Sarahjanus's Blog

November 23, 2010

New jeans, another milestone,

I gave in today and bought the jeans that I had been resisting. It’s not that I was resisting a given pair of jeans. I was fighting the idea of wearing jeans versus wearing skirts, dresses or leggings. I have been clinging to the fantasy that I can dress as a woman without regressing to jeans.

In my simple mind, my ideal would always be in skirts, dressed as attractively as possible. I wasn’t interested, or so I thought, in dressing at a level where the lines were so easily blurred. I wanted to be clearly feminine. As it turns out, that was just another milestone like so many others before it.

When I first gained the freedom to entertain my fantasy of dressing as a woman, the boundary was skirts and tops. I wore them because they were comfortable and they gave me a peace of mind that was missing otherwise. Then I progressed to adding shoes. The funny thing is; I had purchased shoes and nylons years ago, worn them when I could and eventually threw them out. I love nylons and shoes. I would spend a fortune on those two things alone if I was free to do so.

After the shoes and nylons, came the bras and the Walmart add-a-cup inserts. Of course, that didn’t suffice for long. I ordered a set of forms from Stephanie’s Bosom Buddies. Those arrived the day I was leaving for a cross-country drive. It’s hard for me to believe that it was only April of this year that I got those. I have grown so much in the past few months.

While I was on the road, I wore the skirts and tops. I was a man in a dress more or less. I didn’t have a wig, or make-up. I didn’t have underwear and I wasn’t completely comfortable with the forms yet. I was comfortable in the clothes.

Over the summer I added a wig, make-up, and enough underwear to last a month, more nylons, more pairs of shoes and four dresses, plus leggings and the appropriate long tops for them. Now I’m not comfortable if I’m not complete.

The transition to wearing bras and forms was a milestone. It took me from being a man in woman’s clothing to someone who wanted to be seen as a woman. The wig was part of that same change in thinking. The make-up was another milestone. It meant that not only did I want to be seen as a woman but I wanted to be seen as an attractive woman, all things considered. I wanted to be seen as someone who cared for herself.

The underwear and tucking was another milestone because it meant that I was completing the picture, even if it couldn’t be seen by observers. I knew that I was working on a complete transformation. I wasn’t a faker, I was trying to be as real as I could.

I began to buy my own jewelry because I wasn’t finding anything I liked in my wife’s. A trip or two to the mall and I had the beginnings of a selection, another mental milestone.

My two journeys out of the house were also milestones because I was prepared to involve myself in the real world as I wanted to be seen rather than as I had been for the past 50 years. The journeys out also drove home the point that real women wouldn’t always be wearing skirts or dresses; that I had to accept the need for slacks and jeans in my wardrobe.

Today I bought the jeans. Now I can wear them with the other parts of my wardrobe and not stand out quite so quickly as the only dress for miles around.

Each of the milestones has been significant for me. Each has meant that I am changing, changing how I see myself, changing what I see as acceptable, acknowledging that this is not a flash-in-the-pan indulgence. Each milestone has meant that I have surrendered a bit of my masculinity and adopted a part of my femininity.

I have a pair of pant shoes with heels that I will be trying on tomorrow with my new jeans. I tried the jeans on “just quickly” when I got home. I have no “behind”. I wonder how I’m going to fix that. I’m looking forward to seeing casual Sarah tomorrow. I thought she was just a business attire or dressy girl. Now she has another facet. It should be interesting.

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