A Beginners Guide To Crossdressing.

I often answer questions online and get to chat with interesting people in various stages of their life of crossdressing. Some are just starting out, and others have been doing this for years. Some dress sporadically and others all the time.

One thing that comes across very quickly is that some visitors have never talked to anyone about this side of their life. This occasionally contributes to them feeling awkward, or even ashamed. There are some questions they never had the opportunity to either research or ask anyone.

This page will not answer all your questions, but will likely get you thinking a little more broadly, if you’ve never really discussed this with anyone. My Premium Program goes into considerable depth with many of these issues and might be an interesting thing for you to explore if you wish to go more deeply into the subject.

I want to assure you of something. You’re not doing anything wrong or shameful. You are exploring. And exploration really is an adventure. Gaining understanding is a wonderful thing to do. You may find this page helps – https://fionadobson.com/finding-your-place-on-the-gender-spectrum-with-lenni-and-jules/

One recent visitor to the site from Turkey was completely unaware that here in Canada if we wish to crossdress at work we can do so. They were unaware that to be critical of doing so in the workplace would likely lead the company straight into a very expensive lawsuit were they to discriminate in any way. This concept seemed completely foreign to my visitor, while for those of us in the very liberal cities of Canada this is not something the needs to be an enormous issue. I agree, it’s not like this across the board but in some industries and cities trans rights are accepted quite widely. These are hard won rights and the result of many committed activists over the years. While not every country or city is as progressive, there are norms that have shifted in many places in recent years that make gender fluidity and transgender issues much more accessible than they were even a decade ago. So, there is a great deal to learn.

Many of my members ask the question, ‘Why do I crave wearing women’s clothing.’ It’s a great question and one I deal with quite fully here – https://fionadobson.com/why-do-i-crave-wearing-womens-clothing/

In these pages I try not to either impose my views or dictate what is or is not right for any member. I’m certainly not an authority on the subject and like many of my members I find much of it confusing. The world of gender fluidity and crossdressing is changing fast, and so is society. What may seem right today may seem wrong tomorrow. I’ve seen this time and time again with views about the LGBTQ community, and there’s not really much one can do about it. My best advice is to get as informed as possible and come to your own conclusions. See what fits for you.

Many people in this gender queer space feel passionately about what they are doing, can be quite sensitive about peoples opinions, and if they’ve never talked with anyone before can feel quite vulnerable as they start to do so. I’d like to help with that, if I can.

So, keep in mind that all you read here is really just a starting point. You will likely form your own ideas, but I am giving you a few building blocks with which to help you start formulating your own thoughts on the subject. Frankly, people can’t agree on vocabulary for this part of their lives in most cases, so ultimately you have to form your own ideas. I think being very flexible about this is probably a big part of the development of each of us.

One of my greatest concerns is for people who have never talked to others about it. Often I chat with people online who wish to transition, and yet really have very little information about it, and haven’t spoken to a soul on the subject.  When they live in smaller towns, or for other reasons are unable to participate in an LGBTQ community this is not very surprising. However, the support of an LGBTQ community is very important as one starts to navigate transgender issues.

For example, if one knew in one’s heart that they did not feel male, the temptation may be to think surgery the only option. It’s not. Equally, if the only people you have spoken to about this are medical professionals you are missing a vast amount of information which may help make you aware of the options available. I raise this because, to my surprise, I’ve come across so many members and visitors to my site who are completely unaware of some of the alternatives for those of us embracing the feminine side of our nature.

So, in this page you’re going to see what might for some appear obvious pieces of information, laid out in a question and answer format. For those without the benefit of a community to discuss these matters I hope this will prove of value. Please use the comments to add your own views and further build on the information as sensitively and fairly as you reasonably can.

Please remember that these are just my opinions. They may be right or not – or even right today and wrong tomorrow – but either way, they are a good place start to thinking about gender questions and finding your way in a complex subject.  My own solution to the lack of community, for those who are living in areas without an LGBTQ community, is our Elite Whatsapp Group, where you can discuss all aspects of crossdressing and the gender queer lifestyle with like minded friends.

