if i were at folsom prison and johnny cash showed up and sang a song about how much it sucks to be in folsom prison i'd be like yeah johnny cash tell me about it đ
Leonard pretends he is not sentimental about aftercare, which is exactly how you know he is. He acts as if the entire thing is merely practical: water on the bedside table, a towel tossed in your direction, a dry comment about how you look like youâve âsurvived a hostile peer review.â But his hand lingers at the small of your back. His voice softens when he asks if youâre sore. He watches your face too carefully for a man claiming indifference.
He is not soft in the obvious way. He will not coo over you like some adoring fool. Leonardâs tenderness is quieter, sharper, almost annoyed with itself. He pulls the blanket over your bare shoulder, brushes your hair out of your face, and mutters, âDonât look so surprised. Iâm not an animal.â
Then, after a pause, in that dry, devastating voice:
âNot entirely.â
B â Body Part
Yours? Your eyes.
Leonard loves watching the exact moment arrogance becomes uncertainty. He likes your eyes when youâre challenging him, when you think you have the upper hand, when youâre furious enough to argue and clever enough to almost win. But he loves them most when youâre undone beneath him, wide and wet and startled, as if your body has betrayed every intellectual defense you tried to build.
âAh,â he murmurs, thumb brushing your cheek. âThere you are. Finally honest.â
His? His mouth.
Cruel, clever, elegant, lethal. Leonardâs mouth is his primary weapon long before it becomes anything sensual. He can shred confidence with one sentence, praise you with another, and make both feel equally intimate. His lips are thin, expressive, often curled into that sarcastic almost-smile that makes you want to slap him or kiss him.
Unfortunately, he knows this.
C â Cum
Leonard is deeply, privately possessive about finishing inside you. He frames it as indulgence, inevitability, biology, anything except attachmentâbut there is always something darker beneath his composure when he does it. He likes the intimacy of it. The finality. The way your body tightens around him afterward, as if trying to keep him there.
He becomes especially insufferable if you beg for it.
âOh, now you want commitment?â he murmurs against your mouth, hips grinding deep, voice rougher than usual. âHow charming. A little late in the semester for that, donât you think?â
But he gives it to you.
And afterward, when youâre trembling and furious at how smug he looks, he kisses your temple and says, âExcellent. Full marks.â
D â Dirty Talk
Devastating.
Leonard does not waste words, which makes every filthy thing he says feel deliberate. He speaks as if he is marking up a manuscript: precise, observant, merciless. He notices every reaction and turns it into evidence.
âYouâre very loud for someone who claimed not to care.â
âCareful. That sounded almost sincere.â
âIs this your argument, then? Because I admit, itâs becoming persuasive.â
âLook at you. Finally producing something worth reading.â
He is worst when praising you, because his praise is so rare that it lands like a blow.
âThatâs it. Good girl. See? You can follow instructions when properly motivated.â
E â Experience
Extensive, complicated, and ethically disastrous.
Leonard has lived too long, drunk too much, travelled too far, and disappointed too many people to be inexperienced. He knows bodies with the same cynical accuracy he knows writers. He understands insecurity. Vanity. Hunger. The way people pretend not to want approval until theyâre shaking for it.
He is not romantic in bed, at least not at first. He is analytical. Patient. Slightly cruel. He reads you too well and makes no effort to be polite about it.
The problem is that he is rarely wrong.
F â Favorite Position
You bent over his desk.
It is far too obvious, which irritates him, but Leonard cannot deny the appeal. Your notes scattered beneath your palms, pages creasing under your fingers, his hand at the back of your neck while he leans over you and speaks directly into your ear.
âStill think that paragraph works?â he asks, voice low and infuriatingly calm.
You can barely answer because he is pressed against you from behind, white hair falling slightly out of place, his hooked nose brushing your temple, his hips moving with slow, punishing control.
âUse your words,â he murmurs. âYouâre supposed to be a writer.â
G â Groaning
Rare, low, and deeply inconvenient.
Leonard is not a loud man. He prefers control, and noise suggests surrender, which he finds vulgar in theory and irresistible in practice. Most of his pleasure comes through clipped breaths, rough exhales, murmured curses, and the occasional dark laugh against your skin.
But when you catch him off guardâwhen you clench around him unexpectedly, when your mouth finds the sensitive place beneath his jaw, when your nails drag hard down his backâhe groans from somewhere deep in his chest.
It is not elegant.
It is not polished.
And he hates how much you love it.
H â Hair
White, thick, usually controlled with the sort of careless precision that clearly took effort. During the day, it gives him a severe, professorial elegance. After sex, it becomes deliciously disordered, falling over his forehead in a way that makes him look less like a ruthless literary tyrant and more like a man who has been thoroughly compromised.
He does not like you touching it too casually.
He absolutely likes when you tug it at the right moment.
The first time you do, his hazel eyes flash with outrage and arousal at once.
âCareful,â he says, voice rough. âIâm not one of your bad metaphors to be handled carelessly.â
Pubic hair? Mature, white and silver, neatly kept but not vainly overgroomed. Leonard is too self-possessed to look careless, but too old and too cynical to pretend he is twenty-five. He looks like a man, not an advertisement, and carries that with almost arrogant ease.
I â Intimacy
Difficult.
Leonard can fuck with frightening confidence. He can seduce, tease, praise, humiliate, unravel. But intimacy unsettles him because intimacy requires honesty, and honesty is far less controllable than desire.
He is most intimate when he thinks you are not noticing.
His hand resting over your hip after sex.
His thumb moving slowly along your wrist.
His mouth brushing your shoulder while he pretends to read.
The way he remembers exactly how you take your coffee but mocks you for it anyway.
He will not say, âI need you.â
He will say, âYouâre intolerable when absent,â and expect you to understand.
J â Jacking Off
More often than he admits.
