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Exhibit A of a goofy pervy high school student.

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     Anime 
Season One
  • Episode 2 had a moment where Issei is summoned for the first time. He steps into the transport circle, the music gets all suspenseful and dramatic, and then the music just stops as rage summoning circle his fizzles out around him since he can't teleport. There's a Beat, then Issei's stunned reaction.
    Issei: "The fuck?"
    • Then he has to go to the summon by bike.
  • Episode 3. Nipple lasers. That is all.
  • Episode 4 had Freed's "For real?" face when Issei promotes himself to Rook.
    • The Dub actually makes it funnier with Freed nonchalantly going "Yeah, I'm fucked."
  • Episode 7:
    • Issei gives Saji a very firm handshake after he enthusiastically shakes hands with Asia, threatening that if he makes any more moves, he'll cut off his nuts and feed them to him - at which point Saji retaliates, gaining the upper hand as they 'argue', with both ending in a stalemate. Rias notes "This is embarrassing", which Sona agrees with.
    • Issei suffers a Groin Attack during the dodgeball game and gets treated by Asia's Healing Hands. And after that Rias says they can't let Issei's death be in vain. Although considering what happened to Issei in the light novels...
  • Episode 8:
    • To an understandably furious Koneko.
    Issei: So... come here often?
    • Issei accidentally walks in on Asia when she's in the shower, and he's the one that Screams Like a Little Girl
    • It's even funnier when you realize it was because Asia briefly glanced at his groin. And then he promptly lampshades the moment with "Wait, why am I screaming (like a girl)!?", before trying to leave.
    • Even funnier in the anime when Asia asks Issei to join her and then Issei's mother walks in on them bathing and runs out yelling "Honey! We're going to be seeing our grandchild soon!" (Note that at this point in the story, Asia is Issei's bridal candidate by Japanese custom.)
    • When Riser's peerage enters the scene, Issei starts crying in jealousy of Riser's harem. Riser then asks Rias why her servant is crying.
      • In the dub, Issei even copies Riser's Verbal Tic of talking in third person.
      Issei: Issei hates him so much… Why can't I be this guy?!
      Riser: My dear, why is your servant looking at me and weeping uncontrollably?
  • Episode 9:
    • Asia trying to read from her bible knowing it will cause her terrible pain and doing so anyway, repeatedly.
    • Same episode of the dub, Kiba walks past the struggling Issei with a wonderfully blithe "On your right", causing Issei to go "Seriously!?" note 
    • Kiba, who is carrying the same size pack as Issei is then followed by Koneko who is carrying what appears to be a large tarp full of supplies that is many times bigger than her, hell it'd dwarf any of the other characters.
    • When Rias suggests it's time for them to have an after-dinner bath, she tells Issei he can join them if the other girls agree. Akeno and Asia agree. Koneko on the other hand states that she'd rather die, and if Issei peeks she'll kill him.

