49. Red Flags

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The date started off so well,

Begin my night not expecting the fright of my life,

She was perfect from what I could tell,

How could I not see the danger right in front of me?


"And here I thought you'd betray your dear old dorm head again, I have to stay on my toes around you at all times huh?" Leona purred as his ears twitched, turning onto his side, holding the side of his head. He was his bedroom balcony, his freshman standing by the entrance of his room, a stern look on his face.

"Hmph, unlike last time, this is for a noble reason," Jack said, crossing his arms, looking at hi shoes before back up at Leona's bare back.

"Right... and when are you seeing her again?" Leona's tail flicked the air, "..Tonight," Leona relaxed onto his bed at the mention of that, "Well go on, don't be late for your little date," Leona teased, making Jack stiffen, his ears visibly perching higher than normal, a blush coating his cheeks in embarrassment.

Leona feels the embarrassment ooze off his freshman, making him smirk bitterly, "And don't spare those details, I wanna know everything," Leona's voice grumbled at the last word, making Jack snap back to reality, away from the image of you forming in his head.

"Yes prefect," Jack said as normally as he could before leaving, closing the door behind him. As it closed with a thud, Leona turned back to stare at the door in a bored matter, he then closed his eyes in thought. 'Lucky...'



While in Ramshackle dorm, you applied the last bits of your more fancier makeup, this time you decided to look more business casual, your pants were flared / slightly baggy around your legs, striped with pink and black, wearing a dress shirt with a dark purple tie, a heart, clover, and diamond design imprinted on the edges in the color of lavender.

Your hair was let down naturally, having a loose and very low ponytail, the green bead from Leona and the others held your hair together as it pressed against your back lightly, it was pushed up slightly to give your hair around your head more circular look, not defining your face shape as much. Speaking of which, you slipped the gifted fingerless gloves from them, opening and closing your hands as they hugged your [skin tone] hands nicely.

Standing in front of a mirror, you double checked your two thin belts, one dark purple and the other a slightly dull pink, they looked like sashes honestly. They were perpendicular to one another, crossing over at the side of your legs. It wasn't practical, but you thought it looked nice.

You looked at your reflection in the mirror, it was strange to see you in such a state, so... confusing? Like many things were off but you're still here looking normal—

A knock was heard, sending a signal that it was time to go, hurrying down, you slipped on your platform HEELS, slapping the belts into place as you opened the door. He didn't bother changing your attire, so it was awkward for him to see that you did. Not that he was complaining.

"Why'd you change? We're just talking with Azul?" Jack asked, (like the slight dummy that he is.) You rolled your eyes and closed the door behind you, sending a quick wave to the ghosts that resided within it before turning to your beastman partner.

"Clothes are like a second skin, when it's comfortable, you feel better," you said matter of factly, Jack had no opinion and nodded at that, taking more in of your outfit. His lips parted slightly as he took in the way your pants hugged your upper legs, the slight sway of your hips defined by the sashes, and he felt his cheek warm at the side of the Savanaclaw student's gifts adored on your body as accessories.

𝕋𝕎𝕀𝕊𝕋𝔼𝔻 ℍ𝔼𝔸𝕍𝔼ℕ [HIATUS] ➼Twisted Wonderland x Hazbin! F!ReaderWhere stories live. Discover now