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Instructing the Bold Dragon	By : BakaMazoku Category: -Misc Anime > Het - Male/Female Views: 10744 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own DxD High School nor the characters in it. I really don't. Not making a single cent off this.

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There are a number of people who would say that Grayfia Lucifuge was a monster. An absolute existance that could not be stopped. It was by her hand that things displeasing to the Gremory family simply... disappeared.

The Strongest Queen. The Silver Haired Queen of Annihilation. The Untouchable.

She was held up as the ideal of romance in the stories about her and her husband. And yet, it was a lonely existence... for to stand above was to stand alone. At least for a given value of alone, she had her family.

Her husband. Her in-laws such as that troublemaker Rias. They were all who mattered to her. Which was why she was rather concerned about Rias and that boy she liked. There was the way he held himself back, perhaps out of some concern or trauma he had.

And today, because of that very concern, Issei found himself called. With little explanation given, save that he had to come alone.

"So, um... Why am I here?" He asked the silver-haired maid. He did what was asked, but had yet to receive an answer from her.

"It has come to my attention that my troublesome sister in law has some feelings for you, and that you perhaps have feelings for her." She replied after sipping at her cup of tea as she sat looking out the window behind Issei. "Tell me, is this true?"

"O-Of course it's true!" Issei claims. Denial would have been an incredibly stupid lie given everything he did for her.

"Good." She nodded firmly at the way the boy replied. There was a conviction here in that voice that could not be denied, a burning passion as it were. The only issue really was... "So, you care for her, and it's obvious she cares for you. Even if she might not say such out in public. Thus, I must ask... why you're not doing anything about this, doing nothing more than giving puppy eyed looks at each other."

"Well... that..." Issei muttered, caught flat-footed. "I wouldn't want to do anything she didn't want to..."

Images flashed in his mind. Images of the first girl he loved.

How she had simply toyed with him, how she called him pathetic.

How she had begged him for her life and how he simply told Rias to end it all.

He knew, in his brain, that Rias wouldn't object. That others wouldn't. But logic held no power against fear of messing it up.

She could see the fear in his reply, the way he held himself, the way he faded into silence. "The Issei I know wouldn't be afraid. He would go forth bravely and overcome all obstacles if he needed to."

"But..." He muttered. "It's not like it's a fight to overcome here..."

Fights were easier than this... How was he supposed to be brave for this like Grayfia suggested?

She tilted her head and looked at him with a raise eyebrow. This uncertainty... it was clearly a confidence issue, truly it was. How delightful... a frightened and skittish virgin. "But it is... it's merely one with words instead of with fists."

"I've... I've always been better with my fists rather than words." Issei weakly protested.

There was a shake of head now by the silver haired maid. "The only way anyone can be worse with words is if they couldn't speak. It sounds more like the issue here is that you lack confidence in actually doing things. Almost like someone has trained you to think you can only fail."

"No.. No one trained me to fail." Issei replied, shaking his head. "It's just... What happen if I mess it up? If I presume too much and then get something wrong?"

"And what happens if you mess up in a fight?" She sighed.

"I die." Issei replied. "Well, not like I would die here instead, but..."

"So... you fail. You fall... and then... what happens? You get up, yes?"

"But... Why would Rias still want me if I keep screwing up?" Issei muttered.

"Because of the way you behave. That you're bold, daring, willing to stand up for what you believe in, and for those you care for." Grayfia stated with absolute confidence, it was increasingly clear to her that this was definitely an issue with confidence and fear. After all, in a fight... the worse outcome would be death or such... in a relationship, failure would result in someone disliking him or worse abandoning him.

And that would cut even worse than death or a maiming.

Issei stayed silent. It wasn't that he didn't understand what she was saying, but...

"It can't be that you're afraid to talk to her." She lightly tapped her lips before asking her next question in a mischievous tone of voice. "Or is it because you've been surrounded by the abundance of... oppai that you're too scared to do anything in fear of losing it all?"