Season Two

  • Episode 1: Just in the first minute, we already have Issei waking up to see that Rias has joined him in his bed, naked. When she wakes up, she contemplates whether or not to indulge Issei with something sexy. Of course, Asia has to interrupt them to remind them of morning training. When she opens the door to see a nude Rias in bed with Issei, she decides to strip off her clothes as well, much to Issei's shock.
  • Episode 2: Issei wakes up in the morning to find that Rias and Asia have used one of his arms each as a pillow, while sleeping naked in his bed.
    • After Rias and Asia have left Issei's room to prepare breakfast, Issei has an Imagine Spot where he's the Harem King, and Rias and Asia beg him to have them be the one he sleeps with first. They go as far as to do rock paper scissors while topless.
  • Episode 3: During Issei's duel with Irina, he's of course inwardly excited about using Dress Break on her, complete with imaginings of such. Irina's creeped out by his expression, before Koneko warns her about said ability, much to her shock:
    Irina: What!? Their clothes!?
    Issei: (slightly incensed) Koneko! Why are you giving my secrets away to the enemy!?
    Koneko: (flatly) Because you are the enemy to all women.
    Issei: (almost comically-depressed; to himself) Sometimes the things you say really hurt.
  • Episode 4: Saji getting spanked by Sona, and then Rias follows her example with Issei, and later Kiba in Episode 6 (offscreen).
    • But speaking of Kiba, his reaction when he learns about this result:
      Rias: (with dissonant cheerfulness) [Your punishment is] one thousand spankings.
      Kiba: (voice cracking) What!?
      Issei: Haha! This is great; good luck taking it pretty boy!
      Kiba: Gah... s-shut up, Issei!
  • Xenovia praying to God after becoming a Devil. The results are... predictable.
    Koneko: Anyone else getting Deja Vu?
    • And before that, when she practiced "how to be a normal teenage girl", in both versions (though for different reasons):
      (Subbed)
      Xenovia: (Voice several pitches higher than her usual coarse-and-masculine baritone) Let's get along, 'kay, Issei-kun!
      Issei: That cutesey voice does NOT suit you!
      Xenovia: (Switches straight back to her normal-unfeminine voice) I know, I tried to copy Irina, and it was SO difficult.
      (Dubbed)
      Xenovia: (barely any different in inflection/volume) It looks like we get to work together, Issei.
      Issei: Don't try to sound cute while making that face!
      Xenovia: My goal was to mimic Irina, but I guess I just didn't quite get it right.
  • In Episode 7, after Azazel reveals his identity to Issei, the latter is more pissed that because of the former, he was unable to suck Rias's breasts, as opposed to getting killed a season and a half ago.
  • Xenovia trying to get Issei to sleep with her and being completely stone faced about it.
    • And she continues these antics next episode, first by holding up several condoms in class while asking Issei for some "practice".
  • Serafall's antics during Class Observation Day (and subsequently, Sona just losing it out of sheer embarrassment).
    Serafall: No Sona-chan, no life!
    • The dub version has this example of Serafall going completely Motor Mouth and telling everyone what she really feels:
      Serafall: You should run into my arms and tell me how much you missed me! And-then-I'll-say-oh-Sona-I-missed-you-tooandthenI'llgiveyouabigfatkissandyou'dkissmebackandthatwouldleadtogirlongirlactionwouldn'tthatbehoooooot? XD
  • During that same episode, using a block of modeling clay while running on autopilot, Issei manages to make a sculpture of Rias. Naked, with only Godiva Hair covering the important bits. And then it sparks off a bidding war as Rias' fans clamor to buy it off him.
  • Koneko trying to toughen up Gasper by offering him some Garlic... he's a vampire, mind you. The sight of her chasing him all the while chanting "Here Here Here" in her usual deadpan tone is a side-splitting sight. The quick exchange between Saji and Issei which directly follows is also a gutbuster.
    Saji: Another pretty blonde?
    Issei: Pretty, but still a dude, man.
    Saji: [on his knees, completely distraught] ...A dude?! Why... Why have I been forsaken so!?
    Issei: (knowingly) I know dude; we've all been there.
  • Issei's parents getting along with Rias's father and brother, much to their chagrin.
  • In episode 10, when Rias and Akeno take turns shoving Issei's face into their breasts, Issei feels that he's in paradise. Then Asia catches them in the act, and he quickly decides "Maybe not." in the English dub.
    • The next morning, Issei wakes up to find that not only did Rias, Akeno, and Asia decide to share his bed, but they had also completely disrobed, leading him to scream in shock.
  • During the conference, Azazel asks for Issei's opinion (who says he can't make that serious an opinion so quickly). So he puts it in Layman's Terms: if there's peace, he can have sex with Rias every day; if there's war, he can't... all while Rias is present beside Issei.
    • And needless to say, Rias's reactions to this are pretty funny as well. In the dub she even says "H-Hey, I'm right here!"
    • Issei only catches himself yelling enthusiastically about having sex with Rias when Kiba points out Sirzechs note  is in the room. Naturally, Issei freezes in terror, but the true crowning moment is a reverse angle showing Sirzechs hiding behind his chair trying desperately not to laugh.
    • He also uses a similar analogy in order to make Issei power up in his fight against Vali (Half Dimension reduces everything affected by it in half, including Rias' breast size). It works so well he lampshades it in both versions.
      (Subbed) What the heck? Seriously? His powers skyrocketed just by the thought of his mistress' tits shrinking.
      (Dubbed) Hahahahahaha! This fight is hilarious! His power increases this much just to keep his master's chest from getting smaller.
    • Plus the exchange just before that (dub dialog):
      Issei: DON’T FUCK WITH MEEEE! (BOOST!) Rias' boobs are perfect and I won't let you reduce them!
      Vali: Wait, what?
      Issei: You Monster!! (BOOST!) You're pure evil! (BOOST!) I will never forgive you for this! (BOOSTBOOSTBOOSTBOOSTBOOSTBOOSTBOOSTBOOST-!)
  • In the same episode, when Gasper has frozen his captors in time with his newfound powers, Issei wasted no time at all Dress-Breaking them, and was about to pounce on and grope the helpless villains... when Rias stops him with a mild-looking Megaton Punch to the head.
    Rias: Down, boy.
    Issei: (resigned) Right, I'm down.

