Okay, this is going to be bizarrely specific, but I would love to read something along the lines of Essek post-canon being in a tenuous, potentially deadly situation where he has to seduce/fuck someone in order to keep his cover intact. Essek is inexperienced in doing these kinds of things, since his expertise as Shadowhand lay in political manipulation and court politics, not this kind of intimate seduction, and sex isn’t something that he is naturally inclined to. But he knows that Caleb knows how to do these things, was trained in it, if not the exact shape of what Caleb was trained in. So in desperation, he sends to Caleb to guide him through fucking this person, and Caleb tries to help Essek through the act. (Via some Sending spell of extended duration developed by Jester?? Idk.)

Just—Essek, inexperienced and trying to keep it together, in a delicate situation where extenuating circumstances make it so fucking someone is the only option to keep his cover, with Caleb’s voice in his head trying to guide him through it and make it marginally easier for him, and Caleb desperate to help, with no way to extricate Essek from this situation except these methods he was trained in?

Could be with an established relationship between the two of them, with the familiarity between them making the situation marginally less terrible for Essek with the comfort of Caleb’s presence, and the both of them finding some kind of pleasure in Caleb guiding Essek through fucking someone? Or it could be pre-relationship, with the ache of Caleb trying to help Essek through this intensely intimate situation while their own relationship is still loose and undefined and they haven’t had this kind of sexual experience together? Either is really good, oh man.