Issei blushed bright as Grayfia brought it up. It WAS true he had found himself in plenty of situations with the girls.

"Maybe...?" Issei said, completely unsure.

"Or is it more that you're uncomfortable being so near the girls?" Grayfia said with a light curving of the corner of her lips as she teased him. "Preferring to have girls be your friends and other boys for your... relief?"

"What? No!" Issei immediately denied.

The only time he had felt confused was with Gasper but hell, like there was someone that would dodge that mistake the first time they saw him!

"That's good... I was rather worried about the virtue of that poor boy Gasper." The tittering giggle from the older woman was a delightful sound. "That said, it sounds like you're just not used to being with girls in any other manner than professional or scholastic?"

"Errrr... Pretty much yeah." Issei said. "Didn't change much until I became a Devil."

"And now that you're a devil, you're unsure of how to behave around girls..." She nodded. "In that case, the answer is simple. Practice and trying new things out in a safe environment. Would you agree?"

"Well... Yes?" Issei said, unsure where she was going with this. "But how would that be done?"

"You ask someone who is experienced to help you." There was a beaming smile now by Grayfia. "Someone who doesn't have a stake in your failure, but has a stake in your success."

Issei stared at her answer, but then pondered her idea.

"But... who could I ask...?" He muttered, perhaps more to himself.

She lifted her cup to sip at her tea once more, the very image of calm and tranquility.

Issei thought hard, looking back on many girls he knew. Except when it wasn't a girl that was already close to him, it was someone he couldn't just plain ask this from.

"I... I don't know who I can ask." Issei weakly admitted, dejected.

There was a tsk from Grayfia, one truly could lead a horse to water... but to make it drink, sometimes... one needed to paint a picture as well. "Well... am I not a woman? An older... nee-chan as it were?"

"Eh?" Issei let out, before her words registered in his brain. "Eeeeeeehhh?!"

"But... I can't...! I mean you're married and-!"

A part of Issei's brain had awakened in surprised at the appeal of the idea, only to be immediately imprisoned by the rest of it.

"And getting you the help you need. By talking with you, by practicing things with you like how to behave around women and girls. By getting you used to being near women without panicking." She calmly noted what she was willing to do. "Unless... could you be attracted to me as well? Thinking of me as a beautiful nee-chan who is also untouchable? How adorable."

What! No, he couldn't let that kind of idea stay! Yes, he found her beautiful, but she was married! She had a child!

"T-T-Then..." Issei said, stuttering. "W-Would y-you please help me?"

"Certainly, Issei-kun." The soft clink from the tea cup resting once more on its saucer sounded in the room. "See, you can do this... asking people for help. Reaching out, yes?"

"Y-yes." He replied, incredibly nervous. Now that was a tiem where he could not screw things up. "S-So... What should we do?"

"We'll start with talking and behaviour," She nodded at him before patting on the seat beside her on the sofa. "But for now, I want you to sit beside me."

"Hmmm, okay." Issei said. He wasn't sure about this, but figured he may as well do as she asked.

The light fragrance of flowers hung around her... it was as if he was in a garden near flowers, fragrant but not cloying or overpowering like some girls or women would smell like as if doused in perfume. The proximity of a 10 out of 10 female was something that most boys wouldn't know what to do with. And yet... it was happening to Issei.

Issei found himself not knowing how to act, simply being nervous about how close he was to her.

"Then... what next?" He asked, keeping his hands on his knees.

"You're scared and nervous, yes?" She turned to look at him. "I want you to breath and relax, close your eyes if you need to. The one thing that is obvious is your inexperience, your desire to not mess up, and your fear and nervousness. While there are some who like cherry boys, it's something that is obvious to girls and it's the social equivalent of going about with openings in a fight and saying I don't know what is going on."

"Okay... Okay..." Issei said.

