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KAKAOBIMI
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2025-04-22
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1/1
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What girl clothes can do for a man

Summary:

Rin needs a girl bestie but all she has is two six foot dude friends. One already said he couldn't go with her because he had stupid work leaving the introvert. But she could work with that, after all she was very convincing.

Notes:

Happy KKOB week! This is for day 2 (of course, late.) and I wish I was better at time mangment and took more time to play with this idea but eh. I can always write more crossdressing later lol.

Work Text:

“Pleasseee” Rin begged.

“I said I would come, just… Not like that!” Kakashi tried, his patience for his friend wearing thin as she tried to get him in on her most recent scheme.

“You have to though! I’m trying to find a date and if you go normally everyone will think we’re dating!” Rin whined and Kakashi just sighed.

“Can’t I wear a rainbow shirt or something? I’ll say I’m gay every five minutes.” Kakashi bargained but Rin shook her head.

“No, because then people will think we're both gay.”

“But you’re Bi?”

“Yes but my last relationship was with a girl. So now I need to date a boy.” Kakashi felt like he was losing intelligence every time he heard about Rin’s love life and wondered why he even agreed to go to the fair with her anyway. “Come on, pleaseeeee-”

Now he was sitting in Rin’s stupid chair, wearing her stupid jewelry, and getting her stupid make up put on his face. Why does he let these things happen to himself?

“And just a bit more, there!” Rin chirped, then spun Kakashi around to look in the mirror and he barely recognized himself. “Well?”

“I look like a girl.” Kakashi shrugged and Rin frowned, gesturing to the mirror again.

“A very pretty girl! I am an amazing stylist.” She stated, then went to grab her wallet and keys. “Alright! Let’s head out.”

Even after agreeing to the idea, helping pick out clothes that weren’t too girly or embarrassing and even getting to choose the wig he still didn’t like the plan. He knew his face was beyond red and his height would draw attention to himself, not to mention with Rin being herself there was no way he could go unnoticed.

“Isn’t this plan ruined with me like this? Don’t we want the attention on you?” Rin looked back and seemed genuinely confused.

“What do you mean? The attention will be on me because I’ll be the one talking.”

“Yeah because the six foot girl who looks sunburned standing behind you won’t raise any questions.” Rin rolled her eyes at his very real concerns and grabbed his sleeve, dragging him towards the door.

“You don’t look sunburned.” Was all she said before he was torn from the safety of the indoors and out into the world. Luckily Rin was right for once and no one really paid him any attention at the fair. Rin had repeatedly failed at getting guy’s attention and it was even funnier to see her awkwardly turn down the girls who flirted with her.

“You could break your rule and date a girl twice in a row.” Rin gasped at him.

“No I could not! And It’s not that dire yet, just wait and watch my magic.” Kakashi rolled his eyes.

“Sure, hey should we get food soon-”

“Obito!” Rin yelled- shit! He’s here? Kakashi looked around for the black haired, black dressed man but didn’t see him. It wasn’t until Rin pulled him straight in front of one of the vendors that Kakashi realized the neon orange and blue covered worker was actually Obito. It was surprising how different he looked with just a bit of color on him for once, as was it nostalgic. “Wow, you look different, almost like a disguise!” Rin teased Obito, then winked back at him.

“Haha yeah, one of the grannies I hang with asked if I could cover for her son. Stomach flu or something. She thinks one of the competing carnival food shops sabotaged him.” Obito rambled and Kakashi tried his best to slip behind Rin. God this was so embrassinggg.

“Aww that’s so sweet. How olds her son?” Rin asked without an ounce of shame as usual.

“Back on the market huh? I told you that girl was trouble. And he’s 15.” Rin yelped and shook her head.

“Pass! Pass! I am too young to be a cougar.” Rin quickly spoke and Obito chuckled.

“Here, as condolences for your break up.” Obito joked as he handed Rin a cotton candy, “Try not to pick up any circus freaks here.”