Leonard has too much pride to confess to loneliness, but not enough discipline to avoid indulging it. He touches himself late at night, usually after drinking, usually after rereading something you wrote and becoming angry at how much potential you have. He hates when desire gets tangled with admiration. It makes him feel vulnerable, which makes him meaner the next day.
He thinks about your mouth first.
Then your eyes.
Then the way you look when youâre trying not to beg.
Afterward, he sits in silence, annoyed with himself, and mutters, âPathetic,â though whether he means himself or the human condition is unclear.
K â Kinks
- Praise kink. Not receiving itâgiving it. Leonard knows exactly how starved you are for his approval, and he uses that knowledge ruthlessly.
- Intellectual dominance. He likes verbal sparring that turns physical.
- Humiliation, but refined. Less crude degradation, more surgical observation.
- Jealousy. He enjoys provoking it, though he pretends to find it tedious.
- Oral fixation. He is fascinated by mouths, especially when they stop arguing and start begging.
- Clothing. Pencil skirts, undone blouses, his shirts on your body, bare skin against tweed and linen.
- Voice kink. He knows exactly what that baritone does.
L â Location
His office.
Not because it is comfortable. It is not. It is cluttered, book-lined, intimidating, and full of evidence that Leonard has built an entire life out of judgment. That is precisely the point.
He likes you surrounded by manuscripts, criticism, half-empty glasses, expensive pens, and the smell of paper and old smoke. He likes the wrongness of it. That his reputation, your composure, and several academic boundaries are all hanging by a thread.
Other favorites include hotel rooms after readings, narrow hallways after everyone else has left, and his apartment when rain presses against the windows and neither of you says the thing you both came there to do.
M â Marking
Possessive, but discreet.
Leonard does not leave careless marks. He leaves deliberate ones. A bruise high on the thigh. Fingerprints at the waist. A bite just low enough to be hidden beneath a collar. He likes the idea that only you know they are there. That you will sit through class, dinner, conversation, some tedious literary party, and feel the quiet ache of him beneath your clothes.
If you mark him back, he pretends to be irritated.
âJuvenile,â he mutters, inspecting the scratch on his shoulder.
But he does not actually sound displeased.
N â Nudes
Dangerous territory.
Leonard would never ask crudely. He would make some dry, infuriating remark about visual evidence, then watch your reaction over the rim of a glass. But if you sent him something private, something tasteful but unmistakably obscene, he would go very still.
He would study it like a manuscript he was not ready to admit moved him.
Not smiling. Not laughing.
Just looking.
Later, he would tell you, âCompositionally, it has flaws.â
Then his voice would drop.
âBut Iâve found myself returning to it.â
O â Oral
Giving? Devastatingly thorough.
Leonard approaches oral sex like an argument he fully intends to win. He is patient, observant, and mercilessly attentive. He watches your body for every involuntary response, adjusting with the precision of a man who has spent his life noticing weaknesses. His mouth is warm, clever, and cruelly unhurried.
He praises you between kisses, which is worse.
âThere. Thatâs the sound I wanted.â
Receiving? He likes it more than he lets on. He especially likes your mouth because it gives him the rare pleasure of seeing you temporarily unable to argue. His hand rests in your hair, not forcing, just guiding.
âMuch better,â he murmurs, breath uneven. âYour strongest work so far.â
P â Pace
Controlled until it is not.
Leonard enjoys escalation. He likes tension. He likes making you wait until impatience ruins your dignity. He will kiss you slowly for what feels like forever, touch everywhere except where you want him, and deliver increasingly cruel little comments until you are flushed and furious.
When his control breaks, it breaks sharply.
Suddenly his mouth is on yours, his hands are under your clothes, and his voice is no longer quite so smooth.
âEnough,â he mutters, pinning you against the nearest surface. âIâm bored of restraint.â
Q â Quickies
He pretends to dislike them.
âAdolescent,â he says.
âUndignified.â
âProof that civilisation is collapsing.â
Then he locks the office door.
Leonardâs quickies are not romantic. They are tense, breathless, and edged with irritation, as if he resents how badly he wants you. They happen after arguments, after you impress him, after someone else flirts with you, after he says something cruel and immediately regrets it but is too emotionally constipated to apologise like a normal man.
So he drags you close instead.
R â Risk
High in theory, controlled in practice.
Leonard likes risk when it sharpens the moment: a locked door, voices down the hall, your hand on his thigh beneath a table, his fingers brushing your wrist during a critique as if nothing is happening. He enjoys watching you try to maintain composure.
But he is not stupid.
True exposure would irritate him. Scandal bores him unless he is the one writing about it. He prefers danger contained, privacy maintained, and plausible deniability preserved.
âDiscretion,â he murmurs, mouth against your ear, âis the last refuge of intelligent sinners.â
S â Stamina
Excellent, but not in a showy way.
Leonard is not trying to prove he is young. He knows he is not. That confidence is part of the appeal. He is patient, deliberate, and skilled enough to ruin you without rushing. He can spend an absurd amount of time teasing, pausing, talking, touching, studying your reactions until youâre trembling with frustration.
He does not need frantic athleticism.
He has timing.
And he uses it like a weapon.
T â Toys
He prefers improvised elegance.
- His tie around your wrists.
- A fountain pen dragged cold along your thigh.
- A leather belt, not necessarily used harshly, but placed where you can see it.
- A chair.
- A desk.
- A marked-up manuscript beneath your palms.
He is not against toys, exactly, but anything too obvious makes him sneer. Leonard likes objects with context. Things that already belong to his world, repurposed into something private and obscene.
U â Unfair
Unbearably.
Leonard is unfair because he notices everything. The way your breath changes when he lowers his voice. The words that make you defensive. The praise that makes you melt. The criticism that makes you furious enough to kiss him.
He will absolutely exploit every one of those discoveries.
âYouâre angry,â he observes calmly, fingers sliding beneath your chin.
