My name’s Angel and I have a crossdressing boyfriend, “Sullie”. We’re still in highschool, and have been dating for two years, but I’ve only just found out that he’s a crossdresser because he has been afraid to tell me because of how I may have reacted. I fully accept him, and try to encourage him to be himself no matter what. I am 1 of 5 people who know, but none of his friends or family know.

I’m almost sadden by the fact that he had took so long, after I’ve been very vocal on my opinions about Gay, Bi, Lesbian and etc decisions in life. I myself am Bisexual, but Sullie’s the only person for me.

He’s become a shell of himself and is still nervous when he dresses around me. He feels he is a freak, and “not normal.” This is what saddens me the most. His acceptance in society won’t be felt for a while. Like said, I fully, 100% support him in any way possible. He is himself, and that’s what I fell in love with, nothing less.

Our first year together, he wasn’t the most faithful, but something held me to him. Something told me to stay. After he came out, things have been so much better. We are stronger, and I can honestly say, I have never ever felt closer to him.

Sully has always had a quality about him, a shy nature. But as he has progressed in his nature and sexuality, he’s become ashamed of himself – not at all times, but it’s definitely a mental state of depression that I hate to see him go through. He’s never been sure of himself, inside and out. Now that I know, it’s boosted him slightly, but not enough for him to come out as Sullie to other people.

I sometimes get frustrated because some of the comments his friends make without knowing honestly offend him, but he can’t say anything. He’s 16. Do you have any advice for us? And advice for confidence for him?

Angel

Dear Angel,

I can relate to Sully’s feelings of depression, nervousness, and feeling like a freak. Been there. Done that! It’s not easy growing up in a world that openly rejects and ridicules differences in people. Looking back at my own teen years, I’m amazed at how far I’ve come, in terms of conquering the feelings of shame and depression once tied to being transgender.

Your frustration is understandable. Watching the one you love experience these complex difficulties can truly be heart-breaking. The good news is that things do get better. Over time, being trans becomes less of a burden and more of a cherished personal trait. At least it has for myself and many other trans-folk.

A good first step on the road to feeling better about oneself is to reflect upon the reality of things and put them into proper perspective. There is nothing I can say that will magically fix anyone’s problems, but a little perspective goes a long way. Let’s shine a little light of reason into that murky fog of uncertainty that’s been causing so much trouble for you both.

Coming out is hard to do
Try not to feel like something is wrong because it took Sully so long to come out to you. Even if you may have welcomed the news from day one, it’s not as simple from a crossdresser’s point of view, especially at the age of 16. You seem like such an open-minded girl, and I’m sure Sully picked up on that early on. It’s a good bet that your being so open-minded and cool about differences in people plays a significant role in how he feels about you. Even so, the fear of rejection can be overwhelming.

Society is a little more comfortable, on the whole, with people being gay/lesbian. The haters are unfortunately still a plenty, but the majority of people will not have an issue in knowing that someone is gay. It is even reflected in entertainment very much today – gay characters are becoming more prevalent and are generally received positively. Crossing the gender line however, still has a long, long way to go. Crossdressing is still generally viewed as a mental illness, perversion, or many other negative things. Because it carries a significant level potential negative fallout in the eyes of many crossdressers, it makes it that much harder to come out.

If it helps any, I was 13 years into my marriage before having the confidence to come out to my wife. Needless to say, my own powerful insecurities about being transgender was a tremendous hurdle to overcome.

Feeling like a freak
I used to feel like a freak, too. So much so, that I really hated myself for being trans. I didn’t understand what it meant and was certain that if anyone ever found out, I’d be ridiculed right off the face of the planet. I would have rather died than have anyone find out. As I grew, evolved, and learned more, I felt less like a freak and became more comfortable with who I am. These days, several people know that I live part time in female form, and I’m not embarrassed about it in the slightest.

In high school, it’s pretty common for teenagers to feel like they’re a freak for one reason or another, at least at some point. I never shared my secret while I was still in school, but I remember several friends sharing things with me in confidence about why they felt like “freak”. The specifics are not important, but the reason was, and still is, always the same. The social structure in high school is all about conformity, being popular/well liked, and just plain fitting in. When something makes a teenager feel as if they don’t fit in, or wouldn’t fit in if others knew whatever (it need not be restricted to being trans), personal insecurities sprout up and wreak havoc on self-esteem. Once the nutty social structure of high school life has been left in the past, all those fears about being a freak, whatever the reason may be, fade away as little more than a bad memory about the strange beast known as teenage life.

