Disclaimer: Naruto and its characters are the property of Masashi Kishimoto. No profit is made by this, no harm intended.

Note: This is an OLD fic I wrote over a year ago and I never posted it. I thought it would add it here in the hopes that it makes someone happy.

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First Times

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Jiraiya looked at his reflection in the small round mirror hanging in the rented room. He wiped away a streak of red and white face paint, and watched his face slowly reemerge.

"Do you think they bought it?" He glanced at the reflection of the figure behind him, noting how easily Orochimaru's slender fingers tugged at the obi, undoing the intricate bow at his waist. The long roll of red fabric unraveled and slid to the wooden floor. His black, upswept hair left the slender neck exposed. From this angle, Jiraiya could almost imagine that his teammate really was a girl.

"My dance was flawless and while your performance may have left something to be desired, these were simple folk tonight. Many of them would not know the difference between Kabuki and Noh."

Jiraiya nodded, wiping off a long streak of white makeup. His eyes slid over to the reflection again and he paused. The outer robe of the kimono slid from Orochimaru's shoulders and fluttered to the floor.

"So you think we got away with it?" His eyes traced the slim neck down to the round shoulders, before dipping to the slim waist.

"That is a fair assumption. They insisted on paying us even though we refused. Tsunade is handling it."

Jiraiya realized he was still wiping the same spot on his cheek and quickly moved on to the red makeup around his eyes.

"You don't think they'll want a repeat performance, do you? This mission will never end if we keep getting stuck in each town." He focused on his own reflection, shutting one eye to get at his eyelid. The dim lighting made it difficult to see, but he was fairly certain that his eye was no longer bright red. Various robes rustled behind him, and he was tempted to peek, but then he realized what he was even considering and continued to clean off the other eye.

"I'm going to take a bath. I'll ask Tsunade what she thinks when I get back. I need to get all this junk out of my hair." Jiraiya snorted catching Orochimaru patting his hair in the reflection of the mirror. His teammate had always been surprisingly vain. He grunted noncommittally and concentrated on his own reflection. The door clicked shut behind him. He listened to the soft footsteps fading down the hall. He could use a bath himself, he thought, surprised at how much sweat he could work up in that kabuki costume. First he needed to wipe off all the gunk.

Three firm knocks sounded at the door. "Yeah?" Jiraiya said. Tsunade's heart shaped faced appeared from behind the door.

"Good, you're decent. Where's Orochimaru?" She looked around the small room, her honey colored hair swinging from the pony tail high atop her head. She opened the door fully and stepped in, holding a small parcel in her hand. Jiraiya turned to smile at her.

"He decided to let us be alone," he waggled his eyebrows. He took a step forward only to be stopped by a single finger pushing back against his chest.

"Save it, this is important." She sat upon the western style bed with the uncomfortable mattresses that felt no softer than the wooden floor. "Our patron was very... pleased with Orochimaru. He is willing to give us a letter of introduction for when we arrive at our destination. This will make infiltrating the theater in question much easier. His only request is that he get to, eh hem, have a private evening with our little starlet."

Jiraiya paused. He waited for more, but Tsunade stared back at him, daring him to ask her any more questions. He felt a bubble of laughter threaten to escape his throat, followed by another and another until he was red in the cheeks and bent over, howling with laughter. "That tightass is gay for Orochimaru?" He gasped for breath, feeling the moisture beading at the corner of his eyes. Tsunade crossed her arms and glared at him, waiting for him to stop.

"It's not uncommon you know. Women used to perform until the prostitution got out of hand and they forbid them from the stage. I'm pretty sure that hasn't stopped the prostitution though." Jiraiya tried to calm down, but it was no use. His laughter died down, but a few more chuckles escaped. He wiped his eyes with the back of his hand.

"Oh man, wait til he hears this. You turned him down, right? There's no way we can make him sleep with that guy."

"Why not? Shinobi have given their bodies to worse." She crossed her arms over her chest.

Jiraiya's eyes dipped to the way her breasts bulged just slightly under the weight of her arms. He estimated she had grown to a D since he last evaluated her. One arm crossed over her chest and her wooden sandal jabbed his shin mercilessly. Jiraiya suppressed an unmanly show of pain, wincing just slightly under the assault.

"What was that for?" he scowled, rubbing the tender spot. If he couldn't dance in the next performance it would be entirely her fault, though he didn't regret ogling her for a moment.

She raised an eyebrow at him. "This is serious. We need to talk to Orochimaru. Where is he?" She pressed her lips firmly together.

"He's taking a bath, sheesh. I'll let him know what's up when he gets back and we can discuss this as a team. I can't believe you think he'll actually go through with this." Jiraiya turned his back to Tsunade and glanced back in the mirror. He grabbed a clean tissue and dipped it in oil before dabbing at a few spots he had missed.

"I know you want to protect him, but we have to let him decide. An evening invitation doesn't have to end up in the sack. He even sent a gift." Tsunade held up the package she had carried in. "See? Isn't that romantic?"

