Summary: Dan and Serena have a secret affair while she is with Aaron. Will they take their relationship public or will they let the fear of failure overwhelm them?

Pairings: Serena and Aaron, Dan and Serena, Dan and Random

Author's Note: I do not like Aaron. If you are looking for a positive depiction of him look elsewhere. I am a DS shipper through and through. Yes, I know I have like a gazillion in complete fics, but don't worry Adventures of Lonely Boy will not be ignore nor will be Chances. I am sorry it's taken so long to reupload this fic. I originally wrote this during s2. I apologize if it sucks

Chapter 1: It happened one night

Dan made his way home and ran into his bedroom letting the loneliness and despair engulf him. He felt like his dreams were crumbling at his feet. What was the point of working this hard to achieve nothing? He hated that all those days and nights of studying and making sure that everything was impeccable only for it to fall apart at the last minute. It just wasn't fair. The kids that he went to school with didn't have to work for a thing. Everything was handed to him on a silver platter. All they had to do was snap their fingers and everything they ever wanted was laid before them—the best schools, the best clothes, the best homes. Dan was stuck crawling and scratching to just make sure he had a chance to be successful. He wanted to be a successful writer and the best way to get there was Yale. Now, he was being told that it was his writing that was holding him back from achieving the one thing he wanted to achieve. He was still wallowing in self-pity when Serena stuck through her shiny blond head through his bedroom door.

"hey, how are you holding up?"

"Um, not so good. My life is basically over,"Dan said with a shrug.

"That's a tad melodramatic don't you think?"she replied.

"Nope. It's the truth. No recommendation equals no Yale. No Yale equals failure," he said as he hung his head from the edge of the bed. He smiled up at her and said, "what are you doing here anyway?"

"I came to cheer you up,"she said as she presented a bottle of red wine. "I thought we could drown your sorrows in a bottle of this,"she said with a smile.

Dan flipped over and looked at her wearily, "Ugh, I don't know if getting drunk is the answer Serena?"

"Loosen up Dan. One night of drunkness is not gonna kill you and it will make you feel better for now,"she said as she waved the bottle in front of his face. Dan grabbed it and went to find a few cups. He came back with two coffee mugs and the bottle. He opened the bottle and poured them each a bit. He handed Serena a mug of wine and said, "To epic failure and wallowing."

Serena rolled her eyes and said, "to hope."

She watched him as he chugged the wine and poured himself some more. Dan wasn't much of a drinker, but when he chose to imbibe he could get out of control. She had never seen him this depressed and it concerned her.

"So, how's the caterpillar man?"Dan asked. He was already getting a bit woozy and the very idea of Serena being with Aaron made him even woozier.

"The caterpillar man? He's fine. A little preoccupied,"she said nonchalantly.

"What does that mean? Preoccupied?"Dan asked as he took another gulp of wine.

"It means that he has a small harem at his beckon call,"she said as she finished off her wine poured herself some more.

"A harem? Oh you mean he's fucking around on you?"Dan said. He knew he should have been a bit nicer, but everything about that guy bugged him. He was just creepy and he wasn't good enough for Serena as far as he was concerned.

"We're not exactly exclusive,"She said.

"Why the hell not? Look at you. Who wouldn't want to spend all their time with you? He's crazy, "Dan said matter-of-factly.

Serena didn't know whether to be annoyed with him or to be flattered. He was in fact her ex-boyfriend; the same ex-boyfriend who had dumped her not once but twice. She looked at him took a swig straight from the bottle and handed it to him. Serena shrugged off her shoes and joined him on the bed. She was feeling all warm on the inside and wanted to stretch out because the floor was a bit uncomfortable. She placed her bare feet on his lap and closed her eyes as he gently massaged her feet. Dan used to do this all the time when they were going out and she missed their easy intimacy. It probably wasn't the best idea, but she didn't care. "mm that feels good. Thanks Dan."

"No problem. You really should stop wearing those gigantic heels. You don't need them and they only hurt your feet. We wouldn't want your pretty little feet to be all disfigured now."

"So now you have a thing for my feet?"

Dan slid his hands up her leg and said, "not just your feet."

