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serenefreakgeekao3 · 2 months

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Ambivalent Days

Jim Halpert x Trans Man Reader (PART TWO) Can be read alone, but I do reference part one, so read that HERE if you want to be caught up!

Summary: You’ve finally come out as trans to the entire office. It’s gone a lot better than expected. But now you’re faced with a serious problem- or rather, a serious crush. On none other than Jim Halpert, leading supporter of your transitions and quickly becoming your best friend in the office. But are you willing to risk that friendship just for some silly little feelings?

Tags: FtM!reader, Gay!Jim (for narrative reasons, I think i wanted him to be bi in the first part but switched it around, whatever), implied gay!reader (all i said was ‘not straight’), trans supporter Dwight, peacekeeper!Pam, supportive!Kelly Kapoor, bisexual!Kelly, drinking in moderation, happy ending Warnings: Michael being absolutely ridiculous and attention-hungry to the point that he does bad things (so, like, normal episode?), some general swearing

A/N: This has been requested so many times, both in asks and requests. I’ll try my best to tag everyone who asked for this, sorry if i forgot any! I was excited to write this because I loved the first part, but figuring out where to start was the trickiest part. I hope you all enjoy! (this entire fic ended up just writing itself once i got going. I had no clue what i was gonna do until it happened so… enjoy lol)

Life was great, working as a Customer Service representative for Dunder Mifflin paper company. Wow, you never thought you’d say such a thing, but it really has become something appealing, something that had you smiling and willing to come to work every single day. Of course, it had its own ups and downs, times when you felt overwhelmed or frustrated at certain people. You still ended up enjoying the majority of the day, and sometimes the rough days turned out to end up better than the rest.

It had absolutely, wholeheartedly nothing to do with James Duncan Halpert, otherwise known to his work colleagues as ‘Jim.’ You continued to lie to yourself, nodding along to this thought process on your drive to work. It was rainy, just like most days, and you were bored out of your mind waiting in the traffic. You just enjoyed going to work, because… Because of all of your friends, that’s why! Sure, that might include Jim, but that also included Pam, and Oscar, and god forbid, even Dwight. He’s certainly grown on you over time, having completely accepted your identity, even defending you against anyone who said anything. You couldn’t be sure, but you suspected that Dwight had even lost a customer through those actions- but when Mr Dellicker had called for customer support and you had answered the phone, saying his name out loud, Kelly had rushed around the divider and ripped the phone from your hand, immediately transferring it to her own phone. You tried to listen in, curious why this was so important to her, but you kept hearing her say the same thing over and over.

“Thank you for your consideration, but we no longer want your business with us. I completely understand that you think so, but we no longer want your business with us. While that may or may not be true, this whole conversation is futile considering we no longer want your business with us.”

Mr Dellicker had become a hushed topic around you, but you had managed to catch a private whisper among your friends one day when he was brought up again. They’d ask Kelly if he had called yet, and she assured the situation was handled. Pam had whispered, “I can’t believe some people’s views on trans people. It makes no sense.” So, while it wasn’t likely due to you specifically, you were almost sure that you were the only trans person they knew. If they were defending trans people, they were defending you alongside it all.

You pulled into the parking lot finally, shaking your head to rid yourself of those thoughts. Mr Dellicker’s whole deal had been a problem a month ago and was no longer an issue. You shouldn’t dwell on those thoughts, you weren’t likely to ever have to worry about it again. You managed to snag a semi-decent parking space. It was only the second from the front, but it happened to be right next to Michael’s own car, and as you placed your car into park, you glanced over to notice he was still sitting there. You tilted your head in confusion, watching for a moment.

You couldn’t tell if he was psyching himself up, or singing along to one of his weird songs. He seemed ready to open the door, then leaned back once more without actually doing it. He lowered the visor on his car, flipping open the little door to reveal his mirror and looking at himself in it. He continued, probably, speaking to himself, and you just shook your head and decided to leave it be. You reached for your suitcase and umbrella, then began making your way inside.

You were stuffing your umbrella into the little holder by the door after you entered the office, taking off your long overcoat and hanging it on the coat rack by Pam’s desk. She smiled, asking about what you did over the weekend, and you answered that you didn’t really do much besides binge the next season of your current obsession. You agreed to tell her about it later, moving toward the break room for your normal cup of tea. You pat Jim on the shoulder on the way, and he reaches up quickly to touch your hand before you slip by. It causes a smile to cross your face as you continue on your path, a happy feeling welling up inside.

“I. Am a girl.” You spin around quickly, eyes widening in fright. There stood Michael Scott, wearing a short, pleated pink skirt with his normal yellow button-down dress shirt, as well as a crooked ginger wig that he had most definitely not been wearing in his car. The room falls completely quiet, and you hear two people put their calls on hold. Jim stands, and you can’t see his face from this perspective, but you hear a hardness in his voice.

“Michael, this is not a funny joke-”

“It’s not a joke!” Michael yells out, crossing his arms. He purses his lips before speaking again in a higher tone. “I’m a girl, and so I decided to say it. That I am.” He looked around the room as if expecting something, but no one moved a muscle. Pam broke the silence, clearing her throat and talking in a tone that was both cautious and unbelieving.

“Alright, so what would you like us to call you, then?” Michael sputtered at the question, throwing his hands outward and looking around the room again. His eyes settle on me, and Jim sidesteps to block off his vision. You can no longer see Michael, but the image of him has burned into your mind anyway. You could feel yourself panicking, your heart trying to beat its way out of your chest. This had to be a prank right? He was making fun of you? Now? After all this time?

“What do you mean- Y/N didn’t change his name when he came out!”

“This has nothing to do with Y/N,” Jim quickly tries to interrupt him after hearing your name, but you heard his sentence all the same. Jim walked closer to Michael, leaning down to whisper, but even you could still hear his words in the silence your boss caused. “How about we talk this out privately and continue this announcement later?”

“But-”

“I think that’s a fantastic idea, Jim,” Pam calls out quickly, circling her desk and corralling Michael into his office. He was putting up a fight, but not much of one. Jim followed closely behind, closing the door behind him. You could see multiple faces turn to look at you- as their current entertainment had been dragged away- out of the corner of your eye, but you were still there, shell-shocked. Before you realized what you were doing, you were standing directly outside Michael’s office door, peeking around the side to look in through the window. You could hear them talking still, considering the rest of the office was waiting to see what you would do.

