My most interesting airport security experiences actually took place before enhanced screening, probably because in those days no one really cared about things that could cause you serious delays today, like setting off the metal detector, or having very odd things in your bag.
The best one was flying out of Los Angeles on the way to a gay leather fetish event. I was wearing tight Levis, scruffy biker jacket, and knee-high motorcycle boots. My boyfriend went first, and of course set off the metal detector (PA? Cockring? whatever...) A rather large female security agent was scanning him with the wand. She was about done, and I was waiting to catch her eye before I stepped through the metal detector portal myself. Just a she looks up, this flaming queen of a supervisor comes prancing over from several lanes away, practically tackles her out of the way, screaming "I'll do him! I'll do him!" So I step through the metal detector, and set it off. He asks me to step up on the little box, or platform, for the manual search. However, he doesn't use the wand. He immediately goes to the patdown, except it's more like groping me all over, in particular the boots and groin region. After a while, he begins asking obviously security related questions, such as "Sir, what size boots do you wear, Sir?" When I answered "Usually about a 15," (yes, I have big feet, too) a whole new series of grovelling and groping started. There were two similarly attired guys behind me (part of my party) who got a similar, but somewhat less thourough, treatment. When he was done, and let us move on, he just walked away, ignoring the next person behind us, who went right through the checkpoint without even being screened.
Once I was flying through Chicago O'hare, and the screener had a lot of trouble with things in my carry-on. His procedure was to locate and remove one offending object at a time, and then xray the bag again. After a number of innocent objects had been removed, he came and said there was just one more problem. He asked "Do you have some bracelets in your bag?" I had purchased a pair of metal cock rings in Chicago. And seeing as my cock is the same thickness as my wrist, I decided it would make things much simpler to just agree that they were bracelets, and be on my way.
And then there was that time at customs in Toronto, where the contents of my friend's suitcase so disturbed the inspector, that she decided she would just let all the rest of us go without looking...