2- Sleeping with the Gremory's
Notes - All characters in this story are the age of 18 or above.
Contains - Cheating, Anal Sex.
Grayfia stretched her arms high towards the ceiling, yawning as she cracked her back. Her body was immensely sore and drained from energy as she was dealt a reminder of the events from the previous night. Not that they were any different than the rest, as she looked to her side and smiled at her sleeping lover. Both Issei and Grayfia had been in this relationship for around a few months already, and he'd always visit her late at night and sleep in her room after fucking for a few rounds of amazingly passionate sex. Which is why she always needing a decent stretch before going about her day, doing so before getting up to leave the bed after getting the urge to grab a glass of water. Cum wasn't exactly the most reliable source of quenching one's thirst, after all.
It was around an odd time in the night, unexpecting of anyone else in the household to be awake. Grayfia walked downstairs as she headed towards the kitchen, wiping her eyes as she did so. The only clothing she had on was a flimsy see-through shirt, and nothing covering her underneath but the panties she clumsily slapped on before hopping out of bed. As she half-awakened poured herself a cup of water, she heard footsteps coming from behind as she quickly realized her appearance, yelping when she heard someone's voice. "Grayfia?... " soft spokenly said Venelana, who didn't want to speak too loudly and accidentally wake someone up. "Y-Yes?.." she said nervously. Even though her clothing was rather suspicious, that didn't necessarily mean she'd been caught red-handed or anything. With that belief and hope in mind, she tried her hardest not to demonstrate any signs of distress, keeping a friendly smile on her face. "Listen.. I know what you've been up to recently."
said Venelana , so much for trying to maintain her cool. "Huh?!.. What are you talking about?.." she muttered, trying to feign ignorance as she nervously avoided eye contact. "Grayfia.. Don't act dumb with me.. I know of your secret affair that you've been hiding.." she said, with a bit of an angered tone in her voice. "What should I do?.. Is she talking about what I'm thinking of?.." she thought in a panic, wracking all the possibilities in her head to find a way out of this uncomfortable situation. Before she could continue and most likely dodge the question, Venelana pulled out her cellphone and pushed it directly in front of her face, playing a video that was all too familiar.
In the recording, it showed both Issei and Grayfia on her bed, being pounded in her favorite Mating Press Style as she tried desperately to contain her moans. "What is this?!" completely shocked, she covered her mouth. Not only was she discovered, but to have their act caught and filmed was beyond embarrassing. "Venelana ?!.. Why do you have that?.. You could've just talked to me about it.. Why go so far?.." she said, irritated. Her voice raised a bit too loudly, as she was immediately shushed by Venelana who didn't want to be overheard. "I placed hidden cameras in your room to make sure that what I was right.. And so you wouldn't be able to deny it.. Even now,
Issei's upstairs sleeping. Isn't he?" she said, hands on her hip as she interrogated her. ".Yes…"
she muttered in defeat, unable to find a way out. Venelana twirled her hair with her fingers as a deep silence took over the room, as if she were in a focused train of thought before finally breaking it. "Don't worry.. I won't tell anyone. That is, if you agree to my conditions.." she proposed, to which Grayfia let out a sigh of relief, after knowing that her secret hadn't been entirely revealed just yet. "Alright.. What is it?.." she responded, a bit weary of what she'd be asked to do.
Meanwhile… A few minutes ago upstairs…
Rias crawled out of bed to use the washroom, when she heard someone's voice raise downstairs as a bit of commotion seemed to begin. Shortly after, their voices quieted down, leading her to satisfy her curiosity as she stopped midway down the staircase to listen in on the conversation. It was a bit difficult to keep up with their discussion, but she swore she overheard some very sexual noises being played through a video. "Huh?! What the hell is mother showing Grayfia down there?..." she thought with a blush on her face, almost stumbling and accidentally revealing her position. "Even now..
Issei's upstairs sleeping. Isn't he?" she heard her mother speak, freezing her in place as she easily connected the dots. If memory served her correctly, the atmosphere had been rather odd between the two. Nothing of note had happened to raise her suspicion, but her intuition told her otherwise. It appeared that she was right, as she overheard Grayfia being exposed to sleeping with her best friend, and crush, Issei. Immediately, she went on to confirm whether or not this entire scandal was true, walking back upstairs and turning the doorknob on Grayfia's room. Just as her mother declared, there he was. Sleeping peacefully, naked in all of his entirety, oblivious to the commotion happening around him during his peaceful slumber. Rias had a betrayed expression on her face, shocked that it was actually true. Of course, they were never dating, but obviously a part of her was incredibly saddened at seeing the man of her dreams being taken by someone that was so intimately close with her. Right under her own roof, just across her own room.
"I can't believe this.." she thought while standing in place, her jealousy influencing her actions as she impulsively closed the door behind her, walking towards the sleeping Issei. She had a bashful expression on her face as she clutched her right arm, looking down towards his lower area that was conveniently covered by the blankets. Despite being nervous, Rias's hands shook as they reached over the covers, pulling them away as the object of her affection was finally revealed. "N-No way!..
