Kanashii no Imi

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Written by an author who called himself Leaf-chan, Kanashii no Imi is a Tenchi Muyo! fanfic in which an Original Character named Jeff is accidentally teleported into the Tenchi universe by Washu. Washu ends up deciding to keep Jeff for experiments, but allows him to go and see the other girls. There, he encounters Sasami. The situation... degenerates rapidly.

The fanfic gained rapid notoriety in the Tenchi Muyo! fanbase for its disturbing nature and its protagonist, who, in many respects, resembled a negative otaku stereotype. To this day, it is one of the most infamous fics in the fandom.

You can read it here, but be warned that it is highly NSFW.

Tropes used in Kanashii no Imi include:

• Accidental Pervert: After trying to evade a fight and narrowly dodging Ryo-ohki, Jeff ends up faceplanting into Ayeka's buns.
• Awful Truth: Jeff finds himself coming to terms with his desire to bonk Sasami.
• Battle in the Center of the Mind: Jeff's rational mind and base mind have a discussion throughout the piece that bears shades of Good Angel, Bad Angel.
• Beige Prose:

She was in her lab as always, fiddling and diddling with this and that. Lights flickered, photons burst, people died, and stuff happened as she experimented with her latest invention, something that she termed the "Reality Distortion Transportation Thingamabob". Hours and hours passed as she worked.... and all the while, the reader was left in total boredom.

• Bittersweet Ending: Sasami's been defiled and killed, but it's implied that Ayeka, Ryoko and Washu will have their revenge.
• Break the Cutie/Mind Rape: Mundane. Sasami loses almost all will to live after being forced to give Jeff head.
• Broken Record: Jeff goes into something of a mental loop as he fantasizes about Sasami in the bathroom.
• Buffy-Speak: Washu's cross-dimensional teleporter was clearly named on the fly.
• Character Development: Jeff goes from your standard, if bias-inspired everyman to a shameless, unfeeling sociopath, step by step by step...
• A Date with Rosie Palms: What Jeff is doing when he first appears in Washu's lab, and in the bathroom after seeing down Sasami's shirt, and whilst sitting across the table from Sasami at dinnertime, and as he contemplates rape.
• Deconstructed Trope:
  • Lolicon
  • Perverse Sexual Lust
  • Their First Time
• Evil Makes You Ugly: Jeff inverts this.
• Fan Disservice: The sex scenes.
• Fat Slob/Fat Bastard: Jeff
• Foreshadowing: Multiple instances, in varying degrees of subtlety.
• Gone Horribly Right: Washu built a machine to summon a being from another dimension. It worked.
• Gratuitous Japanese: Leaf-Chan translates it as "The Significance of Grief." He's one character off — it actually means "The Meaning of Sad."
• The Grunting Orgasm: Jeff, while popping one off the wrist in the Masaki bathroom.
• Huge Guy, Tiny Girl: If not by mutual agreement...
• Humiliation Conga: Sasami.
• I Didn't Mean to Turn You On: Sasami to Jeff.
• It Got Worse
• Jumping Off the Slippery Slope: Jeff.
• Kill the Cutie
• Lack of Empathy: Jeff, eventually.
• Laughing Mad: Jeff, after leading the gang to Sasami's corpse.
• Lie Back and Think of England: Jeff, at one point, asks Sasami to pretend that his willy is a lollipop.
• Lust Object: Sasami becomes that of Jeff.
• Making Love in All the Wrong Places: Jeff has Sasami in the Masaki backyard.
• Medium Awareness: Zigzagged earlier on: Jeff is quite aware that he's in a cartoon and attempts to convince the cast such, to no avail.
• Murderers Are Rapists: Inverted; Jeff sets out to rape Sasami before deciding, after the act, to kill her.
• My Friends and Zoidberg: When Jeff asks Washu if he can meet the rest of the cast.

[C]an I at least get to say hi to the others? You know... Ryoko, Aeka, S-Sasami, and Ryo-ohki...? Oh yeah, and Tenchi too.

• My God, What Have I Done?: Jeff is driven insane at the end by horror at what he's done to Sasami and fear of the others' retribution.
• Naughty Starting Roughly at 1:14 in the Morning
• Nerds Are Virgins: Jeff... at the beginning.
• Occidental Otaku: Jeff
• Oh Crap: Jeff, when he's raped and killed Sasami and realizes the rest of the cast are about to descend on him.
• Otaku: Jeff
• The Peeping Tom: Jeff gets a moment of this.
• Percussive Maintenance: Washu, booting up her machine.
• Pocket Dimension: referenced almost by name.
• Raging Stiffie: Jeff, as he weighs out the pros and cons of child molestation.
• Rape and Revenge: The former unto Sasami, the latter from the rest of the gang.
• Rape as Drama
• Rape Is a Special Kind of Evil
• Rape Is Love: Averted:

Sasami: "I—hate ...you."

• Reality Warper: Washu's Reality Distortion Transportation Thingamabob.
• Sex Changes Everything: Played for Drama
• Sex Equals Love: Jeff's rational mind is aware that this isn't true.
• Shout-Out: Multiple, ranging from Title Dropping to subtle ones. In particular, a reference is made to a character in Nabokov's Lolita, and a scene is reminiscent of a similar one in "The Tell-Tale Heart".
• The Sociopath: By the end, Jeff has become a full-blown instance.
• Stockholm Syndrome: Averted.
• The Stoic:

[Jeff] never did have emotions to start with.

• Straw Fan: Jeff, a potshot at otaku in general.
• Subbing Versus Dubbing: Jeff ends up wishing he was in the English dub rather than the Japanese version after hearing Sasami's voice.
• This Loser Is You: Jeff is meant to be a stock otaku analogue.
• Tradesnark™: Inserted several times near the beginning of the fic.
• Translation Convention: Invoked in-universe.
• Villain Protagonist: Jeff, by the end.
• Virginity Flag: Jeff never washed off the blood.
• What Do You Mean Its Not Symbolic: In-Universe:

He'd crossed the threshold, in more ways than one; beyond a physical concept, it was a blatant metaphor for what he was about to attempt...

• With Catlike Tread: Enforced via creaky floorboard, but it still succeeds.
• Would Hit a Girl/Would Hurt a Child: Jeff.
• Word Salad Title: Both the actual title (lit. "The Meaning of Sad") and its supposed translation, "The Significance of Grief".
• Your Mind Makes It Real: Jeff is essentially perceiving Sasami's inherent beauty.