Please note that this fanfic is written based on when Rias has graduated high school (19 y/o) and married Issei (18 y/o).

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Issei couldn’t help but smile at the familiar sight of Kuoh Academy as he turned the corner. 

His latest mission of hunting and destroying a fallen angel for the Gremory family had taken longer than expected. The tricky bastard had proven to be quite the adept sneak and had managed to get away several times before his untimely demise. 

It’s been nearly two weeks now since Rias had sent him off on his latest task. His phone had been destroyed during the chase and Issei was looking forward to hearing his cute fiance’s voice again, even if she spent the first five minutes scowling as she berated him for carelessness. She was so cute when she was pouting, he didn’t mind her nagging him.

The school grounds were lively as students trailed in for the day. Issei’s eyes wandered happily among the female students, admiring how great they looked in their uniforms. A few girls with bouncy bosoms had their top buttons undone and he fully appreciated the ability to check out their cleavage before watching their swaying asses sashay away in their short magenta skirts. God, he loved the uniforms here. The button down corsets the girls wore only further accentuated their curvaceous figures. It was good to be back.

His thoughts drifted back to his fiery haired fiance. Known as the Crimson Haired Ruin Princess or the Princess of Destruction, Issei had never dared to imagine that their relationship would become what it is now. Then again, a lot had changed since she’d come into his life – literally reviving him into the demon he was today. He still remembered the first time he’d seen her, how her flawless beauty had taken his breath away. Still remembered how her words had been the last he’d heard upon dying, and the first to welcome him back as she revived him. He still couldn’t quite believe how incredibly lucky he was that she wanted to be with him.

He looked down to check that his own uniform was in order. Black blazer, check. White, long sleeved dress shirt, check and unbuttoned. Rebellious red t-shirt underneath, check. Black dress pants, check. Issei paused as he took in his worn blue and white sneakers. They were getting pretty scuffed and dirty from all his recent missions. There was no way he was ever going to bother with the school’s brown dress shoes, but maybe it was time to get himself a new pair of sneakers.

As the familiar building loomed ever larger with each step towards it, rather than entering the main school building and following the flow of bodies, Issei veered off to the side. Leaving behind the early morning chatter as students streamed into the building to find their classrooms, Issei admired the school grounds from a very different perspective as trees enveloped him. 

Kuoh Academy had always given him the impression of a grand mansion. Even for a private school, it was ridiculously grandiose. Though now that he knew the true purpose of the school and was a part of its inner workings, Issei had long stopped being surprised by the lengths the Gremory family would go to keep themselves comfortably accommodated.

The clock tower of the old schoolhouse poked up out of the treeline ahead. The quaint little three story building was charmingly picturesque, painted white with a dark grey slate roof and vibrant green vines creeping up its side to the second floor. Originally the schoolhouse years and years ago, the abandoned dormitory was now the fabulously renovated base for the Occult Research Club created by Rias. 

As he neared the building, memories of his most recent intimate moments with Rias at the clubhouse had his heart beating a little faster. He still wondered if he could’ve done it differently, said it better somehow when he’d confessed his feelings to her. He could still see her expression, her blue green eyes filled with joyful tears, when he’d addressed her as Rias for the first time as he told her he loved her.

Stepping out of the treeline, the clubhouse stood quietly before him and he took a moment to admire it. So many memorable events had occurred within those four walls…the first time Rias had let him rest his head on her lap, the first time she’d let him use her breasts as pillows, all the times he’d been distracted by her hourglass figure during their meetings…he was getting a bit hard just remembering. Maybe today…maybe…he gulped, wondering if today would be the day when he managed to finally work up his nerve and…

“Oh god,” he spoke aloud to himself, suddenly flustered as his imagination ran away. “C’mon Issei, get it together! She’s your fiance now. We haven’t seen each other in two weeks! I’m coming back with good news and today…today is the day that I’m finally, finally going to get in Rias Gremory’s delicious wet panties and take. Her. Virginity!” 

His rousing speech was met with birds chirping happily among the tree branches. He looked around, embarrassed, and was glad that no one seemed to have been around to witness his sad little pep talk to himself. Despite being engaged, the furthest Issei had gotten with Rias so far was a lot less exciting than what his jealous peers assumed. Despite his life goal of becoming a harem king (now with the addendum of also becoming a demon lord) he was still a virgin…though Rias’ habit of insisting on sleeping naked with him has tested his willpower on several occasions.

