Hey there!
These are pretty good ideas. However it would be a lot of extra work. Adding all that in would take a good amount of time, and testing. It would also be a bit out of character for Ember currently. Please don't be discouraged from suggest ideas though. These are good ideas, but I already have a lot planned. I don't want to end up as one of those devs that bites off more than they can chew, and never finishes their game.
If you like the pillories though you're probably going to like the v0.2 update. If you got $3, and you want to see some animation sneak peeks check out the Substar. Otherwise just hold tight for a bit till v0.2 becomes the free build.
Aside from the gameplay related sex, I plan to have cutscenes where I can explore more scenarios like the stuck one you were talking about. I have also though about the trap idea, but I already have a lot of animations on my plate. Currently, just for Ember I will need 4 goblin animations, 4 orc animations, and 2-4 ogre animations. All with 1P, and 2P versions. With variants for after Ember gets fucked already. That's just for when she gets grabbed. There will also be cutscene animations. I will also need 3 goblin, orc, and ogre animations. One for each NPC characters. Also with after sex versions. Then there is all the cutscene animations for the other characters as well. (Jenny, Nyth, Lila, Maggie, Lyn,+ more.) So I'm trying not to take on a whole lot of new mechanics or animations right now. The more successful the game becomes though, the more I can take the time to add things like that though.
I don't know a whole lot about modding TBH. I make the game in Pixel Game Maker MV. So if that is a moddable platform it would be really cool to see mods. You could even mod in the Jack-o pose as an alternative "downed frontside" pose. That would be a pretty cool mod. Just a simple sprite replacement.