Issei's Affair with the Gremory's
{Commissioned by anonymous}
Rias Gremory has always had a massive crush on Issei. But, behind her back, it seems that his affections were targeted towards someone else, who just happened to be familiarly close with her. Read as Issei indulges in his fantasies of her sister in-law, Grayfia, and possibly many more…
The Taste of GrayfiaTags - NTR, Harem, Alternate Universe
Notes - This story takes place in a modern setting. All characters are the age of 18 or above.
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Issei and Rias Gremory had been best friends since they could remember. They were now in their final year together at High School, and happened to rise on the hierarchy of "popular students", originally without their knowledge. They'd always garnered attention wherever they went, whether that be through compliments that fellow students were too shy to confess to, or sometimes gossip about their relationship together. It seemed that many had taken an interest with the two, and it was definitely something that was difficult to ignore.
The fact of the matter is, some were at least half right in their speculation about their relationship. The longtime friends weren't exactly dating or anything like that, but Rias Gremory had a massive crush on Issei. While he couldn't deny how sexy she was, definitely feeling physically attracted to the crimson haired babe, his feelings of affection were actually reserved for Rias's older sister in-law, Grayfia. The matured woman lived with her and Rias's mother, Venelena, after her husband moved away for work.
Another thing that factor into their closeness were the proximity of their abundant households, happening to be situated right beside each other as they were childhood neighbours. One day, after taking a much needed nap, Issei was wiping his eyes as he stretched out on his bed. Wanting to let some light into the darkness of his room, he opened the blindfolds where the bright light from the sun shone through, blinding him for a brief moment. Sometimes, he could see Rias hanging around her large backyard, and they'd occasionally wave at each other if that was the case. He squinted to
focus his still awaking eyes as he noticed someone in the backyard, discerning who and what she was doing until his vision finally cleared. "Oh!... It's Grayfia.." he thought to himself, with his eyes widening as he noticed her extremely revealing white two-piece bikini. The separate top and bottom pieces were connected with what appeared to be metallic-like rings, and it did a terrible job at covering her perfect clear skin.
At first, his erection was a matter of waking up, but after being treated to this delectable sight, let's just say his "morning wood" was caused by something entirely different. He couldn't deny that he was infatuated with the older woman, at times finding himself fantasizing about sleeping with her. Today was no different, as he cursed himself for being so perverted as he began to fiddle with his pants. "Oh well, here we go again!.." he thought to himself as he excitedly pulled down his undergarments, his large cock springing out into the openness of his private bedroom. It was definitely wrong to peep on his best friend's sister in-law, but she was so undeniably sexy that it was
nearly impossible for him not to think about doing it.
Issei started to slowly stroke his penis, allowing it to grow into full mass as he concentrated on her attractive figure. Grayfia, just like Rias, was incredibly voluptuous. In possession of a figure that made men weak to their knees. He wasn't subject to these effects, as he groaned while masturbating to
the sight of this busty babe tanning. In his own little fantasy, his eyes were closed in ecstasy as he imagined all of the dirty things he would do to her body. Groping those absurdly large tits, cupping a handful of her plump buttcheeks, jamming his cock down that cute mouth. There just wasn't a part of her body that he didn't want to see in all of its glory. In the midst of his heated jerk-off session, he failed to realize Grayfia momentarily catching a glimpse of him. It was obvious what he was doing on the basis of his face being scrunched in pleasure, which caused a sly grin to form on the older woman's face.
By the time his eyes were opened as he was about to reach a powerful ejaculation, Grayfia had already turned away, going about her day and pretending that she didn't notice that he was currently beating off to her. In an almost teasing manner, she applied oil on herself that made her skin glistening and rendered her bathing suit nearly see-through, only accentuating her womanly figure that made even more blood rush straight to Issei's throbbing erection. "Holy shit!..." he thought as his strokes reached a fever pitch, accidentally blowing his load from the incredibly sexy sight and shooting his semen straight up into the air, accidentally making a mess of the floor and some of his surroundings. "God damnit!... But, man… That was so worth it…" he thought to himself, while being conflicted that he just made a huge mess that he'd have to clean. Grayfia tried to look with her peripheral vision so as to not get caught, and giggled to herself when she noticed the satisfied expression on the man's face.
This torturous cycle continued to go on for who knows how long. At this point, Issei was beginning to grow suspicious from these convenient coincidences. One day, on his walk back home to school, he noticed Grayfia from her behind, who was bending over as she picked up her purse from off the floor. Obviously, he viewed this incident as a mere coincidence, and thanked the heaven's for the opportunity to openly stare at her round ass. But, she seemed to maintain the position for much longer than normal, but this wasn't enough to pique his attention just yet.
