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The silicone ring should fit comfortably behind the glans without causing excess engorgement and purple coloring. When your Innerwear is brand new and you wear the sleeves and Retainer Band before they have been broken in for a more comfortable fit, you may experience excessive engorgement. In which case, give it some time and alternate the sleeves until they fit more loosely before layering on top of the Innerwear.
For length, it sounds as though you could use a size longer, however, it’s hard to say for sure without seeing a pic. If you are not comfortable posting here you can contact us at the support email for determining if a size adjustment would be the best option.
The folds of the baseband will provide the fabric as needed for the extra length when wearing the Corkscrew.