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A Crossover between The Dresden Files and High School D×D by Gabriel Blessing, that started out like another typical crazy week for Harry Dresden.

In this case, fighting a Walker on the wrong side of the Outer Gates after sealing them. As a last ditch effort, Harry decided to use the most destructive method he knows to deal with it; combining Hellfire with Soulfire. It worked... somehow.

However, he finds another problem; a horizon-spanning dragon, that even the Walker is terrified of, now approaching both of them. With no other option, Harry turned to Lash for help and opens a Way....

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And ends up in Japan, of all places. In a teenage body. Long story short, he enrolled in Kuoh Academy and Hilarity Ensues.

So, read on as Harry rediscovers how much he hates hormones, bullies innocent school devils, and indulges in Buddy Cop antics with the voices in his head!

The original story is a Dead Fic, last updated on July, 2014, consisting in 3 chapters and 140,000 words. The two initial scenes of Chapter 4 were released by the author on a forum — titled The Missing Files and including the "Gender Bender Gun" episode — and can be read here or here.

The ongoing recursive continuation by Xavon Wrentaile titled Beyond the Outer Gates Lies... A high school library? has its own page.


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Beyond the Outer Gate Lies... provides examples of:

  • Achievements in Ignorance: Harry developed a protective enchantment against the power of Light for his coat, as it is his policy whenever someone tries to kill him with something new, without knowing that non-Holy, Light-resistant items that Devils can use are unheard-of in Bizarro World. It's no wonder he left Rias and Sona's Peerages in Stunned Silence when he mentioned it in passing.
  • Adaptational Early Appearance: The Hero Faction appears in this fic much earlier than they do in canon, attracted by the possibility of recruiting Harry. Then they kidnap him during the Kuoh Conference to lock him out of the fight and officially offer him to join them.
  • Almost Kiss: Harry and Sona have a Slap-Slap-Almost Kiss; she is pulling his cheeks and he is mussing her hair when they trip and fall into a compromising position. They then almost kiss, but Saji stops them.
  • Amazingly Embarrassing Parents:
  • And Call Him "George"!: Mentioned almost verbatim by Dresden, during the fight with Raynare:
    One of these days, I swear: a monster or creature that slithers in the night that is actually physically weaker than a human. I will find it. I will make it my pet. I will name it George.
  • Angels, Devils and Squid: Adds The Dresden Files' Outsiders as the Squids to the existing High School D×D Angel and Devils.
  • Anger Born of Worry: Harry's Chronic Hero Syndrome and Sona's Team Mom-ness tend to mix into this. Not a good thing when Harry is coming down from using the Winter Mantle because his Superpowered Evil Side tends to register her worry-filled scolding as a challenge to its authority.
  • Attractive Bent-Gender: Pretty much everyone. Special mention to Harry, who remarked how "uncomfortably good looking" his tall and shapely female form was, his numerous scars giving "her" an appealing dangerous sort of air rather than detracting from her beauty at all.
  • Author Appeal: Compared with his other works, Gabriel Blessing shows certain taste in his stories:
  • Balanced Harem: Invoked. Sona and Tsubasa have some tacit rules about how they go about the romantic pursuit of Harry. The gist of it seems to be that each of them can take things as far as they comfortable with the other girl getting with him. This is why Tsubasa was in fact disappointed that Harry and Sona's private magic study sessions are actually just that — otherwise, she'd have considered fair game to be a little more daring in her seduction attempts.
  • Bizarro Universe: Harry refers to the High School D×D universe as this, and it fits the profile. In The Dresden Files, devils and angels (both regular and Fallen) are pillars of creation, have nigh-infinite power, can only be created by God, and are almost as hard to kill, and God is alive. Magic functions on willpower and emotion, and causes users to become Walking Techbanes. And the wizard never gets the girls. In High School Dx D, most devils aren't that much stronger than humans, they can reproduce normally or turn humans into devils, and can be killed almost as easily, and God is Dead. Magic is performed with complex math, and has no negative effects on technology (what first tips him off to the fact that he's in a new world, is the fact that the hospital machinery he was hooked up too was still functioning, even when his emotions were flaring). He's also getting some female attention...
  • Blind Jump: This is how Dresden wound up in the middle of Japan in a teenaged body.
  • Boobs of Steel: Believe it or not, Harry Dresden himself. Courtesy to Azazel's gender-bending gun.
  • Break the Haughty: Raynare openly mocks Harry even after he practically handed her ass. Then Harry uses Soulgaze on her.
  • Bully Hunter: Harry, which is why he got (politely) kicked out of the school he attended before Kuoh.
  • Bullying a Dragon:
    • Literally, the Hero Faction wants to kill Great Red, a dragon with teeth longer than Dresden is tall, as said wizard himself puts it, and leaves others alone as long as they don't hang around the Dimensional Void, in order to prove humanity's strength. And this doesn't even take into account his defense of the world against the Outsiders...
