Poll Winner: Issei's Loss (Naruto/Highschool DXD)

Yeah, I know this is late. Sorry, folks. December's been kicking my ass. 

Summary: Highschool DXD/Naruto: A crossover where Jiraiya steals Issei's harem from the little boy, starting with the big-titted Akeno. Includes: Mind break and NTR

---

The last thing Jiraiya remembered was sinking into a watery abyss. He remembered dying, feeling nothing but cold numbness as he tried and failed to breathe. Water filled his lungs as he died, gone from the world of the living. 

He thought of Tsunade, and Naruto, and all that he knew, but it was gone now. 

When Jiraiya opened his eyes, he found himself in another world, similar, but very different from his own. The world had technology just a bit further ahead than his own, and there were no hidden villages. 

Jiraiya explored this strange world, gathering information as a ninja would. The more he learned, though, the more confused he became.

Ninjas were left as pieces of history and fiction. There were no Tailed Beasts and no jutsus. So much of what Jiraiya knew was just… gone. 

Why was he here? What was this world? Jiraiya had no idea, but after a bit of observing, well, he did notice one thing in particular. 

This world had a lot of hot girls in it. Beautiful women, gorgeous gals, sensual sluts. The average breast size of his world felt like it was B or C, but here, so many women seemed to have Ds or even Es! It was paradise, but maybe that was the answer…?

Maybe this was his paradise, his place to have fun and rule, to not have to worry about morality? About anything? 

It made sense. The last thing Jiraiya remembered was dying. Maybe this is what happened to people who died? They got to go to another world, similar to their own, and just… have fun. 

Jiraiya quickly discovered he was the strongest person in this world. He was always pretty tough back home, but here, no one could touch him. Jiraiya actually stole a kiss from some pretty face right in front of her husband, and he couldn’t even touch Jiraiya as the old sage kicked his ass and kissed his wife again. 

At one point, some punk with a gun tried shooting Jiraiya and he caught the bullet in his teeth with ease. 

Things were so easy in this world, Jiraiya could have whatever he wanted, but one closer look at the world revealed the one thing he really wanted.

Jiraiya focused his attention on a young man named Issei, but more importantly, Jiraiya focused on all the hot, busty sluts he kept around him. Oh, just watching these gorgeous girls waste their time with the little prick made Jiraiya’s blood boil.

What was this punk doing, ruining his heaven? His paradise? That’s when Jiraiya realized who this Issei kid was, and why he existed. 

He was here to help Jiraiya fulfill his greatest fantasy… Stealing an entire harem away from some loser, and Issei was that loser!

There was no doubt in Jiraiya’s heart. This was what he wanted, this was destiny. He died for a good cause, and now it was time to be as bad as he wanted with no repercussions!

The first target was obvious. Jiraiya picked her first out of the group of deluded babes fawning over the loser. The big-boobed bimbo, Akeno. The beautiful woman and Issei were scheduled for a date together later this evening, and Jiraiya had every intention of ruining it.  

Jiraiya found Akeno waiting for Issei at a small, simple diner. She would be waiting for a while considering Jiraiya had made sure to sabotage Issei. Nothing major, just a few little sabotages that made sure Issei couldn’t arrive on time to meet Akeno for their date, and he made sure he couldn’t call her to explain himself.

Akeno sat alone at a table, sighing as she watched the time tick by. She was all alone, and Jiraiya started the next phase of his plan by simply disguising himself as one of the workers. He was a ninja, after all. All he had to do was sneak inside and keep himself inconspicuous.

He had a glass of water on a tray, and he placed the cold glass on Akeno’s table. He silently took her empty cup, and Akeno didn’t even pay him any mind. 

By now, most people at the diner were distracted with their own devices. They focused on their work, their romantic partner, anything and everything save for the dark-haired woman who drank her spiked drink.

The stuff was strong, but subtle, and it did its work well as Akeno found herself falling asleep on her chair. She fell towards her table, and Jiraiya was there to catch her, helping her stand as he made a show of telling everyone he was going to help her... 

---

Akeno woke up on a bed, to the feeling of someone kissing her lips. She moaned against the soft lips, pressing her black lips against his as she wrapped her arms around him.

“Issei,” she moaned, gasping as she felt something press against her panties. “Ah…! Yes…”

Finally. She had been waiting for him. For Akeno’s hazy, lost mind, this made sense. Her lover had found her, and he was kissing her now as one of his hands rubbed against her bra covered breasts.

Where did her clothes go? Where-ahh! Her thoughts were sidetracked as a hand pinched her nipple and pulled on it. 

Issei kissed her like he had never had before. His tongue felt so sweet, so delicious in her mouth. It stretched down her throat, and she moaned loudly as her arms embraced him. He sucked on her dark-painted lips, before the kiss broke and Akeno licked up the saliva linking their mouths.

“Issei,” she moaned, feeling his hand squeeze her breast. “You feel so-ah… so wild tonight. What’s gotten into you?”

“Heh. Trust me, slut. That bitch could never treat you like this.” 

“Huh…?” Akeno blinked, looking at the man looming over. White hair. Bigger muscles. An adult. This was a man, one she had never seen before, and Akeno’s eyes widened as she tried to push him away.

He overpowered her with ease, grabbing her hands and pinning them by her sides as he grinned. He kissed her once more, and Akeno moaned in protest as his long tongue swirled inside of her mouth.

She tried to push him off again, and this time he let her try, knowing she couldn’t do anything to stop him. He was impossibly strong compared to her. He was safe as his hands grabbed at her bra and tore it off of her body with ease, before he ripped her panties off with similar speed.

