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 Penn Badgley, 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 chapter takes place after episode 1.08 "Seventeen Candles."
Spotted: Lonelyboy Dan and his girlfriend S getting nowhere in the sack. Meanwhile, C has been getting awfully friendly with his best friend N's ex-girlfriend B at her birthday. But maybe it turns out that N has a present for someone after all. Wonder whose candles he'll be blowing out. You know you love me... xoxo- Gossip Gay
Dan Humphrey had failed to seal the deal with Sabrina van der Woodson, the girl he had been drooling about since she said hi to him at a birthday party eons ago. They were dating and everything was going great. Everything but sex. He decorated his room with candles and hid his Cabbage Patch doll (not a euphemism, sick), but she could sense his trepidation and called it off. She thought he was nervous because he was a virgin, and she was very much not-a-virgin. He was actually nervous because he had lost his virginity to Chuck Bass days beforehand.
Regardless of the reason the two had decided to wait, and so Dan lay on his new sheets alone, stroking his cock. He could not stop thinking about Serena and her one- party-stand with school hottie, Nate Archibald. The more he thought about it, the more he realized he wasn't thinking so much about Serena but Nate and his billowing shirt. Dan did not know what his single sexual encounter with Chuck meant, and he was doing his best to suppress any burgeoning guy-on-guy feelings now that he and Serena were together. But he could not get images of Nate out of his head. His glassy eyes, his defined chin, his pink lips. Dan jerked his cock harder thinking about Nate. Nate was not sure how he felt about him and Serena deciding to wait on sex, but he wasn't thinking much of Serena at the moment. Serena who? He thought about all of the things he did with Chuck and thought about doing them with Nate. Was Nate aggressive? What are his sex sounds like? Was Nate's ass tight? What are his sex sounds like?
Imagining Nate moaning, a real life sound brought Dan back to reality. Someone was pounding on the door of his loft. Dan wanted to let whoever it was keep knocking, but he was home alone, and he figured that it was probably his friend Vanessa. Who had increasingly been invading his privacy. He glanced at his window and it was locked with the curtains drawn. Yup, Vanessa was probably using the door, unable to crawl in through his window. And he knew that she would never stop banging on the door until he talked to her, so casually put on pair sweatpants and walked out of his room and to the front door.
Dan figured he would answer the door, tell Vanessa he was doing homework and call her later. He opened the door and there stood Nate Archibald. Nate was even more beautiful than Dan remembered. He looked perfect standing there, like not a hair or thread was out of place. And he was holding flowers. Weird.
Nate looked just as confused. "Is Jenny home?" he asked nonplussed.
"Nope sorry," replied Dan. Why was this god looking for his 14-year old sister?
"Oh, I brought her these flowers," explained Nate, only confusing Dan more.
Dan had blue balls from his interrupted masturbation session and from Serena not having sex with him, and he wasn't thinking straight. Heh. Without thinking (with anything but his swollen member), he asked "Wanna come in?"
Nate looked at Dan. Dan was only wearing sweatpants, and all of his visible skin was glistening as if he had interrupted a work out. Dan's chest was heaving, and his body glistened beautifully. And inside Dan's tight sweatpants, it looked like he was packing some stiff heat. Nate forgot why he was at the Humphrey household. "Sure," he accepted without realizing he was talking.
Dan showed Nate in and realized that he had no idea what to say. He put the flowers in some water and asked, "So why are you bringing my little sister flowers?"
This interrogation brought Nate back to the conversation and away from thoughts of licking Dan's smooth pecs. "Oh," he began, "Me and my girlfriend, Blair? We broke up. And you saw in the papers that my dad is in trouble. Jenny talked to me about it. She really helped. I talked so long that I made her miss Blair's party last night, so I wanted to make it up to her."
"Really?" asked Dan, surprised. He couldn't believe that younger his sister was lucky enough to spend the night alone with this hunk.
"Yeah, well Chuck has been really weird yesterday. I tried to talk to him, but he just wasn't being himself."
"Well, Chuck is weird," noted Dan. He was still bitter about the way that Chuck had used him.
"You don't know him like I do," defended Nate.
Without thinking, Dan commented, "I know a lot about him."
"What does that mean?" Nate asked, confused. The two boys sat across from each other in the Humphrey living room. Dan looked away from Nate. Then it dawned on Nate, "You mean, you and him...?"
Dan blushed and he felt his entire body, exposed and embarrassed, turn red. Then he realized that if Nate was implying what he thought he was implying, then there may be more to the story. Dan asked, "Wait, did you and he..."
The boys made knowing eye contact. Nate cocked a smile. "For years now," he admitted.
Dan was shocked. He felt his dick grow harder in his sweatpants. The thought of those two hot boys together was sexier than anything he could cook up on his own while masturbating.
"What about you?" asked Nate.
"Just once," Dan admitted. "He was kinda an ass." He paused, and then corrected himself, "No, he was definitely an ass."
"Yeah," Nate agreed, "but it's such a cute ass."
The boys smiled. Neither had ever talked to anyone but Chuck about this before. "Did you like it?" Nate asked.
