Issei's Lusty Introduction to Life as a Devil: Chapter 2 - Practise makes Perfect

As Issei's body sagged with exhaustion, he wondered if maybe he had been baited too easily into taking another bet from his King.

After the smashing success of their previous bet, it didn't take Rias long to come up with another challenge she hoped her newly minted pawn would also overcome.

The challenge? Simple. Just be able to win a spar against Kiba within the week, without the use of his Sacred Gear. Easy, right?

'The fuck it is,' Issei thought sourly.

The challenge was rigged from the start, which Issei should have clued in on given the stakes. And those stakes? If he was able to win, Rias would actually let him fuck her, no tricks, none of her 'NTR' play. And if he lost? He would be forced to be Akeno's entertainment for an evening.

Yeah. He probably should have seen the challenge for what it was - payback from Akeno for defeating her in the previous challenge.

'I need to stop being blinded by pussy!' Issei raged internally as his eyes flicked over to Rias who watched on, arms crossed under her massive tits with a pleased smile on her devilish features. Beside her stood Akeno, her cheeks tinged pink and almost salivating at his imminent demise.

It wasn't like he'd put up a pathetic showing. The only reason he couldn't defeat Kiba was the stupid sacred gear limitation. Kiba's gear let him create magical swords - pretty cool, but not vital for his fighting style.

Issei's gear on the other hand? It was integral to his fighting style. The Boost functionality, he discovered, worked on literally anything he did. His body was the first obvious target for Boost's usage, but then he realized he could narrow the focus for a much greater effect. A single punch, or a simple spell, for instance.

Issei wasn't as tragic at magic as the currently salivating sadist seemed to think. He found he was quite adept with telekinesis. One boosted telekinetic crush and this fight would be over, but without boosting the spell, Kiba was easily able to shrug it off.

Kiba charged at him again. Issei found he was able to follow the much faster knight's moves, and even match them after promoting to knight himself, but he just lacked the experience Kiba had with hand-to-hand combat to be of any real threat. He did get a sense of satisfaction when he heard the pretty-boy grunt in pain every time he landed a hit with his higher strength, but Kiba would often counter with a flurry of weaker blows he just couldn't block.

It wore his already exhausted body down even more.

'That's time!' Rias called from the other end of the clearing as Issei finally fell to his knees in exhaustion. 'You put up a valiant effort, my beloved Pawn, but I'm afraid it's your loss. The week is up.'

'I'm sorry Issei,' Kiba addressed his new peerage-mate with a sincere apologetic smile. The fact that he looked equally as exhausted was the only thing saving Issei's pride at that moment.

Issei shrugged off the apology with a grunt. 'It's alright pretty-boy, I got what I needed from our spars.'

'Ara ara,' Akeno interrupted their bonding moment with a titter. 'I believe you have an appointment to get to, Is-sei-kun.'

Issei growled at the ecstatic look on her face, but didn't argue. He wouldn't be coming out empty handed after this. If this bitch thought she could tame a dragon, she was in for a rude awakening.

Issei should have been feeling scared and vulnerable in the position he was in, but with Akeno standing before him in a lewd version of her Fallen armour, he just couldn't find it in himself to care.

Her normally impressive black armour with gold trimmings and black feathers was modified in such a way that Issei was finding it hard to take her seriously. Normally, the armour had a black chestplate and armoured skirt that protected her modesty. This 'lewd version' had foregone those pieces only for an… armoured micro-bikini?

The top strained heroically against her gigantic tits - even more stacked than Rias! - with only two tiny scraps of metal barely covering her nipples. The bottoms were a thong cut so low that he knew she was shaved bare, they also rode high on her hips in a vain attempt to make her look more curvaceous than she actually was.

'So what now, chicken legs?' Issei taunted from his vulnerable position on the floor. She had his wrists bound so they were spread out towards the walls and his ankles bound to hidden manacles on the floor. The end result was him kneeling on the floor, stark naked with arms out wide.

Issei wasn't ashamed of his body. His dick was above average in size and his already shredded physique earned from countless hours at the gym became even more so after his devil transformation. He knew there were plenty of girls that would happily want a piece of him, and he was only a virgin still because his standards might be a little too high.

'That's my story and I'm sticking to it.'

'What was that?' Akeno asked in a dangerous tone. It seemed he hit a sore spot. Between her and Rias, she may have won in the tits department, but Rias clearly had the more curvaceous body. A rounder butt, thicker thighs, wider hips - you name it.

Akeno must have known it too.

'You heard me. Get on with it, you've only got two more hours until midnight.'

