Dear Gabi, My Crossdressing Honey Feels Like a Freak

Dear Gabi,

Three years ago, I hooked up with my (yes, this is a cliche) High School SWEETHEART. We’re both in our late 40’s… divorced… kids… yawn yawn blah blah. He came out to me about 9 months after we re-initiated our relationship. He’s a cross dresser. Her name is Kelly. I am all for it. No problem. Be what makes you happy. Life is short. But it doesn’t always make him/her happy. He thinks he’s a freak. His ex never knew this about him. He’s known his whole life. What can I do to convince him that all is good… I love “them” the way they are. It’s now been 3 years. I moved from California to Michigan during an American financial crisis for “f” sake. I love him. Have since I was 14. I come from the land of fruits and nuts. I refuse to judge anyone… EVER!! Living in this closed minded world I have found Michigan to be is not an easy transition, so I understand his trepidation. HELP!! The people here have stunted his mental growth! He fights with me. When he’s Kelly… all is good until something (ie the door bell rings) sets him off. He becomes paranoid and rips away Kelly faster than you can sneeze. Then proceeds to be depressed for days! I have his back! He’s not alone anymore. What more can I do??



Gabrielle HermosaDear Lori,

I understand you’re “crossdressing honey’s” troubles all too well. The debilitating insecurity and overwhelming fear of being “discovered” is something I struggled with for most of my life. I, too, once felt like a “freak” for being a crossdresser – but not anymore.

The feeling of being wrong in who I am, and intense fear of being discovered, was rooted in the very false premise that it is “wrong” to be that which is not widely understood or accepted by society on the whole. For the most part, we all grow up “learning” (the fallacy) that it is some kind of mental illness or perversion for a man to exhibit feminine traits. It lead to a strong sense of insecurity and self-hatred tied to this aspect of my life.

It took many years, but I finally came to my senses and realized that the real problem was not in me, but rather with how mainstream society views and treats differences in people. The root of my own misconceptions about myself (and that which makes life difficult for many people within the wide transgender spectrum) is the social taboo element. Remove the social taboo and terrible stigma associated, and I’m certain that about 99% of all “paranoid” crossdressers would suddenly become very NOT paranoid and begin experiencing a much more relaxed and gratifying experience in life.

I must express my respect and admiration for your take on things. Whether or not you fully understand how crossdressing works in Kelly, it is clear that you love her (and him) for being the good person she is – without judging or looking negatively upon personal traits that are not in line with what many consider to be “normal” (note the quotes). If only more people were willing to accept and respect people for who they are, the world would be a MUCH happier place. But you know the deal – misery just loves company!

Find the underlying cause
Question Kelly’s feeling of being a “freak”. Does she truly think of herself as a freak? Does she wish she was not a “freak”? If there was a magic pill that could remove the trans aspect from her array of personal traits forever, would she take it? Even if this has been discussed in depth already, get into it with her again. Be sure to ask these specific questions and take the time to explore all of associated feelings in depth.

After discussing the feeling of being a “freak”, begin exploring the reasoning behind it. Does Kelly feel like a freak simply for being trans, or is it more a matter of “fear of what others may think” if they found out? In my experience, it usually turns out to be the latter.

One good way to explore this is by discussing an alternate reality in which society has no problems with the vast differences in others. The argument that such a society “will never exist in our lifetime” is not relevant in this context. It is about exploring existence, albeit a fictional one, in a world that does NOT look down upon or treat people poorly for simply being different than the majority. The purpose of the exercise is to reveal the underlying thoughts and emotions associated with being trans without the negative social stigma coming into play.

The feeling of being a “freak” is often tied directly to the fear of what others might think and the potential for being treated poorly as a result. The reality is, Kelly has a beautiful gift. I do not state that in the way people often refer to those with mental retardation as being “special”. The term “special” to describe those with mental retardation is more of a politically correct motivated attempt at lessening the negativity associated with it. Consequently, many people (usually younger, immature) often use the word “special” to make fun of others, equating it with the general undesirability associated with “mental retardation”. I assure you that my use of the word “gift” to describe Kelly’s feminine side is offered in the truest and most sincere sense of the word.

Another gift mistaken for a curse
In my early grade-school years, my classmates picked up on the fact that I was more advanced (in terms of jumping ahead of lessons) than many of them. For this, I was often picked on, made fun of, and even pushed around (literally) for being “smarter” and favored by teachers. In my naive younger years, I really disliked being advanced for my age and being placed in the “smart kids” classes. I disliked it because of the negative social stigma attached by my peers. My level of advanced intelligence was, at no point, ever really a negative personal trait. Yet I was ridiculed for it and and had a difficult time dealing with all the negative attention from others. I hated being, you guessed it – DIFFERENT.

