it," explained Chuck. Dan hated to admit it to himself, but Chuck had him. Chuck continued, "To make up for whatever transgression I have made against the great Humphrey household, I'm willing to help you figure out a way into the university of your choice."
In spite of himself, Dan was intrigued but suspicious. "And how do you propose to do that?"
"You know better than anyone that I take advantage of whatever comes my way. I'll teach you how. My place at the Palace tomorrow at 9 at night. The bellhop will show you up, or something." Chuck hung up before Dan could answer. He knew Dan was trapped. And Chuck didn't have time to waste with pleasantries, for he had homework to do.
Not, not algebra or chemistry. Chuck had to study the indie boy to prepare for Dan. As deep as Dan thought he was, he was really exactly like millions of other kids who shopped at vintage stores. Chuck spent an hour reading random livejournals and MySpace blogs. Then he half-read reviews of Vonnegut on wikipedia. He figured an hour and fifteen minutes was all the effort that he needed to put into Dan Humphrey.
Sure enough, there was a knock on his door at 9:05 the next night. Dan was intentionally five minutes late to try and prove his independence. Cute and futile, Chuck thought. Chuck answered the door. There stood Dan with a backpack and a few folders. This was going to be fun, Chuck thought.
He let Dan in and Dan rambled for a bit, trying to show his dominance. Dan was either nervous as hell or really liked to hear himself talk. Whatever, Chuck tuned him out. He was high as a kite. Dan sat down on the couch, and Chuck sprawled out on his bed. His robe rested high on his thigh, but Dan didn't notice, going on and on about school.
Not exactly sure what Dan was talking about, Chuck joined in and said it was like what Vonnegut said. Dan was shocked and silent. "You read Vonnegut?" Dan asked. Chuck quoted a few themes he had committed to memory from wikipedia. Dan took the ball and discussed how relevant Vonnegut was. Poor boy, he actually thought they were bonding.
Chuck got up and sat next to Dan on the small couch. Dan looked a little uncomfortable, and Chuck draped his arm around the back of couch. Dan looked down and noticed how short Chuck's robe was, and he possibly became aware of the possibility that Chuck was not wearing anything under it. Dan stuttered a bit and lost track of his thoughts. Chuck noticed that Dan was squirming uncomfortably, trying to discreetly adjust his growing erection in his pants. He wasn't sure if Dan was gay, bi, questioning, hypocritically turned on by money, or just really into Vonnegut.
Chuck jumped into the conversation. "I have a confession man. I really admire you." Dan gave him a look like Chuck was laying it on a little thick, so Chuck explained, "I know I'm lucky to be this rich, to have this privilege. But all I do is fuck it up. And you have to fight for everything you've got. I wish I could be more like that," Chuck lied.
The boys sat there for a second. After a moment, Dan decided that Chuck was seriously and choked out a thanks. Chuck then asked about Serena.
"That's pretty much done" explained Dan. "I thought she was different than a lot of the spoiled kids. But it turned out that she was the worst one."
"Spoiled kids," Chuck repeated, doing his best to act genuinely hurt. "Like me."
Dan actually felt bad for hurting Chuck's feelings. He made eye contact with Chuck. "Well, turns out that you're not all bad."
Chuck leaned in and kissed Dan on his soft, full lips. Dan pushed him off. "What are you doing?" Dan demanded.
"Sorry. I just thought that we were really bonding over breaking free and being individuals. I just wanted to do something that I wanted for once, not something everyone else wanted for me," lied Chuck through his teeth.
Dan looked down, confused as to what to do for a minute. Chuck seized the opportunity to lunge forward and kiss him again. This time, Dan didn't fight. Dan opened his mouth, and he felt Chuck's tongue enter. Their tongue's danced as Chuck ran his hands through Dan's dark hair. Chuck had actually worked for this lay, and he was voracious. He pulled Dan's sweater over his head and began kissing his neck. Dan had never felt like this before with anyone. Dan had never even been with anyone before. He couldn't think clearly, and acted purely on impulse. He put his hands on Chuck's robe and pulled it off. Revealed there on the couch biting his neck was Chuck's sinewy naked body. Feeling the cold air on his skin, Chuck looked up into Nate's eyes and kissed him hard, before pushing him back against the sofa. He moved his way down, nipping at Dan's earlobe, licking his neck and finally gnawing at his erect, pink nipples. Dan was in ecstasy; here was a guy he thought he hated sharing forbidden pleasure. It was so...deep. The teeth on his hard nipple felt amazing, too.