"Yeah," admitted Dan. "It was something I never thought about, but now I can't stop thinking about it." He realized he may have overshared, but Nate was still smiling at him.
"What about Blair?" Dan asked.
Nate looked away for a second, and replied, "Chuck gives me something that Blair can't. I'm not going to date Chuck. I'm not going to marry Chuck. It was just sex." Dan wasn't sure if this really made it alright to cheat on your girlfriend, but he was so charged up by Nate's presence that it didn't matter. He would use any excuse to touch this boygod. And Serena wanted to wait, since it was special with Dan, so why should she mind if he had meaningless sex with someone that she already had meaningless sex with?
"So, the only guy you've only been with Chuck?" asked Nate, pointedly. The boy was beautiful, but he was not subtle.
"Yeah," conceded Dan, not pointing out that he had also never been with any girl. "You?"
"Yeah," confessed Nate. "You thought about being with another guy?"
"I'd try it," Dan owned up and innocently asked, "You?"
Nate stood up and walked over to Dan. He leaned over and kissed him on the lips. Both boys were surprised by how gentle the kiss was; with Chuck it was always about force and dominance. This was tender, something neither had considered kissing another a man to be. Dan broke the kiss.
"What's wrong?" asked Nate, concerned.
Dan smiled, "Nothing. It's just the Humphrey household is basically a revolving door. Someone is bound to barge in any minute now." Both boys looked at the apartment's front door, half-expecting someone to barge in. When they didn't, Dan offered, sexily, "Wanna go to my room?"
Nate kissed him quickly and pulled Dan to his feet. Dan grabbed Nate's hand and led him to his bedroom, locking the door behind them. Dan turned to face Nate, and Nate had already taken off his own shirt. The two boys kissed sensuously, Nate wrapping his strong arms around Dan's body and Dan running his hands through Nate's hair. Their tongues danced, and their smooth chests were pressed up against each other. They stopped kissing and looked into each other's eyes, not even inches apart.
Then Nate dropped to his knees. He was at eye level with Dan's huge cock, struggling to break free from the sweatpants. Nate pulled them down, and Dan's stiff prick bounced right up in his face. Nate wrapped his lips around the head, and began bobbing his head up and down on it. Dan encouragingly put a hand on the back of Nate's head. He looked down and saw his dick disappear down Nate's throat. He couldn't believe that the hottest boy in school was on his knees in his bedroom blowing him. And Nate was good at it too. As Nate sensuously worked his tongue over Dan's shaft, Dan ran a hand through Nate's thick hair. Nate loved the taste of Dan, and did his best to work Dan's entire solid prick into his mouth. Dan moaned as Nate slid the cock deep down his throat.
Nate moved a hand to his fly and unzipped it. His pants dropped to his knees on the ground. He pulled down his Calvin Klein briefs, and wrapped his hand around his own stiff member. Nate began to work it with his hand to the same rhythm he sucked on Dan. Both actions increased speed as both boys got hotter and hotter. Nate put his free hand on Dan's ass cheek. He ran his hand over the cheek, feeling Dan's smooth skin. Dan shivered from the subtle sensation on his ass. Nate slid his hand to Dan's hole and pushed a finger in. Dan sighed and thrust his hips, forcing his dick further into Nate's mouth. Dan began bucking his hips, and Nate was sucking and fingerfucking him fast while he jerked his own prick. Dan got closer to cumming as Nate worked his finger deeper into his hole. The thrusting into his ass, the wet mouth lapping at his cock, and the thought of the hottest guy ever on his knees for him was sexier than ... well, anything he could think of. Ever-articulate Dan Humphrey couldn't think of any words besides faster, harder, deeper. Dan was tugging on Nate's hair, but Nate feel any pain; he was too wrapped up in the huge cock down his throat, the hot virgin ass he was fingerfucking, and his hand's tight grip on his own tool. Dan felt himself grow week in the knees and then everywhere. As Nate fingered his hole, Dan slammed his hips forward, jamming his rod down Nate's throat. With a sigh, he unloaded a huge load into Nate's mouth. Nate's mouth filled with blast after blast of Dan's jizz, spraying the back of his throat. Nate loved how it tasted, and he swallowed every hot drop.
After he had fired his load, Dan collapsed onto his bed, his chest rising and falling as he recovered. Nate crawled up onto the bed on top of Dan, naked but for his socks. He kissed Dan lightly on Dan's full lips. Dan then grabbed the back of Nate's head and pulled him in for a deep kiss, tasting his cum on Nate's tongue. They rolled around on the bed, Nate's rock hard cock poking into Dan's tight stomach. Even though he had just shot a huge load, Dan felt his dick getting stiff again. Boys will be boys. As they continued to kiss, Nate reached his hand back down to Nate's ass and worked his finger in again. The penetration made Dan's dick shoot right up again. He knew what he wanted.