    • For a less serious example, don't try to play The Gadfly at Harry's expense if you don't want him to answer in kind. Tsubaki learned this the hard way when her attempt to put Harry on the spot with his two would-be girlfriends got her stuck alone and "udonless" with the Student Council's unfinished work for the rest of the day.
  • Caught the Heart on His Sleeve: When Azazel offered Harry a place with the Fallen in the Grigori, Sona picked up on his hesitation and grabbed the edge of his coat as she realized that he would most likely disappear from her life if he accepted.
  • Change the Uncomfortable Subject: When Harry denied the misconception that he was into group sex (long story), he said he "prefers genuine emotional closeness in [his] relationships." Tsubasa then remarked that he's got to have some experience in the matter if he can say he "prefers" things that way. Harry immediately diverted the conversation to his magic lessons.
  • Chaste Hero: Being mentally an adult, it never occurred to Harry that all of his friends in Kuoh Academy are inexperienced about sex. He only realized it after telling them how annoying it was for him to sometimes get home and find his brother with a woman or even in the middle of an orgy. He only meant it as an anecdote, but all he got was a roomful-worth of red faces.
  • Chekhov's Skill: Harry used his Soulgaze on Raynare to discern whether D×D supernatural entities like her could have Souls like he understood them. The results were an affirmative answer to that question in the Fallen's case, and the confirmation that seeing his Soul can be a sanity-breaking sight if the other person isn't made of much sterner stuff. Later on, during the Kuoh Conference, Harry initiated a Soulgaze with Azazel as part of a Batman Gambit to get the Three Great Powers wary of involving innocent humans in their conflicts, counting on the reputation of the Leader of the Fallen and his knee-jerk reaction to the Soulgaze to make everybody present take the words of the seemingly-harmless Magician several Power Levels below them seriously.
  • Chuunibyou: Harry tries to continue his Occult Detective work in Bizarro World, business cards and all, but being reverted back to his adolescence makes most people assume he's this trope instead.
  • Combat Pragmatist:
    • Harry's entire combat style, as usual. From trying to get guns again, mentioning how he loves that no one ever sees a Squishy Wizard throwing a punch coming, and even saying that "if you're not cheating, you're not trying".
    • This attitude also seems to be rubbing off on Issei.
  • Comedic Spanking: Issei and Saji get spanked by Rias and Sona, respectively, for being reckless during a mission. What makes it even funnier is that when Issei begs for Harry's help, he can only shrug and point out that there are places where people pay for that sort of thing before leaving Issei to his fate.
  • Comically Missing the Point: During the Kuoh Conference, Harry explained what a Soulgaze is and rhetorically gave everybody present three guesses to figure out who is the only one who initiate one for sure. Being unaware of the incident with Raynare, Serafall thought it was a legitimate question and guessed "Azazel" after him and Harry had their Soulgaze.
  • Commonality Connection:
    • Harry and Issei over their tendency to help those in need, especially when The Dulcinea Effect is involved, and protect their friends above all else. The difference is that Harry's a Knight in Sour Armor after all he has lived through, whereas Issei remains more of a Wide-Eyed Idealist.
    • Harry and Sona bond over their magical studies, with him as the geeky researcher and developer, and her as the aspiring educator who wants to devote her professional future to teach magic to others.
    • Harry and Serafall hit it off pretty well after their initial My Sister Is Off-Limits! moment, because they're both eccentric professionals trying to do their jobs their way despite traditionalists giving them grief for it.
  • Cosplay Otaku Girl: Lash. Outfits she has appeared in include a Bunny Girl costume, maid outfits, and a gym uniform (complete with bloomers).
  • Crazy Jealous Guy: Sona's interest in Harry makes Saji hate his guts. He even covers Harry's fees in the missing Excaliburs case, just to make sure he will be too busy with work to hang out with the student council. Interestingly, this is also an example of Why Can't I Hate You?.
  • Crossover: The Dresden Files and High School D×D.
  • Dark Is Not Evil: Harry is shocked to discover this applies in this world, since in his own world, devils and monsters are almost invariably evil.
  • Dead Fic: As of 2017, it's been well over two years since the last snippet of the incomplete fourth chapter was posted. The continuation fic picks up where this one left off.
  • Deadly Dodging: An accidental, Indy-worthy example. Harry escapes from Georg's Pocket Dimension through an Aparturum portal with Heracles' missiles still in hot pursuit after him, only to find Kuoh Academy under attack by the Old Maou faction. Without thinking it twice, Harry runs to the first enemy he sees and dodges, letting the attack meant for himself do the rest.
  • Defcon Five: Parodied. Harry measures the likelihood of Sona pinching his cheeks on the "Pinch-Con" scale.
  • Deliberate Values Dissonance: This Crossover and its Continuation Fic explore the implications of the Devils' cultural acceptance of harems a bit more seriously than the original material, as a result of having a protagonist who isn't a Hormone-Addled Teenager Lovable Sex Maniac Harem Seeker. Namely, it takes Harry a while to figure out why it is so — according to Azazel in the unpublished fourth chapter, it's a combination of the Devils' Authority Equals Asskicking and The Hedonist mentalities, together with their centuries-long lifespans and extraordinarily low birth rates — and then some more to accept that Sona and Tsubasa are actually okay with the other pursuing him romantically and not at each other's throats for it, like his common sense tells him they should be.
