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whitaker & robby | good luck babe

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!!!
your therapist called, she said you need some more da pitt on instagram (and a lotta texts)! 📞
part 3/???
More Robby in lingerie!! Read the first part here!!
Jack hasn’t stopped talking about their night with the slip. That poor thing didn’t survive, but those few hours rooted in his head and he frequently brings it up when he’s fucking Robby. Pleading for another, offering to buy it himself.
Lucky for Jack, his birthday is coming up.
Robby is too aware of himself to buy anything in person. So he swipes a catalog from a lingerie store in the mall before one of the employees can acknowledge him. At first, Robby intended on surprising Jack again, but the temptation to see him turn red is too strong. He places the booklet over Jack’s textbook one evening.
“You pick three, and I’ll choose from those.”
Jack looks at him like he’s not real. His face flushes, and eyes shine. Robby can already see the tent forming in his shorts.
“I love you.”
“Mhm.” Robby sits on the opposite end of the couch. “Hurry. I have to order by tomorrow or it won’t be here in time.”
Jack groans and palms at himself the entire time he’s flicking through the book. “Only one?”
“Look at the prices.”
“Fuck. When we start making that doctor money I know exactly what I’m spending my first cheque on.”
He shoves a hand under his waistband and strokes himself.
“That’s rude,” Robby teases. “Thinking about them in front of me.”
“Them?” Jack’s eyebrows pull together.
“The models.”
“Are you crazy? I’m not fucking thinking about them.”
Robby snatches the catalog and drags Jack to the kitchen table. He forces him into a seat and hands him a pen. “Pick three,” Robby commands, sinking down under the table.
If Jack was having trouble thinking before, it’s nothing compared to the struggle of making a decision while Robby sucks him off as he imagines him in the pretty lace and sheer fabric.
In the end, Jack has made his choices and is slumped over boneless from an orgasm. He can’t remember what he picked, but it hardly matters. Robby will look pretty in anything.
When the package arrives, Robby sneaks away to make sure it fits. It’s a pretty pale blue bra and panty set with matching stockings. The bra sits surprisingly well on his flat chest, his dick strains against the panties but otherwise they fit fine so he considers it a win, and the stockings are a little tight around his thighs but he could use the extra support keeping them up.
He folds them neatly back into the box before leaving the bathroom where Jack is waiting outside the door.
“No sneak peek?” He pouts.
“It’s not your birthday yet.” Robby finds a roll of tape and reseals the package. “If you open this, it’ll see the trash before you see it on me.”
Jack whines and manages to work himself up into needing a quick handjob from Robby before heading to his afternoon lab.
On his actual birthday, Jack is so eager for his gift that he’s practically shaking through dinner. When they get home, he stares at Robby expectantly.
“I thought you’d be all over me as soon as the door closed,” Robby jokes.
“Don’t you, ya know…” Jack’s jeans bulge at the zipper. “Need to get changed.”
Robby shakes his head, “No, I don’t think so.”
“Come on.” Jack bounces on the balls of his feet. “I behaved. I didn’t look! And it’s my birthday.”
“Jack,” Robby struggles to contain his laugh. “I’m already wearing it.”
Jack’s mouth slams shut. His eyes darken and he rushes over, shoving Robby’s shirt up past his nipples. “Oh, God,” he moans. He traces his fingers over the fabric. “You’re perfect.”
Robby’s face burns. “Shut up.”
“Why can’t you ever take a compliment? We need to work on that.”
“I- hmm,” the worse escape him as Jack nips and licks along the edge of the bra.
Jack already has a hand down his pants, that won’t do.
“Let go.”
A broken noise shreds through Jack’s throat, “Mikey, c’mon.”
Robby rips himself out of Jack’s hold. He throws his shirt to the floor, kicks off his shoes, and relieves his belt from the loops of his pants. They fall just enough for the top of the panties to poke out. “Strip. Leave your underwear on.”
He leaves for the bedroom, Jack stumbling behind him.
Jack stands helpless in the doorway, boxers stretched taut as Robby peels off the last of his clothing. The sight of the full set creates a wet spot in Jack’s underwear almost immediately.
“Not to say I don’t have faith in you,” Robby says, crawling onto the bed. “But it doesn’t seem like you’re gonna last.”
“I—“ Jack starts to argue, but his dick is taking up too much of his blood for him to think properly. “I’m sorry.”
“Don’t be sorry.” Robby settles in the middle of the mattress on his knees and leans forward, arching his back as low as he can. “Maybe a little appetizer for the birthday boy.”
