Diego x Reader: "Experience"

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Diego Brando. Of course you knew him very well by his reputation: one of the best up and coming jockeys of the western world. He was your primary competition in the Steel Ball Run Race, as you were quite the rider yourself. There was no use in denying your abilities. You knew you had a natural gift for riding horses. Or maybe you should call it an unnatural gift...

As a long time participant in the races, you knew some of the tricks and cheats some jockeys had up their sleeves: how they could "read" their horse, the other horses on the track, in order to tell what their next move should be. You, however, spoke to your mare. You had always been able to talk to her, though you didn't dare tell anyone else about these strange powers. And she wasn't just your horse, she was your companion. Dancing Queen had been your preferred riding mate for the last three years. You had been through everything with her at your side. And now you were determined to finish this race.

You had often encountered Diego Brando in these races, though the two of you had never spoken. He rarely spoke to anyone other than his largest rival Johnny Joestar. But when Joestar dropped out of the running, you were likely the next one on his hit list.

Once the actual Steel Ball Run preparations began, you were unable to find him in the crowd. There were so many riders from so many placed: you were positively thrilled to race everyone! And yet, your stomach still twisted with nerves at the thought of Diego Brando. You first caught his eye during the very start of the race. You had been searching do him beforehand (and little did you know, he had been searching for you) but only spotted him at the blow of the whistle. Within an instant you were on his trail.

You ended up finishing second, just after Diego, due to some sort of technicality in the rankings. But you were content with the score, having enjoyed the race thoroughly. There was something different about racing through the countryside, the sun's rays sparkling off the lake the wind blowing your hair in all directions. You much preferred it to the loud grungy tavern you were sitting in now.

You sighed as you heard a shout from behind you, cries of "Brando!" and "There's the winner!" and uproarious applause. You scoffed: you hadn't been met with such a greeting when you slouched into the tavern, hot and disheveled. You were about to retire for the night, set your drink on the table and to up to your room, when the commotion died down. The table shook as someone slid into the chair opposite, you extending his gloved hand in greeting. Your eyes darted upward to see that familiar face.

The crowd was silent as you stared, your eyebrow raised questioningly. His expression was not his usual disapproving scowl: he was somewhat condescending, sly as he smirked at you, though you could see his calculating eyes sizing you up behind that feigned gesture of friendliness. You felt yourself beginning to tense up under the watchful eye of the masses, not sure whether to give in and accept the offer or run away to your room under all the social pressure. But after a long pause, he spoke.

"Congratulations, Miss (l/n). You raced quite well out there today." He smile was mischievous, and his tone almost sarcastic as the audience gasped. You gulped nervously as you took his hand, fingers trembling in his.

"As did you, Mr. B-Brando." You wanted to pull your hand from his, but he wouldn't let you. Hopefully, no one noticed the flush on your cheeks as he leaned in.

"Please, call me Diego."

He approached you every time you found yourself at an in or a tavern. After the first stage, the crowds began to disperse, but his attention remained focused on you. It was terrifying, for sure, yet also thrilling in a way. You couldn't tell whether he was assessing you for weaknesses, earnestly getting to know his competition, trying to form an alliance... Or was it something deeper?

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