  • Dirty Old Man: Despite being physically in his teens and having no means to return to his real age other than the natural way, Harry feels like this about his unexpected love interests, since he's mentally in his 40's. He's torn between both his attraction to them and that he feels a personal connection to Sona and Tsubasa, and the fact that he is technically old enough to be their father.
  • Dramatic Drop: Harry drops a box on his toe when Lash tells him Sona is into him.
  • Flipping the Bird: Right as he's escaping from Georg's Pocket Dimension, Harry makes sure the last thing the Hero Faction sees of him is his raised middle finger.
  • Fountain of Youth: Harry is aged down to his teens again when he enters the High School D×D world.
  • Freudian Slip: Harry refutes Sona's misconception about him being at slacker by saying that she can "bet [her] sweet ass" that will put in all the effort that his magical studies deserve, only realizing post-rant that he "also brought up Sona's ass with the adjective 'sweet' in front of it." It becomes a Brick Joke by the end of the scene where she asks him to "please refrain from commenting on [her] bottom", to their mutual awkwardness.
  • Funny Background Event: When Sona had Harry filling envelopes alongside the Student Council in exchange of charging up his laptop at school, he sneakily tried to put some of his unfinished work into Tsubaki's pile while Sona had the room distracted with her conversation with Saji. Without even looking at him, Tsubaki put it all back in Harry's pile.
  • The Gadfly:
    • Harry, several times. His most trollish moment has to be when he pulled Rias' leg by commenting on the potential cultural consequences of a show like Oppai Dragon getting as popular as it did in the Underworld, including the possibility of couples cosplaying as the characters based on Issei and Rias during sex. Azazel immediately sees the potential profit in selling ero-versions of the outfits worn by Oppai Dragon and Switch Princess, before an incredibly embarrassed Rias tries to shut down the idea with her Paper Fan of Doom. Then Harry delivered the coup de grace by wondering aloud what Sirzechs would do if he hears about it. Given how much of a siscon the Maou is, Harry just knew that Rias' brain would picture her brother trying and perhaps managing to convince his wife to roleplay as a fictional character based on his little sister in bed, which almost gave the poor girl an aneurysm. Harry was quite pleased with his handiwork until Lash congratulated him for it, which is when he knew he went too far.
    • Once Harry learns about the Devils' gift of tongues, he makes a Running Gag out of having Lash switch languages mid-conversation just to see how long it takes them to notice.
    • After Issei finds out about Lash, and how she can manifest herself as a pretty woman, Harry pretends that she's taking her clothes off to get Issei to freak out, and Asia to try to prevent him from gropping the non-corporeal entity. Lash notes that normally she'd be mad at him for lying about what she's doing, but in this case approves of the results.
    • Lash's masterful trolling of Harry deserves a mention, especially considering that she only can speak directly to him and yet she still manages to push him into embarrassing situations. A good example of this is when he tricked Harry into saying something aloud that made Tsubaki think the two of them were engaging in "Maid Naked Apron play" (Tsubaki's words). The How Much Did You Hear? moment and having another two fetishes attached to his name were bad enough on their own, but Lash's real objective was a doozy of a Batman Gambit that ended up with half of the girls on the Student Council (plus Akeno) wearing maid uniforms the next time he opened their office's door. Even Harry was impressed.
  • Gag Boobs: Female Harry is even better endowed than Rias!
  • Gender Bender: Harry gets caught up in the Occult Research Club's shenanigans with the gender-bending gun.
  • Gossip Evolution: An enemy Harry wasn't prepared to face: gossiping teenagers.
    I wasn't certain which of the members of Sona's peerage had been the one to start the rumors, or if they had done it on purpose, but apparently the day after I had had my pow-wow with them it had been a popular gossip that the three of us were in some kind of love triangle. It had taken a day after for it to be common knowledge that I was leading them on, and the next day it was established fact that I was cruelly taking advantage of two innocent girls while engaging them in depraved sex acts.
    Hell's bells, these people needed hobbies.
  • Got Me Doing It: Harry calls the swords forged from the broken pieces of the original Excalibur "Excalibits". The term proves to be catchy enough that it even gets the serious Sona to use it.
  • Harem Nanny: Lash, in a twisted way.
  • Harem Seeker: By proxy. Lash likes to tease him with the idea of Harry having a harem. She was actually serious about it. The only time he let her talk with Sona, supposedly to give them the chance to have a "woman-to-woman talk" about Lash helping Harry cheat in his tests, Lash told her exactly what Sona and Tsubasa needed to hear to start acting on their feelings for Harry without clueing him in until he asked.
  • Hearing Voices: Issei asks Harry for advice about the voice in his head (Ddraig's). Harry gives him the rundown of the do's and don'ts of a hosting a supernatural entity within his own person.
