Transgender/Transsexual/Cross Dressing


QUESTION: I am a 30 year old divorcee living in Australia. A year ago my sister and her husband were killed in a car crash and I assumed the sole custody of my nephew who is now 12 years old.

We got on very well and shared many hobbies and interests. One thing I noticed almost immediately though was that he was curious about the clothes I wore. He would love to sit beside me as I watched fashion shows and comment on the dresses some of the models wore. One of the things he asked me most about was how it felt like for me to wear a skirt. He seemed fascinated with the idea of wearing a garment with no partition between the legs. One day I simply asked him if he would like to try on a dress just for fun. I saw some hesitation in him but he agreed. So I gave him a simple knee length dress to wear which I had bought just for him. He initially wore it over his shorts but I managed to convince him to remove them and simply wear it over his underwear. He loved the dress and spent the entire day twirling and walking as if he was on the ramp and enjoyed wearing it.  

Ever since that day he has loved wearing dresses and skirts and other female clothing that I bought for him. Usually he would just wear his female clothing inside the house and would always change into his male clothes before going outside. One day after a lot of persuasion I managed to get him to visit a dress store wearing female clothes. I dressed him in a short skirt and top with just some basic make up, a little lip gloss and eye shadow. He also agreed to wear a pair of panties instead of his usual male underwear and moderately high heels. He was very nervous at first as he stepped out for the first time but when he realized that no one was staring at him he grew more comfortable in his female attire. In the shop one of the assistants even remarked that Ďsheí looked beautiful. We managed to buy a generous collection of skirts and dresses and tops that day and even some panties and his first bra.

After that excursion he has dressed almost continuously as a girl after school hours. We even chose a female name for him, Jane that is similar to his first name Jack. Recently I had to attend a wedding of a friend and Jane wanted to come dressed as girl. I was a bit apprehensive but seeing Janeís enthusiasm I agreed to let her wear a dress to the wedding. She chose a beautiful elegant dress and I was surprised at how feminine she looked. She was also well mannered and polite and absolutely no one suspected that she wasnít really a girl. Even her voice passed as that of a girl as she hasnít gone through puberty yet. From that day onwards I have begun to see her as a girl. I call her Jane and she is in female clothes almost the entire time that she isnít in school.

I am worried about her future though. She will soon begin puberty and her voice will start to break and she will develop a manly figure. When I talked to her about this she was horrified and pleaded with me to help her stop it. I am thinking of taking her to a doctor to evaluate her and decide if she should take puberty blockers or not. I want to know though is this desire to crossdress something that is temporary? Is it just a passing phase that will go away as she gets older? She not only wants to crossdress but wants to become a girl. She says that she canít imagine her voice breaking and developing a bread or a male musculature. I have heard her say repeatedly many times whenever she is wearing a bra that she wished she had real breasts instead of having to wear breast forms. Does her behavior indicate transgenderism or just the desire to crossdress?

ANSWER: Alice.

First I want to apologize for not getting back to you sooner. Because of the nature of this topic my e-mail filter will sometimes throw these into my junk folder and I don't catch it.... So again I'm sorry for the delay. Also I want to apologize for the length of this reply... You gave me so much info I really needed time to digest it take the time to cover each aspect...What I would prefer to do is sit down with you over a cup of coffee to just talk and answer your questions one at a time. However your in Australia and I'm in the U.S. so that is not likely and this is the best we can do...At the bottom I'll include my e-mail as I would like to continue this further if thats OK with you.

I will use female pronouns when referring to "Jane" as that is what you did.  

In your last sentence you asked (Does her behavior indicate transgenderism or just the desire to crossdress?), actually she is both. A crossdresser by definition is a transgender person, however she may or may not be a transsexual. I think the question you meant to ask was (Does her behavior indicate she is a transsexual or just has the desire to crossdress?) This is an important distinction as Transgender is a umbrella term covering the entire transgender spectrum. Transgender people range from Under Dressers (those who wear female undergarments under their male attire) to crossdressers (dress as women from time to time) to transsexuals who complete the transition and live full time in opposite gender role from their birth gender.

