Jakob looks like he is about to go with them, but as soon as the have thier back to him, he grabs his sword and stabs one of them in the back. ((I dont know what roll that is. It could be deception dexterity or even stealth so ill let you roll.))
You stay awake, but you can't add your initiative modifier for struggle. Also you may want to roll initiative
Rapiers deal piercing damage, and as a fencer I am deeply offended by you saying a rapier can cut a beak. He would have stabbed the penguin, as attempting to cut something with any variety of rapier is futile
For initative i got a 17, and i should add my dex binus because you specified i could roll either a wisdom or constitution save, but since it was a poison, con is the onoy save that actually works. You as the dm must tell what saves to make, not give a choice between two, with only one actually working
The order if combat goes:crossbow penguin(p1), purple dragon, diesel riley, mushroomlord, and blasingpaladin, and finally the bladed flipper penguin(p2). The crossbow shoots for the escaped prisoner, but misses. Now might be a good time to discuss how combat is going to work. I will put the remaining enemies and the damage dealt to them at the end. When it's your turn, you can attack and take an action, wait for confirmation of the attack though. P1:no dmg P2:5dmg
We have to wait for the others to try to struggle free first since we have entered combat. It's turn based, to make things managable, and turns go off of initiative. It starts with purple dragon first.
Combat goes: Movement, Action, Bonus Action, Free Action in any order, using any you can/choose to. A combat round is divided into 6 seconds worth of stuff, so no long monologues trying to persuade. An action is most of what you want to do on a turn, usually being after, during, or before moving, while the bonus action is just a secondary thing you are capable of doing while perfoming your action. You may only cast one spell per turn, unless an ability tells you otherwise.