prompt by love_me_how
Harvey takes a sip of his scotch as he gazes at the illuminated Chicago skyline through the floor-to-ceiling window of his hotel room.
It's been almost a week since he rushed out of New York, and the past six days have felt like a blur. He could hardly tell the hours and days apart, having spent most of that time in Jessica's office, where they diligently worked to devise a solid, foolproof plan.
When Jessica called him on Monday evening, he didn't have to think twice. His former mentor was in a tight spot, and he would always drop everything in the blink of an eye to be there for her.
He immediately canceled his plans for the night and spent another three hours at his desk instead, booking the first available flight to Chicago O'Hare and securing accommodation for at least two weeks, with the option to extend his stay as needed.
Before leaving, he first called Luis and then Donna to inform them about the emergency, asking them to cover for him by taking over most of his clients and cases for the foreseeable future. He personally reached out to his most important clients, rescheduled as many appointments as he could, and wrote down all the information Donna needed to handle things during his absence. Then he had Ray drive him home, packed his bags, and set the alarm for 4:20 a.m.
Now it's Sunday evening, and for the first time since his arrival, Harvey has a moment to take a deep breath and consciously enjoy some time in his hotel suite instead of just stumbling in for a few hours of sleep or to continue working.
Of course, there's still plenty to do, but with the first day of trial scheduled for tomorrow morning, there's not much else he can do right now except wait for the outcome to determine their next steps.
So Harvey decides to take advantage of this rare moment of respite and deliberately pushes thoughts of the case aside.
And eventually, his thoughts drift to her. Donna. Or rather their brief chat from a few days ago.
D: Hi. How are things going over there?
H: Making good progress. But it's not the same without you here.
D: Oh come on, I'm sure you can survive without me for a few days! Just don't forget to eat.
H: I'm eating just fine. It's just hard having to do all the work myself.
D: Haha. I miss you, too. Good luck and we'll talk later.
…
He had still been staring at his screen when - "Harvey!"
Jessica's voice snapped him from his thoughts. "Hm?" he tried to sound nonchalant but couldn't help noticing the heat rising to his cheeks.
"What are you so smiley about?"
"Nothing, I … it's just Donna. Checking in on how we're doing."
"Donna, huh?" she gave him a meaningful look.
"What's that supposed to mean?" he asked, genuinely confused.
"Never mind, dumbhead. Pass me the next box."
He hadn't heard much from Donna in the past week. And when he did, it was all business. Their communication was limited to short texts and emails updating each other on recent developments, exchanging important information and instructions. The few times they tried to call each other were either met with voicemail or cut short by clients calling or meetings starting.
And so, that little exchange of silly text messages with her felt refreshing. Normal. And it did make him smile. Only that he didn't realize that until Jessica pointed it out to him.
A faint ache in his chest makes Harvey realize that he truly meant what he had told Donna: it definitely isn't the same without her here.
As much as he tries to push it away, he can't ignore the fact that he is indeed missing her. He misses her laughter, her sharp wit, and the way she can read him like an open book. She became so much more than just his assistant over the years; she became his confidante, his anchor in a world that often felt chaotic. And he never realized how much he actually needed her until … now. Is she missing him just as much?
Before he can delve any deeper into those thoughts, a ping from his cell phone brings him back to reality, announcing that Jessica's driver is waiting downstairs to pick him up for dinner at one of those fancy restaurants she had raved about for days.
.
Two hours later, they are in the middle of dessert and on their second bottle of wine. The atmosphere is much more relaxed and easygoing than it has been all week. They had agreed beforehand not to speak a single word about the case that evening, and Harvey has to admit that this was the best decision.
It feels good to reconnect with his former mentor, reminisce about the good old days, and let her in on the newest gossip at the firm she once ran so passionately. With each glass of wine, their laughter grows louder and more lively. And the alcohol only seems to fuel the intensity of their conversation.
"So, how's Donna?" Jessica asks slyly after the waiter pours them both another refill.
"Donna?" Harvey chokes on his drink, caught off guard by the blunt question. "She's fine, I guess."
"Come on Harvey, don't fool me."
"What?" His brow furrows in confusion. "I haven't spoken to her much, we're just exchanging the essentials. She seems to be rocking the business over there, which I'm more than grateful for."
Jessica rolls her eyes. "That's not what I mean."
"Care to enlighten me?" Harvey asks, defensively lifting his hands off the table.
Jessica leans forward, her eyes burning into him. "When are you finally going to tell her how you feel?"