He did as she asked, closing his eyes as he tried to relax his breath. Even if all eh could smell right now was her fragrance.

Whatever idea may have sprung up, he beat it down with his brain and focused on calming down, on getting used to what he was feeling.

There was the sound of her moving about on the sofa, fabric gliding on fabric. "Are you feeling calmer now?"

"Y-yeah." Issei replied.

"I want you to keep your eyes closed and to keep calm." She continued to speak slowly and calmly as if teaching a young child about to do something possibly frightening, even as her delicate hands rested on his, grasping them.

Issei gulped as he felt her take his hands, but did as she asked, keeping his eyes closed.

Apart of him could not help but remark how soft her hands were.

"You're doing good." There was the hint of a nod as she spoke from the way her hair rustled. Grayfia's hands were soft, yes... but they were also warm.

"O-Okay..."

There was only silence as she lifted his hands up in hers before Issei found his hands resting on something very soft and warm...

Issei felt the heat in his cheeks at the touch, wondering where Grayfia put his hands. He did not think it was her shoulders.

Actually, now that he thought about it, shouldn't he be touching cloth?

There was a giggle from her as Issei's fingers into the soft warmth sank slightly when he flexed them. "So, how are you feeling at the moment? Comfortable?"

"Hmmm... Y-yeah." Issei replied, not daring to speak further and the question of cloth leaving his mind.

He figured she knew what she was doing.

"I'm going to move my hands away... and I want you to continue to keep calm, breath in and out... before opening your eyes, okay?" There was a pleased note in her voice as if happy that he wasn't panicking.

"O-Okay." He replied. It wasn't that hard a thing.

He kept breathing even as he felt her hands leave his own.

Then, slowly, he opened his eyes.

His hands rested on a pair of glorious oppai. Bare to the world along with the top of Grayfia's body, she had unbuttoned her blouse and opened it all the way.

Issei's mind flared up in surprise, even as his hands instinctively groped her in reaction. Even if she was asking him to stay calm and he tried his best...!

"G-Grayfia?!" He squeaked out, yet not removing his hands as she was the one to put them here.

She smiled at the groping action. "See... girls are not scary monsters. Well... we are monsters, but so are you... so that doesn't quite work. But we're not scary things that you need to be afraid of."

"B-B-But...!" Issei stuttered as his cool started to break down a bit. "I mean, you're married! I shouldn't be touching you here and-!"

"Well... Issei-kun, I'm helping you get used to the idea that touching a girl is fine." She tilted her head and gave the very image of a nice onee-chan type. If only she hadn't unveiled her bounty and was letting Issei touch them. "And there is nothing wrong with this. More importantly... how are my oppai?"
"Th-They're great." Issei found himself saying, as if he acted on auto-pilot. "They're big yet so soft and warm and..."

Unconsciously, he squeezed some more as he described them.

"That's sweet of you... and now that you've finally touched oppai, are you going to be scared about wanting to touch other oppai?"

Not that he had never touched them before... But he understood what she meant.

"I... I understand..." Issei replied, as he felt himself relax a bit despite the situation.

"If you want, I wouldn't mind letting you feel them some more just so you can get used to this." She nodded at him.

"I-" Issei started to say, before stopping himself. Did they not just go over this?

Did she not already indicate she was okay with it?

With a meek nod, he started to move his hands around on her breasts, getting a good feel for them.

Squeezing them a bit and taking care to softly touch her nipples as his fingertips passed them.

There was a shiver at the way he felt her breasts, slow and hesitant... it reminded her of the way Sirzechs had been that first time. The blush that formed on her face was perfectly natural even as he nipples slowly stiffened under his touch.

Issei's mind seemed lost in his own world as he focused on his 'task'. The changes in her nipples was noticed as his fingers slowly played with them, burning the sensation of the touch in his head.

There was a gentle stroking of the back of his head as she slowly pushed his head down to rest on her breasts.

