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 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.
Spotted: N leaving B's place Friday night and heading to the Palace right after S was seen leaving the hotel bar. But just because N struck out with B doesn't mean he won't score tonight. Wonder what C is up to on his Friday night? You know you love me.
xoxo-
GOSSIP GAY
Chuck Bass was in his suite in the Palace, the Upper East Side hotel that his parents owned. He sat at his laptop, perusing. Serena Van Der Woodson, a conquest that he had never managed to conquer, was back in town after a year at boarding school, and he had failed to reach base camp again. He had decided that for the night, he was too sick of actual interaction to score with another person, so he was in his multi-million dollar sweet searching for the right porn to give him and little Chuck the right pick-me- up. But what would it be tonight? Girl-on-girl, guy-on-guy, guy-on-girl, guys-on-girls, or guy-on-goat? Being a privileged teenage son of the idle rich meant that Chuck could not confine himself to only one sexuality, because his money and power meant that it would get old quickly. The fact that he was the biggest pervert in Manhattan also added to this. Chuck liked a wide buffet of sexual options. A fornication pyramid, if you will, sometimes literally.
So Chuck sat at his computer with his designer pants undone and pulled down to his designer shoes and designer socks and his designer shirt and designer tie undone, revealing his designer undershirt. If anyone else had been present, they would have marveled at this boy's wiry body, and especially at his rock hard cock, which stood tall from a patch of dark pubic hair.
Just as Chuck settled on the idea of guy-on-guy porn for the evening, he heard the suite's door being unlocked. He didn't move, because not even his parents had a key to his suite in their hotel. No, the only person who had a key to Chuck's room was his best friend, Nathaniel Archibald. Sure enough, the door opened, and there stood Nate. He looked upset, but that only made him sexier to Chuck. His brown hair, normally perfectly styled, was disheveled. His soulful blue-green eye looked hurt and innocent. Chuck knew instantly that he wouldn't even have to put up a fight tonight with Nate.
Nate spotted Chuck and his hard member sitting at the computer. "God, Chuck what are you doing?" he asked.
"What does it look like? Waiting for you," Chuck shot back, only half-caring about how cheesy the line sounded.
"Great," said Nate sarcastically, closing the door. "But can we talk?" Chuck felt his dick growing softer at the idea of conversation with this boy-god instead of just fucking.
"What am I your girlfriend?" asked Chuck, annoyed. "Why don't you talk to Blair about all of your feelings?" Blair was Serena's best friend and Nate's girlfriend for as long as anyone could remember. Chuck thought of her as Nat's beard, as they had never had sex.
"That's the thing," explained Nate, obviously needing someone to unload on. Unload his emotions, unfortunately. "Blair and I were about to have sex. She was about to give me her virginity. And I told her about me and Serena having sex that one time. She blew up at me! What if I messed up everything with her and with Serena?"
Chuck was barely listening, and only to what he could use. "So your girlfriend is about to give it up and you tell her about the one time you had sex with her best friend. Sounds like you sabotaged yourself. Still, you must have blue balls. And for some reason, you come to my place..." Chuck trailed off, knowingly. He and Nate had fooled around with each other before anyone else. Together, they learned what was possible between two guys. Chuck's porn knowledge helped clue them in to some things they wouldn't have even thought of. After ruining his chances with both girls in his life, Nate was only at Chuck's for one thing tonight.
"Chuck, it's not that..." Nate protested.
"The lady does protest too much," Chuck quoted, badly. He spread his legs and began stroking his stiffening dick. He smiled and ran his tongue over his teeth, glaring at Nate. Chuck was vile, but he was sexy too. "C'mon Nathaniel, cut the bullshit and take what you want. It's what we do."
Nate knew that he was going to give in. Chuck glaring at him with smoldering eyes under his bushy eyebrows meant Nate couldn't look away, except to glance at Chuck's massive member. Nate walked towards Chuck, taking off his belt and unbuttoning his pants as he did. He pants and underwear dropped, and he stopped to take them off along with his shoes before walking over to Chuck. He unbuttoned his shirt and took it off with his undershirt. He now stood majestically in front of Chuck wearing only black knee high, gold-toed socks. He had the defined, hairless body of a Classical sculpture, and his face still retained the youthful innocence of a 16 year-old boy. He looked down pleading at Chuck who was still seated with a raging hard-on. Nate's own big dick sprung from a light cropping of hair, pointing right at Chuck's lips. Chuck looked into Nate's eyes, and leaned forward taking it in his mouth, never breaking eye contact. Looking up at Nate, Chuck slid it down his throat, watching Nate's mouth open to let out a sigh. Chuck then turned his attention fully to the task at hand, slurping back on forth on his best friend's dick. Nate noticed the still-lit joint in the ashtray next to Chuck's computer and picked it up, taking a few hits. It was strong stuff, and Nate swore that he instantly felt even sexier with his prick buried down his friend's throat. They had been doing this for years, and Chuck knew what drove Nate crazy. After deep throating the pretty boy, Chuck moved to Nate's hairless balls and gently licked them while stroking Nate's cock. He used his free hand to finger Nate. At parties and in sports Nate could pretend to be the alpha male, but Chuck knew that Nate loved things up his hole. Chuck swirled his tongue around Nate's balls for awhile longer, before returning his mouth to Nate's dripping cock. As he inserted a second finger into Nate's tight hole, Nate placed bother hands onto the back of Chuck's head and pushed it further down on his prick. While Chuck slammed his fingers into Nate, Nate fucked Chuck's mouth, getting slurped on every forward thrust of his hips and penetrated on the back thrust. Chuck brought his free hand down to pump his own throbbing cock.