Season Three

  • Episode One: Issei's absolutely gobsmacked reaction when he discovers that his house has been renovated to a huge mansion, overnight.
    • Before that realization, Rias and Akeno have a pillow fight over Issei.
      • And before that, Issei has an Erotic Dream where Rias, Akeno, Asia, Koneko, and Xenovia are topless, and invite him to grope their breasts, complete with their accurate personalities.
    • Issei's parents seem to adapt to suddenly living in a mansion over night very well.
  • Episode Three: Kuroka describes Issei as "The breast-lover who defeated Vali". Issei has the audacity to be offended by being defined that way for a second, until he remembers that's pretty much exactly how it went down. For the dub, he's not that offended, and is damn proud of defeating Vali, but likes to consider himself more of a connoisseur.
    • In the dub version, Tannin's plan for fighting Kuroka and Bikou:
      Tannin: While I slap this monkey around, you guys pound that pussy!
    • Also dub, after Issei achieves Balance Breaker:
      Ddraig: Congratulations partner, but I'm not looking forward to what you're gonna use this hand for when we're done here...
  • Episode Four's dub gives us a few mild moments, courtesy of Loki no less:
    Saji: You underestimated us - big mistake.
    Loki: The only thing big is your talk, little boy.
    Saji: You need to work on your comebacks, man; they're pretty lame.
    Loki: Noted. (tries to blast Saji)
  • Loki's reaction after Koneko and Akeno have resolved (or started to face) their internal issues.
    Loki: I smell teenage angst. How disgustingly cliche.
  • Issei can't resist cracking the dumbest joke he can think of when he's making a run for Mjolnir.
  • Episode Five: The other female members of the Occult Research Club (and Gasper) spying on Issei's date with Akeno in hilariously obvious disguises. Then there's Rias' line in the dub when they notice:
    Rias: They clocked us somehow!
  • Episode Six: Ddraig's (over)reaction to Issei's newest nickname as the 'Breast Dragon Emperor' - no matter which version, it's hard not to crack at the utter bawling this dragon's been reduced to.
    Ddraig: I'm one of the two Heavenly Dragons! The name 'Red Dragon Emperor' used to strike fear into the hearts of millions!
    Issei: Look, I'm embarrassed too, okay-
    Ddraig: But now I'm the Breast Dragon Emperor! ALL HAIL GRABBIN' DRAGON!
    • Not to mention the crew's reactions to videos of Issei powering up after poking Rias's boobs. We get a pan shot of Gasper, Akeno and Rias; Gasper is thrilled, Akeno is mildly amused, and Rias is staring in slack-jawed mortification. Issei's final reaction of "Just kill me now..." before the ad break is the crowner.
  • The dub turns Issei, Xenovia, and Asia's encounter in the gym shed into an absolute hurricane of jokes. First, Xenovia has heard of a "devil's threesome" (likely from Issei's friends, who previously used the term to describe a two-boys-one-girl threesome), thinks it means a threesome between devils, and wants to try it out. When Asia protests, Xenovia says that a threesome will help her and Issei in the three-legged race, because "it's the rule of threes", despite Issei's protest that none of this is how that works. Finally, Irina bursts in to ruin the moment, except...
    Irina: You should do that in bed! This place is filthy, who knows what diseases you could catch here?!
    Issei: ...Valid.
  • Sexy See-through outfits, give me sight beyond sight!
  • Episode Eight's dub added in one of the most unexpected one-liners for this series ever:
    Xenovia: (dual-wielding Durandal and Ascalon, alight with holy power) With your powers combined, I will smite my enemies! I have the strength, because friendship is magic!
    *destroys Diodora's Rooks*
    • Then, Kiba's reaction to Rias and Akeno's girl fight from the sidelines?
    • Issei's reaction to Koneko's plan (entice Akeno by offering a date with him) actually working. For the subbed version, it's your usual comical Big "WHAT?!", whereas dubbed, it’s a Flat "What" dragged out out of pure disbelief.
    • The entire argument between Rias and Akeno is a gutbuster by itself. Rias, offended by how Akeno is one-upping her simply by being told she can go on a date with Issei if she defeats Diodora's mooks, gets one back by telling her that Issei gets more intimate with her in bed. Akeno, on her part, says that Rias is just jealous of how she's getting a date with Issei before she does. Diodora's Queen calls both of them out and tells them to focus on battling instead of arguing over their object of affection, but Rias and Akeno both tell her to mind her own business and obliterate her with a combined shot of magic.
    • Diodora gets nicknamed "Dildora Asstomouth" and "Diodora the Explorer" by Issei and Freed respectively.
  • Episode Twelve: Rossweisse happily takes up Rias' offer of becoming her second Rook, mostly for financial reasons, but also to get revenge against Odin. For the sub, she merely says she'll never forgive him next time they meet, but the dub?
    Rossweisse: (internally) This is a dream come true! You can take your crummy job and shove it, you prune-faced old pervert!

Season Four

  • The ending song of Season Four, while cramming in as much fanservice as it possibly can as always, is actually hilarious when you realize that the lyrics are about a Type A Tsundere justifying why she's a tsun-tsun.
  • Episode 0 of Season Four re-rails the plot be retelling Issei's recovery from Juggernaut Drive exactly as it happened in the novels... Which means we're treated to a fully-realized OP for the Oppai Dragon Show, complete with In-Universe credits. Which is hilarious enough on its own, but midway through there's a reaction shot from Rias. You can just see her slowly dying on the inside.
  • In Episode 2, Rossweisse battles with Issei over him going into the girls' locker room. She gets stripped of her clothes by his Dress Break but she doesn't realize it until a few seconds later. Later, when she's trying to call Issei out on his actions, the dub has this example:
    Rossweisse: Doesn't your sex drive have any kind of "off" button? Bueller? Hello, McFly?
  • Episode 3 has Xenovia and Irina invoke a Moment Killer on Issei and Asia when they kiss. What's Xenovia's response?
    Xenovia: Wow! A PG-13 moment right under our noses. How much longer until you two kick things up to Rated R, huh? Or is it M for Mature?
  • Episode 6:
    • The entire culmination of all the mysterious business surrounding Issei's 'potential' in the previous episodes is comedy gold. But special mention goes to:
      • The way that Elsha, previous host of the Boosted Gear, talks all of this up with full on epic Serious Business treatment even after the reveal that Issei's power up this time is triggered by... Poking nipples. Again.
      • Issei's potential summoning a whole bunch of boob zombie spirits who look like they're going to attack, making it seem like they are the special new attack Issei has unlocked, only for them to mill around a bit while moaning 'boobies', zombie style, and then sorta just peace out.
      • Rias descending out of the sky, exchanging a few words with Issei, getting her breasts poked with a resigned sigh... And then ascending into the sky in a beam of light while having an Immodest Orgasm. All in the span of three minutes. Also, Issei's dub reaction when she suddenly ascends into the sky:
        Issei: (bewildered) ...You're welcome?
      • Ddraig's reaction when Issei is about to poke Rias' nipples.
        Issei: (fired up): Are you ready to do this, Ddraig?
        Ddraig: *inconsolable weeping*
      • Cao Cao's blasé reaction to all of it. Particularly in the English dub.
        Cao Cao: Ok. Sure. Makes sense.
      • Elsha building up the 'few words of advice' that Belzard, the strongest person ever to wield the Boosted Gear, is going to say now that the two of them are finally free to pass to the afterlife, only for him to sing part of the lyrics to the Oppai Dragon song and then give a goofy smirk.
    • Near the end of Episode 6, Azazel remarks about Kunou inheriting Yasaka's looks, much to Issei's chagrin, who boldly exclaims he'd rather go for the mature kitsune... and is promptly gut-punched by Koneko.
      Issei: (pained) What'd I say...?
      Koneko: You know, cock muppet.
    • Koneko also learns from Azazel that Ravel is going to be a transfer student at Kuoh Academy. Her reaction?
      Koneko: She can suck it.
  • The beginning of Episode 7, where the club is participating in a play of the Oppai Dragon/Grabbing Dragon show. Everyone's at least trying to sound authentic, except for...
    Rias: Help. Someone save me, like a hero- no, better, the Grabbing Dragon. (beat; Rias gives off a 'I can't believe I'm actually doing this' sigh)
  • This exchange between Koneko and Ravel in the dub of episode 7.
    Koneko: Besides, cats love fried chicken.
    Ravel: Did you just call me a chicken?!
    Koneko: Yeah, so?
    Ravel: Ugh! How dare you! I can't believe you have the audacity to insult a member of the Phenex family!
    Koneko: You've only been in this school for one week and you're already causing a bunch of problems for the prez and Issei, so all things considered, you're lucky I stopped at "fried chicken."
    Ravel: Well, better a fried chicken than a little pussy!
    Koneko: Wish granted.
  • Episode 8: In the dub, Koneko refers to Ravel as "Cuntucky Fried Chicken".
  • Episode 9: Right after Asia, Akeno, and Koneko get Issei out of his Heroic BSoD, Xenovia mistakes their Intimate Healing for something else, prompting her to strip off her clothes to join them, followed shortly after by Irina.
  • Episode 10: Coriana keeps Issei from being able to fight by doing a striptease. Issei's too Distracted by the Sexy to move until Coriana begins removing her panties before her bra. This is what causes Issei to oneshot her.