“I might” She joked back and Obito laughed. Kakashi thought they were in the clear before the worst happened.

“Who’s your friend?” Obito asked, Kakashi internally cursed as he was now put in the spotlight and looked to Rin for help.

“This is Sukea, my cousin.” Rin said, shit eating grin on her face that only spelled more trouble for him.

“Nice to meet you, Sukea!” Obito greeted, shining a bright smile his way. Kakashi just nodded and waved slightly, not wanting to risk using his voice.

“You’ll have to forgive her, she’s shy.” Rin said overly sweetly. Kakashi shoulder shoved her as Rin giggled.

“Leave her alone Rin.” Obito huffed, unsurprisingly coming to his rescue, always a white knight. “Here!” Obito handed him a cotton candy too and he carefully took it. Not wanting to risk getting caught he squeaked out a thanks and hurried off. He heard Rin laugh and talk to Obito a little before running over to him.

“You suck.” Kakashi snapped and Rin pouted.

“It was cute! I was just teasing, you make a very pretty girl.” Rin joked more and now Kakashi stepped on her foot. “Ouch! Not cute!”

“I’m already embarrassing myself to help you out and now you're rubbing it in my face.” He complained and Rin just shook her head.

“I’m not! You know, Obito thinks you make for a really nice girl too-”

“You told him!” He almost yelled and Rin giggled but thankfully shook her head.

“No, he just asked if you would be in town for a while.” She smirked. Kakashi felt his face flush a bit but tried to play it off.

“Oh.”

“Yeah, I told him he could meet us for drinks once his shift was over.”

“What?!” He yelled now.

“Oh please, it’ll be fun. We’ll all go back to my place and you can do a big reveal and shock him!” Rin explained excitedly as if she wasn’t describing a horribly embarrassing sounding evening.

“That does not sound fun! I don’t want him knowing it’s me.” He huffed but Rin just pouted again.

“Come on, won't it be funny to have Obito trying to flirt with you only for you to reveal it was you all along. He’ll get so embarrassed!” Rin laughed, laying out her plan.

“It won’t be.” Kakashi said, realizing too late he forgot to watch his tone. “It’s too mean.” he tried to cover up but Rin was staring at him, shocked. Crap

“I’m sorry, I didn’t realize you…” She said quietly then shook her head, grin returning. “All the more reason too! Maybe it’ll get him to see you in a romantic way.” Rin said, winking but he just huffed.

“All it’ll do is embarrass me. Also if you tell anyone about this I’ll kill you.” He threatened but Rin just rolled her eyes.

“Yeah yeah, let's ride the Ferris Wheel!” Kakashi groaned as she dragged him off but was thankful the topic was dropped. She actually did a great job getting him to forget about his hopeless crush by being hopeless herself. She had absolutely zero game and even when a guy came up to her first she managed to be so forward they got scared.

“You’re coming on way too strong.” Kakashi giggled as she managed to lose the interest of a drunk frat guy, which was certainly a feat.

“It’s called confidence.” Rin grumbled and Kakashi just laughed at her more.

“You have a pretty laugh.” He jolted as Obito spoke, at some point sneaking up behind them. Going red once the complement registered.

“Obito! You don’t think I’m too much right?” She whined and Obito, being the push over he is, just nodded.

“I don’t think there could ever be enough of you.” Rin shouted her agreement before seeming to remember his existence.

“Oh right, are you ready to go home Sukea?” Rin grinned and Kakashi glared but still nodded. Obito stood to his left as Rin blocked off his right, forcing him to walk close to Obito as they made their way back to her apartment.

“Where are you coming from? Rin said you’re not in Konoha often.” Obito asked, clearly just trying to be nice but Kakashi cringed. He couldn’t talk, Obito would undoubtedly notice his voice and then he would… Laugh at him or something. God and they were still in public, this was all so embarrassing, he is so killing Rin. Or making a fake dating profile to catfish her, just some kind of payback-

“She actually is from here, she was just away for work. Why don’t you be a gentleman and walk her home?” Rin covered, he didn’t even realize he had zoned out so hard, not even noticing they were already outside the fair and at the crosswalk.

