Ipkesh

Ipkesh is a cambion who runs a tavern in the City of Dis. As an NPC, Ipkesh is played by Matthew Mercer.

Appearance
Ipkesh is a very handsome-looking man with deep red skin and long black hair that goes past his shoulders, turning gray at the tips. He has horns protruding from his forehead and a pair of wings. He wears a dark black and gray cloak.

Vox Machina first encountered Ipkesh upon entering a tavern in the City of Dis. He was sitting at a table by himself, drinking from a goblet and looking lost in thought. As Vox Machina spoke to another bar patron, Ipkesh turned and watched the exchange. Vox Machina then rented three rooms and went upstairs.

Percy and Grog went downstairs to gather some information, and found Ipkesh still at his table, quietly talking to a small impish creature on his shoulder. The imp flew off as Percy and Grog entered the room. The devil looked up at the two of them, pouring more wine into his goblet. Percy walked over to the devil and asked to speak with him. The devil accepted and invited them to take a seat, which they did. The devil poured them both a drink and they exchanged names: Ipkesh, Freddie, and Greg.

Ipkesh asked what their business was and Percy told him they're looking for a rakshasa. He asked the devil about the prison, if he knew how to get them in there, or someone who did. Ipkesh said there was a price for his information. Ipkesh snapped his fingers and the area around them went dark. He said that they could speak freely now. Ipkesh proposed a contract: he would tell them what he knew about the prison and even help them get in. In return, they would kill Utugash, the devil that Ipkesh worked for. If Utugash was taken out, Ipkesh and his friends could rise up in the devil hierarchy. Some of these friends worked in the prison, and Ipkesh would make sure that Vox Machina were safely arrested and placed with these allies, should they complete their end of the deal.

Percy told Ipkesh that he needed to confer with the rest of the group before agreeing to anything. The devil understood, and warned them of the Whispers: the armored imps flying through the sky. They reported to the archdevil himself. Percy assured Ipkesh that he would not speak his name in public. Ipkesh dispersed the sphere of darkness around them. The two mortals finished their drinks and headed back upstairs.

Vox Machina returned to the bar, and found Ipkesh at the same table, drinking a goblet of wine. Ipkesh nodded at the group when he saw them. There was a piece of paper on the table in front of him. He requested that they read it and let him know if they needed to make any revisions. Percy and Tary read the contract out loud to the rest of the group.

Only one person needed to sign the contract, and only the first pact needed to be completed; the second and third pacts could be triggered later by the recipient, but doing so was completely optional.

Percy thought the first pact could use some more negotiating, and he would like to think it over a bit longer before signing anything. Ipkesh understood, telling Percy to come back when he was more certain of what he wanted out of the contract.

Later, Grog headed downstairs for a meal, and saw Ipkesh seated at the bar and talking with the bartender. When Grog requested his meal, the bartender glanced at Ipkesh and gave it to Grog for free.

Later Vox Machina headed down stairs, and saw Ipkesh was back at his original table, no wine glass this time, but the contract paper still rested in front of him. Percy and Ipkesh then negotiated a series of amendments. Two were agreed upon: That Ipkesh would provide a guide for them, and that their equipment would not be taken from them. Other suggestions were also made, but ultimately refused. Percy also clarified what would happen to his soul should he die while completing the contract. If the deal was completed, regardless of Percy’s own survival, his soul remained his own. If the deal was broken, Ipkesh claimed his soul. Ipkesh then wrote the amendments into the deal.

Grog showed Ipkesh a ring with the symbol of Asmodeus on it. Ipkesh told them it was the signet of the Cult of Asmodeus. It didn't mean much within the Hells, but on the Material Plane it was used to assert belonging. Percy had one last question: how powerful was the devil they woud be assassinating? Ipkesh explained to the party Utagash’s strengths and the forces he commanded, and stressed caution.

Percy then signed the contract with Ipkesh. The deal complete, Ipkesh took the contract. He summoned an imp named Vasa and explained that they would be their guide. Ipkesh told Vox Machina to rest and prepare for their mission, advising them to be stealthy. Percy asked if he could get them a Silence spell; he could provide one or two. He warned them that Utagash’s assasination would alert the guards, and encouraged Vox Machina to kill them too.

The next morning, Vox Machina went downstairs and found Ipkesh sitting alone in the tavern, with Vasa sitting on his shoulder. The devil told them that Vasa was a master of not being seen and would lead them where they needed to go, however the imp would not help them in battle. Ipkesh then provided a Silence spell scroll to the group, as well as some parting advice.

As Vox Machina were dragged through the streets in chains, Vex briefly saw Ipkesh in the crowd. He smiled at her, gestured for her to be quiet, then disappeared back into the crowd.

Trivia

 * Ipkesh is the reason why Percy's youngest daughter, Gwendolyn, is a tiefling, since his deal with her father marked the de Rolo bloodline. Gwendolyn shares Ipkesh's red skin and the black hair with gray tips.
 * Since Ipkesh is a devil of Dis, it's very possible that Gwendolyn will eventually manifest magic related to this legacy, such as the Thaumaturgy cantrip and the Disguise Self and Detect Thoughts spells.