Title: The Pundit and the Pauper
Author: darkfaery1
Chapter: 6/6
Genre: TDS/TCR/Strangers With Candy Crossover
Pairings: Jon/Stephen, Chuck/Geoffrey
Rating: NC-17
Content: Slash sex (some of it kinky), language, character!Stephen, comedic angst.
Chapter summary: Our two happy couples express their true feelings for each other.
Word count: 2815
Author's Note: Thanks to everyone who stuck with this story to the not-so-bitter end. A very special thanks to my awesome beta insanekht for all her help. Disclaimer: This is a work of fiction and is not intended to portray the life or defame the character of any actual person. Any similarity between the fictional version of the person portrayed here and the actual person is purely coincidental. No money is being made from this work of fiction. It is not intended to infringe upon any copyrighted material. Any mention of 'The Daily Show', 'The Colbert Report', 'Strangers With Candy', or any other copyrighted material is reasonably protected by the Fair Use Rule of the United States Copyright Act of 1976.

Crossposted to tds_rps

Chapter 1, Chapter 2, Chapter 3, Chapter 4, Chapter 5



"Geoffrey," said Chuck, who was on his knees, handcuffed to his headboard. "Is this absolutely necessary?" Chuck yelped as the riding crop came down on his bare backside.

"I'm afraid it is, Chuck," replied Geoffrey, tugging lightly on the leash attached to Chuck's black leather collar. "You've been a very bad boy and need to be punished."

One corner of Chuck's mouth curled in a grin. As much as he loved being on top, Geoffrey could be so darned dominant when Chuck let him. And a dom Geoffrey was the sexiest thing ever, not that Chuck would ever admit it and spoil the fun.

Geoffrey walked slowly towards the head of the bed to give Chuck a chance to feast his eyes on his lover. Geoffrey was naked from the waist up, showing off his finely sculpted chest and stomach. He wore tight leather pants that left nothing to the imagination.

Chuck struggled against the padded handcuffs, anxious to feel those rippling muscles, among other things. How could he have almost given up this Adonis for a middle-aged, slightly lumpy Jon Stewart? "Please, Geoffrey, let me do something before I explode."

Geoffrey smiled and produced the key. He unlocked the cuffs, but didn't remove them. He ordered Chuck to lie on his back, then reattached the cuffs to the headboard. He then climbed on the bed, straddling Chuck's middle. Geoffrey ran one hand over his own chest teasingly, then covered his leather-clad cock with the other. "You want this?"

"Yes, please," Chuck said with what he hoped was a sexy whisper.

Geoffrey licked his pouty lips. "Do you think you deserve it?"

"No," admitted Chuck, "but give it to me anyway, pleeaase, Geoffrey."

Geoffrey popped the buttons on his fly slowly, grinding his hips filthily, finally revealing his hardening cock, unencumbered by underwear. Chuck opened his mouth and stuck out his tongue, begging for a taste. Geoffrey scooted closer until his cock hovered over Chuck's mouth. He put his hand on the back of Chuck's head for support as he began thrusting the head of his cock between Chuck's willing lips. Geoffrey gingerly pushed more and more of his cock into Chuck's mouth, being careful not to overdo it and accidentally touch Chuck's hypersensitive uvula. Chuck hummed his enjoyment of this kinky treat, looking up at Geoffrey with dark, smoldering eyes.

When Geoffrey sensed he was getting close, he withdrew reluctantly. Like a cat, Geoffrey arched his back and lowered himself on top of Chuck, nuzzling his neck, and gently nipping at Chuck's earlobe.

Chuck dug his heels into the bed and lifted his hips to increase the contact, but Geoffrey rose up with him, denying Chuck the full pressure of his body. Geoffrey inched backward, down Chuck's torso, blowing lightly on each nipple in turn, merely grazing his tongue through the trail of hair down Chuck's chest.

Chuck whimpered and whined for more as Geoffrey placed bites on Chuck's hip, then ran his tongue along his pelvic bone, stopping short of the base of Chuck's bobbing erection. Geoffrey smiled up at his lover devilishly, enjoying every second of Chuck's torture. Chuck bit his bottom lip to stop himself from begging and possibly drawing this out even longer.