Akeno's breath quickened and she smiled dangerously at Issei while stroking her riding crop sensuously.

Without warning, her arm lashed out like lighting and she whipped him across the face with said riding crop. It left a stinging sensation on his cheek, like a light slap, nothing more.

Issei refused to let any emotion but boredom show on his face as Akeno continued to whip him, the intensity of the strikes increasing as her fury at his non-reaction rose.

'Look at you, your pathetic little dicklet is getting hard from this!' she crowed as she ran her lithe foot up and down his shaft.

Issei refused to take the bait and shrugged. 'Once I stopped looking at your little chicken legs and instead focusing on your tits, I couldn't help myself. They're really your only redeeming feature.'

Akeno smiled with her mouth only as she brought her foot back and flicked it forward. Issei groaned as she used the knuckles of her toes to flick his testes with enough force to cause pain to shoot up to his stomach.

'How was that, Is-sei-kun?' Akeno taunted, pleased to finally get a reaction out of him.

He matched her grin but internally winced at what came out of his mouth next. 'I've got a bit of an itch to the left, you mind scratching it?'

He thanked whatever higher being was listening that Akeno was clearly not a fan of Bond movies, otherwise he'd look as pathetic as his poor testes felt when Akeno used her riding crop to slap his balls. Hard.

He couldn't withhold the scream this time, and he would have curled into a ball if his bound position wasn't forcing him to stay kneeling as he was.

'Oh my, I may have gone a little overboard. Let me help you,' she said in her caring onee-sama voice as she knelt down, took his balls in her hand and started to send magic into them. Surprised at the sudden surge of warmth in his balls after feeling such pain, Issei was as surprised as Akeno when he groaned and came instantly all over her face.

Issei laughed openly at Akeno. Her face marred with his cum and her smile frozen on her face.

'You are going to regret that, Issei-kun,' she promised as lightning danced across her fingertips. She slapped him across the face with a lightning-covered palm and Issei convulsed as the electricity surged through his body.

The fact that he was still laughing at her cum covered face through the pain, in hindsight, was probably not his smartest moment.

She thunder-slapped him several more times until he was a panting mess at her feet. He didn't look down though, he stared up at her defiantly - a mocking grin on his lips - as she stood on his erect-again shaft and pressed down on it with increasing pressure.

'Is that the best you've got, chicken legs? If I'd known you were such an ameteur I'd have volunteered for this sooner. You're giving sadists everywhere a bad name.'

Her foot curled around his shaft until her heel was pressed against his tender balls.

'If I had known you would enjoy this so much I'd have taken you sooner, little masochist-kun.'

'It's ABOVE AVERAGE,' he raged internally, sick of these sluts comparing him with the porn star dongs they seemed to fuck on a daily basis. He let none of this show on his face though.

'Let's make a deal,' he proposed with a wicked grin. Akeno's breath hitched in excitement at the thought she might actually get to torture him for more than just that evening.

'Oh?' she asked as she continued to apply pressure to his balls.

He didn't let his discomfort show and continued to talk. 'You have until midnight to make me break and beg for you to stop. If I do, you win. Easy for an expert sadist like you, no?'

Akeno's breath quickened as the parameters of their latest bet were laid out. 'The stakes?' she asked, her pink cheeks growing pinker as she became more aroused. Issei was sure he could even make out her juices leaking out from her little micro thong. He shook thoughts of licking up that trail all the way to its source from his mind and answered.

'If you win, I'll be your toy for a month,' Issei proposed and Devil damn-it, she nearly came from those words alone. 'But,' he interrupted her fantasies with his raised voice. Noticing her attention was back on him he continued. 'But, if I win, you agree to have sex with me, any time I want, for up to six months.'

She looked amused by his proposal.

'You want to be my boyfriend, doggy-kun?' she asked, easing up on the pressure on his balls and circling his shaft with her foot.

'Sex-friend,' he ammended. 'As you and Rias won't even let me forget, I'm a virgin. Who better than a sexy slut like you to practise and get better at sex with?'

Issei actually found it kinda hot that she didn't dispute his 'slut' slur. 'And what of my contracts? Do you expect me to stop them during this duration?'

'Afraid you'll lose?' Issei taunted as Akeno's smile froze and she put her heel on his balls again and started to apply pressure. His back arched when she pressed harder than before and he gasped out an answer. 'I don't care what you do on your time. You'd be a breathing onahole for me during the six months, not my girlfriend!'

'Mmm,' Akeno purred as she eased up the pressure. 'It's not like you'll win and this disgusting little dicklett will come anywhere near me. Deal.'

