A/N: Remember you can always find me and see even more of my content, and see it earlier than anywhere else, over by a certain site that rhymes with Rate On, or a site known for its rather questionable questing practices, under the same name, or at the blue bird place, NOTTHISWAYQQ~

Lipstick missions were... a thing.

The so called lipstick mission was a simple thing indeed. Dress up as girls, sneak into a nobleman's home, steal his secrets. Lipstick only because of the fact that they'd have to potentially sleep with the client to get the secrets. In this case, lipstick was particularly fitting, Sakura mused, as she finished applying the lipstick on Sasuke's lips, then showing him the lip motion to make sure it was applied and distributed evenly. Sasuke's lips met in a near perfect imitation of her own movements, and then without a popping sound, opened again, showing that the slightly pink tone that would make his lips look bigger was properly distributed, applied and matched on both upper and lower lips.

Nodding at her handiwork, and seeing that all the makeup was properly applied, his lashes were nice and fluttery, his lids were painted, his cheeks had the proper amount of blush, the liner was making his dark eyes pop... everything was perfect.

"Are you guys ready?" Naruto asked, walking into the room. "You're not even dressed yet? How are you so slow!"

He cocked his hip, putting a hand on it, striking a pose to show off. He wore a short kimono, open at the middle, in soft orange, with a red obi tied at his waist, that was loose enough to allow it to split above his waist. At chest level, Sakura noticed he wore a red, lacy bra, and as Naruto stood in such a way, the lower part of his kimono split as well, showing the similarly frilly red panties that covered his small bulge.

With hair lengthened thanks to a jutsu that Naruto had somehow learned in literal minutes from the Third Hokage despite neither Sakura nor Sasuke being able to pick it up, Naruto looked genuinely like a very cute girl. His makeup was less prominent, but then, he needed less, already having a more rounded face with softer features, a cute charming feature in his whisker marks, and eyecatchingly beautiful blue eyes. Honestly, Sakura was almost glad Naruto was a boy - because this was proving that if he'd been a girl, absolutely nobody would've stood a chance at getting Sasuke's attention over him. Her. Whatever.

Sasuke, for his part, was almost managing to not blush at the sight of their blond teammate.

"How are you so good at crossdressing?" he asked, trying to mask him checking out his fellow teammate.

"This?" Naruto asked, adjusting his outfit to make sure it covered him up properly. The Kimono only came down to mid thigh, it was deliberately designed to be sexy, not practical. "There was this old lady whose entire family passed away in the building," he explained, "and apparently her granddaughter looked like me so I spent a lot of time trading cookies for time spent playing dressup. Learned all sorts of things too," he explained. "Best cookies in the world, I'll miss that old lady."

"She died?" Sakura asked.

"No, just moved to the capital," Naruto said. "Anyway- are you guys at least close to done?"

"We still have five hours until we have to leave," Sakura countered. "We're taking our time to make sure we get it right on the first time."

Naruto rolled his eyes. "Okay, fine," he said. "Have you picked an outfit yet?"

Sakura shook her head. "Not really. I'm really easy - I've got this one dress I can wear," she explained, "But as for Sasuke..."

"I think we're close to the same size, I've got some I could lend him," Naruto said.

"Why do you own girls' clothes?" Sasuke asked.

"So I can crossdress wearing them, duh," Naruto said.

Sasuke's eyes wandered down, then back up. "Even the panties?"

Naruto shrugged. "You think I dress like this and don't flash at least a little?" he asked. "Seriously, half the fun is the reactions when people find out I'm a boy. In fact, get dressed, we're going out, I'm going to show you how awesome it is to trick idiots into questioning their sexuality!"

Sakura opened her mouth, then stopped, then thought again, and finally... "Naruto, I'm a girl."

"I know that," Naruto said, "buuut, you can just wear a chastity cage, and it'll look like you've got a penis under your panties," he explained.

"You own a chastity cage," Sasuke said flatly, almost as if he wasn't even surprised.

"Correction, I own several," Naruto said.

"How? Why?" he asked.

"Where do you think all the money I use to pay for my pranks supplies and for repairs and cleaning after I'm done comes from?"

"Wait, you pay for the repairs and cleaning?" Sakura asked.

"'course I do. You think I'm some sort of asshole or something?" Naruto asked. "Anyway, I got this modeling contract for all sorts of cute clothes and toys," he explained. "Just gotta take a couple of pictures and they even let me keep a lot of the toys and clothes. Haven't had to buy sexy undies ever thanks to that."

"I don't even," Sakura shook her head.

Naruto made a handsign, and a clothe popped out.

The clone gave Naruto a salacious grin, which the original answered, then they made fingerguns at each other. "Lookin' good!" they chorused, giggled, and then the clone took off running.

"That was weird," Sasuke said. "But-"

And then the clone was back. Right, they were in his apartment building, silly them for thinking that'd take longer.

The clone then tossed a small bundle at Sasuke and popped.

Naruto hummed. "Put those on," he explained. "Sakura, can you help?"

The two of them converged on Sasuke, and after a few moments, he was ready.