The following day, he decided to walk outside after his typical evening nap, and ended up running into Grayfia, as the two shared a brief conversation. Issei was definitely popular with women, but he couldn't seem to control himself around the woman he's had his eyes on. While normally confident and assertive, he found himself rather flustered by her presence, and also because he'd frequently recall the numerous times he'd beaten his meat while fantasizing about her. The outfit she chose to wear today was definitely risque, a crop top that showed off her slender yet busty figure, with her cleavage popping out for everyone in the neighbourhood to see.
"I must thank you for always taking care of Rias.. It makes me happy that you two are always so close with each other.." she thanked him while bowing down, showing her genuine respect for him
while accidentally giving him an eyeful of her cleavage. He had to gulp to clear his throat before managing to croak out his response. "U-Uh, yeah.. No problem!.." he said while openly staring at the crevice of her breasts, having to shake his head to break himself out of this erotic trance.
"Then… I'll see you sometime later.." she said, suddenly giving him a hug, her large breasts mashing onto his chest, leaving the stunned man speechless. Grayfia had a beaming smile on her face as she turned around, walking with a sway to her hips, as his eyes were mesmerized by her large ass swinging back and forth. "Is she?... Is she hitting on me?..." he thought to himself with a slight blush to his face, wondering if she'd been getting rather "friendlier' with him than usual. His imagination
ran wild as his heads were in the clouds, pondering on what he was planning to do if the vague hints he were receiving actually turned out to be real.
One day…
Issei was immensely bored, and felt the urge to drop in for a surprise visit to see Rias. Oh, and of course Grayfia too. As he'd always secretly frequented her place with that thought lingering in the back of his mind. Either way, their neighbourhood was relatively safe, and the door to her house was almost always unlocked. Issei welcomed himself in as he briefly called out to Rias, something he's done on numerous occasions. Except, the house had been eerily silent. Perhaps nobody was home?.. He thought to himself as he searched around the living room. It wasn't until he got near the living room that faint noises could be heard, as he honed in on his senses to figure out what these sounds were. His cheeks steamed red when the noise was apparent enough to be related to that of a woman moaning. "Was someone having sex?.. Not only that, but it sounds like Grayfia's
voice too…" he thought to himself, as he glanced back at the entrance and noticed that there weren't any men's shoes to be seen. His curiosity piqued, as his blood began to pump towards his member, he slowly crept towards the room and listened in.
The couch was facing the other way, so he was protected for now, unless she randomly turned around. Issei held his breath as he tried desperately not to get caught, pupils dilating as he focused intently on the immensely lewd sight. The woman of his dreams was sitting just a few feet away from him, quite obviously masturbating as he could almost hear the wet noises emanating from her
pussy. "Wow!... The sounds of her moans are soo… hot!.." he thought as her sexy moans rung throughout his ears, making him wish that he was the reason she was being this loud. Again, his imagination ran loose as he unbuttoned his trousers, his cock slipping free as he immediately started stroking himself to the tune of her voice. "Grayfia… Grayfia!..." he muttered under his breath as he began to furiously jerk off, not even worried that he might be overheard.
Aroused wasn't simply enough to describe the state of exhilaration he was in, the pacing of his breath growing ragged. He was so turned on that he didn't even think about the issues of morality his pervertedness came with, his sole focus was on bringing himself to a much needed release. There was so much sexual tension between the two that his libido had accumulated significantly over the course of the past few days, and overhearing her masturbate and even getting a glimpse of her in the
act was obviously too much for him to handle.
"Oh!.. Mmnn!... N-aruto…" she moaned lightly as the latter end of her words were drowned out, almost incoherent due to the softness of her voice. Issei's ears almost perked up when he briefly caught her whisper, uncertain if his hearing was playing tricks on him. "D-Did she just say my name?... No.. There's no way things can be flowing this conveniently for me!.." he thought to himself, being a victim of a once thought unrequitable love, sometimes viewing the older babe as a woman he would never be able to catch. The noises of her fingering grew loud and louder by each passing second, with Issei being unaware of what was causing her gradually rising arousal.
He didn't seem to catch up on it, but Grayfia had noticed the opened door the moment he walked in. After hearing his voice, she decided that proceeding with things as they were would be fine, planning to perform the ultimate tease for the young man. Though, she never expected him to stay, nonetheless start masturbating with her. The erotica of the entire situation spurred her on, making her even more turned on than she already was.
In disbelief, he tried to inch a little bit closer, perhaps preparing himself for a confrontation, but struggling to gather the guts to do so. Hesitantly, he tried to approach her, but his voice failed to creak out when he suddenly noticed those cool, pale eyes staring back at him.