âIâm not.â
âYou are. Itâs making you sloppy.â
âShut up.â
His smile barely appears.
âMake me.â
V â Volume
Low.
Leonard likes quiet because quiet makes every sound more revealing. Breath. Skin. Fabric. A stifled moan. Your hand slapping over your own mouth because someone might hear. He enjoys secrecy far too much.
He himself is restrainedâuntil he is close. Then his voice roughens, his curses become less polished, and the sarcasm falls away into something much more honest.
âGod,â he breathes, gripping you harder. âYouâre going to be the death of my better judgment.â
W â Wildest Fantasy
Not merely sex.
Surrender.
Leonardâs wildest fantasy is not about a position or a place. It is about someone seeing him completelyâthe arrogance, the failure, the bitterness, the talent, the lonelinessâand still staying. It terrifies him, which is why he buries it beneath cruelty and cleverness.
But physically?
A long weekend away from everyone. No students. No literary parties. No reputations. Just rain, books, alcohol, arguments, sex, silence, and you wearing one of his shirts while reading something he wrote years ago.
He would mock you for it.
Then watch you from the doorway like a man quietly starving.
X â X-Ray
Mature, thick, and heavy in the hand.
Not pretty in a delicate way. Substantial. Masculine. Slight curve, flushed dark at the head when aroused, with that startling physicality made more intense by how cerebral he usually seems. Leonard spends so much time as voice, intellect, judgment, and ego that seeing him hard feels almost indecently revealing.
The first time you stare too long, he arches one brow.
âYes,â he says dryly. âIt does have narrative weight.â
Y â Yearning
Hidden badly.
Leonard yearns through criticism. Through sarcasm. Through the extra glass poured without asking. Through the book left on your chair because he âthought you might benefit from reading something competent for once.â Through the way his gaze follows you when he thinks you are not looking.
He is deeply cynical about love because he believes wanting makes people stupid.
Unfortunately, he wants.
This makes him furious.
Z â ZZZ
Leonard sleeps like a man who has spent decades arguing with his own mind and finally lost. Once he is truly asleep, the sharpness leaves his face. His white hair falls messily across his forehead. His mouth softens. His arm ends up around your waist with unconscious possessiveness, despite the fact that he would absolutely deny doing it on purpose.
If you try to leave the bed too early, his hand tightens automatically.
âDonât,â he mutters, voice rough with sleep.
You pause.
His eyes remain closed.
Then, after a beat, quieter:
âI havenât finished ignoring you yet.â
Bonus:
WW â Writing
This is how Leonard realizes he loves you.
Not through some dramatic confession. Not through jealousy, not through sex, not even through the strange, quiet ache he feels when you leave his apartment and the room becomes offensively empty afterward.
He realizes it while writing.
At first, he tells himself the character is fictional. Obviously fictional. A woman with your sharp mouth, your restless ambition, your irritating habit of pretending not to care when you care so violently it practically enters the room before you do. She appears in one scene as a minor complicationânothing more. A clever line. A pair of hazel-lit eyes narrowed across a table. A hand wrapped around a coffee cup. A laugh at the wrong moment.
Then she stays.
Worse, she improves the pages.
Leonard begins writing her again and again, despite himself. She slips into margins, arguments, doorways, unfinished chapters. She becomes the only character in the manuscript who refuses to obey him. Everyone else bends beneath his control, but she resists. She contradicts him. She makes the prose less dead.
It irritates him profoundly.
For days, he denies the resemblance. He tells himself all writers steal. From life, from weakness, from desire, from whatever unfortunate person has lingered too long in the imagination. He has done it before. He has cannibalised former lovers, enemies, friends, failures. This is no different.
Except it is different.
Because he does not write her cruelly.
That is the first warning.
Leonard can be merciless on the page. He knows how to expose vanity, stupidity, hunger, desperation. He knows how to peel a person down to their least flattering truth and leave them there, shivering under literary light. But with this character, he keeps protecting her. He gives her better lines. He lets her win arguments she has no business winning. He describes the vulnerable tilt of her mouth with such tenderness that, upon rereading it, he goes very still.
Then he deletes the paragraph.
Then he rewrites it worse.
More honest.
That is when he knows.
He sits alone at his desk long after midnight, white hair disheveled, hooked nose shadowed by the desk lamp, one hand resting over the manuscript as if he could physically restrain the truth from rising off the page. The character looks nothing like a confession and exactly like one.
You are in the rhythm of the sentences.
You are in the cruelty he cannot quite bring himself to give her.
You are in the one line he keeps rereading because it sounds less like fiction than surrender.
She made him want to be understood, which was intolerable, because understanding was only another word for being seen too clearly and loved anyway.
Leonard stares at the sentence for a long time.
Then he mutters, âOh, for Christâs sake.â
Because there it is.
Not lust. Not fascination. Not intellectual vanity. Not the old, familiar thrill of wanting someone he should not want.
summary: after seventeen years, it still seems that Harry doesnât quite know all that he thinks he does.
warnings: none, really. fluff. longtime besties. allergic to communication trope stretched over decades. some things get lost in translation but it shall all be resolved in the end.
note: if you were to look at my several other attempts at writing on different apps, youâd know that i am VERY bad at doing things in a timely manner but hot damn will i get things done before the deadline, even if itâs at the absolute last minute. that being said, hereâs my entry for the @pedroscurls PPCU dialogue writing challenge! my prompt was âWait a minute⊠Are you jealous?â not gonna lie â half of this was written while i was on my third dosage of Sudafed, and the other half was completed in a casino parking lot waiting for my sister and her friends to finish their birthday celebrations. and considering this is my first attempt at writing after a 2 year break, please take this with a huge grain of salt and donât look too closely orrrrr you might find many errors. but with that i also hope you enjoy it and itâs worth your time!
wc: 5k
Just another overly-exuberant Castillo function. Glittering glass chandeliers. Extravagant but tasteful floral arrangements at every table and lining the walls. A five-star catering company bustling in and out between patrons as they refilled trays and adjusted platters. Champagne bottles popping every few minutes and flowing into frost-coated flutes. Music, loud and swinging, as guests mingled on the dancefloor, only some actually giving a show of a dance while others laughed and chatted. Guests seated around the round tables as some business deals were finalized over hors dâoveurs and whiskeys, neat please.
