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1. Learning to Ride (Day 13, Prompt 11) by the-gaudiest-of-vpns (3emo5you)

   Fandoms: Supernatural (TV 2005)  

   • Explicit
   • No Archive Warnings Apply
   • M/M
   • Complete Work

   13 Oct 2025

   Tags

   • No Archive Warnings Apply
   • Castiel/Dean Winchester
   • Dean Winchester
   • Castiel (Supernatural)
   • Kinktober 2025
   • Handcuffs
   • Somnophilia
   • Bottom Dean Winchester
   • Top Castiel (Supernatural)
   • Top Castiel/Bottom Dean Winchester
   • Sub Dean Winchester
   • Dom Castiel (Supernatural)
   • Dom Castiel/Sub Dean Winchester
   • Castiel Has a Large Penis (Supernatural)
   • Dean Winchester Has a Small Penis
   • Humiliation Kink
   • Aftercare
   • Premature Ejaculation
   • Come Eating
   • Castiel Cares About Dean Winchester
   • Desperate Dean Winchester
   • Unsafe Sex
   • but Cas is an angel soooo
   • Dirty Talk
   • Small Penis Humiliation
   • Barebacking
   • Dean Winchester is a Quick Squirter
   • Dean is Castiel's Good Boy
   • good boy dean winchester
   • Sexual Overstimulation
   • Bottoming from the Top
   • Cowgirl Position
   • Hand Jobs
   • Blow Jobs
   • Kink Exploration

   Summary

   Cas pulls out a new toy and Dean gets quite the wakeup call.

   Series

   • Part 13 of Discovering Themselves Together (Kinktober 2025)

   Language:

   English

   Words:

   3,990

   Chapters:

   1/1

   Comments:

   2

   Kudos:

   91

   Bookmarks:

   7

   Hits:

   2,238