  • Hidden in Plain Sight: Being too young for a driving license means Harry can no longer do his stakeouts covertly from a car. Short of time for a better alternative, Harry opts for acting as the "yankii" delinquent that people already think he is and plays up as many stereotypes as he can, counting on people's reluctance to get involved to remain for hours standing in a fairly busy intersection without anyone bothering him.
    Harry: [grumbling to himself] Embrace the clichè, Dresden. Use the clichè, and make it your power. Who needs a good reputation anyway? Bah. Stupid things, good reputations. Never had any use for them.
  • Hoist by His Own Petard: A comedic version. When Harry meets Sirzechs, he calls upon his rusty manners, but can't help tossing in a "Sympathy For the Devil" reference. A moment later, Sirzechs gets the joke and continues it, causing Harry to briefly concede defeat.
    Harry: My God, my minister was right all along. Rock and Roll really is the devil's music.
  • Hormone-Addled Teenager: Harry hates the unavoidable fact he's back to being one, especially how his teenaged hormones affect his thought processes and make him feel attracted to girls young enough to be his daughters.
    And yes. It really was as bad as the first time. Anyone who says "youth is wasted on the young" is a freaking moron. Only the young don't know enough to know how bad they really got it.
  • Horrifying the Horror:
    • Even the Outsiders are scared of Great Red. Harry eventually theorizes that he's what keeps them out of Bizarro World.
    • A Soulgaze with Raynare sends the Fallen into a Villainous BSoD, begging Rias's peerage to keep Harry away from her.
  • I Have Boobs, You Must Obey!: fem!Harry in the omake has this as an almost literal super power. Seriously.
    Reya: Amazing. Dresden-kun! Apparently, your b-breasts have the power to ensnare those who stare at them for too long
    Momo: Amazing. Is it some form of hypnotism? Or is it perhaps the "breast power" that Azazel-sensei has been experimenting with?"
    Harry: [disbelieving] Breast power?
    Ruruko: It's something Azazel-sensei has been investigating. It's something he's been researching ever since Hyoudou-kun started showing signs of unusual development as the Sekiryutei. Is it possible that Dresden-kun too has this "breast power" when he is in the form of a maiden?
    Saji: How dangerous! If one looks too long, than you might be ensnared, but it's impossible not to look! W-What a horrifying power!
    Harry: You're all crazy. I'm leaving now. My life has too much crazy in it as it is.
  • I'm Taking Her Home with Me!:
    • Harry to Asia. Every time she seems happy or upset, Harry gets the urge to take her some place nice and shower her with ponies and kittens.
    • He feels similarly about Koneko in her more vulnerable moments.
  • In My Language, That Sounds Like...: A lot of Harry's initial problems with Sona where from the results of a misunderstanding. A student asks Harry if he's a "yankee". Harry, being from Chicago, says yes. He didn't realize that the student heard of his bad reputation and that "yankii" was Japanese slang for delinquent. Sona got wind of it and has been misguidedly trying to reform him.
  • Innocently Insensitive: One of the first clues of Sona's romantic interest in Harry was how uncomfortable she got when he told her that a female client kissed him on the lips without warning as a final "screw you" to her ex-boyfriend after the private detective brought her evidence of his infidelity. Harry mistook Sona's reaction for sympathetic anger at the cheating guy.
  • I Resemble That Remark!: Lash remarks beyond her hopes, Harry didn't set the building on fire after Sona's failed recruitment. Harry says that he doesn't set every building on fire and he will burn alive the guy who started the rumor. Lash snarks that would definitely prove his point.
  • I Take Offense to That Last One!: After finding out that Georg is a fanboy, Harry snarks that if he's got a stalker, why couldn't it be a "hot, overeager, sexually aggressive cheerleader", prompting Siegfried to jokingly suggest Jeanne put on a cheerleader uniform. She refuses, but her specific wording causes Harry to lampshade how she only objected to the cheerleader part.
  • Laser Blade: Harry has a Nerdgasm when he realizes that lightsabers exist as an Exorcist's weapon in Bizarro World. He even pockets one from a defeated enemy to tinker with it.
  • Laugh Themselves Sick: Lash reaction after Harry gets turned into a woman, courtesy of Azazel's gender-bending gun.
  • Light Is Not Good:
    • Harry finds out the hard way that not only is Dark Is Not Evil, the side of the angels are just as flawed as everyone else. Justified since God is Dead, leaving his imperfect creations to try to carry on as best they can.
    • Same goes for the Hero Faction. Their intentions might be noble, giving normal humans a place in a world of magic and monsters, but unfortunately their plans are missing critical bits of information that could make them cause more damage than they would solve. Furthermore, Harry has ideological differences with the Hero Faction because they don't really care about the collateral damage so long as they prove Humans' strength to the supernatural world, whereas Harry's priority concern is protecting as many humans as he can from the supernatural.
  • Little Girls Kick Shins: Sona still resorts to this when really annoyed with Harry despite being older than him (legally speaking, that is). The One Head Taller and Slapstick Comedy tropes made this pretty much unavoidable.