“No, no, no!” Michael yelled out, plopping down into his seat. “I’m serious about this you guys!”

“Alright, let’s assume you are,” Pam begins, but Jim looks at her with an aggravated look.

“Pam-”

“Let’s assume you are,” Pam repeats, pushing Jim away and leaning closer to Michael. “How did you come to this decision?”

“I-” Michael hesitates, looking at his computer, then back to Pam. “Well, I really like girls a lot.”

“Sure, sure, but sexuality and gender are different.”

“I know that, Pam! God!” Michael starts flipping random pens on his desk, trying to distract himself. “I just like their clothes a lot.”

“You like to wear the clothes, or see them on women?”

“See them-” He stops, looking up to her. “I mean, wear them! Yeah, that’s what it is!” His stuttering and determination caused Jim to huff in a humourless laugh, no longer just standing by.

“What’s really going on here Michael?”

“And,” Michael begins, ignoring Jim’s question, “What was that question about what I wanted to be called? Y/N didn’t change his name when he came out?”

“Sure,” Pam agrees, trying to maintain the peace, “But Michael isn’t a very feminine name. Doesn’t that make you feel a little, I don’t know, dysphoric?”

“What does that word mean?” Michael asks, causing Jim to huff again, moving forward to slam his hands onto the table.

“What is really going on here, Michael?”

“Fine!” Michael yelled out, throwing up his hands, his fake hair swinging around wildly. “I don’t think I’m a girl! I don’t like wearing dresses or skirts or-” He spits, swatting away the fake hair that had managed to catch itself in his mouth, “And I’m so uncomfortable in this,” He pulls the wig off finally, throwing it onto the ground. He stands next, reaching for the skirt he was wearing, “Or this-”

“No, no, no!” Pam calls out quickly, keeping him from ripping the skirt off in front of them. “I’ll fetch you your spare pair of pants here soon, it’s at the desk. Just,” She sighs, shaking her head, “What could’ve possibly made you think this was a good idea, Michael?”

“Well!” Michael huffs, pouting as he sits back down. “Y/N got all sorts of attention when he came out. He became cool, and popular, and now I’m not even allowed to make jokes about him! Everyone hates me now, he took my thunder!”

“You can still make jokes about him,” Pam continues cautiously, raising her hands up in a plea to calm him down. “Just, not about the fact that he’s trans.”

“My thunder Pam!”

“This is fucking ridiculous,” Jim begins, reaching forward and grabbing hold of Michael’s shirt. “That stunt you pulled was mean-spirited and heinous. Do you have any idea how you could’ve made Y/N feel? How hard it was for him, not only to accept himself for who he is but to become confident enough in himself to come out to the entire office? Do you realize how much you probably just put him back?” Michael’s face was terrified, and Pam was too stunned at this action to do anything at first. By the time Jim was done talking, she reached forward quickly and pulled him back.

“Jim, that’s unnecessary.”

“I feel it was completely necessary, Pam.”

“He doesn’t realize what he’s doing, he just wants attention.”

“He gets attention every single day Pam! He demands it, hell, he goes out into the office and-”

“Jim,” Pam interrupts, nodding toward Michael. You watch Michael visibly sniff, raising a hand to rub at his nose.

“No, no, he’s right. I’m a nuisance, everyone hates me.”

“No one hates you, Michael,” Pam starts, and Jim scoffs.

“You’re babying him.” She shoots him a threatening look, and he just shakes his head and crosses his arms. Pam moves closer to the desk, looking down at Michael.

“Hey,” When Michael looks up, his eyes are red and glossy. “What you did just now, was that a good idea?”

“No,” He whines out, drawing out the vowel.

“Good, that’s the correct answer. And why was it a bad idea, Michael?” He huffs again, moving to play with a different toy on his desk and avoiding her eyes.

“Because I lied for attention.”

“And?”

“Because I probably made Y/N feel bad. And Jim.”

“So what are you going to do?” Pam asks, and you can’t see her expression but Michael finally meets her eyes and breathes in a deep breath.

“I’m going to tell everyone that it was a horrible prank and that I’m sorry.”

Even Jim startles at this, both Pam and Jim- even you, yourself- having never actually heard Michael apologize for one of his many failed pranks or skits. Pam straightens up, glancing quickly at Jim before looking back. Her voice was full of surprise as she nods, “That’s right. That’s completely right, actually. Good job Michael.” You could see him smile before looking down at his lap, then back up at Pam.

“Can I do it after I change?”

“Of course,” Pam moves quickly to the door, and you don’t think fast enough to move out of the way. The door swings open wide and you are revealed to be standing there, right outside of it. All three occupants turn to look at you with varying expressions, but they all share a similar surprise. You swallow hard, locking your eyes with Michael. You are about to speak but can feel eyes digging into your back, so you take a few steps into the office, past your two friends.

“What you did just now,” You begin, sucking in another deep breath, “Was horrifying- for everyone involved. I’m sure we want to see you in a skirt just as much as you want to be in one.” You lean forward onto the desk, watching Michael shrink away from you. “But let me ask you, how does it feel to wear that skirt?”

“What?” He looks startled at the question, looking to Jim and Pam for help. None arrived for him.

“How does it feel, wearing that skirt? Why aren’t you wearing a blouse with it? Couldn’t find one that fit, or did it feel too uncomfortable? What about the hair?” You nod down to wear the wig laid on the ground. “Was it annoying? Kept getting caught in your mouth, right? Drooped in front of your face, obscuring your vision?” You leaned forward, your breath coming out harsher. “Imagine you had breasts attached to you- and push past your sexuality. Imagine you had them and they couldn’t be removed.” You whisper this last part, your own eyes tearing up. “How would you feel?’

You hear Jim say your name softly behind you, realizing what you were referencing. Michael shook his head for a few seconds before he stopped, widening his eyes. You nod, continuing your speech. “Yeah, exactly.” You lean back, picking your hands off of his desk to rest by your side. “That’s how I feel every single day. Or, did. Until I came out.” You take a deep breath, steadying yourself. “I became confident because I was finally comfortable with who I was. I’m sorry if you can’t find that confidence in yourself. But don’t try to steal mine. Don’t make a mockery of my struggles.” You turn, heading toward the door, toward your desk- to anywhere but here. But Michael’s voice stops you before you’re able to leave.

