Grayfia's Drunken Night 2 WIP (Highschool DxD)

A gentle smile came to Grayfia’s lips as she turned her attention to Motohama, looking the young man in the eyes while gesturing toward the bar. “Would you do me a favor and make me another drink before we take things any further? I’m getting thirsty and teasing you cute boys isn’t helping.~” Without waiting on him to get behind the bar, she found a seat beside Issei that allowed her to sit and wait on her new drink while she enjoyed the sight of these young men. Of course, with Motohama having tried to sneak a picture of her, he was on her shit list in the back of her mind. But Issei? Issei was a sweet boy that seemed to genuinely enjoy her presence and being with her.

Unfortunately, just as she was eying Issei, her gaze drifting up and down his body while he watched Motohama pour her drink, Grayfia heard the two of them chuckling. And she immediately turned her head to see Motohama pouring her beer from the tap. “Is something on your mind?”

“How about we have another bet? Double or nothing?”

The thought caused the smile that was on Grayfia’s lips to fade away for a moment. Double or nothing? Was Motohama that annoyed at the fact that he was wrong about her bust size? Was he that determined to get pictures of her to keep for himself, or maybe even share around? She wasn’t sure if she should allow another bet to happen, unsure if she wanted to even humor the idea since she was just out to have a night of fun.

But when Motohama brought her the beer that she asked for and carefully set it on the table next to her, she simply looked into his eyes and playfully licked her lips. “What do you want if you win? And what do I get if I win?”

Motohama stayed silent for a moment as he watched her bring the beer to her lips but not drink from it right away. “I screwed up by trying to sneak pictures of you. I should have at least asked. So, if we win this bet, we get to take pictures and record you for the night while we fuck you as much as we want, upping our win of being able to touch you. And if you win, I erase your tab from our system in the morning. You get to drink for free the entire night. Or until my parents come back tomorrow.”

The idea of not having to pay for her drinks was certainly tempting. Especially with just how much she knew that she would be drinking with just how hot and excited these boys were trying to make her feel. And, being able to stop them from taking pictures would be a good way to make sure no one found out about tonight. Though once she started drinking the beer Motohama brought her, Grayfia also knew that she wasn’t drunk enough to genuinely enjoy making love to these two if she ended up losing the bet.

“You’ve got yourself a deal. Last time must have just been a fluke for Issei’s luck. So, how about we make the game a bit more fair?” With one hand, Grayfia tilted her beer back and started to chug it right in front of the boys, unashamed of just how quickly she downed the beer. With the other hand, she gestured to the dart board that was across the room from them. “From here, whoever can hit a triple bullseye, or gets the closest to it, wins the double or nothing bet.”

As she set down her beer, she watched as the two boys shared a quick look and then nodded their heads. Right before Motohama made his way behind the bar to grab the darts for them to play with. Her lips curled into a gentle smile as she was almost sure that she couldn’t lose something like this. She may be a little tipsy, but she was still a devil and had plenty of benefit going for her. She gently bit down on her lower lip as she threw all three of her darts, one after another.

Much to her pleasure, two darts hit the bullseye and one strayed slightly to the right, getting just far enough to not count as a triple but leave her pretty close and almost guaranteed to win their little bit. However, much to her disappointment and shock, the moment that Motohama pulled her darks from the board, Issei threw all of his at once with a strange sense of confidence. And that confidence paid off as all three of his darts hit the bullseye and none of them strayed from their target.

It was right at that moment that Grayfia knew his luck was no fluke. In the back of her mind, she knew that it didn’t matter if Issei was just that lucky or if he was just that skilled. He won both of their bets and had won the right to use her body as he pleased. However, she knew that she still wasn’t drunk enough to let the two of them have their way with her. A heavy sigh left Grayfia as she grabbed the mug that Motohama had brought her a moment ago, holding it out to him. “You two won the bet, there’s no denying that. Unfortunately, I’m not drunk enough to let two teenagers have their way with me yet. I’ll need a few more beers before I reach that point.~”

When Motohama took her glass from her, Grayfia turned her attention back to Issei. There was so much that she wanted to ask him. Like if he just didn’t know he was skilled at games like this, or if he was just that lucky, or if he was doing it just so he could have even more fun with her body. However, the only thing she was able to do was wrap her arms around his neck and pull him to her body, caressing his head against her breasts and letting out an almost unsatisfied sigh. “If only you were a bit older, Issei. You’d be a treat for any woman.”

