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Published:
2019-12-12
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2026-09-03
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6/?
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High School: DXD: Red Dragon's Journey

Summary:

At Kuoh Academy, there is a delinquent girl who is destined for greatness, and it all starts with her death. Join Issei Hyoudou as she begins her journey to become; A HAREM QUEEN!

Notes:

HELLO, MY NAME IS DARTH WIDOW, AND THIS IS MY SECOND STORY ON THIS SITE. Anyways, I have been rewatching High School DxD and I am watching it in Dub, and I was inspired. Now, is this shit, most likely, yes, but I still hope you enjoy it anyways.

(See the end of the work for more notes.)

Chapter 1: Death of The Hero

Chapter Text

Chapter 1: Death of the Hero

“Red.”

“The same color as her hair. Darker than any red hair that I’ve ever seen.”

“Just like the color running down my hand.” 

“Long beautiful crimson hair. Just. Like. This.” 

Suddenly, the beautiful woman in front of me said these words. 

“Not today, I will not let you die.” Then, there was nothing, but darkness. 


“Oi, Issei! Issei wake up!” 

“AAHHHHHH...eh?” I woke up and saw the entire class looking at me, including my teacher. He sighed in disappointment, something I manage to do often.

“Miss Hyoudou, I understand if you don’t want to learn in my class, but please don’t fall asleep in class.” This caused the class to laugh, and me to shrink down into my seat. 

“Sorry, teach.” I said as I blushed in embarrassment. The teacher just sighed again and continued to teach the class. 

But yeah, that embarrassed girl is me, Issei Hyoudou, a school girl in a male uniform and a red shirt that is in year 2, class 3-B at Kuoh Academy. I have Short, spiky hair, brown eyes, fair skin, a height of 5” 7’, and D-cup breasts. Though you know what I look like, you might not realized from my embarrassed ass is that I, Issei Hyoudou, have a dream; to have a harem of beautiful big breasted women! Why, you may ask? It is because I am one of the perverted trio!

To be honest it’s not a title I am proud of, BUT IT IS NOT WRONG!

It’s just that, I have always loved women, and now that I think about it, probably to much. Maybe I should try and lower my pervertness, maybe then I can get a girlfriend. I don’t know. 

Suddenly, the bell rang, and the teacher said, 

“Remember to look over chapter 21 and remember the historical figures in the chapter.” Most did not pay attention, but I made sure to, since I did fall asleep in class. 

“Hey, Issei, want to watch the girls track team?” I look over to the voice to see my friends and the other 2 members of our Triumvirate. The voice was from Mastuda, the tallest of the three, and the self proclaimed ‘lolicon’ of the group, with large ears, black eyes, and a shaven hair, giving him the nickname: Perverted Baldy. Next to him was the shortest of us with black hair, and large square glasses, apparently giving him the ability to see all the measurements of a woman, which has given him the monikers: Perverted Glasses and the Three Sizes Scouter. In all honesty, it’s impressive how he gets the sizes, hell, it’s how we became friends. 

In the end, I smiled at them and said,

“Sure, let’s head to the hill next to the track.” They both looked at each other and shouted,

“ALL RIGHT!” and proceeded to high five each other while I just chuckled and walked with them to the track. 


“Hmmm, I’ve got to say, boobies are awesome.”

“Trust me, man, you and I are on the same page.”

“Me to, but it’s all pointless.” 

The three of us were all lazing around the hill next to the track as the girls track team did their daily training and looking to the sky. Honestly, it was great. I then sat up and asked, 

“Mastuda, Motohama, why did we enroll in this school?” Matsuda laughed at this. 

“Like you don’t know. We’re in a place that up until a few years ago was nothing but chicks.” Motohama continued. 

“We had to take advantage of the ratio, and the rate of foreign exchange students here are ridiculous.” I nodded at this.

“Yeah, the rate for foreign exchanges are weirdly high.” Matsuda continued from my comment.

“Poon as far as the eye can see, we figured hoes would be lining up to get on our jocks! We wouldn’t have to do a damn thing! We’d be drowning in pussy!” Suddenly, I got up, and decided to be a little dramatic and shout out our dream. 

“TO HAVE OUR OWN HAREM!”

They posed with me.

“HELL YEAH! WE WERE GOING TO HAVE CAUSAL, UNPROTECTED SEX WITH HOT CHICKS AND NEVER CALL THEM AGAIN!”

We got out of our poses and Motohama reminded us of our sad situation. 

“That was the plan, however, yet here we are, it’s the spring semester of our 2nd year and between the three of us, no one has gotten a single girlfriend. What’s the point, it will never happen.” Motohama said in disappointment. However, I knew we must not falter, less our dreams nay come true. 

