I appreciate your determination.
The penis is the most dynamic appendage on the human body so there can be a learning curve involved to master the process of putting the Innerwear on to wear, and the sizing, as well as the model of Innerwear, may need adjustments. However, we will have no issue sorting thru all this with your positive attitude.
You can try an alternative method to put the Innerwear on. First, put the thin spandex sleeve over the glans and halfway down the shaft. Use the excess length of spandex sleeve hanging off the penis to thread the Innerwear sheath on and then slide it into place at the base of the penis. Remove the spandex sleeve by sliding it out and tuck the excess skin back inside the sheath.
I am not sure what size you are wearing but each size down in girth, for example, 28,26,24 is 1/4″ tighter in circumference. For length, each size up or down from A-C is 1cm longer or shorter and for D-J is 1.5cm longer or shorter.
You can also do the pinch test to get the right fit and note the excess amount of silicone that you need to be removed. The following pic indicates that it is two sizes too large.
If you prefer, we have the Strapless version of Stealth without the ball band.
If you have a tapered shaft that is thicker at the base and midshaft we can make you a custom tapered sheath.
We can make a Strapless Sleeve with or without a custom taper or a simple resize for $15 which includes the cost of shipping.
Let me know what you would like to do.