Brian to Brenda

My journey to being a woman.

recent posts

about

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.

    • Crossdressing Confidence: Brian’s Feminine Fashion Choices

      Crossdressing Confidence: Brian’s Feminine Fashion Choices

      Top is Brenda Carr, below was a couple hours earlier in male mode Brian Gladstone. Most people think I make a better woman.
      Brian Gladstone crossdressed as Brenda Carr

      I’m bringing back one of my more feminine outfits from my crossdressing days. I’ve mentioned loving pink in previous posts, and this look is another perfect example. It’s an undeniable piece of feminine style: a soft flowered scarf serving as the perfect accessory, paired with a bright pink, stylish blazer and matching tailored pants.

      I remember when it first arrived in the mail—I actually hesitated for a second, thinking it might be a little too feminine for me. That thought didn’t last long. Looking at my options, standard white pumps just weren’t going to do this suit justice, so I chose a pair of low-heeled, dainty pumps instead. I usually just polish my nails, but when I found these long French manicure press-ons, they felt like the exact right fit.

      With my reservations gone, I put the whole look together. As I started applying my makeup, any lingering anxiety melted into excitement. The suit went on smoothly, feeling comfortable and fitting well. I paired it with one of my favorite medium, shoulder-length wigs and finished my face with Revlon’s “Love That Pink”—my absolute go-to lipstick. The low-heel pumps were spot on—comfortable, offering just that single inch of height the outfit needed. Finished with a stylish white crossbody purse, the ensemble came together beautifully. Emotionally, seeing the complete image in the mirror felt amazing.

      Like my other recent outfits, this look presents a clear, feminine style. While I know I’m not entirely passable, I feel infinitely more comfortable walking around in public dressed like this than I ever do in men’s clothes, where I always feel out of place. Presentation like this eliminates the pressure of trying to force myself to fit in with taller, stronger men who intimidate me. Out in public, an outfit like this does all the talking: I am feminine, I am not trying to be a man, and I am entirely comfortable with that reality.

      When I transition and live as a woman full-time, this might not be my everyday wear, but you’ll definitely see me bringing it out on a monthly basis.

      Fediverse reactions
    • Embracing My Identity as a Sissy

      Embracing My Identity as a Sissy

      Shyly saying, yes at my core I am a Sissy. Many don’t like the term but I don’t know a better one describing me. Probably wrong, but my confidence goes up dressed as a woman.

    • Embracing Pink: A Journey to Femininity

      Most males resist wearing the color pink. Then there is me. I like pink, I like even better to be wearing pink. This pants suits is one of my more – feminine choices and not exactly ready for prime time. Still, there is a lot to said for nails brightly polished – pink, woman’s clothes bright and bold pink, and a very bright lipstick to match. Paired with classic white high heeled pumps, and a cute white purse, yes this an outfit I am happy to present myself in.

      Yes, I did actually go out in public like this. Yes, I did get a fair amount of awkward “looks”. The reality is hearing the clink of my heels on the pavement, the putting on Revlon “Love that Pink” lipstick still felt more comfortable for me. Ultimately I am feminine. Wearing a bright pink ladies pantsuit is more natural to me, than any pair of Nike sneakers will.

      Again in side by side comparisons the vast majority think I look better in pink than a male. Who am I to argue. I accepted a long time ago, I prefer being a woman.

      Brian Gladstone in ladies pink pants suit.
      Brian Gladstone dressing in woman’s clothes.
      Brian Gladstone crossdressed as Brenda Carrr

    • Exploring Feminine Fashion: Outfits That Empower

      A person standing elegantly in a floral blouse and black pants, holding a small black purse, in a well-lit room with a sofa.
      Love Black Patent Heels.
      A person lounging on a patterned couch, wearing a colorful blouse and black pants, with makeup and styled hair.
      Pretty blouse.
      A person sitting on a patterned sofa, wearing a floral top and black pants, accessorized with black heels and holding a small handbag.
      Brian Gladstone in woman’s clothes.

      I could never be a man—it’s something I’ve known for most of my life, and I’m not ashamed to say it out loud. Dressing as a woman simply aligns me with who I actually am and how I’ve always felt.

      This outfit is easily one of my favorites: a feminine purple floral blouse paired with straight black pants. It’s versatile and gives me room to play with the fashion choices I love. First, it’s perfect with a pair of shiny black patent pumps and a matching purse. It also demands a bolder look—bright red nail polish, vivid red lipstick, and silver jewelry to wrap it all together. It’s comfortable, put-together, and ready for a movie night.

      While I might not be fully passable going out on the town dressed like this, it validates something core inside me. Standing at the height of an average woman and actually dressing like one finally brings the outside in sync with the inside.

      There’s also the element of pure comfort. Going out in public presenting as a male is an ongoing struggle for me. I get timid. Because of my height, I’m always looking up to other men, and frankly, I feel intimidated by them. But stepping out in an outfit like this? It erases all those doubts. I’m feminine. I’m walking in heels, carrying a purse, and wearing a distinctly feminine blouse. I feel completely aligned.

      I’m not trying to be something I’m not. I know I could never be a man, but with practice, hormones, and surgeries down the line, I can and will be the woman I am inside.

      Fediverse reactions

    • My Journey in Women’s Dress Boots

      One of those you really won’t know until you try it was putting on my first pair of women’s dress boots. 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.

      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.

      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.

      Brian Gladstone and Brenda Carr, almost all people prefer me as Brenda.
      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.
      Enjoying the experience of wearing a skirt suit and dress boots.

      Fediverse reactions

    • 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.

      Fediverse reactions