It's this big and he's not even hard yet…" she thought in disbelief, his flaccid member appearing far larger than she could ever imagine. Her breath started quickening as her heart rate increased, the cock she'd been fantasizing about was actually in front of her eyes, albeit not in the same circumstances she'd envisioned themselves in. "If I do this.. Would he love me back?.." she thought with half-lidded eyes as her head slowly descended, gripping his softened member with her hand as she angled him towards the ceiling. Acting purely on her selfish desires, she closed her eyes and placed a kiss on the bulbous head. "It's so big…" she thought while placing yet another smooch on the tip, experimentally swiping her tongue along the tiny line. Rias had never done this before, but something sinfully wild awakened inside of her that made her feel like some type of sex goddess, giving her the courage to wrap her plump lips around the quickly growing object. "Ugh…" he groaned in his sleep, scratching his abdomen as Rias started sucking on his penis. Her tongue rested on the underside of his shaft as she played with his length while suckling with her lips, eliciting some
slurping noises as she felt his length steadily expanding in her mouth. At first, his meat felt soft inside of her orifice, and as it grew, the more rigid and long it'd gotten, catching her by surprise when she decided to push her head forward, gagging and being forced to back off when his erection suddenly threatened to slip inside the back of her throat. Rias peeked her eyes open as she stared down at the meatstick lodged deep within her mouth, licking lovingly around the head as she curled her crimson hair behind her ear, bobbing against his crotch a few times as the exotic taste made her incredibly aroused. "It's so hot and hard…" she thought with a flustered look on her cheeks, saliva trailing down the sides of her lips as she pulled out to stare at his erected manhood. Just like his personality and everything she admired about him, his cock stood proudly and strong, wishing she had a ruler at hand to measure how gifted this man was in this department.
There was an aching sensation in her chest as she took in all of the pleasured noises and faces he was making, at the back of her mind knowing fully well that there was someone else that's been doing this to him. Of course, she wanted to be first, and his only woman. But, reality isn't always kind to everyone, and Rias had to make do as she tried to stifle these depressing emotions. Instead, she packed all of those negative feelings into making her blowjob that much more passionate, quite literally making love to his member through the use of her mouth, affectionately kissing, licking and pampering his arousal with her lips and fervent tongue. It didn't matter to her if she were to get caught, not even bothering trying to conceal the lewd noises of her constant slurping, or wiping her face of any excess saliva that was produced from her sloppy blowjob. The only thing on her mind was pleasing this young man that had always captivated her heart, no matter how popular she was amongst the others, he was the only one she simply couldn't resist. "Issei.. I'm going to make sure I'm the only one that you keep your eyes on.." she thought while inhaling a deep breath through her nostrils, forcing herself forward and mustering all of her sheer willpower in an attempt to deepthroat his turgid length. Being her first attempt at a blowjob, the progress she made was amazing in itself, managing to slip a few inches into the back of her throat. Tears started forming in her eyes as she eventually choked on his thick cock, backing away and suffering from a coughing fit as she covered her mouth. Her legs curled as a sudden jolt of arousal travelled throughout her body, finding it incredibly erotic that she nearly choked on Issei's member. His groaning seemed to last much longer than usual when she tried to stuff her throat full, encouraging her to try again. This time, she wanted to survive for much longer, wishing that she could surpass Grayfia as a woman capable of sexually easing his probably rampant libido. "Not enough.. I need to go deeper!..." she thought as the empty space in her mouth was shoved full of dick, once again giving a second and final
attempt. "Come on.. Wake up, Issei!.."
No matter how uncomfortable or painful it might've been, Rias pushed forward all the way until her lips were wrapped tightly around the hilt. Her face was disgruntled in a mixture of pain and pleasure, saliva trickling down her lips as she struggled to breathe. Miraculously, she was able to control her gag reflex for longer than normal, digging her fingers into the sides of his hips as she started moving her head up and down his crotch. She managed to continue deepthroating him for a while longer, nearly being forced to back off when Issei instinctively thrusted upwards despite being in a deep slumber. This wasn't anything that could deter Rias from accomplishing her goal, repeatedly smacking her nose against his pubic bone as she planned to drive the man she's always been infatuated with to an incredible orgasm. "Oh!... Grayfia!~..." he groaned loudly in his sleep, hand lazily finding the top of her head as his fingers tugged at her hair, pulling against her scalp. Rias looked troubled as she kept her lips locked around his shaft, refusing to let go despite the fact that he called a different woman's name while reaching an orgasmic high. Almost serving as a warning sign, she felt his erection violently throb while being completely immersed within the walls of her tight
throat, eyes widening at the sensation. "Is he?!... Is he going to do it?..." she thought with a sense of exhilaration, hand descending underneath her panties and easily locating her wet folds, fingering herself to the tune of his moans right until he reached his apex. "Here it comes!..." she thought with her heart racing wildly, the constant throbbing almost felt like an earthquake with how intense the pulsing sensation was against her tongue, later becoming the lesser of her worries the moment that the huge splurt of white liquid started shooting directly against the back of her throat. His load was unlike anything she could've ever imagined, much larger than she could've deemed humanly possible, forced to pull his member from her throat and settle for finishing swallowing the rest that landed in her warm orifice. Her cheeks hollowed as she provided him with the utmost suction she could muster, slurping loudly as her tongue aided in her quest to complete this erotic blowjob as she lapped repetitively against the tip. His overpowering taste dominated her taste buds, unable to focus on anything other than the powerful ejaculation and odd texture that filled the entirety of her mouth. Rias's cheeks would slightly bulge for an instant before she continued downing his seemingly never ending load, struggling not to accidentally choke from the mass amount of semen travelling down her tired throat. "Oh my god!.. Grayfia, what's gotten into you?.. That was amazing.. You must be really turned on right now.." muttered Issei as he tilted his head upwards, awakening from his deep slumber as his vision took a few seconds to properly focus, quickly realizing that the woman he was expecting to see was an entirely different person.
