Conventional silicones for glazing and roofing repairs don't adhere to PVC cable jackets
For this, I would spread a layer of the silicone to extend it over a short section of the PVC cable jacket. Then wrap one layer of twine, tightly, over this section, squeezing out the silicone to the top of the twine. Then spread the silicone over the twine to ensure it is waterproof. This composite fiber construction will keep the silicone from separating from the flexible PVC.
Silicone will maintain a watertight seal, as long as it is not allowed to "tear away" from the other material. It doesn't "stick" to plexiglass, for instance. But I have a leakproof plexiglass tank sealed with silicone, using nylon bolts to maintain positive pressure.
I do the twine trick mostly with hot glue, to be clear. I don't use a lot of silicone. But it works great with hot glue, where I have used it for exactly this kind of application. I think of it Giligan's Island carbon fiber. Even with solvents and a knife, it is VERY difficult to remove. Due to the cumulative compression of the cord wrap and the perfect molecular fit of the hot glue to the sheath, and the excellent adhesion of the glue to the twine, there is practically no way to silp the pvc out of the hot glue sheath with brute force, even with alcohol added. It's one piece. The PVC cable sheath is basically not allowed to stretch/flex anymore than the twine/glue allow it to. To remove, each strand of string has to be cut and alcohol applied. I would guess it would work the same with silicone but can't be 100% sure.