After almost 50 years of strutting around in my high heels, I’ve learned a few things.  First is my ability to laugh now at what wasn’t always so funny back then.  I may have only been five or six, but I did wear my mother’s shoes — what kid doesn’t; it’s cute.  I’m not sure if being a crossdresser bears a rite of passage, but many of us have similar stories.  I have always been able to laugh at my male self, but found more tears in my journey to become Brina than laughter.  Today, Brina is mostly put together, better at passing, and deeply rooted in my psyche.  She can even laugh at what has gotten us to this place in our lives.

But that one time …

My mother had found three dresses in my closet that I bought at a garage sale when I was in high school.  They were buried deep and reason that she was in there at all is something I still don’t know.  Sometimes fate just has to bite us.  I told her my friend was going to run away from home and wanted a disguise.  It sounded good back then, and I thought I got away with it.  I was scared, however, for months afterward worrying that my mother might ask me more about it.  She never did.  Now I laugh at the lie and realize the she might have figured they were mine.  I have never have come out to her, or my father.

Or the time …

My ex-wife went to work only to come home thirty minutes later to find me wearing her prom dress.  This was during our first year of marriage — back when I thought all I had was a fetish for high heels and slinky dresses.  What makes this story funny is not being caught.  That was a nightmare and became a wedge between us that never healed.  My ex-wife ended the talk by telling me that if she ever caught me again, we’d be through.  Twenty-two years later, she did and we were.  What is hysterical is the fact that the dress was way too small and stuck on me.  I had eyed that dress in her closet for nearly a year.  That was just the day that I had to try it on, or should I say, to force it on.  I felt beautiful wearing it with the zipper only two thirds of the way up.  My ex-wife came home; I raced into the bathroom and could not get out of it.  I ended up slipping and falling into the bathtub.  She threw the dress away along with my shoes and the pair of her underwear which I was wearing.  Did I stop, even after I promised her I would?  You know the answer to that; I just got better at hiding it.

And then there was the time …

I had a few other narrow escapes during our marriage.  Really, the marriage was over long before I was caught.  Thank God for PO boxes and online shopping.  Fourteen years ago, I ordered a pair of 8-inch white platform heel stripper shoes and a striped baby doll nightie.  I was overweight, hairy everywhere including a beard, and totally stressed out.  You know the drill — the more stress the more the need.  I still had not come to terms with who I really was, believing that the brief moments when I would buy, wear, and dispose of my girly items were just a shameful part of me that I could not control.  I also had a new digital camera.  Stupid me thought let’s take pictures and put them on the computer so I could get a better look at them.  I even did some naughty poses — you know because you have to.  Looking at photos on the computer did not bring satisfaction, only shame.  I deleted them, emptied the recycle bin, and hid the shoes and lingerie in my golf bag.  Yep, one picture wasn’t deleted, and it absolutely had to be the worst one imaginable for my ex-wife to find.  I wish I could have taken a picture of her face, both when she found it and when she told me about it.  The first one was probably shock (I wasn’t home), and the second one was gleeful evil as she kicked me out of the house.  It is funny now, but it was the best thing that happened to me and should have happened sooner — not the pain of being caught, but getting out of a dead marriage.  Brina was born after that and she has been nothing but a blessing since, even when I put her away for seven years to try another relationship.  Her voice has always been the one telling me that I’m ok and to take it a day at a time.

I think we all have that one item that we cannot live without, at least not for very long.  Mine has always been high heels.  With size 12 men’s feet, it has been a challenge, and having narrow feet besides, even more so.  I have bought lots of shoes because I had to (they were calling to me), and they did not come close to fitting.  Once during my marriage, I walked by a shop in a mall a dozen times before I found the courage to buy a pair off the rack.  They had an ankle strap and closed heel and toe, but open in the middle.  I made them fit, or should say, made my foot fit.  I loved those shoes, keeping them for nearly five years.  Over the years, I cut out the toes and part of the heel closure to give my foot some room.  I cried when I snapped one of the heels and no amount of nailing and gluing would fix them.