It’s no news to you, Angel, but Sullie is most certainly NOT a freak – no more than I am, anyway. Crossdressing may not be very popular in mainstream society, and probably even less so in high school, but simply having unpopular personal traits does not mean anything is wrong or needs “fixing”.

The terrible things teenagers say
A sad reality among many teenagers is a frequent tendency to make fun of anything they feel they can chip away at. It may be just to get a laugh from friends, or intended to elevate one’s social standing by belittling others. The social structure in high school is so very different than the “real world”; life beyond high school. When you’re still in high school, it’s pretty hard to fathom any other way of life. Even if I or other survivors try to explain how different it is post-high school, it probably seems like so far away to anyone who still has a year or two or three left to go. Don’t get me wrong – people can still be plenty rude and barbaric, but it’s not as common, and the social structure is quite different.

Things are not always what they seem
There’s a good chance that Sully’s friends have no idea that what they’re saying is so terrible, or how it affects someone they call a friend. The mean-spirited remarks might be more of an attempt at “fitting in” or diverting attention away from themselves, than anything else. Perhaps certain comments are made primarily because “everyone else talks like that” and there is some “monkey see, monkey do” going on.

Unless you’re quite certain as to the underlying motivation for the mean comments, consider trying to find out. Passively studying the social behavior of people over time can reveal a lot about what is sincere opinion and what is automatic conformity-talk. I advise extreme caution should you choose to somehow confront said friends about it, though. By confronting them, potential to learn more, faster, is there, however it may also send out undesirable signals. I recommend the passive route here, unless your social prowess allows for a truly stealthy approach in your real objective when engaging in exploratory conversation with the offenders.

Some people are just shy
It sounds like Sully is somewhat shy and introverted by nature. There’s really nothing wrong with that. It’s a very common trait, and one that I share myself. Feeling ashamed of oneself when there is noting to be ashamed of however, is a different story.

Internalized transphobia
For many crossdressers, there is a strong sense of shame tied to the act of, and very real need to crossdress. Most of us, myself included, once viewed our need to crossdress as some kind of crazy compulsion that we couldn’t control, and it made no sense as to why. We’re taught (by society/peers) that we have to be “manly men” and anything not fully masculine is bad, wrong, undesirable, etc. Our need to feel and express femininity is in conflict with the social “norms” (note the quotes) of the masculine-only form and behavior that is expected of us as genetic males. That conflict, and feeling of being “all alone” in our differences, is part of what leads to the sense of shame. “We’re not like the others, therefore something must be wrong with us.”

Many crossdressers suffer from internalized transphobia. There is a fairly complex psychology behind it, but the short definition is the sense of shame that goes along with disliking (sometimes hating) oneself for being transgender. It is a learned behavior, typically caused by bearing witness to a lifetime of people expressing their dislike, hatred, detest, etc. for transgender people. That dislike and hatred can be expressed in a variety of ways, from mean-spirited jokes and disparaging remarks, to acts of violence.

Because internalized transphobia is learned behavior, it can also be unlearned. The realization that there is, in fact, nothing wrong with being trans and that it is a very normal (if not always popular) and common trait among countless men is a good start. Self-acceptance and embracing oneself as the person they are (as opposed as to what others may prefer them to be) is key to overcoming internalized transphobia and its devastating affects on one’s self-esteem. There’s nothing easy about stomping out this venomous demon, but if I can do it, anyone can, and that’s the truth. Anyone who truly wants to overcome the senseless shame can do just that.

Becoming more self-confident
I’m going to address you directly from this point forward, Sully. It’s easy to say, and hard to do, but it is absolutely true: if you believe, you can achieve. If you have a strong desire to be more self-confident; if you really want it, you will indeed achieve your goal. The key here is that you really have to want it, and not view it as a “nice to have, but…” kind of thing.

