Chapter 4: The King of Harem

[Timeskip– 9 years later]

"Alright ladies… line up and take my cum." Issei Hyoudou announced loudly and abruptly pulled his dick out of his MILF of a wife's tight little pussy and stood up while jacking his cock furiously in his hand. The entire group of his lovers, including Grayfia lined up the way he wanted them, with their arms wrapped beneath their tits, pushing their huge racks upwards and their tongue stuck out of their wide open mouth. Issei then felt his balls tensed and within a second or two, groaned as he pointed his cock downwards.

Grayfia moaned in delight as the first thick ropes of cum erupted from his cock and splashed on her face, as it was so large that it ran from her face, down to her neck and pooled in her cleavage, coating her upper body in a huge mask of white sperm. The next load went across Kuroka's face and round tits, glazing them with a thick spread of jizz, making the mischievous cat girl meow out in delight at such a treat of milk from her master. Next, he aimed his cock at Tiamat, who was kneeling at Grayfia's left and unleashed a fountain of milky white jizz across her face, the pent-up torrent of cum covering her mounds, rolling down to her flat toned stomach through the valley of her breasts.

Issei gave the next few jizzs to another MILF, who kneeled behind Grayfia with her giant tits rest on his wife's head, giving him a very seductive, almost sickening sadistic smile. Said MILF was none other than Shuri Himejima, former lover of Vice Governor General of the Fallen Angel Baraqiel and Akeno's mother, who chose to become his servant, his Pawn to repay him after he saved her and her daughter from the people of her own clan. Issei didn't expect Shuri to fall in love with him a couple of months after both mother and daughter came to live with them, but in the end he couldn't refuse such a beautiful and attractive woman like her. The fact that she looked so much like her daughter made thing even more exciting for him.

The two of them usually engaged in SM acts together, and despite their status, he was usually be the one who got tied up and wiped around by his Pawns. It wasn't like he had any objection because it brought new thrill to his sex life, but as a dragon by nature he didn't want to get dominated by anyone, especially the female.

Let's just say that he brought an M out of an S, and sexually punished her senseless with his big dick.

Of course, Baraqiel wasn't happy with the fact that the leader of devil was screwing his former lover… and soon, his daughter.

The next woman who got her face and tits full of his cream, was yet another extremely voluptuous woman with the beauty far surpassed any other, rivaled only by the other ladies of his harem with long pink hair, green eyes and creamy white skin unlike her kind, Akasha Bloodriver. She was a powerful Shinso Vampire who nearly gave up her life to protect the world from Alucard, formerly known as Court Dracula before his kingdom was destroyed, who intended to destroy the world in seven days but was stopped by Issei and his peerage five years ago. Issei, with Grayfia at his side, single handedly defeated the giant creature that the first vampire had become, saving the world. The Vampire Factions, Carmilla and Tepes, were extremely grateful for his help and decided to marry Akasha to Issei, as his concubine in order to bring the two races together, despite the fact that she's already married to Issa Shuzen and had with him a daughter, who was nine year old at the time.

Of course those prideful vampires would do something like that because while one of the most powerful, Akasha wasn't a natural born vampire and their nature didn't allow them to accept such thing like that. Issei accepted her with open arms, and even though Maou wasn't allowed to have a harem (till that day, Issei still believed that it was a bullshit law) the higher-ups had also admitted that it was an opportunity too good to miss. An alliance with the vampire, one of the most powerful Youkai would make Devil a fearsome race to the other Factions. Akasha was also the leader of the legendary three dark lords, whose powers rivaled even the leader of Youkai Faction, the Kyuubi Yasaka herself.

It was a marriage on papers only, but Issei came to love Akasha just as much as he loved the other and the same could be said to the young Shinso Vampire. Issei decided to make her his Rook with a mutation evil piece a couple of months after their wedding, and she had been loyally serving at his side since then.

Last but not least, the one who took Issei his last Bishop to turn her into his servant was a woman that was called the most powerful magician the world had ever seen, Irene Belserion. Just like any women of his peerage, she was a very beautiful and extremely voluptuous young woman, with big breasts, wide hip, and beautiful scarlet hair that was thickly braided and located in the front and back of her body as pairs. Issei met her a few years back when he decided to make a new pact with magic user, and Irene became the one who he made a ten years contract with. One thing led to another and the next thing he knew, she was on her knees sucking his cock, and just like that became one of his many lovers before he decided to make her his servant.