"What is it?" Jiraiya asked from the mirror. Tsunade tore through the paper, tossing aside a small note attached. She looked at a medium sized box and checked over it carefully.

"It doesn't look dangerous." She tugged on the lid and looked inside. "And it smells delicious." Jiraiya turned around and looked at the box Tsunade was lifting up towards him. Inside were six small treats shaped roughly like a flat cup. Jiraiya picked one up and sniffed it. The smell of cocoa was strong.

"He sent him chocolates? Where are the flowers?" He licked one tentatively and took a bite. Inside was a rich, nutty flavored filling. Jiraiya was pleasantly surprised by the taste and stuffed the whole thing in his mouth. "Not bad," he said, chewing the chocolaty treat. Tsunade looked away, scowling at him.

"Gross. Don't talk with your mouth full." Jiraiya figured that if there were six of them, Orochimaru wouldn't mind sharing. By his estimation, two of them were his.

"You want some?" He offered the box to Tsunade who only shook her head.

"I don't accept food from strangers. You never know what they put in there." Jiraiya shrugged and went for the slightly darker one. He bit it in half and noted the taste of this chocolate was more bitter.

"Your loss," he said. He smiled, deciding his count was up to three. Four, if he decided not to tell his teammate that Tsunade forfeit her share. "But yeah, as I said. Orochimaru isn't here. Want me to call you when he gets back?"

"Could you? And try not to be such a pig while you wait. For all you know, those could be laced with something." Jiraiya paused with the second half of the peanut butter cup in the air. His wide open mouthed closed and he looked at the half eaten candy a little more carefully. It looked normal to him. He threw the rest of it into his mouth. Tsunade rolled her eyes. "Don't tell me I didn't warn you," she smiled. "I'll be in my room." Tsunade stood up gracefully and stepped over Orochimaru's discarded undergarments on the floor. Jiraiya was about to go for the white chocolate, but paused. He looked up at his smiling teammate who was waving at him from the doorway and put down the box. Maybe she had a point. If he was violently ill later, he was blaming Orochimaru.

Jiraiya went back to cleaning up. He folded his Kabuki robes and placed them in their cover. They would be leaving the next morning. He made sure his equipment was in order and that his weapons would be well concealed. One never knew who they would meet on the road. He wiped his forehead with the back of his sleeve. so much exertion was making him feel warm. He picked up his roommate's discarded things and hung them up, smoothing out the wrinkles and ensuring the pressed folds wouldn't be wrinkled in the wrong way. He felt the first trickle of sweat slide down his back.

He began to change into his yukata when Orochimaru reentered the room. His long, straight black hair was back to it's natural state. Jiraiya tied his yukata shut. "Is it me, or is it hot in here?" Orochimaru paused. He looked around the room and shrugged.

"I feel fine. Maybe a bath will help." He pat his black hair with the white fluffy towel in his hands.

"I plan to take one. But before that," Jiraiya's eyes lit on the opened box of chocolate. He picked them up, "this is from your admirer. Tsunade tells me he's willing to give us a letter of recommendation for our target if you spend the evening with him." Orochimaru grabbed the box with one hand. He picked at the lid of the box and looked inside. He lifted out one of the white cups and gave it a sniff and then a cautionary lick.

"It's not poisoned," he declared, taking a small bite. "Did he say where?"

"What do you mean where?" Jiraiya put his hands on his hips.

Orochimaru sat on his bed calmly and crossed his legs. He bit off a chocolate edge, revealing the peanut butter filling inside. "Where does he want to meet?" Orochimaru said casually, taking another bite. He turned yellow eyes up at Jiraiya expectantly.

"You can't be serious. You plan to spend the night with that . . .?" Jiraiya made a face. "But he's a guy and you..." Jiraiya grimaced. "Don't tell me you can just give yourself to him."

Orochimaru's tongue flicked out to lick the peanut butter filling. He calmly waited for Jiraiya to finish his tirade. "I'm a shinobi. Who am I supposed to save myself for? If it helps the mission, I'll do it. Besides, he could be asking me to dinner. This doesn't mean I'll end up in his bed."

Jiraiya scowled and yanked away the box of chocolates. "But what if he expects you to? Are you willing to give away your first time to a complete stranger?" Jiraiya was feeling strangely irate. It shouldn't be any of his business, but this was his teammate and his best friend. Orochimaru tilted his head to the side. A serpent like smile splayed on his lips.

"Should I be saving myself for a friend? You think Tsunade will be willing to have me?" Jiraiya flinched. He had been flirting with her since he was 12 and she ignored him to this day. "Or is this your way of volunteering to be the first to break me in?" Jiraiya's face flushed. As much as he boasted, he'd only been with one girl and he felt incredibly awkward about it the next day and had never seen her since. He was no one to boast of anything special his first time around and yet here he was lecturing his best friend on what a bad idea it was to give himself to a stranger. Or maybe it was because of his experience that he decided to.

