Chapter 2 Part 4

Issei grunted as he pushed the first few inches of his thick member into her. Koneko cried out just like Kiba had as she lost her virginity in the same exact way as the blonde swordswoman. This time, Issei took thing a little bit slower though, sliding in and out of Koneko in long languid thrusts as he explored the limits of what her tiny body could handle.

He ended up bottoming out inside of the Nekomata at about halfway, the rest of his cock still outside of her even as he pounded away at her cervix. She was definitely the tightest pussy that Issei had ever been in though and he groaned as he slammed home into her again and again. Koneko wasn't handling it very well and eventually her cum-covered face fell away from Kiba's cream-filled pussy as she gave into the pleasure. The young cat girl came explosively shortly after she stopped trying to hold onto her composure.

From there, she wasn't able to stop, just like Kiba. In the end, Issei ended up cumming half inside of Koneko and half across her petite body, the Nekomata moaning at the sensation of his hot seed landing across her naked back and her pert posterior and her hair. Issei looked down at the mess he'd made of the girl and grinned, standing up and turning to the two girls who were still actually conscious at this point.

Rias and Akeno had their eyes locked on his crotch by the time he fully turned around, zeroing in on it like a pair of laser sights. The two women were both leaned back side by side, their knees up and their legs spread apart as they pistoned their ring fingers and middle fingers in and out of their extremely wet cunts. Issei steps towards them, his eyes flickering over Akeno's beautiful body. She's the last one to be fucked, and despite her seductive nature, Issei knows instinctively that it's an act. She's as innocent to the ways of love and physical pleasure as her mistress and her friends were. He could tell that much when he spanked her big bubble butt and fingered her to completion in that empty classroom.

Still, as her tits jiggled and she panted heavily, staring at him with wide lustful eyes; Issei had a sudden idea that just wouldn't go away. Grinning viciously, he pointed at Rias, causing the Gremory Heiress to freeze up as he turned the pointing finger around and curled it back towards him. Akeno let out a mewl of protest as Rias jumped to her feet, running over to him as fast as she could, her bountiful chest bouncing up and down as she came.

Once she was there, Issei pulled her close, giving her fine ass a squeeze and leaned in to her ear, murmuring his instructions to her. Rias listened carefully and when he finally pulled back, she had an impish grin on her face and a mischievous glint in her eye. She glanced back at a suspicious, curious Akeno and then looked up at him and nodded.

"It will be done… Master."

Issei's cock twitched at the word, even as the Gremory Heiress skittered from the room, not even bothering to get dressed as she went off to do what he'd commanded of her. The young man watched her go for only a moment before turning back to Akeno and smiling wickedly.

"Assume the position slut."

Akeno immediately got onto her hands and knees, no further instruction required. She then fell off her hands and onto her face, holding her ass up in the air and looking back at him as best she could as she moaned, jiggling the big fat bubble butt back in his direction. However, this time Issei wasn't aiming for the cunt. He had another hole in mind to amuse himself with as he waited for Rias to return.

As seductive and flirty as she tried to be, Akeno was not prepared when Issei used his hands to spread her ass cheeks apart and then crouched down over her to guide the tip of his messy cock, lubed up with a combination of his and her friends' juices down into her tight butthole. The dark haired devil's eyes widened dramatically and she let out a bit of a squeal as her legs kicked back and forth ineffectually behind him.

Issei just grinned wider and kept on going, feeding inch after inch of his massive slick member into her back door, pressing past her sphincter with only a small amount of difficulty and then beginning to fill up her ass with his shaft. Akeno whimpered and whined, the mask completely falling away to reveal the vulnerable girl that lay underneath.

"I-Issei p-please, you're too big…"

Issei paused for a moment and cocked his head to the side, his shaft half lodged in Akeno's ass. Then he leaned down, speaking down to the ear on the side of her head that was pointed up towards him.

"Are you sure Akeno? Did you not know what hole Rias was using to pleasure my cock when you three walked in on us? Your friend was able to take all of me up her ass. She loved it. But I suppose if you can't handle it, I can always go find Rias and have her take care of me."

Akeno tensed up and a moment later she spoke in a quiet voice.

"… Keep going."

He couldn't resist though, all the teasing Akeno had put him and others through before he'd unlocked his true potential and finally taught her a lesson made him want to give her a little back. Staying still, Issei grinned down at the beautiful buxom young woman.

"Sorry, what was that? I suppose I'll stop them, Rias will be so dis-"

"I SAID KEEP GOING!"

She practically hollered the words out, shivering and shuddering under him as he grinned viciously and gave her exactly what she asked for. There were no more words after that, just the squelching sound of his massive member plowing her stretched asshole and the sounds of flesh smacking against flesh as Akeno's voice filled the room, her whines, whimpers, moans, and groans music to his ears. Issei was panting as he roughly fucked the big bubble butt before him, but when he looked up after a while, he found Rias there, watching.