Yes. This was the norm for the Castillos. And despite knowing them for the last seventeen years and being invited to more than your fair share of events, seeing the finished product never failed to take your breath away every time you stepped foot in the rented out ballroom on Harryâs arm.
One of the best decisions you could have made while doing undergrad at Columbia was to sit next to Harry Castillo in your Intro to Communication Studies class as a bright-eyed and bushy-tailed freshman. Of course back then you hadnât known youâd picked a seat next to the son of a Fortune 500 company. All you had seen was a boy with a kind face who looked just as nervous as you to be beginning a class entirely focused on public speaking.
You gave him a smile. He returned it. You introduced yourself. He introduced himself. The professor spoke. And suddenly you and Harry were partners for the quarter.
It took a few meetings for the awkwardness and clunkiness of your encounters to wear off. Between meet-ups at the PUB and quiet conversations in Room 103 before and after class, you and Harry got to know each other and gradually became comfortable around each other. You naturally melded well, which was a blessing considering you two would be working together quite often over the course of the next three months. But in getting to know him, you found you had a fair few things in common. He liked to read, you were a fiend for poetry. He enjoyed a quiet night in over bustling clubs, you couldnât recall the last time you went out. He hadnât been able to control the scowl that pinched his face when someone asked if you both wanted to join them on a hike, and you couldnât help but laugh and share your equal disdain for the outdoors.
Best decision you had ever made.
After the public shame ritual that was a speech class, you and Harry ended up staying in touch and becoming close friends in that freshman year at Columbia University. It wasnât until the end of the school year that you learned he was Harry Castillo, son of the co-founders of THE Castillo & Lynch Capital: one of the most successful private equity firms on the East Coast. You would have never guessed that his family was that wealthyâhe was one of the most humble and down-to-earth men youâd met. His temperament was a breath of fresh air from the sea of cocky, alpha-male type business dudebros in the rest of your business classes.
You met his younger brother, Peter, and his parents that summer while visiting over a holiday weekend. It was quite easy to see where Harry got his kindness and softness from: his family were the perfect hosts for your long weekend stay, they were perfectly chatty and seemed truly interested in learning more about you, and even extended an invitation to their Board Members Ball the next night. You tried to politely refuse, truly, but they were as stubborn as they were nice. They would not take no for an answer.
Thatâs how you found yourself in attendance at your very first Castillo function. You had been so awestruck back then that it took a few minutes to recalibrate yourself to be an actual human being rather than a fish gaping for air on land. Harry had awkwardly scratched at the back of his neck at seeing your face, offering a half-assed bashful comment on how his mom didnât know the word âlimitâ when it came to decorations. âWith New York financiers, there really is no such thing as too big.â
Your wide eyes still glittered as you took the scene in. That night, you and Harry and Peter had mostly clung to the sidelines. The three of you were decidedly not business people. Not quite, anyways. You and Harry were in your undergrad pursuing a business degree while Peter was entering his junior year of high school. You three had absolutely no business mingling with businessmen and women. You three did, however, absolutely take advantage of the loose supervision of the free champagne floating around the ballroom on serving trays. You and Harry ended up having to carry Peter home and hide him from their parents as he nursed a tragic hangover that came from too much bubbly in a sixteen-year-old boy.
From then, youâd always been welcomed at the Castillo home. Through college, summer breaks, and even into your first ventures into the ârealâ world with no safety net and only your hard work to aid your navigation of the job hunt. It was only after a few months of failed interviews and fruitless job searches that you accepted a temporary position with Castillo & Lynch. Temporary. Only until you could get your feet under you, only for the purpose of building connections and networking so that you could soon get a job yourself. If the Castillos had it their way, youâd have stayed with them and worked all the way up to Junior Associate within a year. But you were determined to make a name for yourself and build your reputation on your own rather than relying on the already well-established Castillo name â no riding coattails for you.
Unless, of course, it was on Harryâs arm walking into a party you had no business attending; more so for his comfort than yours. In that case⊠all bets were off. You suspected that somewhere along the way it had just become a convincing lie he stuck to in order to guilt you into continuing to join him. While your career was much slower in growth, Harryâs skyrocketed. He wasnât quite a nepo-baby, but he was pretty damn close. He worked hard, explored side ventures, founded start-ups, made his own deals, and was a hell of a businessman on his own, yes. But the Castillo name surely aided him along the way and he soon shot up to the title of Senior Associate within Castillo & Lynch.
And now, here you were, at your umpteenth Castillo function. Another upscale ballroom, another lavish celebration, another half-assed purpose for the whole thing. But hey, seventeen years of these parties had led you to be numb to the extravagance of it all. Rather than a rare occasion and coveted invitation, this was just another opportunity for free booze and a crowd of CEOs and VPs and associates to rub elbows with.
Harry, your unofficial all-but-in-name date for the party, had already mingled in with that specific crowd. Disappointing, but not surprising. He never was one to sit idle and let opportunities pass him by. Somehow after years of attending parties and conferences and weddings together, it seemed that he was just as oblivious to the attraction you felt towards him as the day it began. Not a crush â that was the term you used in university, and childish. No, this was an attraction formed after almost two decades of friendship and close proximity and inside jokes and life â very adult, thank you very much. Probably a good thing that he didnât notice, though. All this time later and you still had absolutely no idea as to what you would say if he even questioned you about it.
