Hannah Asks…

One of the common phrases people use to find my website is “crossdresser guilt”.  I don’t write a lot about feeling guilty about this side of me.  I have known who I am and what I like to wear for a very long time.  I’ve accepted this, and I have embraced it.

Who we are is a multitude of emotions and feelings.  Happiness, embarrassment, fear, confusion… the list goes on.  But guilt is not something I have really felt.  But based on the emails I get, the comments, and obviously the Google searches, many of us do.

So, for those who feel guilty about this side of you, I would love to know why.  Is it guilt because you may be hiding this side of you to your significant other?  Is it guilt because you’ve been told this side of you is a sin?

Let me know by commenting!

Love, Hannah


6 thoughts on “Hannah Asks…

  1. Well, I’m not in hiding from my lovely wife and not being religious, I don’t consider who I am to be sinful 🙂

    But, I do feel guilty from time to time. It’s rare I get that from “you should be normal” – whatever normal is 😉 – as, like you, I made my peace with being trans a long time ago.

    What it is is the inconvenience or impact it has on family life. I don’t dress at home, but twice a month at a social and support group. That means those nights my partner holds the fort at home and there are rare times when her invitation for a girl’s night out clash.

    There’s spending money on a second wardrobe or my trimmed eyebrows and occasionally smooth pins that cause upset. Really, It’s the latter that makes me feel guilty: upsetting my dear wife. Realistically I can’t be ‘just a bloke’, I need to express all sides of me, yet I feel if this was not part of me, there wouldn’t be this friction. Ironically, my wife doesn’t like macho types, so perhaps if I was more blokey, we’d not be together and that would be awful.

    Great question BTW

    Liked by 1 person

  2. I would offer a change in semantic from ‘guilt’ to ‘shame’, at least on my own behalf.
    I have endured a relatively long lifetime dealing with a matter termed by Dr. John Bradshaw as ‘Toxic Shame’. No matter what I did in my life, I always saddled with feelings of guilt and most notably SHAME as an un-warrented mental payoff, even for sincere, honest labors. The ultimate dividend of this un deserved SHAME is a many layered depression and a dysfunctional, unproductive life. In real terms, I have done very few things in my life that were truly SHAMEFUL.
    Bradshaw, discusses his own discovery and examination of ‘Toxic Shame’, (he mentioned how shameful he felt about how perhaps the MINISTER whilst visiting the home, could perhaps MAYBE hear him ‘make a tinkle sound whilst urinating’ and subsequently judge him negatively) and how the systematic shaming of child by parent, teacher, religious leader, government, corporate entities ect.. is really a flawed tool to control child behavior.
    I have read several of his books, (“Healing the Shame That Binds You” et.al.) and am quite ‘WOKE’- as the youngsters now say.
    I no longer ‘play’ the guilt/shame game, either on the ‘giving’ or ‘receiving’ end.
    The fact that I (or you) crossdress is NOT an issue to feel guilty or shamed over. This behavior is a quintessential element to our being, and is part of our own individual unique placement on the spectrum of human gender. This matter is immutable, so I suggest you simply live your life as you see fit. Repression of this urge only makes matters more dire- …
    Today (Saturday, Feb 29) my wife and I (dressed as Velma) went out to have lunch in a small somewhat conservative town in North Carolina. Our experience was quiet and uneventful, (as usual) in spite of a mans query at the Dollar Store–“You mean everything here is just a dollar?”. I politely answered, “yes”, and he and I went on about our individual business.

    If you feel undeservedly guilty or shamed over this or any such matters, you too need to understand this behavior system has its origin in your childhood, it is NOT because you crossdress. You need find a solution to your ‘guilt/shame trip’ brought to you on behalf of your societies’ misguided system of rearing/managing children, and adults.


