I ended up purchasing the Sabre Skin. I have had no issue getting it on, although my foreskin continues to be a problem. While it would still be interesting to hear other strategies here, I will share what seems to be working (so far) for me. Simply having the Sabre skin sit just in front of the corona, rather than behind it has worked well. While my entire head isn’t exposed which is a bummer, the sabre skin grips the glands quite well and keeps things from moving forward. This works well on its own and even better over the inner wear. With the inner wear, I keep the silicone ring behind the corona and the sabre skin just past the corona. All stays put and its pretty comfortable. Urination stings a little but nothing like it did with the retention band.