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 the actors 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. This episode takes place during Season 2 Episode 5 "The Serena Also Rise."
Gossip Gay 7 -- Limo Sex Redux
Spotted: Lonelyboy is lonely again. And what's this, is C possibly flying solo? Is it possible he has slept with every twink in the Upper East Side? With both boys flying solo and their ex-GFs way too busy playing frenemies to care, will C and Lonelyboy find comfort in each other's arms? I sure hope not, but they might find sex.
Dan Humphrey had come to Chuck Bass because he wanted a story. He had to find the most dangerous, destructive person he knew to try and get inspired by living a life the opposite of his. Dan was happy to think no one was more different than him than Chuck. And the night he had fucked Chuck had changed him unlike anyone besides Serena. Serena. His girlfriend, now his ex-girlfriend. They'd just broken up and all of his stories revolved around her. He was in a rut. He wanted to feel something new.
Chuck Bass was bored. Even after he'd broken up Blair and her blue blood boy toy, she wanted nothing to do with her. Even Nate seemed preoccupied with his new cougar and his very own charity case from Brooklyn. So when Humphrey came barging into his suite like an unwanted Vanessa Abrams, Chuck decided maybe it was time he too took on a project from across the Bridge.
Dan wanted a story. Chuck wanted entertainment. Both were full of shit. They had both been rejected from the only women they loved and wanted to feel something. And considering how good the last time had felt, Chuck and Dan thought that the other was the perfect stimulant.
A few hours into their night on the town, Dan was feeling a different kind of stimulant. He wasn't exactly sure what, St Jude's health class was clearly not up to snuff. But the pills Chuck had given made him feel alive. They made him feel sexy. They made him feel horny. Hornier than a sexually confused teenage boy with absentee parents normally feels.
The leather seats in the back of Chuck's limo didn't hurt things either. Dan ran has hands against the smooth black fabric and looked over at Chuck. Chuck leaned back in the seat next to him. Dan could try and deny all he wants, but the drugs and alcohol were actually cutting down on his bullshit filters: Chuck was smoldering. He had a refined look like someone from an elegant bygone era, and all it did was to mask how much of a smutty devil he was under a thin, thin veneer. Oooh, Dan had to remember to write that down for his story.
Chuck broke Dan out of his haze. Without turning to even look at him, Chuck asked "Are we going to fuck Humphrey, or are you just going to drool on my leather seats?"
Dan reached over with his hand, turning Chuck's head and kissed him hard. Dan was high and uncoordinated and messy. Chuck didn't mind. Drugs or not, Dan wanted him, and that enough to get Chuck at full mast. As much as he wanted it, Chuck made sure Dan understood who was in charge pulling on Dan's curly dark hair, kissing his pouty lips. Dan fumbled with his shirt, struggling to get it off. Impatient, Chuck just yanked if off for him. "Careful," Dan said. "If I rip it, I'll have the drive stop by a clothing donation bin and fetch you a new one." Dan kissed Chuck, partially to shut him up, partially because he couldn't help himself. He had to kiss Chuck.
Soon their clothes were on the floor, a pile of vintage stores and Madison Avenue at their feet. The naked boys broke their kiss and looked into each other's eyes. Dan loved Chuck's; they were predatory and dark like his intentions (another quote for Dan's story!). Chuck liked Dan's eyes too, because his pupils were dilated and he knew he could have his way with him.
Dan began kissing Chuck's neck, nibbling his way down Chuck's thin frame. The licked Chuck's hairy chest, biting Chuck's nipples. Chuck loved Dan without all his posturing and inhibitions. He was so happy he had that stick out of his ass, and he knew what he wanted to replace it. Dan soon found his way to Chuck's dick. It would be hard to miss, thin and long and hard. Dan wrapped his beautiful, full lips around the cockhead and began delicately making love to it. But Chuck didn't want delicate and he certainly didn't want love. He bucked his hips, feeding his cock to Dan while pushing his head down on it. Dan gagged, trying to swallow it all. He adjusted to Chuck's forceful motions, and was soon enjoying the sensation of Chuck burying his lengthy cock down his eager throat.
Chuck looked down at Dan, literally and not just figuratively. His beautiful enemy was enraptured with blowing him, his naked, built body on his knees worshipping Chuck's huge dick in the back of his limo driving down 5th Avenue. God, it was good to be Chuck Bass.
Dan was adjusted to Chuck's length now and handling it like a pro as Chuck drilled it into his mouth. Chuck was as forceful as he wanted, ramming into Dan's vulnerable, willing mouth, and Dan took it. What's more, Dan was moaning. Humphrey loved it. Last time, he had gotten to Dan with fake emotions. He had no idea it could be so easy and so fun to just get to Dan with hormones.