So is Jane a transsexual?.... I don't know... There are many questions you need to ask her and she needs to discover the answer to herself. Based on the behaviors and her desire to have breast, not grow a beard, etc seems to push toward her being transsexual, but that would be between you, her and a psychologist to figure out.

The transgender spectrum has many sub-categories but it is not fluid. Although the boundaries between categories can be blurry and it seems a person is progressing along it, that is really not the case  Someone does not start out as a crossdresser and then decide to be become a transsexual. Crossdressing is not a gateway leading to other things. If it was there would be a lot more guys out there becoming women just because their girlfriends put them in panties or gave them a make over. A transsexual is a transsexual and has always been one but a crossdresser is simply a crossdresser. The end game for each is different. For a crossdresser the act of dressing in female clothing is an end in and of itself. Think of it as a form of expression just as a musician has to make music and a painter has to paint, a crossdresser has to crossdress. However for a transsexual, the act of crossdressing is the means to an end and that end is to appear to be female and make the body match the mind. So it's a necessity not a goal. When you, Jane, and a psychologist begin talking and her emotions and feelings start to come out she will then let you know what direction she wants her life to go in and what steps you will have to take.    

Concerning your position I want to applaud your courage and openness to allow Jane to explore this side of her personality. For someone who is helping a transgender child "blossom" takes a great deal of courage, patience, time and understanding. Personally you will have several challenges ahead and many questions. Many of which you will need to deal with yourself as you are going to catch some heat and you need to be prepared emotionally to deal with it. You are not only going to have to defend Jane's actions but yours as well... It's unfortunate but the world can be cruel and there are going to be those that see what you are doing as a perversion and some my see it as child abuse. They may accuse you of influencing and encouraging this behavior. As you are divorced I assume there is not a male presence in the house. Some may say things like "If there was a man in the house this wouldn't happen" or accuse you of being a "man hater", etc. You need to get your personal emotional armor on and be ready when these individuals begin to attack you, and they will sooner or later. The important thing for you to understand is you did nothing wrong and you did not start this. It was likely Jane's interest to do this existed well before she came to live with you. Remember she asked you what it was like to wear a dress, not the other way around.   

Regarding Jane's development children develop different interest when as they grow up. Some times they go through a phase where they are interested in a certain TV show or video game, etc. Developing an interest in clothing, makeup, fashion at this age is no different from developing an interest in sports or music regardless if the child is male or female. However when a child begins to express an interest in crossing gender lines, it's rarely a phase. likely Jane has been dealing with the desires and interest for years and has only recently acted on them. Every transgender person I've ever met (myself included) knew there was something different about them when they were very young, usually around the age of 5-6. This is important as the public in general sees transsexuals as a sexual perversion of some kind and has all sort of hang ups. Ask yourself how many 5 year old children really understand what sex is? Personally I don't believe transgender behavior is a sexual behavior but rather a psychological behavior and is simply a normal part of the child's development and discovering who they are. I think what Jane is going through now would happen sooner or later regardless of her circumstances. The great thing is she is young. Dealing with these issues gets more and more difficult as the person grows older. One of the questions I would ask her is when did she start feeling like a girl or wanted to know what it was like to wear a dress. If she says it's been a long time and she says around the age of 5, than she is not lying and this is not a phase. If you and her don't deal with it now she will the rest of her life. I should also mention the suicide rate among transgender teens is extremely high as they find it hard to fit in. Having a support structure in place and some understanding friends is going to be very important. I would recommend you find a transgender youth support group in your area ASAP.  

