Pairings: Dean/Cas, Sam/Eileen, Charlie/Meg, Past Dean/Ash
Rating: Explicit
Word Count: 37K
Author: @nickelkeep
Artist: PieDarling (@zelirocks)
Posting: October 22nd for @deancasbigbang
Tags: Angst, Hurt/Comfort, Internal Homophobia, Sexual Harassment, Non-Consensual Kissing (Not Dean/Cas)
Dean hasnât taken a proper vacation in over three years. Sam and Eileen, to thank him for everything heâs done for Sam, send Dean on a cruise.
When heâs already used to things in his life going wrong, Deanâs not surprised to find things stacking up against him from the get-go. But with the help of a new friend, can Dean finally catch a break?
Dean entered his assigned cabin and unceremoniously dropped his bag onto the bed. He looked around, surprised at what his brother and sister-in-law had gotten for him. He dragged his hand down his face and sat on the queen size bed. He was still worried about the state of the garage without him, but maybe Sam, Bobby, and Eileen were right. He could use a vacation.
As he continued to take in his home sweet home for his trip, he noticed a gift basket sitting on the roomâs built-in desk. He smiled as he stood up and crossed over to the desk. This group held nothing back. With condoms of every size, shape, color, and flavor, several different lubes, different sex toys, it was as though they fully expected their guests to get busy.
Dean pulled the different items out one by one until he came across a folder with the cruise lineâs logo and âCruise Itineraryâ on it. He sat in the desk chair and opened it, excited to see what he would be up to for the next seven days.Â
âSonofabitch.â Dean let the folder fall to the desk in shock. On the first page, in bright and bold letters: LGBTQ+ Mixer Cruise Itinerary. Dean blinked several times. There was no way Sam and Eileen didnât know what they had booked him on, right? Did they think he had been single because he was Gay? While Swayze may get a pass, Dean knew for certain he was not Gay.Â
Dean shot out of the chair and looked out the window of his cabin. They had left port, so he couldnât get off the ship. He pulled out his cell phone and found no signal. He did find wifi and went back to the folder to find the instructions to connect.
A few moments later he was calling Sam over Skype. âDean, miss me already?â
âDonât play stupid Sam. This isnât just a singles cruise.â
âOh shit, are they old?â Sam started laughing. âMaybe thatâs why it was a good deal. Sixty-five plus discount.â
âNo, Sam. Itâs for Gay People.â
âSo?! Sam, Iâm not Gay.â
âWell, you sure as hell ainât straight either.â Sam threw back. Dean could picture his younger brotherâs bitchface perfectly.
âEnjoy your cruise. Remember that Bisexual and Pansexual are LGBT too.â