Warning: This story is made of pure imagination of the author's crazy imagination, please don't read if you're not of age yet, or have problem control your imagination. The author of this piece of art does and will not encourage such things being done by those who mentioned above in real life. I strongly discourage 18- from reading this.

Also for those who are 18 plus, this story contains sexual material not suited for morons that can't tell fantasy from reality. This is a work of imagination like belly bulge, massive dick can release gallon of cum and unholy stamina so don't ask me why I put this warning.

Summary: Smut. In this story Issei, formerly known as Issei Gremory is the Maou Lucifer of the Underworld. Behind a kind and caring leader of a faction is a pervert, oppai-loving playboy who loves to fool around with woman, even if he is married. Whoever said a Maou can't have a harem? It won't hurt if no one knows about it, right? Issei/Harem. Warning: Hardcore and Incest.

All High school DxD characters, plot other than the AU universe of this fanfic… rightfully belong to Ichiei Ishibumi-sensei.

Issei Lucifer: The (secret) Playboy Lucifer

Chapter 6

Work and Sibling love

Sitting comfortably on the sofa in a high class hotel suite, Issei patiently waited for his client to arrive.

He was a Maou, one of the four leaders of the Devil Faction, so he didn't have to do Devil Jobs. However, they were something he had greatly enjoyed doing back then when he was younger, regardless of what they had been. In addition, his most favorite kind of work had been fulfilling sexual requests, because they had been his opportunities to have one-night-stand kind of sex with beautiful and attractive women without a care about later entanglements, as all that mattered were pleasure and satisfaction.

After he had become a Maou and married Grayfia, Issei didn't have much free time to answer these requests anymore, but recently he had his wife rearranged his schedule and had his Sunday's night completely free for them. Those old geezers on the top knew about this, but it wasn't like they could do anything to stop him from answering them. Women, devils or whatsoever, who were rich enough to afford his service were usually extremely powerful and politically had a lot of influences over their respective groups, so having Issei, one of their leaders, fulfilling their demands, sexual demands but still pretty much demands, could be a perfect opportunity for the devils to strike financial, political… deals with their factions.

Tonight was no exception, after having Grayfia and Kuroka going through the mountain of requests that had been sent from all over the world with him, Issei had chosen his ideal partner for tonight and contacted her to meet him at one of the fanciest hotels on the human world, near her house. Putting on something formal and pretty decent, Issei had headed there first, accepted his room for the night and waited for her to arrive. It shouldn't be long, because she promised she would be there by seven.

And she didn't disappoint him.

Hearing the doorbell, Issei stood up and went to open the door, coming face to face with the lady who was going to share a steamy hot night with him tonight. She was very beautiful, having the appearance of woman in her mid-twenties. She had light skin, long and wavy blue hair with purple eyes and large J cup breasts that daringly stood on her chest without a care about the law of gravity. She dressed to impress and to kill, with her outfit being a red, strapless dress that was also specifically a mini-dress in length, with black hem which barely covering her generous cleavage. Wore outside of her dress was a black coat with sparkles and blings with light tan fur on the collar. Her nails were polished red, and she also sported a pair of golden, made-of-gold heart-shaped earrings and a matching heart necklace, thin and small, to go with it. She also carried a small handbag with her.

Overall, she was a woman that men would kill to fuck. Her name was Ageha Kurono, a high class member of the Succubus race, the race of sex demons. He had always wanted to have a night with sex demon, directly. Having heard and read so much about them in his past life. Since his past self had already had multi encounters with them in the past, he knew that their basic powers didn't work on him, so Issei knew he could thoroughly enjoy Ageha without a care.

"Hi! Good evening!" The woman greeted him with a seductive smile as she ran her hand through her blue hair "I believe this is the first time we have met, Lucifer-sama."

"Yes, of course… and Issei is fine, Kurono-san." Issei smiled as he stepped to the side and made a path for her to walk in.

"Then Ageha should be fine." She said, smiling as she turned around to face him "It's an honor to finally meet the famous Lucifer Satan in person." She lowered her body, but Issei could see that she was purposely showing him her cleavage.

"The pleasure is all mine, Ageha-san." Issei took her hand and placed a kiss on the back, smiling at her "You look gorgeous, by the way."

"What a gentleman, Issei-sama! You don't look so bad yourself." She smiled in satisfaction, nodding her head before turning her head around to look at the room he had chosen for them "You have great choice, Issei-sama, even I have never been here before." She said, walking around the room with Issei following behind her.