Stepping through the front door of the club house, Issei called out to no one in particular. “Anyone here? I’m ba~ack! Tadaima!” It was surprisingly quiet. Part of him felt a bit disappointed. The group could be a bit rowdy at times, sure. And yeah, they always seemed to intrude on his personal space at the most inopportune times. But it was nice to be a part of such a close-knit group of friends. Plus, after two weeks off on his own, he kind of missed their company. 

Even though Rias had already graduated, she was often still found visiting the clubhouse. Issei was certain that he’d find his fiance here, but on the off chance that she wasn’t…well, he could definitely use a hot bath. Eyeing the plush furniture, he decided he could also maybe have a nap. After days of camping in the wilderness, Issei felt a newfound appreciation for the luxuries of modern living. He let his fingers trace across the wood paneled walls, linger over the soft velvet of the Victorian style couches and chairs as he made his way upstairs. 

He decided to stop by the President’s office first. Asia was the current club president, but in truth, Rias still frequented the place often enough that Asia only held the title on paper. Seeing how quiet the house was, he wasn’t actually expecting to find anyone. So it was with surprise that he did find someone in the President’s office when he casually opened the door without knocking. 

“Rias, you in here? I’m ba~ack! Eh?” He stopped short in the doorway, startled by the sight of an unfamiliar person sitting behind the President’s desk. It was odd seeing a guy seated behind the desk. Based off his uniform, he was also a student at Kuoh Academy but Issei had never seen him before. He must be in a different class, though judging from his appearance he looked to be maybe around the same age as Issei, possibly younger. Different grade then?

“Oh! S-Sorry! I didn’t mean to just barge in like that,” Issei apologized with a sheepish smile. “I’m looking for Rias, have you seen her around?” He took that moment to quickly look around the room, confirming that Rias was nowhere to be seen. He felt a bit disappointed by Rias’ absence but turned his attention to the stranger. “So, you must be a new club member, right? I’m Issei Hyoudou, nice to meet you!”

Looking up at the unexpected intruder, unimpressed brown eyes scrutinized Issei from beneath styled black bangs. It seemed he’d been in the middle of reading a book before Issei interrupted. The office walls were lined with bookshelves, each one filled with mystical tomes and books of ancient magicks. Lacing his fingers together, the stranger propped his chin on his fingers as he gazed steadily up at Issei, a friendly smile slowly spread across his lips.

“Ah, Issei.” The familiarity of calling him by his first name was rude, but Issei didn’t mind. “Or rather, Hyoudou-senpai is what’s proper I suppose.” The words were spoken almost sarcastically, but his smile and expression were perfectly charming. It was hard to know how to react. Either way, it confirmed Issei’s guess that he was younger and in a different grade. “I’ve heard so much about you. I wondered when you’d be back.”

“Oh?” Issei couldn’t help but feel a bit pleased knowing that the girls must’ve been gossiping about him in his absence. Er…actually, wait…”Only good things, right?” He laughed nervously, thinking of all the embarrassing things that could’ve been shared without his consent.

“Haha, of course~! Everyone seems to really look up to you, Hyoudou-senpai. I even heard how before you were revived as a demon that your life’s goal was to become a harem king.”

“E-Eh? They told you so much?! Ehehe…” Issei chuckled awkwardly, both embarrassed and surprised. This kid must be one of Rias’ new chess pieces then? Why else would he know so much?

“Yes! You see, I’ve been very interested in you Hyoudou-senpai…” 

Something about this guy just didn’t sit quite right with Issei. It was the way he said Hyoudou-senpai. His tone was mocking, and it was clear he was looking down on him. Or maybe it was the fact that he was a pretty boy, a bishounen who was undoubtedly popular for his fair skin, good looks and charm. 

“Oh? I didn’t realize the rumors about me were getting that bad,” Issei joked with a wry laugh. As a part of the school’s notorious “Perverted Trio,” Issei’s reputation of being a degenerate freak was well-known among the entire school. 

“I’ve always been fascinated with the supernatural, so it’s no surprise that the Occult Research Club caught my attention.” Leaning back into the plush velvet armchair, he pushed his seat back and away from the desk a bit. “You all did a fairly good job at keeping your secrets and being discreet, but something alllways slips through the cracks eventually.”

“Huh?” Issei eyed him, confusion clear on his face. What was this guy on about? 

“You see, I applaud you, Hyoudou-senpai. Because we share the same ambition in life. To become a Harem King!”

Issei just stared incredulously at him for a moment. That was not what he had been expecting to hear. This guy was all over the place. 