The man broke the kiss, licking his lips as her black lipstick left smudges on his skin. He grabbed her hips as he pulled his hips back and slammed into her, fucking Akeno’s pussy without any warning. 

She cried out, gasping as the thick member pounded her pussy, fucking her so hard that all she could do was scream.

“Gah! You’re already so fucking wet!” he laughed. “Fuck, you feel tight. Did that loser ever fuck you?” Akeno didn’t know how to respond. 

This man was clearly more powerful than her. This man’s cock was easily bigger than her Issei’s. She wanted to just seal her lips and keep herself quiet, but then the tip of his cock pressed against some of her nerves, and Akeno was moaning loudly in pleasure from the blow.

“W-who are you?!” she cried. “W-why are you doing this?!” 

“Name’s Jiraiya,” he grunted as he thrust into her again. “But you can call me Master, slut.”

Akeno trembled at the insult, and she bit her lower lip as Jiraiya kept fucking her, making the bed under her shake as her pussy tightened around his shaft. Her face was hot. She didn’t know why her body was so wet, why it all felt so hot as he rammed into her…

She had no idea that Jiraiya had added a little something to her drink, beyond the stuff to knock her out. It left her body horny and hot, and her mind weak and malleable as Jiraiya’s balls smacked against her pussy.

“You slut. Look at these tits. That little bitch never treated them right, did they? Never fucked you like the masochistic whore you are?” he growled, groping and squeezing her chest with his two hands as his hips moved.

N-no. Issei never treated her like this, and he never thought of her as a masochist. But god, if this was what masochist felt, maybe she should reconsider?

Akeno shook her head, trying to fight the ecstasy her body was feeling. Yet when Jiraiya’s cock pressed against her G-spot, she moaned out loudly, gasping in pleasure as her body quivered. Her moist womanhood clung tightly to his dick, squeezing it as he spat down on her face.

Akeno licked up his spit on reflex, unable to help herself as her mind was broken down with every thrust. It was like a hammer smashing a statue of her Issei. All her she felt for him, all her love and idolization she had built for herself for him, was crumbling as a new statue rose up to replace it.

One of gold. One meant to shine under the light of the sun. Her Master… Her powerful, big-dicked Master!

Akeno’s arms stopped trying to push the man away, and they wrapped around his head, pulling him down suddenly so she could properly kiss him. His eyes widened, before he closed them, sucking on her lips as the sound of their love making filled the room.

Jiraiya broke the kiss and hissed in her ear. “Insult that little twerp, and I’ll cum inside of you.”

Akeno’s eyes widened, and she showed no hesitation as she nodded her head. “Issei is a worthless piece of shit! I-I hate him! I hate him! I hate him! His cock is so tiny compared to yours, Master!”

Jiraiya grinned, and he gave Akeno’s large breasts one last squeeze as he kissed her again. The bed under them was wet with their juices, and it only got worse as the two came together. His sperm filled her pussy, flooding along the inside of her cunt, and filling her womb.

He soon overwhelmed her, and his sperm dripped from her cunt as Akeno drank his saliva from her mouth. 

The older man knew the little slut was broken… but he spent the rest of that night making sure she knew who owned him. 

---

“Hey, Akeno. I’m really sorry for keeping you waiting last time,” Issei smiled. 

Akeno turned her eyes to the young man, and she blinked, her face looking utterly bored as she stared at him. Then she put on a smile and laughed off his apology. 

“Oh, how sorry are you? You don’t seem very sorry,” she teased. 

“I am! Really!” he replied, and before he could sit down, Akeno held up a single hand. She stopped him from sitting as she smiled at him.

“Oh, well, if you’re sorry, you’d kiss my feet.”

“W-what?” he chuckled, tilting his head to the side as he stared at her. “Akeno, that joke’s a little-”

“I’m not joking, Issei. You really broke my heart when you left me waiting,” she whimpered. She put on a frown and let a few crocodile tears fall from her face, pouting as her eyes turned to Jiraiya. 

He nodded with approval, grinning as Issei’s face burned a hot, hot red.

“I-I-”

“I understand. You must not care about how you hurt me,” she sighed, and the brunette boy shook his head. He fell for her act, and it took all of Akeno’s will power not to laugh at how pathetic the young man was. What did she ever see in him?

“N-no! I care! Look, I-I’ll do it, but just real quick, okay?” Akeno smiled at him, her obsidian lips coiled into a grin as she nodded her head. 

“Oh, Issei. You’re so sweet.” The young man looked around the diner, blushing as he counted how many people there were. Not a lot, thankfully, so he leaned down, crouching down onto his knees as he inched his face closer to one of Akeno’s shoes.

When his lips touched her foot, her other foot landed on the back of his head, keeping him there as Jiraiya darted towards Akeno. While the gorgeous, buxom woman dug her heel into the back of Issei’s head, making him quietly whimper in pain, Jiraiya and Akeno kissed.

Their lips met and Akeno’s eyes fell shut as her Master placed a hand on her breast. He gave her large breast a squeeze as his lips nibbled on her bottom lip. Her black lipstick left a stain on Jiraiya’s lips as his tongue dived into her mouth, swirling inside of her as she sucked on his tongue.

Issei was caught under her heel, feeding her sadism as Master Jiraiya kissed her, and fed her masochistic side. The side only Master could see, and only he could please. Her heart skipped a beat as she and her Master made out while Issei struggled to lift his head back up. 

This was only the beginning.