So, here they are. Naruto and Sai sit cross-legged in front of each other on the floor. Sai's considering if he should really let Naruto know about his past. It's a bit personal and he hasn't opened up to someone in such a long time. This whole situation feels awkward and new to him.

"Are you sure you want to know?" Sai asks as his eyebrow raises. An exasperated sigh leaves Naruto's lips as his whole body seems to deflate. Sai's been beating around the bush for almost thirty minutes and Naruto's ready to give up on him.

"For the last time, yes! I want to know," Naruto answers. "It's very important for me to know why you seem to hate Sasuke the most out of everyone I've talked to."

"Ugh," Sai finally gives in with a huff. "I'll tell you, but it's a long story."

"I have all day," Naruto responds as he puts his face in his palms.

An awkward moment passes by and Sai has yet to say anything.

"Well?" Naruto says, eager to get this story started. Sai waves at him dismissively.

"Don't get your panties in a twist. I just don't know where to start."

By now, Naruto is annoyed but is patiently waiting for Sai to reveal some of his secrets. Sai wraps his arms around himself and heaves out a sigh.

"There was this boy named Shin, he was my roommate way before you came along. Last year he disappeared from my life. I don't know where he went or who he was with," Sai pauses and looks down towards his lap. "I loved him. He was my first love, but he didn't reciprocate those feelings for me."

Sai closes his eyes as he continues. "Shin became one of the many victims of Sasuke, as much as I hate to admit it. Sasuke used him, convinced him that he only had eyes for him, but that two-timing bastard Sasuke was already dating someone else. Once the other person found out about Shin, he was bullied and picked on constantly by that asshole."

"Do you remember the name of that person?" Naruto asks, feeling bad for this Shin person. Naruto knows all about how bad bullying can get and doesn't want to think about Shin receiving the same treatment.

"No, and I bet they still go here too. I'd kill them if I ever saw them."

Sai opens his eyes and chuckles. "Well, that's if I ever knew what they looked like too."

There's a silence between them. Naruto wordlessly encourages Sai to go on by nodding his head.

"When Shin was so distressed to hear that Sasuke already had a boyfriend, I tried to comfort him. He told me that no one will ever love him like Sasuke did, and me being stupidly in love thought it would be the perfect time to confess my love for him."

Sai bites his bottom lip and Naruto can already guess what he's going to say.

"He rejected you, didn't he?" Naruto asks for confirmation. Sai takes a deep breath.

"Shin was so in love with Sasuke. He looks angelic but has the tongue of the devil. He'll whisper sweet nothings into your ear, fill your silly little head with words of affection, make you think he loves you and that you can't live without him. Sasuke will tell you everything you want to hear and trick you into loving him. That's what happened to Shin," Sai pauses as he runs a hand through his short black hair. "I poured my heart out to him and he told me that he can never love me, that Sasuke was his one and only."

"I'm sorry," Naruto whispers as he reaches over to place a hand on Sai's knee.

"After the heartbreaking news, Shin started to act weird. He stopped coming to class, he stayed out late and would be gone for days at a time. And then one day, all his stuff disappeared from our room. All the posters were ripped from the walls, his clothes vanished from the closet and all his homework was tossed into the waste bin. All at once, he disappeared from my life and it's just because Sasuke didn't love him back."

"Weeks later after his disappearance, I got a text from an unknown number, which now I assume was Shin, saying that he's doing okay, that he's cutting all ties to this wretched school, that he never wanted to see me again as long as I go to this school, and that we probably won't meet ever again."

By now, silent tears rolled down Sai's cheeks. His voice doesn't waver as he talks. It stays strong as he reveals this painful story to his roommate. Naruto unconsciously moves closer to Sai in an attempt to comfort the crying teen.

"I continue to hold this grudge against Sasuke because Shin was the only positivity in my life. He's the one that supported me when no one else did. He's the one that encouraged me to paint and improve my art skills. He was my only true friend, and I fell in love with his smile, his generosity, his compassion, his voice, and his eyes. I fell in love with everything that was him or related to him. But Sasuke, Sasuke had to take that all away from me!"

Sai put his face in his hands, shielding his tears from Naruto's prying eyes. He silently cries as he remembers the countless nights his old roommate would cry over Sasuke and he'd comfort Shin but conceal his strong feelings for him.

Naruto embraces Sai. It's the best he can do right now because he's absolutely speechless.

"I hate that bastard. If it wasn't for him, Shin would still be here," Sai mumbles. "But if you still like him, that's fine. I have my reasons to hate him, and soon you'll have yours too."

Naruto releases him from the hug and Sai quickly wipes his tears away. The whites of his eyes have turned pink and his eyelashes are wet with little droplets. Naruto pats Sai's shoulder and smiles.

"Thank you for sharing that with me and I'm sorry this happened to you," Naruto says softly. "I really wished it could've worked out between you two."

Now knowing this information, Naruto doesn't know what to think of Sasuke. Of course, Naruto never really like Sasuke in the first place, but he was slowly warming up to the little devil. But this, this hit him like a freight train.

Sai chuckles bitterly. "We would've probably never worked out. I'm too much of a brat and he spoiled me all the time."

"Have you tried dating other people to move on?" Naruto asks and Sai shakes his head.

"All the guys here practically bottoms, which is probably why Sasuke fucking thrives here," Sai explains as he rolls his eyes. "I need me a guy like... Let's see... Who's a delicious top other than Sasuke?"

Naruto shrugs. "I would say Gaara, but he'd probably kill you."

"He seems like the perfect brat tamer, but I'm pretty sure he's not into all the lovey-dovey stuff. Guess I'll be alone forever," Sai jokes as he slowly gets over his sadness.

Naruto smiles and shrugs. "Who knows, Itachi might fall head over heels in love with you if you two ever meet."

Sai laughs and smacks Naruto's shoulder. "Oh please! I would love it if Itachi gave me the same treatment he gives you. He might as well be your Sugar Daddy."

"I probably need him to be my Sugar Daddy so he can pay for my college and all I'd have to do is suck his dick," Naruto says as he laughs.

"Do you even know how to suck dick?"

Naruto laughs again. "Not at all!"

They both start cracking jokes about things, mostly about how good of a Sugar Daddy Itachi would be. It's only when they hear a knock on the door that they stop laughing. They look at each other, seeing if the other will stand up first.

"I'll get it," Sai reassures Naruto as he stands. He opens the door slightly and peaks his head out. "What do you want?"

Naruto hears someone clear their throat and ask, "Is Naruto here?"

...

A/N: Now you know why Sai hates Sasuke.