Knowing she was now on the clock, she tossed the crop aside and now both of her hands crackled with electricity.

He wouldn't break. Despite him teasing her about her chicken legs, Akeno was still arguably even hotter than Rias - depending on his mood on the day you asked him. Her onee-sama personality combined with her sluttyness and hidden sadist tendencies was just such a sexy combination, and he'd had fantasies for weeks about playing with those pillowy tits of hers.

There was no way he'd break and lose out on the opportunity of a lifetime.

Akeno tried. Oh did she try. But when the clock hanging on the wall behind her struck twelve, he looked up with a wide grin - his body still twitching from an over exposure of 'electrotherapy.'

With the help of some demonic power and his sacred gear, he was easily able to destroy Akeno's previously indestructible bindings as he surged to his feet. His grin widened further when Akeno took a step back in shock and a little fear.

He prowled towards her like a dragon on the hunt. She kept backpedalling until her back hit the wall. Slamming a hand against the wall beside her head in the classic kabedon move he leaned in until his lips were right by her ear.

'I win,' Issei whispered directly into her ear, keeping his voice low so it sounded as deep and husky as possible. He's practised this move countless times in the mirror in the hopes he'd find himself in this very situation one day. He hoped he didn't look stupid.

He was finding it hard to imagine how it wouldn't look stupid. He was still buck naked, his body littered with scars from his 'playtime' with Akeno - though they were quickly healing, thanks to his devilish nature - while his dick was as hard as a baseball bat and pointing straight at her. He didn't even try to avert it, letting it rub against her midsection as he drew closer, his pre-cum leaving a trail against her flushed skin.

He didn't care though. And neither did Akeno. Despite her bluster, and all the derogatory comments she made while playing with him, she seemed equally as excited and aroused if her elevated breathing and wide eyes were anything to go by.

Issei wasn't fucking around with his wager. He wanted to start collecting as soon as possible, as often as possible. He'd spent a majority of his teen life reading hentai and watching all kinds of porn, but he knew that was a pitiful substitute for the real thing.

He wanted to be a fantastic lover. Not just average like other aspects of his… character. To do that he needed practise with the real thing, and who better a teacher than the biggest slut he knew?

One who is also arguably the most attractive woman he knew.

It's how he held on through Akeno's sadistic ministrations. The thought of this moment, of doing this - of doing her - kept him strong when he otherwise would have given in.

Akeno moaned and jerked when he sucked her clit into his mouth with as much force as he could manage.

'Careful!' she hissed, grabbing him by the hair and pulling him away from her soaked pussy. 'Overeager virgins,' she muttered under her breath before letting out a suffering sigh. 'Just because the clit is the star of the show, doesn't mean you go at it full-force until I cum. That's what virgins who read too much hentai do.'

Glaring at her, he replied. 'Then get to teaching, chicken legs.'

She rolled her eyes. 'Yes, stimulating the clit feels the best, but just going for broke won't give the best orgasms. You have to pace yourself. Also, and most important before we continue, every girl is different. What you learn here might not be applicable with the next poor girl you trick into your bed.'

Issei stopped licking and pulled away from Akeno's pussy with a frown. 'Are you really gonna take that tone with me after what I had to go through to get here? If you really don't want to be here I'll go. I'm not gonna force you.'

Akeno rolled her eyes but chose to ignore him. 'Every girl is different, even if some of the broader strokes are the same. The number one rule for giving great head is learn to read your partner. Pay attention to what they say, sure, but also notice the non-verbal signs - heavy breathing, muscles tensing, back arching, hips bucking etcetera.'

'This is gold,' Issei mentally cheered as he nodded at Akeno seriously.

'Also, don't just focus on the clit. Lick the lips and lick around it too. Build anticipation. Make me - her - make her desperate.'

He positioned himself back between her thighs so she wouldn't see him smirking at her little slip-up. Akeno had ditched her little metallic thong thing but was still wearing the rest of her horny Fallen Angel armour. She lay back on her bed with her legs spread as Issei took instruction.

He started with slowly running his tongue up one side of her lips, circling but never touching her exposed clit, and then running down the other. He did as Akeno instructed and paid attention to how she reacted to his technique. Her beautiful ass would lift off the bed when he circled her clit and her breathing would increase, and she'd whimper as he drew further away or when he refused to touch the special bundle of nerves.

Her hand was running through his hair gently as he ate her out, as if showing her gratitude with her actions more than her words.

