Saturday, August 18, 2012

Stepping Out: Some Thoughts for the Future

It had been a few months since my last Stepping Out adventure.  My wife came home from her trip, and I grew my facial and leg hair back.  Summer started, and although I had some urges to shave my legs again and go out, I knew that I couldn't because I would be attending pool parties and the like, and I would be wearing shorts on a regular basis.  (My wife would not have been happy if we had to skip social events because I chose to impulsively shave my legs one night.)

And I agree in a way.  As much as I've embraced my feminine side, the last thing I would want would be to have someone recognize the fact that my legs were shaved in a social situation.

I could just imagine, being at a party, laughing and telling a story, and someone would casually look down and say, "Are your legs...shaved?"

That would be an uncomfortable moment.


Even though I knew that masculinity and hairy legs was part of my reality for summer, I still often felt the urge to put on some women’s sunglasses, a flirty short summer skirt, and a pair of sensible heels, and go out in public so badly.  Something inside of me just wanted to go out again, and experience that feeling, and those nice summer days were calling my name.

I had a few days off, and knew that what I really wanted to do with them was to dress up and get out of the house.  The problem of my hairy legs required me to have to wear tights with my high heeled sandals.  Recently it has been in the hundreds of degrees here during summer, and the tights looked a little strange considering the weather, but they don't look completely out of place either.  They looked more like stockings and not thick winter tights.

Another difficulty was that I really didn't want to bother with too much makeup this time.  My wife can always detect the slightest bit of mascara or eyeliner or sparkle from eye shadow, and I didn't want to hear it if she happened to scrutinize my face that night.  Besides, I really don't like putting on makeup sometimes.  (I know, I know - I should like it if I were a true sissy.)  Sometimes, though, it seems like such a hassle to put it all on, just to go out on a little adventure.

Maybe I am truly a girl, now I'm complaining about how I don't like putting on makeup ; )


Considering all of these factors: heat, makeup, tights; it would have been easy just to stay inside, but something inside me forced me to get the initiative to go out.  To make it an easy adventure, I just decided to drive around in my car.  That was easy enough.  Still, I had an idea that maybe I could go to the park if it weren't too hot.  I hate sweating up my pretty clothes.

I dressed; put on some foundation, lipstick and blush; and put my sunglasses on to hide my face.  As I drove around those two days, I began to think about how crossdressing is so much an act of isolation for many of us.  It's a secret and we don't want to get caught, but some part of us desperately wants to express it to the world too.  It's an interesting dichotomy.

That was how I felt.  I was out, but I was still alone.


Another thing that I found interesting was that although I haven't been out dressed that many times, now it almost seems a bit commonplace to be out on the street in a pair of heels and a skirt.  Whereas it seemed so naughty at one point to step out into the world in panties and a dress, now it just felt like clothing, and not such a big deal.  I mean it was clothing that I liked, and I felt pretty, but I didn't have a fluttering in my heart like it was such a crazy, dangerous, titillating thing to be outside in the world in a skirt and panties.

I guess that's a cautionary warning for some of you.  Once you step outside of that door, it's no longer a fantasy.  There are no more hot moments wondering what it would be like to be out in the world dressed as a girl, because you already know what it's like.

And that's how I felt that day - I know what it's like now so it's not a mystery.  Those heart-pounding moments of stepping out the door are gone.  The trepidation is still there a tiny bit, but the fear is gone. 

To tell the truth, I don't even feel like it's such a crazy thing anymore.  The first time I did it, some part of me inside said, "Are you sure you want to do this?  I know you have a fantasy, but this is dangerous.  This is so risky.  Are you really going to do this?"  I had such a guarded feeling inside the first time I trepidatiously walked around the open world in my heels with my purse on my arm, knowing that this was wrong in the eyes of society.

But now when I leave the house, my purse is on my arm, I feel confident in what I'm wearing, and I lock my door just like any other day when I'm leaving my house and walking to my car.  Basically it's me in a dress or skirt, and it doesn't seem so strange.  I guess since I've been in a crowded store wearing a dress before, just walking to my car in a skirt to do a little driving does not feel dangerous at all anymore.

Don't get me wrong, I'm not saying I've lost anything.  I still love the feel of being out in the world the way I'd like to be, but it's strange how quickly I've become used to it, like it's just an everyday thing.  There's an element of normalcy in this new feeling, like maybe it really isn't such a big deal if I'm wearing a dress.  It's as if I was expecting a quick, hot sexual thrill, but instead found something completely different.


This last time I went out, I noticed that I went through different stages during my journey.  At first it seemed a bit naughty being outside in women's clothing, then it left, and there were moments when I got caught up in whatever activity I was doing (like driving and walking) and almost forget about the fact that I was wearing women's clothing in public.  This time I was just driving, and I had to remind myself, and say, "Hey, you're in a skirt and bra with a white shirt for all the world to see.  Look, there are people all around you looking at you.  They see you as a girl," and it felt good realizing that I was being seen in my white tee shirt and bra again, even if I was just driving a car.

But as I drove around that time, with nowhere to go, I kind of mused about my need to go out.  What was the need, the urge to be outside as a woman?  Why did I feel a need to be among members of society in my secret clothing?  I kind of knew the answer and continued to drive. 

Since I had nowhere to go, just driving around aimlessly began to bore me just a bit.  I looked at all the stores and places with people going by, and dreamed of going beyond just walking into a store, and instead wanted to interact with people.  In the moment, I realized that didn't care if they knew that I was a man or not, I wanted to be recognized for who I truly was.  That’s all that mattered.  The whole future of everything played out before me.  I didn't want an isolated experience.  I wanted to be myself, it's just that is seems to be a seemingly difficult and impossible journey to take.

But that brought up a dilemma.  Being seen as a woman seems almost impossible, but being at home is an isolated experience.  Even stepping outside my door and getting in my car is still kind of isolated because I'm sneaking around trying not to get caught.  Even the bold step of going to a crowded store was an isolated experience in a way, since I hid behind my wig, and sometimes looked away from people's gazes, and walked the other way when somebody approached me.  Even when I spoke to people at the store, I was hiding behind my personae, pretending to be someone that I wasn’t.

No, I don't want to be isolated.  I think I need some sort of affirmation from society.  I want them to know.  I want them to know that I feel more comfortable dressing and acting like a girl, than I do pretending to be just another regular guy.

For now, that all remains a fantasy, and it makes me think: If I cross that fantasy line, will I have that feeling that it's not so much a big deal either?  Because like I said, walking out of the house the other day, I was in a skirt women's tee shirt, and a wig, and locking my front door, it felt as normal as if I were doing it in male clothing.  It was kind of a strange feeling.

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