Issei shifted in his sleep. He was still naked from last night.
“Let’s go over this one more time,” Rias said. The four of them were at the edge of the bed, all dressed in panties and semi-translucent nightgowns. “I had his first kiss.”
“And his first tongue-kiss,” Akeno added.
“Also his first boob-touch, boob-suck and boob-see,” Xenovia said.
“Raynare was the first pair of breasts he saw,” Rias said. “But let’s not go in that direction. I thought we agreed I could have all his first times?”
“All of them?” Akeno said. “You also had his first blowjob and you were the first one to taste his sperm, and the first girl he fingered.”
“But you were the first one to suck on his fingers,” Rias said.
“That hardly counts.”
“Xenovia had the first facial, and she gave him a boob-job, and she sucked him off more than all of us combined,” Buchou insisted.
“I feel like Asia and I are really getting the short end of the stick here,” Akeno said.
“Fine then,” Rias said. “Both of you can have one of his first times, but I’ll be the one to take his actual virginity.”
“Uhm,” Asia finally spoke. “Does Ise-kun have any first times left? If Rias-oneesama is already going to take his virginity.”
“Ara, ara, Asia,” Akeno kirred. “I thought Kiryuu had thought you some things.”
“But,” Asia insisted. “We’ve already used our breasts and our mouths on him, so what else is there? Except, you know, real sex.”
“Well I have something in mind,” Rias said. “Wait here.”
She crawled over the bed to Ise. The Red Ruin Princess slid down the spaghetti straps of her top so her marvelous breasts were exposed. Considering she wanted to wake the Oppai Dragon, it only seemed suitable she gave him something to look at, or maybe play with. She blushed a bit at the thought.
The others watched as she slowly removed the covers from Ise until his chest was visible. Just a bit further and his cock would pop out, but she had to restrain herself a bit, first Asia and Akeno would get what they deserved, and then, she would once again strip down for Ise and ask, no, beg him to take her virginity, only this time, no one would interrupt them.
But first things first.
She got on top of him, her knees on either side of his hips and then bend down. Her breasts were hanging merely inches away from his chest.
She moved her lips closer to his, but not close enough to touch, only enough to make him feel her warm breath.
Then, she gave him a kiss. Their lips touched very lightly and then left again. She continued to trace featherlight kisses across his throat and collarbone. Her breasts moved closer until her nipples, which were hardening quickly, could brush against his toned chest.
Ise stirred in his sleep, but didn’t wake up.
She continued to rub her breasts against him, her nipples were rock-hard by now. Her lips moved back up, across the stubble on his chin to nibble on his earlobe.
Now, he woke up.
“Morning,” she said, very softly. She smiled and bit her lip.
“Morning,” Ise replied. His hand touched her lower back and then slid down inside her panties to squeeze her ass.
“Oh,” Rias let out a playful moan. “Already in the mood, are we?”
“Well,” his other hand cupped one of her breasts. “If a horny girl wakes me up like that.”
“It’s your fault, I didn’t cum last night, so I’m still horny.”
“You had to be punished,” Ise said. “Besides, I think you’re permanently horny when I’m nearby.”
“Maybe,” she said. “In any case, I have a request for you.”
She leaned close and whispered something in his ear.
“Oh.” He looked to the side. Three girls were kneeling on the edge of the bed. They smiled sheepishly, especially Asia. Akeno had apparently gotten quite horny from watching them, since her nipples protruded through her top. Her hand was stroking her thighs.
“Are you okay with that?” Ise turned back to Rias. “I thought you wanted all of my first times.”
“We’ve come to an agreement,” she said. “You don’t mind if we watch, right?”
“No,” he said. Then, he leaned closer. “If you’re a good girl, I’ll do you next,” he whispered.
She turned beet-red. “You don’t have to do that,” she insisted. “We should be the ones taking care off you.”
“I want to,” he simply said. “Now then, shall we begin?”
She nodded and got off him.
“Come on, Asia,” Xenovia said. “Take this off.”
Asia weakly protested, but Akeno raised her hands and Xenovia pulled the nightgown over her head. She tried to hide her breasts, but the swordswoman pulled her hands aside. “Don’t hide your body. Your breasts, and everything else, belongs to the Harem King now. Unless you don’t want to be part of his harem?”
“I do,” she quickly said. “I don’t want to leave Issei-kun.”
“Well then, hands behind your back and pull your chest out, let him see your body. Let him touch you however he wishes.”
She weakly nodded and folded her hands behind her back. The innocent girl pushed her chest out. “I hope my breasts please you… uhm, Sir. I know they are a bit small, but I’ll do my best to please you in any way you want.”
“Wow,” Akeno mumbled. “Kiryuu must have been training her better than we thought.”
Issei took one of her breasts in his hand and squeezed her nipple. As he tugged and twisted her nipple it got hard and she let out wordless moans. Her face was flushed and she was breathing hard, but her hands remained behind her back.
“Asia seems to like that,” Rias said.
The blonde girl nodded fervently.
“Let’s get her on her back,” Issei said.
The girls guided Asia on her back. Xenovia pulled her arms above her head and held them there.
Ise knelt between her legs and took hold of her panties. He slowly pulled them down. Asia’s face turned red in embarrassment.
“Such a lucky girl,” Akeno said, she licked her lips.
He was acutely aware that the others were watching him as he slowly spread her legs.
“Ise-kun, what are you-”
Her words mingled into a loud moan. He had only softly brushed past her clit, but she was already leaking on the covers.