Chuck moved away from Dan's smooth chest and nibbled his way down Dan's smooth, flat stomach. He got to Dan's belt and undid it like a pro, and then he seemed to unzip Dan's pants and pull them off in one motion. Dan lay on the couch in a pair of black briefs, his hard dick struggling to push free. Chuck took a minute to take in the sight, but just a minute. Chuck was, as always, horny. He yanked off Dan's underwear and Dan's massive tool, now freed, sprung up and almost hit Chuck in the face, giving him a matching black eye. Chuck inhaled the manly scent and wrapped his lips around the head. Dan groaned with pleasure. Now he understood why all the guys at school only talked about sex. Chuck teased Dan's cockhead with his tongue while playing with Dan's balls. Dan whimpered above him, forgetting all about class differences and unjust college admission process. All he knew was that Chuck Bass gave the best head on earth. Chuck stopped going easy on Dan, and started stroking Dan's dick with one hand while slurping it into his mouth. Dan put his hands on Chuck's head, and Chuck let him pretend that Dan was in control. Soon, Dan was panting, and he was scared that he might cum too soon (and he never wanted this to end), so he pulled Chuck up to him and kissed him.
They rolled around on the sofa, and soon came crashing to the ground. They both laughed like old friends when this happened. Dan kissed Chuck lightly, and then his face became very serious. He pushed Chuck onto his back, and moved his face in front of Chuck's cock. He breathed Chuck in, and closed his mouth over Chuck's member. Damn Humphrey was good, Chuck thought. He started bucking his hips, forcing his cock down Dan's throat, but Dan could take everything he gave him. Chuck thought that maybe this wasn't Dan's first time.
Leaving his dick in Dan's mouth, Chuck crawled so that he was under Dan. Dan was now on all fours, slurping on Chuck's cock, and Chuck was under him, Dan's legs on either side of his head, with his dick down Chuck's throat. As the boys 69'ed, Dan began to buck his hips back and forth, feeding Chuck. Chuck braced himself, putting his hands on Dan's ass cheeks. Slowly, he inched a hand closer to Dan's hole and he stuck a finger in while Dan's was on top of him, facefucking him. Dan tensed up and pulled his mouth off of Chuck, "Whoa, whoa!"
Chuck pulled off Dan and assured him, "Don't worry, I won't do anything to hurt you." Liar. But Dan was lost in the lust of his first time, and the finger did feel good. They went back to sucking each other, and Chuck reinserted his finger. Dan started moving his hips back to meet the thrusts of Chuck's finger. The sound of the teenage boys slurping each other's cocks and moaning filled the room, and the sounds only got louder. Chuck had Dan's cock buried down his throat, and Dan was working his tongue up and down Dan's shaft.
The whole experience was new to Dan, but he soon felt the familiar build of cum in his balls. Chuck was fucking him hard and fast with his finger while Dan's huge dick was buried down Chuck's throat. Dan began working his tongue faster up and down the length of Chuck's cock. Suddenly, Dan felt weak in his knees and almost collapsed onto Chuck under him. Chuck jammed his finger into Dan hard and he could feel his balls release their load. It fired out of his dick fast, spraying the back of Chuck's throat. Chuck pulled off the dick and it sprayed him on his cheek and lips before oozing the rest of the hot, creamy load onto his face.
Lost in orgasm, Dan started deepthroating Chuck furiously. All of this pushed Chuck over the edge, and he unloaded in Dan's mouth. Jet after jet sprayed onto Dan's tongue. It was creamy and salty at the same time, and was the best thing that Dan had ever tasted. The cum flooded Dan's mouth, and it was soon dribbling out of his mouth.
Dan collapsed and crawled up so that he was face-to-face with Chuck. The boys kissed deep, tasting each other, and then Dan licked Chuck's face, cleaning his seed off of it with his tongue. The boys lay there on the carpet, young, spent, and warm, Dan wrapping his arms around Chuck and feeling closer to him than he had to anyone. Dan's first urge was to overanalyze how quickly his feelings for Chuck had changed, but for once in his life, Dan decided to just let things be and not think them to death.
They laid there awhile, Dan thinking he'd found his soul mate and Chuck thinking he'd found a new boy with untapped potential. Dan kissed Chuck's forehead, and then he moved down to his neck. Chuck felt Dan's hot dick, hard again and poking into him. Even Chuck admired Dan's recovery time. Soon they were rolling around on the floor, probing each other's necks with their tongues.
Dan came up for air and asked, "Do you have any lube and a condom?"
Chuck was almost taken aback by his eagerness. He had defiantly struck gold with this one. He reached into the pocket of his robe on the ground next to them and pulled out some lube. "Condoms are for commoners."