First was the panties, slid up his slim legs. They were white, and rather on the smaller side - barely managing to cover Sasuke's admittedly rather sizable junk. Then was the garter belt, same immaculate white as the panties, set to rest above his hips. He didn't quite have the hip flare of a woman, but exercise had given him a nicely shaped bum, and his slim physique gave him enough of a shape to wear the garter belt.

The stockings were next, transparent white. His legs were not quite his best aspect, but they were nice, smooth and well shaped. "That was a great choice," Sakura said, "it really brings out his general dark look," she admitted.

"I know right?" Naruto said. tying the stockings to the garter belt with the straps. The bra was next - much like the one Naruto himself was wearing, Sasuke's would help disguise his chest's shape just a little, without actually being padded. Deceitful, but not truly lying.

And last came the dress, a black and white gothic lolita style dress that took a little bit of trying to put on.

"Looks better with pigtails," Naruto mused, but Sasuke didn't have long enough hair, so instead, they just gave him a messy ponytail, a little bit spiky, to go with the accessories - a spiked wristband here, a collar with a skull tag, an earring with a hanging kunai, and even an anklet with a skull badge on it.

"Why do you own all of this stuff?" Sakura asked. "And why don't you wear it more often? You'd look great in it."

"I should show you one of my calendars some day," Naruto said with a giggle. "Swimsuits or lingerie, which one would you prefer?"

"Both?" Sakura asked.

"Both is good," Naruto agreed.

Sasuke grunted. "Are we done?"

Naruto gave him a nod and a thumbs up. "Cute as a button! Gonna have to drop that tough guy act and let out your natural voice, though."

Sasuke sighed. "Fine," he said, in a voice significantly higher pitched than the one he usually spoke with. The one that only came up when he was hit, highly stressed or otherwise unable to keep his cool. "Better?" he asked.

"Perfect!" Naruto said. His own voice was higher pitch than most, a bit lower than most girls, but given that there was no puberty on sight for him right now, he sounded indistinguishable from a real girl. In fact, he sounded girlier than Sakura herself did sometimes.

"Aw, man, you're so cute it's a shame you don't do this sort of stuff more often," Naruto lamented.

There was a moment of silence.

Then another.

"This..., is not as uncomfortable as I expected," Sasuke finally admitted. "Though the panties are... a bit constricting."

"Aren't your balls getting crushed?" Sakura asked.

Naruto hummed. "Well mine is really small so I've never had to deal with that," he said, shrugging, then got down on his knees and lifted Sasuke's skirt. "Oh, I see the problem now."

Sasuke's face was bright red.

Sakura looked down and- "Oh wow," she said, blinking. Now THAT was the true blessing of the Uchiha clan!

Naruto licked his lips. "Well, that's gonna make it difficult," he hummed, "alright, we'll deal with this quickly and go pick up some guys at a bar and squeeze them for all they're worth."

"Wha-"

Both of the other members of Team 7 only had a moment of shock before Naruto raised Sasuke's dress a little more and just- took the erect penis into his mouth, like it was nothing. He even made an enticingly lewd sound, letting out a moan and swallowing around Sasuke's cock. Sasuke's own moan came a moment later, and as if by instinct, grabbed onto the dress.

"Naruto what are you doing!?" Sakura protested.

Naruto pulled back. "Making him cum so it goes down?" he asked. "Come on, Sakura," he said, rolling his eyes.

"How- why- what-"

"Seriously, I told you- I did all sorts of photoshoots, people get hard and it's difficult to work like that," he said.

Sakura frowned.

She could already imagine it, Naruto, on his knees before a sitting cameraman, getting patted in the head and told he's a good boy as he faithfully services that thick meat rod.

Just like he did to Sasuke then, pulling back, licking it all over, lavishing it with love and attention from his tongue, covering it in saliva, licking up every droplet of cum, moaning wantonly and perversely as he did, before taking the tip back into his mouth, using his hands to pump the slick, wet shaft, and then bobbing his head in unison with the strokes, working his partner's shaft until the dark haired boy's moans mounted, and his pleasure reached its peak.

Sakura realized her hand was teasing her own - naked - pussy as she watched Sasuke blow his load down Naruto's throat, the bond swallowing quickly and easily, like he was experienced, it was definitely not his first blowjob.

Sakura patted his head, with the hand that wasn't touching herself. "That's it, good boy," she mused, as she imagined the workers at the shoots did.

Naruto giggled. "That feels nice," he said. "Anyway with that done, we can-"

Except... Sasuke was still hard. Throbbingly hard. And panting. "More, I need more," he said, "this is... nowhere near enough," he said.

"O-Oh," Naruto blinked. "Uhm... I have an idea, it might help you get off easier..."

Naruto's own free hand struck a handsign, and in a flash and a puff of smoke, a blurring figure dashed away, and in a few seconds, came back. The clone of Naruto, looking a bit disheveled, gave Sakura something and then disappeared.

It was a- a strange set of underwear. With a rod at what she imagined was the front, which poked out a little on one end, and a lot more on the other. Both ends were tipped with familiarly phallic shapes. "Is this-"

Naruto nodded. "Shorter end goes in you," he said.

"Let me guess, another video?" Sakura asked.