When Brina started her wardrobe, the first pair of shoes she bought had 6-inch heels and no platform.  I could sit and wear them, but not walk in them.   In fact, I fell and twisted my ankle twice, which led to a couple of interesting stories.  I wish that I still had the video of me trying to walk in them — it wasn’t funny.  I also would like to have any of the pictures that I took documenting Brina’s arrival and her growth.  Why?  Perhaps, it is because I would love to laugh at them today.  Unfortunately, I only kept my last four years worth.  Just as adults can look back and laugh at themselves during their growing years, I am comfortable laughing at my own becoming.  This journey has been more important; it’s brought me closer to being a whole person and figuring out what real happiness can be.

Today, I am not alone, and I never will be again.  It’s possible that I will not find another person with whom to share my life and who accepts both parts of me, but it will not be that I won’t look.  If I don’t, I will be at peace because there are many sisters out there who love to walk in the same pair of heels in which I do.  And that is a comforting thought.

The following two tabs change content below.

Sabrina (Brina) MacTavish

Brina is from Iowa, and she is steadily learning how to merge her two halves into one whole. Still closeted after 40 years, she hopes to one-day walk freely and confidently in the open. She spends most of her time working as a self-published novelist under both personas.

Latest posts by Sabrina (Brina) MacTavish (see all)

  1. Marianne 2 years ago

    Hi Brina!

    I love your post, though I find it a little sad that your wife couldn’t accept your dressing. My wife is not overwhelming joyed, but she accepts it beingn a part of me as long as I keep it discrete and she doesn’ t have to participate. She’s mostly a little yealous that I can still fit into her ball gown and wedding dress white she can’t after 22 years and three children. Four years ago we had a small crisis when she found out I was sewing a full length fitted gown for myself. One night, the zipper got stuck and I had to ask her to help me get it down. That was the first time she saw the whole design, and later in bed she admitted that she had expected me to look ridculous, and instead found the gown look fabulous on me. A few dags ago, she needed to use the sewing machine and was a little startled when she found it loaded with red thread from my latest project. She happened to break the needle while trying to mend a tent and didn’t bother to repade it. “There are replacements in the utility compartment in case you ned to sew something” she said then she put the machine away. And the other night she didn’t say a word then I stood there pressing the seams of the red dress then she went to bed.

    • Author

      First, I’m jealous of your sewing ability. I’ve never learned. Tolerance is the next best thing to acceptance. I have no idea the path that would have been if the ex had been tolerant. The sad thing is that she and I were the type of people that married each other for all the wrong reasons and tried to make it work, and then once the kids came, turned our focus on them. My dressing wouldn’t have changed all the other negative things. If she saw me in my pictures today….whoaaaa would she be spitting mad. She wouldn’t be able to fit into my dresses and she can’t walk in heels…. sometimes there are little wins….

      Have a great day and thanks for sharing,


      • Marianne 2 years ago

        Thank you Brina.

        A little about my sewing experience.

        My mother always claimed she wouldn’t let her children leave home without some basic abilities. Those included cooking three different meals, bake a cake and keep our clothes clean and proper. She was then, and still is, a very competent seamstress, who for economical reasons learned to redesign old clothes given by relatives for her own use in her early teens. She more than once told us the story how her textile teacher, well aware of her circumstances, one spring called her to stay after class. She then retrieved a bolt of new cloth, handed it to the young girl and said “This shall NN sew herself a skirt from”. So we all learned some basic sewing and knitting as well. And sometimes I helped her laying out the patterns or making fitting adjustments. She later on sewed me a tuxedo that I wore to a ball together with my fiancee, and then again at our wedding. She also sewed parts of the wedding gown, that was a gift from my sister, who by then had her private sewing business. The conclusion of this story is that I really came to know my way around patterns and needles but sadly had no chance to make the clothes I was dreaming of. Many years later, I suddenly saw my dream gown on a Swedish buy and sell site on the Internet. Sadly it was only a size 8, but the ad also mentioned it was home sewn. After some serching, I found the pattern and a nice brown satin duchesse at a fabric retailer. The pattern was from Germany based Burda and was followed by excellent multilingual instructions covering everything from measuring yourself through cutting out the pieces unto putting it all together. I started cutting cloth and sewing in secret, but slowly my wife became aware of my activities and started questioning my actions and wondering whenever I would have the possibility to wear such an outfit. I was however allowed to finish it since only the sleeves and bottom hemline remained unfinished. The aftermath, eventually causing most of my collected clothing, shoes etc end up at Salvation Army is a story for another rainy day.