"I only want the best for my lovely client."

"Just how many women have you taken in here anyway?" She asked playfully and put her bag on the bed before turning around to look at him "No ill intent, of course."

"To tell you the truth, you're the first I brought here." Issei admitted with a smile "It usually happens at my palace or my clients' palaces. I want tonight to be a bit… special."

"Reason?" Ageha asked, leaning closer.

"A lovely lady such as yourself deserves it." He flirted coolly, wrapping his hand around her waist and pulling her closer "You're my client for tonight, Ageha-san, so do not hesitate to ask for anything you want."

"Then don't forget that I'm a succubus, Issei-sama." Ageha licked her lips as she rubbed her soft body against his muscular one before leaning her head slightly so Issei could lower his down and kiss her. Parting his lips, the brown haired Maou moved his tongue into her mouth, and she welcomed it wholeheartedly with hers. His hand went lower, and he could feel her do the same. As he groped her ass, he could feel her hand slide into his pant and go for his dick. Issei could feel her gasping lightly into his mouth when her hand touched the sleeping monster between his legs.

"Now this is what I call a devilish package." Ageha said breathlessly as he broke the kiss and stood there letting her stroke his limp cock with a casual smirk "I must be third luckiest girl of the week." She took her hand back and licked it.

"Only third?" Issei asked.

"The first is your wife, the strongest Queen Grayfia Lucifuge and the second must be Akasha. I guess as your first and second wife, they must have their fills of yours every night." She said and continued with a smile "In case you are wondering, I know Akasha. She's the mother of my daughter's friend at high school. They are chasing after the same guy there."

"Oh, now that you have mentioned it, I believe I must have seen him and the crew when I rescued Akasha from Alucard five years ago." Issei nodded his head thoughtfully while looking up and recalling the battle against Court Dracula. With a smile, he then turned back to her and gestured his hand toward the door "Anyway, why don't we head down to the hotel's restaurant and have dinner? I have booked a table for two for us there."

"Ara, why don't we just start the night already? You know what Succubi eat for meals, right?" She asked seductively, but then said "But of course a man's gotta to eat. It's going to be a long~ night for the both of us, after all." Issei could only nod his head in agreement and put his hand on Ageha's hip, guiding her out of the room before heading down to the restaurant.

Forty five minutes later, the two returned to their room, but as soon as they had gotten out of the elevator, Ageha grabbed him by his collar and pulled his mouth toward hers in a searing kiss. As they furiously made out with each other while groping each other's body, it took Issei sometime to open the door and get them into the room, kicking it close with his foot.

Then suddenly, she pushed him back, making Issei fall into the sofa behind him. Smiling seductive, she reached her hands up and slid her coat down her shoulder, before letting it fall to the floor "Let's get this night started, shall we?" She asked and took a step closer, standing right in front him. Grinning, Issei put his hands on her waists and slowly ran them down to her hips, trailing along her deadly curves "You like?" she asked, lightly swaying her hips around as he pulled his hands up and went under her skirt, squeezing her thighs before stopping at her ass.

"Very." He admitted truthfully. His eyes were focused on her J-cup boobs.

"You're a very honest man, aren't you Issei-sama?" She asked, giggling slightly before saying when she felt his hand wrapping around the waistband of her underwear, a small thong "Pull it down." He did what he was told, and slid it down her thighs, down to her long legs and removed it from her body completely "Can you do the same for this?" Ageha turned around and pulled her hair to the side, showing him the zipper of her dress. Smirking triumphantly, Issei stood up and reached for the zipper before slowly pulling it down, exposing her back and loosing her dress. The zipper stopped just above her supple ass. As she kept the dress from falling off her body with her hands crossing on her breasts, Issei lowered his head down and kissed her neck, holding the succubus by her shoulders. Issei then kissed down to her back, before trailing his lips up to the back of her neck, causing the blue haired woman to moan in response.

Stepping forward, Ageha removed her hands from her chest and let it fall down to her waist, leaving her torso naked. As she moved while swaying her hips, she slowly pushed her dress down, seductively showing him her round ass before dropping it on the floor. Now naked, Ageha continued to move forward until she was by the window, turning around and allowing Issei to take his time drinking in the sight of her voluptuous succubus body, especially her beautiful breasts.