You nursed your drink of choice while surveying the floor, trying to mark the first target you would visit of the night. Letâs see⊠TA had been looking into expanding into the Northwest⊠business partners would be a good start⊠Trilogy? That might be a good place to start. And at the very least, it wouldnât hurt to build on networking opportunities. Thereâs Harry with, God, a stunning socialite practically tripping over herself to hold his arm. Well, at least heâll be busy for the next twenty minutes. Here we goâŠ
âŠ
Another highball later and you felt your cheeks heating as you smiled with the representative for the Trilogy Private Equity firm. Randy, his name was. Your unofficial pitch to him on behalf of TA Associates had gone over spectacularly and youâd quickly exchanged business cards. But now you were just talking with the man, and it was nice. He was kind and quick and funny and a good listener. And so so smooth with the subtle, small hints of flirting he sprinkled throughout the conversation. It was almost difficult to determine when he was intentionally flirting and when he was just chatting and thatâs partly what made it so perfect and relaxing. You felt at ease, your shoulders sliding down and your sips of your drink becoming more for fun rather than nerves. You didnât feel like you had to analyze and decode every word he said for a potential flirt or a loaded link back to business. It was just⊠nice.
When your ice cube rattled in the glass emptily, he smiled and offered to go grab a fresh round. You thanked him after giving him your preferred drink and watched as he disappeared into the crowd of suits, your cheeks only slightly aching when you realized you were still smiling.
âHowâs it going over here?â
You damn near jumped out of your skin. Harry leaned against a chair behind you as you turned around, the picture of casual nonchalance, as if he hadnât just scared the shit out of you. You fixed him with a light glare â nothing like the withering stares you reserved for boardrooms and negotiations. âIâll slap you.â He just chuckled and rolled his shoulders before tilting his head expectantly, as if waiting for an answer. You let your posture loosen and released a breath you didnât quite realize you were holding. âFine. He works for a firm out west dealing mainly in healthcare. TA has been trying to expand to the west coast, so I threw out my line.â
Harryâs brows lofted. âWow. I never knew healthcare could be such an⊠engaging topic of conversation.â
His words were light, but you frowned in confusion. âWhat do you mean?â
âNothing. JustâŠâ His gaze dropped for half a second and it seemed like he reverted back to ten years ago before the air of confidence seemed to lift his feet off the ground. âYou seemed to be getting along well over here. You know⊠laughing and smiling.â
You let out a snort and shook your head. âI should hope so. Half of my business deals hinge on conversations like that going well.â
Harry just dropped his head forward even more, as if incredulously. âBeing likable is never something youâve ever had to worry about with work. You know what I mean.â
Again, your forehead wrinkled in a frown as your lips twisted. âWhat? No. Huh? What you mean? What does that mean? What are you trying to say?â
For a moment Harry looked⊠nervous. But it quickly wiped from his face and he straightened up and focused his gaze behind you. âAnd for you a⊠Oh!â You turned. Randy returned with a glass in each hand â his own finger of brandy in one hand and your drink in the other. His eyes flickered between you and Harry before he awkwardly set both drinks on the table on your right in order to extend his hand with a smile. âHi! Iâm Randy. I work for Trilogy in Washington.â
Harry returned the gesture with an easy, lopsided smile and his right hand outstretched. âHarry Castillo, Castillo & Lynch.â
Randyâs eyes widened in the slightest. âCastillo? Wow, itâs so nice to meet you! You⊠You throw a hell of a party.â
Harry chuckled while shaking his hand. âIâm not allowed within a ten-foot radius of event planning, but Iâll be sure to pass the message along. Thank you.â They released their handshake. An almost awkward air fell over your shoulders but it was quickly dashed away as Harry stepped closer to Randy as if to be heard over the music. âSo, she was just telling me that Trilogy specializes in healthcare. Tell me about that.â
Randyâs hands were active as he gave the same sort of company spiel that heâd given you just twenty minutes ago. The drinks heâd brought back sweat on the table. You shifted to grab your drink and brought the straw to your lips, drinking now reverted back to nerves as you watched Harry and Randy go back and forth for a few minutes. They were completely engaged with each other while you had suddenly shifted to be the third-wheel in the conversation. It was as if Randy had completely forgotten you existed.
âSounds like you have a hell of a company,â Harry said with a smile. âListen, Randy, weâre always looking to expand our business partners, especially on the west side.â His hand reached into his suit pocket, and your jaw dropped. No way he was about to⊠âWeâd love to know more.â
Yes. That was absolutely Harry Castilloâs fucking businesscard extended between his fingertips. To Randy. To the company you had just connected with.
âSounds great!â Randy exclaimed as he reached for his own card. âWeâre well-established in the Northwest but weâve been dying to make some East Coast connections.â
Harry took the business card identical to the one in your clutch with a nod. âLook forward to hearing from you.â
You could barely contain your scoff as you turned on your heel and left the vulture to continue preying on hisâno, your target. That absolute prick. The nerve of him. You had never seen anything like that before from Harry. From others, sure. It could be a cutthroat world when networking off the books. The difference between a Fortune 500 company like Castillo & Lynch and a moderately successful company like TA Associates always came down to the connections made between other businesses. You had just talked to Harry about TA wanting to expand west, and now thatâs suddenly thatâs the direction his company is heading too?
You had never seen Harry and Castillo & Lynch being rivals, being that aggressive. Itâs not like you were going around spilling company secrets and agendas willy-nilly, not like you were poking and prodding around for what his companyâs next move would be in order to spoil it. But now it seems like youâd made a huge mistake by sharing your networking with your friend. Your closest friend, your longest friend. And now heâs just⊠betrayed you like that? Like it was nothing? Business as usual? You feel as if you had been taken back ten years to the year of radio silence when Harry abruptly went MIA.
