How Does One Go From Crossdresser to Transsexual?

Birth and Rebirth

In June of this year, I published a letter written to me by Anna, along with my response. Her boyfriend, Matt, was a crossdresser and Anna expressed her many questions about the topic. If you’ve got some time, I recommend you read the original post before continuing here. This is a follow-up about Anna and her crossdressing boyfriend, Matt… who turned out to be more than just a crossdresser.

Anna was kind enough to offer me a brief update a few weeks ago. She explained that they’re still together in a loving, committed relationship, and that Matt turned out to be more than just a crossdresser. He’s a transsexual who has decided to transition. A short time after, Matt also contacted me personally to let me know that he has decided to document his journey in a continuing video blog (or vlog) series on YouTube.

Matt’s real name is Todd, information I share with his blessing. Todd is on his way to becoming Tessa, his chosen female name, that will later become her legal name.

I was a bit surprised to learn that Tessa is a transsexual rather than crossdresser. So how does one go from being a crossdresser to transsexual? In Tessa’s own words:

When I referred to myself as a crossdresser I used that as somewhat of a “smoke screen” to hide my real feelings. I figured I wouldn’t have to confront those feelings if I could keep them at bay with something kind of like what I really really want (hope that makes sense).

It makes perfect sense, Tessa. I think it’s safe to say that most of us that occupy the transgender spectrum have tried to convince ourselves of things that we feel might be more acceptable and/or easier to live with. There’s nothing easy about existing as the kind of person that much of society doesn’t understand and often frowns upon. The rationalizations and lies we tell ourselves are a defense mechanism, designed to minimize our feelings of not feeling good or right about ourselves, among other things.

I’ve watched several of Tessa’s videos on YouTube. I encourage you to give them a look, too. The videos are not just trans-talk only, but instead offer an interesting peak into someone’s life in a very personal way. For instance, Tessa is a very talented musician, pursuing a career as such, which is also discussed in the videos.

Transgendered people often struggle with this aspect of their lives for many years before finally discovering who they really are. Todd/Tessa offers a unique look into the thoughts, feelings and life of a transsexual going through the process of transitioning. Just as there is more to life than one’s gender, there is more to these videos than just gender-talk. Although the content might be most meaningful to other transsexuals, there are feelings discussed that many transgendered people experience – crossdresser, t-girl, transsexual, and everything in between.

Tessa’s YouTube Channel: Birth and Rebirth

I’d like to thank Tessa for being brave enough to document her transition process and allowing the world to see. I also send my love and respect to Anna, Tessa’s girlfriend, for sticking by her love, regardless of gender.

Related content: Dear Gabi, I Have So Many Crossdressing Questions…

17 thoughts on “How Does One Go From Crossdresser to Transsexual?”

    1. I’m sure they appreciate your support, Erin. :) Tessa’s journey may not be an easy one, but I’m sure it will be a rewarding one. Following one’s dreams is usually a lot more rewarding than simply choosing to live a lie.

  1. Best wishes to Tessa and her partner – it’s a journey, and one that will be enviably complex and multi-dimensional.

    From my own perspective, I never identified as a crossdresser per se. I went through a period where I was actively crossdressing, but my identity was always transsexual.

    The crossdressing was a stage I had to go through to get to where I am now. I certainly stopped at various points along the way to “smell the flowers”, but moving forward was constant and persistent for me. I needed to transition, and I suspect that Tessa did too – it just took her a while to admit it to herself.

  2. While I would not consider transitioning myself, I support those who choose that path. I think the prospect is a fear that many, if not all, SO’s have when a CD reveals to them. It’s obviously a heavy topic and I won’t go into details. However, I was asked the question at some point in my relationship with my GF. I revealed to her very early on, so I think the question was about the same time (along with the many other questions).

    I too send my best wishes to both Anna and Todd/Tessa.

    Thank you for the topic and for the support that you offered.

  3. Thank you for the very sweet update on us. We won’t pretend that it’s easy all the time, but I know that this is what T needs to do.

  4. Thank you so much for your support and your update. It means a lot to both Anna and I. I will also be formally thanking you in my next video. Thank you sooooo much!

    1. @ Michelle – Thanks for adding your perspective on things. :) It’s very interesting how people usually move through life knowing deep down what is right for them, and making personal discoveries along the way. I admire your constant moving forward toward the place you know you belong in life, and love your “smell the flowers” reference. That’s such an important part in one’s personal growth.

      @ Erin K – It is a concern to many women when they learn their man is a crossdresser. Most people know so little about the subject. That’s why this follow-up is so important. In many ways, it reflects the differences between a crossdresser and transsexual. More important, it places emphasis on the human factor – regardless of gender, this is about living life as we need to, regardless of how popular “who we are” is (whatever that may be) in the collective eyes of society.

      @ Anna – You’re welcome. :) Perhaps the path ahead of you (both) is not an easy one, but more often than not, the best things in life do not come easily. You are both intelligent people who share a deep love for one another. Some people never experience the kind of love and devotion the two of you have found in each other. Regardless of any differences that may exist in your relationship (when compared to the relative “norm”), you’re already well ahead of the game in my opinion. I’m glad you reached out to me this past summer. You have my respect, admiration and best wishes for the future. :)

      @ Tessa – You’re welcome. :) And thank you for being so brave as to share this very personal part of your life with the world. As you’ve discovered, not everyone will be so receptive of what you share, but the haters will pale in numbers compared to those who find your offerings very meaningful and helpful in their own lives. I truly love how you’ve chosen to incorporate other aspects of your life in your videos – that’s so important. I hope you’re able to keep the videos going for a long time. Take a note from Michelle, and keep moving forward in life, even if at times you feel weak under the pressure. Follow your dreams, and be who you are – who you’ve always needed to be. My love and respect to both of you! I wish you much happiness and all the best! :)

  5. I just wanted to say that I totally understand what Tessa was going through by starting out as a crossdresser. I did something similar and when I started to realize that I couldn’t be happy just crossdressing, I actually got scared and purged. It wasn’t till another counselor and some other major events later, that I began to realize and accept myself for the girl I am.