"R-Rias?!..." he shouted, unable to conceal his shock when he found his childhood friend intimately consuming his load, catching her on the tail end of the operation when his climax eventually died down. Rias didn't bother responding until she was completely finished, satisfied with the heaps of spunk she'd swallowed and ending things off with a seductive kiss on the bulbous head, dramatically pulling up with her head tilted back after letting out a deep and satisfied sigh. "Thanks for the meal..~" she whispered seductively, winking at the blonde man who had a dumbfounded look on his face.
"W-What's going on?... Am I still dreaming or something?.. W-Why're you here, Rias?.." he asked, completely confused and left wondering as to what was going on. Issei wanted to further inquire on their situation before being immediately silenced by her finger, catching a slight tangy taste as it was the same one that was previously touching herself down there just a few seconds prior. "Shut up, Issei.. I'm still mad at you right now…" she said, ticked off because he wasn't moaning her name despite putting in all of that work to make him cum. "Huh?!.. Why are you mad?.." he muttered with her hand still slightly covering his mouth, leaving him wondering what that rather addicting taste on her fingertips were, but quickly compared them to something he'd been all too familiar with, the scent of an aroused pussy.
"I have my reasons.. And I'm not planning to forgive you for them, either. Unless-" the rest of her
sentence trailed off as she suggestively looked back down at his still rock-hard erection. "Unless you're willing to take my virginity.." she whispered hotly into his ear as she crawled towards him. "W- What are you talking about, Rias?!.. What's gotten into you, anyway?.. I never knew you were this aggressive.." he panted while having his thick shaft gripped, still sensitive from the previous labour he'd put his poor cock through just hours earlier. "Circumstances change.. I can't sit back and wait much longer.. Or else I'd end up losing you…" she said in an adorable voice, crawling on top of him
as a close up glimpse of her voluptuous body immediately shut him up. She was wearing a hot-pink nightgown that attached tightly around her curves, her nipples visible through the thin fabric, not a bra in sight as her pronounced cleavage left him with dirty thoughts and a rejuvenating boner.
Rias stripped her top off while she was talking, momentarily leaving herself completely nude with her panties already hooked down towards her ankle, leaving Issei's jaw dropped when she allowed her massive globes to plop out and jiggle loosely. Sure, he'd gotten a pretty good idea of how big they were through her uniform, and hanging out with her on a daily basis. But, seeing them in all of their naked glory was a completely different experience, comparable to that when he'd first laid his eyes upon Grayfia's sublime form. Issei felt speechless as she grabbed a hold of his chin, making sure that she was the only person he had his attention on. "Even though I'm still mad at you, Issei… There is something I have in mind that only you can do.." she whispered while aggressively clutching onto his girth, almost as if she were trying to claim him as her property. "If you want me to forgive you.." she said while lightly grinding her crotch against him. "R-Rias.. Have you done this before?..." he asked, taken aback by her sudden aggressiveness, finding it difficult to deny her charm and seduction. Technically, he wasn't actually in a relationship with Grayfia, but there was a bit of a sense of guilt somewhere deep down, but his erection was not to be denied. "Me?.. Of course not..
I've been saving myself for someone special.." she said while pressing her forehead on his, causing him to take an audible gulp as their lower halves rubbed more intimately together. "R-Rias…" he grunted, watching her whimper while she began separating her wet folds, taking the initiative as she lightly tapped against the bulbous head.
"Is she really serious right now?..." actually feeling flustered right now. While Rias was definitely an attractive member of the opposite sex, he couldn't really envision them in a serious relationship.