Like Tiamat, she was given the title of strongest as soon as devil society learnt about it.

He couldn't help but grin like an idiot at the thought of how his life had turned out.

Again and again his cock lurched in his hand, delivering streams of sperm all over them, coating their faces and their tits in his dick juice, and the women could do nothing more than quickly lapping, scooping and sucking it up into their mouth, as he finally stopped after half an hour straight of nonstop cumming. Issei groaned when Kuroka reached out and pulled him closer, guiding his cock to her mouth where she sucked and licked it clean for him.

"You have done it again, darling." Grayfia giggled softly as she stood up and wrapped her arms around his neck, pressing her large breasts to his chest "I'm so disappointed in you right now, master." She then pressed her lips against his, kissing him passionately before leaning back so he could feast on her breasts, which had grown a cup bigger after she gave birth to their son, Millicas.

"It's morning already?" Akasha asked a lout as she looked at the clock before massaging her forehead when she was suddenly hit with a slight headache "He's really done it again." The pink haired vampire moaned, as sperm was steadily flowing out of her pussy and asshole, just like the others.

"Like a dragon, I suppose." Shuri giggled and licked his cum from the tips of her fingers, nudging Tiamat slightly and giving her a meaningful wink.

"Are you sure you didn't give him any aphrodisiac last night, Shuri? Because that sounds like something you would do to keep him go forever." Irene spoke up, wiping the last glob of sperm on her breasts, which were full of bite marks and put it into her mouth "Or… he's just that pervert."

"I don't know what about you girls but…" before Akasha could finish that speech, Issei grabbed her around the waist and put her on all four after managing to let go of Grayfia's breast, positioning his cock at her pussy entrance "Ise-sama, wait I'm still…Ah~" the Shinso vampire moaned out loudly when Issei thrust his cock in and started pounding away into her.

"Well, I don't think we're able to leave this place until that monster go down." Tiamat shrugged and the other soon joined in as well, eagering to tame the wild dragon with their own flesh.

To many men, it was like the wildest wet dream possible but to Issei Lucifer, formerly Issei Hyoudou of the old timeline, it was simply another morning.

Line Break

Around midday, after finishing his works, Issei decided to take a trip to the human world with Grayfia. His parents, as well as his relatives, didn't exist in the new timeline, but Issei still came to the empty lot that used to be his house time to time to remind him about them, making sure that they would never be forgotten, at least by him. Grayfia would always find herself getting curious about the place every time she came there with her husband, but chose not to question her husband because she respected his privacy more than anyone and for that, he was very grateful.

After that, the two made their way to Kuoh Academy. It was Saturday, so there was no one at school at the moment. Looking at the old school building from the other side of the gate, Issei couldn't help but smile fondly at the memories. Before becoming a devil and Rias' servant, Issei thought there was nothing special about the school, other than the fact that it was originally an all-girls private school, a perfect place for pervert and horny teenager boys like him to enjoy the greatest times of their life. Soon, Issei realized that there was nothing but special about Kuoh, because the school had become the target for many evil forces around the supernatural world, Kokabiel and Khaos Bridage to name a few. Even the meeting between the leaders of three Great Factions from the Bible was also held there.

It's too bad that he would never be able to attend the place as a student ever again.

"Where are you going, Issei-sama?" Grayfia asked suspiciously while looking at him with half-lifted eyes, because she got a feeling that she knew where he was heading.

"I want to pay Shuri and her daughter a visit. Why? Is there anything wrong with that?" he smirked slyly and returned Grayfia's question with his own. The beautiful silver haired Queen looked at him for a moment before sighing in disappointment. She should have seen that coming from him, because after all, she spent the last fifty years trying to keep him from sneaking away, abandoning works to fuck some random women he found attractive enough to suck his glory cock.

"Oh no, no you don't Ise-sama." Grayfia raised her hand and stopped him "You're not going anywhere, not until you finish the rest of your works." She pointed out while giving him a stern glare "It's time to go back."