  3. Bosom Buddies, Funky Cold Madena and other pop culture references were cute to most people but odd and laughed at by the public. There are many more nudges and (unintentional I’m sure), subtle brainwashing productions like these that gave the message: This is SO weird! Can you believe people live like this? Man should wear man’s clothes. Woman should wear woman’s clothes. How hard is that to understand?! These people are crazy! First guilt. Being Catholic in a little farm town didn’t help. I was torn because at 9 wearing my sister’s skating outfit felt so right and normal. She didn’t know. I stopped as a teenager out of guilt because i started liking guys too. This was too much going in the wrong direction according to the white picket fence American Dream. I was already a bit of a an outsider because i was quiet when all the guys at a party were talking sports. I had to be somewhat normal if I could help it just to have friends. So i got a girlfriend at 18 and stopped this delusional behavior for about 24 years! It was awful. I conducted myself in society fine. Had friends who dressed only as guys (BORING) and only dated girls. They also liked sports and fighting. Is there anything more boring than mens’ clothes? I even got married to a woman, bought a house and had a kid. I couldn’t take the denial anymore. Something broke. In 2018-19 moved out, divorced, started dating guys and went out in public en femme. As far as dressing; It just hit me one day that it didn’t make sense to feel bad about bringing beauty into the world. Who doesn’t love a flower?! My daughter who is little found one of my wigs 2 weeks ago. She doesn’t know exactly what I do yet. Now i am worried one day when she does kids at school will tease her. New guilt.


  4. It’s threefold:

    1. Something that is different about you and me is that I don’t feel that Alicia has a different persona as my male self… I’m a die hard weather nerd in either gender… I’m a die hard craft beer fan in either gender… and… um… I am head over (high) heels for my wife in either gender. In struggle with this to be honest… I want to love on my wife as much as Alicia as I do as my male self. It feels hurtful to see her hesitant to do so, because I feel like it’s just me… so there is guilt there.

    2. You also hit the nail on the head about it and sin… I am an evangelical Christian… I love Christ and believe he is my savior and that his death and resurrection paid for my sins… but so many add all of this crap to it… usually a bunch of one-liners from the Old Testament (while ignoring others). I see them doing more to hurt the kingdom than help it. I guess as someone who is (publicly anyways) Cis-het-White-male, I have a real obligation to try to change this.

    3. And finally, even if I’m not “you’re man” or “a believer,” others have a hard time accepting this… and so that leads me to feel like I’m wrong. I’ve lost friends over coming out… seriously. Others have said harsh things to me. My family would probably disown me… which is becoming more and more okay with me TBH. I’d rather be my true self with a smaller number of people by my side than be a fraud who is universally loved.


  5. Yes, there has been guilt for a long time. I’ve always felt that wearing girl’s clothes was very inappropriate, definitely when it aroused me. This was a dark side of me that I had to hide until I would die. Last year, there was a tipping point, and I don’t know exactly what caused it, but I started to look at it from a different perspective. I knew what I wanted, and that was having an occasional total makeover. I still felt guilty, since my wife did not know, and I was afraid of her reaction…
    But for her it was not a “big deal”. When she saw my tears, she feared that it was much more serious (like cheating on her). She was okay with it if I would continue this journey, although she does not want (yet) to be confronted with it. I understand that.
    I only felt guilty towards her, not towards children or family or friends. Guilt has vanished mostly, and I am happy for that. Now I consider this as interesting aspect of me.
    The little guilt that is still here, is that I’m spending quite some money lately on services, clothing, makeup and accessories (wig, prostheses…), and my wife does not know the details (she does not want to know them actually).
    Hannah, I’ve read your blog from the start. I’m very glad it exists, since it has helped me a lot to accept who I am. Thanks!


  6. I agree that it is more shame than guilt. I do not believe that I am doing anything morally “wrong.” For me, it is the necessity of secrecy that triggers shame — couple that with my wife’s continued refusal to accept this part of me — and I end up feeling “less than” because I feel like I burden her (and my life) with this lifelong longing to be a woman and dress in feminine clothes. I do believe that many people in my life, like she does, would judge me harshly if they knew my secret. Keeping the secret keeps me feeling shameful. Nancy


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