Chapter 5: The Crimson Sexpot.

"Hey, Asia."

"Oh! Hello, Issei!"

"Whatcha doin'?"

"I'm just trying to loosen up my butt with the plugs you gave me." Asia replied casually, no arousal coloring her tone. Ah, yes. He did tell her to do that, didn't he? Looking down at the box at the foot of her bed, Issei could see that there was at the very least fourteen different butt plugs inside, all varying in shapes and sizes.

"How many have you gone through, so far?"

"This is the last one!" Asia cheered proudly. Naked on her bed, with her cute bubble butt in the air, the ex-nun was easing the last toy into her asshole. This one was cone-shaped, made of glass, and colored a beautiful shade of maroon with ridges and bumps all over it.

"Need a hand?" Issei asked politely.

Asia shook her head, a determined look in her emerald eyes. "No, thank you. I made it this far on my own, so I'm not gonna ask for help now!" Her brow furrowed and her tongue stuck out from the side of her mouth as she focused on her task. It would've looked cute if the task at hand wasn't pushing a butt plug up her ass. It took a few more prods before her sphincter gave way and let the toy inside, the ring of muscle stretching out as the plug slowly sunk in.

"A-Al…most…in… T-There!" Asia let out a sigh of relief, the butt plug now successfully lodged inside.

"I did it!" Asia cheered, happy that her ass was able to swallow the biggest toy out the bunch. She giggled and gave a celebratory wiggle of her hips, her butt-cheeks jiggling slightly.

With a lecherous grin, Issei approached the edge of the bed. "That was really good, Asia!" Chuckling, the perverted young man grabbed the nob handle sticking out of her asshole and stirred the plug inside her ass around. Asia whimpered at the feeling, her stretched walls struggling with the sensation.

He then started tugging at the toy, trying to get it out. Asia gasped as her ass refused to let it go, the rectal muscles hugging tight and not letting up. It took a full minute of pulling and twisting before her asshole finally relented and loosened its grip on the toy. The ex-nun squealed a little as the large base of the tapered toy stretched her sphincter before slowly closing as the rest of it easily left her anus with a 'pop!'. Asia's pink ring doesn't close immediately like Kalawarner's or Esdeath's. Being human, the blonde's asshole isn't used to such abuse and stays wide open for a good few seconds.

Issei spread her cheeks and was quite surprised at her the condition of her anus. "Woah! Even after all those toys, your asshole's still got a pretty gape, Asia! You can really take a beating!"

Asia turned to face him before sitting back with her ass on her heels, putting her hands in her lap as she looked off to the side bashfully. "U-Um, thank you, Issei…" she muttered, blushing.

Issei handed the butt plug back to her. "Here. Use your mouth to clean it off."

"Oh, okay…" Asia nodded and proceeded clean it off with long strokes her tongue.

He gave her a pat on the head "Alright, I'm off to school!"

"Have fun, Issei!" Asia waved goodbye before putting the whole toy in her mouth. She needed to be thorough, after all!

…

Issei strolled the halls of Kuoh Academy, his brown eyes flicking over any fellow student that passed him by. Now that he was fully confident in the books abilities to grant his any desire, the young man decided it was time to take the next step forward on his way to becoming the Harem King. The next step being… Rias Gremory.

Issei was smitten with the redhead the moment he laid eyes on her…but let's be honest, who the hell wouldn't? Rias Gremory was, with out a doubt, one of the most beautiful women he had ever seen in his life! Her beauty was almost inhuman in how perfect it was, like her body was biologically designed to be as seductive as possible…

Most likely because it was.

Issei smirked to himself at that. A part of him always wondered if there was something more to the redhead. Looks like he was right after all.

He eventually moved his search to the school campus. Just when he was about to look elsewhere, he spotted her. Walking amongst the students, Rias Gremory's blood-red hair stuck out like a sore thumb as it bobbed with every graceful step she took.

Issei followed her, being sure to keep his distance as he watched students, boys and girls alike, marvel at her presence. Her long legs, the sway of her hips, and the bounce of her enormous bust definitely caught the eye of any and all that she passed by.

