The Couatl will fly to Sekkar and heal him if it is able to reach the Lizardman. (Heal: 8) If there are still movement left, it will try to stay away from the Demon Lord.

(By the way, don't forget to add 1d10 to your attack rolls and saving throws. Sekkar do you want to roll a d10 to add to your second attack? It might be enough...)

Pax Wisdom Save vs DC 23 : 19      Inspiration to re-roll the d20 : 12

*eyeroll* 

Why are they doing this again?!?  This is SUICIDE!!!  She turns and bolts, running away from the thing.  She runs up to 70 feet and tries to get behind some large piece of cover.  

Assuming she does, save at the end of her turn: Pax Wisdom Save vs DC 23 : 23

Will gladly add it! Let's see if d10 helps: 6

Yes! With the help of Jimjar's blessing, Sekkar's second attack does in fact hit.

I think we are overdue for a map!

I've gone back over everyone's posts and I'm confident all these positions are correct. If you have any concerns please post them in the private message thread.
Sorry I used the Kastix pic for Kirin. I'll fix it on the next update.

IMPORTANT NOTE: I just re-read Sekkar's post, and there is no way Demogorgon could have swiped with his tail at the end of Sekkar's turn, as Sekkar moved 30' away by virtue of the Zephyr Strike. So, with no valid targets for the tail I'll have to retract that attack and do something else instead.

REPLACEMENT ACTION: Demogorgon swishes his tail in irritation, but the irritant has swiftly darted out of reach. Instead the glowing red eyes of one of his heads turn and attempt to lock their gaze on Kirin.
Kirin: You have a choice to either:
1) Attempt a DC 23 Wisdom saving throw (don't forget your extra 1d10)
2) Avert your eyes to avoid the gaze. If you do you can't see Demogorgon until the start of HIS next turn. Looking at him in the meantime would require you to make the saving throw.

With no attack on Sekkar (and him out of the Couatl's range anyway), Rhayna can either keep the Couatl in reserve or do something else on the Couatl's turn if desired.

Now for something that I think is unaffected by these alterations...

Pax runs like the little girl that she is, with thoughts of dismemberment plaguing her mind. But no sooner does she get out of harm's way than she manages to get control of herself and remember that she isn't a little girl any more, she is a big girl with a big heart and a big desire to get a decent crack at this demon lord or die trying!

Pax passes her end of turn save and is no longer frightened

Kaylyn, Kirin and Rhayna are next.

Kaylyn you can keep your original attack rolls for now if you like them, or choose some other action.

ROUND 1: Rhayna 21, Demogorgon 19, Sekkar 16, Couatl 12, Pax 12, Kaylyn 10, Kirin 5.
ROUND 2: Rhayna 21

(Whew!)

(Couatl position is fine, but it if flying about 60 feet in the air behind Kirin. Also, if it's ok, she will move 30' forward, and try ducking behind a structure. If so, according the the map, she would be about 70 feet from the Demon Lord?)

Hidden within the the shadows of darkness Kaylyn remains unseen by Demogorgon and let's the magic flow as she attacks the Demon Lord

(I'll keep my original attacks)

She then moves back another 30 feet to keep out of range of the terrifying gaze.

Judging the distance, Kirin stashes his dagger away for now before points grabbing his staff with both hands to steady himself. Typically he would cast spell with a wave of his staff, this time he charges the fireball on the end of his staff before reaching back and swining his staff like a great sword, throwing the Fireball at the demon lord at fifth level and Over channeled.

Taking a moment to catch his breathe, Kirin moves in a diagonal toward to the left? trying to get closer to the demon lord while keeping Rhyana to his back for follow up, "I hope you're have a good heal," He shouts to her, "My next shot is going to backlash almost as bad it going to hurt him," 

Dex Save: 18

Damage: 60 Fire Damage

Overchannel so fireball will ignores resistance and immunity the Demon lord I assume has against Fire as well as maximum damage. 

Since there is no roll posted, I'm going to assume Kirin is averting his eyes in order to avoid the demon's gaze. That doesn't prevent him from casting his fireball, as he can simply target a point within range.

Three bolts of energy streak out from the darkness that envelops Kaylyn, striking the demon lord squarely in the torso as the patch of darkness withdraws further away.

Demogorgon DEX save v Fireball: 21 (saved for half)

Evoking powerful magic is Kirin's specialty, and he really overcooks this fireball to its fullest potential. A mote of flame fires from the staff and detonates in a huge conflagration that engulfs the demon lord... although as the flames clears, Kirin sees Demogorgon rise up from a crouch... seemingly having avoided the eye of the explosion.

Rhayna next

Rhayna hears Kirin and give him a big "OK!!" with her hand, then Kirin starts to prepare for his next action. Then he notices that Rhayna keeps going with her hand signal. Something about her doing something, and he has no idea what she is trying to tell him. Then next thing he knows, she moves toward the demon lord.

(I hope that Rhayna already moved 30 feet on her previous turn.) Rhayna moves to within 60 feet of Demogorgon, holds her Wand of Viscid Globs with both hands, and shoots a blob towards the Prince of Demons, then she quickly goes back to where she came from. (She is trying to disable at least one of his arm.)

Wand Ranged Attack: 39

(Woohooo!!!!)

In a characteristically impulsive burst of inspiration, Rhayna dashes forward and blithely points her drow-made wand at the enormous towering demon with shaking hands. Could this wand possibly work against a creature so large and so powerful? Does Rhayna hope for something miraculous, or does she simply act without hope, purely on a whim? The small black blob blurps out the quivering end of the ineptly-handled wand... such random and inexpert aiming is sure to miss... and yet somehow the blob sails straight, guided by mental acumen alone, scraping through the gaps between half-wrecked buildings and semi-crumbled stalagmites and strikes Demogorgon directly in the chest!