If your lack of self-confidence is, at least in part, tied to your being trans and a sense of shame over that aspect of your life, then I hope that you’ve been paying close attention to everything I’ve said so far. The feeling of being different, and the hurtful things others say about people who are different, may remain be a sore point for a while. If you choose to believe and embrace the truth over the bullsh*t lies and disparaging jokes, your insecurities about them will subside over time. It all depends on how you choose to look at things, and it is very much a choice.

You might consider writing down the things that bother and make you uncomfortable, either with who you are, or in how you feel others see you. After the list is complete, review and reflect. How many of the items are truly problem areas, as opposed to just feeling out of sync with your peers? I understand that just “feeling out of sync with peers” can carry significant emotional weight, regardless. If you keep the proper perspective about it, you may find that it’s better to be out of sync with certain people, than to be like them – especially if these people have a negative influence on how you feel about yourself.

Fake it ’till you make it
A helpful way to combat low self-esteem is to simply behave in a way that displays self-assurance and confidence to others. I’m not suggesting acting boastful or anything like that, but rather exhibiting a positive demeanor, carrying yourself with confidence, and putting out subtle signals that tell others you’re content and happy with your life, even if you don’t feel that way inside. It may not make sense to “pretend” feeling better, but this approach can be beneficial by creating a positive feedback loop. In other words, going through the motions (of feeling good/confident about yourself) can affect how well your day goes, which can in turn, have a positive affect on how you really feel, which will then create a more natural positive influence on how your day goes, etc. To be successful at it, you’ll need to be dedicated, practice, and work at it over a long period of time. You’ll also need to set some rules designed to keep yourself in check, such as: reflecting on how your day went, how your mood was, and what factors influenced them. Assess how you behaved and reacted to events that may have been stressful or upsetting, and what kind of signals you sent out to others in your reaction and subsequent behavior. Make a note of where you fall short of the kind of behavior you’d like to show the world, and think about what might have worked better if you had it to do all over again. Write them down as that can be helpful to strengthen your memory. Over time, you will be able to modify how you act in situations and even how you feel about them inside. This will only help if you work at it and stick with it long term. I hope you can put a little faith in the words of wisdom from someone who’s been there and truly understands what it’s like to experience the problems that have been troubling you.

It gets better
It gets better, Sully. That’s the truth. It may be hard to see when you’re 16 and stuck in “high school life” for a couple more years yet, but it will get better and you’ll soon be enjoying life as the beautiful person you are, rather than being ashamed of or embarrassed by it. There’s really nothing to be ashamed of… unless you intend to let others dictate the kind of person you’re allowed to be, and how you can and cannot live your life. Now that would be big a shame. I think you’re smarter than that, though.

Good luck
Many best wishes to both of you. There will be struggles and bumps along the way, but if you remain dedicated and patient, the rewards of your efforts will be well worth the investment.

Related content:

• Dear Gabi Advice Column
• Write to Gabrielle: Dear Gabi submission page
• Crossdressing Myths & Misconceptions
• Until Society Has Their Way With Them

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??

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.

 
Related content:

• Dear Gabi Advice Column
• Write to Gabrielle: Dear Gabi submission page
• Until Society Has Their Way With Them
• Crossdressing Myths & Misconceptions

I have been under great stress at work. I still have a job but I feel trapped I can’t be me. You are free and have the support of your wife. I don’t know what to do any more, I can’t come out at work or I’ll be fired for being TG, I’m thinking of seeing a therapist but have a strong fear that if I use company med. insurance it may get back to the new owners of the company and I’ll be fired.

I have been hoping to find support in online TG communities. I’m not a kid anymore. I’m also 55 years of age and I’m not pretty like you and many other t-girls I’ve seen. I love your goth picture.

God if only I had the money to free me from working and the money to transition and live my true self as Margueritte full time, may I ask you how you can live and be both male and female with out the homophobic BS from people around you? Sometimes I think of taking a bottle of sleeping tablets and just ending it all. How do you handle the pressure and depression?

Trapped
Margueritte

I understand your feelings of being trapped, frustrated, and depressed. Trust me when I tell you that you’re not alone.