  • Man, I Feel Like a Woman: Lash outright suggests Harry, in a Spock cosplay no less, to "boldly go where no man has gone before" by "absconding to her quarters to masturbate".
  • Man of Wealth and Taste: Harry mentions facing more than a few of them. It's gotten to the point where he can tell the quality of a villain's outfit by the quality of its ashes — this is Harry Dresden we're talking about, after all.
  • Minor Living Alone: Harry lives and supports himself to get out of the foster care system, due to his bad experiences with it in his original world.
  • Misplaced Retribution: Played for Laughs. Harry blames Issei for putting the idea of harems into Lash's head. He swears his vengeance upon him in proper melodramatic fashion.
  • Mistaken for Gay: Having never seen him out of his Scale Mail before, Harry mistook Vali's constant staring at Issei during the Kuoh Conference as the silver-haired guy wanting to jump his bones. Harry even stated to wonder how to break it to him just how badly Issei is strictly into girls.
  • Motivational Kiss: Tsubasa gives Harry a good luck kiss on the cheek right before he hurries to reinforce Rias' Peerage against Kokabiel. Must be noted that his haste had admittedly less to do with the urgency of the situation and more about Sona's reaction at the sight.
  • Muggle Power:
    • The Hero Faction is a Type 2 to a T, which became the deal-breaker that made Harry reject their offer to join them. Harry only opposes those who would prey on humans, regardless if they belong to supernatural species or are even fellow magic-wielding humans. The Hero Faction would attack any sufficiently strong nonhuman if that proves humanity's strength to the supernatural world, regardless if said entity is a danger to people or not, and they don't really care about the collateral damage.
    • More specifically, both parties disagree on the Kuoh Treaty. Harry wants the peace treaty to go through because it limits the chances of normal people getting caught in the crossfire between the Three Powers, whereas the Hero Faction wants it to fail because "monsters fighting monsters" aligns with their objectives and its failure benefits their sorta-allies in the Chaos Brigade.
  • My Eyes Are Up Here: fem!Harry uses this when he notices both male!Koneko and fem!Kiba looking at him. He immediately lampshades that he never thought he would say that.
  • My Sister Is Off-Limits!: Serafall's initial attitude towards Harry. He wins her approval thanks to several points of Commonality Connection and his willingness to call her by her preferred nickname, "Levi-tan." He wins a lot more than her approval in the Continuation Fic.
  • Mythology Gag: When Akeno mentions that Harry playing mysterious about his magic is very intriguing, Harry states that it's like a drug.
  • Naked Apron: Lash donned the look once to trick Harry into asking her to Please Put Some Clothes On aloud, just in time for Tsubaki to hear him and get the wrong idea.
    Harry: How long were you there?
    Tsubaki: Er, Whatever it is you and Lash get up to at home, I don't think school is appropriate for Maid Naked Apron play. And should you really be doing such things when Kaichou has already confessed her feelings to you?
    Harry: [groans] God, kill me now.
  • Necktie Leash: Sona to Harry when she demanded to know what the Winter Mantle actually does. Poor timing almost made Winter Harry attack her for it before Lash managed to calm him down.
  • Nerdgasm: Harry's reaction when he learns the Exorcists wield Laser Blades.
    Harry: He has a lightsaber? I just had a geekgasm.
  • No Endor Holocaust: In the fragment of a chapter in the same thread the omake is published in, Harry rubs Ddraig's face in the enormous collateral damage he caused fighting a certain white dragon when he's despairing at the whole "Oppai Dragon" thing.
  • "No. Just... No" Reaction: Harry, when Lash finally tells him that Sona and Tsubasa are into him.
  • Nosebleed: Harry's Attractive Bent-Gender form gave Tsubasa one.
  • No Sense of Humor: Discussed. Harry jokes that Sona is this, but she's actually more of The Comically Serious. Especially around him.
    Harry: [mock plaintively] Why have you declared all fun your enemy, Sona? Did fun do something to you in the past? What is the source of this crusade?
    Sona: [frowns a little] I have fun. It's just my definition of fun involves far less rampant violation of rules, courtesy, common sense, and decorum.
    Harry: [beat] I'm trying to equate the definition you just provided to any objective definition of the word we're talking about. So far, I'm having trouble finding any matches. [yelps] [incredulous] Did you just stomp on my foot?
    Sona: [takes a sip from her tea with utmost dignity] No. That would be ridiculous.
  • Occidental Otaku: Harry gains shades of this as being stuck in Japan makes things like anime easier to get a hold of than his usual fair. The fact that he's no longer Walking Techbane helps, since he can access the internet now.
  • Oh, Crap!: Harry and Lash's reaction when they realize just how big Great Red is.
  • Omniglot: Devil have Languages, like in D×D canon. Lash tops this by giving Harry the ability to not only speak any language, but also read and write them.
  • Once Done, Never Forgotten: Harry suspects that Lash won't ever let go that the Winter Mantle made him plan on forcing himself on Sona while roughly grabbing her by the hair.
    Lash: [laughs] I didn't think you'd take my comment so seriously. Harry Dresden, have we perhaps found a fetish for you after all?