"You talk about this as if our benefactor is the predator here. Did it ever occur to you that it might be the other way around?" Orochimaru uncrossed his legs. His yukata was loosely tied and split up the middle, revealing his smooth pale thigh. "I think you underestimate me, my good friend," Orochimaru rose to his feet, stalking forward while his tongue took another swipe of the treat in his hand. "The white ones are delicious by the way. Have you tried them?" Jiraiya took a few steps back and shook his head vigorously. "You really should." Orochimaru was suddenly invading his personal space and holding up a half eaten peanut butter cup to Jiraiya's lips. "Say ah." Jiraiya's knees hit his bed and he flopped down. Orochimaru bent over him, practically feeding him the chocolate. Jiraiya looked him in the eye cautiously and took a bite. "Delicious, isn't it," Orochimaru whispered. Jiraiya could feel his hot breath. Jiraiya accepted the rest of the chocolate being pressed into his mouth. He nodded slowly. He could feel the flush in his cheeks spreading to his throat and his chest, and something below his waist was starting to become very interested in the pale smooth skin on view from between two wide open folds of green cotton. Orochimaru was straddling his lap.

Jiraiya tried not to touch the milky inner thighs now pressing against his legs. "Would it put you at ease if I told you it wouldn't be my first time?" Jiraiya looked up with a start. Orochimaru had never talked about his private life and had never mentioned any sort of romantic trysts. Jiraiya had practically knocked his door down after his first time.

"You never..."

Orochimaru placed a finger against his lips.

"I guess that's a no. I was hoping that if I lied about it, you'd stop over reacting." The one finger slid down his lips, to his throat and down to the edge of his yukata. A little tug was all it took to reveal a little more of his chest. "It would be my first time, but that wouldn't bother me, to be honest. I'd rather have my first time mean something. And if it can't be an emotional sort of meaningful, than a good cause will suffice." Jiraiya placed his hands on Orochimaru's hips to pause the slight scuffles that had started to make him very uncomfortable.

"You don't mean that." Jiraiya said, looking into golden eyes and wishing for a moment that his friend would stop playing this silly game and listen to him.

The smile faded and the vixen like creature a moment ago relaxed into the calm expression he was more accustomed to. "And maybe the man I was saving myself for isn't waiting for me. Maybe he ran out and gave himself to a stranger." Orochimaru freed himself and gracefully stepped away. He straightened out his yukata and turned his back to Jiraiya with the flip of his hair. "I'll go talk to Tsunade and tell her I consent. Don't wait up for me."

Jiraiya watched, frozen on his bed while the words sunk in. When the door creaked open, he woke, as if from a dream, and dashed onto his feet. He caught Orochimaru by a hand, pulling him back and turning him. The slighter man collided into him, thudding against his chest. Jiraiya wrapped his slim frame with both his arms and held him tight.

"I'm sorry. I. . . never noticed. I've been a lousy best friend."

"Among other things," Orochimaru said acidly. He didn't resist Jiraiya's hug, caught up limply like a rag doll. "Does this mean you're not letting me out?"

"You'd kick my ass if I didn't." Jiraiya pressed his nose to the black locks and inhaled the sweet scent of his shampoo. "If you want to go tonight, there's no one who can stop you. Only..."

Orochimaru pressed his cheek against Jiraiya's chest. "Only?" he prompted. His right hand touched Jiraiya's waist tentatively.

Jiraiya tried to think of something romantic to say; something meaningful that would convince him to give up and listen to what he was trying gto say. If only he could figure out what he was trying to say.

"Take care of yourself tonight," he said lamely. Jiraiya's fingers trailed down Orochimaru's arm, already trying to apologize for his lack of smooth words. "Maybe that oaf was stupid enough to give away his first time, but maybe it's because he was waiting too, and maybe he thought that the ones that really mattered to him were the last ones who would accept him."

Orochimaru was quiet for a moment, for a long moment that Jiraiya felt was quickly becoming uncomfortable. And then a familiar gravelly laugh reverberated against his chest.

"Sometimes, you're such a girl," Orochimaru said. He pushed Jiraiya away and stepped towards the door. Jiraiya huffed and looked away, crossing his arms petulantly.

"At least I don't look like one," he said childishly. Orochimaru stopped at the doorway and smiled.

"Thank you, Jiraiya," he said. "But you shouldn't wait up for me. And well, if you're still awake when I return, well then..." He paused and looked at the floor. "I guess we'll cross that bridge when we get there."

His angular profile disappeared behind the worn wooden door. Jiraiya waited for something else to happen, but when it didn't he collapsed onto his bed and let out a big sigh. He couldn't tell whether it was relief or disappointment. He couldn't tell a lot about what he was feeling right now.

Jiraiya stretched out on his uncomfortable bed and looked up at the panels of brown wood lining the ceiling. He thought about taking a bath and he thought about finding Tsunade and making her convince Orochimaru that this was a bad idea. And he thought about Orochimaru's fingers on his lips, feeding him the treat that had been in his own mouth just moments before.

He wouldn't be able to sleep if he tried.

And while he pondered his teammate's words and the bitterness at Jiraiya for losing his virginity first, he had a feeling that it wouldn't matter so much after today. And while he technically had already squandered away his "first," he had a feeling that he'd experience a very different sort of "first" tonight.