there are various factors involved with how deep one can go. You may have to just train more. Maybe try some thinner toy, to push your depth limit. You might unfortunately have a physical limit. I have read that from other users, hopefully you don't have that issue. It is one that you will have to find out for yourself though.
I have all three toys you have mentioned. I can hilt both XL Chances. I just got Henry this week, so far i can make my way down to about a inch past the medial ring. Jackson i have a bit on trouble with, I can only take about 12" of it. My theory is that its head is a bit too big and rough for me to train consistently with.
A toy the I highly recommend for anyone trying to push their limits is Slink from SquarePeg
https://www.squarepegtoys.com/shop/slink/ I have a 2X and it is one of the best toys i own. It goes deep very easily and the plug feels amazing. Its just a fantastic toy.
EE also has double-ended Remus, which i also have and can take about 19" of. I went with 50/50 soft/medium firmness, which sounded like a good idea and the medium sides firmness helps provide some stability during insertion. But, I feel that the medium firmness side is hampering my ability to go any deeper than i currently can. So long story short, get in in soft, if you do go for one. this toys helped me out a lot with getting all my equine toys deep.
Hope this helps. feel free to ask more question.
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