A pathetic whimper sings from Jack. Robby’s own cock strains against the panties; it’s not often he’s the one calling the shots. Whatever the lingerie is taking from Jack, it’s giving to Robby and he’s getting a little high off it himself.
“Get up here.”
Jack scrambles to obey. He positions himself behind Robby, covered erection teasing Robby’s hole. “Fuck. Are you…?”
“Am I?” Robby glimpses at him from over his shoulder. Jack’s face is impossibly red.
“The— the plug? Are you wearing it?”
Robby juts his hips enough to make the gem catch on Jack’s tip. “We don’t use it often. Figured we should get a return on the investment.”
“You really are perfect.” Jacks hands clasp either side of Robby’s torso, digging his fingers between his ribs.
“Nuh, uh.” Robby bats his hands away. “No touching. That’s for the main course.”
Jack whimpers but listens. “What, what can I do?” He gasps.
“You’re going to rub yourself on me like the desperate dog you are,” Robby commands. “With your boxers on, so you don’t ruin my pretty set.”
Jack’s tongue falls out of his mouth as he nods. “Okay, okay. Now?”
Robby pushes his ass up even higher. “Now.”
Jack’s movements are sloppy at best. His fingers twist in the sheets in an attempt to keep himself steady as he humps against Robby. The scratchy cotton of his boxers is a delicious contrast to the delicate fabric of Robby’s panties. He moans and cries as his cock catches on the plug, rocking it inside Robby, making Robby’s own dick stretch the soft material as far it it’ll allow. He babbles praises about Robby between his thrusts and pulls the sheets up in an attempt to keep his hands off.
It isn’t long before he’s spilling inside his underwear, dragging his hips over Robby’s ass until the last of his release is dripping down his legs.
Robby flips over to admire the wet stain at the front of Jack’s boxers. Jack emits a broken moan at the sight of Robby’s own puddle accumulating on the blue fabric.
“Take those off, and lay down.” Robby says.
The orgasm has made Jack unbalanced, but he manages to slip his underwear to the floor and collapse onto the bed. Legs still shaking.
“Good.” Robby lowers himself to Jack’s crotch. His dick still has a little chub, and is covered in cum. “Very good.” He licks away the mess.
Jack thrashes under him.
“What’s wrong?” Robby asks when he’s finished.
Jack’s arms bulge deliciously from how hard he’s gripping the pillow. His chest rises and falls erratically. “Still can’t touch,” he mutters.
Robby laughs and sits himself on Jack’s lap, grinding the plug down on his hardening cock.
“Okay, birthday boy.” He grabs one of Jack’s hands and places it over a cup of the bra. “You can touch.”
Frat boy!Jack x bookworm!Robby and lingerie
All of Jack’s fraternity brothers think he’s lying about having a girlfriend (he is) because they never see her and when they ask his best friend, Robby (aka the girlfriend), about her he’s always really vague so they think he’s just being a good friend and covering for Jack.
As a joke, one of the guy’s gets Jack a slip dress with lace trim for secret Santa.
“Thanks but I don’t think this’ll fit me.”
“Hopefully it’ll fit your girlfriend,” one of them says.
“We went a little large just to be safe.” The group laughs like it’s one big joke, but Jack gets a bit woozy from all his blood rushing south.
“You know what? I think it will.”
Robby outright refuses to wear it. He thinks this is Jack’s more frat like qualities rearing their ugly head and it’s all a big ploy to make fun of him.
“Mike, I swear,” Jack begs. “I really, really want to see you in it.”
It’s still a resounding no, until Valentine’s Day comes around and Robby is too broke to get a proper gift.
They have dinner in Robby’s apartment, and while Jack finishes up the dishes Robby sneaks away to get changed.
He feels a little ridiculous considering the dress isn’t meant for someone of his stature. But he can’t deny it does fit rather nicely. He likes how the V of the neckline sits across his chest, and the soft fabric creases when he bends.
‘Sexy underwear’ isn’t really something Robby owns, not that Jack’s ever complained, so he throws on his tightest white briefs underneath and takes one last look in the mirror.
Time to find out how serious Jack was.
The second Jack catches a glimpse of Robby his body slams to a halt. The plate he’s holding shatters on the ground, and his freckled face glows red.
“That bad?” Robby jokes. His heart thuds like a drum under the lace.
Jack approaches slowly, as if any sudden movements may scare Robby away. “Oh my God.” His eyes are locked on the slip. “Oh my God.” He trails his fingers delicately over the satin. He drops to his knees in the living room, admiring Robby from below. His hands sneak underneath the slip and cup Robby’s ass. “Oh my fucking God.”
“Anything else you want to say?”
