Jealous Dio is... complicated. When his mother died, Dio thought that his ability to love had died with her. His heart had all but shriveled into a pitiful lump of muscle that pumped pure hate through his veins instead of blood. When he met you, a friend and classmate of his foster brother, Jonathan, he despised you just as he did everyone else. He thought you to be annoying, crude, and loud. You were no better than the shrill voiced shrews that hung around in the seedy taverns and alleyways of the slums. You were nothing but a filthy guttersnipe that had no business mingling with the upper class, and he had intended to put you back in your place.
He bullied you as relentlessly as he did Jonathan, but his tactics were a bit different. At school, Dio sat behind you in class. Sometimes he would grab your braid and dip it into his inkwell, then play it off like an accident while his lackeys snickered at your outrage. Sometimes he would run past you after school and knock your books out of your hands. Once he managed to knock them right into a mud puddle. You screamed and stomped your foot at him while he grinned back at you. Then there was the time he put a snake on your desk causing you to get a rather unpleasant surprise when you lifted the lid. It wasn't poisonous, just a garden snake he found and brought to school especially to torment you, but that didn't stop you from screaming bloody murder in the middle of class and causing a commotion.
Bullying you felt different than bullying Jonathan. With Jonathan, it was merely a part of his ultimate goal to take the Joestar inheritance for himself. He hated naive, noble-hearted fools like Jonathan and enjoyed making the boy miserable, but it wasn't the same kind of joy as he got from making you angry. Dio started tormenting you mostly because he wanted to separate Jonathan from any friends he had, but you were stubborn. Nothing he did seemed to drive you away. He started to see you as a challenge. Bullying you had become something of a game for him and he started looking forward to seeing your angry face every day.
As time went on, you, Dio, and Jonathan had grown older and something had changed in the dynamic between you and Dio. While Dio was purposely treating Jonathan more civilly in an effort to throw suspicion off of himself in his plans to get George Joestar out of the way, you had begun to treat him rather coldly. You know longer glared at him whenever he spoke to you. Now you looked down your nose at him with a stony expression. It very nearly drove him mad. You had no right to look at him that way! Dio wouldn't allow anyone to look down on him... especially not you!!
Over the years, Dio came to a realization. He liked you. He genuinely liked you. It wasn't simply a tolerance he developed for you in the same way he tolerated the sycophantic stooges that followed him around. He had actually developed a fondness for you. At some point he realized that his bullying you wasn't just for his own amusement. He wanted your attention. Though, now he wouldn't settle for your anger. He wanted your approval. He wanted your affection. To have you look at him as if he was nothing but a slimy toad squirming at your feet made him want to strangle you.
Dio couldn't say what it was that drew him to you in the first place. Maybe it was the way your cute face scrunched up when you yelled at him? Could it be the way your eyes glistened when you smiled? Or perhaps it was your care-free attitude that pulled him in? Maybe it was all of those things. All that he knew was that his initial opinions on you had changed. Regardless of your humble upbringing, you had grown into someone of taste and refinement on par with the most noble-born debutante. And yet you still had that fiery side to you that he adored when you two were children. The problem was that whenever you cast your eyes upon him, your smile would drop and your eyes grew cold and empty. He couldn't have that.
"Why do you look at me with such disdain?" He asked you one day. "Don't tell me you're still angry about all the things I did to you when we were children?"
You turned to him, eyes cold as ever.
"I look at you this way because you can't fool me, Dio." You said, voice just as cold as your eyes.
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JJBA Yandere Scenario: Jealousy (The Jo-Foes)
TerrorJoJo villain-centric yandere jealousy scenarios from Tumblr. Reader Insert. Beware of gruesome imagery, canon typical violence, and creepy guys being even creepier. I tried to keep everybody as in character as possible.