Yeah, you knew it was coming!

Homestuck has enemyshipping built right into the worldbuilding: there are two main races in Homestuck, Trolls and Humans. Humans, traditionally, have friends and lovers. Trolls have a fourfold system: matesprit, kismesis, moirail, and auspistice, and to be truly fulfilled in life you have to have all four. Moirail is basically platonic life partner. Auspistice is... complicated. Matesprit is for people you have pantsfeeling for and actually enjoy spending time with. Kismesis is for people you have pantsfeelings for and hate the guts of, and a true kismesis is your best nemesis, the person who taught you the meaning of hate, the person who will foil your every triumph and destroy your every dream, and make you beg them for more. (It is not rare, however, to flip back and forth repeatedly between kismesis and matesprit, which is also very good.) That was, honestly, the only thing I knew about Homestuck when I started reading the fic, but, you know, enemyship. So I'm going to throw you in with no more background than that, because hey, it worked for me!

As you might expect in a fandom with 36 main characters and a built-in nemesis shipping requirement for everyone, there are a LOT of enemyships in this fandom, and many of them are very good. I honestly cannot keep straight which are canon and which aren't at this point!

But there is one kismesis ship in Homestuck which is the best one of all, and it was in either the first or second Homestuck fic I ever read: Past Karkat/Future Karkat. Because, you see, in a bad mood Karkat hates everyone and everything, but he hates himself even more, and most of all he hates his past self and his future self. (If you have never been in an enemies/lovers ship with your past self or future self, are you even human? Right now I am deliberately pissing off my future self by writing this instead of getting my laundry out of the dryer, but future me deserves it I'm sure for being so annoyed at past me.)

And Karkat has access to text messaging software which lets him text with his past and future self! He can *actually* express his dislike directly at him. And there's also something *extremely* satisfying about realizing maybe you don't hate past you and future you after all: maybe you really loved them all along. So: have some crosstime enemies-to-lovers text messaging recs.

• Fruity Rumpus Asshole Factory, Concupiscent Frustration Edition (12639 words) by orphan_account
  Chapters: 7/8
  Fandom: Homestuck
  Rating: Explicit
  Warnings: Underage
  Relationships: Karkat Vantas♠Karkat Vantas, Karkat Vantas♥Karkat Vantas, Rose Lalonde/Kanaya Maryam, Gamzee Makara⋄Karkat Vantas, Terezi Pyrope ⋄ Dave Strider, Dave Strider♠Karkat Vantas
  Additional Tags: Self-cest, Masturbation, Cybersex, Black Romance, Humor, Bisexuality, Xeno
  
  In which Karkat flips blackrom to redrom with himself.



• Helping yourself (4989 words) by Anon_H
  Chapters: 3/3
  Fandom: Homestuck
  Rating: General Audiences
  Warnings: No Archive Warnings Apply
  Relationships: Karkat Vantas♠Karkat Vantas; Karkat Vantas⋄Everyone
  Additional Tags: Pale Romance | Moirallegiance, Self-cest, Pesterlog, Meteor, Pale Porn, pale masturbation
  
  In which Karkat flips blackrom to palerom with himself.



• Believe Me When I Say Fuck (4997 words) by Rag
  Fandom: Homestuck
  Rating: Explicit
  Warnings: Creator Chose Not To Use Archive Warnings
  Relationships: Karkat Vantas♠Karkat Vantas, Dave Strider♥Karkat Vantas
  Additional Tags: Selfcest, Self-Hatred, Implied/Referenced Self-Harm, Caliginous Romance | Kismesis, Clonefucking, Violent Sex, Bulges and Nooks, Hair-pulling, Orgasm Delay/Denial, Mild Genital Torture, Voyeurism, Flushed Romance | Matesprits, First Time, FaceFucking, Unhealthy Kismesissitude
  
  Bonus rec: In which Present Karkat gets the chance to actually fuck Present Karkat.