"You're no fun at all Grayfia." Issei pouted "How about this, I…"

"Do not try to bribe me, Ise-sama." Grayfia shook her head, hardening her glare "Sex with you is not that…" but before she could say anything more. Issei grabbed her around the waist and shot into a nearby alley before getting to work on his own clothes as well as Grayfia's clothes. In a blink of an eye, Grayfia realized she was pinned against the alley wall, maid-uniform loosened, bra removed and thrown to the ground, her huge tits on display, legs spread, and panties pushed down to her knees. Issei had one hand holding her wrists together above her head, his knees made sure she couldn't kick or knee him in the sin, keeping her firm against the wall. As much as Grayfia didn't want to admit it, Issei could easily overpower her and stop her from beating him up like usual, it was just a matter of want or didn't want to do it.

"Ise-sama…" Grayfia gasped when her husband/master raised his hand and smashed her tits, hard.

"Excuse me?" Issei asked with a sly smirk "But were you trying to say sex with me wasn't that good?" he lowered his hand to his pants and unzipped the zipper of his pants, making Grayfia's eyes widen in realization.

"I-Ise-sama… we can't… not here, we're in public." Grayfia said nervous "What if someone sees us?" but it was too late, his cock was out of his pants. Issei grinned and stroked his dick as fast as he could, forcing it to get hard as fast as possible while keeping his eyes on Grayfia's erotic body.

"Don't worry, no one will see us." Issei grinned "But they might hear us, so better keep your voice down, okay?" He asked sweetly, making Grayfia smile forcefully and try to free herself by struggling "Oh no, you don't Grayfia, you're not going anywhere, not until I'm done reminding you how great sex with me is?"

"I-Ise-sama… I was just kidding." Grayfia tried to talk him out of it while Issei was rubbing his massive cock-head against her rapidly moistening pussy lips "I was just trying to convince you to…"

"Too late love." Issei gritted his teeth and grabbed her waist, making a wide smirk and spearing his dick into her pussy, forcing the bulbous tip of his cock into her womb in one single thrust "Better hold on tight Grayfia, because I'm going to take you to a wild trip." Pulling out half way, Issei then delivered a sharp fast thrust back into his beautiful wife's tight little pussy, developing a rhythm of fast, hard thrusts that forced Grayfia to cover her mouth to stop herself from loudly crying out in pleasure, while her arms came up to wrap tightly around his upper torso and her legs wrapped around his thigh, her chin rested on his shoulder.

Line Break

Ding dong!

After he settled things down with Grayfia and sent her home, Issei headed to Shuri's house, which located right next to the shrine Akeno used to live in in the old timeline, and pressed the doorbell as soon as he was there, as he could hardly wait to play the dominating game with the sadistic woman.

However, the one who answered the door wasn't Shuri, but a beautiful young woman with a voluptuous figure around the same age as Rias, her face greatly resembled his [Pawn], with very long black hair and violet eyes. Her hair was tied in a long ponytail, reaching all the way down to her legs with two strands sticking out from the top and sloping backwards, with an orange ribbon keeping it in place. Like the first one, she wore the customary Kuoh Academy school uniform for girl, along with black knee-high socks. She was none other than Akeno Himejima, Shuri's daughter with Baraqiel and his sister's Queen.

And from the small apron she was wearing around her waist, he could tell that Akeno was working in the kitchen before leaving to answer the door.

"Ara, Lucifer-sama." Akeno gasped in surprise and bowed her head at him, her hands put together on her lap "Welcome, to what do I owe this honor?"

"I'm here for your mother, Akeno." Issei smiled before tiptoeing over to look into the house, searching for another black haired Himejima "Is she at home?"

"Well, my mother went to buy groceries at a nearby shopping mall." Akeno told him "So it's up to me to… keep you company if you decide to wait." She said, smiling seductively. Her words made Issei to look at her giant breasts, which were probably one of the the biggest pairs of tits around, and it didn't go unnoticed by Akeno.