Health insurance privacy
Seeing a therapist using company provided insurance will probably not result in your employer finding out. My own employer is unaware of the fact that I’ve been seeing a psychiatrist. My health insurance covers most of the cost, but that information is not shared with my employer. Call up your insurance provider (directly, not through your company) and ask what the policy is on that. You should be able to find out one way or the other and take it from there.

The illusion of beauty requires quite an investment
Your compliments on my appearance are much appreciated, but the reality is I work very, very hard to look like this. Some are thin and attractive naturally. Others have to really work at it. I fall into the “others” category. I was not blessed with the “thin” gene and have to spend hours every day exercising. I also have to watch my food intake because my body has a naturally slow metabolism. It is a lot of very hard work. Chances are, most people who are willing to subject themselves to a strict diet and commit to a daily exercise regimen will look physically fit and more attractive for the effort. Like many, I also struggle with vanity issues and cannot live up to my own desired standard of beauty. There are dozens of t-girls out there (and genetic women, for that matter) who’s beauty I’m quite envious of.

How I do it
When it comes to “how I do it” – in other words, how I live my life as the man and as the t-girl, with such balance and freedom without the BS and pressures getting to me… the answer is I do not. I have yet to achieve a good balance, and it does get the best of me sometimes. I really have to put forth a conscious effort to rise above all the garbage, hold my head high and keep moving forward. It is a simple choice I make and hold myself to. There’s nothing easy about it.

My loving, accepting wife
My wife knows and accepts my feminine side. She has been very helpful in making “Gabrielle” possible. At the same time, our marriage is far from perfect. Being a transgender has not caused trouble, but this is but one aspect of my life. There are plenty other aspects she isn’t so happy about. Many (tg) people perceive her acceptance of me as a crossdresser as “marital bliss”. It only means that this single aspect of my life does not cause trouble. Our marriage is a good one, but we both have to work hard at it.

Living in a society filled with hate
There’s nothing easy about dealing with society’s bigotry and hatred. It is ironic that on the day you sent your message, I was terribly stressed out and very depressed myself. Trouble finding ways to be out in public (en femme) safely, and my inability to move freely in society as Gabrielle had really gotten to me. Despite my photos, in person, I am usually easily read. That translates to standing out and drawing negative attention in my town. Although I refuse to let the dangers (hate-filled thugs who may do me harm) prevent me from getting out, it does greatly complicate things.

Suicide is not a solution
Years ago, I thought suicide was the answer to my own depression and troubles. Now I am so grateful that I lived through the terrible things I once did to myself. Had I succeeded, I never would have met my beautiful wife and enjoyed all the wonderful experiences I have in life. Nor would I have ever gotten the opportunity to become the lovely Gabrielle. None of this would have existed.

Nothing is easy in life, but it’s always worth living
Some people have easy lives. It’s just a fact. For many of us however, life is not so easy. Try to recognize the areas in your own life that you are not happy with and figure out what you need to do to improve upon them. You’ll have to work hard on making your dreams a reality. They most certainly will not magically come true on their own. Best to attack one problem at a time though. In addition, take things one day at a time.

What to focus on first
I suggest you look into seeing that therapist you mentioned. It sounds like a good starting point to figure out what it is you want, and what it will take to achieve it.

Life is full of challenges and obstacles to overcome. I have overcome much adversity in my own life – things I once believed not possible. I think you will too, Margueritte.

 
Related content: Dear Gabi Advice Column

Write to Gabrielle: Dear Gabi submission page

 

I did not nor do I now understand crossdressing. I was raised very religiously and naive as to what the world’s about. When I met my husband, 30 years younger than me, his mom would say that once we got together his bisexuality and crossdressing would not be there, but to my horror it was an every day thing and that he wanted to be a girl.

I’ve tried for all these years to deal with it give him some of my clothes, watch porn, deal with him chatting with his gay and crossdressing friends that don’t understand where I’m coming from. I’m severely depressed and this has only driven me farther and farther into it. I had problems before but this has escalated it.

After his mom’s death he wanted to start it up again and I said no. For the first time in our marriage he’s talked about it, now wants to go on with his life as were separated, and moving in with another bisexual and soon there will be a relationship there. He led me to believe that we could work things out sometime in the future but hit me with separation (same as a divorce) and he’s moving on and being what he is. This has torn me up and anxiety depression and feeling inadequate and the scum of the earth.