"Excuse me?"
"Oh please, Harvey. Everyone can see it. You have more than just a soft spot for that woman. She's had you wrapped around her little finger for years. If she hadn't been such an outstanding assistant to you - if you could actually function without her - I would have forced a wedge between your inappropriate workplace flirting and those longing stares you exchanged right from the beginning. But that was then; it was just who you two were, and that's probably why you worked so well as a team. But I can see that things have changed now. The look on your face when you get a text from her? When someone mentions her name? Man, you're down bad."
"Well, you're wrong," Harvey spits out, leaning back in his chair with his arms crossed in front of his chest.
"Am I?"
"Jessica, I'm sorry, but you're completely misinterpreting the situation. Donna and I go way back, we've become great friends over the last decade, and I appreciate her more than she knows. But that's it. We were never supposed to be more - and that's perfectly fine."
"Is it? I mean … it's not for her, apparently."
"What did you just say?"
Jessica sighs. "She's been waiting for you to make a move for years, Harvey. I'm a woman myself, I know the difference between a meaningless flirt and serious, desperate longing. Donna has been trying very hard not to pine over you, and I get it. I really do. But it showed that it became increasingly difficult for her to ignore her feelings. I always felt sorry for her because you're such an emotionally unavailable idiot. But you've grown so much, and I just think that you're finally ready. You just have to let her know."
For a heartbeat, Harvey just stares at her in disbelief. What is she talking about, Donna having feelings for him? This is just ridiculous.
He clears his throat and straightens up in his chair before he speaks.
"With all due respect, Jessica. There's nothing to let her know. And I'd rather end this conversation right now."
"You can keep pretending all you want, but it's obvious that Donna means much more to you than just a friend. And trust me, she feels the same way."
"Check, please!" Harvey calls out to the waiter and with a deep sigh, Jessica finally gives in and changes the subject in an attempt to bring back the light mood they were in before. But the spirit is gone, and soon afterwards they call it a night.
.
That night, Harvey can hardly sleep. Not because of the upcoming trial, but because Jessica's words keep running through his mind in circles.
Her bringing up the topic of Donna made him angry and he immediately went into defense mode. Just like he always does when it comes to his feelings. And especially when it comes to his feelings for her. It's hard enough to face your emotions yourself, but it's even worse when other people try to push you to do so.
But now, in the silence of his dark hotel room, he can't shake off the feeling of unease and realization building up inside him. Jessica was right. He knew it, deep down, even before their conversation tonight. But he couldn't access it. Didn't allow it to grow, didn't allow himself to go there. Refusing to acknowledge or explore the possibility that Donna and him could be more than just coworkers with a complicated history.
He's always known that his feelings for her go far beyond anything else he's ever experienced. And he has a pretty good idea of what they could mean. But facing them head-on means confronting a truth he's been avoiding for so long. Is he truly ready to accept it now? And could Jessica be right about Donna reciprocating those feelings? The thought never even crossed his mind until now.
Tossing and turning, he ponders these thoughts all night and still comes to no conclusion.
When the alarm goes off in the morning, he's already - or still - wide awake, takes an ice-cold shower, and gets ready for a day in court.
.
It's a damn long day. But also a damn good one. And so are the following two days as well. Their strategy seems to be working out, their hard work seems to be paying off.
It's not the end of the trial, but it's a small victory already. They still have at least three more days in court left where they must continue working hard to solidify their arguments, gather necessary documents, and negotiate details before a final verdict can be expected.
Harvey dares to hope that the case will be closed in their favor and that in the best-case scenario, he will be back in New York by the middle of next week.
When he returns to his room late that evening, he feels like celebrating. But, the only person he wants to do that with, isn't there. Once again, he realizes how much he misses Donna, and for the first time, he truly lets himself linger on that thought. And how it's making him feel.
Absence makes the heart grow fonder - Harvey thinks to himself with a wry smile. This is silly. He can no longer fool himself. He knows that there is much more to this. Yes, he's never been without Donna for this long, and maybe he needed it to realize some shit. But over the last couple of days, he came to the irrevocable understanding that these feelings went much deeper and back much further.
The urge to be close to her becomes unbearable and without thinking, he dials her number. He yearns to talk to her for once, and not just exchange stilted, impersonal facts via email and text. He wants to know how she is doing. Needs to hear her voice and pick up on all the subtle nuances in her tone that indicate her true mood. And he wants to hear about all the little details she didn't include in her daily updates.