Maybe sitting next to him at Columbia had been the worst decision of your lifeâŠ
âŠ
It took Harry five minutes to realize you had disappeared. Randy was good company as they chatted numbers and logistics and arranged for a future video call between the heads of Castillo & Lynch and Trilogy. By the time they grinned and shook hands one more time, you were long gone.
It took another thirty minutes to realize you were avoiding him.
He finally found you near the coat closet, arms crossed firmly over your chest as you waited in line.
âLeaving so soon?â Harry asked, startling you. You turned to look at him but your eyes quickly narrowed in a glare. âYou know, we used to shut these things down back in the day.â
His attempt to make you even crack a smile failed pathetically. âYeah, well, clearly things change.â
Harry frowned. âWhatâs that supposed to mean?â You rolled your eyes. He had never seen you like this before. Sure heâd known you were a hell of a businesswoman and could startle men enough to believe hell had frozen over with a single look. But Harry had never been on the receiving end of those looks. You turned to the coat clerk but Harry quickly wedged himself between the two of you. âHey, wait. Iâm serious. Whatâs⊠all this?â
You flipped your gaze to the ceiling as if you couldnât believe what was happening â and you really couldnât. How quickly he had changed⊠âHarry.â He only raised his eyebrows, silently begging you to continue. As if he truly had no idea why you were this perturbed. So with a sigh, you folded your arms across your chest once more. âI know for a fucking fact that Castillo & Lynch isnât currently trying to break into the medical equipment field.â
His brows knit together even further, somehow simultaneously looking impossibly soft and ridiculously clueless. God, you could smack him. Or run your hands through his hair. âRight. Weâre⊠not.â
Now you arched your brows almost to your hairline. âYeah. Youâre not.â Harryâs face didnât move an inch. It seemed like he still didnât get it. You threw your hands out in exasperation. âSo why the fuck would you poach a potential business partner right out from under me?â
âPoach?â
âYeah, Harry. Poach. You absolute dickhead.â
âThatâs not⊠I wasnât trying to poach him from you.â
âOh really? Then what the hell was that back there?â
âIâŠâ Harry gaped for a moment as if searching for the words. âI was networking. Making connections with potential future partners. Just like every other person in this ballroom. Donât act like you donât know how it goes.â
Your glare turned to ice as he belittled you. He seemed to realize his mistake as soon as the words left his mouth but he couldnât take them back. âOh, I know how it goes. I also know that youâre my friend, and I trusted you.â
âTrusted?â
âI told you things. I shared what our plans were and who we were trying to connect with. You knew that TA Associates has been trying to broach into the healthcare field for months. And when I tell you that Iâm finally making a connection that would help me with the promotion Iâve been dying for for years⊠You swoop right in and steal the connection I made.â You completely disregarded his attempts to try to butt in or defend his actions, your chest heaving in frustration with every sentence. âI know what kind of world it is, Harry. I know it will always come down to who you know and how strong you can present yourself and your business to partnerships. But I never thought that youâd try to sabotage my progress.â
âI would never try to sabotage you.â He looked offended at the accusation, at your words, at your frustration with him. Hurt flashed across his face. âAnd I never could sabotage you. Youâre a⊠Youâre the best in the boardrooms and in networking Iâve ever seen. You could talk someone out of their wallet before they even realized theyâd given it to you.â Your cheeks burned. What? Now you were the one who felt confused. âAnd you werenât talking business anymore.â
âWhat?â
âYouâd already secured a meeting with Trilogy within⊠five minutes.â
âAnd?â
âAnd you were still talking to him for like twenty more minutes. And you were laughing and touching each other and getting drinks,â Harry rambled.
âSo what? What does that have to do with you suddenly coming in and trying to work them into Castillo & Lynch?â
âI - I didnât like⊠I didnât⊠IâŠâHe flushed and suddenly looked everywhere but you.
And suddenly, it all came crashing into your chest.
âWait a minute⊠Are you jealous?â
Harry chuckled awkwardly as he scratched at the back of his neck. âWh - What? I mean, come onâŠâ
You laughed also, but this one came out cruel and disbelieving. âAre you serious? You tried to wreck my networking because you were jealous? What are you, twelve?â
Harry didnât laugh. He just⊠watched you. You could see his brain processing and malfunctioning behind his eyes. And he looked⊠devastated. As if your words had reached out and physically struck his cheek. You quickly looked down and swallowed hard.
âI wasnât⊠trying toâŠâ He trailed off again before sighing. âI wasnât trying to interfere. I justâŠâ
âWhat were you trying to do then?â You asked, softer this time.
He paused for a long moment before finally speaking again. âI donât know. I donât know what I was trying to do there. I just⊠really didnât like how I felt when I saw he was still talking to you. And you were just laughing with him. I - I donât know.â
His words shook you to your very core. âYou didnât like how you felt⊠watching me be happy?â
âN - No! Thatâs not - Thatâs not what I meant.â
âYou didnât like seeing me laugh with someone else?â He shifted on his feet and bit his cheek. Again, you let out an incredulous snort. âNo. No. You donât get to do that. Not after all these years. Not now.â
âNow?â
âYes, Harry. Now.â You shook your head and raked your fingers through your hair. Everything felt so muddy and flat out complicated now. âDo you have any idea how ridiculous this is? I have been by your side for seventeen years. I have been there for you and stood by you and watched as you shrunk yourself in every room you walked into. Then you disappeared for a year. And you came back taller and richer and more confident.â He froze. âAnd now youâre just⊠expecting everything to be normal now. And the one time â the one time â someone shows an iota of interest in me as a businesswoman and maybe even as a person, you just, you swoop in.â
Harry was quiet for a moment, and he swallowed hard. âYou knew?â
âŠ
You had stayed with his family company for fifteen months before finally landing a job with TA Associates based in Boston. It was in the months following your departure that Harry became⊠distant. Sure, you had moved to a different state and were no longer working for the same business so it was expected that you wouldnât be as close as you were before, but Harry had made the effort of staying in touch those first few weeks. Then it was as if he had suddenly gone off the grid overnight. Calls missed, texts ignored, emails returned with an automated response: âOut of Office â Returning Nov 2017. Please use the link to schedule a phone call or Skype meeting.â You even stopped by his parentâs house on the 4th of July under the impression of spending the holiday with the Castillos as you had for the last seven years. They sympathetically informed you that both Harry and Peter were recovering from emergency surgeries and cancelled the holiday festivities for the year. However, your request to visit and check on them and offer help in any way you could was quickly declined and you were pushed away without fanfare.