“I too, have always dreamed of becoming a harem king! Because how could a man ever be satisfied with just one set of gorgeous tits? Just one tight pussy to fuck for your entire life!?”

Now Issei was staring because he couldn’t believe this bishounen was preaching from the same debauched bible he lived by. Could this be the beginning of a beautiful new friendship?

“I’ve always believed in the occult and now…” Steepling his hands, he smiled up at Issei from behind his laced fingers. “Now I know that there really are demons and angels. That there are ghosts and werewolves and vampires. That youkai are real!” There was an excited gleam to his eyes now; it was hard to decide whether it was fanatical or menacing.

He was losing Issei again. Issei’s brow lifted as he stared at this guy quizzically. “Yeah, so?”

“So?!” He let out a long, disappointed sigh as his shoulders drooped slightly. “Tsk, I’m disappointed in you Hyoudou-senpai, though I expected as much after what the girls have told me.” His styled bangs swished softly from side to side as he shook his head. “You’ve lived with Rias for how long now and you still haven’t plucked her cherry? And that…I found that to be unforgivable and lost all respect for you.”

When he next looked up at Issei, his dark eyes were steely and cold. All of his earlier warm mannerisms had been frozen over by a sneering mask of utter condescension. “Then I thought to myself…Well, if you weren’t going to take her, then I would. Because what kind of fool would I be to turn down the chance to fuck a devil? And not just any devil, but Lucifer’s sister?”

It took a moment for Issei’s mind to catch up with his ears. Confusion, incredulousness, uncertainty, then indignant anger. “What? What have you done to Rias? Where is she?” 

Stepping forwards, bristling with outrage, Issei closed the distance so that only the desk stood between them. “Which clan are you from? Is this a rating game challenge?” 

His left hand fisted and he could feel his anger transforming, pooling to gather around his hand. A glow slowly began emanating from his clenched fingers. His left arm flickered as the glow began creeping up towards his elbow, the hidden dragon form beneath trying to emerge. “If you hurt Rias, I swear…” Issei snarled threateningly as he raised his flickering, glowing arm menacingly.

It infuriated Issei that the stranger only smiled smugly up at him in response, though his hands raised in polite defeat when Issei got too close. Yet his eyes weren’t even looking at Issei. Instead, they were admiring his magically transforming arm with open curiosity and gleeful fascination. “My, my, that’s just incredible. Hearing about something really is different from seeing it in person for yourself.”

Issei stepped forwards, leaning over the desk so his glowing fist – now slowly changing to red-scaled, taloned claws – was just a few inches away from the little asshole’s face. “I swear I’ll fucking kill you if you’ve hurt Rias in any way.”

Issei gritted his teeth, his jaw clenching irritably when the brat didn’t even flinch. Instead, that cocky smirk of his never left his lips. “Hurt Rias? I would never do that.” He rolled his chair back even further. Issei assumed it was to put some more distance between them, but instead his eyes widened in shock when he saw the familiar locks of crimson red hair hidden behind the desk. 

“R-Rias…?!” Disbelief laced his voice as he stared at the redhead kneeling between the guy’s legs. Her head bobbed subtly up and down on his lap and Issei felt a sinking feeling in his gut as he instinctively knew what he didn’t want to believe. 

“I’m afraid Rias is quite preoccupied right now. Simply more reason you should put that away.” In referring to that, he waved dismissively at Issei’s left arm, now fully transformed to its true dragon form. 

“I’m quite proud to say that she thoroughly enjoys me. You wouldn’t want to upset her by killing me when she’s in the middle of deepthroating my cock, right?” His hand trailed down to rest atop Rias’ head, momentarily pushing her down and holding her in place. Issei could hear her gagging on his cock and pure white rage momentarily blinded him. 

“Mm, I just love the way she chokes on me, the way her throat feels…how it clenches while she tries to breathe.” He leaned back in the chair, letting his head loll back in pleasure as his eyes drifted momentarily closed in bliss. “It’s too bad you can’t see her face while she gags on me. The way her eyes try to roll back into her head while she’s drooling all over my cock…fuck, I can’t get enough of her, she’s such a fucking slut for me.” 

Issei’s nails dug into the palm of his hand so hard that it was bound to leave little indentations, his knuckles white with clenched fury. For his left hand he could only feel the sharp pain of his claws piercing through his scales. Issei’s whole body felt like it was trembling with rage, energy vibrating through him. “Let. Her. Go.” He spat the words out quietly through gritted teeth. 