I’ve asked the docs and therapists for help it’s not enough. All I do is cry and feel like a complete failure. Even though I should just not talk to him and cut the ties, I can’t do it. My love is so deep and yet it’s obvious he only used me for money and getting what he wants. I’m not trying to step on any toes here, I just don’t understand and it’s messed me up so bad I can’t function. I have serious health issues and yet I can’t get disability and I’m on Lexapro and Clonazepam, but they’re not working. They won’t let me see another doctor or counselor and tell me to deal with it.

The same as my husband tells me about his crossdressing and bisexuality, the only support I have is my family and friends who think he should’ve been honest before we got married when he only wanted to talk when he was in my clothes! That’s not the time to talk to me about it. This is a lot of info and I’m sorry. I’m trying whatever I can to get help to get understand and I’m tired of hearing it’s not me. I feel after this being the 3rd marriage and other relationships have gone bad and left me with feeling very inadequate, I’m a failure and shouldn’t have been born.

Thank you for at least listening.

Chris

I am so sorry to hear about your failed marriage and painful emotional struggles. There is nothing I can say or do that will heal your broken heart, but I may be able to at least shed light on some things that don’t make sense to you.

Crossdressing is different from one person to the next, therefore I cannot adequately spell it out in simple, logical terms. In general, it’s a man’s need to express his feminine side. Like being left-handed or naturally athletic, it’s a personal trait and not something that goes away or can be “cured” any more than one can “cure” being left-handed.

Bisexuality is a person’s attraction to and romantic interest in both sexes. It is not linked or directly related to crossdressing. Most crossdressers are, in fact, heterosexual men with no romantic interest in other men whatsoever. Most gay and bisexual men are also not crossdressers. Sometimes crossdressers happen to be gay or bi, and sometimes gay or bi men happen to be crossdressers.

May-December romance is tricky at best, depending on the age discrepancy. Romantic relationships between couples, in which the age difference is significant, tend to have less of a survival rate than couples who’s age does not differ greatly. The 30 year gap between you and your separated husband is pretty significant. Although age difference alone does not necessarily mean a relationship is doomed to fail, it certainly plays a considerable role.

I understand that you knew little to nothing about crossdressing or the significance of one’s sexual orientation before getting married. It was ignorance on the part of your husband’s mother to suggest it would go away once the two of you got married. Marriage does not change one’s sexual orientation/preference or their need for feminine self-expression.

It was admirable of you to try and be open to your husband’s crossdressing and sexual interests. Unfortunately, his desires (and perhaps needs) went well beyond just crossdressing and porn. You should not see this as a failure on your part because it has nothing to do with who you are as a person, and everything to do with what your husband wants and needs in his life. In other words, do not blame yourself for your husband’s behavior.

I can’t help but wonder if your husband may be more of a transsexual than a crossdresser based on your saying “he wanted to be a girl.” If that is the case, it is likely he has felt this way for a long time. Crossdressing and transsexualism are two very different things. Although both may involve the act of crossdressing (as in someone who is genetically male dressing as a female), the motive for doing so differs. Both are also very complex subjects and explaining the differences is better suited for a series of lengthy books.

You are absolutely correct in that your husband should have been more honest with you about his long-term interests and desires. Life is a discovery process however, and it’s possible that he may not have understood these aspects of his own life when the two of you were engaged to be married. Regardless, he was not as open and forthcoming with you as he should have been. This is, unfortunately, somewhat common among transgendered people. The fear of rejection compiled with the desire to live a “normal” life often keeps people from being completely honest about these things prior to marriage. It doesn’t make it right, but it does explain why it happens.

Marriages do not fail because of crossdressing or sexual orientation. They fail because of compatibility issues, lack of respect, and poor communication. In your story, I see some significant compatibility issues, and lack of communication. The respect factor is debatable and unclear in your letter, but the other two shortcomings are more than enough to cause a break up. For a marriage to work, both parties need to be equally committed and devoted to making it work. Both have to want it to work.

