Hi Ola,
I have just put my P27/136 keel back after the winter and have had a look at it.
The keel is rectangular at the top and has four nylon guides bolted to it. This is the part which stops it falling out. The keel box on the boat is rectanuglar all the way down to the bottom, where the hole through the hull is foil shaped to match the keel shape. this is where the stopping is done.
There are two nylon bushes fitted underneath into the hull at the front and back of the hull slot to help absorb any shock loads from grounding.
From your pictures it looks like a previous grounding had damaged the back of the keel - and maybe the hull back nylon bush has been damaged or displaced then fallen out? - thus preventing the keel going down until you pulled the keel out ?
Is it possible to lift the keen out on the boat again then you can have a close look at the keel box from the top and underneath?
For what it is worth I do not use any lubrication on the keel or box as previous experience is that grease just goes sticky and makes things worse - especially as we get mud in the bottom of the slot as we dry out each tide.
Another mod to consider is fitting a second wheel in the top of the keel and a additional deck mounted block on the keel box with the dead end of the keel rope fixed in the keel box. This provides additional purchase and makes lifting the keel much easier.
Cheers
Chris