Monks of the Way of the Contortionist have strived to emulate the serpentine motions of the flexing, coiling boa, possessing even amongst the most physically-adept martialists a sense of control over their physical structure that few can hope to rival. They are able to move in ways that belie their flesh and bone, seemingly able to flatten themselves through the bars of imprisonment, to whip and sway in a snakelike manner that befounds attackers and feints defenders. Most of all, though, they are known for their nigh-unbreakable holds and grabs, a curving, locking embrace that can stifle motion, pressure nerves, lock joints and, with the proper training and application of their more malleable bodies, break bones with but a graceful tightening of their muscles.

Boa Style

When you choose this Monastic Tradition at 3rd level, you begin to fine-tune your ability to move your muscles, your extremities, your very bones, until your body structure becomes flexible and capable of contorting to your will.

As a bonus action, you can make a special grapple check, using either Athletics or Acrobatics to initiate. The creature must be one size larger than you or smaller. If successful, you enter Boa Style, wrapping yourself around the creature. While grappled in such a way, the creature cannot take the Attack action against you, and you employ a different set of Ki Powers.

Constricting Bar

Immediately after you deal unarmed damage, you can spend a ki point attempt to further restrict the prey's range of motions. If they fail a Constitution saving throw, they are considered restrained until the end of your next turn, and grapple checks they make will be at disadvantage.

Muscle Control

You can spend 1 ki point to force your prey to make an Attack action against a target within their reach as a bonus action.

Tightened Coils

You can spend 1 ki point as a reaction to curl your form closer to your prey, using the creature you've grappled as cover. Until the start of your next turn, you are considered in half cover.

Contortionism: Acrobatics

You gain proficiency in Athletics or Acrobatics. If the monk is grappled, they may spend half their movement to break free.

Contortionism: Athletics

You gain proficiency in Athletics or Acrobatics. If the monk is grappled, they may spend half their movement to break free.

Malleable Form

At 6th level, you find greater control of your physical structure, and bend the limits and your form with them. You are able to fit into and move through spaces considered one size smaller than you without losing movement, and squeeze through even tighter spaces at half movement, such as cages, prison bars, or particularly tight crevasses.

Malleable Form: Acrobatics

Moving stealthily, through space that other creatures occupy, and other tight spaces do not interfere with your movement. In addition, gain expertise in the skill chosen for your Contortionism.

Malleable Form: Athletics

Moving stealthily, through space that other creatures occupy, and other tight spaces do not interfere with your movement. In addition, gain expertise in the skill chosen for your Contortionism.

Anaconda Style

At 11th level, you've gained greater mastery over your unique grappling style, and become more capable of controlling your prey once they've fallen into your grasp. Your Boa Style ki powers are improved in the following manner.

Nerve Brace: The hold on the creature finds a sensitive place to add pressure to, locking the prey entirely. At the start of the monk's next turn following a successful Constricting Bar, they may spend another Ki point to put the prey into a Nerve Brace. On a failed Wisdom save, the creature becomes paralyzed until the end of the monk's next turn.

Unnerving Puppetry: The twisting limbs and bending joints of the monk are better able to lead their prey where they're most wanted. When activating Muscle Control, the Monk may spend an additional ki point. On a failed Strength save, the constrictor may move the creature half of the Monk's movement and allow Multiattack or Special Actions, if the creature is capable of such. If the creature is capable of spellcasting, however, the Monk may not force their prey to cast a spell.

Serpent's Den: An expert contortionist is never truly caught out, even when they have prey locked in their grasp. When taking the Tightening Coils reaction, if you spend an additional ki point, your prey becomes full cover, and takes the attack in your stead.

Jormungandr Style

At 17th level, you've mastered the art of contortionism to such a frightening extent, that to your prey, you seem to be capable of stretching your form unnaturally to contain even the largest of creatures. You are now capable of grappling creatures of any size, are immune to being grappled, and at the start of every turn you begin with a creature grappled, that creature takes 1d12 force damage from the sheer inescapable malice of your grip.