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My first "HOLY SHIT DND" moment
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I'm going to tell you how it went down. My character's name was Kalaban. Our party was about 8 and change characters strong. During this story there were 4. We'd meandered our way into the shadowfell via a planes war/spy plot with the summer court and found out the hard way that vampires and literally everything else there is hungrier, harsher, and more in the know than you. After some shenanigans, and nearly dying a few times, our characters found their way into a fortified town and took shelter in a church.

I'm a Dhampyr so it was less than comfortable but by the end of our chat with the local priest we'd figured out how to get home. That's when shit hit the fan. No sooner had the conversation finished than our Ranger noticed something coming down from the sky. Riding in on what I can only assume were Kestrals was a squad of vampires being lead by none other than the head of the shadow fell armies Second only to Strahd. 

This particular Vampire lord was named Alexie Torlov, and also happened to be my abusive bastard of a father. Kalaban had spent the better part of his life being isolated and tortured in hopes of gaining political leverage over my mother who was a member of the summer court. The end result was that Kalaban couldn't go anywhere without wearing a Mask (Bauta for all you venetians out there) and rarely communicated without the use of minor illusion or a disguise. Not to mention he'd live the rest of his life with a phobia of being trapped. 

Torlov had taken, stolen everything from us, and as terrified as we both were, there was no way we were going to let him leave without taking something back. 

Torlov and most of his cronies left the Mounts and proceeded into the Mare's house, leaving only one vampire to keep watch. We’d barely managed to take down 2 thralls last time and these were all full fledged vampires, in a straight fight we were dog food.

We'd snagged a uniform last session and I'd borrowed it for cover. I put it on and told the crew I had an idea. I've been known to roll poorly under pressure so the DM asked me the prophetic "are you sure about that?". I told him yes and ran towards the guard. 

"SIR!" 

I shouted, the DM looked at me RPing a annoyed vampire guard "Sir! I, ““GASP”” barely escaped, I’m-”

 “Who are you? You’re not in my legion”

 “N-no sir I’m not, I’m from the outpost next to the portal we were-” 

The guard lifted me up by the neck and I started panicking in and out of character.

 “Your uniform is dirty, you don’t look like a soldier”

 “Sir I'' ``choke! Choke!””  I’m not part of your legion I was assigned to the outpost by the porta,l “choke choke”, we were supposed to guard the mounts when the lieutenants went through but some people (the party) came in just a they left and attacked. I have our (looted) movement records here sir. “

It was at this point the DM told me to roll a my D20. Every other roll, every misadventure, every bit of spite I had for my father and what he represented came down to that one roll. My knuckles turned white and I dropped the Die. One click, then another, silence. Good or Guano. 

Me and the DM looked to the die and I Jumped out of my seat crying out “YES!” as a nat twenty faced the sky.

The guard dropped me with a snort to look at the papers I handed him “you will tell me everything”

I proceeded to give him a loose could’ve been could’ve not been description of our party “This Seems important, Alexei will want to know about this immediately” 

“Master Torlov is here?” Kalaban feigned surprise “ in that case I need you to get him immediately”

“No, you listen here you dirty fucking thrall-

This right here was just lucky rationing, I burned a boon, an inspiration, and double checked every bonus I could muster to turn a 10 into a 20.

I pulled an official order signed by Torlov himself out of my pocket and put it up to the Guard’s face “I didn’t speak of this because I wasn’t given permission, I have information for Lord Torlov. It’s about his son.” 

“Why don’t you go tell him yourself then?”

“Well that’s your job not mine isn’t it?” 

The guard was every kind of pissed but sure enough he grabbed the paper and gave me a last poke in the chest

“You stay here and guard our mounts…. and clean your uniform”

And with that, he left to enter the Mare’s house.

The rest of the party came out of hiding and we hauled our collective asses on the Kestrals and out of there, I’ll leave it to your imaginations what I left written in the dirt for Dad to find.

TLDR I play double agent and escape being turned into bat shit.

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4 years ago