"Harvey, hey," her voice sounds warm and soft when she picks up her phone, and Harvey smiles involuntarily. Only now does he realize how much he likes the mere sound of her voice, how fond he grew of it over the years, and how it has the ability to give him a sense of peace.
He clears his throat self-consciously before speaking, suddenly unaware of what he even wants to say to her.
"Hey, Donna. Is this a bad time?"
"No, not at all. I just got out of the bathtub, waiting for my Sushi to arrive."
Drawing in a sharp breath, Harvey refuses to elaborate on this thought any further, even though he has a hard time fighting the images that her words immediately plant in his head. Is she doing this on purpose? Being provocative? Or is she just being genuine, oblivious to her suggestive remark?
"Did something happen?" she snaps him from his thoughts far too quickly.
"No. No, nothing happened. In fact, the trial is going very well so far. Better than we expected. We seem to be on the right track. I'm daring to be cautiously optimistic," he tells her proudly.
"Harvey, that's great! I'm so happy to hear that. But don't you think it might still be a bit early for you to say this? What if they still have something up their sleeve?"
Harvey's heart makes a little jump in his chest. This is exactly what he appreciates her for so much - always remaining objective, greatly supporting him but never blindly believing that there are no hidden traps.
"I doubt that. They don't seem to have anything in their hands really. None of their arguments seem valid, and they have hardly any evidence."
"I'm so relieved."
"Me too. But enough about that. How are you doing?"
"I'm good, thanks. It's a hell of a lot of work at the moment, but everything is under control, you don't have to worry. Most of your clients are very understanding of the situation, and Luis is dealing great with the ones that aren't or that need short-term consultation. He's excelling at this, actually."
"I'm glad. I'd kick his ass if he weren't. Even more so if he was being a dick towards you."
"Easy there, tiger," Donna laughs. "I can defend myself."
Harvey snickers, "I know you can."
The awkward silence is interrupted by a distant ringing.
"Oh wait, I think my Sushi just arrived. Was there anything else you wanted to talk about?" Donna announces.
"Nah, that's all. I don't wanna keep you any longer. Enjoy your dinner."
"Thank you, Harvey. Take care. And give me a call whenever you need me, will you?"
"You too Donna, thanks. Talk soon."
Give me a call whenever you need me … her words resound in his head and he feels a strange heaviness in his chest. If only she knew how much he truly needed her.
With a frustrated sigh, he drops his phone on the bed. He would like to keep talking to her, but at the same time, he doesn't even know what exactly he should say to her. Or how he could bring up the topic that's been nagging at him for days. Years, probably.
In an attempt to distract himself, he walks over to the little coffee table and pours himself a glass of scotch before plopping down in the armchair in the corner of the dim-lit room.
He takes a sip and closes his eyes, relishing in the smooth warmth as it slides down his throat, before his thoughts drift back to Donna nonetheless.
Memories come back to life — moments they shared in the office, late-night conversations about life and dreams, and those stolen glances that lingered just for a second too long and that always stirred something deep inside of him.
That night at the bar where she introduced herself to him and swept him off his feet.
The first day of her working for him, turning his whole world upside down.
The banter, the flirting, all innocent and light, just like with so many other attractive women he met. At least that's what he made himself believe back then.
And then … the other time. And how that changed everything. At least for him. Only that he didn't understand what it all meant and what he was supposed to do with his inner turmoil.
He chose the only way he knew at the time and asked her to follow him to Pearson Hardman.
She said yes, and they agreed that they would put their night together out of their minds and never mention it again.
But the truth is, Harvey never did. He couldn't.
No, he never mentioned it again. But he did think about it all the more.
And not just that. He had acted on those thoughts more than once in the past decade - far more times than he could count.
And that's why now it's almost like autopilot when his hand moves to open his fly, where his cock has long been straining against his zipper.
He pushes the fabric of his pants and boxers down, watching as his rock-hard erection stands proudly in his lap, bouncing against his stomach as he shifts in his seat.
He wraps his hand around the base, tentatively at first, and lets out a relieved sigh as he recalls that night, her body writhing beneath him, covered in whipped cream as they lost themselves completely in each other, forgetting space and time.
His thoughts get stuck on the memory of her breasts bouncing when she rode him that night. Her breasts. It's always been her fucking tits that did it for him. Full and round and peaked with the perfect little nipples. He always felt that it was somewhat illicit that he knew what the nipples of his secretary looked like, but it was even more unreal to him that even after all these years he still remembered them so vividly, and saw them in front of his imaginary eyes every time he got even the tiniest glimpse of her cleavage.
