Authors Note

Explicit, graphic male/male sex. Spanking and punishment. Continue at your own peril.

Chuck was bored. He was always bored lately. There were only so many times you could take the company jet down to St. Barts for the weekend before it got old, only so many times you could bathe with three hookers in a bath of champagne, only so many times you could buy out and sell companies at a profit and still get satisfaction out of it.

What he really wanted was something new. He had the perfect idea of how to get it.

He couldn't exactly say he had never had sex with men before, he reflected as the limo passed over the Brooklyn Bridge and into the ungainly borough, but he had never had sex with Dan. Plenty of guys threw themselves at him, and who was he to turn them down? The thing about Dan was that he was so fucking snooty and pretentious that Chuck would have fun with him.

It had all came to him when a drunk Dan admitted to Chuck that, as a writer, he should get as many experiences as possible. Chuck had kissed him then and there, and that had been a week ago. The guy was probably in an emotional turmoil right now, wondering if Chuck loved him. But Chuck didn't love any one. Not since Blair.

He had closed off his heart and returned to his past, to when he would fuck whores with such a relentless pace they would be sore for weeks. He was determined to give Dan the same treatment. The guy looked down his nose at everyone, but soon enough Chuck would be looking down at Dan as he worshipped the ground Chuck walked on, he would make sure of it.

Being Chuck Bass meant that he could do whatever the hell he liked, so he had arranged for a very prestigious magazine to interview Rufus Humphrey, the irritating father who Chuck sometimes mused as to if he swung both ways. He could probably persuade the guy, but the son was the target tonight. Little J, who was back from London for the summer (confined to Brooklyn due to Blair's ban) had been invited to Vera Wang's private showing on the Upper East Side, which Chuck had arranged with ease. Vera was an old friend from his Blair days.

Arthur was instructed to head home for the night. Chuck knew he'd need more than a few hours with Dan, he'd just order a car to get home in.

Dan's stubbled face flinched when he threw open the doors of the loft in just a baggy shirt and some baggy plaid boxers, a mug of coffee in one hand and a pen in the other, his hair a tangled mess, his eyes bloodshot from lack of sleep.

"Chuck," He mumbled, his eyes drinking in the sight of the suited man in front of him, looking perfectly put together as usual. "What do you want?"

"Why, you of course," Chuck grinned, stepping into the loft without being invited, "why else would I travel all the way to this god-forsaken borough?"

"I'm kind of busy," Dan stuttered, running over to the coffee table and slamming the open laptop shut.

"Busy with what?" Chuck drawled, removing his shoes and jacket. Dan couldn't help but stare at the way his body was accentuated in the tight fitting shirt, the way his crotch stuck out of the tight pants. He could feel his dick growing and knew Chuck would be able to see; boxers were hardly a good cover.

He quickly excused himself, running to his bedroom to put on some pants. Chuck flipped open the laptop absently and began reading the document Dan had been working on, a series of scribbles written on the mess of coffee stained mugs around the computer.

"Don't tell me, this is about me, isn't it?" Chuck grinned, reading the short story about the young man who received an unexpected kiss from a billionaire bachelor.

"Maybe," Dan conceded, hanging his head.

"Well, you said you wanted new experiences, we're starting right now." Dan looked up, his brow furrowed.

"What are you doing?!" He didn't move, he just watched in shock as Chuck started stripping himself, throwing his shirt and tie onto the couch, slipping out of his pants, removing his socks, and finally pulling down his silk underwear to reveal the dick Dan had been thinking about all week.

It was all wrong. This wasn't how Dan was supposed to see Chuck naked for the first time, he was supposed to kiss him in the rain and make passionate love to him in the candlelight. Not be presented with the beautiful, naked man in front of him with no build up.

"It's not going to suck itself." Chuck pointed to his growing cock, fists resting on his hips and his crotch jutting out.

"Chuck – no..." Dan felt shame rumble around with the coffee in his belly. He wanted to. He wanted to attempt to take what could only be described as that huge piece. He wasn't supposed to want this.

"Yes, Humphrey. You dink. Get over here, or do I have to force you?" Chuck had a smirk playing on his lips, putting one leg up on the coffee table so he was even more exposed for Humphrey, who was clearly turned on judging by the bulge in his grey sweatpants.

"I've never – you know -" Dan was stuttering, feeling the blush covering his cheeks.

"Sucked a cock?" Chuck let out a bark of laughter, enjoying the way the profanity made Dan squirm. "I'm an excellent teacher." Dan knew he shouldn't, but he found himself crossing the room till he was face to face with Chuck. He went in for a kiss.

The expectant face, eyes closed and lips puckered, was pushed away none to gently, a smirk on Chuck's lips, "Ah-ah-ah, no kissing, you've already had that experience. Time for something new." His fingers were soon twined in Dan's hair as he guided his head down, taking hold of his own semi-hard cock and pushing it onto Dan's closed lips.

"I don't, I can't" Dan muttered, trying to angle his head away. Chuck wouldn't let him. He had a firm grip on his shaggy brown curls, and he was determined to get off.

