So, here's a discussion from the discord...
Ruby x Jaune: Lancaster
Nora x Jaune: Double Lancaster
May x Jaune: Diet Lancaster
Jessica x Jaune: Double Diet Lancaster

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So, here's a discussion from the discord...
Ruby x Jaune: Lancaster
Nora x Jaune: Double Lancaster
May x Jaune: Diet Lancaster
Jessica x Jaune: Double Diet Lancaster
When did May realize that she loves getting her tits smacked around by Jaune?
"It wasn't on purpose or anything!" May felt her face flush, "But one day, I was passing by Jaune, we were in a really tight position and he accidently slapped my chest and I squeaked! He apologized... but my face was so red, and my legs were trembling... I... I asked him to do it again."
"It was... an odd thing, not that I minded her uhm, breasts are REALLY soft." He shrugged, "I make sure not to do it too hard, cause I still don't want to hurt her.
Though May didn't say anything, the needy little short stack kinda wanted to try it harder! But that was something they'd have to build up to!
Based on @palaceofpassion’s Combined Arms content that gave May Zedong a desert background (and uncomfortably huge boobs)!
Pyrrha: *looking at her cards during Combined Arms poker night* Hmm…one card, please!
Jaune: *dealing* …one card for the tall redhead who has taken everyone’s chips tonight…! 😑
Pyrrha: 😇
May: *down to the last of her chips, reaches for the deck* I’ll take two cards, and if the merciful gods of the desert see fit to bestow a good hand upon me…
May: *looks at her cards*
May: …may the mother of your camel spit in your yogurt! 🤬
———————————————————
May: *knocks on wood*
May: *hangs a horseshoe for good luck*
May: *kisses lucky rabbit’s foot*
Pyrrha: Wow, May, I never realized you were superstitious!
May: I come from a long line of flat-chested women. One day, my grandmother’s camel spit in the eye of the village witch!
May: *holds up huge, uncomfortable-and-plain-yet-still-extremely-expensive bra* Ever since then, we’ve been growing ‘em like this! 😩
Ruby's just a little jealous
Also a slight headcanon that May was a fan of Summer growing up and crafted her sniper-axe after Sundered Rose.
Pyrrha: Good morning Dear- MAY!
May Z: *Is a mermaid* I'm- I'm fine!
Pyrrha: What- How-
Jaune: What's- OH MY GOODNESS!
May Z: Please don't freak out! I can Explain!
Jaune: ...
Pyrrha: Please do?
May Z: Well ... It's (......)
Pyrrha: Could you please repeat that?
May Z: It's ... Mermay ....
Jaune: One more time please?
May Z: It's Mermay! this- this just happens every year.
Pyrrha: Huh.
Jaune: Well ... You still look cute!
May Z: *Blushing* Thank you?
Pyrrha: Is there anything we can do?
May Z: Please get me a wheelchair.
Jaune: I'm on it! *He rushes out*
Pyrrha: .... Have you ever "Done It" like this?
May Z: *Deep Red* I'd like to!
Prompt
Neon along with Reese and May usually deny their crush on Jaune and give different reasons why they each don't like him. But when they witness him and Cinder getting close with the later even recuperating his pick up line... hey interrupt and act like jealous girlfriends. He belongs to them! Not that bitch!
(Jealousy) (Flirting)
Neon along with Reese and May denied that they have a crush on Jaune Arc, mutual friend.
Neon sees him as a dorky goofball and not her preference.
Reese saw him as a bro and not boyfriend material.
May took a oath of celibacy and chasity due to lack of interest and her bashful nature and she don't Jaune isn't her kind of guy.
"Well the name's Jaune Arc. Short, sweet, rolls off the tongue, ladies love it."
...That until they witness Jaune Fucking Arc and Cinder Bitch Fall getting close and Jaune using his dumb cheesy pick-up line on the ashen-haired bimbo bitch who look at him with amusement on her face.
"It certainly is~" Flirted Cinder in a sweet-sounding tenor as she rested a sole hand on his chest in a seductive manner.
Which cause Neon, Reese and even May to snapped in jealous-rage as they rushed up at surprised Jaune and clinged strongly onto him and glared heatedly at the ashen-haired, gold-eyed bitch who look at them in amusement at their petty jealousy.
pyrrah, velvet, plus 3 ships of your choice reaction to Jaune losing against them in strip poker
Last three were picked by a spinner with all the RWBY females on it.
Pyrrha (Arkos)
Surprised that she won since she usually is terrible at poker (She has zero poker face), but insists that he undress to the level his comfortable with if he wants to stop. And... she wouldn't mind if he makes a bit of a show out of it >///<
Velvet (Scarlet Knight)
She's actually really good at poker. Coco helped her learn and she'd play with her team every now and then. And some people just don't think she can lie. Either way, she'll enjoy the rewards her skillset have given her. Maybe Jaune would let her record it?
May Zedong (Berthier/ArcShot)
Stares intently at him, waiting for him to accept defeat and reveal his goods to her. She's more eager for it than she'd like to admit
Winter (Winter Knight)
She expects him to honor the terms of the loss without question, but does begin to blush rather heavily as his clothes start coming off
Carmine Esclados (Golden knights? (Is that a good ship name for them?))
Sits back, relaxes, and waits for her man to bare it all for her, slowly sipping from her drink if she has one and not breaking eye contact with him as he strips.
May Z: *folding clothes as she sat on the floor* Jaune: *reading the newest issue of X-ray and Vav* May Z: *looks over at Jaune and ponders then grabs a pantie and uses her sniper skills to elastic shot one of her pantie at his face* Jaune: PFFFT!?!, May don’t throw Clothes around! *breaking his focus on his comic grabbing the underwear and folds it* May Z: hehe, you love my panties, but you’re right it worse enough my bras snap of their own will *continues folding their clothes*
Jaune: well you have boobs that define gods. *smirks*