Become A Highwayman.

This mod allows you to roleplay as a highwayman character. Stop unsuspecting travelers along the road and demand their gold and valuables.

You can only rob travelers, farmers, and other people who live outside the cities in Skyrim.
I am working on an optional mod that lifts the restrictions, and lets you rob anyone except children and guards (unless you want to end up in jail).

There are two different reactions:
Scared - Will give you their valuables in exchange for their lives.
Brave - Refuses to be intimidated, and challenges you to a fight to the death.

You will instantly become enemies with anyone you rob.
You will earn an increase in speechcraft if you intimidate someone into giving you their valuables.
Since the crimes happen outside the cities and towns of Skyrim, the guards are not notified and you won't receive a bounty.
Those people you let live have a good chance to call the dark brotherhood or bandit thugs to go after you.

 Become Highwayman version 2.0 - Now available for download!
This is an update of the voiced version that features Bandit Gear.
Those wearing the new bandit gear will fool the bandits into thinking you're one of them.
If you are in a bandit camp, do not unequip the bandit gear unless you are ready to fight.
Without your bandit gear, the bandits will know that you are not one of them.
I would advice equipping the bandit gear before entering a bandit camp. Once they
start fighting you, they won't stop even if you equip the gear.
The gear can be crafted at the forge under the Hide section. It can also be tempered.

original mod for LE
https://www.nexusmods.com/skyrim/mods/37545

All credit goes to MimiTheAlchemist the creator of the mod
permission here https://mimithealchemist.tumblr.com/