Some advice would be good right about now... //Private. Possible chocolate milk?//

"You be the judge. I'd say yes, though." he grinned.

"Get over here and ride my dick, kid," Jiraiya leered at him.

"Front to front, or back to front?" he asked with a crooked smile as he sauntered over.

"Depends.. D'ya want me to be all nice to you, or spank your little ass while you fuck yourself on my cock?"

"I'll be nice and let you decide. I'm up for both options." he grinned.

"Spanking it is.. come on, let me see my dick split your ass when you sit on it.. if you can take it," grinned Jiraiya.

A small grin, and he turned around, positioned himself, and then... slowly slid down over Jiraiya's proud erection, a small gasp escaping him when he was spread wide.

"Ah, fuck, kid," grunted Jiraiya. "You're.. tighter than that Shiranui kid. Goddammit..."

"I don't... Normally bottom. That's... why..." he managed, rather breathlessly as he sunk even lower, moaning with the sting of pain making itself known.

"Cmon. Ride that dick. You know you like it. You know you wanna feel a real man taking you good," Jiraiya encouraged. "You don't bottom because I'm the only one man enough for you.."

"Think you got that about right..." a weak grin, then he did begin establishing a rhythm, slow at first, getting used to the sensation of being filled once more, so long after the last time... But soon it quickened as he got used to the sting, small groans slipping from his thin lips.

"Ahhh, yeah.." Jiraiya moaned into his neck. "Daaamn, you feel tight as a virgin... that's a great ass you got, kid..."

"Heh... You're not feeling too bad, either." the usual smirk in place, a teasing look in his eye when he glanced over his shoulder, squeezing him to prove the point, and moaning when the feeling of Jiraiya filling him up increased with his squeezing.

A small grunt was all he coaxed out of the big man, who frowned and slapped Kakashi's ass. "You gettin' cocky, kid?"

A small groan with the light sting. "Aren't I always?"

"Yeah." The next slap landed on his thigh. "Now work that ass like you mean it."

Another grin, and a weak moan, then he began, again at the slow pace at first, but soon faster, harder than before.

Jiraiya just sat there and took it, occasionally letting out a small grunt in reward for a particular effort.

Before long, he was writhing his hips this way and that, both for Jiraiya's pleasure, and or his own, trying to find that perfect spot.

"Dammit, kid, don't you know where your own prostate is?" Jiraiya laughed against Kakashi's neck, making sure the puffs of breath hit the young man in nice spots.

A small shiver ran down his back. "Uhm. Only found it twice, so far..." he admitted. Right before, and once with Genma. "... Told you. Mostly been topping. And... Not playing that much with myself back there..." he might as well be completely honest.

"Ooooohhhh..." Jiraiya noticed that shiver. "Sooo... you're practically virginal...." A broad hand slipped down his stomach as the older man's interest perked up a notch, and a tongue tickled Kakashi's earlobe. "I like that."

"Nn...." A small groan wouldn't be suppressed. "I.... Guess you could call it that." voice rather breathless, too, as he tilted his head slightly to allow Jiraiya more working space.

"And sensitive.. I like that too. You'll sound so pretty screaming when you cum around my big dick. Fucking your little tight asshole..." the tongue licked down his neck, the wild hair tickling Kakashi's skin.

Another small shiver, as he bit his lip with a half-quelled moan, hips writhing just a little, still, to find that perfect angle....