Context; Same session as “Intimidation is key to Seduction”. This is an Overwatch-based session, and we have just met Zarya - a Goliath woman - who challenged us all to a spar. Now, my half-elf Ranger is a huge Lesbian Disaster™ and decides she wants to seduce the woman that could crush her with two fingers. Our Halfling Rogue, Halfling Cleric, and our Air Mephit Bard decide to help doing so.
Robin: (Rogue) I cover her eyes by jumping up her back!
Fenley: (Cleric) And I sweep her off her feet.
DM: Alright, Robin roll me Dexterity, and Fen roll me Athetics. (Robin rolled a 17, and Fenley a 15. Zarya failed her dex saving throw) Alright, she is toppling over and falling. You gonna go catch her, Adrie?
Adrie: (Me) Oh, definitely. I have a -2 on strength though, the only way this is gonna work is if I Nat20 it. [proceeds to roll a Nat20] Oh.
Windy: (Bard) [barely stifled laughter while the rest of the group hollers]
DM: [laughing] Alright, you just catch her in your big womanly arms, and she lands right in your lap. What now?
Me: (OOC) Honestly, I didn’t think I’d get this far. Help me out y'all. Help the twig hook up with the mountain of a woman.
Windy: Hm.. Oh! Pretend you’re hurt and that you have to go see Mercy.
Me: How– Oh, I get it. Perfect.
(Shenanigans happen, and Robin and Fenley have to roll persuasion rolls that I am simply too hurt to be treated by the - very capable - Cleric)
DM: Adrie, I’m gonna need you to roll me either a Deception or a Performance check to convince her.
Me: (OOC) Oh man.. I’m horrible at both! Well, here goes nothing. [rolls a Nat20 in Performance] Oh my god. The dice are with me!!
At that point, the entire party began laughing and hollering again.
DM: Alright, I think we can leave it at this point for this week. Since you’re all going out to drinks later in the session, maybe you can take her out to dinner then.
Me: [wheezing with laughter] Definitely.