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1. Bend it Till it Breaks by kuaptic for Rowan_555, HansoDax, ClumsyBookworm18, KitsuneUdon743, monfivela, LokiNightfury, panjava_clown_69, Alexa_K3S

   Fandoms: The Umbrella Academy (TV)  

   • Explicit
   • Graphic Depictions Of Violence
   • F/M
   • Complete Work

   28 Aug 2025

   Tags

   • Graphic Depictions Of Violence
   • Number Five | The Boy/Lila Pitts
   • Number Five | The Boy & Reginald Hargreeves
   • Number Five | The Boy (Umbrella Academy)
   • Lila Pitts
   • Herb (Umbrella Academy)
   • Number Five wears a dress Mission for the Commission Everyone's got some stuff to work out Number Five aged up
   • Fivela
   • Gender Identity
   • Gender Issues
   • Identity
   • Canon Divergent
   • Alternate Universe
   • Five Lila
   • Romance/Angst
   • Explicit Sexual Content
   • Banter
   • Fighting
   • Quips
   • POV first person five
   • five hargreeves and Lila pitts
   • Oral Sex
   • Vaginal Sex
   • Anal Sex
   • Pegging
   • Number Five | The Boy & Lila Pitts Bantering

   Summary

   The mission seemed simple at first -- kill the guy who kills Hitler and who else would the Commission give it to but their best agents, Five Hargreeves and Lila Pitts. There's just one tiny problem. Lila can't play the temptress, so the roll falls to Five. It's not a problem for him, but when Lila gets intense about teaching him how to be a woman, things go awry.

   Language:

   English

   Words:

   11,326

   Chapters:

   2/2

   Collections:

   1

   Comments:

   9

   Kudos:

   15

   Bookmarks:

   2

   Hits:

   301