“I’m sorry, Y/N.” You turn, looking into his eyes. He seemed genuine, but you knew he didn’t really understand.

“Think about why you are. Then get back to me.”

You pushed your way past Pam, who stood in the doorway with shock and pain written across her face, and ignored Jim’s call of your name as you kept going. You wanted away from these stares, this was not what you meant by loving this damned office. You continued past the breakroom, ignoring your daily cup of tea. You enter into your side of the annexe, seeing Kelly on the phone and hearing a whispered but high-pitched, “What? No! He didn’t?” Before she suddenly looks up, widens her eyes, and quickly says, “Gotta go,” Before slamming the phone down. You sigh and walk around the divider, taking your seat.

Kelly has more social sense than most people in the office, you’ve come to realize. It was why she had applied for customer service- unlike you, who had just taken up an ad from the newspaper. So, she knew better than to try to ask you what happened. She remained quiet on her side of the partition, something that was extremely odd, and it almost felt like you were in your own little world, in your tiny corner. Your desk was pressed against two walls, and the partition blocked the other two sides except for the small gap for your entrance. The partition walls weren’t very high, but sitting down they reached above your head. You felt isolated- something you first loved, then hated, and now feel grateful for once again. It gives you time and privacy to calm down.

After some time, you hear a throat clear nearby, and Kelly’s chair roll as she likely stands to leave. You look up at the top of your divider, waiting for a face to come into view. Luckily, it’s Jim’s face. He smiles softly at you, and you can tell he’s trying to keep the pity from his face, but it's not working very well.

“You didn’t make your tea?” He raises a cup- your favourite cup, no less, that no one else has used since your incident with Dwight- and offers it to you. “I figured I’d make you some. Can’t go a day without your tea, right?” You can tell he was trying, and it warmed something inside of you. Trying for a smile, you reach out to take the cup, taking a sip. It was made perfectly.

“I’m sorry about that,” You begin, sighing and placing the cup aside. “I kinda went a little overboard, didn’t I?”

“Not at all,” Jim rushes to comfort you, circling the divider completely to be inside your little cube. He rests himself against your desk, looking down at you with earnest eyes. “If anyone was overboard, it was Michael.” You just shrug, looking away.

“I mean, what did I expect, really? Everyone in the office has been so good about the whole thing. Ever since I’ve come out, it's been nothing but positivity.” You bite your lip, shrugging. “This office isn’t exactly a positivity-friendly environment.”

“You being trans should have no bearing on your workplace,” Jim insists, leaning forward toward you. “I know the world is fucked, but I want to make sure that at least your world isn’t.” You huff a laugh, shaking your head.

“Oh, c’mon Jim. Don’t be too hard on yourself.” You look up, meeting his eyes with a self-deprecating smile. “It’s not like it's because of you that all of this ended up so easy until now.” Jim’s eyes widen slightly, then wander away as he wiggles his head and bites his lip. You wait for him to agree, then narrow your eyes. “You… Didn’t tell everyone to be nice to me, did you?”

“Well,” He begins, drawing out the word and wincing. “I didn’t quite do that. But I did explain that they shouldn’t act any different, what jokes they shouldn’t make about it, and to look something up before asking any questions. If they couldn’t find the answer online, then they could ask me, and then I would allow them to ask you.” You blink a few times, tilting your head.

“But no one ever asked me anything?” He nodded along, sucking his lips inside his mouth before popping them, sighing.

“Yep.”

“Did they have questions?”

“Oh,” Jim scoffs, laughing. “So many.” He places his hands between his knees, palms together. You couldn’t help but laugh with him.

“Like what?” You feel curious but also dread at the prospect.

“Oh, y’know,” Jim shrugs, moving to mess with some pens on your desk idly, not meeting your eyes. “Just the usual dumbest shit on the planet. I told them all they were absolutely not allowed to ask you, of course, and had to explain why sometimes.” You nodded along, huffing out another laugh.

“I suddenly don’t want to know.”

“Oh, no, you really don’t.” You laugh softly along with him, feeling your chest bloom open, your crush developing further. For the second time today, you were moving before realizing you decided to. You stood, then reached forward and pulled Jim into a hug. He had straightened when he noticed you standing, then stood stiff as you wrapped your arms around his shoulders. You hesitated, about to pull away when Jim moved quickly, wrapping you in his arms and pulling you in tighter. You relaxed once more, laying your head against his chest and closing your eyes.

“Thank you, Jim,” You whisper, turning your nose to brush against his dress shirt. He smelled clean, with a hint of cologne that you couldn’t place. His arms were warm and strong- comforting in a way that you hadn’t felt in so long. He moved one of them up, cupping the back of your head as he straightened up more, pulling you in closer.

“It’s nothing,” Jim stutters out, and you can hear his heart beating under your ear. “Someone’s gotta make sure these folks don’t chase you away.” You laugh, leaning back to look him in the eye. He seems sincere, solemn, as he adds, “I think I would be devastated if you quit.” You chuckle once more, shaking your head as you pull away.

“Oh, I’m sure.”

“No,” Jim lowers his head, trying to catch your eye once again. “I’m completely serious. You are probably the only reason I still show up.” He laughs, shaking his head. “I mean, I’m this old and stuck in this job?” You laugh along, shaking your head.

“You make good money here, Halpert, don’t deny it.” You feel slightly upset you had pulled away from the hug so soon, but you had to look at him after he said that. You had to see if he was serious- Jim is hardly ever serious, always joking around. It was part of the reason your crush developed so fast, and also why it’d always remain a secret. He was so funny, making you laugh constantly. But he was also a bit of a jokester, and you didn’t know if he had a serious bone in his body. Today was showing he certainly did.

You weren’t sure if you’d be able to handle it.

You both spend some more time chatting, and his presence is a balm that soothes your panicked heart. He tries his best to make you laugh- which you do, often- and you finish your morning cup of tea in the meantime. You were sure you could’ve talked to him forever if only your phone hadn’t rung. You shrug with helplessness, reminded that you’re technically at work and still have a job to do. You reach to pick up your phone, apologizing to Jim who waves you off. You watch him walk away as you answer the phone, “Dunder Mifflin paper company, customer service representative speaking.”