To say you were feeling hurt and even the slightest bit petty was an understatement. Medical emergencies were understandable of course. But almost a full year without any acknowledgement of your existence, any attempt to respond, any inkling of a desire to continue your friendship had left a sour taste in your mouth.
So when Harry knocked on your door with a bouquet of flowers one October evening, it should have come as little surprise to him when you shut the door in his face. You were hurt. Maybe you werenât best friends any more, but you thought you were still friendly enough that he could pick up the phone and open some form of communication. A quick phone call. A short abbreviated text. A formal email. A letter. Anything that would give some hint of an explanation of why he was being such a shitty friend. But no â all youâd received was fifty weeks of radio silence and a bunch of carefully arranged flowers.
Only through the locked door did Harry finally give his explanation: there was an emergency health episode and heâd undergone immediate surgery and intensive recovery and therapy lasting eleven months. Peter experienced something similar â not quite the exact same situation and diagnosis â and so his family and the company had been scrambling for the last year. It was a long, scary process, but he had fully recovered. And yes, he saw all the messages youâd sent. They made his day again and again and he wanted to share his gratitude in person as soon as he was cleared. Okay, way to set the guilt trip into motionâŠ
When you opened the door and welcomed him into your apartment, the first thing you noticed was how much taller he was. A year was a long time, sure, and you couldnât confidently say what his exact height was before, but it certainly wasnât this. Now you had to tilt your head back to meet his eyes. He wasnât short by any means before, but you know you for sure didnât have to crane back to make eye contact. Did you bring this up to Harry? Of course not. He just shared heâd been through a traumatic year but he was here now and he wanted to see you and resume your friendship. You really didnât think anything of it â perhaps heâd just gone through a late growth spurt. Not unheard of by any means.
But when you finally did return to the Castillo home in New York for an extended friends and family get together, you noticed Peter was also taller. Significantly so. And one late night internet search spiral later, you formed your theory of what had really happened: Harry and Peter had undergone leg extension surgery. $200,000. Up to a year in recovery. Expensive. Painful. Dangerous. Risk. Unnecessary. So fucking unnecessary. A year of radio silence from the Castillo family for what? A couple of inches?
Of course this was never brought up with either of them. It was only a hunch, after all. A well substantiated hunch with several âcoincidencesâ aligning to point in the direction of that being the truth. But if your hunch was somehow incorrect and you did bring it up with the Castillos, then youâd be the dick. Accusing two wealthy financiers of undergoing a ridiculous cosmetic surgery when in reality theyâd experienced sudden and traumatic medical emergencies, as they said, and hit their final growth spurt as late bloomers.
It always prickled under your skin, though. Especially in how Harry seemed different after being AWOL for a year. Much more confident in rooms with colleagues and business partners and rivals. Arrogant, even. Not cocky, not loud, not abrasive. But almost⊠fully evolved, in a sense. Heâd always been a brilliant businessman. Just the right amount of complimentary, the perfect dosage of ass-kissing and sucking up, always quick on his feet with numbers and offers and counter-offers, charismatic as all hell, persuasive as they come. But before it was as if he second-guessed himself in the room where people were significantly above him. Bashful, shy, self-deprecative. Now, though, now he initiated handshakes and maintained eye contact and clapped shoulders with ease and confidence.
Almost as if those extra inches were intentional and implemented with a purpose. Ten years later and you still didnât know if you were right. But nowâŠ
âŠ
âKnew?â Your brows scrunched in confusion as to what part he's stuck on, but you quickly realized⊠âHarryâŠâ you said softly, almost pitifully. âDid you really think I didn't notice?â
âYou never⊠You never said anything. For all those years you never even hinted that you had an idea.â
You snorted. âI didnât think youâd want someone to call you out on it. But yes, Harry, of course I knew. And of course after that women were throwing themselves at you. But I never tried to sabotage any of that. No matter how muchâŠâ
âHow much you what?â Harry suddenly looked alive. Whereas before he was hunched more like a kicked puppy, now he seemed rejuvenated. Energized. Awake. Alert. Intent. âHow much you what?â
Now it was your turn for your cheeks to flush as you cleared your throat. âItâs⊠not important.â
âI never wanted any of them,â Harry said bluntly, cutting you off. You frowned. âThose⊠women. Who threw themselves at me. I didnât want any of them.â
You swallowed hard. Took a step forward. âWhat did you want then?â
He didnât answer. Couldnât, maybe. âHarryâŠâ His eyes stayed firmly fixed on yours. And they softened so gently that your breath hitched. âWhy didnât you do anything then?â
He shrugged half-heartedly, shaking his head. âI⊠I donât know. I was scared?â He laughed once, humorlessly, as you arched a singular brow. âAnd then too much time passed. And then it felt stupid. And then it felt impossible.â
You arched a singular brow. âSeventeen years is a long time to be scared.â
âI know. And⊠Youâre right. I was acting childish. That was so far from the way I should have gone about that.â He again scratched at the back of his neck and blew his lips. âIâm sorry.â
You paused, mouth quirking slightly. âItâs not okay.â He nodded. âLike, seriously. Please donât ever pull that shit again.â
âUnderstood.â Then his lips twitched. âSo⊠what should I do, hypothetically, if I were to, say⊠feel jealous again? You know, in a non-twelve year old hypothetical way?â
âHow aboutâŠâ You stepped forward and straightened his crooked tie. âNext time⊠you tell me youâre jealous before you start stealing my networking contacts? You know, just to make sure weâre on the same page?â
Harry grinned now. He grasped onto your wrists as they hovered above his tie. Your name fell out of his lips softly. âIâve liked you for a very long time. And Iâd like to stop pretending youâre just a friend to me.â
âYeah?â
âYeah. And Iâd like to take you out to dinner.â
Butterflies surged into your throat and you shivered slightly while holding his gaze. âHarry, Iâd love to.â His entire expression relaxed and his eyes lit up. âAfter you call Randy and withdraw Castillo & Lynchâs invitation to a meeting.â
Would you consider writing a Drabble where Harry is sick with the flu and reader is trying to look after him, but he doesnât want to slow down / rest đ
Stay - A Harry Castillo Drabble
Harry Castillo doesnât get sick often. And when he does, he refuses to call it what it is.