“Let her go?” His hand eased away from the top of Rias’ head, allowed her to jerk up off of his cock to take in a gasping breath before coughing for air. It was then that Issei saw the full length of his cock for the first time. Standing erect, he was at least 8 inches in length. Thick and veiny, his raging boner was so girthy it was no wonder Rias couldn’t breathe around it. Issei couldn’t believe that the pretty bishounen was sporting such a package – it felt like he was witnessing a strange conundrum. 

He raised his hands up in a helpless shrug. “I’ve never forced her to do anything.” As if to prove his point, upon catching her breath, Rias latched onto his slick member again, hungrily slurping it down her throat and occasionally gagging herself enthusiastically.

As more of Rias emerged from under the desk as she deepthroated him, Issei could see that she was completely naked. Ropes were tied tightly around her chest, making her already large breasts look even more outrageously enormous. Her arms were bound behind her back but she didn’t seem to mind. Kneeling before him, her flaming hair ran down her back, hanging to either side of her waist as her round ass wiggled eagerly in the air. 

“Just a week or two ago, she said she’d never sucked dick before. Now look at her. You love it, don’t you Rias? My little cock sucking whore.”

Rias didn’t even pause to respond. Instead, she attempted to talk around his thick member as she licked and slurped at it. “I, slurp, I love it, schlick, love your cock, mmfph, lurb yur cock, gulp, sho much Mawster.” 

Pulling Rias up by her hair, she practically whined in protest, mouth suddenly empty of delicious cock. “Say that again Rias. I want senpai to hear it clearly.”

Panting, her eyes silently pleading to return to her task, Rias whined needily. “I love your cock Master. I love your thick cock soo much Master Nawin. I love it so much. Please, please let me suck on it some more.”

It felt like all the air had been knocked out of Issei’s lungs. He stumbled back a step as if he’d been physically punched in the gut. His world was suddenly narrowing. The edges of his vision seemed to be going dark, then white, fading. A low ringing started in his ears, slowly increasing in volume as his tunnel vision slowly contracted down to a pinprick. He was so overcome with white hot rage battling with utter disbelief and hurt, his mind simply went blank. It felt hot, then cold, each extreme stung more than the other before he reached shocked numbness. 

Fingers fisting into Rias’ silky red locks, Nawin chuckled as he forcibly maneuvered her. Tugging her up by the roots of her hair before promptly pushing her back down till her nose was nestled against his trimmed patch. “There you go my little slut. All the cock you could possibly hope for.” His hips would buck up briefly whenever he pushed her down to the hilt, holding her head in place until she gave a choked gurgle.

“From what I’ve heard about you, senpai, it seems like you’re not equipped to be able to please a woman like Rias.” Pulling Rias up and off of him, he pulled her hair further back so that she had to crane her neck backwards as he forced her to look up at him. She panted breathlessly, eyes staring unfocused at Nawin as she smiled adoringly despite the spittle and pre-cum covering the bottom half of her face. “Isn’t that right Rias?”

“I thought all dicks were like Issei’s until I saw yours Master. It’s so much bigger and thicker, I thought you’d break me.” Rias pressed herself against Nawin needily, not even minding the tight grip he had on her hair. She wriggled her restrained body against him, mashing her giant tits against Nawin’s thick cock, desperate to somehow keep contact with him always. “I didn’t think you’d fit in me, but now I know better. I need your dick stretching my holes. Please Master, please fuck me and my slutty holes. I need it so badly. Please. I just want to be your cum bucket.” 

“Oh?” Nawin’s cock throbbed, twitching between Rias’ breasts as he looked down on her. “You know I can’t say no to you when you beg me like that. You’re such a desperate cock hungry whore, Rias. Always begging to be filled. What am I going to do with you?” Leaning down, he pulled her up towards him. Gathering her in his arms so that she was kneeling up to meet him, their tongues met in a hot tangle as Nawin kissed her deeply. Rias returned the affection eagerly, hungrily, moaning softly into Nawin’s mouth as his hand roughly kneaded one of her breasts.

Issei heard everything as if from a distance. Their voices all sounded strangely distorted to him, yet he understood each word with perfect clarity. He saw the entire scene unfolding before him, playing before him…without truly seeing it. Watching it blindly, trying unsuccessfully to erase it from his memory as soon as his eyes witnessed it. 

Nawin bit and pulled at Rias’ bottom lip before breaking their kiss. “Get on my lap,” he growled huskily at her before loosening his grip on her hair. 