Sure, the thought of fucking her would occassionally cross his mind during one of his solo adventures in the bedroom. But he'd been too focused on Grayfia recently to have actually paid enough
attention to her, shocking him as to how easily he was being seduced by his childhood friend. Rias grunted loudly as she willingly speared herself with his cock, impaling her virgin pussy which induced enough pain to nearly cause her to yell. "Nngh!..." she muttered while covering her mouth in an attempt to silence her eventual moans, his impressive length proving to be a rather difficult challenge for a beginner. "Agh.. He's so big!..." Rias couldn't stop shaking her head in a fit of pleasure as her hips reactively wiggled from side to side, absolutely loving the sensation of being filled after getting over the initial pain of being penetrated. For someone who claimed to be inexperienced, she was certainly moving wildly if that were the case. Issei gripped tightly around her slender waist as he was left breathless from the sight of her voluptuous figure jiggling right in front of his very eyes. "Agh.. Rias.. Slow down!. Don't push yourself too hard.." he whispered into her ear, holding her tightly as he tried to minimize the level of noise they were making. Apart from the lewd noises she was making and her depraved movements, the two looked almost romantic with the way they were intimately glued together. The crimson beauty was riding an orgasmic high as she bit down on Issei's nape, hands roaming his broad shoulders and caressing the back of his neck as she concealed her frequent moans. The only sound they couldn't do anything about was the slick noises coming from her overflowed pussy, drenched in juices from her uncontrollable arousal as she desperately tried to ride herself to an orgasm. She had no idea how long it would've taken for Grayfia and her mother to finish their little chat, and finishing as soon as possible was probably in both of their interests. "So good!~..." she muttered into the crook of his neck, her hot breath rather ticklish as his sensitive erection was responding quicker than usual. His hands mindlessly trailed down her back and located her plump backside, helping her shove more of his length down her wanting snatch as she was practically left crying tears of joy. Issei's fingers kneaded her soft flesh as his face
scrunched up in pleasure, their fit of passion rapidly reaching an explosive climax as the bed creaked underneath their weight. Rias's hips swung erratically back and forth, his cock reaching deep within her insides as she found herself quickly addicted to the sensation. "You're so tight!..." he grimaced while still being left in disbelief of the extremely narrow fit, more accustomed to fucking a woman who'd possessed a lot of experience in the past. Rias's quivering pussy and trembling body was a sure sign that she was dangerously close to peaking, catching Issei's attention as he had a relatively good understanding of a woman's body at this point. "Are you going to cum?.." he whispered into her ear, which she responded by pulling away from his neck and nodding quietly.
Pulling out whatever tricks he had in his repertoire in order to guide her to an orgasmic bliss, Issei brought his head down towards her chest and hungrily took one of her perky nipples in between his hot lips. "Oh!~... Issei!..." she exasperated while holding onto the back of his head, encouraging him to continue. His skillful tongue rolled around the pink nub as he affectionately suckled on her sensitive tits, causing her entire body to shake in response as her gyrating hips grinded incessantly into his crotch. "Rias.. I'm going to cum!..." grunted Issei, still devouring her chest as his fingers grabbed tightly onto her round butt. "Me too!~.. Inside, finish inside!.. Ahn~... Please!~..." she moaned sexily, to which he responded to her pleas as both of their bodies shuddered in place, momentarily pausing and moaning into each other's ears as they reached a simultaneous release. Feeling Issei's cock pulsing like a heartbeat while dispersing a copious amount of his potent seed inside of her only served to intensify the waves of ecstasy Rias was experiencing, a bead of sweat dripping down her forehead as she shoved her face into the cook of his neck, hiding her bashful expression as his ejaculation took forever to subside. "So much cum!~... I love you, Issei!..." she moaned as her nails dug into his skin, panting heavily as her violent orgasm completely drained her
of energy. "God.. That felt so good, Rias…" panted Issei as he helped her off of his lap, watching as his study erection slipped from her vaginal lips, adoring how his spunk spilled from her outstretched hole as she plopped back onto the mattress from being exhausted.
Outside the door..
Venelana and Grayfia had already wrapped up their serious discussion, agreeing on the conditions that she laid out with the promise of keeping her affair a secret. With how careless Issei and Rias had been, they did a mediocre job of containing their voices, leaving their intimate noises completely audible and obviously attracting the attention of the two ladies. In her fit of jealousy, Rias accidentally left the door relatively open, a creak of light shining into the hallway as the door wasn't properly closed. It was a given that they would be eventually caught in the act, both Venelanaand Grayfia managing not to gasp too loudly in surprise and accidentally alerting the two newfound lovebirds.