It ended up being a quick call, with someone complaining that their shipment was late. You only had to find their account to let them know that the delivery was scheduled for today and the time. Once you placed the phone back in its slot, you raised your cup to your mouth before remembering it was empty. ‘Eh, might as well,’ You think to yourself, pushing to stand and make your way to the breakroom. Kelly is back at her desk as you circle around, and you make sure to say a soft greeting to her to make up for your earlier rudeness. She says a polite and short greeting back with a gentle face, still conscious of your rough morning.

You’re about to pull the door to the breakroom open when you notice the back of Jim standing at the counter. He was hefting a freshly brewed pot of coffee, and you couldn’t help but stand there and watch his arm flex as he hefted it with no problem. You didn’t see the other door open, but suddenly Kevin was walking directly into Jim’s space.

“I have another question.” Jim sighs visibly, shaking his head.

“Haven’t I told you enough-”

“No, this is a different question, Jim!” Kevin seems adamant, and after Jim puts the coffee pot away he takes a side step to regain some personal space. “And you said yesterday there’s a limit of stupid questions I’m allowed to ask a day so I couldn’t ask yesterday!”

“You have until I finish making my coffee.” You’ve never seen Jim quite so indifferent and snappy before, raising your curiosity. For some reason, you still stood there, barely peeking through the window of the door, still holding your empty cup.

“Ok, so if he still wanted breasts-”

“Nope.” Jim was already shaking his head, stirring sugar into his coffee.

“Alright fine, but also. Can he sow a penis-”

“Nope.” Kevin huffs in frustration, flapping his arms for a split second.

“Why do you keep saying no to all of my questions?” Jim finishes stirring his coffee, placing the spoon in the sink and turning to look directly at Kevin finally.

“Because all of these questions are way too personal.”

“How are they personal?” You tilt your head, furrowing your brow. How would they not be personal? Jim seems frustrated, running his free hand through his hair.

“You can’t just ask someone about their breasts or genitals, Kevin. You wouldn’t want anyone asking about your dick.”

“Actually, it’s kinda itchy-”

“Nope!” Jim pushes away from the bar, leaving immediately. You’re stuck between sympathy for both of them. You don’t think Kevin actually knows any better at this point, but you also just felt too awkward to even try to come up with an answer to those questions. However, were these the types of things that Jim had to put up with daily just to vet the office for you? Why would he put himself through all of that?

“He’s really trying, you know?” You startle from your thoughts, turning to look at Kelly still sitting in her rolling chair. You tilt your head in confusion, but also shifted on your feet, hoping to play off the fact that you’d been standing there this whole time.

“Who?” Kelly just gives you a look you can’t quite decipher, continuing.

“Jim, obviously.” She sighs, pushing herself away from her desk and standing. “He’s even asked me for help on occasion. Little things here and there, but he recruits the allies where he can find them.” You purse your lips, leaning back against the wall next to the door, crossing your arms while holding your cup upright still.

“Asked you for help? Doing what? Who else has he asked?”

“I knew you’d figure it out at some point, I just didn’t think it’d be when someone slipped through his fingers. Though, Michael is pretty unpredictable like that.” She shrugs with a smile like she’s trying to hold back a laugh. “His main ask for me was just to intercept anyone trying to bother you- most likely to ask the dumb questions. I just had to send them right back through the breakroom over to Jim’s desk.”

“Did that happen often?” She shrugs again, wiggling her head.

“Not often, but a few times. Mainly Kevin, he has a lot of questions.” You nod, glancing briefly toward the breakroom’s door before resting your eyes on her once more. You study her posture, then try to make a guess.

“The other was Mr Dellicker, wasn’t it?” She winces but nods nonetheless.

“He was a real ass.” She sighs dramatically, moving to lean against the wall next to you and bunching up one of the random, typical office posters that hang around throughout the floor. “He was Dwight’s client, actually. The moment Dwight heard him be even a small bit transphobic, he hung up the phone. This, of course, caught Jim’s attention. I mean, have you ever known Dwight to drop a client? Like, ever?” You shake your head in agreement, and she nods with you. “Yeah, right? Anyway, Jim asks, Dwight answered. To Dwight, that was the end of the entire thing. To Jim, however,” Her smile begins growing as she leans closer to you, “Well, he knew that Mr Dellicker would call back to complain. And who would be picking up the phone?”

“Customer service,” You mumble, absorbed into her story.

“Exactly!” She giggles now, unable to hold it back. “It was adorable, really, the way he begged me to make sure I took his call. He actually asked me to call the man first, but I told Jim I wouldn’t go out of my way just to aggravate someone who, as far as we knew, wouldn’t be calling back after such a rude hang-up. But he wouldn’t let up, so I agreed to keep an ear out.” She huffs now, widening her eyes with a far-off look. “Good thing I did, too. He was such an ass.”

“Thank you,” You say softly, bringing her back to the present. She tries to brush it off but you just shake your head, placing a hand on her arm. “No, not just for Mr Dellicker. For agreeing to help out at any point, just for me. For not making a big deal about my whole coming out, for never treating me any different or- just-” You hesitate, shaking your head. “Just everything, Kelly. You’re an amazing coworker.” You watch her eyes begin to water, and she lets out a wet laugh.

“Wow,” She raises her hands, wiping the corners of her eyes. “You’re going to make my makeup run.” She pushes up from the wall, circling you and entering into the breakroom, heading straight for the girls’ bathroom. You widen your eyes at this reaction, unsure, but take a deep breath and enter into the breakroom yourself. You still had some tea to brew.

You didn’t mean to idle, standing near the exit of the breakroom toward the annexe, but stuck in place watching Jim lean against Pam’s desk through the door’s window on the other side of the room. They were talking back and forth- a lot of laughing involved- and you couldn’t quite place the feelings whirling in your chest. It felt similar to jealousy, but you knew that wasn’t it. Envy? That perhaps she was his type, and not you after your transition? Insecurity?

You startle as Jim suddenly meets your eyes, watching him straighten up quickly. You try to act nonchalant, moving out of his line of sight to grab your lunch from the fridge, and sitting at the break room table. You’d finished your second cup of tea hours ago, and you were a tad overdue for your lunch break considering you had a whole host of emails that you usually respond to in the morning, but had to answer during your second cup of tea since you’d been just a tad distracted that morning. You bite your lip as the events from that morning fly through your mind, a whole host of emotions attached to them.