Considering how she opened up to you and her reluctance at first is very typical behavior for a transgender person. Her reluctance when first trying on a skirt and then to take off her shorts and go with just underwear, then to go outside is normal for a transgender person. I believe she really wants to do all these things but is afraid of being made fun off, even by you, and doesn't want to push the boundaries to fast as she does not want to do anything that will seem strange or offend you. Also she does not want to be embarrassed by others she knows. She has to know she can trust you with anything and everything. I feel that trust has been established but you need to continually reinforce it. As she becomes more comfortable in the female role she may begin to feel she is Jane more and more, and start to push Jack into the background. Regardless of how much "Jane" there is physically she is still a male. You are her support structure as well as being an expert in being a girl, as you have been one your entire life, but she is having to take a crash course. As such you need to be there to advise her. She will likely make some social, and fashion faux pas and you will need to advise and correct her. There may be social situations where she will need to revert to her male appearance and behaviors. When that happens she needs to understand why before hand not when the situation arises. If not you might get some push back. If you haven't already NOW is the time for the two of you to have a conversation of when it is appropriate to be Jane and when she will need to be Jack. She needs to understand when and where it's safe to be Jane and what the rules are. If you wait for some big event and she is expecting to go as Jane, like to the weeding, but has to go as Jack you may find yourself in an argument with a "young lady" that refuses to take off the dress and make up 10 minutes before its time to walk out the door.

Based on what you describe Jane is going through a blossoming period. For adult crossdressers we sometimes refer to this as a second puberty when they come out. It's not a physical puberty but an emotional puberty as all the things we did not have access to growing up is suddenly made available. We become like kids in a candy store and everything is a new and exciting experience. As Jane becomes more comfortable in her female persona her confidence will rise and the initial excitement will fade. However what was exciting at first for her may become normal and just feels right. From what you are telling me with her dressing at home this is solid evidence this is happening and it's not just a phase. What I would advise is you make an appointment with a psychologist who has experience with transgender children. A web search should help you or a call to a transgender support group should point you in the right direction.

Another thing I want to briefly mention is sexual orientation. Just because Jane is expressing an interest in being a girl, does not mean she is interested or will ever become interested in dating boys. This is a confusing factor for those outside the trans community as ones chosen gender and orientation do not always align. Jane could easily live as a girl her whole life and never have a desire to date boys and prefer to live as a "lesbian". Please understand this is not that unusual. It's possible she may be interested in dating boys or she could be bi-sexual. What ever her orientation don't try to influence or change her to what you feel is right. Only she knows what is right for her. This will be one less thing she has to deal with.

If the psychologist determines she is transsexual and has not started puberty, she can be prescribed hormone blockers that will delay the onset of puberty. When she is about 12 or 13, she can be given female hormones such as estrogen and few other things that will cause her to begin a female puberty. As she is young the effects are pretty much reversible. If she decides to stop taking the pills her body will begin to revert back to male. However as she is so young there may be some effects that are not reversible and she may become sterile. A doctor that specializes in this will be able to give you more info.

Also I would highly recommend if you do plan to put her on hormones that you have her monitored regularly by a doctor and get the pills through normal and legal means. There are some transsexuals who get their pills through the black market or from doctors who do not have your best interest at hart and only want the money to write the prescription. If her doses are wrong it could lead to many other health issues. Blood clots are not uncommon for male to female transsexuals and can lead to other health issues such as heart attacks, numbness in limbs, difficulty breathing, stroke and death, depending on where the clot gets stuck. Being young is an advantage for her.

If you and Jane decide to take the big step and she becomes a girl full time arrangements will have to be made for her at school regarding the restrooms, gym, etc. She maybe able to pass as a boy for a while but the hormones will start to fill her out and soon she wont be able to hide the fact she has breast. She may have to switch schools to avoid teasing and possible bullying as those that knew her as Jack may take offence when she becomes Jane. Some schools are more open than others so finding the right school will be important step.

Because she has not experienced male puberty yet her female puberty will be pretty much like any other girl. She will develop breast, hips, etc. Her penis and testicles will not grow much and should stay pretty much the same size they are now. This will make them easier to hide if necessary. By the time she graduates form High School she should look like any other girl at that age. The only thing that might be a problem is breast development. Most transsexuals do not develop fully and require breast implants to fully round out and give a proper shape to the breast. However most have completed male puberty. It's likely Jane may develop one cup size smaller when compared to the women in her family. Then again being so young, she may not have any problems at all.