"My daughter and Issei too?!.." thought a pleasantly surprised Venelana, looking over and noticing that Grayfia had shared the same sentiments. They only managed to catch them during the tail end of their act, and were spectators to the sight of Issei creampieing Rias with his ample seed. "Grayfia.. You stay here.." she said with her outstretched arm preventing her from entering. "Alright…" she muttered in response, watching as Venelana swung the door open and welcomed herself in. "M-Mother?!.." yelled a flustered Rias, covering her naked figure and private areas with
her hands, crossing her legs as she laid on her back with her head propped up behind some comfy pillows. Issei's face was pale white, an expression on his face as if his soul had escaped from his physical body. It took him a few moments to recognize the predicament he was in, clutching onto the blanket sheets and hiding his erected member. "I'm so fucked…" he thought as he mumbled on his words, unable to think of any plausible excuse. Not only had he already finished, but he was caught fucking Rias in Grayfia's room, leaving some pretty heavy implications at what had been going down. Little did he know, however, was that she was far more informed than he'd initially thought. "Calm down, Issei.. I'm not mad.. I've already known about you and Grayfia for a while now.. But, not my precious daughter too.." she teased, giggling as she covered her smile with her fingers. "She's not mad?..." he thought with a sigh of relief, his heart rate still out of control but at least he found some ease behind this absurd situation.
Now that he was settling down a little, and found it less difficult to maintain eye contact with Venelana, his cheeks flared up for a completely different reason other than embarrassment. "W- What is she wearing?.. Do all women in this household dress sexily when they go to bed?.." he thought as he immediately yanked his head in another direction, not wanting to get caught staring. Venelana had the appearance of a woman still in her prime, with a body that rivalled that of her daughter. Despite her age, it was a well known fact that demons aged much differently, maintaining her youthful appearance and sexy figure. It didn't help that she was wearing a flimsy purple nightgown that did a terrible job at hiding anything, even her shapely legs and probably backside too were exposed thanks to bottoms that resembled that of a tiny skirt. Venelana wore black stockings with a purple ribbon attached to her right leg along with fishnet lace gloves that reached past her elbow, and her skin was visible through the see-through outfit. "I-Isn't she a bit too dressed up?..
Don't tell me.. Was she planning on doing this?..." he thought as he shyly looked away, comfortable doing this sort of thing with Rias and Grayfia because he'd been so close with them, but being around a MILF like Venelana made his heart flutter. She started walking in his direction with her hips swaying from side to side, causing him to subconsciously hold his breath as the older woman approached him. "Mother?... What are you doing?.." asked Rias as she backed away further up on the bed, unknowingly clearing some space beside Issei which was eventually filled by Venelana as she took the seat on the mattress right next to him. "No need to be so shy, Issei.." she whispered while slowly lifting his blankets, causing him to immediately clutch them and pull them back before she could lay her eyes on the prize. "V-Venelana?!..." muttered the confused young man, unsure of what was going on anymore. "Hmm?... Don't be so shy.. We need to have a talk.." she whispered seductively, placing her slender fingers directly over the slight bulge on the blankets, gripping his length with the white sheets being the only thing separating the two. ""Y-Yes ma'am?!.." he stammered nervously, feeling blood pump his hardening erection back to full
capacity. "Mom?!..." thought a thoroughly confused and flustered Rias, having no clue how to deal with these oddly developing circumstances. Perhaps she would've done more to intervene if her legs and hips didn't feel numb, and her energy sapped from having sex with Issei.
The young blond had troubles controlling his libido, unable to deny his attraction towards the woman who'd essentially confessed her feelings for him just a few seconds ago. Allowing her to do as she pleased, Venelana lifted the white blankets that covered his lap, and clutched his girthy meat with her motherly hands. "You know, Issei.. You've been a really bad boy.." she whispered hotly into his ear, slowly beginning to stroke his length. "W-What do you mean by that?.." whimpered Issei, holding back his groans and unsuccessfully trying to hide his excitement. "Well~... You've been misbehaving recently, haven't you?... I'd be lying if I said that you've made me a bit jealous.." she said while quickening the pacing of her teasing handjob. "J-Jealous?... Why?.." he grunted.
"Because you've been playing around too much.. Like I said.. A bad boy is someone who'd not only sleep with my daughter, but my son's wife too?.. Did you enjoy it?.." she purred into his ear, sending shivers down his spine as he felt anxious by her surprisingly lewd voice. "I-...I-..." he stammered as he eventually fell silent, unable to deny his shameful actions. "S-She knows about Grayfia too?!.." he thought in a panic, but was immediately reassured when his shaft was pumped aggressively.
Venelana did a wonderful job at hiding it, but she'd been in heat herself recently. Not only had she not been apart of any action in bed for a significant amount of time, but this stress was amplified when Issei started fucking Grayfia nearly every night. The noises occasionally kept her up at night, serving as fuel for her late-night masturbation sessions. She couldn't keep down her urges any longer, wishing to relieve herself of this accumulated stress once and for all. "Issei.. Let me do this.. I promise this will be a night you'll never forget.." she whispered while stripping the seductive clothing from her body, Venelana's desirable figure appearing all the more enticing as the purple top came off her head. The three women were all incredibly gifted in terms of their bust sizes and there was really no way to tell which of them were superior in that department, his eagerness towards following through with this despite the prying eyes around him growing by the second. She purposefully left her stockings on as she wiggled her butt side to side, tempting the man as her see-
through panties chipped away at his defenses. "Is it really okay if I go through with this?!.." he thought as he glanced towards Rias, who had a conflicted look on her face as well. You could tell that she was a bit irritated, but for some reason she looked a bit horny too.