Rias didn’t need to be told twice. “Yes Master!” She eagerly got up and turned before lowering herself gingerly onto Nawin’s lap. Meanwhile, Nawin had slid his chair further back. He adjusted himself so that the tip of his leaking cock was pressed against Rias’ slick folds. She impatiently rubbed her wet pussy against him, letting out a small gasping moan as she eased herself back onto his stiff rod. 

Issei felt himself slowly shuffling backwards, trying to get away from the appalling scene. He no longer felt in control of his body. Everything felt distant, his body felt numb and robotic. Faintly, he realized that his left arm had lost the power he’d gathered and hung limply at his side, once again fully human. The back of his knee collided with something and he fell back to find himself slumped on the couch in front of the President’s desk.

As Rias fully impaled herself on Nawin’s thick cock, Nawin chuckled darkly when he noticed Issei slouched lifelessly in front of them. “So what do you think, senpai?” Rias was now fucking Nawin in earnest as she eased herself back and forth on his thick cock, squatting and bouncing on his lap while mewling breathy moans. She seemed totally unaware of Issei, lost in her own world of pleasure as she greedily fucked Nawin. Issei could hear how wet she was even from where he sat.

Nawin reached around, pulling Rias to lean back against him while he held her so that her feet rested on the edges of the seat as she continued writhing atop him. “Are you enjoying the show, senpai~?” Held in this way, with her legs spread wide open while Nawin continued to buck up into her, Issei had a perfect view of Rias’ pussy being violated. 

“Look how wet she gets for me. She just can’t help herself even though I tell her it’s rude to drip everywhere.” Issei could vividly see how wet Rias was, how it glistened damply against her skin, coating her inner thighs. 

He could see how her cunt was swollen a puffy pink, how easily Nawin’s cock slid into it. “Nnf, fuck.” Nawin breathed hotly into Rias’ ear as he bounced her on him. “Doesn’t her pussy look great, senpai? You should’ve seen it before I wrecked it. She was so fucking tight, even your little dick might’ve had trouble.” As Nawin’s hips bucked up, Issei could see how Rias’ pussy and asshole clenched in time with her punctuated cries of ecstasy. 

“But she’s still a tight fuck. She just needs a reminder now and then. Isn’t that right, Rias?” With that, he suddenly slapped Rias’ clit. 

The reaction was immediate, causing her entire body to jerk as if shocked by a jolt of electricity. “Ooh god!” she cried as she arched against Nawin. “I’m cumming!” She squirted with a strangled gasp as she came and Issei watched mutely as her pussy convulsed around Nawin’s thick rod. 

Nawin let Rias’ legs drop as she panted weakly against him. “Did I say you could cum?” There was a dark glimmer in his eyes. Pushing her up, he stood as well and leaned her over the desk. Rias’ bound tits pressed against the open pages of the book as Nawin slammed into her quivering cunt from behind. 

Gripping Rias by a handful of hair again, he yanked back mercilessly. The motion had Rias’s head craning back sharply while still being pressed into the desk. Tears pricked at her eyes from the painful sensation of her hair trying to rip out of her scalp. With each powerful thrust, Nawin’s motions were essentially crushing her clit against the edge of the desk. Each time, Rias’ cunt would tighten and squeeze as she let out a little shrieked cry. It didn’t take long before her juices were dripping onto the carpet. 

“Did. I. Say. You. Could. Cum?” Each growled word was punctuated by his hips slapping against her ass as he fucked her. But he promptly pulled out at the end of his question, leaving Rias slumped against the desk.

“No, Master Nawin,” Rias babbled tearfully, “I’m sorry Master, I didn’t mean to cum.” She wiggled her ass plaintively, begging for attention. “I’m sorry Master, I won’t do it again. Please, put your dick back in me. I need it.”

“Ah, Rias,” Nawin shook his head disapprovingly. “My poor, desperate slut.” Pulling Rias up by her hair, he led her around the desk towards Issei. Rias stumbled a bit, her legs still quivering from Nawin’s thorough use of her, but soon found herself standing before Issei. “Why don’t we show senpai what a good cum bucket you are, hmm?”

“Yes Master.” Rias seemed happy to have another chance to prove herself worthy of earning Nawin’s attention. She clambered onto the couch so that she was straddling Issei’s lap. Rias’ naked breasts seemed to finally snap Issei out of his stunned state.

