He goes straight for the ass.

Naruto watched as Shizune eagerly shook her rear at him, and decided he couldn't pass up fucking that ass. So he took the Note again and wrote in the same adjustments he had used previously, this time for Shizune.

Shizune felt a strange sensation in her rectum as it was changed by the Note, but ignored it for now. "Come on, come fuck me," she teased him in a sultry manner.

"Oh I will," he grinned, walking up behind her, stroking his cock as he rubbed her butt cheek, and moved his dick to her back door.

"Eh!? You're using that hole?" she asked, surprised, but didn't move away.

"Of course, it's too good to pass up," he remarked, before pressing at it.

"Ah... Okay, sure," she agreed, her eagerness for Naruto to fuck her heavily outweighing her apprehension. She lightly pressed back to help him in, before moaning as her anal ring parted to slowly grant him access.

He pressed into her tight butt, grinning as he soon bottomed out, before reaching to caress and grip her side before he began to fuck her.

https://rule34.xyz/files/3108/3108536_preview.jpg

"Ah, oh Naruto, yes, fuck my ass!" Shizune murmured as she felt intense pleasure without pain as he worked. "It feels so good!"

"Good to hear," he grinned, speeding up as he glanced back to see Tsunade and the Shadow Clone still in place, the clone taking it slow and fingering Tsunade, which Tsunade wasn't complaining about, since it kept his cock where she wanted it even longer.

He then returned his full attention to Shizune, pounding at full speed while she grit her teeth, and clenched the fabric of the couch. "How... How does anal sex feel this good?" she murmured, her ass tightly gripping his cock, essentially milking it.

"If it didn't, it wouldn't even be a thing," Naruto joked though his groans, before he gave a loud one, and came, filling up Shizune's ass. Shizune screamed as her orgasm hit as well, and Naruto came a second time as his clone had came and dispelled. Tsunade sighed, rubbing her tits and already missing the cock between them again.

Naruto wheezed a bit before pulling out, considering what he should do next.