Issei was shaken awake by the gesture, but did not dare speak given where his mouth was.

"So... I trust, you're feeling much more confident about oppai?"

"Y-yeah..." Issei dared himself to say, even as he felt her skin on his lips.

"And when you see Rias, you are going to be able to ask her to go on a date with you, right?"

"Y-y-yes... I believe." Issei stuttered.

"You don't sound confident... or is it because you're going to be thinking of this poor onee-chan when you ask Rias out?" There was a sly amused tone in Grayfia's voice.

W"ha-? N-No!" Issei exclaimed, shocked by the idea.

She nodded happily. "That's good, because I would be said if you were going to be thinking of me when you're with Rias, flattering as that would be.

Issei did not answer as he had nothing to say to that. But he had to wonder how long Grayfia would hold his head where it was.

"But since you're still uncertain... we might need to go a step further." She looked carefully at him. "Are you willing to fight for Rias, to be brave and do as I tell you and go the next step?"

"Y-yes!" he said, barely avoiding the note of confusion he had. What kind of next step was she talking about?

Especially after just now?!

She lifted his head with a finger under his chin, before guiding him to stand up with her. "I'm feeling a touch warm... why don't you help me out of this stuffy dress?"

Her top was open and her bra, nowhere in sight. Despite already being partially undressed, Issei felt his cheeks turn redder.

Just how red would he become today?

"Well... Issei-kun? I'm waiting~"

His words died in his throat.

Slowly, carefully, his hands moved on her maid dress, pulling back the fabric on her shoulders.

He undid the last few buttons that were over her stomach, before continuing to pull the dress down.

There was an approving smile from Grayfia as he did as instructed even as her dress pooled around her feet. "That's good, Issei-kun."

She turned about before him, modeling her best features... namely her breasts and ass.

Issei could only stare transfixed as Grayfia was doing all this, almost fully bare before him.

His hands were twitching as he reined in his nerves.

With only a lacey pair of underwear and stockings on, Grayfia was very much the image of an attractive older woman, the hint of darkness on front of her panties certainly teased at Issei's imagination.

Despite his best efforts, Issei's pants started to become a bit uncomfortable as his dick hardened under the show.

How could he not after all? Even married, Grayfia was a great older beauty currently showing off to him.

Once more, she smiled and grasped his hand before she stepped free of her dress... pulling him along as she stepped over to a padded table, that was closer to a bed for a single person to lie on.

Issei could only dumbly follow along, not trusting his voice at this time.

With a grace that came from her countless experience on the battlefield, she walked and lifted herself on the padded table to sit in front of Issei. "So, Issei-kun... tell me, beyond oppai, what do you like or want to do with girls?"

"I... I want to touch them all over as well." He admitted, his voice a bit strained by effort.

He did not feel it was a great idea to say how many sex fantasies he had.

"Touch them and possibly... more, huh? How perfectly natural." She nodded.

The slight nod was enough to introduce a delightful joggle to her breasts.

Issei gulped as he saw the jiggle.

Grayfia, as great a beauty she was, was never someone he considered anything happening with because she was married and he wasn't that kind of man. Today, however, his mind had already been blown several times.

Still, Issei was doomed to disappointment as she turned about before lying down on the table, hiding the oppai from him. At least, before she spoke once more. "Do you know, as a maid, my shoulders get very stiff doing the things I do... why don't you help this poor little onee-chan out and massage her back?"

Back. Yeah, he could do that. After everything else that already happened, why would this be an issue?

He moved to her side, a bit nervous, but he had no issue getting his hands on her shoulders.

He started from there, what he saw as the safest place right now, as he start to carefully massage her despite no prior experience.

There was a soft sigh of delight from Grayfia at the touches down her back as Issei's hands relaxed her muscles.

As Grayfia started to relax, Issei started to move his hands down bit by bit. It was honestly a tad easier than before to touch there, so he wanted to do this perfectly well.