It starts the same way it always does - him pretending nothing is wrong.
The first time you notice, heâs at his desk in his penthouse overlooking New York City, laptop open, half-empty coffee beside him, shoulders slightly too stiff for someone whoâs supposedly âjust tired.â
âYou look awful,â you say from the doorway.
âIâm fine,â he replies instantly. Which is how you know he isnât.
His voice is rougher than usual. Thereâs a box of tissues on the desk that definitely wasnât there yesterday. And heâs blinking a little slower than normal, like even that takes effort he doesnât want to admit to.
âYouâre sick,â you say.
âIâm busy.â
âYouâre sick and busy.â
That earns you a look. Sharp, tired, defensive on instinct. He tries to go back to his screen anyway.
You walk in, take the laptop, and close it.
Harry stares at you like youâve just interrupted the biggest deal he would ever make.
âThat was...â
âUrgent?â you finish. âNo. It wasnât. Youâve replied to the same email three times in different fonts. Youâre done.â
He opens his mouth to argue....but coughs instead.
Deep. Unpleasant. The kind that bends his shoulders forward for a second like his body is reminding him it doesnât care about his schedule.
You soften despite yourself.
âOkay,â you say more gently. âBed.â
âI canât slow down right now.â Itâs not arrogance. Not really. Itâs habit. The belief that if he stops, everything will fall apart.
You step closer and press the back of your hand to his forehead before he can dodge it.
It's warm. Too warm. Your expression changes immediately.
ââŠYouâre burning up baby.â
His jaw tightens like thatâs somehow an inconvenience he can negotiate with.
âItâs subjective.â
âItâs medical.â
âItâs inconvenient.â
That almost makes you laugh, but not quite, just an obvious eye roll will do.
âYouâre going to bed. No excuses.â
âI have calls.â
âYou have a fever.â
âI donât..â
âHarry.â Just his name. Nothing else. Thatâs what finally slows him. Not force. Not argument. Just you.
He exhales through his nose, long and controlled, like heâs still trying to win a debate his body has already lost.
âFive minutes,â he mutters.
âYou always say that.â
Still, he stands. Carefully. Stubbornly. Like rest is something he can schedule between obligations. You know he will never change.
You donât let him go back to the desk. You guide him instead, quiet pressure, steady presence until he finally gives up pretending he isnât exhausted.
In the bedroom, he sits on the edge of the bed like itâs temporary. Like he might be called back at any moment. Like stopping is something he has to justify. But the comfort it gives his body is hard to ignore and you can see him slowly ease into it.
You hand him water and he typically takes it but doesnât drink.
âYouâre not working,â you said firmly.
âIâm thinking.â
âAbout work?â
ââŠYes.â
âNo. Harry you need rest. You are no good to anyone this unwell. You'll make yourself feel worse!â you say softly.
That shuts him down in a different way. Not resistance this time. Just stillness.
He watches you for a moment, eyes heavy but alert in that stubborn, lingering way. He sees the look in your eyes practically begging him to slow down.
âThis is inefficient,â he says quietly. He has to have the final say.
âYouâre welcome.â you joke as you pull some cold and flu tablets out of the side cabinet.
That almost gets something out of him, something close to a laugh but it fades before it fully forms. He lies back anyway in defeat. He knew you were right, he just hated to admit it sometimes.
You pull the blanket up over him, and for once he doesnât stop you. You watch as you see his body fully relax into the duvet.
âYouâre still here,â he says after a moment.
âYeah,â you reply, sitting beside him now, your nails running through his curly hair. âUnfortunately for your productivity system.â
A faint exhale. Softer this time. His eyes stay on you. Just watching, wondering how he got so lucky.
âYou shouldnât be this nice to me,â he murmurs.
âWhy?â
âBecause Iâll get used to it.â
That lands between you heavier than anything else heâs said all night. You had been seeing each other for just over a year now on and off, and neither of you would admit what this relationship was, but you had both fallen for each other hard. You adjust the blanket around him, slower now.
âMaybe you should,â you say.
Something shifts in his expression, small, almost imperceptible. Like he doesnât quite know what to do with that answer.
âIâm not good atâŠâ he starts, then stops.
At needing. At letting go. At being anything other than in control. You already knew what he meant, he didn't need to say it out loud.
âYou donât have to be good at it,â you finish for him gently. âYou just have to let it happen.â
Silence. Then, slowly, his hand finds yours, holding on like itâs the only thing keeping him anchored.
His eyes start to drift closed, but even then he doesnât let go.
âDonât let me sleep through anything important,â he murmurs as he relaxed into your nails catching through his hair.
âI think the only important thing right now is you sleeping,â you whisper back.
Then, quieter than everything else:
ââŠStay."
You stay as his breathing evens out, as the tension finally leaves his face, as the man who runs half the financial world stops trying to hold it together for a few hours.
And for once, Harry Castillo doesnât fight rest.
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