“No! We can’t give up now, it’s not too late for us!” Suddenly, we noticed Yuuto Kiba, the ‘Prince of Kuoh,’ and basically it’s top bachelor walk near us, and he started talking. It was too late when he showed up. We all watched as he disappointed some girls with his refusal of their request. 

“Yuuto Kiba,” Motohama stated, “Class 2-C, basically every girl wants to sex him up.”

“Every guy wants to mess him up.” Matsuda joined in. The talk about Kiba frustrated me and I couldn’t hold it in.

“AAHHH! THAT TOOL! GODDAMN IT! JUST CAUSE HE’S HOT AND SEXY, SMART AND THE COOLEST GUY IN THE SCHOOL THEY ALL WANT TO RUB OFF OF KIBA!” 

“Woah, you called him hot and sexy, you fallen for guys now~” 

“Up yours, Matsuda!” 

“Uhh, he sucks so much less than we do.” 

“Uhh, life really blows sometimes.” Matsuda then checked his watch and freaked out a little.

“Oh shit! I’m gonna be late!” Me and Motohama looked at him confused. 

“Um, you’re going to be late for what?” I questioned, he simply looked to us and smiled and gave us a thumbs up, then continued to walk away. Me and Motohama looked to each other, then to Matsuda, and then followed him. 


“Murayama’s jugs are freakin’ huge!” 

“36/22/34.”

“Katse’s legs are crazy sexy!”

“34/22/36!”

At this point, Matsuda and Motohama were crowding a peak hole, wiggling their booties in delight at the sight of the girls in their underwear. Meanwhile, I’m being left out, technically on watch duty, with my arms crossed and my right foot and index finger tapping at different surfaces in annoyance. 

“I found this yesterday. I call it the ‘tithole’!”

“Good job Matsuda! I have to admit---” Motohama kept saying gibberish and I had enough.

“Alright! That’s it! Let me see!” I said angrily. I grabbed Matsuda by his butt and tried to pull him out with all my might. Suddenly, we heard one of the girls say 

“Huh what was that?” And then Matsuda and Motohama backed up and the former yelled, “RUN!” which they both did in opposite directions. However, this caused me to fall down on the ground. 

“Great, they left me here, fantastic.” Suddenly, I was frozen, and I felt the intent to kill me, and it was strong. 

And behind me. 

I slowly turned around to see Murayama and Katase and the rest of the FUCKING KENDO CLUB behind me. 

“Well well, what a surprise?” Murayama said. 

“Oh. Oh shit, listen, I know how this looks, but-” All the girls lifted their kendos, preparing to strike.

“P-p-p-please, don’t hurt me.” For the next 2 minutes, there was nothing but the snapping of kendos and the cries of a girl in pain. 


“Ah shit, that hurts.” After the beating I received, I rendezvoused with the rest of the trio outside the house of the Occult Club. They did a ‘ooooohhh’ when they saw me, having multiple bruises, a cut lip, and a black eye, they made sure I was punished, that’s for sure. 

“Well, did you at least get to see some nip?” I looked at Motohama with hatred.

“No, I didn’t see any nip! I was too easy getting my ass handed to me by the kendo club! Because I look through a peephole I didn’t see through you~” I suddenly felt like someone was watching me and looked behind me.

“Ass.” I saw red, like the girl in my dream, like the hair she had.

“Holes.” I was blushing, I knew I was as I saw this girl on the window. She looked down on me with her sparkling blue eyes, the color of the sea, as her crimson hair flowed through the wind. 

The other too looked up to where I was looking and saw her in the window. When that happened, she walked away into the darkness of the house. 

“Did you guys see that honey!? Her sugar has got to be sweet.” 

“True that. What is it about red hair.” Motohama smirked and adjusted his glasses.

“Her name is Rias Gremory. 36/24/36.”

“Oh shit.” I whispered to myself. 

“She’s the president of the Occult Research Club. Word around the school is she’s from Northern Europe.”

“Hmm, Rias, Gremory.” There was something about that name that made me immediately want to know more about her. 

Little did I know, I would get to know her very soon. 


Later in the day, I was walking home and the sun was setting on the city, it was honestly a beautiful sight. As I walked on the bridge, I decided to stop and look out to the highway, as I sigh in defeat. 

“Ugh. I’m never gonna get laid, or get a girlfriend, or anything. Fuck me. Well, I guess it makes since, who would ever want a perverted delinquent like me?” I then put my arms on the handlebars on the bridge and put my face into my arms in disappointment. It’s true though, the more I think about it, the more I realized I fucked up and that, in the end, I am going to be a virgin forev-

“Um, excuse me? Are you Issei Hyoudou, from Kuoh Academy? Or am I wrong?” I looked up to see a large breasted girl with long black hair, a red uniform that I didn’t recognize, and ruby colored eyes. Speaking of her ruby eyes, they widened in shock of the bruises that I still have. 

