Sakura's training progresses

Unaware of the events on the other side of the city, Naruto solely focused on preparing Sakura for her very first time to have a mans penis slide into her. Not her pussy, unfortunately, but Naruto was content with her shapely butt.

He was still getting lost in the moans Sakura was by now letting out as Naruto licked her forbidden hole, the tight entrance now glistening with his saliva. So, he decided to step it up a little bit. To loosen her up a little bit, Naruto began to prod the tight hole with his index finger. Instantly, he felt how Sakura clenched up at the intruding digit.

Naruto sighed. Like this, it wouldn't work out. "Try and relax a bit, Sakura-chan. I won't hurt you, I promise.", he told her in a warm voice that would hopefully have the desire effect.

Although her voice trembled, his teammate answered. "O-Okay...", Sakura said. She was by now fully trusting Naruto, so she did her best to comply.

Naruto indeed found that, even though she still clenched up now and then, she was doing her best to accept the invading finger. Naruto tried and suceeded in slowly, very slowly, inserting his finger into Sakuras ass. It was only bit by bit and he stopped whenever she involuntarily clenched up too much, but eventually, he had his whole finger inside of Sakura.

Still, he knew that Sakura would be in trouble if she didn't manage to fully relax. "You gotta relax more, Sakura-chan, else my dick won't be going to fit at all later on...", he told her truthfully.

"L-Later on? So you're telling me... this isn't...?", Sakura gasped in disbelief. Apparently she had mistaken Narutos finger for his penis. She turned around and Naruto saw her eyes were wide open. "

Naruto leaned forward and kissed the pinkette tenderly. Hesitant at first, Sakura responded to the kiss, all the while Narutos finger was still inside of Sakura. There, he felt how her sphincter relaxed the more they kissed. Evidently, Sakura relaxed like this when they kissed.

He figured that it could work like this. So, he raised his hips and withdrew his finger, only to replace it with the tip of his dick that now began prodding on Sakuras backdoor. He actually did manage to slowly and carefully slide the tip of it into Sakura, before she had fully realized that now his big cock was demanding entry to her ass and consequently began to clench up.

"It's so big... b-be gentle, alright?", Sakura asked of him, her voice fearful and anxious. She knew she was doing this for Sasuke, but she was justifiably scared of what would happen. But, she tried to have some more faith in Naruto here...

His urges however screamed at him to finally ram himself fully inside this heavenly tight hole he was about to enter. They way it clenched onto him, almost massaging the head of his dick... he could hardly wait to have that feeling on his whole dick.