The door across the room opens, stopping your train of thought in its tracks. Jim walks in with a smile, moving toward the fridge. “Hey,” He greets you, scanning you with his eyes while you just sat there, slowly removing your lunch from its brown paper bag. “Was starting to worry you’d forgo lunch.” You laugh, then proceed to explain your lateness. As he sets his own lunch on the table, you begin to wonder if he waited for you. Then your eyes flicker back toward the door you’d been staring at him through.

“So, how’s Pam?” Jim seems a bit taken off guard at the question, turning to look at the door himself before looking back to you. He shrugs, taking his own lunch out of his lunch box.

“Uh, good, I guess?” He raises his sandwich, ready to take a bite before hesitating and adding on, “She’s excited to hear about that one show you mentioned this morning.” You nod along, watching as he begins to eat his sandwich. You take your own small bite, looking toward the door again.

“She’s cute, isn’t she?” Jim’s eyebrows furrow immediately, and you watch him swallow. He seems to be planning his actions in his head before he performs them, placing his sandwich down.

“What?” He looks around the room aimlessly, wiggling his head. “I mean, yeah of course. She’s cute.”

“You two get along really well.” At this he chuckles, shrugging.

“We’ve worked together for a long time.” You both fall silent, taking more bites of your food. Jim breaks the silence with a resounding, “I’d probably have developed a crush on her by now if I wasn’t gay.”

Gay.

You end up lightly choking on your bite from surprise, playing it off with a cough and a sip of your water bottle. You can see Jim staring down at his sandwich at the table, taking a deep breath. “So, I can see why someone would develop a crush on her. If he was straight.” He glances briefly up at you, then back down to his sandwich. You tried your damndest to keep the look of shock from your face, that it takes an extra minute before you understand what he’s not saying. Did he think you were asking because you had a crush on Pam? You take another sip of water, letting your eyes wander away from him.

“Yeah, same.” Out of the corner of your eye, Jim glances up at you quickly, a look of concentration on his face that indicates his thoughts roaming a million miles an hour. You shrug for show, moving your own food closer so you can take a bite once you finish speaking. “I’d probably have developed a crush as well if I was straight.”

You only recognized the signs of Jim choking since you’d just gone through the same thing, as the man turns to cough into his arm as if to play it off. At least the poor man hadn’t been chewing food like you were. By the time Jim finished drinking from his own bottle, and moved to lean forward and say something, he was interrupted by the door opening and someone entering inside. He leans back, looking self-conscious, and you feel such a deep curiosity about what he was going to say that it burns in your chest. You don’t even register who walked in until she was taking a seat right next to you.

“I don’t know how you can stand it, Jim,” Kelly begins softly, and you look at her with confusion. Kelly never talks softly? “Working right next to the receptionist's desk all day. How do you get any work done?” Jim’s eyes flicker between you and Kelly, clearing his throat.

“What do you mean?”

“Well, she’s so hot!” You and Jim meet eyes suddenly, listening to her continue to talk in a soft voice. No wonder, considering she was essentially coming out to the both of you. “When I first started and had to work over in that area, I was getting nothing done. Toby had to ask me what was wrong, and I sorta kinda told the truth that I was extremely distracted. He moved me to the annexe-” She pauses here, resting a hand on your arm with a sympathetic expression, “Sorry, Y/N, that’s why you’re confined back here as well.” You shake your head quickly, rushing in.

“No, it’s fine. I like it back here.”

“You do?” Jim asks with a smirk, and you give him a look essentially saying ‘Shut the fuck up Halpert I’m trying to console her.’ He just laughs noiselessly, his chest shaking as he moves to take another gigantic bite of his sandwich.

“Anyway, it’s so distracting. I had to go get something copied and I stood there an extra five minutes trying not to stare too directly at her. Oscar literally had to nudge me and remind me what I was doing!” She groans, letting her head fall onto the table. “So embarrassing.”

“Oscar knows?” You ask gently, unsure whether she actually realized she told you both. She lifts her head with a sigh, seemingly unfazed.

“Well, yeah. Oscar knows about everyone.” You hear Jim scoff softly, mumbling quietly under his breath.

“Not everyone.” This only causes Kelly to raise an eyebrow at Jim, smirking with humour.

“Oh, he knows about everyone, Jim.” His head was quick as it whipped toward Kelly, leaning in.

“Wait, what?”

“I mean,” She shrugs, glancing toward you briefly before meeting his eyes again. “You’re kinda obvious, Jim.” You can see his eyes widen, but you only feel confusion.

“Wait, how many people are gay in this office?” Kelly only shrugs, refusing to meet your eyes.

“Not my place to say.” You nodded along, obviously that being true. You meet Jim’s eyes once again, and you can see red peppering his cheeks.

“I’m sure it’s fine, Jim.” He nods as if agreeing, flicking his eyes between you and the rest of his sandwich throughout the rest of lunch. Kelly takes the initiative in the ensuing silence, talking about everything yet nothing at the same time. Just as you and Jim are both cleaning up to get back to work, Kelly sighs loudly with an eyeroll before looking toward you and plastering on a smile. The look only made you feel wary.

“So, Y/N, what are your plans for after work?” You swallow roughly, glancing at a wide-eyed Jim, then back to her.

“Uh, nothing really?”

“Oh,” She draws out, reaching forward and placing a flirty hand on your arm. “So you’re free tonight? Want to go out for drinks?” You stutter, pulling away from her arm, your head already shaking as you try to come up with an excuse. ‘Didn’t she just say that she found Pam attractive? What the hell is going on?’

“Uh, Kelly-” Jim tries to intercept, but she pulls away as if nothing happened, shrugging.

“I just meant with the lot of us. Jim will be there too, won’t you Jim?” She looks directly at him, raising her eyebrows as if she was expecting something from him. You look between the two as an awkward silence settles before Jim startles, trying (and failing) for a normal smile.

“Oh! Those drinks!” Jim laughs awkwardly, looking back and meeting your eyes. “Yeah, we’re all going out for happy hour at Poor Richard’s Pub, you should join us!” You relax slightly as Jim was the one offering, no matter how weird this entire interaction ended up being.

“Oh, uh,” You hesitate, still slightly wary. There’s obviously something you’re missing here. “I mean, sure. I have nothing else to do. Who all will be there?”

“Just a couple people from the office,” Kelly quickly answers, standing and moving to throw her own trash away. She turns to look at both you and Jim, still sitting in your chairs. “Well, c’mon! We have work to do, people!”