“Thank you.” Jack is breathless and hard as a rock in his jeans. “I love you. I owe you my life.”
“Shut up.” Robby shoves him, but Jack doesn’t move. If anything, he squeezes Robby’s ass even tighter.
“If that’s what you want,” Jack says. “Anything you want, I’ll do it.”
“Anything?” Usually Jack is the one calling the shots. Not that Robby would ever complain about that.
Jack’s nearly drooling on himself. He looks up at Robby, desperate to serve. “Tell me exactly what you want.”
The sun is starting to rise by the time their night is ending. Robby’s been eaten out, sucked off, and fucked in every position they could think of. They’ve come more times than should be humanly possible, and the slip holds all the evidence.
Robby peels it off with a grimace. It’s stained, lace torn, and stitches ripped. “I’ll have to get a new one,” he yawns.
Jack perks up.
“No,” Robby pushes him down. “Not again. I can’t. Go to sleep.”
Jack settles back down. “Maybe a bra and panties,” he murmurs against Robby’s chest.
“We’ll see.”
—
(The slip for anyone interested)

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*Taps mic* is this thing still on?
First of all, happy Pride month🏳️🌈🏳️⚧️❤️ Secondly, I’m so sorry for the sudden hiatus😭 I hit such a major art block after the Pitt ended, but towards the later half of may I’ve been getting through it! During that time I’ve been working on something that I’ve put off for too long. I now officially have an acggoods store where you can buy official prints of my work!! 🥳🥳 I plan on making more stuff like stickers or charms, but for now I’ve got some prints on there. :)
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walk with me here... what if robby and jack knew each other and hooked up way back in med school, then found their way back to each other twenty years later ಥ‿ಥ
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I think the deep misunderstanding from the fandom of robby's unconscious bias towards men, and *certain* fandom groups (at times, deliberate) mischaracterisation of it to paint it as intentionally malicious and overt misogyny, is genuinely one of the things I'm saddest about after season 2.
you've taken a very carefully written character- shown to be deeply, deeply good, and deeply relatable to the medical community, and based your entire view of him on an unconscious element of his personality, instead of accepting that good people have flaws. robby's bias (and it's storyline in s1) is meant to be a thing where you go "oh yes, even very competent, very kind men will have this bias often, due to the structure of society. he's written this way because he's realistic. his bias isn't good, but it doesn't de facto make him a bad person."
it's *not* meant to be something that you cling to to discredit his failing mental health, his overt and intentional goodness and his care for others. it's *not* meant to be something that you hunt through every scene looking for- because it's not there in every scene, or even whole batches of episodes. it doesn't inform every choice he makes and it's not present every time he talks to women- it's not even present *most* of the time. you're *not* supposed to hate him.
it's meant to be an occasional callback to the realities of society and how that impacts the behaviour of people who are (as far as they've thought about it) considering themselves feminist. because robby most likely *does* consider himself this way. he absolutely believes in equality and feminism, and he will stick up for women when he sees they're treated poorly (eg, the scene with the male paramedics). he just also doesn't notice the underlying bias he acts on at times.
the inclusion of his bias is meant to do the same thing as every other bias shown in the show that good characters have. mckays unconscious weight bias, langdons gender bias, ogilvies bias against drug users... all there to show good people carry these things, that no one is perfect, and we should look at our actions towards others.
the fandoms reaction to robbys bias being to wish for his characters death, rather than to understand the intended use as a realistic flaw, is frankly appalling. I will always mourn the interesting, nuanced conversations we *could* have had.
they worked tf out of him

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dennis is basically a service dog when robby has a panic attack. he sees it coming from a mile away, notices the tension in robby's shoulders, how he starts to snap at staff, a hand going to the back of his head and petting or rubbing, self-soothing. desperate to keep it together.
he's quick to slip his fingers into robby's and ignore the older man's protests, dragging him into a quiet room, sitting him down. he curls himself into robby's lap, soft and warm and weighted, grounding and safe. dennis guides robby's hand to his soft curls, and slumps against him, breathing purposefully slow so robby will unconciously start to match it.
and they stay there, for a few minutes. robby's hand loses its tremor as he pets over dennis's hair, his body slowly relaxing as the warmth of dennis seeps into him. robby stops petting for a moment to slide his arms fully around dennis's waist, hugging him close, letting out a shuddering sigh as his face buries in blond curls. he takes slow, deep breaths of dennis's gentle scent, cradling his boy close.
once robby is fully calmed, dennis asks a careful better? and robby hums, drops a kiss to the top of his head. mumbles better, whispers I love you.