Although you have expressed difficulty in letting go of your husband, it is probably in your best interest to do so. You cannot hold on to a man who does not feel for you, as you do for him. It’s not healthy and nothing good will come of it. The sooner you let go, the sooner you can begin to heal and move on with your own life. You deserve a man who loves you completely and can commit himself to you in a monogamous relationship. Do not settle for less.

Before attempting another relationship, I suggest you work on your severe depression and low-self esteem. Depression, low-self esteem, and insecurities will cause serious trouble in any relationship. Failure to get these issues under control prior to entering another relationship will only result in another heart break.

There is no easy fix for depression, but it can be managed if you choose to work at it. Your solution will not be found in a pill or therapy alone. Medication and counseling can help, but the rest is up to you. Understanding this important point may be your first step to true recovery.

You’ve been through some difficult times and I hope that you’ll not think poorly of all crossdressers because a single man, and/or his friends. I am a heterosexual crossdresser in a monogamous and committed relationship with my wife. She knows all about my crossdressing and enjoys this aspect of my life with me. Of course, not all women will enjoy being with crossdresser. If the idea of crossdressing in and of itself is not a desirable quality in your eyes, that’s fine. Lucky for you, most men are not crossdressers. Everyone is allowed their opinion, but you should not sum up all crossdressers poorly because one caused you pain and suffering. Every group has its bad examples. Most of us are good, devoted husbands and fathers who are completely committed to our wives and families.

You’ve got some rough times ahead, Chris. I hope you will choose to overcome your troubles and move on with your life. The pain you feel will not be there forever. You’re old enough to understand that. This is a temporary state and you will come out of it stronger and wiser for the experience. You’re a good person and deserve to be happy. Do not place your self-worth on the success or failure of a relationship, but rather on your own good qualities. I believe in you, Chris. It is time to believe in yourself.

 
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It seems like a million years ago and just yesterday at the same time. I was 12 years old and it was undoubtedly the single most traumatic event of my youth. The devastating emotional impact lasted for many years after.

I first realized my desire to dress in women’s clothes at about the age of 3 or 4. I didn’t know what it all meant, but I knew enough to keep it a secret. It’s interesting that even at such a young age, the social taboo of crossdressing was already heavily cemented in my mind. It seems like from the time I was born, I was taught of the need to fit in to the socially accepted norm of the “male gender role” because of my sex. How else would a 4 year old know to guard this little secret as if his life depended on it?

Unfortunately, I did not guard my secret well enough. One evening, while my parents were out, I took advantage of the opportunity to try on one of my mother’s skirts. I had done this in secret several times throughout my short life. I don’t know how my mother entered the house, walked up the stairs, and opened the door to her bedroom without me hearing a sound. I just remember hearing her voice out of nowhere saying, “What are you doing?” Stunned and terrified, I looked up to find her standing in the doorway just a few feet away.

“I just wanted to see what it felt like to wear a dress.”, I replied. It was really a skirt, but I used the two terms somewhat interchangeably then. With a stern angry look on her face, she told me, “Get it off.”, and then gave me a brief moment of privacy to change.

My parents weren’t supposed to be home for some time yet. There should have been some kind of noise when they entered the house. No, this didn’t just happen… My mind was racing with terrible thoughts while trying to process the reality of the situation and figure out what would take place next. I’m some kind of terrible freak, committed a sin sure to land me in hell, and my mother was probably about to send me there herself.

She came up to my room to talk with me a short while later. A was asked a lot of questions, one of which was had I ever done that before. I lied and told her it was the first time. I pretended to just be curious about what it felt like to wear a skirt and how to sit properly while wearing one, etc. I begged her not to tell my father. I’m not sure if she did or not, but he never mentioned it. I don’t remember the whole conversation we had, but it really made me feel bad about who I was.

I was terribly embarrassed by the incident. I wasn’t sure if she bought my explanation of simple curiosity. I knew what I was… or at least that I liked dressing like a girl. Everything in my world told me that it was wrong to have desires like that. Now my mother knew as well, or so I believed she did after getting busted.

This incident in my life marked the beginning of my downward spiral into the madness, depression, self-loathing and confusion that became my teen years. This was the day I began to really hate myself. I put on women’s clothes, liked it, and my mother witnessed. I believed that the only thing worse than dressing like a girl was the fact that I actually wanted to dress like one. What was wrong with me?