Issei was too afraid to utter a single word, unable to come up with a single excuse that could pave an escape route out for him. There was really nothing he could say. Oh, sorry I didn't mean to walk in on you?.. Ah, that's right.. My raging hard erection is still whipped out because I forgot to tuck it back in my pants.. I totally wasn't doing anything suspicious or anything like that..
His face was pale in fear, thinking about this could potentially affect his relationship with both Grayfia and his best friend, Rias. He nearly jumped back when Grayfia suddenly stopped her motions, and stood up from the couch, revealing the loose clothing of her top and her completely naked bottoms, her panties hanging loosely around her ankles. "G-Grayfia.. I-... I!..." he stuttered as he failed to respond, standing in place as the woman approached him, with an expression that was difficult to analyze."Issei… Why don't you take a seat?.." she said softspokenly, to which the blonde man took a few seconds to register what she was saying. He was expecting more of an angered reaction, but instead he listened to her instructions, unsure of what to expect.
The nervous young man sat down on the couch, just sitting inches away from the same spot where Grayfia was masturbating a few seconds prior. "Calm down, Issei.. Don't be so uptight about everything.. Don't worry, I'm not mad.." she whispered hotly into his ear, sending tingles down his spine. "She's not mad?.Then, maybe she really was doing that.. While thinking of me.." he thought,
connecting all of the dots in his head. Grayfia's slender fingers suddenly rested atop his thigh, and squeezed it lightly as she stared directly into his eyes. This entire encounter felt surreal to Issei, similar to how someone who's experiencing something they've dreamed about for the first time ever.
Their eye contact was broken when Grayfia's eyes suddenly trailed down towards his legs, intently focusing on the mass object that caught her attention. Issei quickly realized what exactly she was
staring at, nervously gulping down what felt like a lump in his throat. "You've been a really bad boy, haven't you?.. Taking this big thing out of your pants and sneaking up on me.." she said in a seductive voice. Her fingers circled around Issei's thick shaft and grip it tightly, almost to insinuate that she was claiming it as hers before wiggling it teasingly from side to side. "Holy shit!... She's touching my dick!..." he thought in disbelief, her cool fingers a bit ticklish on his sensitive member. He was already aching and throbbing from his earlier ministrations, but having the woman of his dreams clutching him in an intimate manner made his heart rate shoot through the roof.
"Do you like that?..." she asked, almost a rhetorical question at this point. It was evident that she'd gotten the hint that he was immensely attracted to her, and was having some fun with him. "Let me thank you.. For lusting after an older woman like me.." she said, taking his breath away when she slowly descended her face level with his crotch. Her lips briefly touched the bulbous head as she teasingly muttered her words. "I've always thought that you and Rias were dating.. But, I didn't
know that you'd take such a liking towards me.." she said, planting a wet kiss on the underside of the head, swiping her tongue in a circle around him. "Unngh!..." he uttered, finding troubles constructing sentences while being subjected to such immense pleasure. He was never this nervous around other girls, but with a mature and woman as sexy as Grayfia, he felt almost as if he were a virgin once more.
Grayfia almost broke out a smile as she slowly mouthed over his fat cock, swiping the strands of hair that was blocking his sight, revealing her pretty face. She had such a lewd expression, suckling on him before taking multiple inches inside the depths of her mouth. Issei threw his head back from the warmth of her wet orifice, her hot saliva coating his turgid member. He had the urge to just grab onto her head and go wild, just like he did in those fantasies of his, but reality was obviously different and he was capable of restraining himself.
"Oh god!.. She's actually sucking on my cock.. This feels way better than I could even imagine!.." he grunted relentlessly as his fingers nestled into her hair, eyes closing briefly under the pressure of immense pleasure as she started bobbing her head into his crotch. Her technique was sublime, citing significant experience in this area, as Issei cooed in satisfaction as he was one of the lucky men who were privileged enough to enjoy the wetness of her blowjob. It felt so amazing that it could almost be considered sinful at this point, as Issei started getting a bit too comfortable, experimenting with a slight thrust towards her moving head. "Grayfia!.. You're so good!..." he groaned aloud, his aroused member teetering its limits as he throbbed in anticipation. Obviously he wanted to last much longer than he currently did, and regretted masturbating earlier, knowing fully well that he wouldn't be this close to cumming if he hadn't touched himself already.