When she made a come over gesture with her finger, without wasting for a second, Issei approached her while removing his shirt. Standing in front of Ageha, Issei reached his hands out and groped her breasts from below, squeezing them in his palms and feeling amazed by the softness. As she leaned her head back, giving him more access, Issei leaned his head forward and captured her left nipple into his mouth, using his tongue to tease the hardening teat, causing Ageha to moan even louder before raising her hands and pushing her tits together for him. Issei accepted the treat with gusto, moving from one to another, while simultaneously molding her tits the way he wanted.

Forcing his head away, Issei stood straight up and kissed Ageha, holding onto her large breasts as he snuggled his tongue into her mouth. The two made out passionately before Ageha moved her hand down and proceeded to remove his pants, getting it down to his thighs and freeing his cock from its confine in only a few seconds. Wrapping her hands around the base of his cock, her fingers couldn't meet around his girth, Ageha started stroking it in rhythm with their heat kiss, her other hands went down to cup his sperm bloated sack, massaging his heavy balls.

Breaking the kiss, Ageha pulled back and waited for him to get himself completely naked to kneel down in front of him, licking her lips as she faced his semi hard cock. Bringing out her tongue, the blue haired succubus teasingly licked the head of his cock, before opening her mouth to take it in, sucking on it lightly before releasing it with a wet kiss.

Holding the impressive man meat with both hands, Ageha traced circles around the head with the flat of her tongue, making Issei grin in approval. Not breaking eye contact, she took three inches of his hard dick into her mouth, slurping lewdly as she moaned in lust at the taste of his delicious cock before releasing him again.

"Now, aren't you such a tease?" Issei asked as he put his hand on the top of her head. The inside of her mouth felt incredible, was the only thing he could describe how good it felt.

"I thought this night was all about me, since I am your client."

"And I still remember that you are a Succubus, Ageha-san." Issei grinned lecherously as he rubbed his cock against her face while she was trying to drench his balls in her spit using her tongue and mouth "Start acting like one, and I might give you a discount next time."

"How can I say no to that?" She said, kissing his cock before taking it into her mouth. When the tip touched the back of her throat, she didn't stop and continued to push forward until she had taken two third of the monster down, making him go cross eye as her gullet clenched tightly around his dick. Sucking like a vacuum, Ageha pulled her head back, nearly extracting his throbbing organ from her gullet, before pushing her head forward, taking nearly his entire cock down her throat, causing Issei to shudder in pleasure. She repeated the process over and over, starting slow but gradually picking up to pace. When her nose finally touched his crotch, Issei nearly lost it and almost blew his load, but kept his composure and stayed strong like that for half an hour long.

Eventually, the building pleasure became too much, and with a groan, Issei blew his first load of the night down her throat after ramming his cock as far down her gullet as he could, overflowing her inside with torrent of thick hot sperm. Issei didn't hold back, and fully enjoyed the pleasure of ejaculating down a succubus' throat. He continued to hose his seeds like that for awhile, forcing Ageha to swallow more cum than she had ever done in her life, before pulling back and letting the head of his cock rest inside her mouth when his orgasm became less intense. Instinctively, she started gulping down his cum once he filled her mouth completely, moaning loudly at the taste. Glancing at the clock, she couldn't believe that he had cum for fifteen minutes straight, and when he was done, his cock was still as hard as steel, urging her to give it another service.

Taking his cock back, Issei watched Ageha as she savored the glob of his sperm with her tongue before swallowing it down in one gulp.

"Delicious." The sultry succubus commented as she wiped the corner of her mouth with the tip of her finger "I have never had such a high quality cum like that before, you are truly blessed with sexual prowess, Issei-sama." She stood up and kissed him before turning around and putting her hands and one foot onto the window frame "I believe I deserve an oral service in return, don't I?" She asked, shaking her as she stuck it out and exposed her dripping pussy.

Issei knew it was his turn to get on his knees, and he did it without hesitation. Kneeling behind her, Issei grabbed her butts, loving how his fingers almost seemed to sink into them. He then moved a hand to her pussy, and inserted two fingers into the hole, causing her to moan in response. As he fingered her pussy at a steady pace, he moved his face forward and licked her ass crack, making her sudden when his tongue gazed her butthole.

Then, without a warning, he drove his head forward and tongued her anus, causing Ageha to gasp in surprise. He continued like that for a few more seconds, before switching his tongue and fingers' positions with each other, licking her pussy while fingering her ass, sending waves of pleasure through her body.