Chuck had to get his hands all over this guy. Tugging on Dan's hair, he got him on his feet in the back of the limo. Chuck ran his hands all over Dan's muscular body. Chuck ran his hands down Dan's strong back, and Dan shivered at the light, ticklish sensation. Chuck's hands came to Dan ass, and he grabbed the two plumb globes. Hands on Dan's cheeks, Chuck pulled Dan forward. The force as well as the shakiness of doing it in a moving vehicle caused Dan to fall on Chuck. He landed on his knees, straddling Chuck. The two boys passionately made out, Chuck forcing his tongue into Dan's mouth and Dan letting himself be taken. Chuck ran his fingernails over Dan's broad upper back, and Dan sighed into his mouth. Chuck's dick was pressing against Dan's tight hole, and the occasional pot hole caused intense friction for both of them. Dan's huge dick was rock hard too, poking into Chuck's slim stomach, as their bodies pressed together. Dan started wiggling his hips back and forth. The sensation was twofold; his own dick rubbed up against Chuck's pleasure trail, and Chuck's cock got wedged stiffer into Dan's crack. Dan moved his hips circuitously, so that his hole was circling Chuck's spear like prey. Chuck couldn't take it anymore, he was done with games (part of the reason he wasn't chasing Blair that very moment instead). He'd waited almost a year to fuck Humphrey, and if this foreplay felt so good, he couldn't wait to sink into his kill.
Chuck broke this kiss and both boys looked at each other, faces inches apart, breathing heavily. Dan leaned in for another kiss, and Chuck turned his head, reaching into the storage space in the door. He turned back to Dan with a smile. He was holding lube. Dan had his first clear thought in what felt like hours; of course Chuck Bass travels with lube within arm's reach in his limo. Dan certainly appreciated the planning, at the moment.
Chuck popped the cap off the lube and reached behind Dan. Suddenly, Dan shivered as something cold came in contact with his hole. It was a stark contrast to all the heat between him and Chuck. After a moment frozen, Dan started wriggling and writhing again, as Chuck rubbed lube all over his own dick and worked some into Dan's hole. Dan swirled his hips around, trying to get Chuck's finger deeper into him. Chuck obliged, le finger fucking Dan's vulnerable ass.
"Fuck me!" pleaded Dan, straddling Chuck's dick and biting his lip. Chuck loved where he had Humphrey, and not just over his dick. He loved having this beggar beg. Chuck jammed two fingers hard into Dan, pulling on his hair with his other hand, "You want it rough, Humphrey?"
"Yeah," moaned Dan, "I want tit however you want to give it to me." For the first time in their lived, Dan was speaking words that Chuck understood and approved of.
"Tell me you want me," after being under the thrall of Blair Waldorf for months, Chuck loved being in control, even if it was just a nobody like Dan Humphrey. At least he was a horny, high nobody with the world's best ass.
"Yeah, I want you in me deep Chuck," breathed Dan, rocking his ass back on Chuck's slick fingers. That was all Chuck needed to hear. He pulled his fingers out of Dan and before Dan could react he had jammed his dick deep into Dan.
"Fuuuuuck!" wailed Dan.
"Too big for you, Humphrey?" asked Chuck, sliding more of his length up the tight ass.
Yes, yes it was, but Dan was not going to concede. He was trying to live the life of Chuck Bass for a night, and Chuck would never let something earthly like physical pain get in the way of sex. Dan looked into Chuck's eyes. "Deeper," Dan commanded.
Taking it as a challenge, Chuck thrust madly into Dan and Dan shook with the force of each invasion. He wanted to scream out in pain, but he more wanted to scream out for more. When he tried, he just found himself gasping for air. Chuck recognized the noise of a satisfied lover unable to speak, and he dove harder into Dan. Dan stretched his arms out, balancing himself on with one hand on either side of the interior of the limo. High out of his mind with a huge cock fucking him in the back of a limo driving around the Upper East Side? Dan had no idea how much of a typical night in the life of Chuck Bass he was living.
Chuck did have to admit to himself how amazing Dan was. Then again, he shouldn't have bee surprised; the impoverished are always good at sex. It's why he so often seduced the help. Dan kneeling across Chuck squeezed his strong thighs together around Chuck's thin hips, keeping their bodies tight as Chuck plowed him. With all the ambivalence in his life, Dan loved someone just taking control. It his the spot, just as Chuck's long member was hitting the exact right spot deep, deep in Dan. Chuck shoved his cock all the way into Dan and with his arms on Dan's hips, held him down onto it. Dan froze for a moment, overwhelmed with pleasure. He trembled and felt his balls contract. A stream of cum shot up and out of his cock without jetting up and hitting Chuck on the chin, the neck, the chest. Chuck was surprised; he knew he was good but he hadn't even paying any particular attention to Dan's dick. The feeling of his hot boy juice spraying onto his face sent him over the edge. Still holding Dan down hard on his cock, Chuck unleashed a torrent of hot jizz into him, showering Dan's insides with steaming cum. It felt like an eternity of Chuck depositing up Dan, but finally he had finished. Not one moment later, Dan collapsed exhausted on Chuck on the seat.
Playfully, he licked the cum off Chuck's chin and neck. Chuck used a Hermes pocket square to clean the cum off of him. He didn't offer it to Dan. Chuck slid his clothes on, and Dan followed suit, talking incessantly. Chuck had had fun, but now he had a post-sex hangover, and Humphrey ramblings would not make it better.
Dan kept rambling, oblivious. For a few minutes at least. Chuck had the driver pull over, and there he dropped Dan off, without a phone, a wallet, or shoes. Now Dan really knew what it was like to be a part of Chuck Bass' life.