His fingers worked well under concentration as they did their work on her surprisingly soft back.

The soft sigh was one that could be heard by Issei, but it was a good thing as it showed how relaxed Grayfia was becoming even more so than her muscles beneath his fingers. It was also clear that she likely had her eyes closed.

Further and further down Issei's hands were. Now, they were at her waist, at the edge of her rear.

There was a soft pop that sounded all the louder in the silence as he stretched out the small of her back accompanied by a soft sigh of relief. Goodness, she had been tense, hadn't she?

Issei's hands returned a bit up, even as his eyes kept eyeing her rear.

He shouldn't. He really shouldn't. But...

Didn't she tell him to be more daring? Taught him to take initiative? That not everything would turn wrong by one mistake?

With a gulp, one hand left her back even as the other continued...

And he put it on her panties-clad rear, experimentally squeezing softly as if he tried to massage it as well.

There was a gasp of surprise... but it faded into silence as he continued to massage it. No recriminations, no angry shouting... just a simple acceptance.

With nothing else happening, Issei released the breath he did not know he held and went on.

While still massaging her back with one hand, the other caressed her rear, enjoying the feeling of it over her panties.

After a while, his other hand joined it as he found himself only massaging her butt.

That soft delightful bubble butt was a thing of beauty. It was something that Issei would have to give 10 out of 10 if he saw it on a school girl, on Grayfia, it was one of the things that made her physically perfect in appearance. The soft of mmmmh of pleasure from her as he worked on the butt was a sign of how well he was doing. "Issei-kun, why don't you remove that for me?"

The 'that' was clearly her panties.

This time, there was no protest. Nor question on if she was sure.

With a daring he certainly did not have before all this, he took them and pulled them down, taking them off her.

The panties were warm in his hands and it held that same flowery fragrance and felt slightly moist in his hands.

With delicate attention, he set them aside properly as he returned to his previous task.

Her rear felt even better now that it was bare.

The lack of panties certainly made his task easier...

Still, now that her back was all done, he had massaged her rear and there was little point in massaging stockings-clad legs...

He felt more of his newfound daring come up.

"G-Grayfia, do you want your front massaged as well?" Issei asked.

"Issei-kun. I would be happy to... but I want you to ask again... without stammering on my name. Be bold, be certain, don't doubt yourself or let your voice be caught, hmmm?" There was a soft reply from her, not a dismissal or disagreement.

"A-Alright." He answered, before clearing his throat. "Grayfia... Please turn around so I can do your front as well."

"Much better." She nodded in approval and did as requested, twisting over to lie on her back, her arms moving her about before resting once more on the padded table. And Issei was treated to a sight that had to be a reward from the heavens and for listening to Grayfia.

Absolute perfection.

Large oppai, perfectly pale skin that had not a hint of blemish, and as his sight moved down... Issei finally saw it, the thing that he and his friends had speculated about, had seen censored on AVs and adult magazines. Pinkness without a single trace of hair.

He had seen Rias naked before. had seen others naked as well. But none could compare to the sensual appeal Grayfia presented.

After admiring for a moment, he started his work once more. This time, he began with her stomach, a place he had yet to touch.

Being a bit softer due to the area, he also let his hands drift to her waist to massage and caress them.

There was a happy mmmmmh as Issei worked on her stomach.

At the same speed as before, Issei made his way up. The goal was clear this time: her glorious breasts.

He had little hesitation this time. When he reached them, he did not back off or ask before grabbing them, massaging and enjoying them at the same time.

Her nipples hardened beneath his ministrations and there was a soft moan of pleasure, or was that a gasp of pleasure as she blushed.

As he was thanking the Oppai Goddess, the sound of pleasure registered in his brain.

A sound he never ever expected he would get to hear from her.

He wanted to hear it more. He worked on her breasts more carefully, making sure to properly touch her nipples as well.