Moving his hands to her butt and holding them with both hands, Issei then drove his tongue into her snatch and started tonguing her inside, lapping the love juice that kept rushing from her core, making Ageha moan loudly in bliss. Succubus' juice was the world's most natural aphrodisiac, so the more he drank it, the hornier he became, but Issei managed to keep his cool and continue pleasuring Ageha for awhile before she came and flooded his mouth with her juice, which he managed to gulp down without spilling a single drop.

"That was so good." Ageha moaned as Issei stood up and wrapped his arms around her body, putting his hands on her boobs, massaging them. Feeling his cock rubbing against her ass, Ageha swayed her hips and shook her ass cheeks, smiling invitingly and seductively "Are you going to fuck me now, Lucifer-sama?"

Grinning, Issei positioned his cock at the entrance of her pussy and plowed straight into her in as soon as he had had a firm grip on her hip, stretching her wide open with a squelch. "Aaaanngh." He moaned in delight while moving his hips at a decent pace "So tight. You have a very nice pussy Ageha-san. It's like you're sucking me in, as expected from a succubus."

"Sweet kami you are big." Ageha threw her head back and wailed in bliss "Oh fuck!" She moaned even louder when Issei increased his pace, her gargantuan booty rippled with every impact of his hips. His thick, impressive cock slid in and out of her swollen, silken, wet tunnel, hitting spots that no man had ever hit in before. Rearing back, Issei then thrust forward and punched right through her cervix and deep into her delightful womb, causing Ageha to go cross-eyed at the impact and cum like she had never cum before. Her tongue lolled out of her mouth and her eyes rolled back, finally loosing herself to the pleasure.

Hooking his arms around her elbows and allowing her breasts to bounce free, Issei kept her close to him like that and started up fucking Ageha's tight twat and womb with short, but fast and powerful thrusts, the sound of his hips smacking her ass and her blissful moan echoed throughout the fancy room. As a succubus, Ageha knew she was supposed to be the one who had more control and made him blow his load first, not the one who came once every two minutes and moaned like she was in heat, but in the end, when she was being fucked like that, there was little that she could do.

Not that she wanted to, since being the one who was at the receiving end like this wasn't so bad.

As Issei got closer to a blissful orgasm, he increased his pace, blurring his hips as and fucking the blue haired succubus as fast as he could. Moments later, he reached his limit and came inside her wholeheartedly, holding nothing back. Ageha had a blissful face and came hard when she felt a massive amount of cum, even larger than the one she had swallowed, started filling her womb as the devil leaned his head back and continued to fuck his load into her while grinning lecherously. Once he was done, he slowly pulled out of his client for the night and watched as a huge deluge of cum started flowing out of her well fucked cunt as she fell to her knees, panting.

"No time to rest, Ageha-san." Issei said as he picked her up and carried her to the bed after she had managed to catch her breath.

"The night is still young, why rush?" Ageha asked teasingly as she was put down to the bed.

"Because I don't want to stop fucking you, that's why." Issei smirked as he got between her legs and spread them with both hands on her knees "It's not like I have succubi to have sex with every day, so get ready Ageha-san, unless you pass out, I am not going to stop fucking you until I am I am thoroughly satisfied."

"Oh… my…" Ageha giggled excitedly and reached her hand down to position his cock at her neither lips "Then please, have it your way then. Fuck me unconscious."

"With pleasure." With that, he thrust his dick in and started savagely hammering his cock into her wet cunt.

There was nothing better than a tight, sensitive succubus who liked to moan.

[The next morning]

"So, even succubi at her level have their limit." Issei said as he finished putting on his clothes and turned his head around to look at Ageha, who was laying tits down ass up on the bed with a fucked-stupid smile on her face. Her body covered in head to toe in his cum, but he had shot so much of his seeds inside her that she looked nine months pregnant "Well, our contract has expired." Issei said as he lowered his head down and smiled at her "I hope to work with you again, Ageha-san." He kissed her playfully, causing her to whimper in response.

Standing up, Issei made the teleportation magic circle he had left on the floor flash brightly. With a smile, Issei stepped into it and decided whether or not should he return to his place right away. It wasn't a wise thing to do, because Grayfia was probably expecting him to return to get him back to work.

"Maybe I should pay my little sister and her friends a visit." Issei said to himself before nodding his head sagely in agreement with his idea. It'd been awhile since the last time he had met Rias and the others.