Issei's eyes focused back on the seductive vixen working her hands on his dick, leaning back and enjoying himself as he fully took in the magnificent sight that was her practically naked body. "Woah!.. She's drenched!..." he thought while peeking at her panties, noticing how wet the area was around her pussy. "You must be really turned on… To get all wet like that.." he muttered while getting off of his back, leaning forward as he suddenly inserted his finger underneath the hem of her panties, taking the initiative and stripping the soaked fabric off of her body. "Oh, my!.. Issei~..." she exclaimed, both surprised and excited by his display of manliness. "I can't take all of this teasing anymore.." he panted, a rush of adrenaline flowing through his veins as he moved away from the jerking of her hand, crawling behind her and positioning himself for penetration. Issei playfully smacked her thick butt while gripping onto her waist. "Ahn!.. What's gotten into you all of the sudden?" she replied sexily. "If it's a good fucking you want.. Then I'll give you exactly what you asked for.." he said, pulling her body flush against him, forcefully inserting his cock inside of her warm vagina, understanding that she was already lubricated enough to handle him. "Ahn!~..." she moaned from the abrupt penetration, his immense size and length catching her off guard as the pleasure induced was far greater than anticipated. "Oh goodness!.. It's no wonder both my daughter and Grayfia had grown so attached.." she thought while pushing her ass back against him, responding to his thrusts as their close skinship made noise as they slapped together. The busty brunette's figure looked immensely erotic from the back, the slutty outfit she was wearing accomplished its goal in turning him on. Issei figured that he didn't need to treat her gently, assuming that she was a woman matured enough to withstand whatever he dished out. His thrusts were vigorous enough to the point where you could hear the sound of his testicles slap against her butt, along with his cockhead passionately kissing her womb. "Oh!~.. Ahn!... Unbelievable!~..." she moaned repeatedly as she shook her head in disbelief, lifting her head and eyeing Rias who was evidently jealous. Venelana was cheeky enough to look back towards Grayfia who was still waiting at the doorside, purposefully being as loud as possible as she shoved her backside against his crotch.
The bed underneath them rocked wildly back and forth as Issei was finally able to fuck a woman
completely unreserved, unworried about potentially being too noisy as his sole focus was on pleasuring Venelana and himself as he continued pulling her against his thrusts. "Ah.. What am I doing?!.. I can't let her find out.." thought a flushed Grayfia as she managed to stop herself from touching herself upon watching the erotic sight. Meanwhile, Rias started pouting as she was powerless to do anything but watch. "Nngh!.. Ah, God.. Ahn!~." she cried as her hair swung wildly
in combination with her tits, her hourglass figure in full display as Venelana appeared to be steadily losing herself under the immense amount of pleasure. He caressed the smooth flesh of her large ass while nearly tipping her over, noticing that she seemed to be more sensitive than he'd initially thought, her toes curled and fingers grasping at the sheets as her tongue hung loosely from her mouth. Seeing her acting so unexpectedly vulnerable and willing to immerse herself in pleasure flipped a switch inside of the excited young man, fucking her more aggressively than before as he pounded relentlessly into her snatch. "Issei!~... Ungh!." she panted as she lost the energy to
reciprocate the movement of his hips, head turned back as she stared at the content expression on the man who was fucking her nice and extremely hard. "Good.. Good!." she repeated as her voice
shook from the significant force he was packing behind each thrust, already squirting numerous times as her vaginal juices made the tight fit extremely slippery.
Venelana found herself visibly affected by his fat cock, on the edge of an incredible orgasm as her legs started trembling as a result. "Mmm… I love it!~.." she heartily moaned, whimpering in pleasure as her back arched to grant him better access to her stretched hole. Issei was relatively quiet as a bead of sweat trickled down his forehead, breathing heavily as he felt her pussy squeeze him tightly. "I'm going to cum, Issei… Harder!." she panted as her forehead dropped onto the mattress, voice
getting louder as Issei dutifully finished her off, inserting as much of his cock as he could while aiming for her G-spot, discovering where it was located during his session of giving her some prime fucking. Wishing to guide her towards her release, Issei packed all of his strength behind those errant thrusts, causing Venelana to squirt relentlessly as his hips reached blinding speeds, appearing as a blur. "Mmn!~." she moaned as she shook violently, reaching a powerful climax as a large
amount of her sweet nectar squirted from her pussy. "Issei!~." said Venelana with her chin resting
on the mattress, head tilted up and incidentally catching a glimpse of Rias's envious expression. "Ha… Ha…. Why did that feel so good?.." she muttered while trying to catch her breath, unflexing her body as she momentarily relaxed.
