The wearing of the Sheath is a personal option, which comes with time. It can be forward towards
your penis, back toward the string or inserted anally. So, yes, anal
penetration is possible while wearing any Vee-String with a Sheath. You can change positions of the Vee-String many times while you’re wearing it. It will need experimentation, and this is a big part of the fun.
♥♥♥ Ladyone