Requested by: Bushi_fish

A/N: Had to choose between this and first kiss head-canons. If you guys want some first kiss head-canons, all you have to do is ask. I just chose this prompt first because it seemed more interesting. 

Yumeko Jabami

-Was having a good time at first, until her opponent started making some rather suggestive comments in your direction. 

-You weren't even participating in the gamble, and since her opponent was so distracted, Yumeko got pretty annoyed. 

- "S/O, come here." she instructed, patting her lap. 

-Her opponent looked at you in shock when you instantly went to her side. Straddling over the left side of her thigh and grinning innocently. 

- "I suggest you pay attention to the gamble. Unless...you're too distracted to keep going?" 

-Yumeko tauntingly grabbed your face and ran her thumb across your lips. Smirking when her opponent looked so irritated. 

-Since she's not scared of PDA, she nonchalantly kisses you whenever and wherever. Not afraid to show everyone that you two were definitely dating. 

-So she does just that, turning your face towards her and planting a sweet kiss on your lips. Smiling the whole time and shocking her opponent, the referees and any watchers who have been witnessing the whole event. 

Mary Saotome

-Very salty about the whole thing. 

-She stays quiet at first, her jealousy growing more and more noticeable the more her opponent flirted with you. 

- "Oi...stop ogling my girlfriend and play the game already. She's not your eye candy to look at so fuck off."

- "Oh? Is Saotome-San jealous? That's funny... Hey cutie!" her opponent winked at you. "Why don't you go for an upgrade? I'm wealthier than this broke excuse for a girlfriend anyway."

-Mary looked pissed. About to yell out something when you snaked your arms around her neck from behind her. A sly look on your face. 

- "Ew. Why would I go for such a downgrade? You disgust me."

-Her anger quickly turned into amusement as she burst out laughing. Her opponent's face looking like their ego had been crushed. (Because it was)

-She caressed the side of your face and smiled. Feeling more confident about the gamble with you by her side. 

Midari Ikishima

-While her crazy persona masks it well, she's actually pretty jealous that someone else was hogging all of your attention. 

- 'I'm shooting them. I'm shooting them. I'm shooting them.'

-You can visibly see her trying to reach for her gun, so you have to interfere before you end up having to hide a dead body.

- "Midari," you make her face you, "Look at me." 

-Unable to resist the temptation, she leans in and kisses you. All the while side-glaring at the person who flirted with you. 

-Caught off guard by her sudden boldness, you almost backed out when Midari pulled you closer, effectively locking you into the kiss with no way of backing out. 

-Feeling like a third wheel, the person who flirted with you awkwardly walked away. Backing out of the terrifying gamble and using this as an opportunity to escape. 

Kirari Momobami

-Amused that the person she was gambling against didn't know that you two were dating. 

-Everyone watching (even the referees) watched in horror as her opponent flirted with the president's girlfriend right in front of her. Pretty much digging their own grave. 

-You and Kirari on the other hand, just seemed entertained at the fact that this clueless and pitiful individual has no idea what they were doing. 'How unfortunate' you thought. 

- "Hey, are you single? Maybe when we're done, I can take you to a really nice place and we can hit it off."

-Finally, Kirari intervened, "I apologize but she is not single. In fact, she is to be engaged to me."

-She smiled and beckoned for you to come closer. A smug smile on your lips as you leaned against the back of her chair. "Sorry, I'm taken sweetie," you winked playfully. 

-Her opponent looked stricken with horror as they went bankrupt. Losing all of their life savings and becoming a housepet after Kirari won the gamble. 

- "I would've gone a bit easier on you...had you not flirted with my S/O."

Ririka Momobami

-Was watching you gamble when all of a sudden you were getting flirted with. Thanks to your attractive looks and kind demeanor, your opponents figured that they could distract you with a few subtle flirts as well as get a chance to get in your pants. 

-Your relationship with the vice president was kept a secret, however she was still dying inside. 

-Hiding her pouty expression behind her mask, she walked over next to you and just stood there like a personal body guard. Pretty much glaring at your opponents through the eye holes of her mask. 

-You smiled at her obvious jealousy, and smiled even more when you found your opponents cowering over the hard gaze of your girlfriend. Afraid to even look in your general direction. 

-She was pretty intimidating with her mask on. So it was no surprise as to why everyone caved and lead to you winning the gamble. 

-Afterwards, she pulled you to the side and hugged you like a crying toddler. Saying to never leave her for jerks like them. 

-You hugged back and teased her on how cute she was back there. With her growing flustered right there on the spot. 

Runa Yomozuki

-Was spectating one of your gambles. As a referee, she had to commit to absolute neutrality, even if you were her girlfriend. 

-So when she saw one of your opponents blatantly flirting with you right in front of her, she couldn't physically do anything as it wasn't against the rules. 

-However, she did make it known that she was slightly annoyed. 

-The further the gamble went on, the more your opponent flirted with you, and the more irritated that Runa got. 

-Sucking on peppermint stick, Runa had thinned the candy down to take the appearance of a very sharp point. Emphasizing the sharp needle-like shape to the opponent and making them shiver in fear. 

-Thanks to her subtle death-threat, your opponent backed down and you ended up winning. 

-Demanded that you play video-games with her to make up for the fact that she was jealous. 

Sayaka Igarashi

-Unsure of what to do. Since you were the one participating in the gamble, and she wasn't, she had no choice but to observe as a spectator. 

-She tried to be as professional as she could, however her eye kept twitching every time your opponent asked you out. 

-She wanted to tase them so bad. 

-At the end of the gamble, you ended up winning and was about to leave with your girlfriend, when you felt someone grab your hand. 

- "So...about that date--"

-Sayaka grabbed your other hand and just dragged you away from them as fast she could. Unable to withstand the urge to punch them. 

-When you were finally alone together, she started mumbling to herself about beating the shit out of them for flirting with her beloved. 

-You ended up having to comfort her for fear of her accidentally tasing someone for you. 

Yumemi Yumemite

-Was doing a gamble idol-show thing with you. 

-You were very, very cute to her audience, and this lead to some unnecessary cat-calls from most of the people in the audience.

-She snapped. Hard. 

- "How disgusting do you all have to be to cat-call MY S/O in front of me! You all are just filthy perverted losers who jack off to this shit! Go to hell!"

-She was extremely pissed. Grabbing your hand and dragging you off the stage. Cancelling the idol-show. 

-When you got to her dressing room, she hugged you tightly against her and pouted. 

- "Y-Yumemi! You just insulted your fans...what would--"

- "I don't care about those perverts..." she huffed, "I could lose all of them if it meant keeping you..."

-Strangely very wholesome. 

Itsuki Sumeragi

-Not very good at composing her jealousy. 

-She has the obvious "jealous girl" vibes radiating off of her. Her posture is all stiff and her face is scowling. 

-Since she was the one gambling, and not you, she decided that she would "show off" a little by completely destroying her opponent in front of you. 

-Payback for flirting with you right in front of her. 

-Proceeds to rip out their nails and hang them proudly in her display case. You think it's a bit odd but nevertheless, she seemed proud of her win. 

-Everyone who watched barely even looks at you for fear of getting their nails torn off. 

-I admit, she went a little overboard, but her confidence just soars whenever your heart is on the line. She doesn't want to lose you after all.