A Hodgepodge submission

Since my crossdressing began anew, after a very long dormant period, I have purchased at least six bras only to donate them all to Goodwill because they were uncomfortable or just didn’t fit. This has been a big frustration for me, as I imagine it is for many of us. The rest of my wardrobe has steadily grown these past few months. I’ve progressed from just shopping online to using the self-checkout line at Walmart. I’m also shopping in the women’s section of my local stores; even using the fitting rooms to check out my purchases before taking them home.

And as my wife has adjusted (more or less) to the fact that her husband is a crossdresser, we have gone out shopping together. We recently bought matching tops and panty sets. I’ve also embraced this aspect of my life, and with the support and advice of CDH and its members, I’ve become bolder.

Transgender Heaven - Gender Journey

But boldness has its limits. Many others have asked for advice about bra issues, and the advice given has almost always been the same: Get a professional bra fitting. Dillard’s has been the most-recommended site for this.  The thought of wearing drab, walking up to an unknown saleslady, and announcing that I’m a crossdresser who needs help with a bra fitting was ….intimidating.  Nevertheless, I finally decided that a girl’s gotta do what a girl’s gotta do.

A chore for my wife sent me downtown and very near to a Dillard’s store.  I completed my chore, and then headed to Dillard’s and up the escalator to the lingerie department.  I located a saleslady and made my request, in a soft and somewhat raspy voice (it was a very hot day, and my mouth was very dry).  She was totally professional, helpful and friendly.  I was escorted into a private booth, measured and found to be a 36 A, as I thought I was.  Having no idea what style I wanted, other than unpadded and comfortable, I was given two bras to try on.  The first failed the comfort test, but the second – actually a 36 B – was perfect.  I chose it and asked for another in black, which was not available.  I settled for the one bra, now knowing the brand, size and style for my future purchases.

Why a 36 A body requires a 36 B bra is a mystery; but as the saleslady noted, my “girls” are not the same size, so maybe that has something to do with it. It doesn’t matter at all.  With my wardrobe finally complete, I can say Bettylou is now a real girl.  Now bring on that makeover!

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Bettylou Cox

Retired USAF Flight Medic; Retired FD Paramedic. One wife, 4 children, 8 grandchildren. Part-time small animal rescuer. "Dressed" as a teen; ended w/military career & marriage. Urge resurfaced ~ two years ago. Essentially starting anew, and really enjoying this new lifestyle. I find that Betylou is rapidly evolving into a full-time persona.

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Vicki Smythe

I had a professional bra fitting done at Soma as well. I asked for the manager to make sure it would be ok and when a good time would be for me to have a fitting. I didn’t want to upset their clientele or possibly some of the sales staff. I came back at the recommended time and was taken to the dressing room and measured. I came out with several bras and matching panties. I returned several more times since then and they have always been kind and recommend different styles and let me know when sales were coming… Read more »

Janice Emory

Another terrific online resource for lingerie, once you know your sizes, is AdoreMe.com
I have purchased bra and panty sets and single panties with no complaints. I had one problem
ordering panties that did not have an elastic waistband but that was my fault for ordering them
in the first place. I wear unlined, wired bras which are very comfortable. If they don’t display your size
(mine 46C) They will suggest a substitute (for me 44D) an it worked out well. Check it out, you may like it.


Thank you so muchBettylou! i have a couple of bras but have setgetting a regular bra fitting as part of my plan for 2019. I also want advice incisive for breastforms. Could i get thatatDilards?

Michelle Johnson

Good for you!! Fair warning… bra fitting can become addictive. My first was exhilarating to say the least. Now I know every lingerie sales woman in several local stores and they seem to look forward to seeing “Michelle’. Recently one of them ,Jessica, ordered a beautiful babydoll set and had it shipped to my address… just because she likes me so much. Bra fitting took it to the next level of heaven!!

skippy1965 Cynthia
Trusted Member

Bettylou-congrats on stepping out of your comfort zone and thank you for sharing your story here. You give others courage to take the next step in their own journey-whatever that may be.

Dorothy Brinson

I had read an article about men wearing bras. I had learned that most can get a bra fitting done at local bra boutiques. I had my first bra fitting done at a store called Ann’s Bra and Masectomy Shop. The ladies have all been so wonderful. All I have to do now is walk in and they know me by name. I love this store.


I was nervous when I had my first fitting. I previously had bought bras online but hadn’t gotten a good fitting until I went to Lane Bryant. The saleslady was calming and kind, she sensed my nervousness but reassured me I was welcome and she put me at ease. She measured and helped me with a bra and hugged me telling me I was part of the family and I was always welcomed there. Needless to say I now have an account and have bought many things from them. My ultimate goal is to go fully dressed rather than underdressed… Read more »

Danielle Silverfeather

My lady outfit came from Lane Bryant. My first bra fitting was trying on my sister-in-law’s one. I was alone in my brother’s house. Her bra fit great on the lower part. Her cup size was too small for my forms. So I went as a male and got the cup size I needed.

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