“I know why I’m sorry now.” You startle at your desk, turning to look directly at Michael Scott with wide eyes. You hadn’t even heard him approach. He circles around your desk, motioning for you to stop your work as he leans against your desk- an unknowing imitation of Jim that morning. “If you’re willing to listen?”

You can feel yourself swallow roughly, the beginnings of a familiar panic starting in your chest. You’re unsure what to say, so you just nod. He nods as well, taking a deep breath before continuing. “At first, I had no clue what you meant. I knew I was sorry, and I knew it was because I had hurt you.” He looks into your eyes, regret deep within his own. “But that wasn’t enough for you. So I started thinking.” He chuckles softly, leaning back on his hands and letting his own gaze roam the walls behind your desk. “And when that didn’t work, I remembered something Pam said when she tried to play along with my- well, yeah. A certain word I didn’t recognize. Dysphoric.”

You feel yourself tense, suddenly remembering the tightness around your chest where the binder lays under your clothes. You can feel the tie around your neck like it was trying to choke you. Michael, unaware of your inner struggles, continues on. “That search was enlightening- it was like everything you had expressed to me. And everything I had felt, trying on those clothes.” He hunches inward, his expression becoming stormy. “I felt so wrong wearing that skirt. And you were right- I had tried a blouse on. I bought one at the store that fit and even brought it home, but it just felt so weird when I tried to walk out of the door with it on. So I switched to my normal shirt.

“Then I was sitting in the parking lot, and I knew that the moment I placed my foot out of my car, everyone would see the skirt. I was-” He laughs humourlessly, shaking his head. “I was terrified. I tried to ignore it- like it was just stage fright, something I had to talk myself into.” You began to nod, intrigued by his story. “I don’t know how I convinced myself to get out of the car- I guess something along the lines of, ‘Well, I’m the boss. The ship will sink without me in there.’” He takes a deep breath, patting his legs loudly. “Anyway, I was jealous.” He shrugs, looking at you with wet eyes. Was he really getting emotional over this? “I mean, you did kinda steal my birthday away from me.”

Memories of that night flash quickly through your head. You’d come out during a party- a party you didn’t know the purpose of. That pink quinceañera cake… You didn’t get to taste it, but they could’ve gotten it because it was his favourite flavour? You hadn’t even seen Michael there. Was he trying for a grand entrance? Memories from this morning flash through your mind’s eye, Michael yelling at Pam, ‘He stole my thunder! My thunder, Pam!’

“It wasn’t planned, Michael,” You try to assuage, wincing despite yourself. “I’m sorry, though.” Your apology causes Michael to blow a sigh out roughly, then laugh and slap his thighs again.

“Wow! I didn’t know how much I needed to hear that.” You’re both silent- you studying Michael’s face, and Michael looking anywhere but at you. Then you start laughing.

“Michael,” You try to talk through your laughter, but you just shake your head and try to get it under control. You wouldn’t want him to think you were making fun of him- you only found him ridiculous- so you try your best to calm down. “Michael. You were upset that I ‘stole your thunder’ on your birthday, so your response was to… Pretend to be a girl? Instead of, oh I don’t know,” You try to hold back your laughter again, choking lightly on your words, “Throwing another party?” Michael seems to take a moment to absorb this- then begins to laugh alongside you.

“Well, that would’ve only been easy, Y/N. When have you known me to do things the easy way?” You both laughed again, and you began to shake your head.

“Never.” When your laughter finally dies down, you meet his eyes once again. Staring at each other, it's like you both finally understood. You thought he was just ignorant, but you had been missing out on important information as well. He began to nod, glancing over his shoulder toward the nearby wall clock.

“Well, looks like I kept you long enough. Time to clock on out!” He jumps up, shooting finger guns before backing up. He trips over the edge of the divider, tries to play it off, and then groans loudly when he sees Toby walking by. “God, every time!”

You chuckle to yourself, then begin the process of shutting down your computer and packing up. Kelly skirts around the divider quickly once the door closes behind Michael, leaning into your space. “Let me drive you.” You hesitate, widening your eyes.

“I’m sorry?”

“To the pub! Let me drive you!” You laugh nervously, beginning to shake your head.

“Oh, uh, no. I have my own car, but thank you-”

“If you drink, you won’t be able to drive home.” She counters, raising her eyebrows at you. You laugh again, shaking your head.

“Well, if we’re all drinking, wouldn’t you drink too?” She shakes her head immediately, crossing her arms.

“I don’t drink at all.” You still feel hesitant, and it must show on your face as she sighs and then leans in. “I’ll tell you Jim’s whole deal.” This catches you, looking back at her to study her.

“What do you mean…?”

“I’ll tell you if you let me drive you!” You huff a laugh, smiling despite yourself. “Yeah, alright. But if I don’t drink, you gotta’ take me back here so I can drive myself home.”

“Deal! And if you do, then I’ll drive you home and pick you up for work tomorrow morning!” You laugh again, shaking your head as you pick your briefcase up, finished with closing down your desk for the day.

“You seem excited about this.”

“Absolutely! I’ve been waiting forever!”

You were still unsure what she meant but followed along with the hyperactive girl as she burst through both of the doors to the breakroom. You watch Jim straighten where he had been leaning against Pam’s receptionist's desk, and smile toward you as you made your way to the exit.

“You know,” Jim starts, huffing a soft laugh and smiling in a way that took your breath away, “I was thinking.”

“Oh,” You draw out, smiling despite yourself, “Dangerous territory there, Halpert.”

“Yeah, yeah,” Jim begins, laughing again. He takes a discreet look around before reaching forward to almost take your hand, his fingers tangling with your own but not quite grasping. “I was hoping that maybe I could drive you down to the pub? I know you have your own car and all, but I just want to make sure you’re safe with getting home, y’know?” Your face falls just as you hear Kelly’s voice behind you.

“Oh, don’t worry Jim! He has a ride already.” Jim looks toward Kelly over your shoulder, then back to you with wide eyes, pulling his hand away.

“Already?” Jim looks back to Kelly, confusion clear across his face.

“Oh, don’t get your panties in a twist, Jim!” You feel her small hand wrap around your bicep, pulling you toward the door. “We’ll meet you there!”

You take one last look at Jim through the glass doors as Kelly drags you along to the elevator. You hesitate, mind trying to catch up, before you finally clear your throat and look at her. “No offence here, Kelly, but I honestly think I would’ve preferred riding with Jim?”