Other

  • "Why does everyone we fight have all these wiggly appendages?"
  • When Freed...does pretty much anything, really. Twisted as the guy is, he's a joy to watch. Evil Is Hammy indeed.
    • Of all the ways he can pronounce Excalibur, he chooses this one instead.
    • Freed calling Koneko "little'', and gets benches thrown at him.
      • His not so manly "Owie" after being hit with a bench
  • Any time Koneko performs some feat of Super-Strength accompanied with a tiny little "Eh." (Subbed version only)
  • The Oppai Dragon Song, now De Fictionalized and featured in the Season 3 PV, sang by Issei's VA.
  • The very last bit of the Season 3 ending credits, where Issei is surprised in bed by the entire female portion of The Occult Research Club. They're all red in the face, everyone save Issei, Irina, and Rossweisse are completely naked, then everyone climbs into bed with Issei (possibly with 'more' involved). However, two reactions stand out in the situation:
  • The third season OVA adapts Ravel coming to the Occult Research Club, for help with her brother, but this also means it animates the famous hot springs moment. Rias, Asia, Akeno, and Xenovia aren't embarrassed about Issei suddenly landing about them while naked; Koneko, Irina, and especially Rosseweisse are, naturally; Ravel... well, after the shock (and a perverted comment from Issei on her growing body), she embarrassingly explodes with Phoenix fire.
  • Koneko being turned from The Stoic to perverted molester in one of the special episodes.
  • Basically happens whenever Issei is being a Deadpan Snarker.

     Light Novel (Main Story) 
Volume One
  • In chapter 2 Issei suffers a Rhetorical Question Blunder when he fails to use the magical diagram after being summoned and Rias tells him to travel on foot. He asks "What kind of Devil shows up on a bicycle after being summoned?". Koneko points at him in response.

Volume Two

  • Chapter 16.5: "I HAVE ABSOLUTELY NO DERE!"
  • The reactions of Issei's comrades to Dress Break. Koneko tells him to stay far away from her, and Kiba actually apologizes to the other team.
  • Issei, having just shown up at the wedding hall, announces that he’s here to take her back and that “BUCHOU’S VIRGINITY IS MINE!!!” Shocking everyone present.

Volume Three

  • Freed shows up in the middle of the night to taunt Issei, Rias, and Asia, who were sleeping in the same bed. He then admits that he's bad at reading the atmosphere. Though the rest of the scene becomes less funny once Kokabiel shows up.
  • Kiba gets spanked by Rias with Issei laughing throughout the whole time.
    • Though that might be because Issei got spanked earlier....
  • During the fight with Kokabiel, Issei says that he won't let him destroy the town before he becomes a harem king. Kokabiel laughs and offers to let him sleep with a bunch of the fallen angel girls. Issei is so shocked Rias has to snap him out of it with a slightly jealous reprimand.

Volume Four

  • Issei is losing the fight with Vali by a large margin. In an attempt to rile Issei up, Azazel mentions that Vali can halve peoples breasts. Three seconds later Vali is spitting up blood and struggling to stay in the air.

Volume Five

  • The Sitri team's reactions to Billingual.