Akeno, meanwhile, had become even more obsessed with Issei after he rescued her and her mother. Much like Rias, for the past few years Akeno had been staring at him with nothing but lust in her eyes, acting like a horny high-school girl whenever he was around or came to her house to 'visit' Shuri. In the old timeline, despite being seductive and quite flirtatious toward him and acting like a mature young woman, Akeno was still innocent and emotional towards love; however, in the new timeline, with her mother around to guide and teach her, plus Issei's constant visit to their house, Akeno had become quite mature and bold in said aspect.

Ophis had stated very clearly that even though she resetted the timeline, she decided to keep Rias and the girls' feeling for him intact, because it would be very difficult for them to fall in love with him again without him there for them like the last time. Maybe he could manage to pull it off one way or another, but Ophis believed it would be better that way.

Of course, she wasn't unfamiliar with the story of Issei Lucifer and his unrivalled sexual prowess, Akeno being the first low-class devil who knew about it from her mother. Hell, he could even feel her eyes on his back whenever he decided to have his way with Shuri in her house.

"Great." Akeno stepped out of the way and let Issei to walk into her house "So… exactly what do you need my mother for, Lucifer-sama?" She didn't need to hear it from him to know the answer, because there was only one reason for him to be there, at her house.

"Well, I need your mother to do some improper things to me, Akeno, as well as the other way around." He said, acting like he was serious.

"Ara ara, are you sure it's legal for you, a Maou, to do that, Lucifer-sama?" Akeno gasped in surprise and shock, but like him, she was acting "Having improper relationship with someone not your wife?" He knew that Grayfia was Akeno's idol, because she was a big fan to their love-story, just like the original timeline.

"Don't worry, nothing I can't handle." He turned around and smiled at her "Also, call me Issei, you don't have to address me so respectfully like that when we're alone. After all, we're all family, aren't we?" he walked into the living room and took his seat on the longue.

"Yes we're, Issei-sama, yes we're." Akeno smiled before continuing "Please wait here, Issei-sama. I will make you some tea" Issei nodded his head in approval, allowing Akeno to head back into the kitchen to make tea for him. However, because he was facing away, he couldn't see the smirk on Akeno's face when she turned around and walked away 'Sorry Rias,' She thought, her hands reaching for the buttons of her shirt 'But it seems… I'm the lucky one.'

Issei didn't have to wait long, though "Here is your tea, Issei-sama."

"Thank you Ake… woah!" Issei made a sound in amazement when he saw his sister's Queen, standing before him wearing absolutely nothing but the pink apron, which ended just below her pussy and left a lot of cleavage, the sides of her breasts, as well as her entire behind completely exposed. The sight of her voluptuous body, hiding behind nothing but a small apron like that, made him want nothing more than bending her over and fucking her as hard as he could "Girl, you sure know how to please your superior, just like your slutty mother?"

"Ufufu, I'm glad that you like it, Issei-sama." Akeno giggled and bended over, with her hands on his knees to kiss him on the lips when Issei made a 'come here' gesture with his index finger. Issei sat there and parted his lips slightly, allowing Akeno to insert her tongue into his mouth. They made out for a full minute before Akeno pulled back, thin a thin trail of saliva connecting the tip of their tongue together.

"Quite a talented mouth you have there, my dear." As he spoke his hand cupped her breast, squeezing it delightfully, twisting her nipples between his fingers through the thin material of her apron, making Akeno become hornier than ever "How about you put it into good use while I enjoy your delicious tea?" Issei released her breast and leaned back against the backrest, holding a cup of tea in his hand.

"With pleasure, Issei-sama." Kneeling down between his legs, Akeno swiftly had his bottom half naked, before staring in awe at the man meat in front of her. She watched her mother getting fucked by her master multi times before, but it was the first time Akeno was able to see it so close like that, and realized his cock was a lot bigger than she thought, and he was still soft. Akeno then wrapped on hand around the base, but her hand couldn't come close to encircling it. She started to slowly jerk him with both hands, feeling it swell until she could barely wrap two hands around him. She gaped in bewilderment; it must be over fifteen inches long and extremely thick as well.