Society has pretty strict rules about this kind of thing. Men/boys have to be masculine, period. Being a “girly-man” is something one should be ashamed of. I wanted to be feminine and pretty, but everything around me indicated that was wrong and that I was a sick person for being this way.

I didn’t know how to deal with the intense embarrassment of getting caught and scolded by my mother. I couldn’t have felt worse about myself. There was no one I could turn to. I didn’t understand why I was this way. I couldn’t erase what happened. I wanted to die. Death was far preferable to living as some kind of terrible, worthless freak that people would surely laugh at, ridicule, and maybe even harm if they knew.

In my later teens I made multiple attempts to kill myself, getting a little closer to success with each try. It landed me in the hospital on a couple of occasions. I almost succeeded that last time. Being a crossdresser, and feeling terrible about it, was at the heart of my own insecurities, low self-esteem, and deep self-hatred. I couldn’t tell anyone though.

It is interesting that as I think back to this time in my life, the memory is still very painful and intense. It causes me to tear up if I recollect for too long. I will forever bear the scares of my suicidal stupidity – reminders of my dark past and how far I’ve come.

My story has a happy ending though. It took a little more than three and a half decades to figure out, but I finally learned how to accept myself as a crossdresser. There is nothing wrong with who I am – the problem lies within the social stigma of being a crossdresser and the way much of society treats us.

It is not a sickness, addiction, compulsion, disorder, or something that requires treatment to overcome. It is, in fact, simply who I am. Just as some people are born left-handed, some men are born with a strong feminine side. Ask any trained psychiatric professional and they will confirm. For whatever reason, society frowns heavily on such things.

When I accepted who and what I am, I stopped hating myself. I even learned how to love myself. I cannot properly describe the beautiful feeling – truly loving who I am. It is something I once believed to be never achievable. I now love being a crossdresser. I’m a girly-man and don’t feel bad about it at all. It is simply who I am and I love being me. I still have to hide my feminine side from most of the world in order to hold down a job, etc. but I’m not ashamed of who I am anymore. God made me this way and I thank Him for it. The dark beast within turned out to be a beautiful gift. I now cherish and celebrate it.

Since embracing who I am, people who know me have noticed that I’m happier and a lot more easy going than I used to be. It surprised me that people noticed the difference and actually mentioned it.

If you’re a crossdresser and currently hate yourself as I once did, I share my personal struggles to let you know there is hope. You’ll never be cured of your desire to crossdress because there is nothing that can cure you of who you are. You can however, be cured of your self-hatred. There is nothing wrong with you or your desire to express yourself and how you feel by crossdressing. The only problem is with anyone who would try to change you or “fix” you and have you become someone that you are not.

If I learned how to accept who I am, then believe me – so can you… when you’re ready. I just hope you don’t take as long as I did to figure it all out. You’ve got a gift. Try to embrace and enjoy it. Anyone who says you’re crazy or would try to change you – they’re the one with the serious problem, not you. There is nothing healthy about trying to change who someone is when there is nothing wrong with them in the first place.

If you’re not a crossdresser, I hope this has somehow opened your eyes to what many of us go through. There is no reason to treat us poorly. We’re not freaks or terrible people. We feel pain just like anyone else. I hope you won’t look down up on me or anyone like me because we choose to be ourselves and embrace life as we are. Try to be open minded. If you know a transgendered person, please try to make them feel welcome in this world. Everyone needs to feel accepted for who they are.

It all seems so senseless to me now. There was no need for me to ever feel so bad about who I was. Why are gender differences treated like some mental disease by most of society? Why aren’t we taught the truth about this when we are young? Why is it such a big secret? Why is being a crossdresser something to make fun of? Who the hell began this way of thinking? Why are kids today still “protected” from such knowledge or taught that it is wrong it is to be this way? What purpose does all of this negative treatment of transgendered people serve?

Perhaps the most important question is how much longer will this continue? Sadly, the world is full of crossdressers who still hate themselves, and needlessly so. How many of them will succeed in their suicide attempts? How much longer will they live a life of personal torment? No one should ever have to suppress who they are in order to be accepted and respected. If someone is an ax murderer, then yes – repression is good. But simply being a crossdresser – what’s the problem, here?