“Of course! Night Rin.” Obito agreed and was putting his arm out for Kakashi. Kakashi looked to Rin for more help but she just motioned her head to Obito's arm. Resigning to his fate he hesitantly grabbed Obito’s arm and accepted his escort home. God, what was Rin’s problem. She knew he had a crush and now she wanted to get her stupid little hands in his business. Luckily Obito didn’t try to ask anymore questions and instead just pointed out small shops along the way. Kakashi knew them as Obito had already taken him and Rin to them but he still nodded, god he felt like such a jerk. Obito seriously thought he was being nice and walking a girl home and it was just him.

When they got to the parking lot of his apartment complex Obito paused and Kakashi thought he was caught.

“Hey, one of my best friends lives here, Kakashi. Has Rin mentioned him to you?” He couldn’t do this anymore. He pulled his arm free and sped walked to the stairway, just trying to end the night. “Hey!” Obito called and he heard him follow him up the stairs, it wasn’t until he was in front of his own door that he finally stopped and turned back to Obito.

“It’s me.” Kakashi sighed, finally speaking. He looked up and saw Obito just staring blankly at him.

“What?” Whoops, forgot who he was dealing with. He sighed and pulled off the wig and shook out his hair before looking back up. He watched as recognition set in on Obito’s face and his mouth opened.

“Me.”

“Kakashi!?!” Obito squeaked “No way…” He said quietly before he started circling around him, taking in the outfit and jewelry Rin dressed him up in. Kakashi felt his face heat up and reached into his pocket to grab his mask. He was putting it back over his face when Obito grabbed his wrist, now back in front of him. “Wait.” He looked up and saw Obito’s face was flushed and way too close.

“T-this was all Rin’s Idea.” He said quickly, not knowing why he now felt the need to explain himself.

“Okay.” Obito said, sounding completely calm, like he didn’t just find out the girl he was flirting with was his best guy friend, “Why?”

“She said she needed a girlfriend so guys didn’t think she was weird or lonely at the fair.” Kakashi spoke, feeling a bit less embarrassed about this now that he could lay more blame on Rin.

“That does sound like something she’d think.” Obito chuckled.

“Yeah, I don’t know why I agreed. I need to change.” Kakashi sighed, finally feeling his heart rate slow down when suddenly Obito was leaning in too close again.

“Why? You look cute.” Kakashi felt his face redden more and looked away.

“Of course you’d think that, Rin put together the outfit. You think everything Rin wears is cute-”

“No,” Obito interrupted and Kakashi made a face, “We yeah, I do but that’s not what I’m trying to say. You look cute in lighter colors, you should try wearing light clothes more often.” Obito explained, seeming more embarrassed the longer he went on.

“Oh…alright.” Kakashi nodded, trying to not think too hard about how Obito was complimenting him. Obito’s hand that was restraining his wrist was moving his own hand away from his face. Kakashi looked at Obito confused as the other stared hard at his mouth. Before he had a chance to ask what the other was up to Obito’s thumb was brushing against his lip. “H-hey!” He yelped and Obito pulled his hand back quickly.

“Sorry! I just wanted to see if you were wearing lipstick or something…” Obito said sheepishly but otherwise didn’t look too sorry. “It’s not bad but I think you would look better in a different eyeshadow.”

“What, you're a makeup professional now?” Kakashi grumbled, trying to break some of the tension this weird situation was causing. Obito flushed more and laughed a bit.

“No no! It’s just I never thought you’d be someone to get all dressed up, I guess I’m being a bit too excited about it.” Obito said, finally letting go of his wrist.