Popular misconception does not dictate true reality
It’s no secret that we live in a society that openly ridicules and punishes (in various ways) men for having the gift of femininity or not being “man enough”. Although it is true that a small minority of crossdressers do put forth a negative image and openly behave poorly (which is sadly what mainstream society often locks onto and remembers), the same also goes for any group of people. It was not long ago that black people were almost always presented in a negative light by the media and white society in general. The smaller minority of blacks who behaved poorly and committed crime took prescience in people’s minds over the vast majority of black people who lived as good-natured, law-abiding citizens. Why is that? Because in the 1950’s, much of mainstream (white) society wrongfully regarded the African race as inferior beings with little more to offer than poor behavior and menacing qualities. Did the fact that mainstream (white) society once truly believed, wholeheartedly, this unfair assessment ever make it true?

Thinking about things correctly
You’ve “got Kelly’s back” and that is so very important. You probably feel quite frustrated and helpless at times as Kelly’s personal insecurities do a terrible number on her ability to be happy and diminishes quality of life for the both of you.

The good news is that this can indeed be overcome, or at the very least, be managed better in time. The key that changes how Kelly feels, lies within Kelly herself. It is up to her, to make the necessary changes in how she thinks about this aspect of her being. All you can really do is work with her, much like you’ve been doing, and remain focused on (Kelly’s) thinking correctly.

Personal growth
In the past, my own insecurities related to being trans were so overwhelming and difficult to deal with – it almost destroyed me, quite literally. I went to great lengths to hide this from everyone I knew, including the therapist I saw for many years and even my own wife… until just a few years ago. The difficult process of correcting how I thought about things and unprogramming all of the lies that society filled my head with over the years was a journey I took alone. If I can do it all by myself, I am certain that you and Kelly can successfully work through things together. With persistence and continued (and frequent) attention spent on exploring the realities of being trans and acknowledging that the only real problem is in how mainstream society (incorrectly) views it, knowledge and reality will prevail over insecurity and idiotic social taboos.

Moving forward
I don’t have all the answers, Lori. Truth be told, no one does – no matter level of education or time spent studying any aspect of human psychology. We are a long ways away from fully understanding the complexities of human nature and emotions. We are each more than capable of making life changes and evolving though.

When you have a good block of time that can be devoted to quality discussion, please direct Kelly’s attention here. Sit with her and read through this together. If you have time before hand, perhaps browse through this site for a while and pick out some writing that seems most relevant to the troubles Kelly faces. I would suggest the Crossdressing Myths series as a starting point.

After quality time spent reading and discussing, ask Kelly if she thinks that I, too, am a “freak”. I am every bit the “freak” she is… or more accurately, like myself, SHE is every bit NOT a freak. I’d like to address directly now.

Dear Kelly
Life is short, Kelly. Do not waste it with the lies and misconceptions that your head has been filled with. Do not waste another minute being upset and depressed because of small-minded fallacies and the naive people who perpetuate such terrible ideas about crossdressers. We all must take a certain level of precaution to ensure our safety. Even though it should not be so, there are sometimes greater dangers abroad to those of us who are different. This is nothing new. Every once-oppressed group of people have had to overcome these obstacles in life. Live smart and take precautions, but try to ease up a little on the paranoia. I was once a total wreck. If I can come this far, then so can you.

It ain’t the end of the world
If you end up being discovered (or eventually decide to come out), it’s definitely not the end of the world. When I came out to much of my high school class at last year’s class reunion, the sun still rose the next morning – birds were chirping, flowers blooming, bills needed paying, and life went on after my little “secret” was well out of the bag. Life continues to go on with dozens (hundreds?) of people knowing exactly who I am – and many of them laughing to each other about it. Good for them, though. They’re the fools, not I. They pretty much dictated how I lived my life in the past because I let them. They have no bearing on my life today, and I wish them well.

A tough, but rewarding journey
There really is no such thing as reaching that “final destination” in terms of personal growth. So long as we live, we also experience, learn, grow, evolve, and (hopefully) make improvements in our lives along the way. We will always face hurdles that need to be overcome, but that is not unique to transgender folk. Everyone has their troubles. Everyone deals with insecurities. Everyone gets depressed. Everyone CAN make changes in their lives. So long as you have a pulse, you’re still in the game. You can choose to make life a more gratifying experience… or you can live in fear, allowing others dictate how you can/should live your life. That’s really up to you and I’ll not sugar-coat it.

Live your life according to who you are, and you just might achieve a real peace and happiness before your days are through. Live your life as others would “allow”, and you will forever exist in misery – much like those who would give you a hard time for being the person you are.