I’ve met some very interesting crossdressers and become good friends with a few. Unfortunately, I’ve also come across so many crossdressers who are confused about who and what they are. Many of them hate their lives and hate the fact that they feel the need to crossdress. Many more have accepted themselves as they are, but are married to a woman who does not accept their crossdressing. The old “I married a man, not a woman” argument flies frequent and furious in online crossdressing communities. My wife accepts me… why not the wife of every crossdresser? What’s wrong with them? How can I help?

Seeing so much pain in people, fellow crossdressers that I can relate closely to, caused quite an unexpected burst of emotions in me. I wanted to incorporate crossdressing more into my own life and at the same time help other crossdressers find peace and happiness in their own lives. The emotions caused me much stress and difficulty sleeping at night. I decided to go back to my old psychiatrist and discuss an important point that I failed to share before.

There I was back on the couch: this time older, wiser, and with very specific goals in mind. I showed my doctor some photos of Gabrielle to which he said “she’s a very attractive woman”. I thanked him for the compliment and explained that she’s me. He asked me a series of questions to determine my sexuality and where I’m at with things in this aspect of my life. At the end of the session, he determined that I’m heterosexual, not “a woman trapped in a man’s body”, not looking for a sex change, and very comfortable with my crossdressing. He gave me a clean bill of mental health and flat out told me “you’re certainly not crazy”. He also said that we should have a few more sessions to sort out my flood of new emotions, which I agreed. I’ve never been happier in my life and I’m planning on making some big changes. I want to do this right.

My doctor made a very interesting point as the session was coming to a close. I told him that I felt like I had wasted so much of my life forcing myself to be someone I’m not – the “man” society expected me to be. Yes, genetically, I’m male. I love the (real) ladies. But I also love being girly and feminine… only was never allowed to be. This is, word for word, exactly what my doctor told me: “Most crossdressers start out their lives as very normal people… until society has their way with them.”

There are so many confused people out there – crossdressers who hate themselves, hate their lives, and live with women who do not accept them for who they are. They grew up, much like I did, in a society that seems hell bent on forcing people into one of two very specific gender roles based on the sexual organs one is born with. Girls are allowed to be feminine, or not so feminine. Men are pretty much only allowed to be masculine, period. From the time we’re born, these gender roles are taught, enforced and re-enforced over and over. It literally starts when we’re born. The very names we are given are gender specific. I could easily go on with a zillion examples of how society’s gender rules are taught, enforced, and the terrible consequences for not adhering to them.

Why is it we live in a society that sees fit to force people into roles that are not who they are? I’ve heard it said so many times about crossdressers: “You were born a man, why not be what God made you?” Well, that’s the problem. I’m being EXACTLY what God made me – I’m a crossdresser; a man with strong, natural “feminine” preferences and behavioral traits. I first realized this around the age of 3. It was hard-wired into my brain from the start. I sadly spent most of my life trying to be something I’m not – a manly man.

The main point I wanted to make is about what my psychiatrist said. Many people think that crossdressers are mentally sick and/or perverted, deviant freaks. And while some crossdressers probably are, so are many more non-crossdressers. What my doctor, said is very true. He’s a prominent psychiatrist, now in his 60′s, who deals with this issue all the time. How I regret never speaking with him about this when I was so much younger.

We start out very normal… then society does its best to force us into being something we’re not, and teaches us that what we feel inside is wrong. What kind of mind-f*ck is that? Is it any wonder so many crossdressers are so messed up? Is it any wonder that they end up in marriages with unaccepting wives? They probably got married long before they accepted who they are them self. I know I did. In a perfect world, all this stuff would be explained to a perspective wife long before taking the vows. And in a perfect world, society would encourage people to be themselves and not force ridiculous gender rules based only upon sex organs and some archaic, idiotic reasoning that has been handed down from generation to generation without question.

To hell with that crap. I choose to be me. I was never happy trying to be what society expected me to be, but I sure found happiness in being myself. It pains me that I cannot yet move about within society as I would choose to be because it can be dangerous to do so in my neck of the woods. But that’s a story for another day.