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"Good luck halfling."

Also, Doughbert will take a piece of cloth and wrap it around his mouth and nose, because he expects it may be quite ripe smelling in there if the remains of that beast we tossed into the portal is still there.

As Shybolt edges closer to the portal, and peers cautiously at the strange elven writing and rune, Brother Arven will calmly say "A journey is begun with a single step." then contemplating the backside of the halfling, "But sometimes a journey must be forcefully stated with a kick."

(Edited to reflect the DM's statement above)

"I think I'm strong enough to hold the halfling. Grumm, maybe you should be ready in case something else comes back out of the portal."

Timorel will take a seated position next to the wall that allows him to lean into the wall to brace himself with his feet. He'll drive two iron spikes into the floor to put his feet against.

Brother Arven takes the door, he will stand just inside and spasticly move my head from left to right trying to watch the darkness for approaching critters .
He is prepared to shut the door quickly if needed.

Timorel saw Shybolt vanish as he stepped inside the circle, but the weight of the halfling on the end of the rope reassured Timorel that he was still there.

Shybolt found himself in a dark, round pit, which put him in mind of a well. He thought he could see light reflected from below, perhaps twenty feet down... it appeared the hole was indeed a well.

Taking a moment to look carefully, Shybolt saw no sign of movement below, so he descended further. About ten feet down, the hole opened out; the space below was apparently a room of similar size to the one above.

What is Shybolt using for light?

A torch. Thats all he has.