Below I’ve put a series of questions typical to anyone who’s not got much connection with anyone in the LGBTQ community.  I put these to some friends  – Lenni, Jules, and I answered them myself. Lenni is a CIS woman (that’s a natural born woman) and an Alaskan. She’s a lesbian and has lived with her wife for 24 years.  She’s also an active LGBTQ activist. Jules is a crossdresser living about 70% of the time in femme clothes, and has been crossdressing for about 7 years. Try to imagine the four of us seated around a table in a nice café. In France. And you can imagine yourself wearing anything you like!

Now, sit with a coffee and imagine the conversation.


I want to crossdress. Does this mean I’m gay?

                Lenni: No. I suppose I could elaborate… but really ‘no’.

                Jules: I think you’re probably Bi, which is more fun anyway.

               Fiona: Aren’t we all Bi? There are plenty of crossdressers that are only attracted to women. Check out our survey of 2380 members for accurate results.

If I enjoy crossdressing does it mean I should transition and become a woman?

                Lenni: No. Crossdressing is a verb, and something you do. Being a woman is an identity.

                Jules: I think there may be a little more to it than that. You might want to think about what that really means.  I’d talk to some people who’ve already transitioned, if I were you.

                Fiona: You should learn a little about the gender spectrum. You may not need to go to that sort of extreme.

I want to transition, but I can’t because I have a family. What should I do?

                Lenni: Talk to your family. People change – families need to support that.

                Jules: Your family might know anyway, and surprise you.

Fiona: You should explore what seems most appropriate. For some that will be a matter of becoming a little more androgynous rather than rocking the boat for the family. It’s not unheard of for people to enjoy a level of crossdressing discretely, and then as the children grow and move out they get to do it more often. Obviously if you have a burning need to transition this is not going to be the right solution for you. But figuring out what is appropriate for you, and then figuring out just how much you need to share is inevitable. It may be that you will choose to go further at some point, but finding a comfortable place on the gender spectrum and making it work with the way your life is set up is a good idea.

I can’t dress fulltime, and I feel guilty when I do. What can I do?

                Lenni: There’s nothing to feel guilty about. You might ask yourself why you feel guilty.

                Jules: I found some of Fiona’s hypnosis files really helped me with this.

                Fiona: For years you’ve been told that what you are doing is ‘wrong’. And yet it probably feels wonderful when you dress. This is going to set up a conflict in your mind.  It’s not surprising you feel guilty. You can overcome it by learning more about gender issues, to understand it.  That, and hypnosis, are the two most powerful tools at your disposal.

Does crossdressing mean I have to be submissive?

               Lenni: No. Being a woman doesn’t make you submissive either. Have you met Mistress Meg?

               Jules: I certainly don’t always feel submissive even at my most femme. Plenty of people do, even taking it to a sissy fetish. I find sometimes I am a bit submissive but generally I am more ‘alpha’.

Fiona: Some people love the idea of others taking control. It’s not unusual for that to be part of crossdressing. I think as one becomes more developed in it you’ll find that there are times you think in a more sensitive manner, and it can be easy to mistake this for a submissive nature. However, as you get to know the gurl inside you it may be that you find she has many things about her that are different from the masculine version of yourself.

I crossdress and then feel awful about it and throw away all the clothes I’ve bought. Why?

                Lenni: I have no idea.

                Jules: When I first started crossdressing I went through those cycles. It wasn’t until I really accepted this as part of myself that it stopped.

Fiona: This is attached to the idea of shame. Sometimes it’s because you fear being discovered. The safest thing is to dispose of the clothes. The trouble is, you’ll keep doing it, because it’s a part of who you are. As a result you start putting a collection of clothes together again, and so the cycle repeats. It’s likely to continue until you learn a lot more about accepting yourself and stop denying this side of your personality. That doesn’t mean you have to go full time CD, but you will need to accommodate the gurl inside you. That means being organised.

