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1. The Bachelor by blondieschick

   Fandoms: Gossip Girl (TV 2007)  

   • Explicit
   • Rape/Non-Con, Underage Sex
   • F/M
   • Work in Progress

   28 Oct 2025

   Tags

   • Rape/Non-Con
   • Underage Sex
   • Chuck Bass/Jenny Humphrey
   • Jenny Humphrey
   • Chuck Bass
   • Dan Humphrey
   • Rufus Humphrey
   • Lily van der Woodsen
   • Blair Waldorf
   • Serena van der Woodsen
   • Nate Archibald
   • Eric van der Woodsen
   • Alternate Universe - Arranged Marriage
   • Arranged Marriage
   • Smut
   • Shameless Smut
   • Slow Burn
   • Chuck is a douchebag and warning all on his own
   • Past Blair Waldorf/ Chuck Bass
   • Past Jenny Humphrey/ Nate Archibald
   • Minor Blair bashing
   • Minor Character Death
   • Legal Drama
   • Minor Original Character(s)
   • Possessive Behavior
   • Slow Romance

   Summary

   Chuck and Jenny, left alone in New York after graduation, find themselves entangled in a deeply passionate friends with benefits arrangement. What happens when Chuck's circumstances change overnight and he finds himself needing more from Jenny than he anticipated? Chuck and Jenny have both changed and grown up since highschool but can a leopard really change its spots? Can they survive the Upper East Side? Can they survive the demons of their past and make it, against all odds?

   Language:

   English

   Words:

   15,657

   Chapters:

   8/25

   Comments:

   16

   Kudos:

   26

   Bookmarks:

   6

   Hits:

   1,091