I had a similar experience with the earlocks; to get them to seat securely, I had to get a deeper insertion depth than would have been comfortable with the stock tips, because otherwise the earlock would not be at the correct angle relative to the anatomy of my ear. (Lol)
You may want to try JVC Spiral Dot tips. These are very short, so they don't extend much beyond the end of the nozzle. Audeze's groovy eartips are also shorter than the original tips, but because they're quite rigid, I found they got uncomfortable when i was wearing them for a long time.
Another good option is Spinfits, which are very flexible. They have a wide-bore version of the original Spinfit coming out, which will probably be quite good.
Currently I'm using one of their dual-flange versions, the CP-230M. However, I'm not currently using the earlocks, b/c I found the earlocks unreliable. My first pair broke b/c of a manufacturing defect; the second pair appeared to be sturdier but would not stay securely attached to the iSines. The new larger matte finish earhooks are fortunately comfortable enough for me that I don't miss the earlocks.
Another option for the earhooks is to cover them in some silicone or neoprene tubing as some folks here have done. This will increase the surface area and reduce pinching/hot spots.