    Harry: [sighs] I am never going to live this down, am I?
  • One Head Taller: Harry and Sona. It's one of the reasons why she reminds him of Murphy so much, and why she tends to aim for the shin when angry at him.
  • Our Demons Are Different: There are massive differences between demons from Dresden verse and D×D verse. For one, Dresden's demons only care about mortal business generally because of hunger or need of terrifying them. The D×D demons (or rather, devils) though act like your normal, everyday people (Most of them anyway). This is why Harry acts with such hostility to the Student Council when he firsts learns what they are.
  • Out-Gambitted: In the unpublished fourth chapter, Tsubaki tries to play The Gadfly at Harry's expense by interrupting Sona and Tsubasa's bickering with the promise of Harry's treating them to udon at a new place he knows. Harry turns the tables on her by revealing that he actually knew of one — he'd kept an eye open for those because of the bribing potential — and manages to get Tsubaki stuck finishing the Student Council's pending chores for the day.
    Oh ho. So that was Tsubaki's plan? To interrupt their argument with promises of Udon, only for the revelation that I was in fact Udonless to unite the warring factions against me, all while she sat back and got to continue enjoying the spectacle, all the while?
    Clever, but not clever enough, little baby devil.
  • Person as Verb: Harry once wondered if Issei's life is "starting to take a turn for the Dresden" when he discussed the circumstances of his death with Azazel.
  • Poor Communication Kills:
    • Harry threatens the Kuoh Student Council because he's used to much less friendly supernatural beings and the fact that devils where he comes from are very different beings. Once the matter is cleared up he formally apologizes and works alongside of them.
    • The Hero Faction wants to slay Great Red to prove humanity's power to all the supernatural factions, without knowing that he fulfills a VERY important function to reality as a whole.
  • Punctuated! For! Emphasis!: Harry once refuted Azazel by repeating the same three words at him, which were really all the words needed to be said, given the context.
    Azazel: Now, now, "Fire and Ice"! No reason to get touchy. I mean, have I ever really done anything bad enough to deserve an attitude like that?
    Harry: Three. Hundred. Ises.
    Azazel: Now, now. It all worked out in the end. Why linger on things which ended up fine anyway?
    Harry: Three. Hundred. Ises. Not just three hundred Ise, but three hundred Ises with ramped up libidos. Think about that. Reflect on your sins.
  • Recursive Fanfiction: Beyond the Outer Gates Lies... A High School Library?, a spin-off that started when a reader suggested Kusaka Reya join Harry's list of admirers, and Gabriel Blessing challenged him to write it. The Continuation Fic has three times the word count of the original one as of chapter 77.
  • Required Secondary Powers: Harry is a bit flummoxed by how many Forbidden Valor View has with its time-stopping power.
  • Rubber Face: Sona's go-to admonishment when Harry's smartassery or self-endangerment gets too far. He's completely caught off guard by it the first few times because he didn't know how to respond to roughhousing like that from a girl. He soon settles on messing up with her hairdo as a proportional response. Their childish antics almost leads to their First Kiss, but Saji's voice snapped them out of it.
  • Running Gag:
    • Harry has Lash making him change languages mid-conversation just to see how long it takes for his Omniglot Devil friends to pick up on it.
    • Lash teasing Harry that he could have a fetish for pulling his partners' hair during sex, followed by his denials or by pretending he didn't hear her.
  • Sarcasm-Blind: Let's just say that Asia and Harry's sense of humor simply don't mix.
  • Scars Are Forever: Despite Harry reverting to his adolescence, all his scars from a life of battles remained the same. His friends only knew about the ones on his face until Azazel's gender-bending gun temporarily turned him into a very buxom young woman whose shirt suddenly could barely cover "her" front.
  • Screw This, I'm Out of Here!: Harry reaches this point at the end of the fight with Kokabiel, where it just gets ridiculous. Lash has to point out that they're still stuck in Bizarro World, no matter how much Harry wants to leave.
  • Seen It All: Harry and Lash certainly think so. So, God being dead is certainly a Wham Line for them.
  • Shipper on Deck:
    • Lash heartily encourages Harry to pursue a relationship with his female admirers, and, in the continuation, cheers him on whenever he finds himself in an intimate moment with one of them.
    • Tsubaki supports Harry/Sona because their Uptight Loves Wild interplay helps her to relax and smile more.
  • Shipper with an Agenda: Momo and Ruruko like the idea of Harry and Sona getting together because they're both interested in Saji, who has an obvious crush on the Student Council President.
  • Sitcom Arch-Nemesis: Downplayed. Despite becoming a Shipper on Deck for Sona and Harry, Tsubaki didn't quite let go the times Harry was his typical impudent, snarky self with them and occasionally snipes back at him when she gets the chance. For example, it's her verbal jab at the recently gender-bent wizard what finally gets Harry to seek revenge for the embarrassing incident.
  • Skewed Priorities: Harry can't wrap his head around the fact Issei's Love Interests don't even bat an eye when Akeno gives him a Marshmallow Hell, yet they got angry when she collected his promise to take her on a date.