Venelana was laid out flat on her stomach as Issei pulled out of her abused pussy, still producing enough vaginal fluids to the point where it spilled onto the mattress. "Thank you, Issei~." she
said, eternally grateful for satisfying her sexual needs. "Wait-.. I didn't cum yet, you know.." complained Issei, who's fingers once again started smoothing her backside, rubbing circular motions around her squishy flesh as it was evident he'd taken an interest in her ass. "Still?!.. Even after all that.. He's not satisfied?." thought a flustered Venelana, in awe that Issei managed to turn
the tables around as she was originally the aggressor, loving the feeling of being handled roughly as her arms were suddenly grabbed from the back. Her asscrack was suddenly filled by Issei's throbbing erection as the rigid member started rubbing against her back entrance. "W-What are you planning on doing?.." she muttered with her heart racing, her engorged pussy quivering at the imagination of what Issei was preparing to do to her. The anticipation that was building up from the sudden silence that overcame them made her anxious, feeling his cock rub intimately against her puckered entrance, gasping when she felt him pull his hips back and then press the bulbous head against it. "Is he-... Is he really going to?-" she contemplated while turning her head to stare at him,
analyzing his expression as she quickly realized that he had been overcome with sheer lust and desire. It wasn't like she was against anal sex, but having never done it in the past, she couldn't
help but feel a little bit fearful when the intimidating erection started warming up against her big butt.
"Venelana.. Is this alright?.." asked Issei, managing to regain his consciousness as he made sure to receive consent. For some reason, this made her feel incredibly hot, biting down on her bottom lip as she nodded her head. "Yes.. Do it… Give my ass a rough fucking!~..." she pleaded as she threw away any sense of morality, fully indulging in her sluttiness as the older woman had always wished to sate her carnal desires, looking for a man who was capable enough of drilling her into pure exhaustion. Issei obliged as his slippery member shoved its way inside of her anal entrance, outstretching the tiny hole significantly as he took her anal virginity. "Agh!~... No way!.." she panted as she squirmed underneath his grasp, a completely different sensation than the vaginal sex that she'd been accustomed to. Even for Issei, the narrower fit and temperature was a different experience, causing him to grunt profusely as he'd already been nearing an ejaculation. "Damn!...
Your ass is so tight!..." he complimented as he yanked against her outstretched arms, lifting her upper half from the bed as he arched his back completely. Issei's thrusts caused the mattress to start bouncing up and down as he dominated her asshole, pistoning in and out of it in a hurried search for nirvana. He was already so close, and this was icing on the cake as Velemna's
disgruntled moans turned downright erotic, almost incoherent as getting fucked this hard and abruptly was something she clearly wasn't prepared for. Rias whimpered as her fingers shamelessly descended down towards her crotch, covering her mouth to hide the apparent blush on her cheeks as she had a first-seat view of the entire spectacle. Unable to take it any longer, she crawled towards the two fucking like animals and grabbed Issei's chin, pulling him into a hungry kiss. "Mmph!.." he muttered while continuing to fuck her mother, undisturbed by her sudden actions. Grayfia had to muster the strength to grip her own arm to prevent herself from masturbating, but was breathing heavily and leaning against the wall as she couldn't stop peeking at the mother who was gracefully drowning herself in lust.
"Oh, yeah!... This is what I'm talking about!... Hold on.. You're gonna make me cum!..." he panted breathlessly as he tightened the grip around her wrists, pummeling her limped form powerfully against the mattress as his eyes shut tightly, face scrunched in absolute pleasure as he shoved balls deep. "Cumming!~." he cried out with his hefty shaft pulsating incredibly, a mass amount of seed
being dispersed directly inside of her anal cavity as the warm liquid could be felt spraying against her inner walls. For a brief moment, Venelana's eyes rolled to the back of her head as she nearly lost consciousness, unable to recover after a fucking this forceful and pleasurable, immediately falling limp against the mattress after their connected bodies vibrated for nearly a minute. Issei grunted as he slowly pulled out of her abused ass, letting go of her arms as they plopped onto the soft cushions, pushing up against the mattress to aid in his retrieval of his cock. He pulled out slowly to relish the feeling of her tight booty, finding that this short instance was one of the sexiest things he's ever done. "My god.. That was amazing, Venelana-" he said while noticing that she passed out, all of that moaning and screaming made it sound like she was seriously aroused, but it impressed himself that he managed to make a woman of her stature completely lose herself under pure elation.
