Hey there, I have some info that should set your minds to rest! Bear with me as I will get to the point, I promise!
I have a friend who was expecting her in-transition boyfriend to fly and visit her. As he has already legally changed his name, but not
had any surgeries, they were concerned about trouble with the TSA because of the discrepancy between male name and female anatomy. Plus, he was either going to be wearing a packer, or carrying it in his carry-on with other toys. So, my friend researched all about our rights and found out some interesting facts most don't know about when dealing with the TSA.
Did you know that everyone
has the right to request that searches of their bags AND their person be done in private? That may simply mean behind a screen, but still where other passengers cannot see you or your stuff. Even better, you also are allowed to have a witness with you which is really good in case you are taken into an actual separate room. You can also request a supervisor at any time if you are not happy with your treatment.
So, as you are smart to be wary about stolen expensive toys or tampering with them if in packed luggage, you should definitely carry them on. Now you should never have to fear embarrassment from them whipping out your sensitive items, no matter what they might be. We all know the stories, or may have even witnessed TSAs intentionally shaming people by exposing items in their carry-ons (I have seen this and I was outraged for the guy, but he just shrugged it off, so I didn't pursue it as it was not my place). You do NOT have to explain or justify why you are requesting to have a private search, pat down or requesting a supervisor! You can almost certainly count on them challenging you if they think they can get away with it, but knowing your rights should help you not get bullied by them. That's not to say they may not take their sweet time getting a supervisor there, or some other type of retaliation. But, you should note the times, even write them down and also write down any other details if you are being given trouble. Get their names, times, etc., though I have always found when I am prepared to deal with trouble, I never seem to get any, lol! It's always when you are off-guard and ill prepared, damn it!
As for tips, let me recommend that anything you expect them to question, such as a lump of wires and electronics or sex toys, be in their own see thru cases, or baggies. You can then have the toy ones inside something else, but having them in a clear bag often will protect them from having to be touched by them directly as they can see everything clearly. Sometimes they insist on operating something such as a camera to be sure it's not a decoy with drugs, explosives, or God knows what in it. They should not take it that far with sex toys and if they want to, it's best to request a supervisor as they are likely messing with you. There is no reason they couldn't see what they needed in the X-ray machine. They especially love to embarrass ladies alone who have toys.
And that brings me to a story of a gay male couple who came home from a vacation and went to retrieve their luggage and saw their bag on the conveyor belt with their huge dildo taped to the outside of it and everyone looking at it and gossiping. They waited and did not grab it until people were gone, but they were furious that it had been searched and the toy they had packed inside the middle of the bag was somehow magically moved to the outside with a bullshit note that the dildo had fallen out! There is also a story of a message being left inside a woman's luggage commenting on her taste in lingerie and other creepy stuff (especially creepy considering you are told to include your name and address on and in your bag in case it's lost!). My point is that yes, you should hesitate to pack your valuables and certainly your more interesting and/or expensive sex toys in your checked luggage. But now you don't have to worry about exposure to everyone if you carry them on.
You can always pay to ship them to yourself at your destination for a day after you arrive, if you like. Hotels accept packages for you, no problem. And while I haven't needed to travel with toys as of yet, I have shipped home purchases made on a trip instead of carrying them with me and it's SO much easier. I would definitely consider mailing toys to myself either diretion if for some reason I didn't want to carry them with me, so that's another option.