"What happened to your first husband?"
"Oh, it's terribly sad. He died of food poisoning after I gave him a plate of mushrooms for dinner."
"And your second husband?"
"The same. Plate of mushrooms. Food poisoning."
"And your third husband, did he die of food poisoning as well?"
"No, he died of head trauma. He wouldn't eat the mushrooms."

Quote Originally Posted by Handsome Malcom
Handsome Malcolm

Spoiler: Wedding Night
The woman closed the door and turned around, then walked over to the bed where her husband was already getting undressed. She took a moment to admire his body, still lithe despite his five decades of age, and smiled.

When her previous husband died last year, she'd been sure she'd never find love again. But then, just months ago, she'd met Walter, and that had been the start of their whirlwind romance.

"Martha, do you love me?" he asked in that sexy, sexy voice of his. The woman smiled and undid her dress's straps.

"Of course I do, Walter. Why do you ask?"

The man didn't reply, but his expression grew more serious, and a frown appeared on his face. Martha opened her mouth to ask again, but then she saw it.

Walter was changing.

His nose, straight and spotless a moment before, twisted and fused with neighbouring flesh until it was little more than a bulge in his face with two ragged holes in it. His upper lip split, revealing a row of dirty teeth. His back contorted until he was sitting in a horrible hunched position, and with a sickening sound his limbs dislocated.

"And now, Martha?" the terrible creature whispered from its mouth-hole. "Do you still love me?"

She shrieked and leapt backwards, her left hand raised in front of her as the other one began to feel around for the doorknob.

"Who are you? What are you?" she screamed.

The thing in front of her twisted its face even further, into something completely incomprehensible, and, with a great leap, closed the distance between the two of them in seconds.

Martha felt something sharp poking her throat, followed by a jolt of pain, followed by nothing at all.

She failed to notice the tear making its way down her husband's face.

Malcolm, the Black Widower

NE Middle-Aged Silverbrow Human Sneak Attack Zhentarim Soldier Thug Fighter (Skilled City-Dweller) 9/Chameleon 1/Twisted Lord 10

Spoiler: Ability scores
Malcolm starts with the following scores, adjusted for being middle-aged.

STR: 10
DEX: 12
CON: 10
INT: 14
WIS: 12
CHA: 18

Malcolm increases charisma at level 4, 8, 12, and 16. At level 20 he increases strength instead.

