Brian to Brenda

My journey to being a woman.

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I am Brian Gladstone born a male and living most of my life as one. As I have aged and accepted my feminine traits, I have also accepted I should pursue being a woman and starting transition to becoming one. I will begin HRT in 2027 and after those change stabilize a little finish my transition with breast augmentation and facial feminization surgery. The blog is really about where I came from and my transition. A little about my feminine style and how i will present myself as a woman.

    • My Journey in Women’s Dress Boots: Brian Gladstone’s Transition to Brenda Carr

      One of those things you really won’t know until you try it was putting on my first pair of women’s dress boots. As I document my male-to-female (MtF) transition journey from Brian Gladstone to becoming Brenda Carr, I remember wearing this burgundy suit and it didn’t feel right in standard heels. I had always wanted ladies’ dress boots, and finally managed the courage while on a business trip to buy a pair at the mall

      Finding Feminine Confidence as Brenda Carr

      I rushed back to my room and started to get ready. One of the first times I used press on nails to get a women’s length and then applied a matching nail polish. Spent some time getting my makeup together and then got into this suit. I really liked how it looked. Then adjusted my wig and finished with some Revlon lipstick. Finally time to head out and so some shopping so I got out my new boots.

      The Freedom of Crossdressing and Transitioning

      There are few things more feminine than placing your foot inside a ladies boot and side zipping the shaft. Grabbing my purse I was anxious to see how I looked. I make no pretense at this stage to be a passable women, but one can draw these conclusions I clearly enjoyed the experience of being in women’s clothes and walking around in dress boots. In my Brian and Brenda side by side, almost all people say they prefer my appearance as Brenda and look better feminized.

      I also enjoyed shopping in my skirt suit and boots, I was bolder less timid. I enjoyed passing by men and seeing if they looked. I was always a bit squeamish being around men, not feeling I belonged. There is a freedom of expression when not passable but feminized that says, yes I am a male, but not a man. I am not going to hide it anymore, I am going to say it out loud, being in woman’s clothes, wearing heels, makeup and lipstick applied, pursed and perfumed, no man here, lets get on with it.

      I still very much enjoy shopping and wearing ladies dress boots. I expect as I transition to a full time woman that dress boots will be a regular staple of my style and fashion.

      A side-by-side image featuring a man in casual clothing standing by a door on the left, and a person in formal attire, including a long coat and boots, posing with a handbag on the right.
      Side-by-side comparison of Brian Gladstone in male clothing before his MtF transition to Brenda Carr, wearing a feminine burgundy skirt suit and black dress boots.
      A person stands confidently in a hotel room, wearing a tailored maroon suit with a purple blouse. They hold a small black handbag and are wearing knee-high black boots. The background features striped curtains and a beige couch.
      Brenda Carr, formerly Brian Gladstone, wearing a burgundy skirt suit and black women’s dress boots during her transgender journey.

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    • Brian’s starting road to being Brenda

      A person standing in a hotel room wearing a bright pink jacket and white pants, holding a white handbag, with an elegant hairstyle.
      Brian Gladstone dressed in woman’s clothes.

      My story is similar to many transgenders. Born male, as I grew up it, being male never seemed to be a good fit for me. I was shy and a bit timid. My height ended up being an average woman’s, well below a average mans. I had relatively small hands as well. Above all I was feminine. I wanted to wear woman’s clothes, makeup, and appear as woman do.

      Suppressing these feelings most of my life probably lead to depression, alcohol abuse, and eating disorders. Finally later in life I decided I really needed to explore my feminine side. I started to assemble all of the items needed to allow me to cross-dress. My first attempts were very rough, and a bit discouraging. I kept at it, and bought a little more stylish clothes, higher quality wigs, nail tips and polish, and worked more on makeup. Finally one day, after slipping on some pumps and looking at the mirror, I saw her. Not a passable woman, but the potential for someday becoming one.

      So for my journey, I suppose every woman has a style. Mine is understated or refined feminine. I am not one for wearing stilettos and short skirts. I do like bright florals or colors, medium length hair, jewelry subtle but there. Medium length polished nails are my go to. I really like a medium cross body purse like the one pictured. Heels, yes I like wearing heels. 2 1/2 inch is probably my max height these days. I consider the classic white pumps I am wearing here timeless. A noticeable lipstick is always part of my appearance.

      While dated I think the above picture does say a lot about my style and aspirations. Again the first person noticing I am not passable is me. Still as I finished with my wig and makeup and slid on these heels, the picture represents the real Brian Gladstone more than any of me as a man. Flaws and all and even before starting feminizing hormones, I have a lot more potential as a woman than ever as a man.

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