“Um, are you ok.” 

“Oh, yeah, I’m fine, don’t worry about it. Anyways, may I ask who’s asking for me?” The girl in front of me started to blush and the question and started to stutter. 

“I-I wanted to know if you were dating anyone?” This confused me, why was this girl asking if I was single………………….

Wait.

“Um….why are you asking?”

“Well, I was just wondering if you were single, and if you were, if,” She looked away at this point, still blushing. “If you wanted to go out with me.” 

Wait.

WHAT!

“Wait, go out with you, like, as a couple?” She looked back up to my face and smiled at this.

“Yes! You see, I noticed you walk through this bridge often and you always looked so beautiful and handsome at the same time. While there were times it seems like you're a delinquent, I also felt that you were lonely and-”

Wait, was this actually happening, does a girl actually like me? Am I not going to be along. I have to pinch myself.

.

“See, the thing is, I want you to be my girlfriend.”

.

Holy shit. This is real. 

“Soooooo. When do you want to go out?”

“Um, would next Sunday work?”

“Yeah, that can work, honestly, any day would work.” Yumma giggled at this and said,

“It’s a date then. Night!” 

“Yeah, you too.” With that, she ran to the direction she appeared from and turned to me at the last minute and said,

“I’m really am happy you’re my girlfriend!” 

I think my heart skipped a beat. 

“Um, diddo, see ya around.” I waved back to hear slowly, my mind still processing what the hell happened. However, it passed like a bird’s shadow and I clenched my fist and raised it in the air. 

“Hell yeah! I finally have a girlfriend! AND I HAVE A DATE!” 


“Wake up please! Would you wake up now!? Or, you can just stay in bed, but I would come down on you. Wake up, Mister! Wake up, Mister! Wake-”

*CLICK*

I looked up to my clock, laughed, and smirked. Why, you may ask? Simple. It is because today is the first day that I, Issei Hyoudou, have a girlfriend. 


“NO, PLEASE GOD!”

“OH!” Matsuda and Motohama were in disbelief when my beautiful girlfriend appeared to meet with me. I decided to make things not awkward and introduce them to my girlfriend.

“Matsuda, Motohama, this is my girlfriend, Yumma Amano.” I then turned to Yumma, my left hand pointing to the two boy’s still gasping in disbelief. “And these are my buds, Matsuda and Motohama.” She turned to the boy’s with a smile on her face. “It’s nice to meet you.” And just to rub it in, I went up to Matsuda, I went up to him, put a hand on his shoulder and whispered into his ear loud enough that he and Motohama could hear it. 

“And here’s the best part, dudes. She. Asked. Me. But hey, if you stop wacking it, you’ll find one too.” I walked over to Yumma after probably, most likely humiliating my two friends. 

Honestly, a dick move on my part.

“Come on, let’s go, Yumma.” 

“Kay.” And we both walked away, with Yumma bowing before them. But I did manage to hear this.

“DUDE, SHE BETRAYED US.”

*INTENSE CRYING*

Was I a dick, yes. Was it worth it?

Hell. Yes.


Later in the week, it is now Sunday, and I had a bit of a costume change for the date. For the date, I now have a grey coat over a black shirt with red highlights, that is lifted up enough to see my lower stomach, along with some grey jeans. I am currently waiting for my girlfriend to show up, but it seems she’s late. 

“Man, I really hope she didn’t forget about our date.” 

“Here, take a flyer.” Suddenly, a hand reached out in front of me with a flyer in hand. I took the flyer and looked to the voice to see a woman with short brown hair and brown eyes. She also had red lipstick covering her lips and I red dress with a yellow bow in the middle of her dress, she also had black cloth on her shoulders which gave the appearance of webbed wings, as well as bat wings on her back and yellow hoops around her arms. Huh, what a weird cosplay. After giving me the flyer, she simply smiled at me and walked off. 

“Well, what the hell is this about.” I say as I look down to the flyer. “Your wish will be granted, eh?” I scowled at this. “What a bunch of bullshit.” But something compelled me to keep flyer. So I decided to put it in my pocket. 

“Issei, hey!” There she is. My beautiful girlfriend with with a pink dress and purse as well as a black skirt.

“Hey, babe! You made it!” 

“Sorry to keep you waiting.” 

“No, it’s ok. In fact, I’m just glad you came!” Hell yes! Not gonna be stood up! HELL YEAH!