'Your tongue should never leave my clit or lips,' she began and squealed when he circled her clit again but chose to plant a chaste kiss on it this time, 'but that doesn't mean… that's all you can do.'

Issei took immense pride in the fact that Akeno was struggling to instruct as he ate her out. It's a far cry from the almost bored look and reaction she gave when he started.

'Use your fingers too mmm,' she encouraged. 'Don't penetrate my pussy with your tongue, your tongue should keep working my clit and lips, but your fingers can penetrate. Try and find my g-spot. Press against it, stimulate it.'

'Now this I think I know!' Issei crowed excitedly as he continued his routine with his tongue, ignoring Akeno's clit all the while. He backed off so he could insert his index and middle fingers into Akeno's gushing pussy but didn't go deep. Instead he curled his fingers back and pressed against the front wall of Akeno's vagina.

It was like he had struck her with one of her favourite lightning bolts. Her back arched and she let out a wanton moan at the action. He eased off however, remembering Akeno's instruction of taking it slow and building up to her orgasm. He continued his tongue routine while also adding pressing on her g-spot to the mix. He timed it so he would brush it gently as he drew closer to her clit with his tongue, and then back off as he eased off.

Like she taught him, he watched her body's reactions to his ministrations. Her breathing was steadily increasing, her moans were getting more hurried and wanton and the grip she had on his hair was steadily tightening.

'Don't just sit there all silent, it's weird,' Akeno instructed. She was leaning back with her eyes screwed shut in pleasure but she continued to instruct him, in between moans and laboured breathing. 'Don't be weird mmmhmm… Giving head is… intimate. Personal. Talk… talk dirty to me. Just talk to me. Tell me you're enjoying yourself. Tell me you love my pussy.'

'Makes sense. It'd be kind of a turn off if a girl was sucking me off and she just looked bored or uninterested with me.'

'If only your personality was as pretty as your perfect little pussy,' Issei said the next time he pulled away from her clit. He felt her grip in his hair tightening considerably but he chose to be daring and bit her inner thigh hard at her reaction. Her delighted squeal informed him that while not many girls would like that kind of rough treatment, Akeno certainly did.

'Look how wet you are down here you cheeky little slut,' Issei goaded in between his tongue laps of her pussy. 'I bet you were hoping I'd hold out the entire time.'

He completed another circuit, while steadily increasing the pressure he periodically pressed on her g-spot.

'I bet the only reason you shocked me is because you get turned on seeing my muscles tense.'

He could see and feel it plain as day. Her breathing was coming in quick gasps, her mewls were sounding more desperate and she was almost violently pulling at her own nipples that she'd exposed after tearing off her hilarious micro-bikini top.

Then he decided to go in for the kill.

'If you're a good girl, I might even let you do that to me again.' At the final word of his proclamation, he pressed hard into her g-spot and sucked her clit into his mouth with much greater force than she was expecting.

She squealed but Issei was confused when she leapt up and pushed him away after only barely a microsecond of the intense pleasure. He fell back on his ass and was looking up at the highly aroused looking young-woman in bemusement.

Akeno allowed her breathing to calm down as she closed her eyes on concentration. Issei took that moment to properly study her heaving tits as she sat crouched on her bed, soaking the sheets with her excretions.

'Good… good job,' Akeno praised when she got her breathing under control. 'One… one more lesson, and it's the most important one. Do you want to give your partner the most powerful orgasms imaginable? Every time? Do you want her to black out from pleasure and look at you like you're a sex god?'

Issei was nodding along with her questions eagerly as she giggled at his enthusiasm delightfully. It seemed she'd fully gotten on board with the idea of training a lover who would be an expert at satisfying her needy pussy.

'Then you need to learn about edging. Do you know what edging is?'

'Stopping before you can cum?'

'Exactly,' Akeno nodded with a pleased smile. 'The more you deny the big O, the more powerful it'll eventually be. Some girls may not...appreciate it in the moment, but that's where you need to man up and assert your dominance. She cums when you want her to, and when she does, she'll forget all about the frustration and anger she's feeling after all the edgings.'

'You love it then?' he asked with a raised brow.

Akeno closed her eyes and grinned contentedly as she recalled a particularly fond memory.

'It makes me squirt every time,' she admitted with an impish giggle. Issei groaned at the mental image squeezed down on his aching cock that was begging for release.

'Let's take care of that for you while I calm down,' Akeno offered with her oneesama smile back in place. It looked out of place when she was dressed the way she was, but Issei would have her wearing a garbage bag, he didn't care.