"Sorry, Grayfia!... But- I'm about to cum!..." he grunted with his face scrunched up in pleasure, grip tightening on her luscious hair as she moaned in approval. Their erotic encounter was seconds away from reaching a miraculous, or for a word better suited, explosive conclusion. That is, until the sound of the door opening just a room length behind them interrupted the two. Grayfia's head immediately froze in place, as she was in the midst of a deep descent that had her nose pressed against his pubic bone. Everything was aligned in place for an erotic session of swallowing before their actions were forced to a screeching halt. "I'm home!~.." cheered an excited Rias, who unknowingly interrupted
her crushes and sister in laws steamy encounter.
Grayfia took her time peeling her head away from his tasty cock, not wanting to make any accidental slurping noises that would give away their location. There was a silent plop to her lips as she took Issei's cock out of her mouth, wiping the saliva from her face as she slowly rose to her feet. The young man was on the verge of freaking out before Grayia took charge, grabbing onto his wrist and pointing at his nakedness. "Put your clothes back on already!.. We'll have to take this upstairs.." she whispered to him, as the two rushed to get clothed whilst trying to remain as silent as possible. Rias was humming to herself as she was checking herself out in the mirror, typical of a young lady as popular as she was. Grayfia and Issei used this time to slowly sneak their way upstairs. Issei's heart was racing when he scooted his way up the stairs, managing not to fall in Rias's line of sight as she was still looking in the mirror.
"Grayfia!.. You home?.." asked Rias when she heard footsteps on the stairs. "Yes!.. I'm here, I'm going to be taking a nap now. So I'll see you sometime later, alright?.." said Grayfia, wanting to cut the conversation short. Her sister in-law had the tendency to talk up a storm at times. "Alright!.. I'll see you later then.." replied a slightly confused Rias, wondering why it seemed that she was in such a rush. Not paying it much attention, she went about her day as she lounged in the living room, listening to music with her headphones while searching for some snacks to munch on.
The door slowly creaked before closing behind them, leaving both Issei and Grayfia in the safe zone for now. Of course, there was always the risk of being caught and being too loud, but Grayfia tried to counter this by locking the door. "Grayfia!.. Can we please continue?.." he nearly begged, embracing her the moment they were alone together, grabbing her wrist and pressing his bulge against her palm. There was no pain he could imagine worse than that of being blue balled, and he desperately wanted this release no matter the situation he was in. "Yes, yes. Issei.. But, keep your voice down.. You wouldn't want to be caught, right?.." she whispered with a sly grin on her face, willingly rubbing his length before stripping him down once again. He was lightly nudged onto the large bed behind him, the cushions of the mattress making him bounce while she pressed onto his chest. Issei comfortably lied down as he tilted his head upwards, staring at the beautiful woman as she took him back inside her mouth. "Oh!." he grunted, eyes closing as his sensitive erection
desperately needed this level of stimulation.
The fact that he was unintentionally edged made it feel all the more better, and the adventurous rush that came with receiving a blowjob under the same roof as other people only further intensified the pleasure he was getting. Issei was already making sure he wasn't going to accidentally blow his load in his pants by holding back his ejaculation, but now that he was welcomed back into that intoxicatingly warm wetness, there was no reason to remain stagnant any longer. He quickly thrusted against her face to receive the utmost levels of stimulation possible, panting as he struggled to find the words to compliment or describe what exactly he was feeling, other than announcing his arrival. "Grayfia.. I'm cumming!.. Please.. In your mouth!.." he grunted profusely, fingers tugging at the hair that pulled against her scalp. "Mmhm!." she moaned while nodding her head, eyes opened and
staring back at the pleasured expression on his face. It seemed that he wasn't the only person that was turned on by this heartracing situation. "Here it comes!.." she thought to herself as she felt the first waves of semen bursting through, splashing into her mouth as she was immediately forced to swallow. Given his size, she was expecting a tough outing, but the results were almost a little bit too excessive. Grayfia had to swallow consecutive loads as her eyes shut tightly to focus on the task at hand, unable to enjoy the musky taste because of how intent she was on consuming the rest of his
hot spunk.
"Oh man!... She's sucking me dry!..." he thought with a look of ecstasy on his face, almost drooling from the sensation of her cheeks hollowing around his shaft. He was almost being treated like his penis was a straw, and his semen was the tastiest fluids in the world. That was the level of dedication that Grayfia was giving him, which almost sent him into a dreamy trance as he was finally granted one of the most pleasurable feelings in the world by the woman of his dreams. There were some rather loud slurping noises coming from Grayfia's mouth, unfortunately inevitable as there was no plausible way she could swallow him otherwise. Almost an entire minute went by until the seemingly never ending throbbing came to an end, capped off with a satisfied sigh as Issei ran his fingers through her hair. "That was amazing…" he panted, wishing he could ingrain the sight of her lips engulfing his cock permanently into his memory.