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It didn’t surprise Grayfia that, after her confession of not being drunk enough yet, Motohama brought her two mugs of beer to chug down so they could have their fun. She knew that he wasn’t trying to hurry her up so they could have their way with her but to instead get her comfortable with the idea of sleeping with them both. It warmed her heart a small bit that he would go from trying to sneak pictures to making sure she’s comfortable.

Fortunately for her, the boys were also more than willing to accommodate some of her niche fetishes in order to get her more hot and bothered. A lustful smile graced her lips as she held out one of her beers with one hand, watching as both of the boys stroked their shafts while pointed directly at it. All the while, she was downing the other beer and watching as they pushed themselves closer and closer to a climax. Her heart started to race in her chest as her gaze drifted back and forth between the two, watching as Issei had a slower and more deliberate pace to his stroking while Motohama seemed to have a quick and fervent pace. Almost like he just wanted to get it over with and see her drink his cum.

Grayfia playfully licked her lips just as both of the boys came in her mug of beer, an excited gasp leaving her at the sight of rope after rope of their seed plunging into her beer and even going as far as to stain the glass itself. Her heart continued to race as the boys pulled their dicks away from her glass, allowing her to drink it. And drink it she did. Grayfia didn’t hesitate to bring it to her lips and start swallowing each and every drop of her now cum-mixed beer. Nor did she care about the fact that some of the alcohol dripped out of the corners of her mouth and down her chin, dripping down onto her breasts until she fully downed the beer.

But once she pulled it away from her lips, Grayfia’s heart seemed to soar in her chest. The mixture of cum, alcohol, and excitement that filled her prompted her to almost immediately be okay with playing with both of the boys. Especially when she noticed Issei bringing his hands to her breasts to scoop up a bit of the alcohol that she missed onto his fingers. And with a smile on her face, Grayfia immediately popped Issei’s coated fingers into her mouth, playfully licking and suckling on them in order to get them clean.

When she popped his fingers out of her mouth a moment later, Grayfia kept a gentle hold on his hand while looking him in the eyes. “Since you’re the sweetest boy in this room, Issei, what would you like from me tonight?”

“W-Well…” Issei’s cheeks flared a dark shade of red as he looked into Grayfia’s eyes, a gaze of pure seduction and dominance looking back at him. “I-I want you to r-ride me while I get to stare at your tits.”

“Done.~” There was no hesitation as Grayfia grabbed a gentle hold of Issei’s body, pulling him around so that she could push him into the seat that she was just sitting in. And the moment that he hit the seat, she climbed herself into his lap, and wrapped one of her hands around the base of his throbbing shaft. She could tell just from the look in his eyes how excited he was to lose his virginity to someone like her. And she could also tell just how turned on he was by the way his dick throbbed and pulsed in her hand, a small bit of precum already leaking from his tip. “Take a breath, Issei. I’m not drunk enough yet to lose myself in front of the two of you, but I want you to enjoy this. I want you to be able to look back on this and love every second of it.~”

Grayfia playfully dragged her tongue along her lips as she slowly and carefully lowered herself down onto Issei’s cock, gasping as the head pushed against her inner walls and slightly stretched them out. He wasn’t massive or even as big as her husband, he for someone his age, Issei certainly had nothing to complain about. Her lips curled into a loving smile as she looked into Issei’s eyes the moment her rear end connected with his thighs. “How’s it feel having given someone like me your virginity?~”

“Fantastic.”