Geoffrey glanced at the clock. It was eight-thirty. "What time is Clair coming home?"

"Who?"

"Your wife."

"Oh," said Chuck unenthusiastically. "About nine. Can we move this along, Geoffrey? My wrists are starting to go numb."

Not the most romantic thing he could have said, but it would do. Geoffrey produced a pina-colada flavored condom and tore open the wrapper with his teeth.

"Aren't you going to at least blow me first?" Chuck asked in irritation.

Geoffrey gazed at Chuck coyly. "I had something better in mind, but if you'd rather--"

"No, no," Chuck said quickly. "You're in charge tonight, my master--"

Geoffrey giggled like a little girl at the unfamiliar form of address.

"Do with me what you will," Chuck added for extra drama. "But hurry, Clair coming home soon and it's banana daiquiri night at her book club. If you don't do something about my boner soon--" he shivered. "--she will."

"Okay, where was I?" Geoffrey put the condom on tip of Chuck penis and rolled it down to the base with his pillowy lips.

"Oh, yeah," Chuck moaned, pleasantly surprised by Geoffrey choice. Chuck didn't like to complain, but his ass was still a bit sore from that thumping Colbert gave him the other night.

Geoffrey squirted some lube over the tip and worked it slowly down the shaft, then, in strip-tease fashion, removed his leather pants and prepared himself to receive Chuck. Geoffrey poised himself above Chuck's hips and carefully eased himself unto his cock.

Chuck's eyes rolled back in his head as Geoffrey started moving up slowly and then pushed down hard and fast until Chuck was buried inside him up to his balls. Geoffrey continued this rhythm, quickly picking up the pace; he grabbed his own cock and started stroking it to the same rhythm.

Chuck lifted his hips, meeting every one of Geoffrey's downward thrusts. They locked eyes, sensing they were getting close. With a high-pitched cry, Geoffrey called out Chuck's name as orgasm wracked his taut body, his come covering Chuck's chest and stomach. The sight sent Chuck over the edge. With one final upward thrust, Chuck erupted inside of Geoffrey. Geoffrey collapsed on top of his lover and gave Chuck a violent, sticky kiss.

They both ached for sleep, but Geoffrey glanced at the clock again and fumbled for the key to release Chuck. Geoffrey gently kissed the red marks on Chuck's wrists as an apology. Chuck frantically gathered up all the kinky accoutrement and stuffed them into Geoffrey's paisley messenger bag, then cleaned them both up with a damp towel.

"I love you, Chuck," Geoffrey said as Chuck threw the bag out the window onto the roof next to the trellis.

"I love you, too, Geoffrey," Chuck replied, pushing Geoffrey out after his bag. "Now, get the hell out of here before Clair sees you." As soon as Geoffrey cleared the ledge, Chuck closed and locked the window. Then he quickly put on his pajamas and jumped into bed, doing his best to feign sleep.

A few minutes later, Clair burst in their bedroom and flipped on the lights. "We're having sex tonight, Chuck," Clair announced in a slightly slurred voice, throwing a book at his back.

Chuck rolled over and sighed. "Let's get on with it then." He turned away as Clair clumsily stripped to her bra and panties, then crawled in bed next to her husband. Chuck then did what any god-fearing, married man faced with his monthly obligation would do…

He closed his eyes and thought of Geoffrey.

***

Jon decided to wait for Stephen in the empty basement outside the Lair rather than in the studio, knowing Tad would tell Stephen he was waiting. Jon didn’t want Stephen to feel like he had to prove something by having sex with Jon. This way, if Stephen wanted to skip out, he could do so without having to face him.

Jon checked his watch. The show ended at least fifteen minutes ago, even if it had gone long. He'd be pathetic and wait an hour before going home and probably crying himself to sleep. At least he had the kiss. Jon smiled. The sensation of Stephen's tongue shoved down his throat would stay with him for the rest of his life.

Fifty-nine minutes passed and so did Jon's hope for a deeper relationship with Stephen. With a sigh, he walked to the elevator and pressed the 'up' button.