Chuck knew the familiar signs of Nate's climax. His breaths got shorter and his ass clenched around Chuck's fingers. He pushed down faster and harder on Chuck's head. He widened his stance to support himself as he gave into the pleasure on his dick and ass. Finally, Nate screamed, "Oh God Chuck, I'm cumming!" Chuck pulled off of Nate. Like we said, Chuck is a dirty pervert, emphasis on dirty. He looked at his best friend's member as it twitched and began to unload on his face. It sprayed steaming hot boy juice all over Chuck's face. The first spurt hit Chuck's lips, and then his chin, neck, and shirt. Chuck would buy a new shirt. A little bit got in his hair. Chuck licked the sweet juice off of his lips. Chuck then stuck his tongue under Nate's dick, catching the rest as it drooled out before putting the cock back in his mouth and nursing it down. Chuck pulled off of it, and put his hand on Nate's back, pulling his friend down. They had a sloppy kiss as Chuck pushed Nate's sweet jizz into Nate's mouth and their tongues swirled around. Chuck broke the kiss and Nate began licking his cum off of his friends face.
Chuck stood up and kissed Nate hard, shoving his tongue down his throat. He smirked saying, "I'm not done with you yet." Nate smiled shyly. He knew what was coming. As they kissed, they took off Chuck's clothes. Both boys stood in front of each other naked (except for their knee length socks; they were gentleman after all), their smooth young bodies on the verge of manhood. Chuck smiled a cocky smile and pushed Nate onto his king-sized bed and pounced on him, kissing him hard on the lips. Nate reached his arms around Chuck's shoulders and pulled him in tight. Chuck reached into his nightstand and pulled out some expensive warming lube that was really just as good as the cheap stuff. While biting Nate's neck and nibbling on his earlobe, Chuck covered his hand with lube. He brought it to Nate's ass crack. Chuck's hands felt hot on Nate's hole, and he wiggled to entice Chuck to finger him. Chuck didn't need enticing. As he pumped two fingers into Nate, Nate jerked Chuck's cock with his hands, squirting some of the lube on it and rubbing it up and down the length.
The boys were horny and eager and Nate didn't need much loosening up, so soon he signaled that he was ready by wrapping his legs around Chuck's hips, pulling him. Chuck defiantly got the hint. Steadying himself above Nate with one hand, he used his other to line his cock up with Nate's lubed hole. He leaned in and kissed Nate hard on the mouth as he jammed his cock in. Nate howled with pleasure, being far less reserved than he ever was to the outside world or even his girlfriend. His legs tightened around Chuck's thin waist, pulling him in closer. Chuck knew he didn't have to be delicate with Nate, and he drilled away harshly at his hole. Nate's socked toes curled with pleasure and his dick was just as rigid as it had been during Chuck's blow job. Chuck pounded away at Nate's ass, his raw cock grinding into Nate. Nate's head banged against the headboard, but the pain was nothing compared with the pleasure that Chuck was giving him.
Chuck pulled out of Nate and rubbed his mushroom head around the outside of Nate's hole. Nate writhed, trying to get it back in. "Beg for it, Nathaniel," instructed Chuck, whispering into Nate's ear. He loved making this stud his bottom bitch.
Nate loved the freedom he had with Chuck, the only time that he felt that he didn't have to be stone cold. The pot helped, too. "Please Chuck," Nate began, "You know I need you in me. You know I need your raw cock filling me up."
As Nate continued to plead, Chuck turned Nate over onto his stomach. Nate buried his head into his pillow and presented his ass to Chuck. Chuck grabbed Nate's hips and pulled him close, impaling him on his prick. Nate and Chuck grunted in unison as Chuck fucked Nate doggy style and bareback. Chuck grabbed Nate's beautiful hair and pulled on it, using it like reins on a horse. Chuck was banging against Nate's prostate, and Nate's own dick was getting worked into the mattress as he was pummeled. He felt his balls tighten as he let out a succession of pleas. Chuck drove his dick in deep, and Nate grabbed the comforter for support as he wailed Chuck's name and for the second time in an hour, his dick fired piping hot cum out. It shot stream after stream over his six pack and down his chest, and stained the Egyptian cotton sheets.
Chuck reached under him and scooped Nate's cum up off his stomach with his fingers. As Nate tried to catch his breath and support Chuck's weight with his shaky knees, Chuck put his fingers in Nate's mouth, feeding him his still-hot seed and smearing some on Nate's lips. Nate licked the corners of his mouth to get it clean. Having his best friend cum from getting fucked and feeding him his own jizz always sent Chuck over the edge. Chuck placed both hands on Nate's hips and fucked him hard and fast, ever increasing in speed and force. His hips made a slapping sound as he shoved his whole length into Nate. Nate was mumbling something incomprehensible into the pillow below him and Chuck thrust one last time hard and deep into his best friend. Holding himself there for a moment, he unleashed a torrent of semen up Nate's tight asshole. Jet after jet splashed against the walls inside of Nate. It flooded out of Chuck and filled up his friend, and a little trickle ran out of the hole. Chuck collapsed on top of Nate, and Nate's knees gave out, as both friends crumpled onto the bed. Both boys were catching their breath as Chuck pulled out of Nate with a popping noise. He crawled down so his face was suspended about Nate's hole, and he licked his own cum up around it before driving his tongue into Nate's ass, cleaning it out.
His own cum tasted bitter compared to Nate's. Nate rolled over onto his back and pulled Chuck onto him. They kissed, and their orgasms subsided, this kiss was about actual emotion, not just animal urges. "Staying the night?" asked Chuck, showing a rare moment of vulnerability.
"Just for a few hours. Me and the Captain have to go running in the morning," informed Nate.
A few hours was better than nothing, and Chuck got up to get his joint from his desk. Back in bed, Nate spooned Chuck, holding him tight in his strong arms, and the friends passed the joint back and forth and kissed before falling asleep.