In her pussy, then her ass.

Naruto sighed in pleasure as his cock sank into Sakura's wet folds, making her moan out loudly herself. "Ah... Master..." She had her eyes tightly shut, and some discomfort on her face.

"How do you feel?" he asked her, almost halfway in.

"It hurts a bit... But please keep going, I want you to feel good..." she said.

Hmm, that wouldn't do, the point was for them both to feel good, even if it was hot that Sakura prioritized him. Sakura was clearly a virgin, meaning her hymen wasn't quite used to sex. It wasn't a barrier the way most people thought of it, otherwise, where would their periods go, something Naruto knew because of one of Pervy Sage's many, many lectures on women he hadn't wanted to hear, but it would still very easily tear.

Staying where he was for the moment, Naruto made a clone to grab the Note and decided to test the physical changes by writing, "Sakura Haruno's hymen will lose all pain receptors and feel pleasure instead and will be hard to tear via sex."

After the clone dispelled, Naruto resumed, and Sakura gasped as the pain abruptly vanished, and the pleasure she felt increased. "Oh, Master, I don't know what exactly you did, but that feels so good!"

He grinned, gripping her ass cheeks, and said, "Good." He was fully bottomed out in her now. "Are you ready?"

Sakura eagerly nodded. "Yes please Master, fuck me!" Naruto obliged, pulling out and thrusting right back in, making Sakura shriek and throw her head back.

He ran his hands up her back as he began to settle into a rhythm of fucking her. She cooed with every thrust, feeling amazing and loving the fact that Naruto was enjoying himself as well.

He then leaned over her and fondled her boobs, making her moan even more as he got more frantic. "Sakura, I'm gonna..." he grit his teeth, before shooting his load into her pussy, bringing her to orgasm as well, and making her scream. Really, it was a good thing the Third Hokage had bought Naruto this whole apartment complex, sure, he was lonely, but not only did he have a place to live, even if it was poorly maintained due to him being host of the Nine Tails, and a good amount of privacy. Else he'd have angry neighbors at his door right now.

He pulled out as Sakura collapsed a little, and he looked at his shaft, which was softening a bit, but then he looked at her still raised butt and smirked as he realized that he could fuck her ass now, and the thought, along with his Uzumaki stamina, immediately reinvigorated him, and he made another clone to write in the Note to make her anal opening tougher and more erotically sensitive.

Sakura moaned as she felt her asshole tingle a little as it was changed, and paused as she felt Naruto put his hands on her butt and spread her ass cheeks. "Master... What... OHMYGOD!" she cried out with surprise and pleasure as he plunged his slick cock right into her tight hole. "Oh yes Master, use my ass!" she cried out, her tongue lolling out as her eyes rolled up in her sockets.

Naruto grunted and grinned as he had to exert a bit to fuck Sakura's ass with how tight it was, but that made it all the more pleasurable. He managed a decent pace as he once again leaned forward to grab her boobs, but this time, sat back, pulling Sakura into a sitting position on his lap with his cock still in her ass as well, making her yelp in surprise.

However, she quickly got the idea, and braced her back on his chest, and placed her hands and feet on the floor, and began to work herself on him, throwing her head back. He leaned down and kissed her, extending his tongue into her mouth and she unconsciously returned the favor, soon simply running their tongues along each other just outside of their mouths.

Naruto squeezed her little tits, making her moan again, and she kept pounding her ass up and down in him, before he finally grunted and spewed his seed into her ass. She collapsed completely after cumming from that, and wheezed on the floor.

Naruto joined her, even he was exhausted now. They laid next to each other, Naruto spooning Sakura, for about ten minutes before Sakura got up to use his shower. Naruto sat up, and just as she came out, he had a scary thought. "Hey... You on the pill or anything?" he asked.

"Don't worry, Medical Ninjutsu has a contraceptive jutsu in it Master," Sakura smiled. "I used it in the shower. Might want a condom for non medics though, assuming you plan to use that Note on others..."

"Wait, you wouldn't mind that?" Naruto asked.

"Of course not Master, I'm just your sex ****, not your girlfriend," Sakura teased, posing her nude body for him. "Basically, we're friends with benefits, albeit I'm a subservient friend in bed, where you are my Master... But you are still an idiot everywhere else," she teased, sticking her tongue out at him.

Naruto chuckled. This was great, he could still maintain his friendships while having his fun with the girls on the side. "Still, I don't think I will need a condom, I just need to use the Note to make myself only fire blanks unless I intend otherwise..."

"Good idea Master," Sakura smiled. "Well then, I should get dressed and head home," she added, sounding ****, but at Naruto's nod, she put her clothes back on, and on her way out, she smiled and said, "Have a nice night, and welcome back Naruto." With that, she was gone for the night.