"You will." He practically forced Dan's jaw open, shoving his meat inside, giving Dan no other option but to try. It tasted strange, felt strange. All fleshy and soft and just weird. It was a good weird, especially when it started to grow under Dan's tongue.

Being Humphrey, he had done some research into gay sex when Chuck had kissed him last week, but no amount of literature prepared him for actually giving a blow job. It was nothing like he had read, no one told him that you could hardly breath, that your jaw ached from stretching to its limit, that when the man who you were sucking forced his dick right down your throat you thought you might choke.

"I'm getting bored, Humphrey." Chuck checked his rolex to illustrate his point. "Stop looking up, it's creepy." He continued, the disdain in his voice bringing a tear to Dan's eye. His dick was hard now, he could admit Dan was a decent sucker, but, being who he was, he'd had better.

He took things into his own hands, guiding Dan's head back and forth, taking the cock out and slapping it across his face a few times.

"You like it, huh?" Chuck grinned, his voice low and throaty. He loved the sound of his steely meat slapping off Dan's cheek, the feeling of the stubble on the sensitive flesh turning him on even more.

"Yes," Dan gulped. He hated how talking dirty made him feel. Hated it because it felt so good, felt so freeing compared to his usual 'romantic' self. He loved this, and he hated himself for it.

"Stand up and get naked." Chuck pulled his dick from the warm, wet prison with a pop, pulling Dan roughly to his feet. He obliged Chuck's every request. Dan was putty in his experienced hands.

"N – Now what?" Dan gulped, when he was finally naked. His dick was embarrassingly rock hard, but he didn't cover it. He knew Chuck wouldn't like it.

"Now you come here." Dan didn't have to move, Chuck just dragged him along, sitting down on the sofa and spreading Dan's naked body over his knee. Chuck was glad Dan had returned to his tortured, skinny old self, that brief period when he had put on muscle had turned him off completely. This was how he liked his men, thin and shy.

Thwap.

"Ah! What the -" Dan cried out, trying to jump up but finding he was completely trapped on Chuck's knee, one of his strong arms holding Dan's waist, pushing him into his hard on, while the other spanked him.

Thwap.

Chuck loved the red mark that came up to meet his hand, marring the smooth, white skin. Dan was in heaven and hell at the same time, he didn't want to like it but he did.

"You want it again, don't you." Dan knew from anyone else it would have been a question, but from Chuck it was just a fact. There was no question there, he could tell by the look of bliss that crossed Dan's turned head for just a second after each slap that he loved it.

"Y – Yes." Dan bit his lip and tried not to cry out as Chuck's palm met his ass once more, leaving a strange feeling in his belly as he cock grew harder ad harder, if that was even possible.

"Don't be shy, no one's home to hear you." Chuck grinned, slapping the skin again. He was panting as he watched Dan, heard the barely contained moans low down in his throat that were threatening to spill out. He wanted them to spill out, wanted to hear how much Dan liked it.

"Oh, shit." Dan yelled, finally letting his first real sex talk escape. Chuck kept on slapping, a grin on his face as his hand came down in a slow, steady rhythm, running his wide palm over that sweet red spot after he smacked him, feeling the tender, pert flesh beneath his hand.

Dan's ass was on fire by this point, but every slap was somehow better than the last, even though each one hurt more than the last. He had never in a million years thought he would be laid over a naked Chuck Bass, his meaty cock grinding into Dan's stomach as his own cock grazed Chuck's thigh, having his ass spanked in the middle of his living room. He loved it.

"Stop, please." Dan begged. Not because it hurt, because he needed desperately to cum.

"Suck." Chuck said as he released Dan and pushed him down between his legs, his cock was twitching, his body a little sweaty, he needed to cum and he needed to do it now. He had never expected Humphrey to be such a willing partner, to love being spanked. It was turning him on like crazy.

It didn't matter that Humphrey couldn't suck cock to save his life, he just used his mouth as a hole, guiding his head up and down, watching the amazing sight of Dan bobbing up and down between his wide spread thighs.

Dan didn't know what was happening, all he could do was try not to gag as he was face-fucked, Chuck's hands slapping his hand away from his own cock when he tried to jerk himself.

Then he came.

Dan's mouth was full of the strangest liquid he had ever tasted, it was strange and salty and sweet and nice and revolting at the same time. It was hot, wet, and he could feel it coating the inside of his mouth and pouring down his throat. He tried to get off, but Chuck was holding him down, a grin on his face as he rode the orgasm, urging Dan to swallow it all. There was no other choice, he had to let it go down his throat. It stung, it was the only way he could think of describing it. It was tangy and it made him want to throw up and drink more at the same time.

"You're such a slut, Humphrey." Chuck grinned as he finally released Dan, who gulped in the air as if he hadn't took a breath in years, making choking sounds as he tried to get rid of the cum that was stuck to the back of his tongue.

Dan moved away, reaching for his sweatpants, "I hope you're not getting dressed. We're only just getting started." Dan gulped at Chuck's words, a pit of excitement and trepidation forming in his stomach. Chuck just pulled Dan back and bent him over his knee once more.