Giving Ageha one last look, Issei stepped into the magic circle he had prepared on the floor and teleported straight to the clubroom of the occult research club, where he was greeted by none other than Akeno Himejima, who at the time was sitting on the longue in the middle of the room and doing her homework. Seeing the arrival of him, she immediately dropped what she was doing and stood up so she could greet him with the respect he deserved.

"Issei-sama." She said, bowing "It's my honor to see you here."

"Good morning, Akeno." The brown haired man grinned, raising his hand to signal her to raise her head up "How are you doing?" He stepped out of the magic circle and approached the girl.

"I…" Before she could answer his question, Issei grabbed Akeno around the waist and leaned his body over to kiss her, shoving his tongue into her mouth. She was surprised at first, but quickly melted into the kiss and returned the favor by entangling her tongue with his. After a minute, he released her, allowing the young woman to catch her breath "I am doing fine… thank you, Issei-sama."

"That's good to know." Issei grinned and looked around "Where are Rias and the others?" He asked, before taking a seat on the longue.

"Rias-sama is attending a meeting with the other clubs presidents." The black haired queen answered with a smile "Yuuto-kun and Koneko-chan are having classes, so they won't be able to come here until noon."

"Oh, I see. I guess I will have to wait for Rias then." Issei nodded his head as he ran his hand up and down Akeno's waist.

"Would you like to have some fun with me, Issei-sama?" Akeno said as she snuggled closer to Issei and put her hands on his chest "Surely I can give you something to fill your hands with while waiting for your sister." She asked, and Issei nodded his head in response with a grin. Smiling seductively, Akeno removed the ribbon and let her hair fall freely down her body, before leaning forward to kiss him slow and passionately. His lack of response at first only turned her on even more. After a moment, Issei grinned into her mouth and began to kiss her back, causing Akeno to moan when he slid his tongue into her mouth. As their tongues entangled, Issei could feel her hands pulling down the zipper of his pants and freeing his semi hard cock soon after, her fingers couldn't meet around the impressive girth. She stroked his cock with earnest before taking out his balls and starting to play with them with her other hand.

Breaking the kiss, Issei then spread his legs, signaling Akeno to slide down to the floor. She did it without the need to be told twice, and took it into her mouth, sucking while swirling her tongue around the head before taking it deeper down her throat. It didn't take it long for him to become rock hard in her mouth and when he did, Akeno's hands let go of his cock and went on to remove her shirt before unhooking and doing the same to her bra, allowing her breasts to bounce free.

"You're one hungry slut, aren't you Akeno." Issei said in admiration at how greedily the black haired queen was trying to swallow his cock as if trying to stuff all of it in her stomach. Grabbing her hair to her liking, he pulled her head back and forcefully removed his cock from her mouth "You know, you should hang around my place more often, give you more time with your mother, and me."

"Yes, I would love to, Issei-sama." She purred in response, kissing the tip of his cock before grabbing two handfuls of her enormous breasts and wrapping them around his cock. Smiling seductively, she slid them up and down, pleasuring him with the parts of her body that he loved the most, earning a moan from him in approval.

"Fuck, that's it. You are getting better and better, Akeno." Issei moaned as he released her head from his grip "Keep this up and I might even arrange a night with Grayfia for you." Knowing how much the girl idolized his wife, it could be the best idea ever. Even Issei couldn't stop himself from giggling perversely at the thought of having two busty queens on the same bed.

"Thank you, Issei-sama." After saying that with sparkling eyes, Akeno went back to pleasuring him with her mouth, taking the part that not even her big tits could cover. She moaned passionately around his shaft, before submitting as Issei began to move his hips in sync with her breasts and mouth, holding Akeno by her hair. Since he had already had a lot of sex last night, Issei was able to last really long against Akeno's assault, but eventually his balls tightened and his cock swelled in her mouth. With a loud groan for a warning, Issei flooded Akeno's mouth with a massive helping of hot cum. It took a moment for his orgasm to end, allowing Akeno to slide off his dick "Mmmmm, thank you for the delicious load, my lord." Akeno stated sultrily before placing a wet, slopping kiss on his cock, causing it to throb in response.

"Not bad for me to start a day." Issei said as he leaned his head back and enjoyed the pleasure of Akeno's oral service.

"What do you want to do, Issei-sama?" Akeno purred seductively as she wrapped her hand around his cock and stood up to press her mouth against his. They kissed for a few seconds, before Issei suddenly forced her back with his hand on her neck "Ah, Issei-sama~!" Akeno moaned as he applied some pressure on his grip.