The date went great in my opinion. We went shopping for clothes first and I was able to get some new shirts out of it, while I was able to get her a scrunchie. After shopping a bit more, we stopped for a lunch break where Yumma fruit parfait. I simply had some green tea and snuck a look at Yumma generous breast, which cause me to almost die.

I didn’t. Don’t worry.

After that, we did some stuff at the arcade, it turns out that Yumma is very good at Mortal Kombat, like, really good, it’s honestly terrifying. We also did a bit of Dance Dance Revolution and I think we got heated cause after that, we were in each other’s arms, panting, sweating, and looking longingly into each other’s eyes, but I turned away and blushed. Yumma chuckled at this. 

However, now it is the end of the day and the sun is setting. Me and Yumma have reached a large fountain that glistens in the sun. 

“I sure had fun today.”

“Yeah, so did I, I really enjoyed it.” As we walked towards the fountain, our hands touched and I blushed, but I decided to take the initiative and decided to hold my girlfriend’s hand. She gasped at the sudden contact but we kept walking. I like to think she smiled at the contact. With the fountain glistening and with the sky a beautiful color of orange and bronze, I took my chance. 

“Yumma.” 

“Hmm.” I stopped in front of the fountain, grasping both of her hands and looking towards her. 

“I’m going to be very forward, but I have to ask you, can I kiss you?” Yumma looked at me with a surprised look, but then smiled and said, 

“Yes.” I froze. She agreed, holy shit she agreed. So, I leaned in and so did she, and I did the leap of faith and.

I captured her lips.

Her lips were sweet and it felt as if I saw color for the first time in my life. As we kissed, she put her arms around my neck and leaned into my body. As we continued, she pushed her tongue in so I fought in kind, I think I was able to get control of the situation. However, before we could continue, Yumma pulled out and put her forehead on mine. 

“Wow.” 

“Yeah, Wow.” However, I heard something originate from Yumma.

“Yumma?” I looked down to see Yumma with her eyes closed and tears streaming down your cheeks.

“Yumma, are you ok?” I wrapped my arms around her as she started to cry and held her, and then I heard her, in a voice deeper than what I’m used to, say, 

“I love you.” I froze, but then, I felt a pain in my gut and looked down, Yumma held in her hand, a spear of light, and it was penetrating my gut. 

“Yu-mma? GUH!” I puked out blood and saw my gut spewing out blood by the gallons. Holy shit there was so much. I looked up to see Yumma, but she had changed. She now wore skimpy black leather that strapped around and under her breasts while she had a three-strapped thong, shoulder plates with three spikes on her right pad, gloves that went to her elbow, and high heel boots. However, what surprised me more were wings, dark, black wings of something of what can be described as an angel. In all honesty, I loved the new look, however, I couldn’t focus because of one little bitty thing, nothing major. 

I. AM. DYING. 

I looked to Yumma. She looked at me with tears down her cheek. However, I did notice something that made me smile. 

“I-I’m sorry, Issei, but you were too dangerous to be kept alive.” She walked towards me as I fall to my knees to the ground. “With what you have inside of you, I couldn’t risk you destroying us, but.” She paused, wiping her eyes as more tears fell down. “I didn’t expect to fall in love with you.” 

“The scrunchie.”

“Huh.” Yumma looked down to her left hand to find the scrunchie still on her arm. 

“You kept it on.” Yumma looked to me, as I smiled with happiness. 

“I know you are killing me in all that, but for some reason, you wearing that. It really warms my heart.” Yumma stared at me for a second and hugged me, yelling, 

“I’m sorry!” Over and over again. Me, I was content, I finally got a kiss, would I die a virgin, yes, that sucks, but at least I got a kiss. Yumma calmed down, and kissed me on the forehead before laying me down on the ground. She leaned down to my ear and whispered, 

“I love you.” And then took off into the air. 

Which is where I am now, dying on the ground, with no possible way to save myself. While I am content with dying, a small part of me doesn’t want to yet. I want to complete my dream, I want to get laid, get a harem, and honestly, see Yumma again, as fucked as that sounds. However, the last thought of my mind wasn’t of Yumma, no. 

It was Rias. 

Her crimson blood hair, her big, juicy breasts, her sea blue eyes.

I wish to also see them. One. More. Time. 

“I have come, you’re the one who summoned me, are you not?” I looked up with my eyes to find bouncing breasts and crimson hair flowing in the wind, with a red glow around her. It’s her.

It’s Rias. 

“Since death is nearly upon you, I will gladly take you in.” Suddenly bat wings appeared on her back. 

.

.

.

Wait, bat wings?

“From this moment forward, you will live your life for my sake.” 

After that, the last of my breath faded, and with that, the last of my conscious. 

At 6:58 P.M. Sunday. I, Issei Hyoudou, died.