Up until today, those goddamn necklines of her dresses are driving him crazy. And those expensive, figure-hugging fabrics that seem to perfectly emphasize each and every curve of her glorious body, teasing him with just a glimpse of what was once fully exposed to him. Some days, his favorite days, those outfits can barely be described as work-appropriate, evoking the wildest fantasies in him.
His cock twitches in his hand at his thoughts and he closes his eyes as he grips it more firmly and starts to move his hand up and down its full length.
Her tits might be his favorite detail, but it isn't by far the only thing he remembers about that night, probably the best night of his life. He remembers the way they found a common rhythm with ease after the excitement subsided a bit and they both allowed themselves to let go completely.
He remembers the way he made her giggle at first, and how those giggles quickly turned into sighs and moans and screams over time, and how he made her come over and over again - on his tongue, around his fingers, and with his cock buried deep inside her.
He's moaning at the memory of how she came now, quickening the pace of his hand on his cock. Back then, he had wanted that night to never end, and he still wishes he could go back in time and tell her to stay and never leave him again.
For fear of those sentimental thoughts destroying the mood, Harvey shifts his thinking back to the amazing sex they had that time, climbing the ladder to his climax quickly.
God, the way she looked up at him when she gagged on his cock, almost making him come way too soon. What he would give to have her kneel between his legs right here and now and do it again. Getting him off in seconds.
He's so far gone already, his tip leaking with precum, and his free hand comes to fondle his balls, releasing some pressure and building it further up just the same.
Sweat breaks out on his forehead and he groans loudly as he remembers the way she whined "Fuck Harvey, I'm gonna cum!" when he took her from behind - and that's it for him. He curses as he feels the point of no return approaching, thick threads of semen spurting from his cock in a high arc, ruining his shirt.
Panting heavily, he pumps himself dry, releasing every last drop from his twitching length with shaking hands.
.
Afterwards, after cleaning himself, he just sits there, staring at the opposite wall. He feels lost and a bit tacky, almost ashamed, just like every time he gets himself off while thinking of Donna. Not because it wasn't good, or because he doesn't want to do it again. No. It's the guilt that weighs heavy on him for disregarding her rule, and for thinking of her like that when she is so much more than just wanking-material, when she's without a doubt the most amazing woman he ever met and when she deserves so much better than this.
It hits him at this very moment, with his pants still creased at his ankles and his dick soft and sticky in his lap, that Jessica was right. He fucking needs to get his shit together and take action. He needs to tell Donna how much she really means to him, that he wants to lie the world to her feet, and that he never wanted anything more than to become the best version of himself for her. Only for her.
He doesn't even know if she feels the same and whether his courage will pay off in the end. If he can believe Jessica's words, then there's at least a hint of hope. And this time, he will not let the opportunity pass. Right here and now, he forms a plan.
.
"Good to have you back, hotshot."
The sound of Donna's voice startles him, making his heart pound faster. He looks up from the email he was just typing, taking her in.
She's casually leaning against the doorframe of his office, smiling brightly at him. She looks absolutely stunning in that black, long-sleeved dress, her red curls draped over one shoulder, exposing the sparkling earrings he once gave her for her birthday. Her legs seem to go on for days, perfectly complemented by pink heels.
When their eyes meet, he swears there's heat rising to his cheeks. What is he? Twelve years old and having a crush on his classmate?
"Good to be back, Donna" he retorts nonchalantly, unaware of his foot tapping nervously.
"Want me to run you through the list I made?" Donna asks, waving the folder in her hand.
"Yeah, that'd be great. Thanks."
She spends an hour updating him on all his clients and urgent matters that require immediate attention. While Harvey has a hard time focusing, he doesn't miss the sparkle in her eyes and the way she sits unusually close, allowing a hint of her intoxicating perfume to envelop him.
As their conversation winds down and she gathers her things, a moment of silence hangs in the air. She's about to leave in the direction of her cubicle when she turns around to face him once more, a playful smile dancing on her lips.
"Oh, and thank you for the flowers by the way."
Harvey smiles sheepishly at her, starting to form a reply. "How did you … ?"
The look on her face makes it unnecessary for him to finish the sentence. She's Donna. Of course she knew they were from him.
"You're welcome," he simply states instead.
As she turns to leave his office for good, he calls after her.
"Hey Donna?"
She looks at him expectantly. "Yes, Harvey?"
"May I … take you on a date sometime this week?"