"The Black Octopus" (CR 20 encounter)
What danger lurks beneath the dark waters of night? The Black Octopus is a shapechanging orcish pirate who plies on the shipping trade channels. When he sights the PC's ship coming towards him, he readies himself and attacks, taking on the form of a black giant octopus from ages pages.
Note: The Black Octopus is a shapechanging grappler that I tried to build with a minimum of spellcasting. His offense works out decently well (he deals roughly 2,000 grappling damage per round), but his power level flies up in the next couple levels past 20, if you want to advance him for higher level groups.
Best of all, he does all this without any magic items. (If you want to present a better challenge for your PCs, you can give him tomes, ioun stones, etc.) Standard 32 point build rules. Stats below include himself fully buffed. All buffs are > minutes per level, so he activates them all before attacking a ship. The only questionable buff is metaphysical claw (which states it can be cast on any natural weapon as long as you have a claw or bite, so can it be cast on a tentacle?) but ultimately, all the buffs are more or less irrelevant to the build. Expansion is probably the most critical. You can push levels around to accomplish different feats (a couple more levels in barbarian or BBC gives greater rage for another +2 strength, druid or primeval levels can give more primeval forms per day, etc.), but the basic offensive power doesn't change very much. This character is an NPC designed as a boss encounter, so he doesn't need to go supreme more than once per day.
As a PC, he is still pretty good, but I'd tweak him a bit so he could be useful in more combats per day.
Frostblood Orc
StatsStr: 52 (17 base + 1 regression + 4 stat bumps + 4 racial + 12 Octopus Form + 4 Animal Affinity + 2 Chain of Offense + 6 Rage + 2 Expansion)
Dex: 18 (13 base + 6 Octopus Form + 1 Regression - 2 Expansion)
Con: 28 (14 base + 4 Octopus Form + 1 Regression + 1 stat bump + 6 rage + 2 chain of Offense)
Int: 5 (8 base - 2 racial - 1 regression)
Wis: 14 (15 base - 2 racial + 1 regression)
Cha: 5 (8 base - 2 racial - 1 regression)
HP: 335 (full at 1st, 2/3rds after)
BAB: +17 (all natural)
AC: 24 (+6 dragonhide husk, +9 natural armor, -2 size, +4 dex, +2 insight, -2 punishing stance, -4 reckless rage)
PP: 18 PP per day (4PP expansion, 4PP +3 Offensive Prescience, 3PP Animal Affinity, 6PP Metaphysical Claw on 2 claws, bite and 3 tentacles)
Grapple Check: +47 (+17 (BAB) +21 (Str) +8 (Size)) (*Edit, removed grip of iron)
Damage per grapple: 1d8+24 (base) + 2d8+9 (constrict) + 8x(1d8+24)+3 tentacles + 3d6+14 (bite) + 2x(3d6+14) (claws) + 6d6+28 (rend) + 14d6 (punishing stance) + 14d6 (Rapid Assault) = 449 (+49 first round only) = 449/498 damage per grapple check
Full attack (grapples) at: +47/+42/+37/+32 at 449/498 damage per successful check. Average damage: 1796/1992 (first round)
or
Full attack: +37/+32/+27/+22 1d8+25 unarmed strike + +32/+32/+32 1d8+14 tentacles + +31/+31/+31/+31/+31 1d8+13 tentacles + +32 3d6+14 bite + +32/+32 3d6+14 claws + 6d6+28 rend = 383.5 average damage. Plus improved grab on tentacle attacks. Plus the first unarmed strike is a DC 22 stunning fist.
Saves:
Special Qualities:
Cold Subtype
DR 3/silver
DR 1/-
Low Light Vision
Darkvision
Swim Speed
Scent
Stranglehold (Coup de Grace as move action)
Savage Grapple (not the feat, the Black Blood Cultist ability: on a successful grapple check, deals damage with all natural weapons)
Levels:
1) Warblade (Stance: Punishing Stance +1d6 damage -2 AC, Counter: Moment of Perfect Mind, other useless 1st level maneuvers)
2) Ex-Monk (bonus IUS feat and increases grapple damage)
3) Barbarian (+6 str with Reckless Rage 3/day, (BBC levels stack with barbarian levels))
4) Ranger (bonus track feat)
5) Fighter (+6 AC from Dragonscale Husk alternate class ability, bonus WF: Grapple)
6-13) Black Blood Cultist 8 (gain claw, bite, rend natural attacks)
14-17) War Mind 4 (+2 Str and Con, +2 AC, Expansion, Precognition, Animal Affinity, Expanded Knowledge: Grip of Iron)
18-20) Primeval 3 (+1 Str Con Dex Wis, -1 Int Cha, alternate form)
Feats (*are bonus feats):
1) Reckless Rage
1*) Endurance (bonus Frostblood Orc feat)
2*) Track
3*) IUS, Stunning Fist
3) Self-sufficient (primeval prereq, burned feat)
4*) Rapid Assault (+1d6 per attack on 1st round of combat)
5*) WF: Grapple
6) Wild Talent
8*) Improved Grapple
9) Improved Natural Weapon (claw)
12) Improved Natural Weapon (bite)
15) Improved Natural Weapon (tentacle)
18) Expanded Knowledge: Metaphysical Claw (or Grip of Iron)
Skills:
(Oh, who cares. He can probably swim.)