I only ever had 1 issue with the TSA and to be honest it was my own fault. At the time I was flying out to California for a week, on business no less. I was already post-op by the time so I was't too worried about flying but I didn't want to pack my dilators since I was still on a regular dilator schedule, so I took them as carry on. I mean they are a pretty expensive hunk of plastic and if they got lost, then who knows how long it would take/cost to get a replacement set from Montreal. Needless to say once I dropped my purse on the xray machine I suddenly remembered that I was asking for it. And ask for it I did. They were wrapped in plastic bags to keep sterile and suddenly they took me aside and asked me to remove them. Then they asked what they are for and said "they are used for people who have a sex change operation". The look on this guys face was priceless, a true kodak moment. He stepped back 5 feet away from me (maybe so he wouldn't get the TG cooties or something or maybe just to take me all in because he didn't believe me) and then thought for a moment and let me go. I mean the dilator is a solid piece of clear plastic with nothing to hide. He let me go and I flew to CA with no problems.
On the way back from LAX to New York is when I was hassled. This big black male guy doing the xrays says right out loud (and I mean loud)..."Uh oh looks like we have ourselves a professional lady here". So same routine as New York, but the TSA agents in LA were excited because they thought I was a hooker and were excited for some reason to do the search. There was thankfully 1 agent who seemed like a real honest to god professional standing about 15 feet away, because these pervs were just playing with my dilators and it was pissing me off. This one guy comes by, shoo the others off and asks me the same question, and I gave the same answer and he was way more professional and asked why I didn't check it in, I said it was because they are very expensive medical devices. He let me go. I swear because of that, there was an air marshall on the plane making sure I didn't pop out a dilator mid flight.
That's been my only post 9/11 flying experience that sucked. 10 TSA agents, one professional and 9 I wouldn't let them guard the garbage cans in a junk yard. So if you travel, pack the dilators in the suit case or better yet take it from me, get a second set