If he asked where your husband was, then either you pass excellently, or that guy at the counter was a true encourager!!
Flying Pretty:
* Option 1: You can go through security, and then change in the secure area.
* Option 2: You can go through security while pretty. The US TSA is used to this stuff, or so I hear. I never present female. I have flown while dressed pretty as a guy several times. No problems.
Things to consider:
* You will possibly have to stand in a corral while waiting to go through security. You could be in the presence of ~50 people for 30 minutes in this situation.
* In security, you may have to be scanned by the machine and someone will be able to see under your clothing.
* If they detect something curious, they may hand-search you. They will ask whether you want to be frisked by a male or female TSA employee. You might want to pre-decide what your answer will be.
* This is a place where you may have issues with underwire bras or breast forms. I don't know a lot about such things. See others' comments.
* Once you take off and put on slip-on ladies' shoes in security, you will not want to return to men's shoes!
* In the airport concourse, you may occasionally encounter a plane-load of people who just disembarked. They will be walking in the opposite direction of you and will possibly get a good look at you.
* Airport restrooms can be crowded. They probably will have alternative bathrooms for families, people with handicaps, etc.
* You may need to sit in the gate area for a while next to strangers.
When I have flown pretty, everyone treated me with respect.
The TSA web site has a page for people like us:
https://www.tsa.gov/travel/tsa-cares/gender-diversity
Joey