Ask Hannah!

I am a male who has been crossdressing in private for many years. I have regularly questioned myself about why I do it and always come back to the fact that I enjoy it and feel more alive and comfortable when I do. My partner does not want any involvement in that part of my life but I can’t give it up. However, as time goes by when I am dressed I am becoming more attracted to other men. I have had some sexual experiences with T-girls but wonder if I should go all the way with a guy while dressed to help understand what is really in my head and what I should do in the future. Any advise you have would be much appreciated.

If you’re asking if I think you should pursue sex outside of the relationship you have with your partner, then no, I do not think you should go all the way or do anything with a guy or with anyone else, regardless of how you are dressed or of their gender.

No matter your gender identity or your sexual identity, I do not think you should be intimate with anyone besides your partner. Ever. At all.

If you feel the need to be physical with anyone besides your partner, for whatever reason, the two of you need to have a very serious conversation about this perceived need.

Aaaand as long as I am on my soapbox (and on the subject) I don’t think that clothes “activate” one’s attraction to another gender. If you are attracted to men when you are dressed up, then you are probably attracted to men when you’re not dressed up.

Also, I don’t think having sex with a t-girl or being attracted to a t-girl means you’re gay. T-girls are girls, remember? It’s not gay to be sexually attracted to a girl, unless you are a girl, I suppose.

Some crossdressers tell me they are straight when they are presenting as a man, but identify as bisexual when they are dressed up. The reality is that their sexuality didn’t change when they changed their clothes. In my opinion they are feeling a little less inhibited when they are en femme compared to when they are dressed in boy clothes which makes someone feel a little more… open to something.

If crossdressing arouses you, it’s not surprising you want to have sex when dressed. When we are aroused we often are open to things that we didn’t think we would be. Again, we are less inhibited and our… decisions are being made by our desire, not our brain.

Love, Hannah

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5 thoughts on “Ask Hannah!

  1. Hi Hannah,

    I would like to add one additional item. I think sometimes we are interested in men when we are dressed as a woman but are not in male mode simply because being desired by a man is validating to us as a woman. It may not actually have anything to do with sexual orientation. We may not walk down the street noticing attractive guys, we may just be looking for someone to make us feel more female.

    I think that no matter how hard we fight it or disagree with it we are all susceptible to our learned ideas about gender roles. And in those roles beautiful woman are desired by men.

    Of course I could be wrong. I have not read any research supporting my opinion just a hunch.


    Liked by 2 people

  2. JODI and HANNAH,

    My personal observation is we want to be accepted in our femme presentation and I have found it very rewarding and heart warming and self satisfying to be accepted by a clutch of CIS women as just one of the girls. Being admired is always rewarding however being “Hit on by a male” can be scary and perhaps terrifying. I have it happen more than once, fortunately I was able to navigate out of the situations.
    Marie Anne Greene


  3. Thank you for your response. I believe that when you are married you make a promise to your spouse and God (whom ever your God is). By cheating on them your hurting them. IMHO.


  4. I have no attraction to men … except when crossdressing i often wonder what it would be like to be with one! I m in therapy exploring what it all means. I dont think a person is gay or bisexual if they are attracted to the opposite sex while in a different gender presentation although they could b


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