“I’m really not, it was all Rin-” Excited? Obito was excited that he was willing to get dressed up, and was even giving opinions on what he’d want him to wear next… He looked up and Obito seemed to have realized just how much he said as well.

“I-it’s late! I should get going and-” Obito stammered and started towards the stairway but Kakashi grabbed his sleeve.

“What color?” He blurted out, causing Obito to stop in his tracks and look back confused. “What color eyeshadow do you think I should wear next time?” He had used up the last of his courage for the night and kept his gaze on the floor, hoping Obito would just bolt for the stairway. However the silence he was met with almost made him think the other did leave, if not for the fact he was still holding Obito’s sleeve.

Then there was a lot of noise, shuffling, his own surprised gasp as both of Obito’s hands found his face and a crash as Obito pushed them against the door. Obito’s mouth just as rough, pressing against his lips and hands tilting his head to the side so Obito could kiss him harder. When Obito finally pulled back Kakashi was panting trying to catch his breath.

“God Kakashi,” Obito said breathlessly against his neck, “You’re always so cute, and shy, I could never tell if you were blushing because of me or you just got red easily.” Obito started talking and Kakashi felt immediately embarrassed, becoming very aware that they were outside his apartment where any of his neighbors could step out and see them.

“W-wait. Lets go ins-” He tried but Obito was leaning back to look him in the eyes and cutting him off.

“Was this really Rin’s idea alone? Did she rat me out and get you to do this?” huh, why was Rin being mentioned at all right now?

“I don’t… what?” Obito grinned for a second longer before looking confused too.

“She didn’t tell you I liked you?”

“...No?!” Kakashi said and asked. What? He- No wonder Rin didn’t seem to be worried about tricking Obito with a fake date. Damn witch- Obito was kissing him again, Kakashi tried to pull back to complain about being outside again but Obito didn’t let him. But the other did reach in his pocket and pull out his house keys, unlocking his door. “We need to talk.” Kakashi tried, looking Obito in the eyes.

“Later?” Obito pleaded, but not waiting for an answer as he reached around him, lifting him up by his thighs and carrying him into his own apartment.

“Obito!” Kakashi tried to complain but was quickly giving up as Obito started kissing his neck, kicking the front door close behind them. Obito went straight to his room and lowered him on the bed.

“Okay, want to talk?” Kakashi glared at the other as Obito grinned.

“Shut up.” Kakashi grumbled, slumping his shoulders to let his hoodie fall off. Obito pulled his thin black shirt over his head before leaning forward to kiss him again. “W-wait, let me finish undressing-” But Obito of course didn’t listen, just pushing him onto his back before pulling off Kakashi’s jeans himself and settling on the bed between his legs.

Obito grabbed his waist and slid his thighs under him before leaning in and kissing him again. His hands drifted downwards, getting a pleased sigh from Kakashi that he used to press his tongue into his mouth. Kakashi should feel more embarrassed about everything now but Obito was just making him forget everything the longer he kissed him. It was until he pulled back and looked down at him, then his shirt, that all the embarrassment came crashing back.

“This is so humiliating.” Kakashi grumbled but Obito just kept running his hands up and down his thighs.

“Not for me.” Obito said smirking, he finally let his hands move forward and gently grabbed the hem of his shirt. Kakashi raised his legs a little, trying to just get the stupid frilly thing off. He stopped moving when he realized Obito was still and looked up to see the others just watching him. “No, keep going.” Obito grinned and Kakashi frowned confused before he realized where his ass was and why Obito seemed so glad to just sit there.

“Take it off.” Kakashi snapped and Obito started but left it bunched up at his collar bones. “Hey, I want it off- Ah” Kakashi tried but was interrupted as Obito moved a hand to his erection.

