Tsunade did say to do what he says

"O-okay..."

Blushing profusely, Hinata slowly unzipped her jacket, thankful that no one was paying any attention to her...yet. She handed it over reluctantly to Jiraiya. Though her blue undershirt covered everything and was very modest, Hinata didn't think it was quite enough and hated how much less of her body it hid compared to her jacket. She stopped moving now, not wanting to remove anything else.

Jiraiya smirked. "Come on now toots, sooner you're as naked as the day you were born, the sooner we can get going. I've got a few places we need to stop at before you can get your clothes back."

"A f-few places? While I'm naked?!" Hinata asked quietly, pulling her arms in front of her chest defensively.

"Yep, now let's hurry it up!" He eagerly urged her on.

Hinata stuttered, "B-but I can't get naked! I've never done anything like that before! W-we're in a crowded street, everyone will see me!"

Jiraiya sighed but smiled. He began to walk away. "Tsunade wasn't kidding when she said you were shy. Follow me."

Though not really liking Jiraiya so far, he did have her jacket, so Hinata followed. Hinata doubted he was really wanting to help her confidence issue. He was likely just wanting to see her naked. Her doubts about him doubled as he led her into an alleyway.

"There, now we're not in public, now strip!" He looked proud.

Normally, there was no way Hinata would willingly take off her shirt outside the privacy of her bedroom, Lady Tsunade did say to do what the old man said, so there she was with only a humble purple bra and a crimson blush that traveled to her belly button concealing her chest. Hinata held her shirt over her bra, deeply uncomfortable with the whole ordeal; but Jiraiya was, to his credit (and on Tsunade's strict orders), giving her plenty of person space.

"Go on, take off the bra, let's see what I have to work with." Jiraiya demanded thirstily, his face also red.

Hinata shook her head and instead shuffled out of her shoes and baggy pants, discarding her shirt on the ground. Far from scanty, her panties were white and cotton (Of course they were lol) and her ass was well covered. Her long legs were pale and hairless. Hinata stepped out of her pants and moved a hand in front of her scarcely covered crotch. No one else had seen her in so little clothing since she was small enough for her father to help bathe. If Jiraiya got his way though, that would change very soon. She couldn't help but back away as Jiraiya stepped towards her. He scooped up her clothes and moved back.

"W-wait! Where are you taking those!?" Hinata asked, mortified.

Jiraiya pulled out the giant scroll on his back before answering, likely for dramatic effect. "You'll see." He set it down and opened it. In a flash he bit his thumb and preformed the summoning jutsu. A puff of smoke later and a large red toad with goggles sitting around his neck sat there, facing the pair.

"Eeek!" Hinata yelped as another, although admittedly not human, pair of eyes saw her in her underwear. She ducked down into an embarrassed ball as the toad ignored her and turned to Jiraiya.

"What do you need? I was busy." The frog asked impatiently in a croaky voice (lol pun).

"Eh?!" Jiraiya exclaimed, "I meant to call Gerotora over, I need him to seal some things for me."

"He's busy, what do you need to seal? Doesn't seem to be a battle going on here."

"No no, I'm looking to seal this brat's, " He pointed to Hinata with his thumb, "clothes for the day while we ran some errands."

The toad turned and took a proper look at Hinata for the first time. "Not even going to ask way. I'll take them with me because I'm in a rush, but she's still wearing some, does she need to get rid of those as well?"

Jiraiya smirked. "We were just doing that actually. Hinata, let's get rid of that pesky underwear now."

Hinata looked up from her ball with wide eyes. He was going to seal her clothes?! She'd be trapped without any clothes all day until Jiraiya decided she could get dressed again! No way could that happen! Both the toad and the pervy sage were looking at her expectantly.

"Come on brat, I gotta get back!" the toad demanded rudely.