In a the first half-a-second the blob expands out to cover the demon lord's entire torso... another second passes and the black slime extends to the tentacles and legs... three seconds in and the viscid mass touches the cavern floor and begins to harden... and before the demon can lift an arm to resist, his upper limbs are pinned to his side leaving the four tentacled ends flailing, and his legs are sealed to the ground. Lolth's gifts are potent indeed!

Not in living memory has the Prince of Demons been shackled thus, held against his will, detained by a mere mortal! With eyes that burn with fury as deep as the infinite Abyss, Demogorgon swivels his two heads and glares at Rhayna with hatred and hunger, and his demonic terror explodes into Rhayna's mind like one of Kirin's fireballs...

Rhayna takes 13 psychic damage. Then please make a DC 23 Intelligence save.

Demogorgon is currently restrained.

Next up is Sekkar.

The two-headed monster seemed to be stunned! Perhaps, the attack was not that suicidal after all. Sekkar ran back and attacked again!

Attack: 20 Damage: 14

Attack: 32 Damage: 21

On attack that hit - Sneak Attack for 12 (all radiant)

BA: Cunning action - Dashing back, away from DG

(d10 help if needed: 2 )

Sekkar seizes the opportunity and sprints in to take another swipe at Demogorgon. Dawnbringer exults as she cuts into demonic flesh once more, but too late Sekkar realises the unwanted effect of his companion-sword's bright shining light - the sunlight is rapidly dissolving the restraining black goop! As Sekkar attempts to scurry back out of harm's way, one tentacled arm breaks free and swipes out at him...

Opportunity Attack: Tentacle v Sekkar
Attack: 25 Damage: 32 bludgeoning damage, then please roll a DC 23 CON save.

What happens next depends on the results of Rhayna's and Sekkar's saving throws...

Rhayna INT Save: 22

Reroll from Inspiration: 9

(LOL!!! Sorry for the delay.)

Rhayna prays to the Goddess to aid her aim, and aid she received. She holds her breath while the small black blog makes it way to its target, and it hits true. Upon seeing the results, she jumps for joy, like she has never done before. "Yeahh!!! Take that you big mean... Monster!!!"

Rhayna uses the left over movement to make her way back to closer to Kirin, but not too close.

Sekkar DC 23 CON save: 18 (and another with inspiration 21)

(In case still needed spell concentration DC19 24)

Drawing on every scrap of mental fortitude, Rhayna manages to barely avoid having her mind turned to jelly by the demon's powerful enchantment. And yet Demogorgon is relentless, and continues to fix his gaze on the courageous cleric, and the mental images don't cease to fill her mind.

The punishing blow of the tentacle is like nothing Sekkar has felt - even worse than the crushing grip of Orcus. Besides the bruised bones and scales, Sekkar feels like the very life has been dragged out of him...

----------------------------------------------------------------------

Demogorgon is no longer restrained.

Sekkar, besides taking the 38 damage, your hit point maximum is also reduced by 38.

Rhayna, please make a DC 23 Wisdom save or become stunned until the start of Demogorgon's next turn.
If Rhayna avoids being stunned, she can then direct the Couatl.

Meanwhile, let us proceed with Pax and Kaylyn.

ROUND 1: Rhayna 21, Demogorgon 19, Sekkar 16, Couatl 12, Pax 12, Kaylyn 10, Kirin 5.
ROUND 2: Rhayna 21, Demogorgon 19, Sekkar 16, Couatl 12, Pax 12, Kaylyn 10, Kirin 5.
ROUND 3: Rhayna 21

MAP:

Kaylyn continues her assault upon the Demogorgon by focusing her attacks trying to harm it as much as possible as more crackling energy is directed at the demon lord.

Attack: 16 Damage: 7 + 1 to roll Force damage 

Attack: 29 Damage: 12 + 10 to roll Force damage 

Attack: 20 Damage: 8 + 6 to roll Force damage 

Rhayna WIS save: 37

Rhayna will ask the Couatl to take the Dodge action for now.

(Darn. I believe the roll was 30, if it changes.)

Pax takes a deep breath, and then does what she's supposed to do, and rushes once more out into the fray.  She'd run a lot further than she'd thought during her momentary flight.  As she walks forward she weaves a spell.  The wind around the demogorgon begins to pick up and and seen rubble dust and debris are circling about him, rocks picked up and flung at the massive demon at where he stands. Moments later a Storm Sphere whirls about the demon, sending rocks and rubble flying into it. (DC 18 Strength save or 2 Bludgeoning damage.) As she strides forward (move 35 feet forward), she flicks her hand and a bolt of lightning explodes from the whirling wind towards the demon. Attack: 23 Damage: 11.  

Demogorgon STR save: 14 (that's a 27 in case it changes after editing)

Never before have the denizens of Menzoberranzan, the great underground city of the drow, seen a whirlwind... so they wouldn't know that they typically don't appear in spherical form... but for the first time a swirling vortex of wind appears in the heart of the city, centered on the demon lord. The flying rubble and debris troubles him not at all, but the bolt of lightning that crackles in the middle of the storm seems to give him a tickle.

More than a tickle though is felt from the triple blasts of energy that for the third time erupt from the dark circle where Kaylyn is concealed, with one blast striking Demogorgon right in one of his open mouths.

Rhayna seems to again be able to shake off the mental assault from the pair of eyes facing here, but another pair of eyes turns toward Kirin and bears down on his innermost fears and faults, making him feel weak and worthless...

Kirin, please make a DC 23 Wisdom save to avoid becoming stunned (or avert your eyes to avoid making the save, but if you do you cannot see Demogorgon until the start of his next turn)

Next up is Kirin (if not stunned) and Rhayna.

MAP: The sphere surrounding Demogorgon is difficult terrain.