The red head was staring at him defiling her Queen with clear and blatant arousal, lust, and envy. She was also holding exactly what he'd asked her to grab in her hands, which meant it was time to bring this to the next level. Issei sped up his thrusts into Akeno's ass and a few moments later the young woman came and she came hard, her first orgasm at the hands of a man coming from a rough and brutal butt fucking.

While Akeno was dazed, Issei pulled out of her ass with a pop, his cock still throbbing and very hard as he planted a foot in Akeno's butt and slowly pushed her over onto her back. Akeno's eyes were glazed over, but she was still quite coherent as she looked up at him with a heavily lidded gaze, her lips parted slightly and her face flushed with desire for more.

Issei snapped his fingers and held out a hand. A moment later, Rias was at his side, holding out the chain he'd had her retrieve. Issei didn't know or care where the crimson haired heiress had gotten it; all he cared about was using it. Falling to his knees before Akeno, he spread her legs wide and moved between them, the tip of his cock brushing against her pussy lips. Even that simple contact caused Akeno to shake a little, experiencing a mini-orgasm as she moaned wantonly and tried to hump her hips towards his member to get him inside of her virgin hole.

But that wasn't in the cards, not yet. Issei grinned viciously and kept his cock out of reach as he grabbed one of Akeno's large tits, groping and gripping it with his large masculine hand. The dark haired girl moaned again, writhing and squirming under him in a delightful way as he practically mauled her breast. Eventually though, Issei gripped the thing at the base, his fingers encircling her nipple, pinching at it, elongating it. Once it was standing out, Issei brought up the needle at one end of the chains and before Akeno could even figure out what he was doing, the draconic young man used a miniscule bit of his power to send it right through her nipple.

A cry of pain mixed with pleasure escaped Akeno's throat and she shivered as a small rivulet of blood dripped from the puncture wound. Issei wasn't paying attention to that though; he was already moving onto her other nipple and doing the same there. Akeno didn't cry out this time, just mewling pathetically as she watched what he was doing from her position, eyes wide and filled with lust.

With her nipples interconnected by the chain, Issei brought the third bit, the last needle, down her body slowly, running the sharp thing along her undulating abdomen and down her navel to between her thighs, right at the top of her pussy. There, Issei worked at Akeno's clit, incidentally bringing her to another orgasm until the tiny nub was standing out just enough for him to pierce it was the final needle.

Once Akeno's tits and cunt were all connected together by the chains and needles through her nipples and clit, Issei ran his fingers over the sensitive fresh piercings, exuding just a bit more of his power and healing the wounds over. Akeno's nipples and clit were no longer damaged and in fact, tearing out the needles and the chain they were connected to would actually do more damage to her then anything else. The accessory was essentially semi-permanent for the foreseeable future.

The dark haired masochist breathed heavily as she stared down at herself. Then, Issei reached for the middle of the interconnected chains and gave it a rough tug, causing her eyes to go wide before rolling back in her head as she also threw her head back in the same moment, letting out a moan and climaxing hard just from the exquisite pain he was forcing her through.

It was as she was cumming that Issei finally penetrated her virgin cunt, taking the last purity left in the room and slamming home into Akeno's cunt. Her pussy was tight but also extremely wet, her arousal making any pain that might have come from Issei plowing into her with all of his force into mere discomfort. Luckily for Akeno, he was still tugging at the chain as he fucked her, making for an absolutely delicious combination of pain and pleasure as the sadistic masochist broke under him, her mind shredding around the edges from orgasm after orgasm.

Issei fucked the seizing, spasming girl, grunting in pleasure at her tight pussy walls clenching down around his length. Her asshole had of course been tighter around his massive member, but he was large enough that her virgin cunt felt just as good in a whole other way, even as he slammed up against her cervix, battering at the gates of her womb and preparing to unleash his seed deep inside of her.

Akeno was lost in the pleasure, high on the ecstasy and unable to bring herself back down from the heavens that Issei was forcing her up into. The female devil knew her loyalty should always be to her King and best friend first, but in her heart of hearts, Akeno was pleased that Rias had declared Issei her master, because Akeno was ready to do the same right here and right now. And if Rias had been opposed to it, the buxom dark haired beauty wasn't sure she would have been deterred by that displeasure.

She'd never have to know though, because Issei was more than enough man for all of them. Akeno now realized, with Issei's huge member plowing her senseless right there on the floor of the ORC building, that being jealous or envious of her King or the other girls for getting Issei first had just been foolish of her. There was more than enough of Issei to go around, hell, there might just be too much. He'd fucked his way through Koneko and Kiba and left them insensate, and now he was doing the same to Akeno and he showed no signs of slowing down.

Akeno moaned out wantonly and instinctively wrapped her legs around Issei's torso, pulling him deeper into her and then doing the same with her arms around his neck, dragging Issei down so she could kiss him deeply, passionately. Of course, he immediately dominated the kiss because that was just the sort of man he was. But it was okay because Akeno was the sort of woman who wanted him to take her, abuse her, fuck her senseless. She was overjoyed to have found a man finally worthy of her obedience, of her submission.