Volume Six

  • Volume 6, Chapter 2: Vali and Bikou with Issei look at Mil-tan. Their reaction? They think he's a nekomata using senjuutsu to hide his form. Issei's first-person tsukkomis are priceless.
    • Bikou trying hard not to laugh too much by the events of getting Issei out of Juggernaut Drive. And the reason why Rias' Embarrassing Nickname "Switch Princess" came to be.
    • Vali's Rhetorical Question Blunder where he asks Bikou if Rias' breasts are a control switch for Issei in which Bikou bursts out laughing so hard.

Volume Seven

  • When Issei and Akeno go on their date, the rest of the club is spying on them. Rias is wearing a hat and sunglasses, Asia is crying through her sunglasses, Koneko has a luchador mask, Gaspar is wearing his paper bag, and Kiba is waving hello in his normal clothes.
  • Albion refusing to affiliate himself with Ddraig due to his new status as the “Chi Chiryutei” (or Oppai dragon, or whatever it’s translated into)
  • Then the two Heavenly dragons breaking down and crying at the fact that Ddraig is now referred to as the Breast Dragon and Albion being the Butt Dragon.
  • Issei trying to talk to Akeno's breasts instead accidentally summons the freaking god of breasts! He then asks Taninim as to whether a breast god exists. Everyone stops fighting and looks at Issei like he's going crazy. The kicker as well was when Ddraig backed him up and everyone thinks Ddraig has lost it as well.

Volume Eight

  • Throughout the novel Issei channels his inner Shinpachi

Volume Nine

  • Volume 9: The reason why there are a lot of molesters in the streets? It's because of Issei opening a box way back in the beginning of the Volume.
    • Three words: Breast Lover Zombies.
    • Rossweisse vomiting while fighting off against Heracles because she's still affected by the alcohol she drank earlier in the day.

Volume Ten

  • The long awaited confession of Issei to Rias and they're about to kiss. Suddenly, they get hit with a Moment Killer when the door of the clubroom opened and everyone in the group was watching it.

Volume Eleven

  • Volume 11 shows us what happens when Issei uses Gift on Rias' breasts. It replenishes his aura at the cost of her breasts shrinking. The kicker? Siegfried makes an Oh, Crap! face!
    • Siegfreed's Oh, Crap! was preceded by Azazel recognizing the conversation as similar to the one Issei had with Tannin in vol 7. Cue Large Ham.
      Azazel: It's heeeeeeerrrreeeee!!! WAHAHAHAHAHAHA.
    • Ophis asks Ddraig if he wants to be the Breast Dragon Emperor instead of the Heavenly Dragon. Cue Ddraig going into another one of his Heroic BSODs.
    • Ddraig needs medicine to calm himself down. One of the most powerful dragons needing medicine just to calm down whenever someone talks about breasts.
      • This is understating it. Ddraig is being treated for clinical depression. You heard that right. A dragon/Transformation Trinket is undergoing psychiatric treatment for clinical depression, including medication and therapy sessions.
    • During the promotion test, the practical portion is revealed to be a duel between two applicants. Issei, being Issei, is worried about how well he'll do and treats it like a life-or-death battle. Five seconds later, he lands one punch and sends the other guy through the wall. Both Akeno and Kiba were cracking up when they heard about it.

Volume Twelve

  • Volume 12: Opfis and Great Red sang the Oppai Dragon theme music. Ddraig was definitely not amused.
    • Issei, in his spirit form, laments at the fact that he can't make out with Rias with his current state.
      • What makes the above even funnier is that Sairaorg predicted this exactly as his reasoning behind why Issei would come Back from the Dead.
    • Issei's He's Back! moment. He even has to say "breasts" to let his friends know that he has returned, much to his consternation.
    • Ophis tapping the "ground" that she and Issei are on. When asked, all she said was "I'm defeating Great Red."
    • Kiba is greatly annoyed by the fact that Xenovia declares that she'll just power through everything and that Kiba should be the only technique type. Kiba's First-Person Smartass commentaries are hilarious.
    • And everyone's (From the past users of the Boosted Gear to Great Red itself) last words to Issei: "Zoom, Zoom, Iyaaan~" note 

Volume Fourteen

  • Volume 14: Poor Issei, he can't even sleep on his own bed any more thanks to the girls sleeping on it. Xenovia kicks him out while asleep.
    • Ophis sleeping at Issei's bed like a dead person in a coffin.
    • Also from 14: Issei's lap has escalated into a battleground with Koneko and Ravel vying for complete control and ending with Koneko and Ravel on Issei's left and right thighs, respectively. It began with Koneko acting like it is her territory while Issei muses to himself that it must be the cat part of Koneko that makes her want to keep Issei's lap as hers.
    • Xenovia is having a hard time mastering all of the Excaliburs due to being a 'power-idiot', as Issei puts it so Irina tells her that she might become the self-proclaimed swordsman. Xenovia doesn't take well to this and retaliates by calling Irina the self-proclaimed angel. Irina is offended and asks Issei to assure her that she is an angel, reasoning that since he's her childhood friend he'll agree. Issei comments that it's easy for him to forget that they really are childhood friends to which Xenovia takes advantage of by calling Irina the self-proclaimed childhood friend, to her chagrin.
    • Okay, the mooks are defeated and the leader summons a big scary dragon thought to be dead. Issei calls on Ddraig for a little help... and then Ddraig speaks, in his normal voice mind you, “onii-chan...who are you?”... turns out issei’s little death episode and the mental stress of being referred to as the “oppai/grabbin’ dragon made him mentally revert into a child
    • Ddraig's He's Back! moment. That is all.
    • Even if he's currently the enemy, Euclid making a lot of commentary with such seriousness is just hilarious.
    • During the first night with Rias, Kiba and Azazel away to negotiate with the Vampires, Akeno mistakenly tempts Issei into making love to her, thinking this is what he usually does with Rias and Asia every night. When she realizes her mistake, she disregards it and continues to seduce him, despite Asia being there to see it happen. Issei then has a Good Angel, Bad Angel moment except from his perspective it's two devils, instead. The first tells him to do it even with Asia watching. The second? It demands him to take Asia as well.

