Sometimes, Jiraiya drags him out of the village and pretends he wants to pass on more of his techniques. Naruto always complains -- he doesn't like to let his team hang with little to no warning, and Jiraiya only wants him around so he can raid Naruto's wallet on his alcohol-and-whores binges anyway -- but he always follows.
One, because the techniques and training may be brutal, but they give results, and Naruto has never been afraid of doing what needs to be done, no matter the risks, in order to get stronger.
Two, because if the Akatsuki are coming after him again, he'd rather they didn't catch up in the middle of Konoha. Or worse, with Sakura-chan and Kakashi-sensei and Sasuke caught in the crossfire.
Especially Sakura, because she wouldn't have a fighting chance. Especially Sasuke, because he'd lose it again and Naruto has had it up there with punching holes through his best friend.
Kakashi can hold his own. He's immortal, really.
Three, because, alright, he likes to travel, but he's not going to get the chance to chat up a scantily-clad woman with Kakashi-sensei and Sakura-chan around. Those damned perverted books are brainbreaking enough; Naruto refuses to imagine Kakashi bringing his team to a red-lantern district unless it directly involves a mission -- not, as Jiraiya does, unless it somewhat meanders a few streets beyond said district and they're really not into that much of a hurry, are they. (Jiraiya has a somewhat elastic sense of planned routes and timeframes; Naruto doesn't mind as much as he pretends to.) And he can't have Sakura-chan there because, well ... Yeah.
As for Sasuke, he'd probably just scoff and wait for Naruto elsewhere, so his presence wouldn't make much of a difference.
Anyway, those trips aren't so bad, and at least they let him see more of the outside world.
And more of the outside people, too.
The person he's chatting up is a young woman, not a girl; she has clear brown hair and eyes -- and eyes. Well, he's fairly sure she has eyes. He isn't sure of their color. He could still pinpoint the beauty spot between and just a little over her left breast even if she decided to put on a parka right now. It's that tantalizing.
Well, okay, she's the one chatting him up. He's a bit tongue-tied. Just a bit. Having a soft, delicate hand with manicured nails traveling up and down his chest might explain it.
He follows on her heels like she has him by the balls, which she does, figuratively. The second they're in a booth out of direct sight of the bar, the hold becomes very much non-figurative.
She lets him find out if that beauty spot tastes different from the rest of her skin.
He leaves the bar dazed, pleased, and with a whole new appreciation for the firm pressure of a thumb. Jiraiya is ranting up a storm about Naruto's woman getting added to his tab; but seeing as Naruto's wallet is still flat from the last old pervert's raid, he isn't too concerned.
Next time they stay at a brothel perhaps he'll make Jiraiya shell out for a geisha.
Nope, Naruto never manages to get that geisha. Yeah, it's really not a lot of real life experience. But Kyuubi's memories and his own imagination more than compensate for it. XD
It amuses me so much that Sakura was the only one of the three who ever
had sex before they shacked up. u.u