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Transgender/Transsexual/Go idea to get caught cross dressed?


Hi, I'm a 21 year old Cross dresser and have been dressing for around 10 or so years now. Last year I told my mum how I enjoyed cross dressing. She was absolutely fine about it much to my surprise. It is currently our secret although I'm sure she has told my dad.

My question is I really want her to see me dressed, in hope that she will be ok with me dressing at home. I have tried asking her but can't buck up the courage, even though she already knows.  

To give you a little inside into how she feels about me cross dressing, she has even washed clothes for me that I have left out by accident.

But I though some advise on the situation would be best, thanks.


First let me congratulate you on making the step to come out to your family at such a young age.

I can understand your desire to be dressed much more often especially when your at home. After all it's your home and you should be able to do what you want (within reason) when your at home. As your mom is aware and either approves or at least tolerates than I don't think she would have a problem, however you will need to have an honest and open discussion with your father and make sure he is not going to be uncomfortable, and set boundaries.  

What I would recommend you do is sit down and have a chat with your mom about what you want to do. And then let her talk to your dad. Depending on the outcome you may not be able to dress at home full time. What you could do is keep it simple at first. Instead of going all out with the skirt, heels, make up, etc the first time just try one piece. Instead of a skirt or dress, try wearing your boy clothes but with girls jeans, or a pair of flats. Ask her if its OK to paint your toe nails, or wear a bit of eye liner, lip gloss, let your hair grow, etc. Just add one piece at a time and try to consider yourself more androgynous. After a while your mom and dad will become more accustom to seeing you in fem attire. Then when you decide to go out all dolled up it won't be such a big deal.

And also let them know you are still their son and always will be. Let them decide on what pronouns to use around you regardless of how you are dressed. After all you already have a girls name. (Danny or Dani). If you get a bit of push back at first then don't make a fuse about it just change back to your boy stuff, but once both know there is no reason to hide it from them.

You didn't mention your sexuality and I don't want to assume either way, however in some situations the dad may consider cross-dressing to be a "sissy" or "gay" behavior and may push back very hard to the point of insulting their sons. We have all herd the phrase "No son of mine...." The reality is being trans has nothing to do with being gay or straight. It's a form of self expression and part of your individuality. The more you suppress it the more distressed you are going to be. You will need to work with your parents to educate them about the difference of what it means to be trans and what it means to be gay or straight.

Another thing I've observed in many of the trans people I know is that when they come out they want to come out to the world. I'm just as guilty as anyone else. I advise you to be cautious. Let your mom decide when and if it's OK to talk to your dad. There may be things going on between them that you are not aware of and she will know better. Over the next few weeks and months if you can dress at home, it may give you a chance to bond with your mother in ways you never thought possible. After all she is an expert at being a girl. Shes been one her whole life and has given birth. Who better to help you with the little things.

Finally as you are now 21, I would suspect you are planning on moving out of your parents home soon. Once you do you will be away from their control. Once you are out you will have much more opportunities to dress, however if they don't know and decide to make an unexpected visit to your new home, how are you going to explain it if you open the door in full fem attire. Or they come over and want to know who the girl is that seems to be living with you. So honesty is always the best policy.

I'm sure i could go on and on with a bit of girl talk and if you would like to communicate more my personal e-mail is

Let me know how things work out.

Cheryl H.  


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Cheryl H


I can answer questions regarding male to female cross dressing and related issues. I will not answer any question dealing with pornography. If you are a minor and are asking adult related questions be prepared for me to either reject the question or tell you to ask an adult. Run on questions and that go on and on with various amounts of unrelated details will likely be rejected. I don't have the attention span to read 14 paragraphs crammed in to one about your high school crush before you get to the point. Fantasy and fetish inspired aka (Too good to be true) situations will likely be rejected. I wasn't born yesterday and I've encountered my share of TG fantasy. I can recognize the themes. Fictionmania exist for a reason. I'm a hetro cross dresser, this means I do not date men! I'm happily married with 2 sons. So don't bother asking me for a date... It's not going to happen and I will reject your question.


I am a life long cross dresser (male to female) and have been presenting in public for the past 10 years. I'm a member of Tri-Ess (Society for the Second Self). I've had the opportunity to get to know 100's of transgender people and have worked though and with those that are new to the transgender community. I have assisted many young and new "girls" when venturing out for the first time and worked with their families to help come to terms with many of the issues related to this life style. I am not a doctor or have any type of degree in this field, but I have cross-dreesed my entire life. Who better to ask a question about transgender issues than a transgender person. I am willing to answer any question I can concerning the Transgender lifestyle however there are some areas I will avoid.

Member of Tri-Ess, and Sigma Epsilon. (Society for the Second Self, Atlanta Chapter.)

No formal "education" but I have 40 years of experience being a cross dresser. Who better to speak with than someone who has been there, done that, and has the t-shirt. I'm willing to lend an open ear "and shoulder" when necessary to who ever has the need.

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