Volume Fifteen

  • Volume 15: Ophis, while sitting on top of Fafnir's head with Rassei sitting on top of her head, saying, "I, with this three-combination, think, can challenge Great-Red."
  • Ddraig refusing to acknowledge Fafnir that Issei nicknamed the Pantsu Dragon King.
  • Xenovia and Irina competing over the right to sit on Issei's lap. Also, Ravel's disappointment of her status as a latecomer and Sister Griselda arrival adds to the humor.
  • Azazel's thoughts that Issei is better off than Vali when comparing the fact that Issei gets three meals a day prepared by his loved ones while Vali's entire team eats nothing but instant food when Le Fay is not around to cook for them. Also, the fact that a certain god-killing wolf is being given cup noodles to eat.
  • Azazel telling Bikou that he's considering adding Vali to the Oppai Dragon show.

Volume Sixteen

  • Fafnir being picky with what he wants and requests that he be presented with Asia's school swimsuit. Luckily for the group, Asia did bring it at per Sona's request who foresaw that coming.
  • Anytime Irina has her wings flickering from angel to fallen angel wings.

Volume Seventeen

Volume Eighteen

  • Issei and Vali watching porn at Issei's house. The end result? Vali can't comprehend porn and Issei has to explain everything about it.
  • Irina's father bringing a gift for Irina from Heaven. The gift? A doorknob that will turn any room into a magical space where angels and devils can safely make babies without the angel falling! Michael actually wants his ace and Issei to have sex! Doubles also as a Heartwarming Moment.
    • Irina's father's declaration to Issei is the kicker.
    • Everyone quickly picking up on the idea of a room designed only for sex being handed over to Issei and deciding that it is potentially one of the most dangerous and terrible things they've ever seen. Then they all start thinking about using it for themselves.
  • After the battle is over Issei figures out how to use his new ability to gain X-Ray Vision. No points for guessing what he intended to use it for.

Volume Twenty

  • While the entire volume is mostly serious, Azazel baiting Lilith with candy just to get past her and go through the door would probably make someone chuckle.

Volume Twenty-One

  • The Volume starts off on a grim note with a flashback to Azazel's first meeting with Vali and an update on the rapidly deteriorating situation of Trihexa's rampage. However, then we learn that Issei is recovering from his recent Heroic RRoD by being soaked in breast milk. And it works.
    • However, when Issei wakes up, he learns there are still some remaining side effects. As a result, he's suffering from Dragon Deficiency: breasts now harm him. He can't say the word, looking at them results in his vision getting blurry (except for Koneko's), and he can't touch or even think about them without experiencing immense pain. And then the Oppai Dragon Song begins playing.
  • Vali attempts to explain that he's Issei's rival to Issei's parents by revealing how he threatened to kill them in order to make Issei fight harder. Awkwardness ensues, but Vali is surprisingly forgiven and the conversation continues, leading Vali to bring up that Issei fought even harder when Rias's bust size was threatened.
  • At the end of the Volume, a re-hospitalized Issei notices that Ophis is in her adult form and his Dragon Deficiency is finally cured. Vali, who is in the same room as Issei, hospitalized, explained to him that the current form Ophis took IS the cost for nerfing his Diabolos Dragon form.

Volume Twenty-Two

  • Grigori developed their own magic ero room doorknob, which Akeno uses to lure Issei into a "special graduation ceremony". However, Rias shows up and starts trying to compete with Akeno, followed shortly afterwards by Ravel and the church trio, who kill the mood as usual, which leads into a discussion about giving everyone else their own ero room, a prospect which both intrigues and terrifies Issei given the antics caused by just one doorknob.
  • At Issei's High-Class Devil promotion ceremony, a famous opera singer comes out and starts singing the Oppai Dragon song. Everyone is confused at such a song being sung at a formal event while Rias's father is moved to tears by the performance.

Volume Twenty-Three

  • The Brave Saints team's ultimate tactic against Issei: trap him in one of Dulio's bubbles and show him a sexy video of Gabriel in Fanservice clothing so he doesn't try to break free.

     Light Novel (Side Story) 
Volume Eight

Volume Thirteen

  • Volume 13: Gasper goes from Cardboard Box Vampire to Cardboard Box Vampire Shogun, and then Cardboard Box Vampire God, and proceeds to change the title of the movie.
    • The entire chapter of Issei SOS.
    • Kiba genderbended himself to tend Issei. The other girls are not amused.
    • Riser's training, which involves a dragon chasing him in the mountains.
    • The Alliance's Sports Festival Event. This is going to be interesting. To wit:
      • The three leaders are just trying to pump up their members and already said members are trying to kill the other two parties.
      • What Issei needs to find in the "item collection race": someone who has a sister-complex. Only two people come to mind and he chooses Sirzechs.
      • Using his Dress Break in the cavalry match thanks to a suggestion by Azazel. Gabriel wins.
      • In vol.13, when he hits almost all the female calvary members with Dress Break during the Sports Festival, he makes the entire male contingent on the Angel's side start wavering.
      • Azazel's "Blazer Shining Aura Darkness Blade", and everyone's reaction when he revealed it.
    • You know who controls the entire Lucifer group? Grayfia who can practically make Surtr, a giant man who can breathe fire ''scared'' and Beowulf bow down to her.
  • Grayfia's entire In Vino Veritas moment when she's at the mixed hot springs with Issei. Seeing that stoic maid becoming The Tease in one fell swoop is pretty funny.
    • In the same short story, Ophis just ignores the entire epiphany about Issei and Grayfia being together and just says that she wants to swim. This was not lost on Issei.