"Grayfia!.. Before you go to sleep, could you help me out with something?" a loud voice could be heard from the stairs, possibly Rias was heading up and closer towards their room. Unfortunately, there was no further time for conversation, as Grayfia pointed and urged Issei through the window. "Hurry!.. Before she catches on!.." she insisted, with Issei quickly nodding his head and following suit, lifting up the window and using his impressive physical abilities to strike a painless landing and escaping without being detected.
The walk home was filled with his personal thoughts, mind racing wildly after the crazed events that took place. The fact that he produced results in what he believed was an unrequitable love was too much for his brain to handle. "Holy shit!.. Did that really just happen?.. I must be the luckiest man in the world!... I wonder what this means for our relationship?.. Does she want to date me?.. Does she like me back?..!" he thought with a huge grin on his face. Even if it were just for a few minutes, he definitely wanted to clear the tensions between the two. The blowjob only serves to add more fuel to the fire.
The next day later…
It felt like it's been a while since the two have interacted since that fateful encounter, even if it was only a single day after, the wait made Issei's infatuation for her all the more worse. It was a bit crude, but he might've hung out with Rias at her house just to get another chance at seeing Grayfia. The previous night wasn't exactly considered the best sleep he's ever had, staying up for most of it when gushing and thinking about that sinfully hot blowjob he was the recipient of just hours prior. If he thought long and hard about it, he could almost imagine a replication of that very same feeling clutching around his member. Rias didn't notice, but it was almost like his mind was elsewhere the entire time they were supposed to be hanging out. Though, they've spent so much time together that she didn't really mind, enjoying his company no matter what they did.
However, Grayfia didn't seem to pop out of her room or interact with him while he was there.
Spending approximately two hours before he decided to call it quits, and announced to Rias that he was preparing to leave. The crimson haired lady hugged him goodbye before heading back upstairs, needing to catch up on some important homework that was assigned in class earlier on in the day.
Issei let out a disappointed sigh until a familiar voice interrupted him, his head turning almost too excitedly. "Issei?.. Could you stay for a few moments.. I'd like to have a chat with you for
a bit.." whispered Grayfia, to which the young man internally celebrated, and agreed to her proposal. Again, they had to replicate the same scenario from yesterday, sneaking up the stairs and trying not to make any excess noise. Luckily, Rias seemed to already be blasting music in her room, typically a necessity for the senior whenever she needed to study. She wouldn't be able to focus otherwise.
"So?.. What did you want to talk about?.." asked Issei, a bit anxious to hear her response. "Well.. As we both know, a lot happened yesterday.. Maybe a bit too much.." she said while suggestively licking her lips, which didn't fail in making the young man blush at the thought.
"Y-Yeah.." he responded, unsure of how to answer that. "Anyway.. I just wanted to assure you that it wasn't an accident…" she muttered, to which his eyes widened in response. "What did you say?.." he said, in shock. Leaning over to his right ear, dangerously close to the point where her lips were brushing against his earlobe, she whispered seductively "Did you enjoy the show?.."
He immediately understood what she was suggesting, remembering all of those times where she was seemingly teasing her with his body. The first thing he realized was that all of those times she was sunbathing, bending over, and even hugging him were all done with intentions in mind. However, it took him a bit longer to also realize what that singular statement meant. Which was the fact that she was aware of his habit of "secretly" masturbating to her. Issei wouldn't be human if that didn't
make him feel embarrassed at all, growing flustered after the revelation that threw him into a fit of flashbacks, wondering when the hell did she manage to catch on.
"W-What do you mean by that?..." he tried to feign ignorance, clearly unsuccessful in his approach when she didn't deter from her stance. "Hmm?.. I'm sure you know what I'm talking about.." she said teasingly, placing her hand over his thigh. Issei's face lit up red as there was no way out of this, only being left with the option of accepting the fact that the woman he desired was aware of his pervertedness. "I'm talking about this.." she said while standing up and stripping off her clothing, revealing herself in the same white bikini that she was wearing when he was ogling her from his window. His face lit up a deep shade of red as he quickly realized there was no way out of this, only capable of admitting his pervertedness.
"I've always known that you've been craving me, Issei.. I know all about those little games of yours, and how you'd always sneak glances at me.. While I admit that I thought it was cute.. Which is why I lost control of myself yesterday.. But, we both know that you want much, much more.. The question is.. Are you willing to do something about it?..." she whispered hotly into his ear. Her words triggered something internally with Issei, who's emotions of embarrassment were thrown completely out the window. This was finally his chance. After all of that time he spent fantasizing about her. This was his legitimate chance to finally fuck her. Grayfia had just given him his consent,
and that was more than enough for his erection to already grow to full mast. Boy, has he been waiting a long time for this. The apparent bulge on his pants threatening to break free from its confinements.