A few moments later, it opened with Stephen inside. He looked a little sheepish and more than a little terrified. He quickly covered it with a plastic smile. "Hi, Jon, fancy meeting you--"

"How long have you been riding up and down the elevator?" Jon asked.

Stephen checked his Rolex. "Um, fifty-six minutes."

"Are you coming out?"

The unintentional double entendre was not lost on either of them. Stephen continued to hold the elevator doors open, his internal struggle clearly written on his handsome face. Jon stepped inside the elevator and pushed the 'Lobby' button.

Somewhere between the Colbert bunker and Basement 4, Stephen pulled the emergency stop button causing the elevator to come to a stuttering halt. "Why are you wearing a suit?" Jon couldn't help but notice the disappointment in Stephen's voice.

"It's Armani, the best suit I have," Jon told him. "I thought you liked it."

Stephen shrugged. "I was kind of hoping for a grey sweatshirt and jeans, snug, but not too tight."

"But you always go on about how unkempt I look when I dress like that."

"No one works unkempt like you, Jon," Stephen replied with a shy grin.

Jon gratefully removed his tie and undid the top two buttons on his shirt. "Better?"

Stephen furrowed his brow in consideration. In two deft moves, he ripped Jon's shirt all the way open, sending buttons flying against the elevator walls, then pulled off his coat and shirt. Stephen placed his hands on Jon's chest and pushed him gently against the wall. Jon slipped his hands around Stephen's waist and pulled him close.

Stephen mussed Jon's hair playfully, then he took Jon's face in his hands and place a slow, sensual kiss on his lips, so unlike the tonsillectomy from last night. As he explored Jon's inviting mouth with his tongue, Stephen worked his hands underneath Jon's tee shirt, running his hands over his bare skin. Jon moaned appreciatively at Stephen's touch.

Suddenly, Jon's eyes popped open and he reluctantly pushed Stephen away. "There are cameras in all the elevators," Jon said in response to Stephen's questioning look. "Let's get out of here before this ends up on You Tube."

Stephen gave him one of his superior smiles and captured Jon in his arms once again. "Not to worry, Jon. This is my private elevator. I had the camera removed two years ago. What happens in this elevator, stays in this elevator."

Jon laughed. "Really? Well, in that case…" Jon slipped his hand on the back of Stephen's head and pulled him down for another long kiss. He could feel Stephen's arousal against his hip, his own cock straining against his suddenly restrictive clothing. Stephen's hands continued to explore every inch of Jon's skin he could reach. Jon was as anxious as Stephen to feel the bare skin of his lover, but the idea of pleasuring a fully-dressed, perfectly-groomed Stephen was too much to resist.

Jon turned Stephen around, so he had his back against the elevator wall, then eased himself down on his knees and unzipped Stephen's fly. His cock was already rock-hard and throbbed in Jon's hand as he released it from Stephen's red, white and blue boxers. Jon looked up at Stephen with a bashful smile as he began to tease the head of Stephen's cock with his tongue. Stephen held his breath as he watched Jon take him in his mouth, inch by agonizing inch.

Stephen looked down into Jon's blue eyes, then leaned back, resting his hands on the elevator's grab bars. Good thing I didn't have them removed, too, Stephen thought. Jon closed his eyes and pulled Stephen's hips forward, encouraging Stephen to thrust in his mouth.

Jon's lips and tongue surrounding him felt amazing enough, but the sight of Jon submitting to him so completely, would have been enough to make Stephen climax if he wasn't using all his considerable will not to let it end so soon. When it did become almost too much to bear, Stephen lightly pushed Jon back, then helped him to his feet and claimed his lips once more.

"Fuck me, Stephen," Jon murmured against Stephen's mouth.

Stephen withdrew slightly in order to gaze at Jon with uncharacteristic uncertainty. "Uh, now? In the elevator?"

Jon kissed him again, then ran his tongue along Stephen's jawline. "Why not? Nobody's watching."