Spoiler: Build table
Level Class Base Attack Bonus Fort Save Ref Save Will Save Skills Feats Class Features
1st Sneak Attack Thug Fighter 1 +1 +2 +0 +0 Bluff 4, Craft (Poisonmaking) 4, Disguise 4, Intimidate 4, Sense Motive 2, Spellcraft 2 Able Learner, Combat Expertise Sneak Attack +1d6
2nd Sneak Attack Thug Fighter 2 +2 +3 +0 +0 Bluff 5, Craft (Poisonmaking) 5, Disguise 5, Intimidate 5, Skill Trick (Second Impression) 2 - -
3rd Zhentarim Soldier Sneak Attack Thug Fighter 3 +3 +3 +1 +1 Bluff 6, Craft (Poisonmaking) 6, Disguise 6, Intimidate 6, Sense Motive 3, Spellcraft 3 Craven, Skill Focus (Intimidate)B Sneak Attack +2d6
4th Sneak Attack Thug Fighter 4 +4 +4 +1 +1 Bluff 7, Craft (Poisonmaking) 7, Disguise 7, Intimidate 7, Skill Trick (Assume Quirk) 2 - -
5th Zhentarim Soldier Sneak Attack Thug Fighter 5 +5 +4 +1 +1 Bluff 8, Craft (Poisonmaking) 8, Disguise 8, Intimidate 8, Sense Motive 4, Spellcraft 4 - Extended Intimidation, Sneak Attack +3d6
6th Sneak Attack Thug Fighter 6 +6/+1 +5 +2 +2 Bluff 9, Craft (Poisonmaking) 9, Disguise 9, Intimidate 9, Skill Trick (Never Outnumbered) 2 Imperious Command
7th Sneak Attack Thug Fighter 7 +7/+2 +5 +2 +2 Bluff 10, Craft (Poisonmaking) 10, Disguise 10, Intimidate 10, Tumble 2 - Sneak Attack +4d6
8th Sneak Attack Thug Fighter 8 +8/+3 +6 +2 +2 Bluff 11, Craft (Poisonmaking) 11, Disguise 11, Intimidate 11, Tumble 4 - -
9th Zhentarim Soldier Sneak Attack Thug Fighter 9 +9/+4 +6 +3 +3 Bluff 12, Craft (Poisonmaking) 12, Disguise 12, Intimidate 12, Tumble 6 Quick Draw Sneak Attack +5d6, Swift Demoralization
10th Chameleon 1 +9/+4 +6 +3 +3 Bluff 13, Craft (Poisonmaking) 13, Disguise 13, Use Magic Device 3 - Aptitude Focus
11th Twisted Lord 1 +9/+4 +6 +5 +3 Bluff 14, Craft (Poisonmaking) 14, Disguise 14, Intimidate 14, Tumble 10, Use Magic Device 4 - Twisted Form
12th Twisted Lord 2 +10/+5 +6 +6 +3 Bluff 15, Craft (Poisonmaking) 15, Disguise 15, Intimidate 15, Move Silently 1, Tumble 15 Practiced Spellcaster (Chameleon) Sneak Attack +6d6
13th Twisted Lord 3 +11/+6/+1 +7 +6 +4 Bluff 16, Disguise 16, Hide 1, Intimidate 16, Move Silently 2, Tumble 16, Skill Trick (Timely Misdirection) 2, Skill Trick (Group Fake-Out) 2 Improved FeintB
14th Twisted Lord 4 +12/+7/+2 +7 +7 +4 Bluff 17, Disguise 17, Hide 4, Intimidate 17, Move Silently 5, Tumble 17 - Peripheral Invisibility
15th Twisted Lord 5 +12/+7/+2 +7 +7 +4 Bluff 18, Disguise 18, Hide 7, Intimidate 18, Move Silently 8, Tumble 18 Craft Wondrous Item +7d6 Sneak Attack
16th Twisted Lord 6 +13/+8/+3 +8 +8 +5 Bluff 19, Disguise 19, Hide 10, Intimidate 19, Move Silently 11, Tumble 19 - Improved Demoralize
17th Twisted Lord 7 +14/+9/+4 +8 +8 +5 Bluff 20, Disguise 20, Hide 13, Intimidate 20, Move Silently 14, Tumble 20 - Twist Target
18th Twisted Lord 8 +15/+10/+5 +8 +9 +5 Bluff 21, Disguise 21, Hide 16, Intimidate 21, Move Silently 15, Tumble 21 Surprising Riposte +8d6 Sneak Attack
19th Twisted Lord 9 +15/+10/+5 +9 +9 +6 Bluff 22, Disguise 22, Hide 19, Intimidate 22, Move Silently 18, Tumble 22 - Twist Perceptions
20th Twisted Lord 10 +16/+11/+6/+1 +9 +10 +6 Bluff 23, Hide 23, Intimidate 23, Move Silently 22 - Twist Mind

Spoiler: Spells
From level 10 on, Malcolm can cast 4 level 0 spells, 3 level 1 spells, and 1 level 2 spell while his arcane focus is active.

His spellbook should at the very least include Absorb Weapon, in addition to whatever spells are needed for crafting.

Spoiler: Fluff
Malcolm begins his career as an attractive young thug working for various shady organizations, including the Zhentarim. He may not be physically intimidating, but he's good at sticking swords in vulnerable parts and can be of great help when some arms need twisting. After working side-by-side with a variety of minions and employers for decades, he's picked up a handful of their skills, including some assassin magic.

It is then that the Ebon Cabal approaches him, offering power untold in exchange for a few completed missions. True to their word, they grant Malcolm the promised skills, but at a horrible price: his beautiful face he once prized is disfigured forever, and even though he could disguise it, doing so feels wrong, as if he is just loosely draping another person's skin over himself.

Malcolm's wife, a former partner of his he ended up marrying, initially knows nothing about his condition, unaware he feels nothing but revulsion when her presence forces him to assume that twisted body he once called his.

It is then that all goes wrong.

In one of the moments that Malcolm briefly assumes his more comfortable shape, he is spotted by his wife. Not realizing what she's looking at, she responds with force to the unfamiliar intruder in her home.

Malcolm, already nervous, strikes back blindly, and before he knows it his wife is dead. As he watches her breathe her last, something snaps in his mind.

Malcolm disappears, and what happens next is unknown. Some say he returned to the Ebon Cabal, seeking the company of those few who'd accept his deformity. Some say he killed himself. Some say he journeyed to distant, empty lands, where he lived out the remainder of his days by himself.

Unfortunately, the truth is far more gruesome.

Using his skill at disguise magical and mundane, Malcolm has become a many-faced killer, seducing many, then killing them as they unfailingly reject his monstrous form. Their wedding rings he takes and turns into razor-sharp blades, some of which he conceals within his own body.