"Is that even a question that you need to ask?.. The entire time you were sucking me off yesterday..The only thing I could think about was how good fucking you would feel.." he admitted, wrapping his arms around her waist and pulling her half naked body flush against his. Issei had no time to be shy or flustered, asserting his dominance after Grayfia finally gave him the "green light" to proceed. Without the anxiousness of possibly scaring her off out of the picture, there was nothing else he had to worry about, other than accidentally slipping and having Rias find out about them. "My, you're suddenly very eager." she giggled, affectionately rubbing the front of his pants as she
hooked one of her legs against his sides. Issei grabbed onto her firm butt as he completely covered the distance between the two, kissing her neck while growling in arousal. They could faintly hear the loud music booming from Rias's room, letting them know that their odds of being caught should be significantly lower during this time period. There was simply no time to waste, it would be a tragedy if they beat around the bush for too long and lost their window of opportunity.
He toppled over her and shoved her onto the soft cushions of her mattress as he groped her womanly curves, addicted to the sensation of touching her voluptuous body. "This is it.. It's finally happening!.." he thought in excitement as he trailed his kisses up towards her lips, to which she responded by wrapping her arms around his neck, pulling him down with her as their tongues intertwined in a passionate kiss that both envisioned for the longest time. Issei's hands cupped her soft mounds as he relished in their elasticity and size, having trouble not getting distracted by the fact that he was finally touching her breasts.
The white bikini suit was definitely erotic, but he craved much, much more. He entangled his hands behind her back and untied the bra-strap, having issues stripping them completely off as he threw them to the wayside. He replicated the same action with her bottoms, before immediately dipping his fingers into her slick entrance. "Mmn!..." she moaned into the kiss, hips bucking from the direct contact, oblivious to the fact that Issei would be so aggressive. Grayfia had no prior knowledge that he'd been so popular and as a result, very experienced. His actions were a complete demonstration of this, feeling a bit overwhelmed by his talented skills. One would think that a young man who frequently peeked and secretly checking her out would be completely lost in bed, but Issei had her legs trembling without even fucking her yet.
"Can I put it in now?.." asked Issei as he briefly separated after tonguing her mouth, to which she responded by nodding her head, and then placing a light kiss on the lips. He couldn't help but grin as he fiddled with his pants before pulling them down, his raging boner angled perfectly with her tight snatch as he replaced his fingers with the bulbous head of his member, rubbing along her wet folds before slowly easing himself in. "Oh!.. Issei.." she yelped aloud, the thickness of his shaft slightly stretching her tight hole catching her off guard. "Ah… it feels even bigger than it looks.." she thought with her face scrunched in pleasure, loving the feeling of her insides having to accommodate his impressive size. The process of fully inserting himself definitely took a while, allowing Grayfia to really get the full compass of just how amazing his cock felt. "Ahn!... Issei!..." she whimpered, trying to contain her moans as best as she could to not alert Rias. The bed started creaking underneath their weight as Issei started wildly thrusting into her, groaning as he lightly bit down on the nape of her neck. One would think that he'd at least have the decency to restrain himself a bit, considering the fact that his best friend that happened to have a huge crush on him was only a few rooms over, but Issei had been waiting far too long for this moment, wildly pounding the beautiful
babe as her slick entrance squirted with every powerful thrust. "Holy shit, Grayfia!... You're way too fucking sexy!..." he cursed under his breath as his cock gradually started to pistoning and out of her sopping wet pussy repeatedly. Their loud noises echoed throughout the room, even escaping to the hallway. Luckily, Rias's mother seemed to be busy tending to the garden in the backyard, or else it would've been incredibly obvious as to what these two were up to. For all they knew, Issei was supposed to be leaving already, considering he wished them goodbye a few minutes prior.
"Oh fuck!... This really is the best feeling in the world.. I can't even…" he thought as he was struggling to properly think. He was unleashing a months worth, no, years worth of pent up emotions as he pounded her with all of his might. Grayfia's legs instinctively wrapped around his hips as she locked him tightly, falling addicted to Issei's huge cock. "It's so good, Issei!.." she affectionately
moaned into his ear as she rubbed the back of his head, almost as if she were petting him for performing at such an amazing level. Not only was this the roughest, but this was no doubt the best fucking she's ever received, wishing she could've prolonged both of their orgasms until the point where they could go at it all day.
