Stepping Out: After the First Time (Part 5: Some Sissy Mistakes)

After shoe shopping, I was on a high, and I was convinced that there was no stopping me now.  In my mind, I assumed that I would be free to go out dressed as a woman anytime I wanted, without being noticed. 

"I have this passing thing mastered," I said in my mind.

My week of being able to dress almost exclusively as a girl, and having my nails painted was coming to a close, and I wanted to go further before it ended.  My only decision was what to do next.  Unfortunately, I wasn't so lucky the next two times that I went out.


One night I saw a pair of pink wedges that I liked, and instead of shopping online, I decided to go buy them at the store.  My prior shoe shopping experience was so successful, I wanted to relive it.  It was late, and on impulse, I quickly put on some makeup and a dress that I liked and headed for the store.

I walked with confidence, telling myself, "Just act like a girl.  Attitude is everything."  But I would find out that's not entirely true.

Going to the shoe aisle, I found the pair of shoes that I liked, but the two girls in the aisle right next to me seemed to look at me.  Not wanting to be too close to them, I went to another aisle and tried on the shoes and decided to get them.  A female employee walking by gave me a bigger smile than one would normally get.

I wanted the shoes, so I decided to take the plunge and wait nervously in line with a lot of people in this big chain store.  Walking up to the registers, I didn't really making any eye contact with anyone and just casually waited.  Finally, it was my turn, and the cashier seemed to smile when looking at me, not in a malicious way, but seemed curious.  I knew she knew I was a man by the look that she gave me.  I wasn't embarrassed and I didn't really care, but it did seem to bring the thought to my mind, "You're in the middle of a store dressed as a woman!  What are you doing?"

I paid and walked out of the store with my pretty shoes.

Now that I think about it, I guess I wasn't totally passable that night, but luckily there weren't a lot of people around since it was almost closing time.


A few nights later, I returned to the same store.  This time, again, I was in a sleeveless dress, and now that I think about it, I think my shoulders were one thing that gave me away.  Another thing was that the dress I wore was too low cut for my chest.  Seeing a male chest without the continuation of the breast signals that something isn't right.  All you need to do is give away one little cue that you're not a woman, and people start scrutinizing the entire package, and then they see through the disguise.  I found that out the hard way that night.

I knew immediately this time that people knew.  It wasn't like the other successful nights when I moved freely amongst the people in the store.  No this was an entirely different feeling.  At first, I didn't know, and just did the same things I did on the previous nights, looking at dresses pretending to be just a regular girl.  I caught some weird looks, nothing much that registered at first, but when I went to the intimates aisle, a lady who was shopping looked at me kind of strangely and left.  I almost knew then but didn't want to jump to any paranoid conclusions.  Still, I decided to take my leave from the store.  I didn't really feel scared or embarrassed, but I didn't want people to know either.  If they did, then I thought, "So what?  I'm a stranger in a dress.  They don't know me, and if I give them a bit of a giggle, then so what?"

Walking toward the entrance, I saw a few more looks, and one girl said to her boyfriend, "Oh yeah...mustache..." I caught in passing.  I’m pretty sure that she was talking about me, and realized that my makeup probably wasn't good either that night, and the irritation of shaving against the skin for five days had probably caught up with me too.

It was not a successful night as far as passing, but it did teach me a lesson that I wasn't so scared to be a man in a dress in front of strangers.

I'm not lying.  I really didn't care.  If the whole store came to a screeching halt, and people asked me if I was a crossdresser, I would have told them with confidence that in fact, I was.

Strangers don't seem to scare me, it's people that I know.

That pretty much ended my week of dressing and going out.  There were a few more places that I went, which I didn't describe, and I had such grand plans for a few more nights, but when the last days came around, I just decided to give myself a rest, assured that I had done quite a lot for a first week of going out dressed.  It was a fun time, and I'm glad that I decided to live life instead of playing it safe.