The word left Issei almost breathlessly and effortlessly, causing Grayfia’s heart to warm in her chest once again. He really was a sweet boy that simply wanted them all to enjoy the night they had together. She carefully wrapped her arms around his neck and leaned in close enough to steal a gentle and loving kiss from his lips. The kind of kiss that clearly made Motohama jealous by the sound of his whining next to them. Fortunately, Grayfia was able to ignore Motohama as she focused solely on Issei for now. “You said you wanted to stare at my tits, right? Then how about I give someone as cute as you a bit of a show?~”

Without missing a beat, Grayfia brought both of her hands behind her head as she leaned back, giving Issei a wonderful view of her plump and shapely breasts that, surprisingly, had absolutely no sag to them. She immediately started to sway her chest from side to side as she bounced on his cock, watching as his eyes were completely locked on her breasts. And as she picked up the pace of her bouncing, working herself into a steady rhythm of riding his cock, Grayfia made sure to keep her breasts moving at the same pace, making them practically dance for him.

She didn’t shy away from making them bounce and heave in front of him, completely captivating him with the sight of her lovely breasts moving. Nor did she stop swaying them from side to side as she felt him throb against her inner walls, lighting her up inside and making her more excited for just what the night was going to possess for them. “How do you like my titty dance, Issei? My breasts are putting on a show just for you.~”

As she spoke, Grayfia brought one of her hands to Issei’s cheek to caress him and keep him looking at her breasts. She easily felt him getting closer and closer to his climax as she continued to bounce on his cock, so much so that she wondered if he would even be able to hold out long enough for her to stop him from cumming inside of her. However, when she saw a look of pure joy on his face, and a few tears stinging the corners of his eyes, something inside of her told her that it would be a much better experience for him to cum inside of her. “You’re such a sweet and caring boy, Issei. What do you say we make this special for you? I don’t want you to cum inside of me, but--”

Unfortunately, just as Grayfia was about to tell Issei to not cum inside of her, he did just that. His cock erupted against her inner walls and filled her to the brim with his seed. Rope after rope of his thick and hot seed flooded into her cunt, some of it even pouring into her womb as she impaled herself on every inch of his member once again. And the feeling of him cumming inside of her pushed Grayfia over the edge and into her orgasm.

Her inner walls clamped down almost like a vice around his cock as she stayed in place on his lap, her heart and mind both racing with how to get out of this situation. However, when she felt his hands gently glide along her skin from her hips to her breasts, she knew that scolding him wouldn’t do anything good for anyone in the room. So, instead, she smiled as she brought both of her hands to his cheeks, pulling him into yet another loving and gentle kiss. “You did great for your first time, Issei. Though, let’s see if you can last longer once I have some more beer in me. I want to let loose with you two, after all.~”

One glance at Motohama, and it was clear that she wanted more alcohol. Thankfully, he was quick on the uptake and rushed to pour her a few more glasses. “Such an obedient boy when he gets to have his way… I’ll have to keep that in mind.”

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After a few minutes of downing drink after drink after drink, Grayfia finally felt herself slipping into that point of drunkenness where she could really let loose. She was still sober enough to remember anything that was going to happen tonight, and even to call things off if the boys tried to go too far, but she was finally at a point where she didn’t feel the need to hold back. And that was very clear as she strutted her way away from the bar, her hips swaying with each and every step that she took. All while both Issei and Motohama stared at her plump rear end.

When she got far enough away from the bar to be satisfied, Grayfia brought both of her hands to her ass cheeks and gave them a firm grab, forcing her fingers to sink into the soft skin of her ass cheeks. But she didn’t say a word to either of the young men before smacking her ass and making her cheeks jiggle for them both to see. Though, a quiet and seductive giggle did leave her as she turned herself around and lifted her right leg into the air a little bit. Just enough to be able to hook her right arm underneath her knees. And the moment that she had a firm hold on her leg, Grayfia hoisted her leg high enough in the air to perform a vertical split for the boys.