Do not loose sight of the fact that the pain you experience also causes pain in those who love and care for you. Lori obviously loves you very deeply. How deep does your love for her run? Don’t tell me about it – SHOW her. It all starts with a shift in thinking. That shift in thinking begins now.

Good luck
I wish you both all the best. Difficulties and struggles lie ahead, but the rewards for conquering them will be well worth the trouble. I promise you that.

Please offer your thoughts and experiences
I know many of you reading this can identify with the troubles Kelly is dealing with. What helped you work through your own insecurities? Is there any advice you can offer? Please take a few minutes to offer your thoughts to Kelly and Lori.

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17 thoughts on “Dear Gabi, My Crossdressing Honey Feels Like a Freak”

  1. Dear Lori – all of Gabrielle’s advice is sound (as always). Here from me is a tactic that you might use to help Kelly feel more at home with herself:

    Ask for Kelly’s advice whenever you can. I think that if she feels as though you can come to her, and rely on her for help, she will be proud, and she will be contributing to your happiness in the way that she wants to.

    Go ahead, ask if your makeup is good. Ask which top she would put with the skirt that you are thinking about wearing. Sandals or pumps, etc. You make 10 or 20 choices a day. If Kelly is engaged in a few of them, she will be more of a partner, and less of a freak.

    In all things, have patience. It can be a long road.

    And thanks, sincerely, for your attitude. You are a star.

    Gabrielle – you are a star too. Nice post.

    Cheers – Petra

    1. @ Petra – Thanks for chiming in and offering your take on things. :) You present an interesting tactic: simple, sound, and potentially offers multiple levels of benefit (to both).

      @ Pythos – Yes, Kelly’s girl (Lori) is fantastic! :) You’ll have yourself the “Gothic Queen” of your dreams one day, Pythos. So long as you never “settle” for that which is is easiest to find, and hold out for the RIGHT one. ;)

  2. Gabby, your response to this was fantastic. Kelly’s girlfriend is also fantastic. It is so great to read of a GG that loves all her boyfriend’s aspects.

    I hope one day to meet such a girl. She would be my Gothic Queen. LOL

  3. First, kudos to Lori – thank you for being supportive and understanding of your partner.

    For Kelly, what I hear is a tale of self-acceptance yet to be fulfilled. It’s coming – that you had the confidence to come out to Lori is a great sign of how good your self-acceptance really is. … and like all of us, your life is a journey and there is still some ways for you to go in this area.

    Self acceptance comes in degrees – as I transitioned, there were times where I was very nervous about the idea of “being discovered” – and worse, encountering someone I know who reacts badly to the revelation.

    Overcoming that was a matter of time, patience and incrementally challenging myself to take on new risks.

    I won’t trivialize it to you – reaching the point where I could tell my family that I needed to transition was a long, difficult process for me. (and bless my therapist’s heart for his patient, gentle nudging in the right direction)

    Revel in the beauty that you find as you walk your path, embrace the fact that you have someone to share it with.

    Being different is, as Gabrielle put it so nicely, is a gift, not a curse. We who are trans are given the opportunity to experience life from both sides of the gender street – something that gives us unique insights into the world we live in.

    Somewhere inside, you know this. Now you need to find the strength to live honestly and openly as yourself.

  4. By the way, to the original poster. If your boyfriend thinks he is a freak, have him take a gander at my freaky self.

    Now I am a freak.

    and I love it :)

  5. Hi Lori,

    I was in Kelly’s place not too long ago, and I can attest, it is a scary place to be. What I discovered, though, is that there are so many folks who you never would suspect of being accepting. Pythos used a phrase in another thread, “silent majority”. It is an apt phrase. I think there is a reason they are silent, tho; they do not want to be discovered to be pro-(or even indifferent to)transgender issues for the same reason we do not want to be outed.

    When I came out to my boss (long story, not worth going in to…:-), I though it would change our relationship forever; and it did! She hugged me, and actually thanked me for trusting her enough to tell her I am a crossdresser. I have a feeling there are actually more of that kind of person out there than the actual hard core anti-transgender types….

    I’m sorry, I tend to ramble sometimes…

    Honesty is very important. I am very glad for Kelly that she told you she is a crossdresser, and even more glad that you are so accepting. I know that if she finds the courage to tell other folks that she trusts the truth of her life, she will find it easier and easier to do so, and will find her self-confidence and self-image grows with each telling.

  6. OK, I just noticed your note under ‘post a comment’ about threats and authorities. Phew dear, do you receive lots of threats? Yikes!

    perhaps I’ve been fortunate, but apart from creepy guys who seem to want to chat/go out/email me I’ve been blessed not to get any threats so far. Knock on wood.

