(That makes sense.)

Disadvantage roll: 12

(The only reason I thought about it is because I play a lot of rogues, lol.  They're probably my favorite class.)

(Just to inform you guys, what Gynugri does is part of his racial traits. You can check it if you click the campaign link on you character sheet.)

(Oh I know.I play a goblin in another campaign.)

The sailors finish loading their crossbows, and begin to fire. Not a single one misses their mark, and half the pirate crew get crossbow bolts in them. One of the hit pirates keels over, clutching a crossbow bolt in his heart, but the rest are fine(ish).

Grig pulls out his shortsword and goes to work on the Big Pirate, hitting him once with his longsword and stabbing him with his shortsword. The Big Pirate clutches his side, blood streaming down his everywhere.

The pirates retaliate, firing upon the sailors with their own crossbows. They do not share the same accuracy as the sailors, only two of them hitting. One of the sailors however, got a crossbow bolt deep in her side, and though she isn't down, she looks pretty bad.

The pirate captain(who should have gone earlier but didn't because the DM is forgetful) fires a heavy crossbow at Tab, missing him by a smidge.

Ortimay deals the finishing blow to the Big Pirate, neatly slashing his head off and booting him overboard.(Wow I didn't expect him to go down so fast)

The two Brutish Pirates fire their crossbows. One misses the pirate captain, and the other barely clips a sailor.

(Nobody(unless you preposted I may have missed that.))

(No. I should've though. My bad. Here it is though.)

Nobody scrambles back to the other side of the mast and away from the action. And if he can make it there safely, he'll start singing with his booming voice and wave his staff behind the pirates. 

"Go to sleep~ *ugh*...  Go to sleep~ Go to sleep mean... oh goodness.. my stomach... sleep 'ol pirates~" 

Sleep: 23 centered fifteen feet behind center pirate to hopefully catch them all.

When it comes around to Tab's turn, he'll shout over his shoulder at Melanthios, "Cover me!"

Tab will shimmy across the grappling rope, and attempt to leap onto the deck between the pirate at the opposite end of his rope and the pirate captain. Acrobatics: 18

Gene will reposition himself somewhat towards the front of the ship and take a shot at anything that's not asleep, prioritizing a possible killshot over a fully healthy target. Attack: 19 Damage: 4

Gynugri appears from the shadows and casts a numbing spell at the nearest brutish pirate to him before attempting to hide behind the mast.

(I've been steadily confusing myself, so I'm not sure if Melanthios has a turn locked in or not.)

(I don't think he does.)

Quote from Mehmen >>

(No. I should've though. My bad. Here it is though.)

Nobody scrambles back to the other side of the mast and away from the action. And if he can make it there safely, he'll start singing with his booming voice and wave his staff behind the pirates. 

"Go to sleep~ *ugh*...  Go to sleep~ Go to sleep mean... oh goodness.. my stomach... sleep 'ol pirates~" 

Sleep: 24 centered fifteen feet behind center pirate to hopefully catch them all.

 

 (I'm not entirely sure which pirate would be the center pirate, please elaborate.)

(The one right across from him and the sailor. )

(Sleep has a 20 ft. diameter, not radius. If you did that, you would hit no one.)

Melanthios will shoot at one of the brutish pirates.

If he is still hidden: Piercing Attack: 18 Damage: 21

If he is not: Attack: 15 Damage: Unable to parse dice roll.

If he can hide again (I'm guessing it would be with disadvantage): 14

(Huh. That's way smaller than I thought. Okay, same center most guy that I mentioned, but close enough it'll hit only him and the closest pirates too him without affecting our ship.)

Nobody casts another sleep spell, and 3 pirates close their eyes and fall over(Italics).

Tab shimmies across the rope and puts on a burst of speed, rushing at the pirate captain, the pirate he breezes by stabs at him, but misses. He punches the pirate twice, and an audible crack is heard as blood runs out of the captain's now misshapen nose. Mel fires an arrow nearly through one of the brutish pirates, which kneels and spits up blood, but stays alive. The pirate captain strikes out at him, hitting for 6 damage(Ow). Gynugri waves his hand, and frost forms on the brutish pirate with an arrow through him. He shakes off the frost however, and continues with his bleeding everywhere. Gene flies above Captain Ortimay(Underlined), and fires at the near dead brutish pirate. It hits him in the foot, pinning it to the floor. He still stands(Well, he can't sit without sawing his foot off).

The sailors let off another round of bolts, and another pirate goes down.

Grig climbs across the grappling hook and slashes at the pirate at the end of it. He does a magic trick. First there was 1 pirate. Now there are 2!

Two of the pirates run to wake up some of their sleeping comrades. One fires upon a sailor and the other slices at Grig. Both miss.

Ortimay fires at the near dead Brutish Pirate, and hits it, STILL NOT KILLING IT! Seriously, someone put this guy out of his misery!

One of the Brutish Pirates fires his crossbow, missing a sailor by a mile. The other tries to aim at Gene, but falls over, unconscious and bleeding. The crossbow falls to the ground and goes off and hits Gene in the side, dealing 10 damage.

(Nobody)

(Wait, who did the captain attack?)

Also, here's my preloaded turn (actually going to remember I have one this time):

Melanthios will shoot at the hulking pirate.

If he has advantage from stealth: Piercing Attack: 21 Damage: 27

If not: Attack: 23 Damage: 8

If he can, he will re-stealth (with disadvantage): 17

After Nobody goes, Tab will continue his barrage on the Pirate Captain - still doing non-lethal damage, in an attempt to subdue and capture rather than kill. 

Attack: 12 Damage: 5

Bonus attack: Attack: 21 Damage: 6

Tab won't move this round, resetting his Feline Agility ability. 

What's the initiative order exactly?