“You’ll have the rest of your life to ride with Jim. Just let me tell you what I need to tell you without the risk of Jim hearing us.” You both step onto the elevator, as Kelly begins mashing the button for the lobby.

“Uh,” Your mind is stuck, repeating ‘rest of your life’ and ‘Jim’ over and over. “This feels… Is this nefarious?”

“‘Nefarious,’” Kelly mocks, pulling you once the doors open again. “You say the oddest things sometimes.” You didn’t know which car was hers, but considering she was dragging you along, you didn’t have to guess. She pulls your briefcase from your hands, finally letting go of you, and you just stand in place. She throws your suitcase and her purse into the backseat, then opens the driver's door with a look up at you. “Well, get in!”

It was quiet for a long portion of the drive. You didn’t know what to ask, or how to even broach the subject. Did it seem too eager, to ride along with her just because she promised to tell you about Jim? And what was she even talking about- how would Kelly know more about Jim than you? True, you both hadn’t been friends for very long just yet, but you didn’t know Kelly and Jim were friends?

“So, it started when you started transitioning,” Kelly said, bursting you from your whirlwind of questions. “We all got pretty curious. I was the one who had the theory you were trans first.” She winces, looking over to you. “Sorry. I didn’t know at the time how true I was. I honestly didn’t even know if you knew about it, but- well, obviously you did.” You tilt your head, brow furrowing.

“You all were talking about me before we were friends?”

“Well, you know how the office is. You were changing, and people were noticing. Especially Pam and Jim. Pam, who is such a sweetheart and just wants everyone to be comfortable. She had a feeling you were never quite comfortable at the office but didn’t know how to help. Jim found you hot, which was throwing him for a loop considering he is gay, and normally not attracted to-” She hesitates, tilting her head. “Well, we did think you were a girl at the time.”

You nod along, unoffended. “Right, but-” You scoff, shaking your head, “I don’t know if I believe this story now. I mean, Jim? Finding me-” You almost say the word, then scoff softly and look down to your lap. “Attractive?”

“Well, you are hot,” Kelly confirms, and you look up quickly at her. You aren’t sure what expression is on your face, but Kelly just laughs. “What? Don’t look at me like that! You were hot when we all thought that you were a girl, and you’re even hotter now that we know you’re a boy!” You laugh in disbelief, shaking your head. Kelly continues on, pushing through your awkwardness. “I mean, c’mon! Confidence is sexy as hell.”

You look away, feeling a blush rise to your cheeks as you remember Jim saying something similar. “Sure, but-” Kelly interrupts you, continuing with her story.

“So once you finally came out, Jim had his own little freak-out because it wasn’t just a theory anymore. It is true, you are a dude, and Jim didn’t know if he could handle you getting hotter and hotter every day.” You flashback to another scene in your head, Jim saying something similar to Pam and you laughing, accusing him of finding Dwight attractive. Was he talking about you at that time? Kelly’s voice brings you back.

“Anyway, I finally told him that he needed to get his act together and ask you out already, or I’d do it first. Either ask you out for myself or for him, but either way. I don’t know if I could stand any more of him spewing about you, I mean- all I heard was Y/N this, or Y/N that, or ‘Wow he’s wearing the tie I gifted him!’ I mean, that man can talk.” You hold back a laugh, shaking your head. The one and only Kelly Kapoor, complaining about someone talking too much. That’d be hilarious to tell Jim- if you ever got the nerve together to tell him about this little conversation.

“Ok,” You huff out, shaking your head, “You’re asking me to believe that Jim not only finds me attractive but wants to date me?”

“Well, that’s where we’re going now! So you better believe it.”

“Going now- but you’re here? The office will be there, how would it be a date?”

“It’s going to be a date,” Kelly starts slowly, looking at you with a grin, “Because it’s not an office hangout. I’m going to drop you off and leave, and then Jim can take you home. I only did this to get you both together outside of work, you’ll be all alone with him.” She huffs, squeezing the steering wheel around her hands. “And I’m telling you all of this before the date because I don’t trust Jim to admit anything to you without pushing him for it. If I’m not there to pressure him, then-”

“Woah woah woah,” You interrupt, shaking your head quickly. “I’m not about to pressure my best friend for- for some wild hope that he might feel the same. And I-” You can feel the panic again, pulling at the seatbelt around your torso. “I don’t know if I can do this, I didn’t know it would be just us, I mean-”

“Calm down, it’ll be fine. It’s just Jim, remember?” ‘It’s just Jim,’ You repeat to yourself as Kelly turns the car into the pub’s parking lot. You take a few deep breaths, nodding your head. ‘Yeah, I can do this. It’s just Jim, just normal ole Jim.’ Kelly backs her car into a space, waiting for Jim’s to arrive. It doesn’t take long to notice Jim’s car pulling in, parking in one of the front parking spaces, directly in your line of sight. You take another deep breath, nodding.

“I can do this,” You whisper, and Kelly reaches over to squeeze your arm. That’s when you watch two of the car doors open, Jim and Pam stepping out to take a look around. You hear a squeak beside you, Kelly’s hand tightening on your arm. You look over with concern, watching panic written across her face.

“Oh, Jim, you bitch,” Kelly whispers, shaking her head.

“This wasn’t part of the plan, was it?”

“Absolutely not,” Kelly whispers, then moves to get out of the car alongside you. You both approach the other two, smiles on your faces. They finally notice you, and it’s almost like you and Jim have locked eyes and thrown away the key. You’re unsure what’s really happening between the two girls, not registering the words exchanged. You walk a little closer to Jim, smiling up at him.

“Hey,” You whisper, and his smile widens, reaching his hand out in an imitation of earlier, tangling your fingers together.

“Hey.” He glances over to the other two girls, wincing and looking back to you. “I wasn’t sure- is it okay that I brought Pam?”

“Apparently,” You whisper, leaning closer and glancing briefly at Kelly to make sure she’s sufficiently distracted, “That wasn’t part of the plan. She told me she was throwing me out of the car and driving off.” You note the blush lighting up Kelly’s cheeks as she talks with Pam, before turning your attention back to Jim. You hadn’t realized you leaned in this close- or did he lean in as well? His face was next to yours, close enough to share a kiss.

