"Perhaps we should stop and consider a moment," Damros said to no one in particular. 

" If a human and a duegar were working together to 'block something'.. perhaps we should not rampage willy-nilly through the questionable door."      

"Perhaps..."

Sehaethas changes into Kylaski. She puts away the crossbow, "Lets try the door that they weren't blocking. Worse that could happen is that it's a dead end."

Xaul backs away from the dangerous door and nods 'Yeah, best we try that one first then.'

"The enemy of my enemy is my friend," thinks Skye outloud. "Could be that the issue behind that door--" she points to the barricade "--ain't quite so much an issue for us, maybe."

Kylaski speaks with Sehaethas' voice, "I would find that more likely if they weren't trying to seal the gap under the door."

 The door opens to a corridor, ending in steps up looking like it opens up more. You do hear some noises coming from up there, including the occasional scream. "That sounds like Floon!" (did you guys forget you had Renaer with you still?)

Xaul gasps and says ‘Looks like we should head up there ready for a fight!’ 

Renaer has already drawn his weapons. For a noble, he looks like he might know how to use them.

With a smile on her face, Kylaski heads for the stairs. 

Skye brings up the rear. 

Damros decides he will give his hand crossbow a chance for a silent 'greeting' when the time comes.

Xaul’s hand crackles with icy magic as he prepares frostbite. ‘Let’s head out’ 

Two threadbare curtains (each acting as a makeshift door) hang on the east wall of a long hall, in the middle of which a muscular half-orc in dingy robes stands with his foot on the chest of a male human with wavy red-blond hair. Fire burns around the orc’s clenched fist, and his victim cries and squirms helplessly beneath him.

Seated on a raised platform to the south is a nightmarish figure wearing black robes. It has large white eyes and rubbery purple skin, with four tentacles encircling its inhuman mouth. It cradles and gently caresses what looks like a disembodied brain with feet. (in terms of the map, to save me from uploading lots, I have gone with equivalent images. The brain is the beetle, and the mindflayer is the beholder. You are all names. Floon is the one with the red dot.)

 Damros fires his crossbow at the physically largest threat, the orc. It flies true but the orc quickly shouts and waves his hands and a magical shield appears blocking the bolt.
Skye also aims at them and misses.
Xaul tries to freeze the mindflayer but it shrugs it off, but the brain gets hit with a tentacle
Kylaski didn't specify a particular readied action going up the stairs, but I will assume they eldritch blast the orc, which goes through the shield for 3 damage (rolled on sheet).
Renaer needs to get closer, something he will do on his actual turn.

I normally do average initiatives, but as two of you rolled and got the two ends of the spectrum, I rolled for everyone and am grouping. The mindflayer and Damros are simultaneously first. The mindflayer will put the brain down, and calmly walk towards (and out of) the double doors. Unless Damros does anything at the same time to stop his movement. Xaul goes before the brain and orc, and then after that everyone can post (though technically Skye, Kylaski and Renaer would act before Damros and Xaul if anyone has any actions that depend on someone else)

[Ah, looks like you posted just before my PM lol!]

As said above, as part of the initial surprise round Xaul attacks the Mind Flayer with frostbite but they easily resist it. Also as part of the surprise round as his bonus action, he summons and attacks with his Tentacle Of The Deep to attack the Animated Brain with a 16 to hit for 1 cold damage and a 10 foot speed reduction until the start of Xaul's next turn.

Okay, by the looks of initiative, I'm after Damros so I'll post Xaul's next turn after that!

On his next turn after the surprise round, Xaul attacks the Brain again with his Tentacle and outstretches his palm to hit it with a blast of frost. He's a bit concerned to see that the Orc's a spellcaster like him, which might mean he's a bit more of a challenge than expected, but just thinks 'If we can get through this abberant threat first, we can maybe reason with the Orc after, or just tag-team him since it's 5 vs 1. Then once he's dealt with, we can potentially pursue the tentacly fella.'

Action: Frostbite on Brain: DC 12 Con Save or take 1 cold damage and have disadvantage on its next weapon attack roll until the end of its next turn.
Bonus Action: Tentacle of the Deep on Brain: 9 to hit, 5 cold damage on a hit and 10 foot speed reduction until the start of Xaul's next turn.

Skye summons a thunderous bolt of cloudy wrath, aiming at the orc over Floon. 

Action: Eldritch Blast. (Attack roll: Nat 20+5. Damage roll: 10 force, 2 thunder.) 

Damros gives his hand crossbow a dirty look but then his eyes get saucer huge upon seeing the mindflayer and the 'walking brain'.   "Mindflayer!" he yells as he speaks more arcane words and makes the gestures that send a purple-black line of energy at the brain creature.

Eldritch Blast    (( Sadly, game log ))    To Hit:  3 + 7 = 10      Damage:  1 force

Damros starts a steady stream of curses in various languages.   "Kill that brain and then the mind flayer if you value your mind and sanity."

Kylaski thinks for a moment, then continues to target the orc.

Attack 9 for 8 damage

(Not that it matters what she attacks with attack rolls like that :-( )

(Sehaethas and Kylaski are already schizophrenic. Though if she actually understood what you were saying it would be different. Just lost  a player to one of those in a different game, so I as a player know how nasty those things are!)

Quote from JSenecal >>

Kylaski thinks for a moment, then continues to target the orc.

Attack 9 for 8 damage

(Not that it matters what she attacks with attack rolls like that :-( )

(Sehaethas and Kylaski are already schizophrenic. Though if she actually understood what you were saying it would be different. Just lost  a player to one of those in a different game, so I as a player know how nasty those things are!)

 (do you mean lost a player character, or an actual player - the person? I'm so sorry if so. That's tragic. Hope you're ok)

(I think they meant they lost a player's character to a mindflayer, though I might be wrong)

Damros misses and the mindflayer leaves the room. 

Xaul causes frost to settle on the brain, but the tentacle misses.

The orc moves and casts a spell, sending a cone of fire that catches the three people on the front line. Dex save dc 12 or 10 fire damage.

The brain then moves very fast (dashing) right up to Damros.

(Map as of this point of combat)

Kylaski then misses the orc, (just... only had 10 AC without Shield) but distracted him enough for Skye to get a solid hit in. This orc might be powerful, but he is not strong. He is also no longer breathing (I updated the map before resolving these turns, so just use it to mark his corpse)

Renaer then runs infront of Kylaski and attacks the brain three times. It hits with the dagger but the other two miss, the first miss throwing Renaer off so much that the second attack (nat 1) causes him to drop his rapier. He quickly retreats (bonus action disengage) and grabs the rapier in the process. (His rolls are in the game log. Ignore the 12 damage one as I forgot to roll to hit first and then missed twice) The creature seems mostly unphased by the dagger, seemingly taking less damage than expected.

Back to Xaul and Damros though everyone can state actions and I will resolve them after the brain.