Season 5, Episode 3 - The Kids Stay Out of the Picture

After getting yelled at by Will and Grace, Jack and Karen left and went across the hall to his apartment. Karen pouted as she sat on the blue couch, Jack following behind her.

Noticing the expression on her face, Jack frowned. "What's the matter, Kare?"

Karen huffed and crossed her arms over her chest petulantly. "I didn't get to finish showing you how Leo kissed," she grumbled, her eyebrows furrowed.

"Aww," Jack deflated and a pout formed on his lips as well, disappointed. "Wait!" He perked up and laid a hand on Karen's arm, drawing her attention to him. "Just show me again! He's already good - how much better could he be?"

"Oh honey," Karen fanned herself again.

"Well show me, show me!" He was bouncing in his seat in excitement.

Karen didn't dawdle - she grabbed his face in her hands and brought her lips to his, pouring everything into the kiss. It was hard, deep, passionate, and exhilarating. She tilted her head and brushed her tongue over his lips teasingly and after a good, full minute, she pulled away, their mouths parting with a smack.

When she opened her eyes she saw the same dazed look she had on her own face a few days ago when Grace kissed her reflected on Jack's features. Jack kept his gaze on her lips as they lightly panted together, Karen's hands still cradling his face. Like magnets, they collided again. Her tongue immediately slid into his mouth to seek his out. Jack wrapped his arms around her, pulling her on to him so she was straddling him on the couch. Karen's arms went around his neck and she grinded down into his lap, surprised to feel a slight buldge between her legs. Jack grunted and grabbed her ass in his hands pulling her impossibly closer. He bucked his hips up and she whimpered against his mouth, tugging the hair at the back his neck. Karen moved against him again, rubbing herself through his jeans and her slacks. She didn't know what was happening or what came over them, but she never had such a carnal desire to fuck her best friend before now. She moaned when Jack used his hands on her ass to guide her as he raised up, increasing the friction between their bodies.

Karen came quick, but hard, her thighs quaking from the sensation. She gasped into Jack's mouth, holding his chin in her hand as they breathed into each other's mouths, hazel eyes boring into light blue. She saw the desperation on his face and began to jerk her hips back and forth again, her pelvis snapping into his. She shoved her tongue back in his mouth as he finally came, his cock twitching in his tight jeans and his fingers digging into her ass cheeks, a guttural moan of pleasure vibrating against their lips.

They stared at each other, the realization of what just transpired between them hitting like a ton of bricks. Karen slid off from his lap and on to the couch beside him, her eyes glancing down at the dark spot on his jeans. Jack grabbed a nearby pillow and placed it over his lap, but it was a moot point to which Karen couldn't help but let out a giggle. He stared at her for a moment before erupting into laughter himself.

"Sorry," Karen said after they calmed.

"For what?" Jack asked, tilting his head to the side like a confused puppy.

Karen smiled and reached over to wipe a smear of lipstick off his bottom lip, cupping his jaw in her hand. "For what just happened... I didn't mean to take advantage of you-"

"You didn't take advantage of me," he cut her off with a shake of his head and grabbed her hand from his face, holding it in his lap. "I'm sure Leo is a great kisser." He leaned over, kissing her cheek, and whispered in her ear. "But no one compares to you."

Karen shivered as his lips brushed her ear and as he stood from the couch she stared up at him quizzically, but decided not to question him. Jack walked to the bedroom and looked over his shoulder as he spoke. "I'm gonna change my uhhh well my pants and underwear," he grimaced and Karen blushed. "You wanna have a sleepover?"

Karen cleared her throat and stood from the couch, grabbing her purse that she left there earlier. "No, honey," she replied with a timid smile. "I think I'll head home-"

They heard the door across the hall slam, the sound almost making the walls rattle and they stared at each other in surprise. Jack quickly changed his clothes while Karen ran out into the hall to find Grace smashing the elevator button, tears streaming down her face.

"Gracie?" she asked quietly as she walked up to the distraught woman. "What happened?"

"I don't want to talk about it," Grace sobbed, wiping tears away from her face. The elevator dinged open and the red head rushed inside just as Jack exited his apartment with a fresh pair of pants on and a confused expression on his face.

"Is everything okay?" he asked, glancing at 9C before turning his attention to Grace inside the elevator.

Karen opened her mouth to respond when the elevator dinged again and the doors started to close. "I- wait, Grace!"

But the doors slid shut in front of her face and Karen sighed, looking over at Jack with worry.

"What the hell is going on?"