Now, the Black Widower is a feared assassin who is both an unpredictable combatant whose impossible feints leave his target's defenses wide open, and a terrifying manipulator who can leave even the toughest foes broken and cowering messes.

Spoiler: Level 1-5
Malcolm begins play as a pretty standard fighter, albeit one with a strange skill-set. At these levels, just run up to things and stab them, preferably from flanking positions. Out of combat, you can contribute with your not inconsiderable bluff, intimidate, and disguise scores (remember, Malcolm has 18 charisma!). If you can spare the money, crafting some poison should also help the team.

Spoiler: Level 6-10
Now we're talking: not only does Malcolm pick up the wonderful Imperious Command, he also gets Swift Demoralization and Never Outnumbered, completing the holy trifecta of intimidation.

He also gets some slight spellcasting from Chameleon, currently pretty insignificant but hugely important in the future.

Spoiler: Level 11-15
Welcome to the special ingredient! Malcolm can now turn into a form that grants bonuses to feints and intimidation attempts, in which he spends as much time as possible. The events of his tragic backstory occur somewhere around here, giving Malcolm a good reason to switch from blades to poison rings (also, enemy AC starts getting too high to keep up with).

Speaking of feints, Malcom gets two skill tricks that boost them further.

Sneak Attack gets further advanced, and Malcolm gets his third attack a round, making those full attacks even deadlier.

This is also the time where the build's main routine becomes available, which combines the three things Twisted Lord wants you to do (Sneak Attacking, Feinting, and Intimidating) in a single round. How, you ask?

Well, that's all thanks to two small feats we got. Practiced Spellcaster raises Malcom's Chameleon CL enough to qualify for Craft Wondrous Item, which combined with his virtually limitless access to every 2nd-level or lower spell allows for quite a bit of item creation.

We're going to use it for something easier, though: Pearls of Power. The 2nd-level version is 2000 GP to make, and there's no limit on the number you can employ in a day. We're going to use it to cast a specific spell over and over again during.

What spell, you ask? Absorb Weapon from the Spell Compendium. You may already realize what I'm getting at here. If not, feel free to look it up.

That's right: free action feint attempts as long as we draw the absorbed weapon in the round we attack! Four PoPs let us hide a weapon all day long, so we don't need more than twenty or so pearls: easily affordable by now.

To summarize, Malcolm's intended action sequence looks like this now:

Free: Draw absorbed weapon.
Swift: Intimidate, potentially causing foes to be Cowering. Never Outnumbered may be used as well.
Free: Feint with a huge bonus against priority target that isn't cowering, using Group Fake-Out if necessary.
Full-round: Full attack, most likely with Sneak Attack thrown on.

In any rounds that follow, drop your weapon as a free action, immediately draw a new one, and repeat.

Spoiler: Level 16-20
Four attacks per round now. In addition to all the earlier awesomeness Surprising Riposte turns your feints into round-round debuffs the entire party can profit from, in addition to giving you even more opportunities to sneak attack.

The various Twists provide some more options, and are definitely valid uses of your action if you find yourself near any shaken foes.

Spoiler: Magic items
As said before, Malcolm uses Craft Wondrous Item to create Pearls of Power for himself.

In addition, the feat allows him to enchant his poison rings, give himself ability and skill bonuses, and create useful minor utility items.

I recommend creating items of continuous Grave Strike and Golem Strike, should the DM allow them, to better deal with nonliving creatures.

Spoiler: Variant
A Good-aligned version of this build ought to be possible (obviously changing a lot of the fluff). In such a case, a feat could be replaced with Intuitive Attack, allowing Malcolm to focus solely on his mental ability scores (perhaps by increasing his age even further).

Do note that because of the difficulties inherit in being Exalted while also enjoying membership in the Zhentarim and Ebon Cabal, the feat is perhaps best not taken until Malcolm doesn't need to be friendly with either organization anymore.

Also, as Malcolm is already drawing a weapon every round and rendering foes flat-footed, why not enter Human Paragon for a level to make Iaijutsu Focus a permanent class skill? It'll cause him to lose his third iterative attack, but the damage gain from IF probably outweighs that.

Spoiler: Sources
All non-PHB sources are listed here.

Practiced Spellcaster

Skill tricks!


CoV Web Enhancement:
Zhentarim Soldier

Silverbrow Human

Imperious Command, Surprising Riposte

Able Learner, Chameleon

Absorb Weapon

Twisted Lord

Sneak Attack Fighter, Thug