Secret Agent

You are a Secret Agent - master of deception, effective at skirting security measures, and deadly in combat.  Charismatic and cunning, adept at improvisation in both conversation and combat, and equally comfortable at home and in far away lands, you always complete your mission.  Typically a Secret Agent has the backing of a large organization such as a wealthy family, business conglomerate, or regional government, but is always given the latitude to carry out his missions as he sees fit.

For as long as you are backed by your organization, you may live at a Wealthy lifestyle at no expense to you.  But be careful - get caught or otherwise compromise yourself, your position, or your backers, and you will surely be disavowed and cut off!

Work with your DM on a supply of clothing, weapons and armor, or other gadgets or trinkets your organization might see fit to supply you with.

Improved Improvised Weapons

A Secret Agent is a master of improvisation, including using ordinary or otherwise non-weapon objects as weapons.  Starting at level 3, as with the normal Improvised Weapons rule, if an improvised weapon is similar to an existing weapon, you may apply your proficiency bonus and use the stats of the weapon for the improvised weapon; however, you may do this for any weapon type, not just those you are already proficient with.

If you use an object that bears no resemblance to a weapon, it instead deals 2d4 damage plus your Dexterity modifer. If you use a ranged weapon to make a melee attack, or throw a melee weapon that does not have the thrown property, it also deals 2d4 damage plus your Dexterity modifer. An improvised thrown weapon has a normal range of 20 feet and a long range of 60 feet.  This damage is increased by 1d4 at levels 9, 13 and 17.

Additionally, you may wield light improvised weapons in each hand and apply the Two Weapon Fighting rules to them.

At level 13, this extends to improvising traps using any spare objects around you.  If you take 10 minutes, you may create a simple mechanical setback (at your level) from spare bits of string, strips of metal, toothpicks, tube socks, or other appropriate objects (duct tape) that might be lying around.  See the trap rules for setback save DC and damage severity by level.

Master of Disguise

A Secret Agent is a master of disguise, whether physically, mentally, or emotionally.  You are able to disappear into crowds, talk your way past a guard, pass as another, or change the minds of others.  At level 3, you may choose a skill proficiency in either Deception or Persuasion, or a tool proficiency in Disguise Kit.  If you are already proficient, you may choose expertise in it.

Expertise in Deception

Expertise in Deception

Expertise in Disguise Kit

Expertise in Disguise Kit

Expertise in Persuasion

Expertise in Persuasion

Proficiency in Deception

Proficiency in Deception

Proficiency in Disguise Kit

Proficiency in Disguise Kit

Proficiency in Persuasion

Proficiency in Persuasion

Close-Quarters Combat Training

Your training has included close-quarters combat training, preparing you for grappling with opponents.  Starting at level 9, you may now make either an Athletics or Acrobatics check to begin a grapple, and you do so with advantage.  The same applies when an opponent attempts to grapple you, when the opponent attempts to escape from your grapple, and when you attempt to escape an opponent's grapple.

Additionally, you may begin or escape from a grapple with an opponent two sizes larger using either an Athletics or Acrobatics check, though you do so at disadvantage and must have two free hands instead of just one.

Sleeper Hold: If any opponent grappled by you fails their check to free themselves two rounds in a row, they fall unconscious for one minute, following the effect rules for Sleep, except this ability is not magical - creatures immune to magical sleep may be affected.  Check with your DM to determine whether the creature you put into a sleeper hold has an appropriate head/neck area that would be affected by this ability.

Surprise Attack

A Secret Agent is especially skilled at striking unaware opponents to great effect.  Starting at level 13, double your Sneak Attack damage if you strike while hidden.

Charming

A Secret Agent is a smooth operator on and off the battlefield, natural charisma flowing from every pore.  At level 13, you may cast Charm Person as a 1st-level spell, using Charisma as your spellcasting modifier.  At level 17 you cast it as a 2nd-level spell.  You may cast it twice per long rest.  If the target succeeds the save, you may not attempt to cast this spell on them again for 24 hours.

Your Reputation Precedes You

Every good Secret Agent reaches a point in their career when they are no longer so secret.  Even if the nature of your character is elusive, stories of your exploits have spread through the circles of information brokers, governments, villains and their henchmen, and the social elite (and perhaps even further).  Whether exaggerated, underplayed, or completely wrong, these stories give you an advantage in your dealings with the people who have heard them.  At level 17, when dealing with anyone who may know your reputation, you have advantage on any skill checks based on Charisma.  Additionally, you have advantage on your Initiative roll if you enter combat with an opponent who may know your reputation.