“Just let me have this a little longer? Please?” Obito asked, sweet tone being so wrong in this situation but Kakashi just nodded, losing his fight now that Obito was pumping him at a teasing pace. Just wanting Obito to do something more. “So sweet.” Obito praised before leaning in to kiss him again. Obito let go of him and Kakashi whined at the loss but Obito ignored him, just kissing him breathless. Kakashi gasped as a cold finger pressed against his rim and Obito leaned back finally, looking down between them.

“Obito, move.” Kakashi whined, trying to move again. He was surprised a bit at himself but it was a lot easier to be confident when he knew what was going to happen.

“What happened to you being shy?” Obito said and Kakashi looked up at the other, about to complain again when Obito finally pushed his finger in. Kakashi frowned a bit at the feeling, always awkward at first. Obito moved his free hand back to his dick and started to slowly stroke him. “Just stay relaxed,” Obito soothed and started to move his finger. Obito soon added a second finger and Kakashi moaned lightly.

“Go faster, I want you.” Kakashi said quickly, trying to keep his breathing even. Obito tugged harder on his dick and Kakashi whined.

“I could, you're taking this well. Do you finger yourself often?” Obito asked and Kakashi blinked at the other. Of course Obito had to ask something like that right now. Kakashi turned his head away and nodded. “Were you thinking of me while doing it?” Just wanting Obito to keep moving he gave up on embarrassment and nodded again. He winced as Obito added a third finger. Kakashi didn't try talking as his breathing got quicker and shaky, but then Obito stopped moving entirely again.

“W-why do you keep doing that?” Kakashi whined and Obito just gently kissed his lips.

“This is the last time, you ready?” Oh, finally, Kakashi nodded and Obito kissed him lightly once more before leaning back. He felt the blunt head of Obito’s dick at his entrance and felt slightly upset he didn’t get to see the other’s dick before he had it inside him but wanted it too much to actually care. The stretch was more than anything he’d felt but before it could become uncomfortable Obito was back to stroking him. “You’re so beautiful.” Obito sighed and Kakashi moaned as Obito finally bottomed out. He pulled back only a little before pushing back in and Kakashi moaned again.

“Y-you can move faster.” Kakashi panted and Obito moved his hand from his dick so both could hold his hips before pulling out till only his head was in. He thrust back and Kakashi threw his head back. Obito kept up the pace, hold on his hips tightening as he repositioned so Kakashi was almost yelling on every thrust.

“So cute,” Obito started again, even though he also sounded breathless. “Wanting it rough then tearing up.” Kakashi didn’t even realize he had started crying till Obito mentioned it. Obito leaned down and let go of one of his hands to barce his arm next to Kakashi’s head, now staying deeper on every thrust. Kakashi cried out and reached up, wrapping his arms around Obito’s neck. He was so close, everything felt more intense than he thought it would be that even the slight friction of Obito’s stomach against his dick was too much. His finish surprised him when it came over him and without thinking he bit Obito’s shoulder. He heard Obito groan and slam deep inside him before coming too. Obito stayed there, panting before moving his other hand up to softly comb through Kakashi’s hair. “You did so well, it’s alright, you can let go.” Kakashi realized he was still biting the other and pulled back, wincing for Obito at the sight of the bloody bite mark.

“S-sorry I-”

“Don’t be.” Obito said quickly, kissing him softly to make sure he shut up. “It’s cute.” Kakashi wanted to glare at the other but his eyelids felt so heavy that he was sure if he tried to close them even a little he’d be out. Obito pulled out and he shuddered at the feeling before Obito was next to him, pulling him against him. “Stop trying to fight off sleep, you look stupid.” Kakashi frowned and tried to roll onto his back but Obito kept him down.

“Stop it, I want to talk. Seriously.” Obito just rolled his eyes and pulled his head into his chest.

“Yeah yeah, we can in the morning after you take off your makeup and we shower. Just sleep.” Kakashi wanted to argue but he really was tired, he had never come that hard before.

“Fine.” He sighed, closing his eyes. Obito just hummed and tugged his comforter over them. Despite all the good it did him he’d never wear a wig again.