There was another gasp of pleasure as Issei found that Grayfia was sensitive there.

As Issei found himself enjoying the sounds she made, a smell reached his nose.

Even as his hands toyed with her nipples, now clearly seeking to give her pleasure and the pretense of massage abandoned, his eyes were drawn to the area between her legs.

There was a soft pant of need.

The smell... the moans... the erection trying to rip his pants...

Issei was having trouble thinking straight. He wondered how she was feeling. What she would feel if eh did more.

If wondered what she would... No, he WANTED to see how she would be like under an orgasm.

One hand left her breasts, drawn to a magnet to her lower body.

With only a second to think it over, it dived down, starting to caress and play with her lower lips.

The ahhhh of need was clear as was the trilling note of pleasure. Her lower lips were warm, very soft... and sticky?

She was wet. That fact rang in his mind loud and clear.

Without restriction, he started to stroke her harder, even as his other hand did its best to play with her breasts.

He wanted her moaning, gasping, arching her back under the pleasure...

He wanted her to come.

There was a shiver of pleasure as she moaned softly from his strokes. "Soo... slower... not so... hard... Issei-kun."

He barely registered her words as he slowed down a bit, at her request. But despite doing so, he added something else. Even as he kept his eyes on her, he lowered his head on her free breast, taking it with his mouth and playing with her nipple. Meanwhile, his hands between her legs were searching for that mythical spot. The one that would show him what he wanted.

There was a silent pause as she froze for a moment, pleasure running riot within her body, her nerves aflame with lust and need and seizing control of the thoughts in her cunning mind. Animal pleasure ruled her in the here and now.

The only physical sign of such was the simple pause in motion, that mindless wide eyed look on her face with its fierce blush as her tongue lolled about. The japanese called it the ahegao look and the english called it the fucked silly look.

"Ahhhh! ahhhhhh!" The squirting of her liquid pleasure into his hand as she unfroze, her back arching as she cried out her pleasure... that was all the evidence that Issei needed to confirm that she had reached the clouds and rains.

He marvelled at the sight of her in such a moment, knowing he was the cause of it.

His pants strained, he did not really see a reason to keep his hard-on confined a moment longer. In a few seconds, his cock was out, erect and pointed in Grayfia's direction.

Slowly, her animalistic hind brain released its control of her higher mind as the pleasure ebbed, swirling back down to that pearl that guarded her 'treasure'. There was soft pants from her as she relaxed. With the return of her conscious thought, there was a fierce blush on her face. "Ahhh... Issei-kun."

"Grayfia..." Issei said in turn. His breathing had turned a bit rough, pent-up feelings getting to him.

He took a single step closer to her, erection shaking in the move.

"Well... it appears... that your youthful vigor is certainly something to behold." Her eyes had a lazy look of pleasure as she gestured with one hand in the universal come hither manner. "Truly, I envy Rias."

"Is that going to be the next lesson then?" Issei panted, lust in his voice. "There's no need to feel envious then..."

There was a look of surprise on Grayfia's face as she panted and reason slowly returned to her. It was clear that the boy was growing bold, and yet... to cut him down now... would it introduce more neurotic trauma and undo her work til now? Still, would she not lose control if he continued on while she was in such a state. "Such... vigor would normally be rewarded. But, Issei-kun... it might not be a good thing to be too forward."

Issei, only half listening, was now climbing on the table over her. He parted her legs in anticipation of what was to come.

"Well, that's why I'm practicing, no?" Issei said, eyes fixed on Grayfia's treasure.

He readied himself, his cock coming ever closer as he got in position.

"Issei-kun!" There was a choked note in her voice as she looked at the way he was simply focused on what lay between her legs.

"Don't worry, I'll try my best." Issei said, ready.

He leaned down to take her lips, eager to kiss her as his hips went down, entering her and filling her up.

She could only squeal into the kiss as she felt a rather surprising wide cock push its way into her wet pussy, gliding inwards without any resistance. Her lubricated inner walls accommodating him, sucking his hardness ever deeper in.