Stephen suddenly saw in his mind's eye the vision of him fucking Jon into the unyielding wall of the elevator; the two of them grunting wordlessly, coming fast and hard, making stains the cleaning crew wouldn't be able to get out. Those thoughts morphed into the memory of Stephen pounding Chuck into the mattress. "You're a dirty whore, Chuck…" Stephen had said with so much venom. He shook his head. Jon wasn't a whore and Stephen wasn't about to treat him like one. "I don't want to fuck you, Jon…"

Jon's face fell and he looked away.

Stephen took Jon's chin in his hand and turned his head to face him. "I want you to make love to me."

"Oh, Stephen," Jon said with a relieved laugh, "that is so gay."

They returned to the Lair, leaving a trail of discarded clothing leading into the den. It didn't take long for Jon cuddling next to him on the soft sofabed to make Stephen forget his bizarre tryst with Chuck the other night. Jon made him feel safe and very much loved, giving Stephen the courage to let Jon take the lead.

"It won't hurt too much, will it?" Stephen looked up at Jon like a little boy on his first trip to the dentist.

Jon almost offered to give him a lollipop afterward if he was a brave boy. "It kinda hurts a lot at first, but--Stephen, you don't have to do this. You called shotgun, remember?"

"But it does feel good after a while?" Stephen asked, trying to keep the fear out of his voice and failing miserably.

Jon nodded and brushed a stray lock of hair out of Stephen's face. "Like nothing you've ever felt before, I promise."

"Okay, let's do it before I lose my nerve." Stephen threw the covers back and lay spread-eagled on the bed. "My safe word is, 'take that thing out of me now.'"

Jon giggled, placing a few calming kisses on Stephen's damp forehead, and told him to bend his legs toward his chest. Though it would have been easier if Stephen got on his hands and knees, Jon knew instinctively that Stephen would not let him do this if he couldn't look into Jon's eyes throughout for reassurance. At the same time Jon inserted one lubricated finger inside Stephen, he took Stephen's length in his mouth again.

Stephen gasped at the dual sensations, rocking his hips, and lightly tugging on Jon's hair. Another finger, and more pain melting into pleasure. Jon pushed on Stephen's legs and went deeper inside him, finally grazing his fingers against Stephen's prostate. Stephen cried out and thrust himself into Jon's mouth, feeling himself nearing the edge again. "Jon, please," Stephen begged.

Jon sat up and wriggled in between Stephen's legs. He ran his hands over Stephen's trembling form, waiting for Stephen's breathing to slow. "You okay?"

Stephen nodded, meeting Jon's blue gaze with wide, dark eyes. "I trust you, Jon."

"And I love you, Stephen," Jon replied, his voice just above a whisper.

Jon tucked a pillow under Stephen's hips, making certain he was comfortable before putting on a condom and applying more lubricant. When Stephen signaled he was ready with a deep breath and a nod, Jon entered him with a gentle but steady thrust. He had found with other inexperienced lovers that easing himself inside a little at a time didn't make it hurt any less and prolonged the adjustment period. Jon regarded the almost comical look of surprise on Stephen's face. It hurt him, Jon could tell by the tension around Stephen's mouth and eyes.

"Do you want me to pull out?" Jon asked, doubting Stephen could utter his safe 'word' at the moment, even if he wanted to.

With a staccato breath, Stephen shook his head, wrapping his arms and legs tightly around Jon. Jon held him for several moments, kissing him softly on the lips and neck, until Stephen whispered, "I'm okay now."

Jon rocked them both back and forth, slowly moving inside him. Stephen rested his heels against the small of Jon's back, allowing Jon to bury himself deeper until he found Stephen's prostate. They moved as one, Stephen's aching cock rubbing between them. Jon held Stephen's head in his hands, looking deeply into his dark eyes, watching with an ecstatic smile as Stephen's gaze seemed to cloud over as he neared climax. Jon broke eye contact, and buried his head in Stephen's chest as he came with a decidedly unmanly sob. Stephen raised Jon's head and covered his mouth with his own. Stephen continued to rock his hips, rubbing his cock against Jon's stomach, climaxing soon after.

They lay, sticky and sweating for a quarter of an hour before Stephen mumbled something that sounded like, "I love you, Jon."

Jon, reluctant to spoil the mood, didn't ask him to repeat it. With any luck, Stephen would say it again and enunciate next time.

***

The End