As she paused to admire it, she felt Issei's hand on her head, pushing her towards his pole while he was still enjoying Akeno's delicious handmade tea. The black haired Queen eagerly leaned towards him, sucking on the tip as it pushed into her mouth. She drooled at the taste and realized that she could suck his cock all day! She quickly sucked his whole head inside her mouth while pumping the rest of the cock with her hands, drawing a moan from the powerful super devil. She swirled her tongue around his head, licking up the pre-cum spilling from his tip, eagerly using her hands to serve Issei's large balls.

"Surely you can do better than that, Akeno dear." Akeno gasped and had to fight back the urge to gag when Issei, using his grip on her head, forcefully forced his dick down her throat, finding her lips locked nearly at the base, and his head poking her stomach. Sighing in pleasure, Issei kept her head like that for a moment and slowly poured the hot tea down her naked back. It wasn't hot enough to burn her, but it hurt her enough to bring out her masochism nature. As the hot liquid running down her curvy back to her ass crack, Akeno arched her back and moaned out lustfully, causing her throat to vibrate around his cock. Issei then started to fuck her face onto his cock and she responded eagerly, sucking as hard and licking as much of his cock as she could.

His heavy balls, which, like his big cock, were covered in saliva from her stuffed mouth, clenched and she felt her treat empty into her throat. His first shot filled her mouth completely, some flowing straight to her stomach. She swallowed his thick delicious cum as quickly as she could, trying to get it all. Despite her best efforts, some spilled out of her mouth and fell onto the top of her tits and the chest area of her apron.

"Like mother, like daughter I guess" Issei chuckled as he finished the last of his tea while watching Akeno doing the same to her first ever treat of his sperm. As Issei finally stopped cumming, his grip on Akeno loosened, allowing her to back of his still hard cock.

"Did I do well, Issei-sama?" Akeno asked, planting a wet and loving kiss on the tip of his cock

"You did well, Akeno" The Maou grinned then stood up, removed his shirt, and Akeno found herself drooling at his impressive abdominal muscles which looked like stones stacked up to his chest "But it's time for me to enjoy the main course." Akeno almost creamed herself at the thought of what about to come.

"Do whatever you want, Issei-sama."

Smirking slyly, Issei grabbed her at the back of her neck and roughly bent her over the table with his still hard cock kissing the entrance of her pussy. Then with a manly grunt he shoved in, thrusting twelve inches of his cock balls-deep without any gentleness, breaking her hymen before she knew it, and when his cockhead slammed into her womb she let out a deep, satisfied scream.

"Well, shouldn't expect anything less from the daughter of a slut, should I?" Issei grinned, taking a hold of her hip with both hands and started to fuck her with his cock, working the last few inches into her cunt before going wild with her tight, virgin pussy. He pulled out and slammed back in with long, hard thrusts, slamming his hip against her ass again and again and again, his rock-hard hips practically spanking her inner-thighs. Akeno was quickly cumming her brains out, and her hips bucked as waves of pleasure ripped through her body.

It didn't take her long to cream her inside with his sperm. For several long moments, Issei remained inside her, moaning into her ear as his orgasm waned, the shear amount of semen Issei Lucifer was pumping into her womb after the first few minutes caused her abdomen to expand as if she were already nine months pregnant.

Her cunt desperately clutched at his massive invading shaft, his final thrusts making her cum again and again and again. Then he stepped back and pulled his enormous cock out of her slowly, inch by inch until only the head of the fifteen inch shaft remained within her fertilized cunt. Finally he ripped the head from her pussy and stood aside. A torrent of pressurized jizz spurted from the black haired Queen's gaping cunt, splattering the opposite wall. Akeno moaned as she began to deflate, blasting cum all over the floor. Finally the torrent slowed down, Akeno fell and sat on the ground with her back lean against the table, breathing heavily, utterly spent.

"The fuck are Shuri doing?" Issei wondered while looking at the clock "Oh well." The brown haired boy shrugged and turned back to Akeno, who had regained her composure and smiled at Issei, who were staring at her breasts and thinking about the best way for him to enjoy the largest pair of tits around.

Little did he know that Shuri had returned long before Akeno started sucking his cock, but chose to leave quietly after realizing her daughter's intention and couldn't stopped herself from silently cheering for her daughter, imaging about a possible threesome between the three of them.