He watched as she walked off campus and onto a dirt path. Reaching into his coat pocket, Issei pulled out the book that made all his dreams come true. Smiling, he followed after her.

…

'Rias Gremory is engaged to marry Issei Hyoudou…and she is not averse to certain premarital activities...'

His pen tapped his lower lip thoughtfully. What to wright next? Issei wondered… He suddenly perked up, a particularly lewd idea coming to mind. Grinning, he next wrote down…

'Members of the ORC will not care if Issei Hyoudou fucks Rias Gremory in front of them.'

After a moment of further thought, Issei then added:

'In fact, the females of the ORC would be more than happy to join them if asked.'

He then put the book away, and entered the old school building where the club resided. Making his way to the club room, Issei opened the doors to find the only one inside was Rias. She sat at her desk on the other side of the room, right hand neatly placed over the left, smiling at him.

"Issei Hyoudou…I've been expecting you."

The young man rose a curious brow. "You have?"

Rias nodded. "Yes. I've been keeping an eye on you for quite some time now, and you have most assuredly caught my interest. It's also quite coincidental my family had picked you to be my indented husband." Her gaze turned half-lidded as she stood up from her chair. She walked around the desk, hips swaying as her hand trailed across its surface.

"What about me caught your eye?"

Her hips continued their sensual sway as she approached him. "You have power. I can feel it. It is most… Mm…potent." She ran her tongue slowly along her glossy bottom lip, moaning as she felt the level of aura he possessed. "Can I ask you a favor, Issei? May I see your Sacred Gear?"

Issei smirked. "Not at all." He was curious about these 'Sacred Gears' himself ever since he learned of them from Raynare. He closed his eyes and focused.

After a brief moment of concentration, Issei felt something awaked inside of him. Opening his eyes, he looked over his shoulder and found wings had formed on his back. But they weren't like the black feathered wings his Fallen Angels possessed. No, these were a white frame with glowing blue edges; it reminded him a lot of the Lancelot Knightmare Frame in Code Geass.

"I see. You possess Divine Dividing. A Longinus. To have such power at my side is most fortunate." Rias walked around Issei and reached up to touch the metallic white frame, gently running her hand along it. Issei mentally deactivated the Sacred Gear, the wings disappearing with a flash of blue.

"Now, then…" Two round orbs pressed into his back. "Would you care to demonstrate some of that power~?"

With a sly grin, Issei turned on the spot, the shear speed in the action causing the redhead to let out a gasp of surprise. Before she knew it, Rias was bent over her own desk, her skirt flipped up and her lacy black panties pulled down to her ankles. "Ohh, so forceful~." Rias moaned, looking over her shoulder at him and biting her lip with a wiggle of her well-rounded hips.

"Fuck, you've got a big ass!" Issei growled, raising both of his hands to give her cheeks a hard smack, the pale globs of flesh giving a satisfying jiggle as Rias moaned louder in response.

"Mm, I-Issei wait." Rias said, looking back at him again. Issei was annoyed at being told to wait, but obliged her request. "You need to know that my virginity must remain intact for our wedding. S-So until then…" she reached back, putting her hands on her ass and pulling it apart to expose her pristine asshole. "this is all I can offer."

Looking down at her anus, Issei smiled. "Fine by me; I was gonna fuck your ass, anyway."

Whatever her reply to that was gonna be, it was stopped upon hearing door open. Issei looked over his shoulder to see that it was the school mascot Koneko Toujou entering the club room, carrying with her a rather large bag of sweets. The white-haired loli stopped in her tracks when she caught sight of the scene in front of her.

She blinked. "President, is this the perv you're gonna marry?" she asked, her voice carrying little emotion.

Still pinned to the desk, Rias looked back at her only Rook the best she could from her position. "Now, now, Koneko, be nice. He'll be part of our family soon."

"Hn." Was her response before sitting down on the couch to her right. She was about eat her candy when Issei spoke up. "Koneko, can you come over here, please?" with an irritated grumble, the loli rose from her seat walked up to the pair.

"What?"

"We don't have any lube. Mind prepping Rias up for me?"

"…Fine." She said, still with that disinterested tone, as Issei moved back so Koneko could start. With her being so short, Koneko didn't have to lower her head that much to get between her King's spread ass cheeks.