In the other room, Rias was bobbing her head to the loud music as she hummed the tunes to herself, flipping the pages over of her book as she was completely focused in on her studies, only to be distracted by her reflection of the past week. "Hmm.. I wonder why Issei's been acting kind of weird lately.. Normally he's a lot more talkative.. Maybe something's bothering him?.." she pondered as she kicked her legs back and forth onto the mattress, noticing that his behavior was completely different than usual. It wasn't like he was mad at her or anything like that, but he seemed to be intent
on spending time with her, but always ends up leaving at abnormal times and not really interacting as much as they used to. His mind always seemed to be stuck in the clouds, as if he were imagining or always thinking about something else.
The cause of her worries were obnoxiously hidden right under her nose, as the two new pairs of lovers were steadily reaching their climaxes in the room down the hallway. "Ahn!.. Issei, slow down a bit.. What if someone hears us?.." she tried to whisper, only to moan halfway which interrupted the flow of her sentence. The horny young man took a few seconds to respond, as if he were too captivated or preoccupied with something, before snapping back to reality after she repeated herself for a third consecutive time. "Huh?.. Nngh, yeah, sure… But shouldn't you be doing the same?.." he grunted teasingly, as Grayfia failed to silence her moans despite the fact that her hands were covering her mouth. Issei tilted his head down to stare at her jiggling breasts, that moved with each of his incessant thrusts. Everything was just starting to be far too overbearing to handle, his shaft throbbing violently and hinting towards an impending ejaculation. "Shit, Grayfia.. I can't hold on
much longer.. I'm going to cum!~..." he yelled aloud, forgetting about the location and situation they were in. Grayfia recalled the sheer viscosity and size of the load she struggled to swallow just the day before, and imaging all of that swimming inside her womb made her legs tremble in anticipation. "Mmm.. Issei~.. Cum inside.. Just like you've always wanted to!.." she moaned loudly, eyes shut in absolute pleasure as his hands roughly squeezed the supple flesh of her breasts. "Here it comes!..." he grunted while biting down on his bottom lip, arching his back as he shoved the entirety of his cock inside while pushing balls deep. This was the same circumstances he's always envisioned, there
was no way he was going to allow any space between the two the moment she consented to getting creampied.
Enormous waves of his potent seed splashed inside her velvety walls, spilling from her lips the instant his humongous load travelled from the slit of his tip. "Ugh!... I'm finally cumming inside of you!.." he grunted while his face was shoved into the crook of her neck, breathing heavily as he shuddered relentlessly while using her tight hole to empty the content of his balls. "You are!~... You're filling me up!..." she whispered hotly into his ear, slowly becoming a slut for his jaw dropping skills in bed. He grunted profusely as he hung onto his powerful orgasm, Grayfia following shortly after as she climaxed violently onto his releases lasted far longer than usual, until they both lied on top of each other after needing a few seconds to catch their breath and recover.
"Jesus christ… That was fucking amazing…" he cooed, slowly rubbing her perky nipples as he couldn't keep his hands off of her naked body. "Me too.. That was so good…" she responded heartily, staring down at their connected crotches as he pulled out, his semen spewing out of her slightly stretched hole. "Huh?!... You're still this hard?..." she exclaimed in shock, already satisfied with the powerful orgasm that she experienced. "Y-Yeah.. I guess I'm way more excited than usual.." he laughed, his sturdy erection rubbing against her flat stomach. "One more?..." she asked, to which he rubbed the back of his head while nodding repeatedly.
The background music that could be heard paused for a few seconds, which made Issei's heart race as he stared back at the door with a bad feeling in his chest. There were footsteps heard that were approaching their location, as Issei panicked and tried to find somewhere safe to
hide. "Maybe I could ask Grayfia for some advice?.. She seems to be knowledgeable about this sort of thing, anyway." she said while lightly knocking on the door, before slowly turning the door knob in preparation to open the wooden door. "... No response?.. That's weird.. Oh, that's right! She did mention something about taking a nap.. I should probably wait till later', then." she said with a bubbly attitude, letting go of the knob and turning around and instead making her way downstairs.
Thankfully, after a few seconds passed by, nothing seemed to happen, as Issei couldn't think quickly enough to find a decent spot either way. There was a humongous sigh of relief from both Grayfia and Issei as they were frozen in place, almost out of fear from the immense tension and pressure they were under. "Shall we continue?.." muttered Issei under his breath, trying to be as secretive as possible as he suggestively grabbed onto her hips, flipping her over so her plump butt was facing him. "Oh?.. I didn't take you for an ass man, Issei.. Especially with the way you've been ogling my breasts.." she teased, to which he responded with a cheeky answer. "Nah.. It's just that you can't see me when I'm staring at your ass." he responded jokingly, gripping the squishy flesh in his hands before sticking himself in between her asscrack.
