First Time Sissy (Fantasy)

I had been dressing in secret inside my house for several years when I was a teen.  One summer I got an urge to go out of the house in one of my sister's sexier outfits.  I thought I could go for a quick walk down the street unnoticed, but little did I know that the clothes I was wearing was sending a signal to the men all around.  I thought I was a regular guy who liked girls, and just liked dressing on occasions, but my neighbor showed me another side of myself that I didn't even know existed.  When my dick got hard at having him handle me like a woman, some part of me knew that I would be a sissy for the rest of my life.  I couldn't wait for him to see me in my blue dress the next day.

Stepping Out: Fantasy and Reality

The week described in my other "Stepping Out" posts was my big adventure out.  I had so much more planned for that week: going to get some fast food while dressed, going to a movie, going to the mall to get some Dermablend, but time went by and I never did those things.  My wife came home from her trip, and I went back to being a part time man again, and regrew my facial hair at her request.

Recently, though, I had some days off, and decided to take some adventures out.  One fantasy I've always had is to wear a somewhat detectable bra beneath my shirt and go shopping.  On a whim, I decided a few days ago, to finally go ahead with my plan.  I needed to go to the drugstore, so it presented the perfect opportunity to wear a bra to a place that I'm not recognized, and don't go to too often.

My dilemma is almost as if I want people to know I'm a sissy, but when confronted with it, I get scared because I don't really want them to know.

The line between fantasy and reality somewhat changes when I get out into immediacy of an everyday situation.  In my fantasy, it's so clean and nice.  There's the fantasy element and nothing else.  There are no noisy cars going by on the street and no harried office girl waiting in line behind me at the register looking at me strangely.  There's not that working guy, looking at me like I'm crazy.  As soon as I enter a store, and come face-to-face with my fellow citizens, it's a completely different feeling, almost one of regret.

Still, I wanted to do it, and I put on a solid green tee with a white training bra beneath it.  I love the feel of a bra bracing my chest.  It makes me feel so much more girly than panties, and the fact that people can almost see is both thrilling and scary.  I wanted them to see, but then I didn't.

I think in the past, I was scared that people would really know my secret.  It's an uncomfortable feeling, knowing that I'm trespassing on people's expectations for "normal" behavior.  Still, I know another part of me wants to be recognized as a sissy, and not just in fantasy.  To subtly let them know that I enjoy wearing a bra, and am proud of it, is a deep thrill.

I entered the store and went around, and then got caught in the line at the register.  A girl stood behind me.  I wondered what she was thinking, knowing that I had two distinct bumps from my adjustable straps showing through.  Did she know?  The thought made me nervous.  Was I becoming more of a sissy?  It was uncomfortable, but I liked it too.  It's strange how fantasy and reality collide.

I was anxious to leave the store.  It wasn't quite the thrill I expected, but it was exciting in a different way, since I had the nerve to actually do what I imagined in my fantasy.