Disclaimer: Highschool DxD, To Love-Ru and their characters do not belong to me.
Hello, this is a new prompt commission, requested by an anonymous commissioner, hope you like it.
X – X – X
In Sainan, the girls hate four boys in particular.
The crazy falls boy Yuuki Rito who, being so clumsy, always fell on top of the girls, in very compromising positions.
On the other hand, the perverted trio, the apprentices of the idiot director, who talk all day about breasts and butts without any shame, with the leader, Hyoudou Issei, being the most hated and loved guy in the academy, a strange contradiction.
"Issei-senpai, what happened now?" Haruna asked the older student in the infirmary, bandaging his knuckles.
"The usual, Haruna-chan." Issei grimaced. "Some idiots tried to take advantage of Saki-sama and Rin-san."
Issei may have been a hopeless pervert, but he always protected the girls at the school from even worse men, which caused conflicting feelings among the female student body.
Hating him, or respecting him, was always a dilemma.
Not for Haruna though, who knew the boy since childhood and knew that he was a really good person.
Even his perversion was accepted by the blue-haired cutie; considering the boy she liked, she couldn't judge the Hyoudou.
And regarding Rito...
"Today Yuuki-kun fell in front of me." Haruna excitedly told Issei. "I helped him get up and we walked to school together."
"You should confess." Issei told her immediately. "You've been doing nothing but walking together for a year, it's kinda lame."
"It's not that easy." The Sairenji shook her head. "When I try to have a serious moment with him…" A sweatdrop fell from her forehead.
"He falls, touches your chest or legs, and you hit him." Issei laughed a little.
"Yes." The girl blushed.
" I don't know what you could do." The Hyoudou scratched his cheek. "Rito is a good guy, but I don't know if he likes you." The student massaged his knuckles. "Sure, he falls with you and blushes, but he does that with all the other girls he touches with his 'accidental' falls." Issei lowered his head and muttered. "Damn lucky bastard."
Sainan's red dragon would kill to have the Yuuki's ability.
"You say I don't have a chance?" Haruna became depressed.
"No, not at all." Issei nervously said, not wanting to see his friend cry. "I'm just saying you should be the one to take the initiative."
"Should I do the same you did with Kujou-san?" The Sairenji chuckled as she remembered Issei's confession to the knight of Sainan's queen.
"Don't..." Issei shivered, feeling chills. "Don't talk about that, you're gonna summon her." The boy was still scared of what Rin did to him that time.
"But you have more experience in relationships than I do." Haruna cheered up. "Then you can help me."
"Yes, I think so." Issei didn't want to discourage the blue-haired female.
"Help me then, Issei-san!" Haruna made a request.
"Ok..." The boy didn't know what he was getting into. "Perhaps I could help you how to satisfy a man, so that you can use it with Rito." Issei joked, as he always did with Haruna.
"Okay." Haruna this time didn't follow the routine. "Help me learn how to please a man, Issei-san."
"What did you say?"
"Help me have more experience." Haruna looked at him, determined. "I promise to learn well." The cute girl promised.
"You know I was joking, right?" Issei asked her.
"..."
"..."
"..." Haruna began to blush and stagger.
"Haruna!"
The red dragon lunged forward to grab the girl before she fainted.
X - X - X
The Hyoudou took Haruna to her house, where miraculously the girl's sister was missing, something Issei celebrated, before her friend woke up.
And he would like to keep his promise, since he already promised to help.
Even so…
"Are you sure you want to do this?" Issei asked nervously.
"I already promised that I would learn to be a more mature woman." Haruna blushed. "And I trust you, Issei..."
"This goes beyond trusting." The brow-haired male pointed to their clothes.
Or lack thereof.
Issei was only dressed in his boxers, letting the shy girl see the muscular body of the school's strongest pervert.
In turn, Issei could notice how his friend matured physically, not reaching the sensuality of her older sister, but being sexy and cute at the same time.
Wearing modest white underwear, Haruna's modest but shapely Oppai were an arm's length away from the Hyoudou.
The white panties stuck to the turned, shapely hips of the Sairenji, who blushed as she noticed the hunger in Issei's gaze.
"Kya..." The blue-haired woman covered her private parts, before remembering her promise. "Issei-kun..."
Issei watched excitedly, his cock almost overflowing from the boxer, as the girl raised her arms as if she wanted to hug him, her face red as a tomato.
"Are you sure?" Issei asked again, this time getting on top of the girl.
"Yes..." Haruna smiled at him. "Just... be gentle."
Issei pulled down his boxers, causing the blue-haired to blush when she felt his cock against her thigh, before she gasped when her friend touched her womanhood, massaging her vagina over her panties.
"Ahhh..." The Sairenji couldn't help but moan.
The red dragon massaged his friend's pussy for a few seconds, breathing heavily, before moving her panties to the side and being able to see Haruna's pink cunt, the man really excited by the view.
"Kya..." The bluenette blushed like a tomato. "It's big..."
Issei grinned with pride when she saw Haruna admiring his cock, before he positioned himself on top of her, grabbing his phallus and lining it up with his friend's pussy, looking at her and asking permission to continue.
Haruna nodded shyly to Issei's expression, before biting her lip as the Hyoudou pressed his cock against her pussy, before starting to moan loudly as the brow-haired male began to penetrate her.