"Grayfia.. I want to take your ass.." he admitted, lightly thrusting against her anal entrance. She wasn't expecting him to desire something that adventurous, only getting the feeling that he was asking for a position like doggystyle or maybe even a buttjob. "You want to?-... With my ass?..." she said with a surprised tone to her voice, feeling flustered by the thought. It wasn't like she'd ever done anything like that in the past, none of her partners ever requesting such an illicit act. Though, if there was one man she would consider giving her anal virginity to, Issei would most definitely be
the one. They've been getting closer recently, and he was far superior in terms of looks in comparison to other men. Not only that, but he was packing some serious meat, and boy did he know how to use it. She's heard rumours about anal sex before, and they weren't always pleasant, but a naughty part of herself was intrigued by the prospect of it. "Alright.. Let's do it.." she whispered, unsure if Rias was still listening to music or not, considering the speakers had been turned down.
They continued forward and accepted the implicit risks, but thankfully Rias had alternated towards using earbuds as she ate dinner downstairs.
Obviously, there was a significant chance that someone could overhear them, especially because odds are they were about to be two times louder than earlier. Issei tried to accommodate this by draping the blanket over her head, trying to drown out the sound as he slapped her ass and made her pop her back out, making herself look as appetizing as possible before he started rubbing himself against her puckered hole. Grayfia was extremely nervous as her heart continued to race, biting down against the blanket as a reflex as Issei slowly forced himself past her anal entrance. "Nnghhh!..." she shouted underneath the blankets, toes crinkling as more of his fat cock was
shoved deeper inside of her ass. It was an extremely narrow fit, perhaps her hole squeezing him too tightly to the point where the base of his erection was being choked. Grayfia's screams of both a mixture of pain and pleasure were muffled underneath the covers, as the sensation was a far cry from that of vaginal sex. It didn't necessarily feel especially good at all, but there was a depraved part of her that enjoyed being fucked like a whore. He couldn't help himself but slap the firmness of her ass as he started repeatedly thrusting against her bottom hole, easily overpowering her due to the defenseless state she was in as the slamming of his hips caused loud slapping noises that were intimidated from their intatemely wild fucking.
"Oh, damn!.. You're so fucking tight!..." he groaned as his hips bounced against her ass, using enough force that nearly made ripples against her plump flesh. "Ungh!.. Harder, harder, Issei!..." she moaned from the top of her lungs, despite the fact that there was still the remnants of pain remaining. Grayfia couldn't help but meet his thrusts by shoving back into him, interrupting the momentum of his thrusts as they often met in a standstill that only deepened her anal penetration. Her vagina wasn't directly involved, but she was already starting to overflow with juices from being incredibly turned on, the sensation of having her ass filled unexpectedly lit a fire within her. "Oh, god!.. Fuck, Grayfia.. This is way too much.. Damn!.. I can't-.. I can't hold on any longer.. So good.. Way too good.." he grunted repeatedly, struggling to form coherent sentences as the pace of his hips lost its rhythm. Grayfia's response was almost indiscernible as her teeth were digging deeply into the blankets, the orgasm washing over her entire being proving to be far stronger than the previous one she succumbed to. He couldn't even form words to signal a warning as he threw his head back in absolute ecstasy, his penis spasming wildly before shooting heaps of semen deep within her anal cavity. The overjoyed young man nearly fell on his back as he clutched onto the meaty flesh of her large rump, appreciating her voluptuousness in all of its glory before finally surrendering to her womanly body. "Grayfia!..." "Issei!..." they screamed each other's name in unison, holding their voices back as the two shuddered violently from their respective releases. Their sweaty bodies and ragged breathing were the result of their extremely tiresome intercourse, as Issei lazily pulled out of her tight ass and rested his flaccid penis directly on top of the woman as he struggled to catch his breath. "Fuck… That was beyond words.." he thought, completely exhausted from the tiresome act.
The following day…
Issei was home alone, with his mother out shopping with Venelena, as he spent most of his day lounging on the couch as he scrolled through the channels of his television. Even while he was watching something that was meant to be intriguing, he still couldn't keep his mind off of the mindboggling sex he was blessed to receive just the night prior. "Man!.. I can't believe this is real.. I really did all of that with Grayfia!.." an extremely gassed Issei thought to himself, celebrating internally as he rejoiced in his well due success. There was a knock on the door that interrupted his show, causing him to pause it and skeptically peek at his house's entrance. "Is that?.. Don't
tell me.." his heart raced as he approached the door, opening it and revealing who the person knocking on it was. "Issei?... You mentioned that you'd be home alone tonight, right?... Do you want to continue from yesterday?.." she seductively whispered, flashing a bit of her chest and revealing a teaser of her lingerie.
"Man.. This is going to be the best day ever!.."