Tormentor

Of all other rogues, you are the simplest in nature, desiring one thing and one thing only: to inflict pain on your enemies.  You aren't concerned with theft or swords or death; you live to cause torment to your adversaries.  For you, it's not about life, death, money, or skill, it's about pain and only pain, of which you are a master; your craft is that of agony.  Many rogues follow the path of the tormentor for revenge against those who once harmed them and some develop the art for utility in other things, but all in all, a tormentor is simply a bringer of pain, for whatever reason he or she chooses.

Unfeeling

Starting at 3rd level, your heart has become hard and calloused toward suffering of any kind.  You gain immunity to the frightened condition.

The Art of Agony

When you choose this archetype at 3rd level, you become a master of manipulating the body for maximum pain and damage.  You deal an additional amount of damage with finesse weapons equal to your Dexterity modifier. In addition, checks made against restrained and/or frightened creatures gain a +2 bonus, or +4 if both apply.

Tools of Affliction

Starting at 9th level, you have learned to modify your weapons in cruel and violent ways, forming them into purely sadistic tools.  Choose one weapon to apply this to, which becomes a Tool of Affliction.  At any time, you can spend eight hours modifying a weapon to grant it the Tool of Affliction trait as well.  All creatures hit with a Tool of Affliction must make Constitution save with a DC of (8 + proficiency + Dexterity modifier) or else suffer a d8 bleed effect (e.g. at the start of every turn still bleeding, the creature suffers 1d8 necrotic damage).  This bleed effect continues until the creature receives magical healing or makes a Wisdom (Medicine) check with a DC of (8 + proficiency + Dexterity).

Abominable Acts

By 13th level, the torment you meet out can have additional, vile effects on your victims. You gain a pool of Abominable Acts equal to your Charisma modifier, which resets every long rest. When you deal damage to a target, you may spend one Abominable Act to activate one of the following effects on the target.

Dominance. The target must make a Charisma saving throw against a DC equal to (8 + proficiency + Charisma modifier). On a failure, you have advantage on all checks made against the target for the next minute.

Nerve Strike. The target must succeed on a Constitution saving throw against a DC equal to (8 + proficiency + Dexterity modifier) or become stunned. At the start of each of their turns, the target may remake the saving throw, ending the effect on a success.

Fearful Presence. The target must succeed on a Wisdom saving throw against a DC equal to (8 + proficiency + Charisma modifier) or become frightened for 1 minute. At the start of each of their turns, the target may remake the saving throw, ending the effect early on a success.

Touch of Madness

When you reach 17th level, you have become so adept at causing pain that your victims' minds may break under your work.  Whenever you knock a victim unconscious, they must make a Wisdom saving throw against a DC equal to 8 + proficiency + Charisma modifier; on a failed save target gains a Madness Point.  Madness Points last 24 hours before disappearing and they cause a variety of effects depending on how many Madness Points a creature has at one time.  1 Madness Point causes a creature to become frightened of you.  2 Madness Points cause short-term madness.  3 Madness points cause long-term madness.  4 or more Madness Points cause indefinite madness.