"Oh…ohhhh. Oh my, Koneko~." A breathless giggle escaped the redhead's glossy lips as her Rook's pink tongue worked back and forth over her rear; licking across the tight little pucker and leaving it nice and wet.

Koneko let out an annoyed grunt then spat on the hole. She smeared the saliva around the tiny pink star with her tongue, being sure to give it a very thorough rimming so they wouldn't have to bother her again while she was eating her candy. Yep, totally not because she secretly loved making out with Rias' asshole and wanted to indulge in this guilty pleasure of hers for as long as she could.

Almost a minute later, she pulled back, a string of saliva connected her tongue to Rias' pucker briefly. "There. Can I go, now?" Please say 'no'!

"Nnnnnnot just yet." Issei grinned cheekily. "Stay kneeling."

Koneko barely managed to repress a shudder. She moved out the way and pressed her face up against Rias' left ass cheek, looked up at him with her dull stare, and opened her mouth. Issei slipped his cock into her waiting mouth, doing a few deep pumps inside her orifice to get his dick coated with saliva, before he grabbed his cock and readied it at the redhead's asshole. Issei slid in balls deep with one rapid motion.

Rias screamed as she felt his hot, veiny rod plow deep into her tight virgin ass. Then she felt him slowly, agonizingly pull out. Whimpering she pushed back, only for him to hold her in place. Then he slammed into her again, harder and deeper than before, the impact driving the breath from her lungs. Looking back shakily, the crimson-haired beauty saw Koneko watching her get sodomised with no shortage of shock and…awe? Yes, her Rook was staring on in wonder, amazed that her bowls could make so much room for such a long and thick cock.

Koneko looked up at her King, concern evident her gold orbs. Rias was able to give her a shaky smile, ushering her that she could take it. But that wasn't good enough for the little loli; she reached between her King's thicc thighs and touched her clit. Rias twitched and shuddered, appreciating Koneko's efforts to make the massive cock up her ass easier to take. Her eyes rolled back into her skull as Issei pulled out again, and began to pummel her thicc ass, alternating between slow and deep, and hard, yet fast hip thrusts.

Issei grunted, enjoying the hot, tight tunnel that was Rias Gremory's asshole. He felt it spasm around his cock, the hole trying to get accustomed to his girth as it stretched around him as he plunged in again, again, and again. "Mmm, fuck, your ass is snug as hell." He slapped her ass, making her rectum quiver.

"S-So big!" Rias moaned out, barely able to get out a coherent thought as her fiancée continued to scramble her insides with his relentless thrusts. He leaned forward and turned her head towards him. Issei connected their lips in a tight seal. Their tongues danced together as their bodies were repeatedly pulled together by Issei's grip.

It was all too much. Her muscles clenched when she felt her orgasm arrive. Rias pulled away from Issei's mouth to cry his name; it echoed in the walls of the ORC. Her ass grinded against his hips, begging for him to unleash his seed. Issei happily obliged, pushing himself as deep as he could to release a torrent of hot white cream that sent her insides burning. Rias let out a keening wail as she squirted pussy-juice all over Koneko's hand, the nectar soaking into her uniform's sleeve.

Issei pulled out of his own redheaded cock-sleeve, his thick spunk spilling thickly out of her stretched ass and onto the ground as she went limp. Before Koneko could even comprehend just what she even witnessed, Issei grabbed her by the back of the head and shoved her face into Rias' ass again. "Eat out all that cum."

Koneko obediently did as ordered. Sucking greedily, the loli stuck her tongue inside Rias' asshole, able to work it all around the stretched-out cavity. She could probably fit her whole fist inside, easily. Koneko moaned at the taste, the cum tasting better than any candy.

Eventually, Issei pulled her back, her face sweaty and her mouth covered in his semen. "Liked it?" he asked, like she was trying out some of his homemade cooking.

Panting, the white-haired Rook replied. "Y-You…are so fucking…depraved."

"And you love it."

She whimpered; he was right.

AN: I hope everyone enjoyed their Valentine's Day! Unlike me, who just spent it alone, at home…finishing this…

…

See ya!