He was drunk and he knew this was a bad idea, but a part of him didn't care. One of the reasons he didn't drink was because it made him horny. Serena froze in place not knowing what to do or say. She could feel his hand moving up her leg and it felt great, but it also made her apprehensive. Her defences were down and if he kept going she knew she wouldn't be able to stop him. His mere touch set her on fire. There was just something that always ignited between them even when they were trying to be nothing more than friends

"Maybe the wine was a bad idea," she muttered to herself.

Dan had moved so that he was lying on top of her. He grazed her cheek with his thumb and dipped his head and pressed his lips against hers. The touch was feather light yet it sent shivers down her spine. Serena sighed and parted her lips which he took as a silent invitation to continue his exploration. He traced her lips with his tongue. "I missed this," he muttered as he kissed her again. He gently sucked on her lower lip which elicited a small moan from Serena. Dan deepened the kiss and soon his tongue was in her mouth. She could no longer fight her reaction so she kissed him back with everything she had. Soon their tongues were duelling for supremacy. Dan pulled the straps of her black ball gown down off her arms which exposed her breasts to him fully. He took them in his hands and sucked on one and then the other.

"You have the most fabulous breasts ever. You are like a goddess. So, fucking beautiful," he muttered as he continued sucking and nipping on her breasts. Serena grabbed a fist full of his first and tugged as she moaned.

"The hair Serena. Loosen the grip babe,"he pleaded.

"Sorry,"she said sheepishly.

"Its okay," he said before returning his attention on her body. He slipped the rest of the dress from her body. He didn't care that they weren't together. He didn't care that she was sort of dating Aaron. All he wanted was to bury himself deep inside of her.

Dan slid the panties off and pushed her legs apart. He loved to hear her moan his name as she came and he was determined to make her come over and over again tonight. Dan wanted to brand himself so that every time he touched her she was forced to think of him. He knew Serena had been with a lot of guys, but he was determined to be the one that she couldn't forget. He kissed her inner thigh and slid his tongue along her core making her contract by the sudden contact. Dan kept licking her and each twitch of her hips only egged him. He remembered the first time he had tasted her there. It was an incredible feeling knowing that he could drive her wild so easily. He stilled his tongue for a moment and blew on her core which caused Serena to buck her hips in frustration.

"Stop torturing me down,"she said.

He looked up at her. She was so beautiful. Her blond hair was askew and it only made her hotter to him. He could feel the strain of his hard-on against his pants, but he was determined to make her come while he watched first.

He stuck one finger than another inside of her. "How's that baby?"

Serena didn't say anything she simply moaned and he began to finger fuck her until she was gasping for breath. "Say it?"

"What,"she said breathlessly.

"My name. Say it."

"Huh Dan?"

"Not like that,"he pleaded.

When she wouldn't comply he abruptly removed his fingers. She looked at him with frustration "Why'd you do that? Put them back now."

"No!"

"Please"

Instead dan decided he couldn't wait any longer so he got up stripped off all of his clothes, slipped on a condom and looked her straight in the eye, "Say it."

"Dan please."

"Please what?"he demanded.

"Fuck me."

He grinned and said, "okay."

Dan positioned himself so that he wouldn't be off balance before entering her. It felt like heaven to be in her again. Dan and Serena met each other thrust for thrust. They were like two people who had been starving finally be giving a meal. They had both been craving each other so badly that they had held each other back in the name of friendship. Their coupling was fuelled by unresolved sexual tension and alcohol a deadly combination at the best of times. Serena held him tightly she never wanted this night to end. She wanted to hold on to him to remember this. To etch this moment in her memory. They both collapsed and fell asleep in each others arms. They would wake up several times that night and do it again. The other times were less frantic less frenzied and more sensual. By the time the sunlight streamed through the window, Serena was exhausted and sore. She slipped on her dress and her coat. She kissed him softly on the cheek before leaving the loft as quietly.

Rufus walked in on his son who was out cold. He was angry to say the least. Apparently Dan had brought a girl over. He didn't know what was going on with his son, but he didn't like it. Rufus threw a pillow at Dan and said, "What the hell do you think you are doing, Daniel Theodore Humphrey?"

"Ugh, I was sleeping Dad."

"Who was she?"

"What are you talking about Dad?"

"Dan you know the rules. No sex in this house. Look at you. You are a mess. There are condoms strewn all over the floor as well as a bottle of wine that you and your companion managed to down in one night. This is not how I raised you!"

"Gah, Dad can we not have this conversation right now,"Dan said as he sunk under the covers.