“R-Rias, what are you-” Issei stammered uncertainly as Rias situated herself on his lap. His hands raised helplessly before falling uselessly to his sides again.

Grinding her wet slit against Issei’s crotch, Rias’ hips squirmed down against him. “Ooh~? Ufufu, are you hard because you love my breasts that much Issei?” As she rubbed her slick lips against his pants, staining his uniform with her nectar, Issei was startled then ashamed when he realized that he was hard beneath her. 

“Don’t worry Issei,” Rias purred sultrily. “I’ll make your little dick feel good too while Master Nawin fucks my ass.” The way she said it so happily, so eagerly…it made Issei’s stomach churn. He’d been so focused on Rias that he hadn’t noticed Nawin had situated himself behind her and was rubbing the tip of his cock up and down between her ass cheeks. Rias leaned forward to give Nawin a better view of her eager ass and dripping cunt, pressing her tits against Issei’s face. Issei didn’t have to see to know when Nawin entered Rias. Her enthused cries painted a clear picture. 

“Oooh, fffuuuuuuuck, yes, Master. Your cock, oh god, it’s so fucking big…ohgod, yes, put it in me, I love how fucking thick it is…ohfuuuckit’sinmee.”

Blinded beneath Rias’ breasts, Issei found himself experiencing things strangely intensely simply through touch. His hands clenched and unclenched repeatedly at his sides before they began wandering along Rias’ body – hesitantly at first, but soon losing himself to being enveloped by Rias. He could feel the heat of Rias’ sopping wet cunt even through the fabric of his pants, rubbing against his straining erection. He could feel how Nawin was pressing into Rias through the way her body leaned against him. 

Slowly at first, causing Rias to utter a string of panted nonsense as she babbled about how Nawin’s thick cock was stretching her ass. But soon her entire body was being thrusted onto Issei as Nawin began fucking her in earnest. Rias’ screams rose and fell, her words frenzied and nonsensical while constantly pleading for more, more, ohfuck Master please, please FUCK MY DIRTY HOLE!! Rias’ slick slit was dripping, she was so needy she’d drenched Issei’s pants.

Meanwhile, Rias and Nawin seemed to have completely forgotten about Issei – he was simply a part of the furniture they were fucking on. Nawin’s hands were gripping either side of Rias’ hips, fingers digging in as he pounded into her tight ass. He could feel his orgasm building, brewing in his balls, churning at the base of his shaft. 

Nawin smirked as he caught sight of Issei’s tentative wandering hands. This only seemed to motivate Nawin to use Rias even more roughly. The palm of his hand landed against her ass repeatedly with a resounding smack as he spanked her. Each sharp spank had her holes convulsing and Nawin could feel how close he was getting.

Pulling Rias up by her hair, Nawin wound the waist length locks around her neck, effectively pulling her back while choking her at the same time. His other hand lowered to Rias’ clit which he began rubbing firmly as his hips continued thrusting into her and he grinned down at the glassy-eyed Issei as he felt how Rias was right on the edge. He wanted to make sure that Issei got a good look of his fiance cumming. 

Her body was tensing, becoming so taut that she felt like she’d break. But breaking her was exactly what Nawin wanted and he didn’t stop. Didn’t stop until he felt his own orgasm cresting. Just as he felt his cock pulsing, he grunted into Rias’ ear while pinching her clit hard. “Cum for me, you fucking slut.” 

And cum she did. Finally hearing the words to her release, Rias let out a choked, strangled scream as her body shook. Issei could see her holes clenching desperately, her ass milking Nawin’s cock while she squirted all over him. Nawin held her up against him for a bit, chuckling as he watched Issei’s blank, expressionless face before letting go and letting Rias fall weakly atop Issei. 

“I always wondered what the face of a broken man looked like.” Pulling his cock out, it didn’t take long before his cum was slowly dripping out of Rias’ gaping asshole and mixing with the mess she’d already made on Issei’s lap. Wiping his slick dick haphazardly against Rias’ pink ass cheeks, he tucked himself back into his pants with a chuckle.

“And now I know.” Walking back around the desk, he sat down heavily with a contented sigh. Within a few minutes, he had straightened the desk and was perusing the book again. The couple on the couch across from him completely ignored.

Meanwhile, still pinned beneath a quivering, panting Rias, it took a moment to realize that Rias’ mumbled stream of words were endless thanks to Master Nawin for letting her cum. Issei began feeling little tendrils of self-hatred curling in his chest as he realized that he’d cum in his pants while watching Rias spray him with her juices…