    Tessa, I subscribed to your channel and will keep an eye on it for sure. I am at the beginning of my journey as well….maybe I will start vlogging as well.

    1. Jerica, If you’re over the “being scared and purging” thing, then you really should consider vlogging about your experience. It may be helpful to others and even therapeutic to you. I mention to be certain you’re over your insecurities first and foremost because when you put your life out there in such a public way like that, you will also inevitably attract some negative attention. I get PLENTY of it myself, and I know Tessa is starting to as well. If you’re not rattled easily, give it some serious thought. If/when you do receive negative attention, let that negative energy fuel you, NOT rattle you. ;) Good luck to you either way. :)

  6. My first reaction reading this was fear. Strange. I’m this kind of “weirdo” over 20y for now, I think that in near future I will not advance, but still… at first I was kinda frightened. Maybe there is a reason, to fear myself? As lately Im not only wearing skirts, but looking also for corsets and boots with high heels… It remembers me a battle with myself decade ago, when I found that Im falling in love with the girl who was not my gf…

    1. I can understand your fears, jMo. You really shouldn’t “fear yourself” though. What do you really have to fear? Do you really believe you’re some kind of “weirdo”? We’re ALL weirdo’s in someone’s eyes (regardless of gender or gender expressed). It all depends on the people around you and what they’re like. I’m VERY glad I am NOT like the people around me (in my town).

      We all have moments of discovery in our lives. One should not fear the discovery, but instead be happy it has been discovered. Regardless of how society is and what is “normal” and what is not – wouldn’t you rather truly know who you are? You’ve got one shot at this, my friend. One life. Do not waste it in fears. LIVE your life to the fullest. BE who you are and be proud to be yourself.

      Tessa has chosen to be the person she knows she is meant to be. Her journey may not be the “easy road”, but it will be a much happier life than choosing to live it as a lie instead.

      Everyone has a different journey. Once you learn the path you should walk, by all means, WALK it. There is no guarantee of happiness in life, but I can assure you that if you do not follow your path; if you ignore who you are, you will never be happy with yourself. Life’s rewards are far greater when following your own path rather than the path others would choose for you. :)

  7. Cross Dressing is not a “condition” that leads to being Transsexual just as Cross Dressing does not lead to Sexual Reassignment Surgery either.
    Cross Dressers for various reason feel comfortable in womens cloths and may only do it in the privacy of there homes while others get excitement by going out in public. It goes not mean that the individual is gay or transgender, all though some may be, it is a stereotype to put all cross dressers into that category.
    I myself identified as being a female not through wearing womens cloths but by inner identity.
    A business women can dress in a manly professional way but nobody thinks anything of it, but if a man does it in the privacy of there home there must be something wrong with them. Womens undergarments can be soft, sexy, silky and fit tight against the body; so what is wrong with that? why is it cute when kids do it going up but somehow is wrong as an adult?

    I may have started dressing as a women but that was only because I identified as being a women. As such I had Sexual Reassignment Surgery (M2F) after many years of struggling with this issue back home in Vancouver (Battle Ground) Washington.

    Just because an individual cross dresses does not mean that will lead to the journey I took. The path to discovery has to be made by each individual.


    1. Thanks for sharing a bit of your story and personal insight, Kris. :) You bring up some good points. I think that as society matures, things of this nature will be better understood as part of what makes up the complex array of the human condition that is currently being ignored and/or deemed as “something psychologically wrong”. The transgender community is as varied and diverse as any other loose categorical grouping of people.

  8. Cross dressing is not a “condition’ just as those that dress up (and role play) in civil war uniforms or medieval costumes do not suffer from a “condition”.

    It is society that perceives all of these groups as out of the “norm” even though when not dressed up they lead what most would consider normal and productive lives.

    Even though I am a transgendered individual, unless I was to tell most people I meet they would not even known it. I work and integrate into society without standing out, but if they would find out they suddenly have issues.

    So who has the real problem here, those in society that are unable to deal with those who are considered “different” or those that can deal with all of the different sec’s of society.

    Isn’t this a form of discrimination no different than racial discrimination (because they are different)?

    1. Well said, Kris. :) That’s the whole thing – the “condition” that we (all who fall under the blanket term “transgender”) suffer from is really prejudice, hate, and discrimination (among other things) from others. I often compare it to how white society treated blacks back in the 1950’s. It may as well be the 1950’s when it comes to transgender issues. Not much has changed.

      The up side is that more and more people do seem to be open to differences in others. Times are changing. They’re not changing fast enough and the number of open-minded people still pales in comparison to those who would rather point and laugh at (or flat out cause trouble for) trans folk. It seems so damn pointless to make life difficult for someone simply because they’re different. We’re ALL different from one another.

  9. Gabrielle,
    You’re so right that we are all different. People that make fun of us or cause trouble for us are no different than school yard bully’s we hear so much about in the media recently. Bullying is how these people feel better or superior. They can’t get it in there own lives or homes so taking it out on others who are “different” from them make them feel better about there own “differences” or inadequacies.
    Transgendered and cross dressers are more secure in who they are than those who feel they have to put us down for being different.

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