He knew she never orgasmed on her own, so this had made her very sensitive.
With the others still watching, Issei brought his head between her legs and licked her pussy.
He heard her gasp. “Don’t Ise-kun, it’s dirty,” she pleaded. Her hands tried to stop him, but Xenovia kept them pinned above her head.
“Just enjoy yourself,” Xenovia said. “Or would you prefer to switch with one of us? We’re ready to go any time.”
“No,” she yelled. Then, she blushed heavily.
“That’s what I thought. Now just enjoy whatever Ise-kun plans to do with you.”
She nodded weakly.
Once again, he went down on her and brought his face to her lower lips. His tongue prodded at her opening. Ise briefly wondered if the sweet taste was unique to Asia. Maybe Rias would taste differently. He was determined to find out later.
His tongue flicked past her clit and she shivered. He smiled. Asia was melting beneath his touch.
His expert tongue continued to lick her out with some occasional nudges from Ddraig. He would never admit it, but it was obvious Ddraig knew more about oral sex than he let on. Asia was panting by now and every minute, she was leaking more and more fluids on the bed.
While he licked her clit, he brought his fingers close and pushed the middle one in her. It went in smoothly given her copious amount of natural lubrication.
Asia gasped and he felt her muscles spasm around his finger.
Ise pushed a second digit inside and started fingering her while still licking her clit. She was thrashing by now, luckily, Xenovia held her down.
“I think Asia wants to cum,” Rias said.
“No,” the blonde girl quickly said. “Please, no.”
“Why not?” Issei asked, he pushed his fingers in extra deep, hitting her G-spot.
“I don’t want to… it’s dirty.”
“You mean you’re a squirter?”
She turned bright red at that.
“Please don’t make me cum,” she insisted.
“Nothing about you is dirty, Asia-chan. Your girl-cum is are already all over the bed, so I don’t mind if you add some more.”
“We should be the ones making you cum, not the other way around,” she pleaded.
“But you said you’d do anything to please me, and it pleases me to watch you cum for me.”
“Ise-kun, please, don’t watch me, it’s embarrassing. I’m not ready.”
He had seen her cum before, but that time, they had been alone. And she had been incredibly desperate, having gone for weeks without an orgasm while masturbating every day, fantasising about Ise, as per Kiryuu’s instructions. She had probably resumed that habit, but it had only been a little over a week since then so she wasn’t desperate enough to let all of them see how she squirted over Ise’s face.
“Release her please,” Ise said.
Xenovia hesitantly let Asia’s hands go.
Ise pulled her upright and then whispered something in her ear.
She had a shocked look and looked even more embarrassed (if such a thing were possible).
“B-But-” she sputtered.
“That wasn’t a question,” Ise said. He laid down on his back.
She nodded. “I understand.”
Asia put her knees on either side of his head and then bend over. They were in the 69-position now, with Asia on top. Her pussy hovered above his face.
She hesitated for a second, blushing heavily, but then, she opened her mouth wide and took him in. She had never done this before, although of course, it would be expected of her as part of Ise’s harem. He tasted slightly salty, probably the precum leaking from the tip.
She really should have asked Kiryuu how to do this
“Xenovia,” Ise called. He didn’t have to explain.
Xenovia positioned herself and started slowly licking his balls. Given that Asia was much closer to an orgasm than him, he would need to cheat a bit.
Asia’s sucking was clumsy and without much rhythm. He reminded himself to let Xenovia show her some tricks later.
But first things first.
Ise raised his head and licked her pussy. She tried pulling away, but he grabbed her butt with both hands and forced her to stay at that height.
She was quickly leaking all over his face.
It wasn’t long before she started twitching. He was getting close as well. Xenovia was an expert and while Asia’s movements were clumsy, it somehow turned him on even more. This innocent sister was sucking him off in such a lewd position. He felt a familiar tugging sensation.
“Hang on, Asia,” he warned her. Then, he wrapped his leg around her face and forced her down. She made a gagging sound which pushed him over the edge.
He felt her struggle as he came in her mouth, but at the same time, her body started twitching and a geyser of fluids erupted from her pussy.
When he was done cumming, he released her head. She took his cock out and started coughing violently.
“I-I’m sorry, Ise-san,” she managed to say. “This isn’t a proper way to end a blowjob. I’ll keep your cum in my mouth next time, I promise.”
“You’ve done well,” Ise said, he patted her head. He briefly noticed Xenovia was licking up the spilled cum.
She smiled weakly. “Thank you.”
“Ise-kun.” Rias came closer to him. “That was really hot.”
The redhead kissed him. Her tongue traced his lips. “Asia tastes good,” Rias commented before resuming her kiss.
“You had fun as well, didn’t you?” Xenovia said.
“Uhm, a bit,” Akeno admitted. She removed her fingers from her gushing pussy.
“Hey, Issei-kun,” she said. “Come see me this afternoon. I have something special planned for you.”
Hey, Ddraig. What does she mean by that?
[How am I supposed to know?]
“Don’t worry, Ise,” Rias said. “It’ll be fun. Now, are we going to take a shower?”
[So when were you planning to take her?]
Uhm, I don’t know.
“Don’t worry, Ise-kun,” Rias said as she took his hand. “When you’re done with Akeno-san, I’m all yours. Until then, please be satisfied with my mouth and hands.”
“What about your breasts?” Ise smirked. He touched her chest.
“What are you gonna do with them, pervert?” She asked playfully.
“Well, now that you ask…”