This story takes place after "The Dundies" from Jim's POV. I tried to imagine how Jim might have felt the night of the Dundies when Pam got drunk and kissed him. (I do not own any of these characters, they are the creations of the brilliant minds of "The Office" writers.)
Jim couldn't wipe the smile off his face as he watched Angela's car pull out of the parking lot. He came to Chili's that night expecting another lame Dundies ceremony, probably mixed in with a few laughs at Michael's expense. It was totally worth it since Pam was going to be there too, even if she was bringing Roy. But to Jim's surprise it turned out to be a lot more eventful than he'd imagined. For starters, Roy left early allowing Pam to move to his table and joke around with him as per their usual banter. He loved that Pam had a similar sense of humor as him and was able to go back and forth with him all day long. This job would be unbearable without her. And she got really drunk, which was wildly entertaining! Jim decided not to think about how she had kissed him just yet. He was still in shock over it and wanted to put a pin in those thoughts until he was safely at home.
Jim threw his keys on the kitchen table and rustled through his mail. The house was dark and quite. It looked like his roommate, Mark, was still out with his girlfriend. He grabbed a soda from the refrigerator and went upstairs to his bedroom. He put his wallet and cell phone on his desk and walked over to his dresser pulling open the top drawer. He loosened his tie with one hand and pulled it over his head dropping it on the floor next to his TV stand. He unbuttoned his dress shirt and dropped it next to the tie. No use in being tidy, no one was going to see his room tonight, Jim thought. He pulled a cotton t-shirt out of his dresser and put it on. Then he unbuttoned his pants and let them fall to the floor. Jim looked into his mirror and sighed. He remembered what Pam said tonight about getting a "second drink" when the ice melts in your glass and it made him smile. She is so adorable when she drinks. She laughs more and with lowered inhibitions she flirts with him. Jim wondered what that means. Is she just a flirty drunk, or does she secretly have feelings for him that she otherwise holds back? He would normally assume it was the former, except that tonight she had kissed him. Sure, she was excited about her Whitest Sneakers Award and she even hugged Michael… but come on… it had to mean something, didn't it?
Jim pondered this thought as he fell back onto his bed. He stared at the ceiling resting his head in the palm of his hand. His other hand lay across his stomach. It was exhausting for Jim to try and interpret nights like tonight. On one hand he and Pam were work friends. She had a fiance. They only saw each other outside the office at work-related events. And she has never come out and said she had feelings for him. Pam was very careful to never cross that line. On the other hand, he could feel a special bond between them that he knew wasn't just in his head. Sometimes she would give him a look or say something that hinted she might feel towards him. Like when her mother came to visit and Jim heard her ask Pam, "which one's Jim?" Although he didn't look up he could hear the embarrassment in Pam's voice at her mother's question. Jim wondered what Pam had told her mother about him. And of course, there was tonight's kiss. It was only two quick seconds and totally unplanned but it happened.
Jim closed his eyes and tried to relive their kiss. He could still feel her arms around him and the sweet way she smelled. Touching each other was very rare. It was a constant struggle for him to keep a safe distance from her at the office. Once he got carried away during a prank on Dwight and Roy walked in to see him leaning on Pam's chair holding her hand. Roy's reaction to that incident haunts him, reminding him just how engaged she really was. Regardless, Jim couldn't help but think about being with Pam. He wondered what question Pam wanted to ask him right before she got into Angela's car. She was about to say something until she realized they were being filmed. Was she going to ask him about the kiss? Jim knew that not knowing the answer to that question was going to drive him crazy. He wondered if that had been his opportunity to tell her how he felt. No, Jim decided. If he ever musters the courage he's not going to do it after they'd been drinking. Jim scratched his stomach under his shirt and suddenly realized he'd become aroused thinking about Pam. Not an unusual occurrence, but one that made him feel guilty. Dirty really, and not in the good way. Tonight he couldn't fight it off. Too many amazing moments had been shared between them tonight. Hopefully she'll remember them in the morning, Jim thought.
His hand slowly made its way to his waistband. He slid his fingertips underneath his blue flannel boxers and reached for his erection. It was long and hard. He closed his eyes again and circled the tip of his penis with his thumb. He massaged it gently, imagining how it would feel to have Pam touching him. He thought about how pretty she looked and how bright her face got when she smiled. He wrapped his fingers around the shaft and started working it up and down, slowly at first and then harder. Pam had laughed a lot tonight. He loved to make her laugh. They'd had a good time together. His heart started beating faster and faster. He continued stroking himself as he thought about the kiss. She had grabbed him, flung her arms around his neck, and kissed him on the mouth. She tasted like a variety of mixed drinks and her lips were soft and wet. It completely caught him off guard and took all the strength he had not to kiss her back. He felt blood rushing through his groin as he masturbated, faster and harder. His breathing became more labored and he felt his skin get hot. He was getting close. He thought about what it would be like to kiss her again. How he longed for her to know his true feelings. He wanted to be able to touch her, kiss her, make love to her. His heart raced thinking about being naked with Pam. He imagined undressing her, touching her breasts, gently laying on top of her, and making slow passionate love to her. Jim moaned out loud in pleasure and grabbed the mattress with his free hand. His semen shot out of his cock like a canon and landed on his stomach. His head fell back onto his pillow and he felt a chill come over his body. He took a deep breath and exhaled slowly.
Now this was the part he hated. His emotional high was over and Jim was left with the realization that he was alone in his room. Pam was probably lying in her own bed right now with Roy lying next to her. The woman he loved was not his. Pam was his best friend and he couldn't even be honest with her. He didn't know how he could go another day pretending his love for her wasn't eating him alive inside. He couldn't concentrate at work. Even his apetite had changed. As much as it pained him, he wasn't going to make a move on an engaged woman. Jim knew Roy wasn't right for her, but he had to wait and hope that Pam would soon figure that out for herself. It had to be her choice. She had to come to that conclusion on her own. And when she did, he would be waiting for her. He had no choice but to wait...