Issei's Lusty Introduction to Life as a Devil: Chapter 1 - Gaming the System

[Highschool DxD] Throwing boulders and being able to do magic is all well and good, but Issei didn't really see what was so great about being a devil until he truly got to know the two Great Ladies of Kuoh Academy.

Snippets of Issei's erotic adventures as a devil. OOC Issei.

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This whole 'Devil' thing was weird and confusing, Issei mused with a skip to his step. It wasn't even the supernatural craziness that baffled him - a life of consuming anime and video games had prepared him rather well on that front, unsurprisingly.

No, it was the more mundane aspects of devlish life that he found strange. Advancement, for one.

He'd been promised his heart's desires from his king when he'd been recruited into her peerage. All he had to do was grow in strength and advance as a devil and not only could he get his own Evil Pieces in time, but his own noble title and lands too. Anything, really.

So, how did one grow in strength and advance?

It wasn't by drinking juice, lifting weights and running five kilometers a day like he'd thought, no. It was with contracts.

As a devil, his body was more physically powerful and even had the ability to do magic, but that was limited by his demonic power. Power limited the strength of his magic, power limited how much of it he could pump through his body and boost his strength and speed, and power limited how much of it he could use before his body became fatigued.

In days of old, devils used to rip the souls out of humans and consume them to replenish and boost their power. Thankfully - according to Rias - that practise was outlawed generations ago. Now, devils had contracts as a means to attain more power for themselves, and their kings.

While consuming souls was outlawed, devils still gained power through their contracted humans' essence, they just didn't drain them dry anymore, as it were. Rias had explained it to him rather simply. Devils feed off the desires of humanity, the stronger the desire, the stronger the power they siphon from it. She'd summed it up by calling them 'emotion vampires,' and Issei instantly understood.

He'd blushed up a storm when Himejima Akeno, his new insanely beautiful senpai, had whispered into his ear in the midst of his education that she liked to siphon power off her contracted humans' lustful desires.

With an insanely erotic body lilke hers, Issei wasn't surprised when she revealed how powerful she truly was.

Which made the look she gave him when he summed up her method as prostitution that extra bit more terrifying,

Rias had found their exchange highly amusing, the best friends often keen to tease one another or see them be teased.

'Be that as it may,' Rias had headed off her friend before she could fry her new Pawn, 'Akeno's method is highly effective and has made her one of the most powerful devils of our generation. You should learn from your senpai.'

'Pfft,' Issei had scoffed and waved her off. 'I could easily get more than the hooker, just you watch!'

Rias had to step in at that point before Akeno electrocuted her new pawn.

'Big words, Issei-kun. How about a wager then? To see who can harvest the most power from their contracted humans?' Rias had tempted him with her beautiful teasing smile, her cheek resting against her fist and her pale legs crossed, revealing a sinful amount of upper thigh with her ridiculously short skirt.

Issei wasn't too proud to admit he'd gulped at the suggestive tone and the way lightning had crackled between the madly grinning Akeno's fingers.

'What are the stakes?'

'If you fail to harvest more power than Akeno in one evening, you'll have to entertain her for one whole night.'

Had that sentence been uttered to him before he'd met and gotten to know his beautiful senpai, Issei would have thrown the contest right there. The way her breath quickened and lightning continued to dance along her delicate fingers however, he doubted he'd find the evening very entertaining.

'And when I win?' he had asked with a confidence he had only marginally felt in that moment.

'I assume you're still a virgin?' Rias asked with a teasing smile.

Issei had bristled and blushed at the question. 'It's perfectly normal to still be a virgin at seventeen!'

Once Rias and Akeno had stopped giggling at the embarrassed teen she continued.

'Well, if you win, maybe you can see your first real-life pussy?'

Issei had agreed so fast he had made Rias' head spin. He didn't even care to ask for specifics. Would he get to fuck Akeno? Rias? Both?! He didn't care.

He had developed a genius plan to beat Akeno and he was confident of his victory. While Issei knew more than anyone how great a motivator sex was, it was nothing compared to hunger.

With his parents living overseas for work, he had become a pretty excellent cook to help save money - mainly so he could pocket the food allowance his parents sent him…

He had enlisted the help of his new peerage-mate Kiba - who also had a vested interest in seeing Akeno brought down a peg - to help hand out contracts to the needy. Homeless, impoverished, orphans - anyone who could use a hearty meal. He'd set up his stall on the street and was inundated with people handing in the signed contract for a beautifully cooked omurice.

He cooked for hours, with several woks going at a time and a crowd gathered around to watch, he was certain he was going to earn his victory. With his impressive skill he had been able to feed everyone that came. He had felt the power rolling in as he satiated these peoples' hunger and entertained them with his cooking skill.