Against her thoughts, she could feel the enhanced heat spiralling out from her pussy and up her belly. Her legs moved without thought as she encircled his waist with them, locking him in against her.

Issei's joy soared as Grayfia easily accepted him and locked her legs around him.

He started to move as his kiss ended, putting what he had in his hips as a hand went to caress one of Grayfia's breasts.

There was a gasp of need as the kiss ended and Grayfia proved that she was as sensitive in her breasts as Issei had perhaps speculated in his dreams.

Driven by lust and need, Issei's thrust increased in strength as he sought to go as far as he could into her. So much, her breasts bounced each time.

"Grayfia...! Grayfia...!" Issei was letting out, panting.

The silver haired devil could only gasp in need as she slowly matched Issei's rhythm, pushing out and pulling back in his cock with her body motions. This was done on instinctive need than any conscious thought. "Issei-kun!!!!"

Hearing her call out his name in pleasure, on top of everything else, was like a trigger for him.

He slammed down and came, lust driving him to fill her womb with as much of his seed as he could

At the warm seed spilling into her, Grayfia found herself awash in pleasure once more. Her pussy had been made sensitive by the climax earlier reacted as could be expected in the face of Issei's bold plunge deep into her with her inner walls twitching as she cummed in return. Her legs locked into position, keeping the young man trapped against her as his seed splurged into her womb while her arms ringed his neck and held him against her.

For satisfaction, desire, lust or all those three, Issei took her lips once more. He sought to claim her own mouth just like he claimed her lower lips.

There was no more shock or surprise from Grayfia, instead... she leaned into the kiss and replied back with passion and pleasure, her tongue slipping into his mouth, assaulting his lips and making its way pass them.

They spent time making out like this as minutes tickled. But time did pass as Issei could feel himself harden once more.

There was so much he wanted to do, after holding himself back for so long.

"Grayfia..." He muttered, pulling his head away. "I want... I want your oppai."

He eyed the couch, seeing it as the best place for it.

There was a warm smile directed at Issei by Grayfia as she looked at him kindly as her hands released his neck before following his gaze at the couch. "My... oppai? I don't know Issei-kun... is this onee-chan's oppai good enough for you?"

"Of course they are!" Issei claimed. "They're magnificent!"

He got up from the table, before also pulling Grayfia up. Walking to the couch, he sat down on it, erection standing up once more.

And awaiting.

She smiled and slipped off the padded table before she started to strut towards him. Her grace giving her motions a little something extra, hint of white from her lower lips a very good sign of Issei's cherry boy status being lost. The light sheen of perspiration on her body simply made Grayfia more beautiful.

In a single smooth motion, she knelt between his legs, the sway and jiggle of her breasts hypnotic.

Issei smiled in approval even as his legs got closer around her. Holding her there between his legs.

"Issei-kun... are you ready for this onee-chan's assault?" The smile as she breathed out her words, her warm breath blowing across his hardness was almost enough to distract the young man from her breasts as they sway delightfully with her motions... almost.

Issei gulped, shivering in anticipation. But he still gave a small nod.

She nodded at him, her lazy smile a thing to behold as she slid forwards with her breasts cupped by her hands.... and warm softness surrounded his maleness. A stark difference between sex with a pussy.

heaven. He was in Oppai Heaven. There was no other way to describe it.

He relaxed as Grayfia took him in her breasts, as he settled his hands on her shoulders to urge her to move.

Slow gentle movements saw his dick engulfed by soft heavens... the scent of her perspiration mixed with his seed a heady bouquet.

It was Grayfia who set the pace for her back and forth rocking motion. A sense of control lost here... and yet, it was meant for his pleasure.

Issei groaned as he saw one of his dream finally happen. And with her of all people.

A hand gently flowed from her shoulder to her breast, softly groping it as she moved them.