"With a kinky slut like you, Akeno-chan, there are so many things I want to do to you." He said, smirking while teasingly kissing her "But first… I have already told you peaking is very bad, haven't I…Rias-chan?" He suddenly asked loudly and turned his head to the door of the Occult Research Club's clubroom, where its president was kneeling on the floor at the other side, looking at them through the very small gap between the door and the casing.

"Ara ara…." Akeno gasped before starting to giggle uncontrollably (her hands hadn't stopped moving).

"Why don't you come in, Rias-chan?" Issei grinned "There's no point in hiding yourself anymore."

Line Break

When Rias Gremory arrived at her clubroom and saw her queen/best friend sucking her brother off, she wasn't surprised.

In the end, how should feel surprised, when she grew up getting used to seeing him fooling around with women who weren't his wife, Grayfia Lucifuge, and building a harem of beautiful and attractive women out of his peerage. In the society of devils, a Maou wasn't allowed to have a harem, but it didn't take a genius out of Rias for her to see Issei Lucifer had never seemed to be restrained by it.

No, she was annoyed… and jealous.

Why? Because Rias was in love with her brother. She didn't know how, she didn't know when, but for as long as she could remember, she had always had a strong affection for him. Aside from his usual antics, Rias grew up admiring her brother, who loved her dearly and cared for her well-being, even though as a Maou he could never favor a devil over another. That feeling had grown stronger when he managed to convince their parents to cancel her engagement with Raiser Phenex, giving her the opportunity to find happiness.

"But first… I have already told you peaking is very bad, haven't I…Rias-chan?" Rias almost flinched when she heard her brother calling for her "Why don't you come in, Rias-chan?" Without any other choice, Rias pushed open the door of her clubroom and stepped in, doing her best to ignore the sight of his massive cock "Good morning."

"Good morning, Onii-sama." Rias greeted him, doing her best to keep her voice normal "How have you been?"

"As you can see, I am all good." He replied with a grin "What about you, how…"

"Can you…um… put that away first?" Issei looked at his cock when Rias pointed her hand at it and requested nervously.

"Oh…" He said. However, his cock was too hard to be return into his pants, so he went for the next best thing "Akeno-chan, would you like to help me?"

"Of course, Issei-sama." Akeno said knowingly and climbed onto his lap, impaling herself on his cock before using her skirt to cover the rest, earning moans from both of them "There you go, Issei-sama." Grinning, the brown haired Maou gave her a thumb up as Akeno wrapped her arms around his neck and pressed her breasts into his chest.

"Akeno…" Rias muttered in annoyance.

[Insert scene here-Waiting to be edited. Y/N: Sorry guys, but I am still trying to figure it out a way to make the conversation between Issei and Rias as good as possible. Since I cannot delay the update any longer, I have decided to leave it like this and add new part when I update new chapter. Please forgive me for this, but I don't think I have any other choice.]

Line Break

Issei wasted no time after he had finished with Akeno, who was left with a pregnant-like belly, and took the two of them to Rias' apartment via teleportation magic circle.

The moment he had been waiting for had finally arrived, and he knew he was going to enjoy every second of it.

"Are we…" Without giving her the chance to finish her question, Issei turned Rias around and kissed her, catching the young lady by surprise. Rias was a little hesitate, at first, but quickly steeled her nerves and kissed him back, submitting to the kiss and closing her eyes and letting her brother explore her mouth, which unknown to her wasn't the first time. The two moaned as their kissing started to heat up, one of Issei's hands soon found its way up her body and ultimately filled itself with her right breast, while the other trailed down to her ass and did the same to her supple butt through the silky fabric of the panties she was wearing.

Rias gave no objection. She was new. She was inexperienced. Everything she knew about sex was through movies, porn, and also her secret collection of hentai anime. She wanted to make the best of it, but she didn't want to mess up, so she allowed Issei, who had so much experience already, to take the lead. While still kissing her, Issei unbuttoned her shirt, and removed it from her body. He quickly did the same to her lacy bra, and freed her breasts from its binding. Next, he broke the kiss and latched on them like a hungry animal. Using both hands, he kneaded and played groped her breasts the ways he wanted, his sucking mouth sealed firmly around her nipple, and only broke away when he decided to move onto the other, earning moans and gasps from Rias in response. Rias could only stand there and let him enjoy her body, so aggressive that he pushed her toward the bed and made her fall on her back, with him on top.

"You really love breasts, don't you onii-sama?" Rias asked, arching her back in pleasure.

