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Connecting with My Crossdressing Roots

crossdressed in a silk blouse and white braThis has been a fun weekend for me, and I often noticed how much I was returning to my cross dressing roots. What I mean by that is more than spending time thinking about that next adventure or seeing how far I can push myself by doing something daring in public while dressed as a girl, I just felt like doing simpler things and enjoying the simplicity of being a girl. Having said that, I did buy a new bra this weekend, I did do some clothes shopping, and I did go to Wal-Mart for some new makeup, and I will talk about all of those outings in the next few days, but in this diary entry, I want to highlight a few examples of how I returned a bit to a more simplistic approach to my cross dressing.

First, for the strangest reason I had this strong desire to wear the very first blouse I purchased after I was married. This is the blouse that I wore for that first Halloween when I came out to everyone and cross dressed as a girl. The blouse is 100% polyester, it has an old-fashioned lace collar, and it even has shoulder pads. I mean, how 80's can a girl get?! Yet, for a reason I can't explain, I really felt like wearing this blouse with a conservative skirt, suntan pantyhose, and a simple pair of pumps. I couldn't think of a place to wear this outfit, but when I put my fashion photo shoots together this weekend, the very first outfit I wore was the one I am pictured in here.

crossdressed outsideAnother example of this desire to get back to my roots came after the golf outing that I talked about in my first update. I went golfing first thing in the morning because I wanted to enjoy the cool mountain air and finish before it got too hot, and once I finished, I still had the entire afternoon ahead of me. I was really undecided as to what to do, and I could have gone shopping or gone to an early lunch, but I felt this strong desire to just take a walk for an hour or so through the woods and near a resort that was close to the golf course. Before my walk, I needed to go home for a bit to freshen up, and while there, I changed my skirt from the khaki skirt I wore golfing to my favorite denim skirt. I also needed to fix my hair which had become a bit tousled after wearing that cap all morning. Once I was ready, I took off on foot to walk along several paths into the woods in order to enjoy the fresh air and changing leaves.

The path along which I walked has benches here and there, and so I thoroughly enjoyed taking small breaks and sitting down cross legged just taking it all in. When I was in high school and even in college, I still wasn't able to successfully cross dress in public, and so my outings were limited to walks such as these where I could get off of the beaten path and find a place to just sit and relax. One of the big differences from then and now is that when I was younger, I only took my walks late at night. Many times, I also looked like a boy from the neck up, and so I avoided people at all costs. Today, however, I took my walk in the light of day and never shied away from people nearby. Of course, I looked like a girl, and so that made it easier, but just felt good to have some quiet time as a girl and reflect on my life and how I have come to this point.

It was this same kind of reflection that often kept me up late at night in my younger years wondering who I really was. I would never discover that until after I was married, but it was a wonderful topic to keep me awake until I could sneak out of my house or apartment and actually take a walk outside wearing clothing that truly fit my gender. From a young age, I quickly realized that special sensation of cool air touching shaved legs clad in nylons or the security of wearing a bra, and today, I believe I was trying to reconnect with those feelings of my youth.

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My Crossdressing Relections

Autumn Photo Shoot

Mommy memoirs from the ballpark

Psychological need for bras

Crazy night at the ballpark

In the mood for pink

Long overdue photo shoot

A girl and a flower garden

Signs of a Girl

Challenges of being a girl 24/7

Quiet Picnic as a Girl

Why My Bra and Panties Rarely Match

Dimensions of being a girl

Pantyhose here and there

Connecting with my cross dressing roots

My slip is showing

Crossdressing and Halloween

Sunday Morning Walks in a Dress



My Biggest "What If?"

Mornings as a Girl

My Mother and My Crossdressing

Motherly Feelings While Crossdressed

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