They both knew he wouldn't last long, he'd been hard and horny for hours. Still, it came as a shock when she took the entirety of his thick, six and a half inch cock in hour mouth in one smooth motion. Issei groaned in delight and grabbed her pony tail for want of something to do with his hands.

He could both hear and feel Akeno giggling around his cock and she pulled off until she only had his head in her mouth. She swirled her tongue around his sensitive glands like a seasoned pro - which he supposed she was - before taking the entirety down her throat again.

Seemingly not satisfied with how long this was taking after half a dozen more throatings like that one, Akeno did something he was never expecting.

Issei squealed when he felt a foreign invader enter his ass and press on something in there. His vision turned white and he saw stars as he experienced the most powerful orgasm of his young life.

Akeno pulled off him with a giggle as she watched him spasm as stream after stream of hot punk shot out of his overstimulated cock.

'Bonus lesson: prostate messages are great,' Akeno said with an elegant giggle.

When he finally came to his senses it was to a grinning Akeno standing above him, inspecting some of his cum on her fingers. She locked eyes with him, grinned and stuck her fingers in her mouth before licking them clean in a manner similar to what she'd done with his cock not moments ago.

'Akeno is sex-incarnate.'

'You dick might not be the biggest, but it certainly cums a lot,' she giggled at his annoyed frown. 'And you're an eager learner. Time to see if you pass the final exam.'

Issei resisted the urge to pin her down and fuck her brains out. He was hard enough, true, but he didn't want to act the pathetic virgin around her anymore. There's only so much hits a man's ego can take.

He would make her cum harder than she'd just made him cum. The only way he can shut her up about his totally above average and perfectly acceptable dick was to turn her into a gibbering mess the likes of which her donkey-dicked lovers couldn't even match.

Akeno's smile widened at the look of burning determination in his eyes as he slowly pushed her down onto her bed and locked lips with her.

He'd been at it for hours. Akeno had lost all sense of cohesion ages ago and he'd had to use her own bindings against her to stop her lashing out at him.

'I bet she wasn't expecting to be edged for this long,' he thought with a self-satisfied mental chuckle. He looked at the clock on the wall and realized it was almost four AM. He didn't have school tomorrow - today? - so he wasn't concerned about that, but his eyes were extremely heavy and he was close to passing out himself. His tongue and jaw ached and his cock was sore from the amount of times he'd had Akeno suck him off, or just jacked off on her tits as she lay on her bed, bound with her own magical ropes.

Issei decided to finally let her cum. He picked up his pace and started to focus more on her clit and g-spot. Her pussy and inner thighs were absolutely soaked and her bedsheets ruined with the amount of juice she'd secreted over the past few hours.

Issei had never been more proud in his life.

He may have even taken a few pictures and sent them to Rias just in case Akeno tried to lie about the status of their relationship in the future.

'Try and make fun of me now with some of the pics I have of you, Akeno,' Issei thought with a viscous glee.

'Please,' Akeno begged as she felt her orgasm coming again. 'Please let me cum. Please, please, please.'

'Of course, I think my naughty girl has been punished enough. Daddy will make you feel good.'

As Akeno started bucking violently in response to his dirty talk, Issei mused again on the little kink he'd stumbled upon with his dirty talk. Akeno must have some wicked kind of daddy issues, because every time he called himself daddy, or told her to call him it, she would lose her mind.

Akeno just continued to plead with him between her moans and quick breaths as he sucked on her clit and rubbed his fingers firmly against her g-spot just the way she loved it.

'Yes, yes, yes, yes, yes, yeeeeeeeeeeees,' Akeno squealed when he finally allowed her to cum.

'Holy shit look at her go!' Issei marvelled as he hips bucked and she squirted a fountain of juice from her pussy. He'd seen guys drinking the squirt in porn but Issei wasn't entirely convinced it wasn't just diluted piss yet.

Akeno would just have to be content with the uber powerful orgasm she was receiving. He continued to gently rub her clit as her hips bucked with her climax while also leaning down and feasting on her pillowy tits with delight. Her nipples were smaller than Rias', but her tits were bigger and flopped around on her chest as she moaned and convulsed in pure ecstasy.

Issei felt pretty pleased with himself when Akeno just fell asleep after she was done cumming, sheer exhaustion likely knocking her out as much as the power of her orgasm.

'Either way, I'm taking it.'

It was way too late to go home so he decided to curl up next to Akeno, pull the covers over them both and catch some shut-eye himself. He could feel exhaustion's effect on him too and after pulling Akeno into his broad, muscled chest - taking one of her magnificent tits in hand too, of course - he passed out almost as soon as his head hit the pillow.