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...