  2. Jennifergordon 2 years ago

    Hi brina! That is a beautiful story about the high heels. For myself I live in constant fear that I will be caught in my panties and stockings. I live alone and those fears follow me everyday. Without the clothes I become depressed and the anxiety escalates. I will not stop because the dressing gives me the security and calm that we need. My days of fighting it are long gone. I love hearing stories like yours. It gives me reinforcement that I am ok and a special human being. We all have to stay strong and love each other. The best to you! Jennifer

    • Author

      Thanks for your comment! You are spot on about the anxiety that builds when NOT being able to dress. I agree about the depression. It’s worse not dressing than it is to be dressed and worry about being exposed or having someone find our things. The hardest thing I had to come to terms with is this: I am a decent human being and what I wear on the outside has nothing to do with the kindness I share, the heart that I bare, or the love that I can give.
      Stay proud, stay strong.

      • Monica Brown 2 years ago

        That is so true cuz I’ve had my daughter now for 2 weeks and I haven’t been able to do anything and I feel like drug addict feinding got that moment I can put my nails. Walk in my heels and put a little skirt ..yes I said little skirt .tho my dressing has evolved at this moment I am so ready to look like a hooker lmfao

  3. Ashley Newberry 2 years ago

    I LOVE crazy high heels and I’m damn good at walking in them. I was in high school 98 to 02 when the Spice Girls were doing their thing. I hated their music but still paid close attention so I could always see what platforms they were wearing. And then for the last couple years platforms have come back a bit but now they’re tapering off again. That means chasing down all the shows I’ve coveted over the last couple years on eBay and Poshmark since they aren’t made anymore.

  4. Charliene Gaudiosi 2 years ago

    Hi Brina,

    That is a very insightful story. I have come to similar conclusions about my own behavior reguarding stress. I am a part time crossdresser and my wife and therapist are encouraging me to find some like minded friends to spend some time with to get the validation that I am looking for. It is difficult when you are looking for a reasonably attrective person but not interested in a sexual relationship.


  5. Scott 2 years ago

    I got caught in my neighbors house wearing my friends moms clothes when I was 11. It was embarrassing to say the least but relieving. She called my mom to come over to see what I was doing. That was the worst part. Now I’m older, 43, and absolutely love dressing in skirts and tights with heels.

  6. Emily 2 years ago

    Love this! So many times I’ve almost been caught. My dressing did cause the end of a relationship as well. Now that I am older, wiser, bolder, and more sure of myself, I worry less about getting caught.
    Finding the opportunities to go out dressed have helped immensely in being sure of who I am. I have also told a few people outside the transgender world. That, has been very liberating.
    Here’s to many more years of being able to laugh at ourselves.

    • Author

      There comes a time when you no longer play at being female or acting like a character and instead put on your skirt and heels knowing that is what makes you happy and what you should be wearing. Looking in the mirror is seeing a reflection of who you are (and truthfully, some days it’s all male) and being able to say with a straight face, “Damn that color makes my butt look big!” lol.

      Thanks for the comment!

  7. Great story Brina…..just loved it. I guess we all go thru this in our lives….”right of passage?” Glad everything worked out rather well for you. Keep looking for a soul mate….they are out there, sweetie.
    You would think that with all of the strife in the world, wearing a different outfit should be the least of others worries. Oh well, someday, we will be another girl on the street. All of us look like we take great pains and expense to look fashionable….do you think the others are jealous? I don’t care about them, I am happy being me!

    Lady Veronica

    • Author

      I agree. There is a liberating moment when we put the shame and guilt behind and accept that it’s okay to be us. Even better when we realize how much happier we are when let our true selves come out and play without fear.

Leave a reply

Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account