Pickpocket (5e Subclass)
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Your roguish ways have taught you many things, but none as enjoyable as taking someone's items right off them. The thrill of being caught excites you, and drives you to do it more, and more. Perhaps you gain joy out of pickpocketing the poor and helpless. Maybe the rich dangerous game. Possibly the guards who protect you? There's a wide range that I'm sure you'll try around with.
Beginning at the 3rd level, when you gain this subclass, You can use your action to create a distraction. This distraction can only target one creature in particular. This can be talking to the target, making a loud noise of some sort, etc. While a creature is subject to your distraction, Sleight of Hand Checks are made with advantage. If a creature within 5 feet of you misses an attack, you can use your reaction to attempt a Dexterity (Sleight of Hand) Check. As long as the DM specifies they have loot to pickpocket. You can also use your cunning action bonus action to make this check on your turn.
- Planed Grab
Beginning at the 9th level, When you make a Sleight of hand check, you can specify what you're looking for. When you do this you gain proficiency in Sleight of hand, but cannot retrieve anything that isn't what you specified. If you are already proficient with Sleight of hand, you gain double proficiency. If you are already expertise in Sleight of hand, you add half your proficiency to the expertise roll instead. If the target does not have what you are looking for, the check fails, however you aren't discovered unless you actually fail the roll. At level 12 you may add your whole proficiency to the expertise skill.
- Light Fingers
Beginning at the 13th level, you gain advantage while putting items into others pockets. The items difficulty to place is of course of to the DM however logic says heavy, bigger things will be harder to place but smaller things will be easier. Once per long rest, you can replace and item with a similar size, and weighted one without notice. Performance checks made to switch an item on a weighted pressure plat do not need to be rolled with this ability. Additionally, coin purses, or even items in pockets can be timed and replaced. making a Sleight of hand check not necessary, given you have another item in its size and weight likeness. For example, a sheathed enchanted dagger can be replaced by an ordinary one, assuming there's no magical protection on the said dagger.
Beginning at the 17th level, You can now use your reaction to make Sleight of hand whether the attack hit or miss. If the attack was successful, you gain advantage on this check. While engaged in a conversation with someone, you can add your proficiency to Sleight of hand checks on that person. Deception checks are made with double proficiency if deceiving someone of someone else robing you. This check is rolled with advantage if the person said to be robing you has an item you own on their person. Additionally, when using the help action, you have advantage on Slight of hand check made on the target of that action. As well as creatures that you help out of prone. While you have a dagger drawn, and make a Sleight of hand check, instead of pickpocketing the target, you may deal your sneak damage. This can be performed any time you perform a Sleight of hand check. If you fail the check, the attack misses.