"N-Issei… Me too… Please~." pleaded Rias, who had her legs spread out with her hands
supporting the underside of her thighs. "Hmm?.." asked Issei as he stared at Rias hop off the bed, pressing her arms up against the wall as she stuck her butt out at him. "Hey.. Don't tell me.. You want me to?-" his question was immediately answered when Rias voluntarily split her buttcheeks
apart, showing him her puckered hole as the dripping folds just inches below displayed just how horny this woman had been. Issei would be lying if he said he didn't enjoy anal sex, somehow
maintaing life in his once softening erection, revitalized by Rias's willingness to get fucked in the ass. "Are you sure you could handle this?.." he asked her, remembering that she tired out after cumming just a singular time. "I don't know.. Just do it!~." she complained, the exhilaration and adrenaline
she received from being this aroused made her feel immune to fear, instead anticipating having all three of her holes filled by Issei. The young man made sure to be patient this time around, knowing how overwhelming losing one's anal virginity could be after witnessing how Venelana reacted. Rias wiggled her butt in excitement as she felt Issei close the distance, propping her back entrance as she teasingly rubbed back against him. His hands found its place around her hips as he clutched her voluptuous figure, feeling up and down her curves as he fondled her body while lightly pressing against her asshole, making sure to properly align himself before inching forward, jutting his hips as she screamed loudly in approval. "Ungh!... It's in!~." she cried out as she pushed her ass
backwards, forcing more of his length inside as she whimpered as a result. "Don't push yourself too much.." said Issei as he grunted from her ministrations, slowing down his movements knowing fully well that Rias's overeagerness would potentially push her far past her limits. He placed his hand
over her arched back to slow her down a little, holding her in place as he started thrusting against her plush rump. "Ah.. God… Why are all of you so fucking sexy.." he panted in between breaths, hands roaming up and down her slender and yet busty body as he located her bountiful breasts, grabbing two handfuls of them as he pounded her butt to a pulp. "Angh!~... Oh!.. Oh!... So good!." she
cheered as Issei began overpowering her, crotch slamming repeatedly against her. It was a lot more painful than regular sex, but the pain brought with it another sense of pleasure, making the crimson beauty realize just how dirty she was deep down inside, absolutely addicted to the feeling of being drilled against the wall.
"This is so hot!." panted Issei, not expecting a response from Rias as she was too busy moaning
from the top of her lungs, legs shaking and struggling to keep herself from falling as she was steadily losing form. Issei held her up in place with his strong arms as he hugged her tightly, biting the back of her neck as he began twisting her nipples, providing some extra treatment as the act caused Rias to lose control. "Mmnnghh!~." she screamed as her vaginal juices started dripping down her leg,
dangerously close to another orgasm. "Mmm…" Issei groaned into the side of her ticklish neck, an overbearing amount of sensations happening all throughout her body as Rias reached her peak. "I'm cumming!~." she choked out as she came furiously, squirting more than she's ever had in her
life as her legs lost its strength, carried by Issei's hands as he gave her a final thrust for emphasis. "Agh!." he grunted as he started ejecting himself, pouring an ample amount of seed inside of her
anal cavity before falling back onto the bed, bringing Rias with him as she sat down on his lap. Issei lifted her legs apart to watch as his throbbing erection continued pouring his warm spunk into her asshole, pulling out with a wet plop after ten seconds, his slippery member smacking against his leg. Issei let out a satisfied sigh as he caught himself with his elbows, giving Rias a smack on the butt as approval as he slowly lifted her off his length. "Ah… Amazing…" she whispered, slowly fading away as she suddenly fell asleep, another passed out after an amazing round of sex as Issei laid her comfortably onto the nearby pillow. "Just like her mother, huh?." he thought while looking at the
two beautiful buxoms, naked and in a deep slumber from being pleasured by his sturdy cock.
"N-Issei…" he heard a soft spoken voice come from the entrance of the room. "Grayfia?.. Were you there the whole time?.. Sorry.. I didn't notice with all of the commotion.." he muttered while rubbing the back of his head, laying down himself as he felt completely drained from the incredibly exhausting night. "Care to join me?.." he invited Grayfia with open arms, to which the silver-haired beauty accepted his offer, walking over and crawling onto the bed and cuddling his shoulder. "Ah.. It's finally dead.. Sorry.. But, we're gonna have to continue this tomorrow.." said Issei as he noticed his dick
had gone limp, unable to please her for the rest of the night. "It's okay.. You must be tired after having to endure all of that.." she whispered into his ear. "Yeah, I am.. But.. A man wouldn't dare to go to bed and leave his woman unattended.." he teased while removing his arm from the back of her head. Grayfia had a quizzical expression on her face as she watched Issei crawl on top of her legs, removing her soaked panties and pulling them down her slender legs. "Oh, Issei!... Wait.. I'm still sore.." she complained, but her fingers immediately tangled with his hair. "Then… Thanks for the meal…" he said while digging in, eliciting a loud moan from Grayfia.
The night had certainly been an eventful one. Leaving all of the women in the Gremory household completely exhausted, with Issei probably unable to muster any cum after being milked dry. If he tried, he'd probably have shot blanks. However, it was obvious that life had taken another unexpected turn for the young man, and an amazing one at that. After everything that happened, Issei had the best sleep of his life, cuddling with the multiple women clinging to his sides. What couldn't happen in reality, happened in his dreams, as he enjoyed another lustful night in one of his fantasies, a perverted grin on his face. "Ah.. The Gremory's are the best.."