"Yes, and I like them best when they are big, soft and bouncy." Issei replied as he broke his face away from her chest and shot his head forward to kiss her "Yours are simply the best."

"I bet you said that to every woman you brought to your bedroom." That was not a question, making Issei respond with a chuckle "Pervert…" She stated with a pout, but before she could say anything else, Issei sealed her lips tight and shoved his tongue into her mouth, preventing her from uttering another word. As Rias once again struggled to keep up with her brother, Issei used his magic to remove his clothes, allowing his semi-hard dick to spring free and leaving him completely naked on top of his sister.

"I am." Pulling back, Issei told her with a sly smirk before standing up and straddling her torso. Her eyes followed his movement, and immediately glued to his cock when it had finally come into her sight "Now, the moment of truth." He declared happily. This was it. This was the moment he had been waiting for, and without waiting for another second, he grabbed her tits and smashed them together with his cock in between, moaning at the amazing softness around his cock "Fuck…" He whispered in amazement and moved his hips just a few times for a quick test. The feeling was beyond what he had imagined.

Rias looked at the pleasure expression on his face and, for some unknown reason, couldn't help but feel proud of herself. As he moved his hips, allowing his cock to slide between her tits soft embrace, she could feel the engorged head of his cock rubbing against her lips and nearly poking against her nose, smearing a fair amount of hot pre-cum around that part of her face. She opened her mouth, and licked her upper lips, having a taste of his cum on the tip and then all over of her tongue. It tasted nothing like she had imagined, but Rias believed she had finally known why his maids, even Grayfia, loved spending their times under his table.

"A much bigger treat is waiting for you." Issei said as he stopped his hips and started moving her breasts up and down his steel hard dick "Suck my cock, Rias." He told her with a hint of authority in his tone, and Rias could only nod her head in response. He was her brother, but incest was just a word in the society of devils, and who was she to defy a wish of a Maou?

Opening her mouth, Rias took in the bulbous head of his cock, and found herself slurping on it a second later, her tongue madly licking his slit and around the glans of his cock. Issei leaned his head back, and pushed his hips forward slightly, cramping more of his cock into her mouth. Rias gave no objection, and continued to suck and lick the part of his cock that was inside her mouth. She didn't know how to do it probably, so he had hit her teeth a couple of times, but Issei didn't mind. Back in the old world, he had imagined Rias would be like this during their first time: eager but sloppy (which could be said the same for his). She might be a she-devil who had acted seductive and worn skimpy lingerie around him, but in the end, she was just another innocent teenager to love, and anything that would involve if they had decided to take the next step.

He was a pussy and a fool back then, he had to admit. The other girls were a different story, but Rias and Akeno had made several attempts to sleep with him, and he had refused them because he thought he didn't feel like he had earned the right to do so. Two young and beautiful women would do anything to please him, and yet he had decided to spend the majority of his time feeling his youth, aka jacking off to their naked images and the fantasies of having sex with them in his head. Sure, that bitch Raynare, who he was eager to meet as soon as she decided to make a move at Kuoh for whatever reason it was going to, had a hand in his feelings, but he wouldn't deny the fact that he had been very pathetic back then. Ophis and Great Red resetting the world simply gave him a means to maintain peace, and what it takes to archive his own happiness.

Looking at the woman who was having her breasts embraced his cock, and sucking on one third of the same thing, he couldn't help but feel amazed at the feelings she had for him. (As it had been said before, the two dragon gods had made sure to keep the feelings of the girls he cared about at unconscious-level). Her love was so great she didn't have a single problem admitting her love for him even though in this world he was her biological brother. Sure, there was no such thing as incest when you were a devil, but logically that had always been a questionable subject whenever you were a living being.

Thick meaty slaps filled the room as Issei started fucking her tits for real, drastically moving his hips back and forth with his cock secured in a tight grip of her tits.

"Fuck Rias-chan! Here I come!"

Issei felt his balls tighten and Rias could feel his cock swelled even bigger inside of her mouth. She braced herself for it, but she didn't expect him to release her breasts and shoot forward to grab her by the back of her head to raise her head up before pushing his cock deep in her throat to come. Rias did her best to swallow, but she couldn't even swallow half of load before the next followed, causing his cum to spill out from the corners of her outstretched mouth, making a mess on her cheeks and the lower half of her face.

After a moment, Issei pulled his cock out with a wet pop and kept her head where it was, jerking his cock a few more times before painting the rest of her face white in his cum. After he was done cumming, Issei allowed Rias to suck for the last helpings of cum before sitting down at the sight, sighing stupidly in satisfaction.

