Hello, dear!
I asked the very same question here a long time ago, and the support I received here helped me a lot not only with accepting my feminine companion (it's not just a "side", I prefer "my best friend ever"), but also to resolve some very deep and serious issues in my life and in my family.
My first time out was one of the hardest things I ever imagined. I've been preparing for it so many times, and each of them was ending right at the front door. After almost an year of failing attempts I finally succeeded by literally forcing myself out with a single though in my head - "shut up and just do it". Then I got on the street looking as a scared little kitten. At least I felt this way. I started walking slowly through the square (I cursed myself for living in the town's center), making my way to the nearest dark street, and speeding up my pace. My feet were trembling and it took all of my power to keep walking normally in my heels (which I also cursed). Yeah, I got a bunch of looks at me, I got the creeps and I was screaming inside "let's go back home, I am terrified that something might happen". All I heard back in my head was "really? Let it happen. I'll deal with it.". I got to a darker alley and I then realized it. I was a damn hot chick, I felt like one, I got attention, because I looked awesome, which was actually the whole idea. Why on Earth would I get out dressed up as a girl? Why the makeup? Why the whole thing at all? I needed attention and I got it. I manned up, I walked around for twenty more minutes and on my way back I really didn't care, when I passed through the square again. Didn't even notice if there were any looks at all - my head was already filled with my regular to-do stuff. I got home and cooked a nice homemade sushi set. I felt wonderful after the whole experience!
As with anything else - either you do it or you don't. Saying that, I've been preparing for a walk around the neighborhood for the whole day, and after finishing some work at home I finally got out at 5:30 PM (it's EEST, I am from Bulgaria). Although I still have concerns about "what IF someone recognizes me" and I have a swift direct answer to that - "so what?", I always keep in mind I might need to defend myself, because there are still a lot of people around here being a bit hostile to those who are... different, and they openly say it. I must share that as a man in my occasional outfit (going to work, hang out, etc.) I feel nearly invincible and I show my total carelessness to everything around me, and that actually helps a lot. Yeah, I learned to act like them, because years ago I would not exist as a girl, literally. Anyway, regarding overall attention -one of my neighbors saw me the other day on the stairs - short black skirt, thick black pantyhose, over-knee black leather boots, satin black shirt, a bit messy haircut - just quickly looked all over me and immediately started buzzing his phone. That much of an interest. They certainly don't care. Or maybe it was the all-in-black look, I don't know. Nor I actually care, frankly.
After all - it's all inside our minds, but of course, like in some of my cases, seeing a gorgeous-looking girl (I love being one!) walking around with no obvious direction in the middle of the night definitely attracts attention. Yeah, I get a lot of "offers". I generally do prefer the "shadows" way, both as a man and a woman, and it is a just personal preference. But I have to admit - staying in the open regardless how you look makes you less interesting that lurking in the shadows, especially for the patrolling police cars. I had one driving slowly after me and once I got under the street lights they just got past me. Anyway, blending is not an easy task, but the important thing is to not overthink it.
Not long ago I did a comparison between Grace and "the regular" me, I shortened it down to the following conversation:
1. What do you do to blend in? -Nothing. Never thought about it.
2. How do you deal with people staring at you? -Do they?
3. Okay, what if anyone asks you something or simply speaks to you? -Well, reply back?
4. Fine, if they become aggressive?! -Usually I'd try to quickly talk my way out of it, then - run. If necessary - call the police, fight back. What world are you living in, anyway?!
5. Don't you have any concerns when you are on the street? Whatever these might be? -Yes, of course - the high possibility of an asteroid hitting Earth ending all life on it. And getting my wage, so I can live long enough to see it, while drinking a glass of Jack. What are yours?
Silence.
Eventually, this sealed my concerns for good. They were all unreal. It turned out my feminine companion was nothing more than a growing kid that needed guidance. So, a "first walk out as a girl" would be like a baby having its first steps, right? It takes time and effort, and each moment is really worth it.
A side note here, though - recently I started getting out at around 6AM or 7AM and to my surprise - no one even looked at me! That ringed a bell - who the hell cares what's going on at such an hour? I certainly don't. I am sleeping with my eyes open and I just get to work. Everyone was exactly like that, as was I an hour later, when I had to run to work, being late because I had a ton of makeup to remove...
Aaaand, I am still wondering why the female me is so eager to go out for walks, while the male me prefers staying at home, but that's another story. Saying that - I'm getting late for my evening walk!
Anyway, if you have at least one person to support you - you got it all. Talk to them, share, get them in a car, go somewhere no one knows you, have a good time. Good friends always help a lot, and that's exactly what friends are for.
Apologies for the wall of text!
Wish you a lot of fun, lovely!
Regards
Grace
Originally Posted by gracielle
Hello, dear!
), but it's hard to achieve, yeah... 
Anyway, there are fully legal and smart ways to quickly defend yourself, and women around here are actually being advised to do so, just in case.