Volume Fifteen

  • The girls from the Occult Research Club and the Student Council being forced to audition themselves as magical girls alongside with Serafall Leviathan, with all the girls wearing magical girl clothes. Also, Gasper and Mil-Tan actually joining the audition and passing the preliminary auditions.
  • The Church Trio actually buying an eroge for Issei.
  • YMMV on this one but one of the latest short stories involve Akeno having a S&M with her father after finding out that he and his wife engaged in that sort of thing every single night. Oh and Azazel joins them, being also a masochist. In short, all women are doms, all men are subs.
  • Fenrir's narration in which he can't get along with Kuroka and Bikou in his head.

Volume DX1

  • Abduction ERO: Seeing Issei lost his perverseness and instead talking about achieving world peace is not something you can see everyday.
  • Ultimate!! Oni-chan Mask!!: When cleaning the Gremory castle as tasked by Venelana, Issei stumbles upon Sirzechs and the latter shows video recording of Rias' childhood (including an album of her face when sleeping). Sirzechs later assigns Issei to capture Rias' face when sleeping at the present because there is a "missing link" in his album. Many laughs followed.
    • Rias begs to her mother and Kiba not to move her bear souvenir is both funny and cute.
    • The videos Sirzechs shows to Issei are rampant of laughs.
      • The first video shows the Gremory family when Sirzechs went off for work as Rias begged him to stay. Venelana tried to comfort her little daughter but she insisted and cried. At the same time, Lord Gremory held the camera and commented to Rias. Judging from little Rias' cute reaction and how Sirzechs and his father spoiled her as a child, no wonder the Gremory males are like that (this includes Issei).
      • The second video shows mini Rias and Sona playing and later fighting over Rias' teddy bear. The girls then cried because Sona ripped the doll's ear, and both Sirzechs and Serafall calmed them down. What really blows is when both siscons decided to settle down 'which one is CUTER' in a fight, but later broke off when Venelana scolded both people, now Satan Lords. High position doesn't mean you can escape your mother's anger, people, especially if she is the Brunette Madame of Extinction
    • Sirzechs cosplaying as Batman, dropping his alter-ego name and called Issei as "Agent Hyoudou" as he was assigned to take Rias' pictures takes the cake. Especially later when both men must face the wrath of the love of their life as a punishment (Grayfia and Rias respectively. Even Venelana also joins the fray). Sirzechs doesn't seem to find that wearing a Sentai cosplay was enough.
  • Records of Chichiryuutei's Pleasure Adventure: The Occult Research Club receives reports of a fake Oppai Dragon team operating in the outskirts so they go investigate. When they get there, they realize that the fake team is Vali and co with Vali as Oppai Dragon, Arthur as Darkness Knight Fang, Kuroka as Hellcat...and Bikou using transformation magic as Switch Princess.
    • Due to Bikou's trolling, a "Who is the real Oppai Dragon?" contest is held between the Occult Club and Vali's team for who's more fitting for the role. The third round is the Cardboard Box Vampire battle, with Gasper being compared to...a regular cardboard box. And the cardboard box wins.
    • The next round is the Switch Princess battle, and in order to beat Bikou, Rias allows Issei to touch her breasts. The light emitted as a result ends up revealing that one of the members of the audience was actually the dragon that Vali's team was looking for. Naturally, Ddraig is not happy at this development.

Volume DX2

  • The Student Council's Decision: Issei is filling in for a sick Saji at the student council and is helping Yura and Meguri conduct surprise inspections on the clubs. They're investigating the Manga Research Club, who're suspected of making H-manga. They manage to find the H-manga but it turns out to be Boys Love manga featuring Issei and Yuto. And it's already popular enough to have 15 volumes. Issei is not pleased to learn about this. Especially after the president asks who the "attacker" and "receiver" are.
    • Yura and Kusaka later ask the exact same question, again to Issei's distress.
    • To thank Issei for helping out, Sona bakes him a cake. However, Issei unfortunately learns that she's a Lethal Chef and that he has to finish the entire cake or potentially face the wrath of Serafall.
  • Let's go with Training: The Occult Research Club receives a request from a little kid hailing from a family of magical beast hunters to help him complete his family's Rite of Passage, so Azazel uses the opportunity to try out his new real life RPG "Azazel Quest". Hilarity Ensues.
  • Worship☆Dragon-God-Girl: A shrine was recently constructed for Ophis, so everyone celebrates by making wishes to it. The wishes range from heartwarming to comedic, but the crowner is Azazel, who just returned after a mahjong tournament that lasted all night. His wish quickly turns into a complaint about his subordinates and Heaven, and one of his comments prompts Issei to begin thinking of Gabriel as a seductive Fallen Angel. A bolt of lightning promptly strikes Azazel and Issei.
  • Hyakki Yako and Pandemonium: The Church Trio trick Issei into going into the Ero Room, however, they do so by using the bathroom door as the entrance, so Issei has other concerns.
    Issei: Let's do these kind of things next time! Right now nature is calling for me!
    • At the end of the story, Issei tries to be savvy and goes to a different restroom. Unfortunately for him, Xenovia expected this and set up the Ero Room in that bathroom instead.