The clearly wet spot in her panties and the smile on her lipstick-stained lips clearly caught the boys’ attention, both of them getting hard once again just from simply looking at her do this. And the fact that they were as turned on as they were while simply watching her move lit something inside of Grayfia. Something that prompted her to spin around on her heel while leaving her other leg high in the air. Something that caused her to lower her leg while facing away from the boys until it was parallel to the ground. The moment it was, another giggle left her lips as she plucked the string on her panties, causing them to snap and fall to the floor and fully expose her ass to the two of them.

In the back of her mind, she could’ve sworn to hearing both of them gasp at the sight of her running her own underwear just to put on a show for them. But Grayfia didn’t have a single problem with that as she lowered her leg back to the ground, placing her foot against it and bringing both of her hands behind her back to undo her bra. Fortunately, she turned around in time to see Motohama getting closer to her just as she undid her bra, the fabric falling to the floor and revealing her breasts just in time for him to grab a firm hold of her waist. “Well, someone’s certainly eager after all that.~”

As she spoke, Grayfia found herself stepping back toward the wall as Motohama gently pushed her, clearly wanting to pin her against it as he had his way with her. And she didn’t stop him, even as he grabbed onto her thigh and began to lift her right leg in the air once again. Without saying a word, she knew exactly what he wanted from her and easily hoisted her leg into the air to do a vertical split once again right as her back connected with the wall Motohama wanted to fuck her against. “Don’t hold back now, Motohama.~”

Fortunately for her, that was exactly what Motohoma did. He didn’t hold back in the slightest as he plunged each and every inch of his hard cock deep into her tight pussy, bringing a moan from both of their lips. For just a moment, he remained still as he was buried inside of her, enjoying the feeling of her inner walls quivering and convulsing around his shaft. And once that moment was over, Motohama began to rock his hips back and forth inside of her, plunging his cock as deep as he could into Grayfia’s cunt.

Much to her surprise, Grayfia felt Motohama also wrap his lips around one of her breasts, suckling on her soft and full mound while he fucked her. With instinct and bliss running through her, she brought her hand to the back of his head and held him there as he sucked on her nipple, his tongue dancing around the hardening bud as he fucked her. “That’s a good boy. I didn’t think you’d be so good so young. But you two are just full of surprises, aren’t you?~” Grayfia playfully tangled her fingers into Motohama’s hair as she looked across the bar to see Issei looking at the two of them with pure jealousy on his face.

A gentle giggle rumbled in Grayfia’s throat as she watched him sugar and look at her like he wished he was in Motohama’s place. “Is something wrong, Issei? Are you jealous of your friend?~” She teasingly dragged her tongue along her lips as she watched him nod his head and take a step closer to them. However, she didn’t give him what he wanted, keeping herself pinning against the wall as Motohama hammered away at her pussy.

Grayfia simply watched as Issei tried harder and harder to control himself and not rush over and start fucking her with Motohama. It was only fair to his friend, after all. Issei had his chance to fuck her and now Grayfia was giving Motohama that same chance. Though, as she watched Issei stare lustfully at her body, something inside of her wanted to coddle to him and give him what he wanted. Something inside of her pushed her to gently get herself off of the wall without pushing Motohama off of her.

And once she was in a position where she could move freely, Grayfia moved the hand that was on the back of Motohama’s head to his side, keeping a firm hold on his hips as she bent herself over backward so that Issei could have access to her throat. “You’re being such a good boy, Issei. Come fuck my throat while Motohama enjoys the pussy you just finished filling with your cum.~”

Grayfia’s heart raced in her chest as she faced away from the wall now, having Motohama’s back toward it as she watched Issei step closer and closer to her. It was so cute to hear that he was able to get jealous of his friend after having just fucked her, but it was that cuteness that prompted her to give in and let Issei have his way with her one again. And when his cock was right in front of her face, she didn’t say a word to him. Grayfia simply looked into his eyes before pressing a gentle kiss against the head of his member and playfully swirling her tongue around it.