Adult Content Warning

This work could have adult content. If you continue, you have agreed that you are willing to see such content.

• Yes, Continue
• No, Go Back

If you accept cookies from our site and you choose "Yes, Continue", you will not be asked again during this session (that is, until you close your browser). If you log in you can store your preference and never be asked again.

1. A Very Merry Christmas... With My Boss (Dean Winchester x Sylvia (OC)) by just_some_smut

   Fandoms: Supernatural (TV 2005)  

   • Mature
   • Creator Chose Not To Use Archive Warnings
   • F/M
   • Complete Work

   02 Jul 2025

   Tags

   • Creator Chose Not To Use Archive Warnings
   • Dean Winchester/OC
   • Dean Winchester - Relationship
   • Original Character - Relationship
   • Dean Winchester/Original Female Character(s)
   • Dean Winchester
   • Sylvia (OC)
   • Supernatural - Freeform
   • deanwinchester - Freeform
   • Sex
   • Smut
   • Top Dean Winchester
   • Public Sex
   • public mastrubation
   • Toys
   • dildo
   • Vibrator
   • Squirting
   • Cum Eating
   • Rough Sex
   • Blow Job
   • sucking dick
   • dean winchester eating out
   • dean winchester likes squirting
   • Dean Winchester Smut
   • dean winchester sex
   • dean winchester in control
   • Bottom OC
   • dean winchester mastrubation
   • dean winchester secretly watches mastrubation
   • spn dean winchester smut
   • spn dean winchester
   • supernatural dean winchester smut
   • Office Sex
   • office smut
   • dean winchester office sex
   • face fucking
   • Consensual Sex
   • Eventual Smut

   Summary

   Dean, the boss, and Sylvia, the employee, have been eyeing each other up and down for far too long. After a public sexual rendezvous in the office, tensions are at an all time high. They couldn't resist it and gave into temptations at their company's holiday party.

   Language:

   English

   Words:

   5,703

   Chapters:

   1/1

   Collections:

   1

   Comments:

   1

   Kudos:

   18

   Bookmarks:

   2

   Hits:

   627