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So, in PFS i have a grippli that likes to grapple. his schtick is- he isn't a tetori monk.
Recently there was the question of size relativity vs grappling- could a medium creature grapple a huge or larger creature; or could a large creature grapple a tiny creature. It makes sense for the former to be difficult, but grapple rules are really vague.
So to avoid any rules lawyering, i'm looking for ways for creatures to grapple other creatures they normally couldn't, due to size.

Evilserran |

Ever see a grown man being pinched by a blue carb? spider crab? walk into a wolfspider's nest? Ever been bit and held onto by a parakeet? It may not be the same as having braun strowman on top of you, but it makes you ever bit as unable to battle for a little bit. There is also the form of grappling that involved simple join manipulation, if hes the size of you leg, then he can still torque your foot or knee, he can still get up behind you and full nelson your butt.

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I was asked this by a GM.
I said that's easy. I grab the right wing and wrap it around the right side of the body and horizontally through the dragons mouth pinning the dragons right arm up against it's a head. I step on its left foot, and hold its tail with my right arm using my small size to force it into a tremendously painful back bend.

BlarkNipnar |

A) IMO, if you can pass the check -> seems fine. Look below, however, as typically a player says "I want to do X" and then the GM says "Roll a blah check." Saying "I want to grapple the dragon" has issues.
B) GrandLounge points out that there are jujitzu (sp) ways of doing things. Consider watching some MMA or Jujitzu instructional vids to come up with neat "animations" for what you're doing. Everyone will benefit from this; while leaning on just A will result in breaking everyone's immersion.

blahpers |

I was asked this by a GM.
I said that's easy. I grab the right wing and wrap it around the right side of the body and horizontally through the dragons mouth pinning the dragons right arm up against it's a head. I step on its left foot, and hold its tail with my right arm using my small size to force it into a tremendously painful back bend.
That's an impressive amount of leaping about for under six seconds. You still get a move action, too!