    Harry: [narrating] And, strangely enough, the way every girl with a claim on the boy suddenly went from relaxed to passively hostile. They could stand physical molestation, but they couldn't handle a date?
    Freaking teenagers.
    And oh god, I was one of them now.
    • Similarly, during the Gender Bender story, the fact that Xenovia, Irina and Koneko are more interested in why female!Harry has a bigger bust than Akeno than in their current situation leaves Harry baffled.
  • Smug Snake: Raynare. It is very satisfying for the reader when Harry kicks her around and talks her down right after she attacks Issei.
  • Snark-to-Snark Combat: Harry and Sirzechs engage in a low key, friendly version. Harry has his title as the "Smartest Ass in the Room" to defend after all.
  • Spotting the Thread: Sona didn't buy Harry's Metaphorically True explanation that the Winter Mantle is simply a self-enhancement technique. She reasoned that if that's really the case, then he would have used it when a trio of Muggles gave him a shinner before.
  • Squishy Wizard: Harry, self-admittedly, though the Mantle circumvents this somewhat.
  • Stalking Is Funny If It Is Female After Male: Lampshaded when Harry meets the Hero Faction:
    Harry: Charmed. I'm…
    Georg: Harry Dresden. [smiles slightly] I know. I've had my eye one you for a bit. I'm happy to finally have the chance to meet you in person.
    Harry: Great. A stalker. And it didn't even have the good graces of being a hot, overeager, sexually aggressive cheerleader. Why can't I ever get the good kind of stalker?
    Siegfried: Jeanne. What would it take to convince you to put on a cheerleader outfit? I think it might greatly influence the outcome of this meeting.
    Jeanne: Sig-kun! [frowns and pouts] How could you think something like that! I'm not a cheerleader!
    Harry: And the fact that she didn't deny any of the other qualifiers has perked my interest.
    Jeanne: [blushes and pouts]
  • The Tell: Sona adjusts her glasses when she's planning something. Tsubasa twice calls her out on it because she can guess from the context that it's got something to do with her romantic pursuit of their common Love Interest.
  • Tempting Fate: Harry's "Wizards never get chicks, after all," and Sona's "Dresden-kun, I am not, nor ever will be, interested in you romantically."
  • Those Two Guys: Like in D×D canon, there's Matsuda and Motohama, Issei's perverted friends. In the continuation fic, they constantly pester Harry for magical aid in peeping on their female classmates. Harry goes out of his way to sabotage their efforts.
  • Through His Stomach: Tsubasa brought Harry lunch boxes after she found out his electricity had been shut off for several weeks, which got Sona to glare at her Rook for it. This is significant because both of the girls' actions tore apart through Harry's denial that Lash had it wrong about their romantic interest in him.
  • Token Human: Harry is mostly Human (if one looks past Lash and the Winter Mantle), and thinks of himself as one; all of the rest of the main characters are Devils, and most of the secondary characters are non-Human.
  • Token Wholesome: Amusingly Inverted. Harry realized after telling his friends in Kuoh about how annoying was to get home and catch Thomas in the middle of an orgy, and getting a roomful of red faces for the anecdote, that he was probably the only non-virgin among them.
  • Trapped in Another World: The gates back to Harry's Earth are closed, and cannot be opened from this side. However, the continuation reveals that two entities can contact their counterparts on the other side in limited ways: Uriel and Santa Claus.
  • Trial Balloon Question: Harry asks how big would be the fallout if the church where Asia was taken hostage in were to… hypothetically… be burned down to a crisp. Koneko fixes him with narrowed eyes and updates her assessment of him from "suspicious" to "definitely suspicious."
  • Troll:
    • Once Harry learns about the Devils' gift of tongues he regularly has Lash switch languages mid-conversation just to see how long it takes them to notice.
    • Later, after Issei finds out about Lash, and how she can manifest herself as a pretty woman, Harry pretends that she's taking her clothes off to get Issei to freak out, and Asia to try to get his attention by stripping. Lash notes that normally she'd be mad at him for lying about what she's doing, but approves of the results.
  • True Companions: How Harry and Issei see each other. It's pretty telling that Winter Harry didn't see Issei as threat, but as a "pack mate, a comrade [he] could rely on in the hunt."
  • Unable to Support a Wife: Referenced by Harry as a reason Sona and Tsubasa shouldn't be interested in him.
    Harry: I can barely make rent half the time and I'm having trouble making enough money to even pay my bills, so it's not like I would be able to treat either of you to dates or things like that.
  • Undead Tax Exemption: Thoroughly Averted. Appearing all of a sudden in a new world lacking any evidence he ever existed meant that Harry had to wade through "enough paperwork to deforest a significant portion of the Congo" to get the Japanese government to grant him citizenship. And a similar additional amount to become an Emancipated Child in order to keep himself out of the foster care system, which was bad enough for him the first time in his original world.