“Shall we head inside? Guys?” You both jump apart, and you look guiltily over to Pam, who spoke. She only smiled in response, throwing a thumb over her shoulder. “We could grab a booth?”

The night was going well. It didn’t really feel like a date like Kelly had hoped it to be, but instead a nice get-together of a couple friends. You all laughed constantly, telling stories and jokes from the office, while also sharing your own life’s stories. No one really talked about their own life outside of the office while they were working, so it was a refreshing twist on things. You felt drawn even closer to the lot of them- Jim, especially, as he couldn’t seem to drag his eyes away from you for too long. You weren’t sure, but you thought it was Jim’s leg under the table pressing against your own. You hoped so, anyway.

“But, yeah, Toby is so weird! You guys don’t get that vibe?” Pam continues, giggling as she sips her mixed drink. Jim and Kelly were the only two keeping away from the alcohol, but you had ordered your favourite mixed drink and had slowly been sipping on it. You knew you weren’t drunk yet, but you were pleasantly tipsy.

“No?” You hesitated, trying to think back over the times you’ve interacted with him. It was more often than most since you worked in the annexe, but he always seemed like a nice, if tired, man.

“It’s cause he has a crush on you,” Kelly nods, laughing alongside Jim. Pam blushes, shaking her head quickly.

“Oh, no, of course not.”

“Well, Kelly would know,” Jim points out with a grin, raising his glass to his mouth and taking a large gulp. You watch confusion rush across Pam’s face, while Kelly’s turns a bright shade of red. She mouthed his name behind her cup, giving him a stern look.

“What does he mean by that?” She asks, looking between you and Kelly, then back at Jim. “What do you mean?”

“Oh,” You begin, laughing under your breath. “Just that Kelly has a lot of experience talking with Toby. He was the one who moved her into the annexe, after all. It almost seems like they have a lot in common?” You end it with a question, trying your best to be vague. Jim almost spits out his drink with his laugh, turning to cough into the crook of his arm.

You hear Pam question, “Yeah, why were you moved into the annexe?” Right as Kelly mumbled from beside you, “Not that much in common. Like one thing.” You and Jim meet eyes, trying to keep the humour from your faces.

The rest of the night passed in much the same way. You still were unsure about the whole ‘Jim liking you’ bit but found yourself pleasantly hopeful. And it seemed like- if that was true- maybe Jim was trying to get back at Kelly by teasing her about liking Pam. You began to wonder if that was his plan all along, showing up with Pam randomly. Honestly, whether this was a double date or just a hang-out with friends, you found yourself enjoying the time immensely. But the night was wearing thin, and all four of you had work in the morning.

As you and Pam were helping each other out of the booths, making sure she hadn’t forgotten her purse, Jim and Kelly had run off to pay the bill. You glanced over at Jim- probably with a longing look since you can’t exactly help it, being slightly inebriated- and watched him lean in close to Kelly as they began whispering back and forth.

“He’s a good guy, y’know.” You look back over to Pam, eyes widening. “I don’t know you well enough yet to know your thoughts on him, but he is a good guy. And he deserves the world.” You chuckle softly, nodding.

“Yeah,” You say breathlessly, looking back over to him. He glanced up at the same time, and you can’t help the smile crossing your face. “I think so too.”

“Then tell him,” Pam insists, and you look back down to her. “He deserves to know that. He thinks he’s not worth your time, apparently.”

“That’s ridiculous-”

“What’s ridiculous?” Jim asks as the other two rejoin you and Pam. Pam smiles brightly leaning over to take Kelly’s arm.

“That you have to drive all the way across town just to drop me off, Jim!”

“Actually, we were just talking about that,” Kelly mumbles, and you smile watching her attempt to hold eye contact with Pam unsuccessfully. “If it’s okay with you, then maybe I could take you home? And Jim can take Y/N.”

“Yes!” Pam practically yells out, and you chuckle softly. You look over toward Jim, seeing him already looking your way.

“If that’s alright with you?” He whispers, and you nod immediately.

“Of course it is, Jim.”

“Good,” Jim says, releasing a breath as if with relief.

“Good,” You parrot, reaching forward boldly to take his hand. “Lead on, then.”

Once you and Jim make it to his car, you both wait before getting in to make sure Pam and Kelly are in their car safe and buckled. Once Kelly begins pulling out, Jim turns to you and leans in closer. “I had a fantastic time today.” You laugh, nodding along, leaning against his car and gravitating toward him.

“I did too. ‘Was surprised that Pam showed up, though.”

“Well, Kelly did say it was ‘the office’ going out for drinks. I thought it’d be fine.”

“Well, she didn’t actually mean the office, apparently. She was just trying to get us alone.” You shrug, smirking up at him. His deer-in-headlights look was gone now, for some reason. He seemed bold, leaning closer and taking your hand.

“And if it was? Would that have been fine?” You laugh again, nodding slowly.

“That would’ve been perfect.” His face slowly loses his teasing look, turning serious- but soft.

“Y/N,” Your name is husky in his mouth as he begins leaning closer, and you can smell his cologne in the air. Everything was so much, his smell, his body heat, his honey-brown eyes as he took up your entire vision. “Can I kiss you?”

“Please,” You whisper in return and meet him halfway as your lips crush together. He pulls the hand not holding yours to your face, lightly caressing your cheek throughout the heated kiss, and you grab hold of his hip with your own free hand, pulling him closer. You can feel him moan through the kiss, turning his head to deepen it. This was nothing like you’ve dreamed of- but oh, so much better.

When you two finally part, breathing heavily, he’s pressing you against his car with the length of his body. You both pant as you stare into each other’s eyes, and your grip slowly loosens on his hip. Eventually, he pulls away, clearing his throat with a blush. “Wow,” He whispers, a smile growing as he looks at you bashfully.

“Yeah,” You agree just as quietly, and Jim moves to open the passenger door for you. “Oh, right. Thank you.”

As you sat down in Jim’s car, ready to be driven home, you can’t help but think: ‘Man, I love working for Dunder Mifflin. Even the bad days can turn into the best ones.’

Tag List: @ltnoscara @zombieboyevan @cursedashes

#jim halpert x reader #jim halpert x trans reader #ftm!reader #gay!jim #pam beesly #michael scott #kelly kapoor #bi!kelly #the office toby mentioned #dwight shrute mentioned #drinking in moderation #happy ending #the office #fanfiction

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