When she is 18 she can legally have sexual reassignment surgery. However that is a choice she will have to make then. Not all transsexuals have their genitals changed. These individuals are known as pre-op if they plan to take that step later, or non-op if they don't plan to have the surgery at all. For some the surgery is not important for others it is. She will have to decide and no one should force her into any decision.  

I would highly recommend you read up on the topic of transgender youth. A young lady that is going through everything Jane is going through has a great web site. If you have not heard of Jazz Jennings, you really should introduce Jane to this site.

There is also a great write up on her from CNN

As I said at the start of this long reply I would like to continue this, my email is If there is any thing else I can do for you please let me know.

Cheryl H.

---------- FOLLOW-UP ----------

QUESTION: I have sent an email to you but haven't received a reply so I guess there might be some technical error. I asked Jane about when she experienced a desire to crossdress. She says that she was always fascinated with female clothing and was curious to know what it felt like to wear skirts and dresses with make-up and high heels. She says she would wear her motherís clothes when she was alone and would imagine herself as a girl. She is very comfortable in female clothing and is quite adept at managing her skirts and dresses. I took her to a psychologist a few days back who couldn't believe at first that Jane wasn't a biological girl. He has called her back for an evaluation but he privately told me that he doesnít think that there should be a problem in giving her the go ahead to take puberty blockers. I havenít yet had the birds and bees talk with Jane but she is curious about female genitals. The other day when we were at the beach she asked me if I could pull down my swimsuit bottoms to show her how female genitalia looked like. I didnít agree to that but I wonder if you have any idea of how I can satisfy her curiosity.


I just discovered this morning my e-mail has been hijacked and is sending random spam. My password was changed without my knowledge. I've taken means to correct this but it does explain why I've been having difficulty getting e-mail lately. I'm likely going to have to open a new account.

I did find the e-mail you sent and again it was in my junk folder... However I should have seen it on my Iphone when it came through but the highjack apparently prevented that. So once again please accept my apology.

Concerning your situation with Jane, I would say at her age it's time for the birds and bees discussion. With her interest in changing gender she definitely needs to know why women have babies and men don't. She needs to understand why she will never be able to reproduce if she goes through with this. However when she becomes an adult adoption is not out of the question. Like I said previously, transgenderism is not sexual but psychological. As Jane does not yet know what sex is this is definitely not a sexual hang up or perversion but just the way she is wired. I was 90% positive the way you worded your original question the psychologist would say she is a prime candidate to be transsexual and that looks like what has happened. It seems her answers to the questions you asked her are right on target for her to be trans.

As far as how to show her what the female genitals look like, this might be a discussion between you and the psychologist on how best to proceed. I agree you can't show her your body. She needs to know why that is inappropriate. Not bad but just inappropriate. Medical photos (non porn) of a woman's body might be the best choice or a biology book of some kind with illustrations may work. If Jane gets on line and starts "googling" who knows what she is going to find. Concerning the hormones, get her on them ASAP as puberty in boys usually starts between the ages of 12 to 13 and definitely before the age of 14.

Again I applaud your courage and generosity to help a fellow sister in this time. She is very fortunate to have you in her life. It's going to be a difficult road for her and she is going to have many, many questions. Other than myself, I don't know if you have had any contact with the transgender community. It's important for Jane to know that she is not alone in this and there are many men and boys who want to be girls. The recent coming out of Caitlyn Jenner (formally Bruce Jenner) for example. What you will find when you meet other trans people is we are very open and welcoming to others. Likely the friendliest and most honest people you will ever meet. We welcome everyone and we look out for each other. We have to as no one else will. I think the main reason for this is we just want to be accepted for who we are and how we want to live our lives. The trans community has been rejected by every other social group. Even among the larger LGBTQ we are shunned as being "traitors", even gay men and women will still make jokes about trans people. It's often said the "T" is silent as a result.

Please let me know how things work out with Jane, and I would love to continue this discussion. Until I get my e-mail situation sorted out, please feel free to communicate here. If you would prefer others not to read this, you can send me a new message in a new thread but mark it private. Then it's just you and me. I'll let you know when I have a new e-mail account set up.

Thanks again.  

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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