  • Unequal Pairing: Defied. Sona and Tsubasa don't let the latter's subordinate position to the former as a member of her Peerage interfere with their love lives, opting for treating each other as equals when it comes to their romantic pursue of Harry. He learned to pay attention to their shifts to First-Name Basis and back to tell when they're going to talk about romance or dangerous supernatural business, respectively. Guess which one worries our Socially Awkward Hero the most.
  • Unwanted Harem: Though a more fitting term would probably be reluctant harem. Harry is romantically drawn to all his admirers but feels conflicted about becoming involved with them, due to their age and his difficult relationship history.
  • Unwitting Pawn: Harry considers the possibility that the Outsiders are manipulating the Hero Faction in order to try and gain a foothold in the D×D reality by killing Great Red, the main thing keeping them out.
  • Uptight Loves Wild: As it turns out, Sona and Harry. Their interactions begin when the serious and responsible Student Council President of Kuoh Academy tries to get the snarky mistaken-for-Delinquent New Transfer Student with a problem with authority and no respect for the dress code to behave.
  • Villainous BSoD: Raynare, after Harry Soulgazes her. She goes from haughty to begging that Harry stay away from her.
  • Walking Techbane: The fact that he's not this anymore is Harry's first clue that despite appearances he's a long way from home.
  • Waxing Lyrical: Harry tried to be polite to Rias' brother, as it's his policy for his friends' family, but he couldn't help but somehow mouth off to the guy whose job description is "The Devil". He never saw it coming that Sirzechs would be a fellow Pop-Cultured Badass.
    Sirzechs: So this is the infamous Dresden Harry. As my father said, it is a pleasure.
    Harry: Pleased to meet you. Hope you guessed my name.
    Sirzechs: Well, now you've met me. Have some courtesy, have some sympathy, have some taste.
    Harry: [beat] My god, my minister was right all along. Rock and Roll really is the devil's music.
  • Weak, but Skilled: Harry is far from a powerhouse by High School D×D's standards, yet remains a dangerous opponent to have because he's used to hit above his weight class. His varied skill set, his unique-to-Bizarro-World magic style, his Combat Pragmatist and Muggles Do It Better tendencies, his acquired caution to always look at the big picture and outplay his enemies, his Properly Paranoid mentality that makes him to always look for ways the Finagle's Law could screw him over yet again, his BS-ing skills and a long etcetera make Harry a much more effective combatant than he has any right to be, Power Level-wise.
  • Weirdness Magnet: Harry lampshades his status as one when expressing his surprise at not getting involved with the Riser mess at any point, given how he tends to get drawn into every major supernatural mess that happens anywhere near him, and when Sona offers him a contract, reminding her how often he gets into trouble. In the continuation Azazel blatantly refers to both him and Issei as trouble magnets.
  • Weirdness Censor: When Harry accidentally reveals that his magic doesn’t conform to Bizarro World’s rules, Sona, Rias, and Issei simply speculate that Harry is just so naturally talented at magic that he doesn’t need to pay attention to traditional rules. Apparently it’s not unheard of, just super rare.
  • Well-Intentioned Extremist: The Hero Faction, made up of the descendants and reincarnations of great heroes like Hercules, Joan of Arc, Sigfried and so on. Their goal is to give humanity a position of power in the world, but unfortunately, they also want to kill Great Red, who is basically the Big Good of the setting, and the worlds biggest defender against the Outsiders. They want to kill him mainly because he's a dangerously powerful dragon, despite the fact that he's almost never out of the Dimensional Void. They also dislike supernatural beings overall, regardless of alignment, despite their Chaos Brigade affiliation, and are perfectly willing to put civilian humans in danger if it means achieving their goals. They are even worse in the continuation, where Harry learns they brainwash members so they can't reveal anything about the group, and Cao Cao even considers young Heroes their property, given his words about Alice White.
  • What Are You: Poor, poor Raynare.
  • Why Can't I Hate You?: Saji dislikes Harry on principle because of Sona's interest in him. However, he can't bring himself to actually hate his romantic rival because he can tell Harry has one important thing in common with most Resurrected Devils like himself.
  • Wrong Context Magic:
    • Harry's usual magic is derived from his willpower and belief (and makes him Walking Techbane in his own world, but not in the world he's currently in), while their system of (normal) magic uses what amounts to rituals in his, where he just has to put in the power and not the belief, so it doesn't need him trying to micromanage it, and can do things the Laws of Magic of Dresden's world forbids with no risk of corruption. In addition, Soulfire isn't something native to their world so it's not as easy to deal with.
    • Things like Rias' Power of Destruction and Sacred Gears are this to Harry and Lash, which excites the latter to discover something new.
  • Your Approval Fills Me with Shame: Harry knew he took a joke too far when Lash, Manipulative Bitch extraordinaire, congratulated him for the all potential chaos and mayhem that his carefully worded comments on the Oppai Dragon Show Within a Show were likely to bring.
  • You Remind Me of X: Sona Sitri's by-the-book attitude and shortness reminds Harry a lot of Karin Murphy at the beginning of their friendship. He acts like a total smartass to Sona both out of nostalgia and in an effort "to get her to loosen up a bit as a favor to the Murphy of old."

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