When I crossdress I want to have sex with men, but I know I am straight. Why do I feel like this?

                Lenni: Everybody’s sexuality is different. I don’t see a problem here.

                Jules: I dress most of the time now, and you’ll find it shifts. It’s still partly a sex thing, but that’s really a small part of it as you embrace it. It’s much deeper now. It’s my identity.

Fiona: If you only dress now and then, it’s likely that you are so excited and the only other time you’re that excited is when you’re sexually turned on. So, the link forms there. Then, there’s that part of all of us that wonders about sex with men rather than women. In this state it’s very easy to find the idea attractive. Personally, I know I am bi. But I think one could have these feelings, and not really even be bi. Many people don’t act on these feelings, because it’s accompanied by so much shame. You’ll need to drop that before you want to start experimenting, otherwise you just complicate the sense of guilt and shame. It’s great to experiment if you do so safely and you may find it wonderful, but best to do it once you’ve really accepted this side of you. My Premium Program is really good to help with this.

I’m afraid to get into a relationship because the person may learn I crossdress and then dump me. What should I do?

                Lenni: Tell them right away you crossdress and they may find it super hot. I do.

                Jules: When I told my girlfriend I love to crossdress she loved it. She’d been waiting for years for someone to come along who was this comfortable with themselves.

Fiona: You can’t put your life on hold. Learn about the issue and then move forward in confidence. Be sensitive.  I’ve written extensively about how one talks to a partner. It’s a matter of being sensitive to her needs, and that means expressing yourself in a manner that she’s likely to find comfortable. I’m pleased to say the Premium Program helps understand how to find, and then talk with people interested in crossdressers. The great thing about this is that once you do connect, you will be the hottest thing they’ve ever experienced. Crossdressers who are able to express themselves confidently are few and far between. That makes you a very hot commodity.

Please use the comments to ask further questions.  I’m very happy to answer what I can.  You can also join my Basic Program at no cost using the form below. The program will keep you on track and help you understand a little more about this wonderful side of your personality. Keep in mind that the right answer for some of us is not right for others. You’ll find your way.


Join me as a Good Gurl today!

13 Replies to “A Beginners Guide To Crossdressing.”

  1. Canada is a wonderful country, and for me, the cosmopolitan the better. It’s fun to go up there and live upscale. I mean, my clothes.. which I love.. my makeup.. the perfume. I just love looking like the confident businesswoman. I’m very much into women. But, I’m into powerful, confident women.. like lawyers, real estate brokers, etc.

  2. This past couple of years as I have learned about my self and the beauty I posses when I cross dress. At first it left me with many questions as to if this is the right choice for me. Now, learning from Fiona has empowered me to the extent to where I am not ashamed of myself for cross dressing. Transforming myself into this beautiful woman has come out gracefully which has always been inside me. I have learned to enjoy dressing as a woman and feel that confidence I gained from learning about my needs as a human being; ie. love, emotion, desire, and solid gurl strength. I have the support of my beautiful wife and her strength, strengthens me. Kisses Fiona and thank you for your beginners guide.

  3. Good once again Fiona, So glad to be back with you. It has been a while with things at home. Still growing with knowledge and needs, giggles. Hope this message finds you well, am thrilled to see you expand your services. Love you, tvlace

  4. Learning to understand why l feel the way I do has become much easier because of you Fiona. I was ashamed for a long time but am gradually getting over it. Embracing Sharri is becoming easier all the time. Am thinking I want to be her full time….thank you Fiona
    Luv Sharri

  5. When I go from male to female, my whole personality changes too. As a male I am quite reserved and even borderline shy, but as a girl I am just the opposite and want to be the center of attention. Anyone else like this?

  6. I’ve found that faced with crossdressing, women fall into two camps: those who are horrified by the idea and those who are turned on by it. The trick is to work out which is which before you “come out”.

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