Sasuke dresses Sai up in a cute little dress. He expects Sai to be embarrassed, but he’s completely unfazed. Sai turns it back on Sasuke like, “You’re turned on by cross dressing?” in his innocent voice and it makes Sasuke blush into oblivion.
thanks for the prompt, anonymous! :D
pre-sasusai. obvious warnings for crossdressing, arousal. mdni.
Infiltration mission. Sai had done plenty of these, but somehow, this was the first under these particular circumstances.
"You'll have to be believable," Sasuke said, unloading the shopping bags he'd just arrived at their rooms carrying. "Wig, makeup, perfume, dress. Shoes. Stockings."
"You've done this before?" Sai surmised from Sasuke's casual mode of speaking.
"Several times," Sasuke said, glancing up at Sai. A pale pink blush suffused his cheeks, and he looked away. Interesting. "I'm too recognizable these days, though, and we can't use genjutsu. So it has to be you. Shame you don't have any experience."
"I'm skilled in many kinds of infiltration mission," Sai said. "With your guidance and assistance, I don't foresee any complications. And if there are, that's why you're my backup." Sai smiled, and it felt almost natural on his face.
Sasuke cut his eyes to Sai's face again, then motioned him close. He patted the bed beside an assortment of cosmetics in a manner Sai could only describe as brusque. "Makeup first, then we can do touch-ups, if necessary, once you're ready to go."
Sasuke unscrewed a small pot of something that smelled sweet and powdery.
"Should I apply the makeup? I seem to recall that Sasuke-kun isn't very artistic."
"It's different. Trust me. Now be still."
So Sai was perfectly still for a few minutes while Sasuke applied creams and powders and paints to his face. Then the other boy held up a mirror for his perusal. "Here."
Sai looked… pretty. His skin was pale as ever, but now looked poreless and even, and his cheeks appeared as if they were blushing naturally. His lips seemed even poutier than usual, and were painted a pale, glossy pink. His eyes looked big, the lashes dark and long.
"I was right to trust you," Sai said, with another smile.
"Hm," was all Sasuke said, but then, Sasuke had always been, as they say, a tough nut to crack. Then, after a second of studying Sai's face, he added, "It's good that our target likes the babydoll look. Your skin is perfect for it. Now let's get you dressed."
Once Sasuke gave Sai the privacy to change into a pair of frilly pink panties, he was hands-on in dressing Sai, noting, "Good thing you don't have much body hair," as he rolled an opaque white stocking up Sai's leg. It might have made Sai uncomfortable, had he possessed any sense of bodily modesty.
"How tall are you?" Sasuke asked as he carefully pulled the dress, a pink thing frothy with lace and silk, over Sai's head. "About 170?"
"172," Sai said. sliding his arm through the sleeve.
"Good thing our target's a tall man, or else this might not work. Can't be a babydoll if you're taller than him."
"No, I suppose you couldn't," Sai agreed, noting Sasuke's unusual talkativeness with interest. He'd expected this to proceed with very few words exchanged. He didn't mind Sasuke speaking, though. He had a pleasant voice.
"Gotta cover up your Adam's apple," Sasuke said as he draped a satin and lace choker around Sai's throat, then he tied it. "Let's get you zipped up now."
Sai felt the pressure of Sasuke's knuckles at the small of his back, then sliding unexpectedly slowly up his spine as he zipped him into the frilly pink dress.
As Sasuke walked around to Sai's front to examine him, Sai noticed a peculiar glimmer in his eyes, a light flush in his pale cheeks… he gave Sasuke's body a quick, assessing up-and-down and saw a fullness in the crotch of his pants that hadn't been there the minute before.
Sexual arousal. Of course. He'd read that crossdressing was a common fetish, but he'd never have expected it from Sasuke.
He couldn't have been expected to. He knew almost nothing of Sasuke's sexual proclivities, aside from the fact that he didn't like girls. He didn't count this as a failure, though—he didn't think anyone knew much about Sasuke's sexual proclivities.
Sasuke helped him get into the wig, and Sai examined himself in the tall mirror by the door.
"Don't you feel pretty?" Sasuke smirked, as if he expected Sai to react in embarrassment. As if Sasuke might have, once upon a time.
But Sai wasn't embarrassed. He did feel pretty, objectively, with no shame behind it. Delicate, and sweet, and demure, and just plain… cute. He felt cute, too, in a very subjective way, with his snug stockings and the lace at his throat and the silky dress tight around his waist. He gave himself a testing smile, pleased to see how the apples of his cheeks seemed to glow with the blush Sasuke had applied.
"You look… really good," Sasuke said from behind him, viewing him in the mirror as well. His face was pinker than Sai's, and he wasn't even wearing any makeup.
Ah, here was a chance to poke friendly fun at Sasuke, therefore hopefully bringing them closer together.
"Sasuke-kun's turned on by cross-dressing?" Sai asked innocently. Then, in what he hoped was a teasing voice, he added, "I can leave the dress on after the mission, if you like."
Sasuke abruptly turned bright red and seemed to hold his breath, eyes going wide. Was he not aware of how obvious he was? Even Sai could tell, and that was saying something.
But then Sasuke surprised him. He quickly gathered his composure, leaned against the wall with his arms loosely crossed, and said, "You know, maybe I would like that."
Well, then. Wasn't that interesting. Sai hadn't foreseen that as a possible outcome of his friendly teasing… but he couldn't say he minded much.
Mind spinning, pleased with himself and this whole evening so far—and looking forward to later, Sai smiled. "It's a date."
Okay so I’ve been watching Naruto shippuden lately and I’m in literally rare pair hell right now. I’m obsessed with Sai right now and there is legit nothing with him. I’ve gone through so many ships to find something but there is like nothing. I’ve gone through Sai x Sasuke, Sai x Gaara, And Sai x Naruto. The only reason I haven’t gone with Sai x Ino is because I’m waiting until I fully finish shippuden. I’ve gone through all of the fics with those ships that aren’t side lining them and there is such a drought. The Sai x Naruto “ship” fics are just sidelining for Sasunaru, pushing the plot or just having Sai and the replacement. I love sasunaru but I’m not in the mood for that right now. I’ve gone through legit so many websites to find anything with Sai. I went back to WATTPAD!! Like crazy! He’s been a character for legit over 10 years and there is nothing on him. With the Sai x Sasuke there is a legit panel in the manga of them having sex and it’s not a more popular ship, okay… 🙄 (probably cause people don’t read the mangas)
To sum this up, I need some more sai fics with any ship or even without . So if you have any recommendations any app/website then please share!