"Fuck..." Issei cursed, now grabbing Haruna's hips. "You're really tight."
The Hyoudou kept moving forward, his cock going deeper and deeper into Haruna, until it hit a barrier.
Haruna only saw him, her face with a permanent blush, before sharpening her gaze and hugging the Hyoudou, causing him to take away her virginity, Issei's cock entering the depths of her tight pussy.
"Ahhh!" She screamed in Issei's ear. "It hurts!"
Small tears came from the girl's blue eyes, while Issei tried to reassure her, trying not to cum because of how tight Haruna's pussy felt around his dick.
"Quiet..." Issei whispered. "Take your time, let's continue when you feel comfortable."
Haruna just nodded in tears, trying to regulate her breaths while Issei kissed her cheeks, waiting for the bluenette to get used to the cock inside her.
"Fuck. " Issei closed his eyes while cursing. "I want to fuck her."
The Hyoudou always knew that his friend was a cute girl, but having her under him, feeling the little Oppai of the girl against his chest, and his cock inside her, only made him notice that little Haruna was not so little anymore.
"Sta-start moving, Issei-kun." Haruna told him faintly.
The red dragon hid his face in the neck of the cute girl, hiding his perverted smile, before starting to move his hips at a slow pace.
"Ahhh..." Haruna groaned, closing her eyes. "It feels weird..."
Issei rammed into the girl once, causing her to exclaim in pain and a little of pleasure, the guy pausing for Haruna to get used to the feeling of all of his cock inside her, before moving his hips back.
"You're so tight..." Issei said, kissing her neck, finding a taste for the action. "I have a hard time moving..."
Haruna's pussy has been the tightest pussy the red dragon has ever felt, but she asked him for help, and as the good friend he was, the Hyoudou was going to help Haruna become a more experienced woman.
Issei pulled out half of his cock, the girl grimacing at the absence of her pussy being filled, before he rammed in a little harder than usual, going balls deeps into Haruna and causing her body to move across the bed.
Haruna moaned in his friend's ear, now feeling more pleasure than pain, which was noticed by the teenager, who pulled his cock halfway and then rammed Haruna again.
"Ohhh..." The girl moaned again, hugging her friend. "Issei-kun..."
The girl never expected to have her dear friend on top of her, moving against her womanhood and sticking his thick dick inside her, taking away her virginity, something she always thought she would lose with another brunette.
But at that moment, Haruna didn't think of anything else... than Issei making her feel pleasure.
Issei breathed heavily on the Sairenji's neck, and swayed against the girl, being careful to avoid hurting her, but increasing the speed little by little, the girl's moans complementing the pleasure caused by Haruna's vaginal walls around his shaft.
"Haruna-chan..." Issei raised his head to kiss the girl's cheek. "You feel so good..."
"That's good." The girl smiled gently, feeling butterflies in her stomach. "You feel great too." That made Issei chuckle.
Issei forgot why he took his schoolmate's virginity, and lashed out harder, drawing a shriek from the teenager, which was followed by moans of pleasure, the red dragon pulling his cock in and out of his friend.
Issei kept moving his hips back and forth, his thrusts getting faster as Haruna relaxed beneath him, the girl moaning in pleasure and hugging him, prompting him to keep going.
"Haruna, I'm going to cum." The boy whispered to her, kissing her cheek and the corner of her lips. "Oh, sorry about that." Issei remembered that Haruna liked another boy.
The blue-haired girl surprised him with a kiss, or not actually a kiss, but a slight peck to the lips that looked more like a touch, the girl blushing like a tomato, before the mouth of the Sairenji opened with pleasure.
Issei rammed into her hard, his pelvis colliding with Haruna's crotch who saw him with her mouth and eyes wide open, the female moaning much harder, almost screaming while Issei thrusted into her with increasingly erratic movements.
The kiss awakened the dragon.
"Haruna..." Issei murmured his friend's name affectionately.
The blue-eyed beauty couldn't help but feel her heart jump upon hearing her schoolmate's words, her pussy receiving Issei's whole cock, the pleasure dominating her.
She never thought sex would feel this good.
"Issei, Issei..." The bluenette moaned her friend's name.
Issei couldn't hold on much longer, writhing on top of the Sairenji, who closed her eyes and hoped to receive her friend's seed inside her.
The red dragon had enough self-control to pull his cock out of Haruna's tight hole, the brown-eyed male jerking off a few seconds before cumming on his friend's stomach, who only saw him with blurred eyes, unresponsive to the hot sensation on her belly.
"I thought you're going to cum inside." Haruna told him, noticing the semen coating her stomach.
"I didn't think it would be right." Issei scratched his cheek, his cock resting on the teen's thigh. "This is just me helping you with the Rito thing, remember?"
"Ohhh..." Haruna didn't know why, but she was disappointed. "I understand."
Issei tried to get up, but Haruna grabbed his shoulders and hugged him, the foreheads of both colliding, the boy watching with wide eyes as the girl smiled at him with flushed cheeks.
Haruna has never looked so beautiful.
"Do you think we can continue practicing?" The cute girl asked the Hyoudou. "Ju-just for training!"
Issei kissed her, responding the question with actions, the Sairenji feeling his cock harden against her thigh, and could only hug Issei tighter, wanting to continue practicing and then become a couple with Rito...
Yes... This was just practice.