Dan wasn't quite sure what that meant, but he trusted Chuck. He got off the floor and pulled Chuck onto the bed with him. The boys rolled around some more making out, and Dan applied some lube to his fingers. He pressed them to Chuck's ass, and Chuck shivered with the cold sensation. Dan inserted two fingers, and Chuck began wiggling with pleasure as he bit down on Dan's neck. Dan increased his rhythm in and out of Chuck's ass, and Chuck bit down on his neck faster and more furiously. "Fuck me Humphrey," Chuck whispered very confidently into Dan's ear.
Dan wasn't exactly sure about the logistics, but he was eager to figure it out. Chuck rolled over onto his back, and Dan kneeled between his legs and lubed up his dick. He looked down at Chuck, whose soulful eyes and slim frame lay exposed and vulnerable. Dan had been wrong about Chuck Bass, he was sure of it. It seemed that Chuck was not the devil. Plus, Chuck's huge hard cock sprouting from his dark pubes was a total turn on. Dan worked some lube into Chuck's ass with his fingers while using his free hand to slather lube all over his own trembling prick.
Chuck wrapped his skinny legs around Dan's waist and pulled him forward indicating that he was ready. Dan looked down at Chuck's whole and lined his Dick up with it. He looked into Chuck's eyes and leaned forward, penetrating Chuck. Chuck closed his eyes and groaned at the intrusion. It was unlike anything Dan had ever felt before, and he pushed in further to have the feeling over more of his cock. Chuck was tight and warm, and Dan slid his cock in as Chuck continued to moan and writhe under him. Dan pulled out a bit and heard Chuck sigh. When he pushed back in, Chuck clenched up again, tightening around his dick. Dan started pumping his waist back and forth, trying to cram as much of himself into Chuck as possible. Soon Dan was jamming his dick into Chuck, making the sinewy boy tighten, and then Dan would pull out. He would take his dick almost completely out of Chuck's hole and then slam it back in, pounding Chuck. This got faster, and both boys began moaning incoherently. Chuck reached down with one hand and stroked his own big member, furiously rubbing up and down the length. He clawed at Dan's chest with his other hand. It surprised Dan and it hurt a little, but Dan soon realized that it hurt in a good way. Soon, Chuck got a hold of one of Dan's nipples, and he tweaked it, making Dan's weak in the knees. Meanwhile, Dan was still slamming into Chuck, widening the boy's hole, feeding the boy his meaty rod all the way. Dan was pounding Chuck's steamy, slick hole with an increasing pace, as Chuck whimpered, vulnerable beneath him. Chuck had given up on games; he couldn't concentrate anyway and he was enjoying being taken.
Soon, Chuck felt the build in his balls and jerked himself harder as Dan continued to pound away, slamming him with the full length of his dick. Chuck tried to utter something but could only moan as he worked spurt after hot spurt of cum out of his young dick. He sprayed on both boys' stomachs and chests and a lot of cum hit the arm he was jerking off with. The first jet even hit Chuck's chin. Chuck collapsed.
Dan continued pounding, and was about to come. He pulled out almost all the way and pushed back in so that his balls slapped Chuck's ass. He then felt himself unload, as he shot a torrent of hot, sweet boy juice up Chuck's steamy hole. Chuck shook as each steamy stream blasted his insides. Dan collapsed on Chuck as the final drops ran out into Chuck's stuffed, sticky ass.
Dan pulled out and crumpled next to Chuck on the bed. The two kissed gently for a few minutes, without even wiping the cum off of each other. Then Dan remembered, breaking through the post-sex glow that he came over in the first place for Chuck to give him tips on admittance to the Ivy League. "Hey, what about that stuff you said about the Ivy League?" Dan asked.
Chuck had forgotten all about it, and scoffed without thinking, "Seriously? That was to get you here. You think I know anything you don't?"
Dan was crushed. The romantic art film between him and Chuck that he was writing in his head was ruined. "What?" he asked, trying to hide his hurt, "You're kidding right?"
"Well it got you here right?" admitted Chuck. He had enjoyed Humphrey's company more than he had expected to. On instinct, he tried to maintain his cold exterior by pushing Dan away before he got too close.
It worked. Dan stood up, on the verge of tears. His virginity was supposed to be something special to him, and he gave it to Chuck who embodied everything he hated. He betrayed everything he stood for only to get betrayed. He pulled his pants and shirt on and almost ran out, refusing to give Chuck the satisfaction of seeing him cry.
As Dan slammed the door behind him, Chuck laid still in bed, convincing himself that he was satisfied with how everything had gone according to plan. He was lying to himself.
That's it for this time guys. Let me know what you think and if you want me to continue! xoxogossipguy@hotmail.com