I just had a long and exhausting semester and a friend of mine, who just recently got into DnD, and was had a 5e campaign in mind. However he got a different group together to give it a try first. He knew i was staying in town for the summer so he asked if I would like to join in. How could I refuse?
The campaign was a hero's guild that takes in orphans and trains them to protect the world and as soon as I heard that I knew what I wanted to play. Now as I said before I just finished a stressful semester in school so I wanted to play a character to relieve that stress. I designed the most evil and psychotic warlock I could. I asked him if he would allow this. Just because my character was going to be a scumbag doesn't mean I am.
He allowed under the pretense that no organization is perfect and sometimes when creating heroes you will occasionally make a villain. With his blessing I went all out. My character had sold his soul to Asmodeus when he was about 5 and was never sane to begin with. He just knew how to hide it long enough to graduate from the academy.
Upon graduation we were put into a party and given free reigns. Our group consisted of me (a half elf warlock), a tabaxi ranger (who i deemed as my pet), a dragonborn barbarian, a paladin, and for the life of me I can't remember the other 2. The guild also gave us a very handy seal. This seal was proof we worked for the hero's guild, allowed us to teleport back to the organizations main headquarters, and allowed us to communicate with our party members like walkie talkies.
Our first job was to take care of a group of bandits that were a growing problem and the clients feared they would soon become a new faction. During the early part of this mission we split up into groups of 2 for recon. Because we knew the dangers of splitting the party we agreed that at the first signs of a fight we would flee and meet up at the camp sight. Along the way the barbarian contacted the group with a report saying he might have found a way to get to the bandits base. I was the first to reply back and in the deepest voice I could I replied "This is lord Asmodeus. How can I help you?" Everyone laughed, but the DM could see the wicked grin that appeared on my face.
"What?" He asked.
"I want to roll deception to make him think it's Asmodeus" I replied.
The laughing stopped as my wicked grin increased. The DM busted out laughing. He wanted to see where this would go as much as I do. I got a nat 20 and the barbarian got a nat 1. Not on did he believe my rouse, but ruse but became terrified. As far as he was concerned he was talking to the lord of hell and he just hung up. I continued this for the rest of the session sowing fear into the heart of our rage machine called a barbarian.
After the session I pulled the person playing the barbarian to the side and apologised for my shenanigans.
"Did you do it because you were in character or for another reason?" He asked me. As far as I was aware he was a first time player, which is why i wanted to apologise.
"I was in character" I replied truthfully. He then laughed.
"In that case we were good."
"If you think I ever get carried away with this and you want me to stop, just let me know." I told him before I left.
I kept doing this for about 2 more sessions. Everytime he answered the walkie talkie I would keep this up but with some changes to make it seem more plausible, such as "This is Lord Asmodeus' Secretary. Can I help you?" or "You called hell. Condeming souls since the beggining of time. How can take yours today?" but most of the time it was the simplest "This is Lord Asmodeus how can I help you?"
When we took out majority of these bandits, and their organization, we split into 2 groups to hunt down the the survivng bandits. We thought it wasn't a bad idea since together there were about 6 of us and we were all about level 8. Along the way the barbarian got separated from his group and when he was done fighting the last of the bandits he called in to reconvene with us.
There was hesitation in his voice. The barbarians player looked at me as he was thinking of what to say. His eyes were pleading for mercy but the faint trace of a smile told me he was excited with anticipation for what was going to happen. Our DM picked up on this and told him that he had his back. With that the barbarian asked where we were through the walkie talkie and before anyone could say anything our DM asked for initiative.
His solution for stopping me was an initiative role, but sadly I was the only one that got a nat 20. The unholy gods of the dice were once again on the side of evil.
"It's about **** time you contacted us?" I cursed and I kept cursing him out, with my language getting more and more vulgar. I could here the sigh of relief from across the room that the barbarians player made and everyone thought I was done with the joke. We went to the city to collect our reward. I said I would pick it up and the rest of the party trusted me. The only one that stayed with me was the ranger (who was officially my pet at this point), the gullible fools. Despite all the torture, mind control, and other horrors/atrocities I've commited, they still trusted me. Though I guess that was evident when our holier than though paladin started turning his back when I did these because I showed results, and never told the barbarian i was messing with him. everyone knew but I think their characters were to scared to spoil my fun.
When I got to the client he said he will pay us when everyone was here. Obviously the DM was smart enough not to trust my character. I called it in and everyone responded, with the barbarian being the last one to respond and even told me where he was coming from. I couldn't resist. I had to do it one last time and as I did this i even openly said (out of game) that this would be the last time.
"Hello Leonidas, This is your Lord and destroyer Asmodeus. What can I do for one of my favorite customers." I said in the usual deep voice and a nat 20 later he believed it. He said his character fell into the fetal position and just cried. The DM, the player, and I all busted out laughing while everyone else facepalmed and occasionally chuckeled. After we all got it out of our system, the player wiped a tear from laughing to hard away and i got back into my chair (fell out from laughing to hard) and stopped coughing, we continued. I told two of the guards our last member is lost and could be found in the market square having the panic attack.
They found him and carried him to the meeting. Surprisingly enough that session cemented my friendship with that player and he still plays when he has the time. To this day I have never come close to anything like that again and the name of that warlock became a term we coined for having almost every stat be a 20 or doing so unpredictable no one could have predicted it.