Ask Hannah!

Hi Hannah. I am pretty new to all this and am finding your website and blog super helpful and inspiring. Thank you! My question is a pretty simple one. I am right at the start of my journey and kicked off by getting myself a pair of breastforms and a bra. I’ve been in my bra for a couple of weeks now as I am working from home, only not wearing it when I’m asleep or either the bra or I are getting washed. I feel more ‘put together’ when I’m in my bra but I’m nowhere near used to it yet – the straps on the shoulder, the clasp on the back, the wires on my chest etc. And the way you are always, always aware of it. Does that start to diminish over time? I just feel that if I wore other stuff like pantyhose or heels, I’d be totally overwhelmed. Hoping someone with some experience can tell me when a bra just becomes part of you. Thanks!

Like strutting across a parking lot in four inch stilettos, crossdressing usually is all about baby steps.  

And yes, most of us ease our way into this.  It took me about thirty years to be completely en femme, from wig to heels and everything in-between.  You can dress as little or as much as you’d like.  Many of us stop at lingerie, some of us don’t.  

It sounds like you wear a bra a lot and you’ll probably always be aware, at least on a small level, that you are wearing a bra (hope you have matching panties!).  And to be honest, I kind of like being aware of wearing something so feminine and pretty.  But if it is uncomfortable in any way, then you may be wearing the wrong bra size.  Most girls (t and cis) wear a bra that is too small and the band is not the proper length.  I would love to wear a 30 inch band but I don’t and there’s no reason to be uncomfortable (or worse) just to wear a size that I would LIKE to be, instead of the size that I am.

When you feel ready, you may want to get a bra fitting.  I had one last year and it was really eye-opening.  If you decide to go this route, call ahead to the lingerie shop (probably avoid the mall stores) to make sure they do bra fittings (especially in the current COVID scenario).  If they do, simply say you are a transwoman and you would like a fitting.  Of course, you may not identify as transgender, but it’s a lot less awkward than asking if they do bra fitting for men. That’s not to say you have to visit completely en femme. Stores that help the transcommunity know that we can present in many different ways and sometimes we present more masculine than feminine.

If you’re looking for new bras (and undies!) to add to your lingerie collection, I recommend:

Lingerie for Girls Like Us

The Breast Form Store

En Femme

Homme Mystere

Glamour Boutique



Allure Lingerie

Glamorous Corset

Third Love

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

4 thoughts on “Ask Hannah!

  1. I’d like to add Lane Bryant to the list of stores. I have had nothing but exceptional service from them, but in terms of bra fitting, but all other aspects of shopping, trying on, purchasing, etc.

    Liked by 1 person

  2. I like to add Torrid they are accepting and carry large sizes. I also find wearing a sports bra (no underwire & wide straps) to keep my breastforms in place and long shorts panties to keep thighpads in place to wear with jeans and longsleeve t-shirt top or as foundation garment for dresses Like Hannah says baby steps but keep stepping.


    Also wear a nice satin nightgown, (Satin sheets, too!) really enhance the experience, along with a SMALL amount of perfume, particularly if you have and use a sent on a regular basis.
    AVOID scents that would remind you of former lovers, mother, sister, ect…
    Scented body powder is a good alternate idea. DONT MIX SCENTS!
    AND do try to remember your dreams!
    I hope you experience A MAJOR exploration of your ‘alternate, former self’.
    The first time I attempted this, I had the most lucid, real, ‘In Living Color’ dream where i was re-acquainted into my former life as a woman. The breast forms merged into my former self, as if they were real breasts….


  4. I asked several cis-women about wearing bras and, like the question, never got to a point where I didn’t notice wearing one. They all said “welcome to the club”. A good bra fitting definitely helps make it mire comfortable but some notice of it never really goes away …. enjoy it! It’s a part of modern womanhood!!


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