"Man… that was…" But before he could say that, Rias sat up and shot her hand out to pinch his cheek, glaring at him with a cute pout "Ouch… Ria…han…It…hurt…" Actually, it didn't hurt that much, since it was nowhere near Grayfia's level, but he still had trouble talking with his cheek being pinched like that.

"What was that at the end?" Rias asked with half lifted eyes and an evil smile "Did you want me to drown in your cum or get suffocated to death?" Her other hand went down and took hold of his balls, massaging them a little harder than his liking.

"I… don't see the problem." He grinned when Rias released her hold on his cheek "Don't tell me that you don't like it, Rias-chan." Saying that, Issei moved his hands under her skirt and grabbed the waistband of her panties, tearing it apart before pushing her down to the bed with his whole body. Lying on top of her, Issei rubbed her outer lips, feeling how wet it was before inserting his middle finger into her pussy.

"Tight and wet, just the way I like it." The brown haired devil commented as he felt her wall squeezed tightly around his finger.

"Then what are you waiting for…" Rias said between moans "Put it in already."

"Impatient, aren't we?" He smirked "Well then…" Removing is hand from her fold, Issei took hold of her thighs and spread her legs apart, allowing him to position himself underneath her. Rias hips raised and aligned to receive his cock wholeheartedly "Let me warn you though… it's going to hurt a lot. Are you ready?"

"Yes." Rias nodded nervously. Without further ado, Issei thrust his hip forward and buried four inches of his cock into her pussy, breaking through her hymen rather viciously and causing Rias to groan in pain. Despite the wonderful feeling of her pussy, Issei didn't move and allowed the pain to ease down and Rias to get used to the monstrous size of his cock.

Still, like any she-devil he had fucked, it didn't take it long for the pain of having her hymen broken to disappear completely. When painful groan became moan of pleasure, Issei started to move his hips, nearly pulling his cock out before thrusting forward, adding two more inches. Rias' pussy was tight, there was no doubt about that, but she was wet enough for him to move in and out of her easily.

"C-can you move faster?" Rias asked, putting her hands on his shoulders to brace herself.

"As you wish." Grinning, Issei fulfilled her wish, moving his hip a little faster and gradually building up speed. Bending his body forward, Issei used one hand to grab and tease her breast, while the other one was still holding onto her left leg. Rias' right leg immediately shot up and wrapped itself around his waist as his thrusting became wilder and his cock got deeper into her.

"Ah… ah…" Rias moaned out loud as the cock of her brother finally reached the deepest parts of her pussy and hit against the entrance to her womb with each thrust. The feeling of having her inside violated by his cock was simply amazing.

"Fuck..." Issei moaned as he focused on moving his hips while his hand seemingly sink into her incredibly soft and large bust as he grabbed it roughly. Her back arched as Issei started to have his way with her at his normal speed and strength, drowning her in the pleasure. The young crimson haired woman couldn't even form actual words as she started come harder and faster than she ever had from fingering herself or 'playing' with her queen while fantasying about her brother "This feels so good!" Issei yelled as he threw his head back and turned his hips into a blur, punching through her cervix and got plenty of his cock into her womb, causing Rias to cry and cum harder than she had ever done before.

It took a good forty or more minutes before he finally felt his balls clenching and his cock throbbing uncontrollably inside Rias' pussy and womb. With one final thrust as far into her as he could, Issei let loose a powerful dose of hot and thick cum into her womb, filling it to the brim. He stayed like that for over eight or so minutes, before pulling out while still coming and spray several ropes onto her face and breasts, once again painting them white.

"You're mine now, Rias-chan." Issei grinned as he continued to stroke his cock and pour his cum onto Rias' body, which was still twitching and jerking every now and then due to the aftermath of her mind-blowing orgasms "Ready for the second round?" Issei grinned, cock twitching.

Rias could only whimper in response as Issei picked her up.

End of Chapter 6

Here you go… sorry for taking this long to update. It took me awhile to get this chapter done, especially when my computer broke a few days ago and I was kind of busy with the more serious stories.

Anyway, here it is folks, I hope you have enjoyed this chapter.

Ageha Kurono is from Rosario Vampire. Since Akasha has already been added, why not bringing in other characters as well?

Well, that's it for now.


Ja ne!

P/S: Would you like it if I take this story to a more serious direction?