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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

My Cinderella Story

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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