Boldly_Undecided
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birds & bees, or: how dennis whitaker learned to stop fearing sex and love sleeping with his boss by catjohnny
Fandoms: The Pitt (TV)
17 Dec 2025
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Summary
“It's embarrassing.”
Robby glanced over. Whitaker was still facing the window, his hands twisted in the hem of his sweatshirt.
“If it’s got you this worked up, it must be important. I won't judge.”
Whitaker sighed. “I…I started dating someone. A guy. I met him on a dating app, and we’ve been together about a month.”
Robby hummed in acknowledgement. He didn't speak yet, waiting for Whitaker to continue.
“The problem,” Whitaker muttered, “is that he’s…my first boyfriend. I'm 27 years old, and I've never kissed anyone before, let alone had sex. I've avoided the sex part this far—using work and being tired as excuses—but I'm seeing him this weekend and I can't…I know I can’t hold it off forever.”
Whitaker is a virgin. Robby has a hard time saying no to his favorite resident. When Whitaker asks for help with his problem, what else is there for Robby to do?
Bookmarked by Boldly_Undecided
24 Jan 2026
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Jack is wearing nothing but the new watch. Sleek and shiny and expensive, sitting perfect against his wrist, glancing off the lamplight every time Jack looks at it. The sight of that watch is going to make his cock fill from now on whenever he checks the time, if this thorough dicking is any indication.
“You’re like—like my sugar daddy or something,” Jack breathes out around a laugh, and he’s not expecting the way Robby moans from deep in his gut. He’s coming inside only a few short seconds later, and Jack’s moaning in surprise and arousal.
...This might be a thing now.
Bookmarked by Boldly_Undecided
19 Jan 2026
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we could be bigger and brighter than space by wishingonalightningbolt
Fandoms: Our Flag Means Death (TV)
06 Jan 2023
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Her text from Ben tells her where to go and when to be there. It’s a nice hotel this time, and the text also tells her: Woman in her mid-forties. Liked your picture, but seemed skittish. Don’t scare her off.
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Izzy expects that her last year before retirement will be unremarkable. She'll stay focused, won't draw Ben's attention, and soon have enough money saved that she can book a flight to Ed and never look back.
Things get interesting when she meets Stede.
Bookmarked by Boldly_Undecided
24 Dec 2025
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Summary
Five times Jack catches Robby and Dennis having sex, and one time he joins them.
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Jack’s frozen like a buck in front of an oncoming pair of LEDs. It’s like he’s in a trance, hypnotized by the way the yellow overhead light is shining along the dips and hollows of Robby’s biceps. Jack watches his Adam’s apple bob as he swallows. Traces the line of his throat to the gold chain and star of David tangling in the wet mat of chest hair.
He knew Robby was a thicker guy. He’s built like a fucking barrel and he’s been tossing patients around on stretchers for longer than Jack has. He just never pictured…this.
This is what Michael Robinavitch looks like in the privacy of his own bedroom. It’s—intense and weird and the most embarrassing thing that’s ever happened to Jack, which is saying something because he’s lived through a fucking lot.
Bookmarked by Boldly_Undecided
17 Dec 2025
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Summary
One night, shortly before Michael's 55th birthday, he'd carded his hand through Jack's hair and said, "well, if you're really asking, I suppose there is this one thing, but. I want this stated with the full caveat that this is for informational purposes only, got it?"
And that was how Jack Abbot had come to learn that for as long as they had known each other, Michael Robinavitch had wanted, for lack of better terms, a train run on him.
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the free use bottom Robby fic we all need
Bookmarked by Boldly_Undecided
27 Nov 2025