I've been with someone who used one on the first date. It was a little different because his member was kinda cold, but it wasn't a bad experience.

Make sure it's clean since it will make contact with her skin.

Cock rings can be life savers!!!! If you're really up for fun try the Vibrating Johnny toy.  I like to improvise from time to time with different items. I've used wide sized rubber bands and I like to use my thigh highs to do a nice a tie around my date's balls and cock. Stockings are great because the size is easily adjusted AND they're nice and soft against skin. I've even used clothes pins once --- per client request on this one of course!

They are a pain in the ass when he as to KEEP messing with it, but it's so uncommon I doubt I would have a problem with it.

Hey, as a long time provider in the game. I'm not put off by anything that will help you enjoy your experience even better. If this is something that you depend on (physically), then don't forget it when the opportunity arises. But if this is a mental issue, then figure out what's different in your life that has taken the ability to get and stay hard a problem now. Stress is the number one key factor, other then medications, and poor lifestyle choices not taking care of your health.