He didn't finish until well into the evening, returning the cooking implements to the nearby restaurant he'd rented them from before rushing to the station to catch the last train home. Issei didn't realize how exhausted he truly was until he sat down in the empty train compartment and rested his head against the window.

He was startled out of his past musings by his buzzing phone. Looking up with bleary eyes he let out a sigh of relief when he confirmed he hadn't missed his stop while reflecting on the previous days' events.

'Yo,' Issei answered the phone without looking.

'Congratulations my magnificent pawn,' Rias' sensual voice - even more sensual than usual, his bleary mind didn't fail to notice - greeted him on the other end.

'Heh, was there ever any doubt?' He replied cockily, wondering how she knew he'd won already and if she could feel the power flowing through her like he did. 'I can't wait to see the look on Akeno's face.'

Rias' giggle at that remark was interrupted by an erotic moan and Issei instantly perked up.

'Is she getting ready for me?! I'm not tired anymore!'

'She was quite...' Rias paused as she moaned softly again, '...put out.'

Issei was rock hard. He didn't know if devils just naturally exuded sexual charm, but it felt like Rias could do that to him by just smiling in his direction.

'You'll have to tell me what you did to win,' she continued while breathing heavily. There was also a soft slapping sound he could barely make out in the background and he pervertedly wondered if she was slapping her own clit while masturbating.

'So…' Issei broke the silence, his cheesy and awkward grin audible in his tone.

'I suppose you want your reward then?' Rias replied with a delighted giggle. Issei's face heated up and he replied in the affirmative.

'Enjoy, Issei-kun, you earned it.' Rias cut the call then and Issei looked at his phone in confusion. She definitely had a cheeky tone to her voice just before hanging up, but Issei couldn't puzzle the meaning.

'Maybe she'll let me fuck her another night?' he naively thought as his phone buzzed again.

It was a picture message. Issei perked up and quickly opened the text from the prez. His goofy smile turned to one of bemusement when he saw the incredibly erotic pic.

The picture, enlarged to take up the entirety of his phone's considerable screen, was one of an incredible pussy, just like Rias had promised. The skin was pale and the perfect pink lips unobscured by mosaics or any kind of censorship.

The pussy also had an incredibly thick cock in the process of fucking it, the pretty pink lips stretching obscenely around the dark and girthy member. The cock was so thick Issei mused it was probably a porno clip of a random girl fucking herself with a dildo.

'That thing has to be as thick as a can of Pringles…'

'I thought you were going to let me fuck you. I didn't think you'd cheap out on our bet and just send me a random porno pic from the internet.'

Issei didn't need to wait long for a reply to his text, though his leg bounced with frustration and impatience. He felt cheated.

'Who said anything about fucking me? Our deal was you'd get to see a real-life pussy.

And who said I got this picture from the internet?'

Issei frowned at the first part of the message and had to concede defeat. He'd let his excitement get the best of him, allowing the prez to manipulate him.

The second part of the message took a little more time to register in his exhausted mind, but when it did, it went off like a bomb.

'NO FUCKING WAY! THAT'S YOU?! Why do you even have dildos that big?! That's so hot!'

Issei waited for the reply from his incredibly beautiful and slutty senpai, his leg back to bouncing in anticipation. He opened the previous pic again and saw it in a whole new light. He wanted to blow up and frame this extreme close-up of Rias' pussy and hang it on his wall, but failing that, it'll go in his wank bank forever.

A reply wasn't quick in coming, however, and when the train pulled up to his stop, he was forced to pocket his phone and disembark. Retrieving his bike from the bike lock he'd left it in, he rushed home, eager to find out if Rias thought her end of the deal was fulfilled, or if she'd be making further deposits in his wank bank.

Issei almost tore the door off its hinges in his rush to enter his empty house. He had two messages from Rias and he couldn't wait to read them.

He dropped into the plush couch in the living room and opened his messaging app. The first message was a simple text.

'Oh my precious pawn,' it read, and Issei could practically feel the affectionate yet also patronizing tone she normally took with him, 'That's adorable. I haven't used a dildo in years. Why would I when I have easy access to fine specimens like Michael here?'

Issei's eyes widened in shock when he scrolled down to see the picture she had sent.

Rias was laying face down on what he presumed to be her bed while holding her phone out in front and above her to take a selfie. Her impishly grinning face was in the lower left of the frame while her voluptuous naked body filled most of the rest of it. This wasn't a simple nude photo, though. What shocked him was the man she had captured in the selfie with her.

He had his pelvis pressed against her fleshy ass, clearly in the process of fucking her with one hand resting on her lower back while the other curlsed around underneath her, likely playing with her clit. All he'd seen of the guy he was incredibly jealous of was his milk-chocolate skin tone, his shredded physique and, from the first pic, his obscenely huge cock.

