I am a retired widower and have been taking road trips of a week or ten days through the west. This trip took me to Arizona and today I was in Scottsdale looking at a property I own there.
I had checked the property and spent the night in a nice hotel and was having breakfast at a nearby coffee shop. I like to wear panties and bras and have gotten rather bold lately, wearing a bra with forms. I am a big guy and it isn't real obvious, though, if you look you can tell.
I was wearing a blue oxford shirt with a white bra, so I didn't think it was too obvious.
The restaurant was crowded, and I was shown a just vacated booth in the back. I had set up my Kindle to read while eating and was looking at the menu deciding what to order when the waitress, a pretty middle-aged woman, asked if I would share my booth with, indicating with a sweep of her hand as she said, "this nice gentleman."
Ted was a nice-looking man in his early 60's, dressed in khaki cotton trousers and pink cotton oxford, like my blue shirt. Not wanting to be churlish, and thinking I'd just as well talk with someone than eat alone, I said "of course." Ted was a local who had moved to Scottsdale from the San Francisco Bay Area recently. He, too, was a retired widower, enjoying his leisure time in that desert community. The small talk progressed easily throughout breakfast and we got to the dating and women aspect towards the end. He had dated a few ladies but nothing serious. There is an easy openness with strangers as we know we will never see them again and don't really care what they think of us. He talked about friends he had and then, looking at my shirt said how many of them liked to wear lady's underwear. Some cross-dress completely and asked if I did that too.
I was a bit taken aback, but secretly thrilled that he noticed and brought it up. I replied saying I just like wearing the bra and panties and had no desire to try to be a woman or dress completely. It was then that I looked closely and noticed the outline of a bra under his shirt. It must have been pink because there was no color contrast. He noticed me looking and said, "yes I am wearing a bra."