Realistically, security will not know that they are a GRS dilator, they will think that they are just a run of the mill "personal device." Having them in your carry on will not out you in any way. They may only stop to examine what the object is because of their shape and density on the scanner. For anyone traveling home from surgery, I would definitely recommend keeping them in you carry on, you don't want your luggage lost. You really don't need a letter from a doctor explaining what they are, they are not a prohibited device, and pretty much any security screener will take one look at them when going through your back, turn red, and put them right back, embarrassed to have examined what they perceive to be just a "sex toy." They probably have no idea what a dilator is.
Funny story from my trip home. I was traveling back with my mom, who was carrying the heavier carry on, I only kept track of my purse. So she put the carry on through the scanner, after taking out our lap tops. After it went through, she was called aside with the bag because something caught their attention. I told my mom that I thought it was my "medical devices" as I called them in the airport. The screener ran the bag through one more time, then went through the bag located the "suspicious" item, which was the pouch containing my dilators. She lifted the flap on the pouch, saw the dilators, blushed, quickly put them back in the carry on, and sent my mom on her way. I think it was far more embarrassing for her than for my mom or even me had I been the one holding the bag.
Moral of the story, carry them on. If anything happens, it will likely result in the security screener being far more embarrassed that they did extra screening on what they come to think is a sex toy, and the fact that they may have handled the object. After you are sent on your way, they will probably vigorously wash their hands, and tell a story about the dildo they accidentally touched, and the size of the dildo will grow each time they tell the story.
Kat
