I'm as fresh as a GM as you can get, and our first adventure is Curse of Strahd.

My party has just killed Doru in the basement of the church in Barovia at the end of our last session. One of the PC's wants to disguise like Doru and make a visit to his "father" (Strahd) in the next session. They have not met Strahd yet, but I guess his spies has their eyes on them.

I can have Ismark tell the player that: "Strahd has spies everywhere, this will never work!"

- If the player disguises as Doru right away, and runs out of the church right away, I might let it work. I will let him pass safely to Castle Ravenloft.
- If the player linger with the disguise after killing Doru, then the spies will report back to Strahd that Doru is dead. The disguise will fail, and I can have a little fun with the caracter.
- Should I factor in that Strahd and vampire spawns has a bond that break when the spawn dies? If so, the players attempt will fail no matter what.

I need help from someone who has played CoS before. How can I let Sthrad be fooled, and what information should he give the caracter? On the other hand; if Strahd is not fooled, how can I "toy" with the player, and lead him to think he was successful? (The only thing I'm certain of, is that the player will find a portrait of what he thinks is Ireena in the Castle.)

Remember, the characters are here for Strahd's amusement. He maymeet with the characters, even invite them for supper, merely to to get a feel for them. Until he and the party are ready, he would probably let the party thing they had fooled him.

Also, if there are any female characters with a decent charisma, Strahd may decide he wants that character as another of his brides.