I was out last night with a friend and of course it was an enjoyable time and nothing happened. If I was in guy mode, the result would have been exactly the same. But I had some observations I thought I'd pass on to the fearful and newbies (even you lurkers).
1) Leaving the house, apartment, condo, whatever. Here's the secret. Ready....? Open the door and walk out. Yep, that's it. I realized I didn't even think when I opened my door last night. Maybe that's the real secret. Don't think. When I stay in San Jose, I have no garage. My parking spot is a short walk from my front door. I left in broad daylight, people were about, I passed several walking to my car. No reactions.
2) Driving. I was meeting a friend and drove about 30 miles. I was on residential streets, highways and stop and go traffic. No one is looking at anyone. I noticed that beyond my peripheral vision, I was too busy driving to look at anyone really. Even in the stop an go traffic, I barely noticed more than shoulders and heads. I think I was virtually invisible.
3) Parking. Parked ont he street and in a garage. Broad daylight still. Hundreds of people on the streets. I made the typical, minimal eye contact one makes with strangers on the street and I noticed nothing unusual.
4) In the bar. Walking in to the first stop of the night, a bar that seats perhaps 100 people, it was 70% full. My friend and I walk in and unlike the saloon scenes in old westerns where everything comes to a stop, nothing happened. Did anyone notice us? YES! I do not pass as a woman beyond a fast glance but people's eyes naturally rise to see a new person entering and just as naturally, the eyes moved back to their friends. The reactions would have been the same if I was in guy mode. We sat at the bar, got a drink and shortly thereafter a group a three men sat next to us. There were other seats available. We were just people who happen to be cross dressers, not just cross dressers.
5) In the restaurant. Our second stop was for dinner. Again, we walked past groups of people on the street, in daylight, entered the restaurant and nothing happened. We were welcomed by the hostess, and sat. We ordered, chatted and a received our meals. Just like normal people. Shortly thereafter men and women sat to the left and right of us. These same people engaged us in conversation asking about what we ordered, sharing what they like and the guy to my left recommend a dessert he particularly liked. He and I chatted about his new job, living in the city, just basic chit-chat. And HE started the ball rolling with the conversation. I was just a person. He recognized I was presenting as a woman and appropriately used all the proper pronouns and terms to reflect that he was speaking to a female. The place was packed and I never felt stared at.
So, if there is one piece of advice I can offer to help you get out, it's this: stop thinking. You are your own worst enemy.
Or, put another way, be in guy mode in your head. The normals are not out to get you. Now, I'll add that you should not give anyone a reason to fear you. Dress like a drag queen and you will not get the same friendly banter. Over the top never flies in the real world. Dress appropriately for the venue and you will be welcomed by the other patrons.
This is how I went out. I paired it with a red sweater to cover my arms and farmer tan. The pop of color looked good.