Happened to me once. I wasn't sure how I felt about it at the time, but I was definitely leaning toward "offended". I was in my old neighborhood in mid-town Miami. It's the fringe of the art district, and the heart of the ghetto. The people keep goats and chickens in their yards. The railroad bisects the neighborhood, and both sides are the "wrong" side of the tracks. I went back there as I do once a month to wash my car. You see, they huave this carwash that uses cleansers that don't harm the water table, and all the water is recycled. There is a cafe on-site that serves organic fair-trade gourmet, but I can't usually afford to eat there. It takes half an hour to wash and wax my car, so I was headed to that familiar scourge: Starbucks.
My hair was worn in a long paige-boy that was fuschia on top, and back underneath. It was winter, so I had on my favorite hoodie. It's black, and has a glow-in-the-dark skeleton roughly in line with my own skull, torso, and arms, front and back. I think I had on pajama-bottoms with little grim reapers and tiny banners urging, "Don't fear the reaper!" I might have had on jeans though. I was cold, so my hood was up, but the strings were not drawn. I had a shirt underneath the sweatshirt, but it was low-cut, and my partially-open zipper stopped just above the neckline.
I saw a man walking in the opposite direction. He had on really interesting headphones, and as we neared each other, I kept eyeing them. When he got within hailing range, I smiled politely, and said something like, "Good morning." His immediate response? "You don't look like a real woman." I was confused, then angry, then (according to my journal, the feeling I settled on was) disturbed. Without thinking, I half asked, half exclaimed, "What!?" He replied, "Oh! Oh God! You are all woman!" I turned my back on him and began watching the heavy traffic so I could cross the street and caffeinate myself in peace and mediocrity. He kept trying to get me to go home with him since he assured himself I was in possesion of a vagina. I was disturbed that he couldn't just wish me a nice day like I had wished him. But I was never quite sure how I felt about not immediately being perceived as a female, even if I was dressed for errand day. I think I even had my period.
The entry in my journal says I found the encounter "more strange than offensive". But I know that's because he hounded me to go home with him (at noon on a random Tuesday, after three exchanged sentences) my until I showed him my ring and told him I was married. His response to that revelation was, "Wait. You were just being friendly? That's so unusual in Miami." I told him I was from New York, another city with the same reputation, but that I'd found both cities to be full of friendly people who say 'hello' just to be nice. My journal entry emphasizes this aspect of the incident, but when I think about that day without glancing at my notes, I really only remember that some dude thought I looked like a trans.
My journal questions my feelings about being mistaken for male-to-female. "Though I found the encounter more strange than offensive, I wondered if I should ever have felt offended, even briefly. I have long hoped to someday be reincarnated as a drag queen, and some days I am more handsome than pretty. *shrug*"
I also remember feeling twinges of pain and shame because my mother was frequently called 'Sir', and one time a cross-dressed man came up to us and told her that the work she'd had done was exquisite, but that she definitely needed electrolysis. Well, she had an endocrine issue that caused her to be hairy. When she could get a very close shave, she was quite pretty. If she had acne, razor burn, or ingrown hairs preventing a shave, she could grow in a full-on lumberjack beard in only a matter of days. She never seemed phased by these things, but they always bothered me. I was very uncomfortable.