He rationalized that Serena had been fucked by Nate, so why shouldn't he? Especially because Nate was dating Serena's best friend when they had sex. Also he thought about what Nate had mentioned about not feeling bad about cheating on Blair with Chuck, because he didn't want to marry Chuck. Dan rationalized that he didn't want to marry Nate either, so there is no harm, even though he would probably marry Nate if he keep on working Dan's hole. Mostly though, Dan was only thinking about one thing: "I want you to fuck me," he stated directly.
Nate was a little surprised. As he stammered out words to check that Dan was sure, Dan reached into his nightstand and pulled out some lube. Nate smiled and kissed him. "OK," Nate agreed, smiling wider than he ever had with his girlfriend. Nate began to rub the cold lube over his dripping cock. The cold sensation would have really turned him on, if he wasn't already as hard as humanly possible. Dan was under Nate on his back. Dan's legs were spread, and he was working two lubricated fingers into his tight, virgin ass. He bit his lower lip while his toes curled, all the while never breaking eye contact with Nate. OK, Nate was now harder than humanly possible.
Nate propped himself up on his hands , his waist between Dan's widespread legs. Dan lifted his legs, and Nate positioned them on his shoulders. The boys smiled at each other, and Nate leaned forward with on hand guiding his cock. He felt Dan's snug opening, and he slowly pushed forward. Dan cried out at the invasion. It was unlike anything he had ever felt before; Dan felt like he was being ripped in two, but at the same time, it was the most incredible thing that he had ever felt. His entire body felt sensitive and vulnerable and tingly and on fire. Nate pushed further into Dan, and the pain and the seansation both increased. Dan grunted as Nate pushed his long dick further in his hole. Breaking Dan's cherry felt amazing on Nate's cock; Dan's ass was so tight and warm. As Nate slowly leaned into his ass, Dan felt himself relax, and allow himself to be taken. It still hurt, but it was the most incredible feeling he'd ever felt. Plus, Nate looked like an angel fucking him.
Dan's knees were bent over Nate's shoulders, and Nate was buried deep in Dan. The boys could feel their hot breath on each other's faces. Dan looked up with his big, brown eyes at Nate and nodded. Nate leaned in and kissed him, pushing his dick in even further. Then he pulled back, pulling his dick almost all the way out of Dan. Then he pushed his way back in. Dan gasped and felt like he was going to split in half, but if it felt like this, he was ok with that. Nate's tongue was thrusting into Dan's mouth just as his cock was invading his ass. Dan, who always needed to have the last word and always needed to be in control, allowed himself to be taken. And loved it.
Dan ran his hands all over Nate's body: his strong back, his bulging biceps, and hard chest. Soon Dan's hands found their way to his own dick, and he began to stroke it. Nate was steadily pumping in and out of Dan now, and Dan jerked off to the same rhythm. Nate loved watching Dan below him, giving in to him. It was way more power than he ever got from control freaks like Blair and Chuck, and he loved it. Feeling Dan shudder with every thrust and watching him beat his own dick to try and keep up with Nate was so sexy.
Dan loved being taken. With his legs bent over Nate's shoulders, his hole was vulnerable to Nate's cock, and Dan loved that Nate took full advantage of it, fucking him with deep, long thrusts. His asshole clenched Nate's member, working its whole length as it shoved in and out. Nate's balls slapped up against Dan's ass as he buried the whole of his dick.
It was too much for Dan. He was moaning and vulnerable, and he made intense eye contact with Nate as he worked his own tool. He pulled Nate's head down and the boys kissed passionately, as Nate's tongues invaded Dan's mouth just like Nate's dick took his ass. As Nate pumped into Dan, Dan jerked a few more strokes on his cock and felt his orgasm building. Then Dan's cock fired off shot after shot of hot cum. The first shots hit the boys' chins as they continued kissing, and the next few blasts went everywhere: their necks, chest, stomachs, and the bed.
The hot cum firing all over his hot young body sent Nate over the edge. He pulled almost completely out of Dan and then jammed his dick deep inside his new lover's broken cherry hole. Nate sprayed streams of his hot boy juice deep in Dan, spurting all over the walls within Dan. His scorching cum filled Dan up, and Nate collapsed on Dan, leaving his dick buried in him, allowing the rest of his cum to flow into Dan.
The spent boys kissed and smiled at each other. Then they heard the front door open. Years of fooling around with Chuck and Blair had prepared Nate for this, as he jumped off the bed and pulled his clothes on in one motion. He turned to face Dan and smiled, saying "Remember to thank Jenny for me," and then Nate was opening the window and fleeing down the fire escape.
Dan took a few minutes to recover. Finally, he got off his bed and pulled on his sweatpants. He went out into the living room where Jenny was putting away groceries. Dan told her that Nate had stopped by to thank her or whatever. Jenny was mortified, "The coolest guy in school comes over to see me and instead he sees you laying around in your sweatpants. He must think we're such freaks!"
Dan smiled, as he usually did when his sister freaked out about the Upper East Siders. Except this time, there was a different reason for the smile. Dan was pretty sure that Nate didn't mind him in his sweatpants, although he had been in a hurry to get him out of them.
*** That's it for now guys. Let me know what you think! xoxogossipguy@hotmail.com