    Though, if someone finds a crossdressing website, perhaps the threat comes from it hitting too close to home? ;)

    1. Vanessa – For the most part, negative (hate filled) comments are few and far between. Generally they’re just people calling me rude names, and otherwise trying to rattle my cage.

  7. Lori,

    You keep loving and supporting him. In fact, encourage him to learn more. Together you both can discover what works for him and what doesn’t. My GF has been so supportive of me that we often go shopping together and discover “fun” for both of us. We often go out to an LGBT friendly club in town and just recently took me out full CD, it was fun. Before that she encouraged me to experiement with nail polish, underclothes, and even womans shoes while I was otherwise “Tom”. In an LGBT environment, you both can have fun, experiment and learn about what works and what doesn’t.

  8. I have been browsing this site for a few weeks now and I am very impressed with responses and the seriousness in which this issue is addressed. I came out as a CD about 13 years ago.

    It was a rough struggle to acceptance. I don’t have nearly as much time for Jacqueline as I would like these days, but I still try to sneak in an article to two of clothing into my wardrobe. I have accepted her lovingly and unconditionally over the last few years.

    Anyone going through these same things, all I can say is don’t run from her, don’t hate her, just embrace her, and love her. She is a major part of your being and you will not be able to extract her from your spirit.

    It had seemed I had this woman in me locked up in a hidden cell or compartment within me as far back as I could remember. I was so reluctant to express her but needed to desperately. My only regrets now is I wish I had done so earlier.

    Thank you Miss Gabi for your experiences and your attention given to all of these issues. You are a blessing!

  9. I cant speak for the OP or her partner, but in my case a lot of the guilt and pain came from feeling like I was cheating on my grilfriend with… the idea of crossdressing.
    It made me feel really bad!
    I didnt really understand if i was gay or bisexual or transgenedered or what, and I guess I settled on out bisexual out of convenience.
    So my point is that maybe the OP’s partner feels ashamed for these feelings and thinks of them as a sort of involuntary cheating.
    Just my 2C anyway, glad to know if you guys agree or disagree.

    Also, men are trained to be the strong physical part of the male-female dyad and so being gentle and emotional can be equated with being weak and therefore undesirable and bad.
    Personally I had to work through a lot of internal homophobia in the run up to coming out and Im very happy to let go of it forever, but I cant deny it coloured my thinking a lot.
    Ie if this girl knows Im actually emotional inside, maybe she will think I am weak, not a good partner in a marriage and reject me.
    Sorry to sound like IM talking about me all the time, Im just aware I dont know the OP and am using my own experiences as a proxy to suggest some comments! As always just my 2c. :)

    Sorry, in my last paragraph I meant to connect the bisexuality sometimes felt by CDs and internalised homophobia and shame about percieved weakness more explicitely; I wasnt implying the OP’s partner definitely has these feelings but it seems quite common and might be worth discussion!

    Shame that rears up during sex is a major buzzkill and that might be the sort of thing to trigger it. 2c etc

    What a great message!

  10. Gabrielle,

    I came across some of your earlier posts. At that time (many-many months ago) I thought you were just an excited Cross Dresser with a lot to say and talk about. But nothing at that time described the depth, the genuine love you have for your fellow human.

    Your posts are so very much full of compassion, understanding, richness, and love. I do compliment you with my whole self. I will be returning to your work often, thank you.

    The fears expressed are so close to what most of us have experienced. I agree completely with you.

    1. Thank you, Robert. I really appreciate your kind words. :)

      Life is change, and I’ve been going through a lot of that, lately (life and change). One of my purposes in life is clearly to offer help, insight and guidance to those who may benefit from it. I didn’t get a whole lot of that growing up (at least nothing helpful), so if I can offer it to others, then I’m more than happy to do so. We all benefit from it – when we help out each other. We’re all in this together, right? Trans or non-trans – we’re all in this together. It just seems like so much more can be gained (for the greater good) if we help each other out and offer support. What you put out into the universe, comes back to you. People who put out negativity, receive it back. People who put out love, receive it back. It may not always be in an *expected* form, but it always comes back. :)

      As for fear – that’s a tricky beast to tame. I still experience fear, especially when I venture out into public as Gabrielle, which I’ve been doing a lot of lately. It’s not as bad as it used to be, though. Fear is always a lie – a hypothetical situation that doesn’t exist, except for in our own thoughts, and thoughts are *not* reality. The more I challenge my own fears, the less power they have over me. I’m not fear-free, but I’m also not crippled by as I used to be. No one should be.

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