Volume DX3

  • Let's Go with Training ~Mascot Chapter~: House Bael creates a mascot character, Bapple-kun, and the one wearing the suit is Sairaorg. However, his debut ends up sabatoged by his own stage fright. Wanting to learn about how to be a better mascot, Zeoticus, who turns out to be the one playing Greomory's mascot, Gomorin, takes Sairaorg to a mountain in order to train. Naturally, Issei gets dragged along as well.
    • The reason we haven't heard about Gomorin until now, it's because Gomorin is based on a camel, and Rias has a fear of camels due to an incident where she insulted a camel and it attacked her when she was a kid. This leads to the glorious image of Rias cowering behind Issei when Gomorin takes the stage.
    • Before they leave, Rias warns her father that Venelana will be upset if he suddenly takes off. Sure enough, later while the group is fighting bandits in mascot costumes, Venelana shows up and is furious. The bandits make the mistake of butting into the confrontation with her husband and she quickly demonstrates why she used to be known as the Brown-Haired Ruin Princess by annihilating them all in one blow.
  • Talents Of The Student Council: Saji bemoans how he's become the Only Sane Man of the Student Council in the face of Xenovia becoming president after it decided that they're going to fight against an infamous delinquent school.
    • The comparisons Saji makes between how Sona handled the Student Council's affairs and how Xenovia does so:
      • When sports clubs argued over the use of the gym, a teacher would be called over to mediate the argument. Xenovia decides that the clubs should determine it with a fist fight.
      • It turns out that the manga club is still making Yaoi manga of Issei and Yuto. Xenovia ends up critiquing the accuracy of it rather than shutting it down like she's supposed to.
      • Azazel is shown to be enabling Xenovia's outlandish ideas, like superpowered uniforms.
  • Worldly Desire of Steel: Issei and Asia go to visit Issei's grandma, and shortly after meeting, one of the first things she asks is that they hurry up and make great-grandkids. This, and Issei's parents voicing their agreement leads to Issei theorizing that perhaps his perversion is genetic.
    • Issei and Asia end up joining Seekvaria, Alivian and Elmenhilde in hunting down a vampire turned stray devil who's been attacking people in order to hypnotize them into servants. It turns out her motive is to force them to put together gunpla models so she can make a peerage out of them. Cue the vampire devil and Seekvaria getting sidetracked by a debate about Gundam continuities.
    • After dealing with the vampire, Seekvaria attempts to turn Elmenhilde into a Gundam fan by giving her a Blu-ray set under the pretext of research.
    • At the end, Issei and Asia attempt to sneak back into the house only find that Issei's grandmother found out and assumed that they went out to have sex. Issei takes this as confirmation that his perversion is indeed genetic.

Volume DX6

  • Story about style of Miyama Zero (Crossover with The Ambition of Oda Nobuna): Upon performing the aformentioned style, Issei and the ORC have swapped places with Nobuna Oda and her retainers. As Kiba tries to explain the situation, Cao Cao decides to make a visit to the ORC.
    • Cao Cao confronts Yoshiharu, who is disguised as Issei due to their similar appearance. Yoshiharu is confused by his appearance as he believes, like Nobuna/Nobunaga he should be a beautiful blonde girl. This freaks out Cao Cao, who fears that "Issei" has developed a feminization technique that works by touch, deciding it was best for him to leave.
      • After this Kiba, thinking about the possibility of Issei actually developing a feminization technique, starts blushing at the idea of such a technique being used on him. This motivates him to bring back Issei as soon as possible, so that he can learn the technique!

Dragon Magazine

  • The Ophis short story has a ton of these.
    • Rias asks a question as to what Ophis wants for her room since she's permanently staying at Issei's place. Her answer in a deadpan expression: "Great Red's neck."
    • Azazel being a salesman employee after resigning from being the Governor-General of the Grigori fallen angel faction.
    • While Issei, Rias, and Ophis are walking around in the mall, they run into Riser, Ravel, and Koneko. Riser wonders who Ophis is, and Koneko that she's Issei and Rias' child, prompting him to irrationally freak out, Ravel trying to calm her older brother down, and Rias dragging Issei and Ophis away to avoid his fiery rage.
      • Riser challenges Issei for Rias' breasts, prompting Issei to say that those breasts are off limits, but they can have a rematch anytime.
    • Rossweisse fighting against old women just for clothes on sale.
    • Ophis' going through the Lost Child Notice and pretty much describing how the Occult Research Club and some other people who they look like broadcasted throughout the entire department store: Crimson-haired big boobed mom (Rias), lecherous faced dad (Issei), normal-sized boobed golden haired sister (Asia), idiot sister with brute strength (Xenovia), self-proclaiming angel sister (Irina), two birds and a cat (Riser, Ravel, and Koneko), one more mom with big breasts (Akeno), sister looking like she has low happiness and is poor who is silver-haired (Rossweisse), and a handsome guy, cross-dressing guy, and glasses girl (Kiba, Gasper, and Shinra). The sheer embarrassment that ensued pretty much took the cake.

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