There was a thrusting motion, and Issei found the head of his 'little brother' peeking from the top of Grayfia's breasts... to be met by a warm breath from said silver haired devil.

"Well, now... what do we have here? A valiant devil whose managed to escape heaven..."

Issei could only stare, as his voice seemed taken.

What she going to... Was she really about to do THAT?

She leaned forwards, dipping her head... her moist warm breath blowing on the head of 'little Issei' before her mouth surrounded its started to suckle it as her breasts were guided by her hands so that they continued to move against his.

Issei couldn't help himself as he groaned, his hips moving a bit.

The pressure was building under her care.

Here, it is clear that Grayfia was truly experienced in the ways of pleasure.... at least compared to Issei's fevered imaginations in the quietness of his bedroom.... her mouth's ministrations of his dick, the way she licked the underside of 'little Issei'... even as her hands cupped her breasts and ensured that just below her mouth was the soft heavens that were her Oppai.

Issei, under all this, could only do one thing.

He came, hard, firing once more all he could. As much as he could. As if he wanted to mark her, to claim her for himself.

Her and her oppai.

Despite all of his rapid firing... not a single drop made it out of her mouth. His seed was captured by the lips of the silver haired devil.

"Grayfia...!" Issei groaned, calling her name once more as she was set on apparently swallowing everything he sent.

An eternity later, Issei could feel his dick being released as every single drop of his seed was devoured as they left him... at least, it was released after it was cleaned by her tongue. It was slightly moist... but clean.

That it went beyond his fantasies, taking and swallowing everything...

As if he had Boosted himself, he took no time to get hard again, as he pushed her down on the floor.

"I... I must practice as much as I can, right?" He asked.

"Oh ho! I see you've lost all your confidence issues." There was an amused smile now from Grayfia, as of a big sister who was proud of the accomplishments of a little brother who finally worked out how to do things.

"Yeah... Thank you Grayfia." He said, even as his dick poked her thigh.

Even as he went down on her once more, Issei made sure to do the best he could, both for himself and for her.

- - -

Quite some time later.... Grayfia sighed with delight, very sore and worn out in a way that combat wouldn't have managed to do to her. It was as if she had gone up against an army of devils and angels together by herself. Issei-kun, she wouldn't call him boy now... was very much a man with endless stamina.

Issei, who was laying on top of her, finally came to his senses.

While the beauty under him was a great sight to his eyes, his mind finally remembered just who she was.

As well as everything he did with her.

"G-Grayfia, I..." He attempted to say, voice trembling as he tried to push himself up.

"Hmmm? I would think after all that we've done, you would call me Grayfia-sensei, Grayfia-neechan or perhaps Grayfia-sama." There was a gentle and lazy smile from the devil beneath Issei.

"But... But Grayfia, what I did! I went too far, I shouldn't have..."

Issei was obviously starting to panic. What had he done, having sex with a married woman?!

There was a shake of head by Grayfia. "And I didn't mind it. The point of this was to help you."

"Even so... How am I supposed to face Rias now? And others?" He said. He was not panicking, but was still shaken.

"You would face them as you always have." A hand slipped down between his legs to pat a very soft and worn out dick, a soft reassuring?!? pat as if a child was being given head pats by a big sister. "With confidence and boldness."

"And... And it's alright like this?" He asked. "Just... going like this as if it was all okay?"

"Yes, it will be." She nodded solemnly and calmly in response. "Because it'll be a secret... just between the two of us."

"The important thing is that you feel better about approaching girls. And most importantly... we can practice this some more until you feel absolutely confident about things."

Issei gulped as he took in her words.

Somehow, his first step in his harem had been to have sex with the silver-haired beauty and come out with no consequence for it.

And yet, his nerves calmed even as she spoke of doing it again...

Somehow, he truly believed things were about to look up for him.

- - - Owari? - - -
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Instructing the Bold Dragon