"This one? No, this is the one I use with big sis Ayame when she's stressed," he said. "She loves to choke me on it or just ream my butt," he explained.

"I won't even question it," Sakura said.

"Hurry!" Sasuke said. "I want more," he needily insisted.

Naruto hummed. "Right, right, come on big boy," he said, hiking up his kimono, revealing his thong-clad ass, which he quickly pulled down, exposing his tightly puckered, deliciously amazing looking butthole. Sakura licked her lips and swallowed.

"I'm not gay," Sasuke said, frowning.

Naruto giggled, wiggling his butt. "Please fuck my ass~!" he moaned. "Come on, come on," he begged, "put that big dick of yours right in my ass, and fuck me raw, give it to me nice and hard~!"

Sakura realized she was turned on to high hell when she realized she was fucking herself with the strap on - not even knowing when she'd slipped it on. She saw Sasuke slowly losing his mind, hands gripping Naruto's hips, then coming back to raise his own dress, and with the hem of it held by his teeth, the last of the Uchiha growled as he lined his large cock up with the tight ass of his teammate.

Now finished, Sakura adjusted the strap on dildo one last time... and only then noticed that the clone hadn't actually disappeared.

"What are you-" Sakura began, as the clone got on its knees before her.

The blond's grin was a bit distractingly charming, then he began giving her a ridiculously messy, wet and sloppy blowjob. "Going in dry hurts," he said, "I've got this lubricant," he said, gesturing at a bottle he held in his hands, "tastes great and feels better," he said, as he poured some more in his mouth, and then returned to the blowjob. Sakura moaned, not really feeling more than the pulling and pushing of the dildo, but the image was giving her even stronger pleasures than that. Naruto was really cute, she realized, and she wished she'd seen more of this side of him than the class clown.

She turned when she heard Sasuke's long and drawn out moan, accompanied by NAruto crowing in victory. Sasuke had penetrated the blond... and lost control, now pounding his rival's ass with all his might. Both of the boys were letting out girlishly cute moans, as they pleasured each other.

The clone finished the job, and winked at Sakura. "Go give that bastard a taste of his own medicine !" the clone said, gesturing at Sasuke's behind.

Both moved, and soon, the clone was holding Sasuke in place while Sakura raised his skirt and spread his asscheeks.

"S-Sakura, wha-"

And then Sakura was in, thanks to the lubricant, the dildo slid in smoothyl up Sasuke's ass, his excitement and flexibility easily allowing her in. The boy didn't even try to resist, and now all three together, as a team, began a dance as old as time itself, with some new toys and additions.

Sakura moaned lustfully, pounding Sasuke even harder than he was pounding Naruto, the slap of skin on skin, the crescendo of moans from the three of them, the smell of arousal and excitement, all of it was driving the three of them towards ecstasy.

Sakura even spied Naruto's clone grabbing the original's head, and shoving his cute little prick down his own throat. Well, probably didn't go that far, but Sakura could only wonder how delicious that was.

Thoughts ofr later, for now, she was consumed with the sheer beauty of Sasuke's panty clad ass, the white panties moved to the side as she pounded him, chasing the high of their orgasm.

It didn't take long, they were melting together into an amalgam of lust and pleasure, and the first to crack was the meat of the sandwich, Sasuke screaming out his orgams as he tightened up on the dildo, SAkura feeling the pressure almost through it. Second was the pink haired girl herself, one final thrust into Sasuke's suddenly tighter ass causing the dildo to hit exactly the right spot at exactly the right time to burst the bubble of pleasure and flood her with it, every nerve lighting on fire.

Both of them crashed on top of Naruto, and it seemed that being flooded with Sasuke's own seed was ultimately enough to overcome the blond's own resistance, as he sprayed an incredibly large amount of ridiculously thick seed on the floor under him, panting as he fell to the side of it, cumming some more, being spooned by Sasuke, still hard and throbbing inside his ass.

Naruto giggled. "A tough customer, huh," he said. Sakura laughed, rolling herself, allowing Sasuke to roll on his back, slipping out of Naruto's ass in the process, his stiff prick, covered in semen and what appeared to be lubricant, proudly standing up, a bit redder than before but still clearly good to go.

Sakura looked at Naruto, who nodded at her... and then she smirked. The series of straps that made up the 'panties' part of the strap on didn't cover her anus. And so she went and sat on Sasuke's dick, slipping the lubed up cock up her bum, moaning wantonly, enjoying herself immensely, as she did.

With a grin, Sakura realized Naruto wasn't still either. He straddled Sasuke's face, and the other boy, seemingly in a daze, just accepted Naruto's cock, suckling on it almost like a baby, when Naruto put it in his mouth. The blond leaned forward and began licking at where Sasuke and Sakura were connected. making a show of sucking the plastic cock before dipping back to lick at Sakura's taint and Sasuke's stiff dick.

By the time it was time to go to do the mission they were crossdressing for, all thoughts of going out were gone from their minds, satisfied with how they'd spent their time 'rehearsing' and training for their work later. And if they were a lot more willing to choose the route where they got paid more and got more info from the client through softer means... well, that was Team 7's business and their business alone.