He was shocked out of reverie when he received another message. This one was taking a while to load and Issei felt his pulse quicken when he realized it was a video clip.

When it finally loaded, he hit play. Rias's lover had clearly taken her phone at this point because the clip was from his point of view, and the whole picture swayed in time with his thrusts. It started with the lens aimed at the back of Rias' head, buried in a pillow as she moaned in pleasure. Her curtain of crimson hair was pulled over her shoulder, allowing a view of her pale back as he traced the lens down her spine until it got to her glorious, pillowy ass and his huge cock thrusting in and out of her pussy. The obscene rod was a darker tone than his skin and it was slick with his king's juices as it speared in and out of her.

He then flipped the camera around to show Issei his grinning face. 'Sorry man, your girl said her boyfriend got off on her fucking guys with big dicks. You don't mind, do ya?'

'What?' Issei thought in befuddlement.

'I mean, I'm insanely jealous that he gets to fuck buchou instead of me, but she's not my girlfriend…' Issei thought in confusion before understanding dawned on him.

It seemed Rias was as slutty as her best friend. It also seemed she had a wicked NTR kink that she was trying to roleplay. He felt no shame in whipping out his dick and beating off to the best ameteur porn he'd ever seen in his life. It was a far cry from getting to fuck her himself, but if Rias hoped he'd despair at the thought of other guys fucking her, she was barking up the wrong tree.

He had to wait twenty minutes until he got another message, but Issei was thrilled when he realized it was well worth the wait.

The clip was still from Michael's point of view. He was on his back this time as Rias rode his huge cock while biting her lower lip lustily. She rode him hands free, one leg resting on her knee while the other had her foot planted on the bed so she could control the fucking. Her hair fell around her face like a curtain as she looked down on Michael lovingly while her hands fondled and played with her prodigious tits.

'You like riding that big dick baby?' Issei heard Michael ask the smiling devil.

'Mhmm,' Rias moaned in reply. 'You're so much bigger than my boyfriend…'

Issei could only roll his eyes at the byplay, though if he were honest with himself, he was a little jealous of that guy's massive dick. How could he not be? His own was only slightly above average - he checked, with a ruler - but it was clear Rias liked them… big. Bigger-than-porn-star big at that…

Still, he tuned out their NTR play and just locked in on Rias' tits - arguably her best feature- as she squeezed and played with them. He loved how her tit flesh escaped out from between her fingers when she squeezed tightly enough, he also loved how puffy and pink her large nipples were. If nothing else, he'd have to thank her for her heroic deposit into his wank bank.

It seemed Rias was too busy to send him any more pics of her evening, so after a truly epic wank session and a shower, he was just about to climb into bed when his phone pinged a couple more times.

'I feel like I didn't properly pay up on our bet. It's not fair to you if there's a massive dick in the way, right?'

The text was followed by another video clip. When he hit play, the clip started with Rias holding the phone up to her face in selfie mode. She was grinning at him through the lens and blowing him a kiss. He noticed that her skin was covered in an alluring sheen of sweat that reflected the light and made her look even more sexy. Biting her lip, she let the camera trail down her shiny body, her massive tits hanging free and heavy on her chest. It then trailed over her flat tummy before stopping at her utterly soaked and thoroughly used looking pubic region. From the angle she held her phone, not only could he see her pussy in the most unobstructed way yet, he could also see her face still grinning down at him through the gap between her hanging tits.

Her delicate fingers ran up and down her drenched pussy lips several times before she spread them wide open, revealing to Issei her still slightly gaping entrance. Issei then groaned aloud when copious amounts of cum started leaking out of Rias' abused pussy, accompanied by the sounds of her sultry giggles.

He ignored the sound of Michael laughing in the background.

'Did you enjoy the spoils of our bet, my beloved pawn?'

After recovering from the insanely erotic sight he'd just seen, Issei made sure to save the most recent clip to his favourites folder for later use before replying.

'If nothing else, it's taught me the importance of being very, very clear with the stakes in the future, you crazy NTR-loving nympho. I'm not gonna get cheated out of our next bet!'

'Aww, don't you want to be my boyfriend? That wasn't just roleplay you know. You're incredibly cute. My family is known for being very close with those in their peerages…'

Had she asked him yesterday, Issei might have literally cut off his left arm for the opportunity. He wasn't that desperate though that he'd be cool with getting cucked for the rest of his life, no matter how hot Rias was.

And she was hot.

He hesitated for only a second before shaking his head vigorously to dispel the traitorous thoughts threatening to seep into his mind.

'I think I'd rather stick my dick in a toaster.'

'Your dick can fit in a toaster? Oh dear… (＾艸＾)'

Issei decided then he'd texted enough for the night.