I went out with one of my friends who knows my dirty little secret. My SO, this friend, and this friend's sister are the only ones who know. Anyway, myself, the friend and the sister went out to a mall that we frequent. I haven't been there myself in forever, nothing there to do anymore when your a college student. It was fun in high-school, but not really anymore. Though, I digress.
I was absolutely nervous when i went out the first time. Your mind is always assaulted by "what if's". I was so scared I was going to run into one of my friends who doesn't know my dirty little secret yet. I was so afraid of that, and I actually saw one of my room-mates there. Apparently I was "blended in" that him and his group of our mutual friends (and the other two room-mates) didn't even notice me when my friends and I walked by.
I kinda put my head down and walked by. When I got home I was in the male version, (like a superhero.) The room-mate described, according to him, a beautiful, gorgeous brunette in my exact outfit. Said she was outstandingly gorgeous.
That totally made my day, if my friends don't even notice me then I'm totally good.
On top of that, I frequent Hot Topic, and the lady there, known as Skittles (nickname xD), saw me and thought she recognized me. I walked up to the counter and the ensuing conversation went something like this.
"Oh my god, you are totally adorable, I love your boots. Where did you get them?"
In my girl-est falsetto voice, "I got them here actually" and raised my skirt so she can get a better look. I was in an ankle length skirt, with ankle length boots. Showed her the boots by raising my leg and letting her see.
When she got a better look and went back around the counter, She asked me. "Haven't I seen you in here before? You totally look like someone I know."
"No, just moved here actually, first time here."
"Well, welcome to the neighborhood, what's your name?"
"Jasmine, or most people just call me Jamie."
"Well if you ever need a hand or wanna hang out, let me know, people call me Skittles, but my name's Jessica."
"That's really sweet, I may take you up on that." She scribbled her number on the back of my receipt. I completely and totally believe she was flirting with me. O.O So, CD.com, should i take her up on it?
For a first time out, it was a total blast and success; it was so worth it. Be confident and be yourself, even if that is a guy in 3 inch heels.
By-the-way, the girl's name is skittles because she dyes her hair a different color every week. I know her as a man, not very well, but I think I may get to know her well as Jamie.
Edited: I forgot to mention that when the room-mates passed us, they said hi to the girl i was with. That was it though, they know her but not so closely that they would initiate a conversation. So they gotta pretty good look at me, but not one long enough to notice who i was.
Originally Posted by tammygirl79
I totally would not have been able to do it if not for the inspiration from everyone's stories and everyone telling me to go do it. 