she thinks she is so cool because her eyes match her hat
after getting together with robby, dennis is trying way more different foods than he ever has in his life. robby's getting them a new cuisine to try every week, and dennis likes almost all of them. he doesn't like the sushi though- he screws up his face and takes long drinks of water afterwards. upon being asked if he didn't like it, dennis responds,
"not really, it's just like apples, making your mouth all itchy and tingly, and it burns a bit. I don't get why people like it."
and robby's like. oh fuck. my boyfriend is allergic to fish AND apples, and goodness knows what else, and he hasn't even realised.
dennis is surprised to be practically frogmarched to an allergy test the next day by a very anxious robby- he keeps telling the older that he's fine and this is an overreaction, but robby doesn't budge. he *needs* to know how to keep dennis safe.
in the end, it turns out dennis has an allergy to what is suspected to be all seafood, plus the apples. despite them being fairly manageable allergies, and only impacting dennis if he actually ate the food in question, robby goes fully protective over it.
in the supermarket later, he steers dennis away from the seafood aisle and the fish counter, practically dragging his boy in the opposite direction to where his dennis would be "safe". the younger is baffled (and pretty endeared somehow).
"robby, it won't hurt me to be near it, you know? nothing will happen unless I eat it, or maybe lick it or something."
"I don't care, mouse. let me keep you safe. I already accidentally fed you something you have a goddamn allergy for- now I know about it, I can keep you healthy. please, mousey. it scares me."
dennis let robby take the lead after that, blushing at robby's adamance to protect him. it was quite nice, to have someone who cared enough to adapt for him..
these we’re supposed to just be doodles…

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A fresh memory
I’m quite privy to the concept of Robby being well versed in his bisexuality and very comfortable with it.
Maybe he dated men casually in med school, or undergrad, or even some time before that. Had a couple serious relationships with men, even. It’s just that his most recent relationships and those tied to his current life were with women.
Naturally, everyone assumes that he’s straight. And it’s not like he gets the chance to mention it often. So Robby’s heterosexuality goes uncontested until one shift when an old fling shows up in the ER.
A patient, maybe a touch younger than him with bright eyes and a contagious smile who just so happens to be male. He’s immediately a bit embarrassed when Robby shows up, staring at him with wide eyes and a slack jaw in awkward silence for long enough everyone in the room also stills. He grumbles something about how this wasn’t how he’d wanted their reunion to go if it had to happen. Robby just laughs.
They also have ridiculous sexual tension.
Like it’s really, really bad.
Lingering looks, teasing conversation, “never thought I’d see your ugly mug again.” Robby’d say, and the guy would just giggle like it was genuinely the funniest thing he’s ever heard and shrug. Robby even reserves some of his very limited time to hover and strangely micromanage poor Dennis who’s “One of their most trusted physicians, he’ll take good care of you.” And everyone is horribly confused about it all.
When Jack comes in for his shift he’d laugh loud and short and clap the guy on the back. Talking about how he hasn’t, “seen you since Robby fumbled” and it all makes sense.
And, naturally, Dennis is spiraling the entire time. He’s not sure if he should be ecstatic that Robby is seemingly queer in some way. Jealous over their very blatant flirtatious behavior that he hasn’t been subjected to since Noelle. Nervous about it all, or something in between.
Maybe the worst part is that Dennis just can’t hate the guy. He’s sweet, talks to Dennis respectfully, cracks jokes, and says thank you for things he definitely doesn’t have to.
It probably all culminates when Robby comes back through again, squeezing Dennis’s shoulder and raising a brow down at him as he stitches up the guys arm. They talk a little bit before Robby’s called to action, and Dennis probably lets his gaze linger just a tad too long as Robby walks off.
“You like him a lot. Huh?” The man asks, smiling knowingly at Dennis who snaps to attention with embarrassment. Dennis huffs, tipping his head to the side and offering a nervous half smirk.
“Iiiiiii— don’t know what you mean.” He says, chuckling nervously. His gulp is audible as he ties off a suture and moves on to the next. Thinning his lips. The guy just huffs, looking off to the side with a smile. “I don’t blame you, Y’know,” he says, wiggling his eyebrows. “You should have seen him with an ear piercing. The silver ring was always my favorite.”
Dennis sputters, nearly dropping his needle driver.
I’m procrastinating working on my fic, and this is the second idea I’ve had today that I wanted to write on but not had time to make a full oneshot about. If people like this, though. I wouldn’t mind to write it. Wink. (I wrote this in like ten minutes, sorry if it’s a little incoherent or dumb.)
Edit: I’m writing it. I’ll update when it’s done/post it! Should be within the next day or two ;) I’m already about halfway through with the base text