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To keep the prompt posts more manageable in size for modding, this post is closed to new prompts now. New Prompts should go in Prompt Post #20. 

This post remains open, however, for you to link fills or express your excitement over prompts you would like to see filled. 

There are still many, many gorgeous prompts in this post that have not yet been written or drawn. For easier browsing, check out the Pinboard. 

Remember: 

Any characters, any ship, any trope, any kink are welcome (with the sole exception of sexual scenarios involving human(oid) characters under 14). 

Each prompt gets a new comment directly under the post. Don't use threaded comments for new prompts. Only squee, encouragement, and links to fills go in the comments responding to individual prompts.

Prompts should be posted anonymously to make sure that everyone's prompts are treated equally.

Please use a header with your character(s)/pairing and a keyword or short phrase (For example: "Andy/Quynh, Make-up sex" or "Nicky/Joe/Booker, first time DP").

From: (Anonymous)
(Booker/Joe - kind of, established Joe/Nicky)

It's been just a couple of years since Booker started traveling with the Old Guard and he has finally begun to settle into the group dynamic. He is clever, cheeky and resourceful and he very quickly learned to get along with all the other immortals; not to mention - he also has a rather relaxed attitude towards the unabashedly romantic relationship between his two male companions, atypical of the time period. Except…

During one drunken debate, after a successful mission, Booker blurts out that he could not really enjoy anal sex "knowing" that his lover is uncomfortable or possibly even in pain. It turns out Booker believes that the receiving partner doesn't really find pleasure in being penetrated and that he (or her!) would merely be indulging the needs of the other. Of course, the group tries to (drunkenly) dissuade him but to no avail.

Finally, Joe loses his patience and claims that he could easily make any man come, gay or not, just by using his fingers. On his butt. In twenty minutes.

Booker doesn't believe him.

Nicky, who has lost every bet with Booker by that point, asks him if he would like to place a wager on that.

…And twenty minutes later Booker has developed a bit of a man-crush on Joe after not one but three mind-blowing orgasms, Nicky has won all of his money (and is quite turned on by his husband's demonstration of skill) while Andy is just rolling on the floor laughing.
From: (Anonymous)
+1 for Nicky finally winning a bet

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