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“Would you…would you be open to letting me try? Try, uh, fucking you, I mean.” He bites his lip; Robby can tell how nervous he is. He smiles and reaches out to rub Dennis’s knee over the blanket.
“I say this every time, baby. I'd try anything with you. You wanna fuck me? Hell, I'll order a douche on Amazon right now.”
Dennis giggles, ducking his head down, but Robby can see the relief washing over him. “It doesn’t have to be, like, right now,” he says. He takes Robby’s hand and laces their fingers together. “Just something I've been thinking about. Wanted to see if you’d be up for it.”
Even after all their lessons and four months of actually dating, there are still things Dennis wants to learn. Robby is always ready to teach, even if it means being vulnerable for a change.
A sequel to "birds & bees, or: how dennis whitaker learned to stop fearing sex and love sleeping with his boss" for day 2 of Trans Pitt Week - "teach me"
Series
- Part 2 of sex ed with michael robinavitch, md
- Language:
- English
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- 1/1
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Bookmarked by LittleSquidScribbles
29 May 2026
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It started with an innocent question.
“What do you think about Jack?”
Bookmarked by LittleSquidScribbles
28 May 2026
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“Hmmm,” Santos said, tapping her chin dramatically. “Who do we know that’s old, has ‘Michael’ somewhere in their name, has no kids and is single, and was impacted by PittFest?”
Whitaker shook his head. “No. you’re not—”
Santos grinned. “Oh yes. Yes I am.”
“It can't be Robby."
Series
- Part 3 of camboy dennis au
Bookmarked by LittleSquidScribbles
28 May 2026
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When Robby and Dennis started dating, they quickly realized they needed to coordinate their days off.
Dennis took his T shot every Wednesday night. For approximately 36 hours after that, he had an insanely high sex drive. (Which was saying a lot. Robby could hardly keep up with his boyfriend's libido normally.)
Thus, shortly after they made their relationship official, they quietly adjusted their schedules. If anyone noticed, they didn’t say anything—but Dana did wink at Dennis every time he left on Wednesdays, telling him to have a nice day off.
Bookmarked by LittleSquidScribbles
28 May 2026
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His palms began to sweat as he shoved his phone back in his pocket. There was no way Robby wasn’t flagging. Why the fuck would he flag at work? Dennis felt the pit in his stomach grow as he stood and made his way to North 5, running through the worst case scenarios in his head. Did Robby know about his crush? Was he teasing Dennis? It didn't seem like him, but then again, what did Dennis know about Robby?
Well, he knew three things now. Robby liked men, and he flagged mustard yellow and hunter green on the left.
Bookmarked by LittleSquidScribbles
28 May 2026