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

I am a straight SWF and actress. Can you explain why some dressers are straight, some are bi, and some are gay? Do they find dressing sexual at all? Do they have a special id with their mothers or sisters? Does each prefer specific items of clothing, or soft, silky fabric? Is the attraction to the clothing, or the idea of being a sexually appealing or soft female? Would they be more attracted to a more feminine or masculine looking and acting woman?

I have encountered many cross-dressers in Las Vegas, in and out of the entertainment industry. Most are very shy about revealing their preferences. Most surprising is that most focus on one specific garment ie shoes, lingerie, mini-skirts, that is associated with female sexuality. That is why I was trying to understand the psychology behind it.

Thanks for your response. Many girls are just curious.

Davida-Rochelle

Dear Davida-Rochelle,

I appreciate your curiosity and am glad you’ve taken the time to do a little research on the topic of crossdressing.  It is often quite the mystery to non-trans folk.  It can be a pretty big mystery, and rather confusing for crossdressers, too.  At least at first. I am not shy about this aspect of my life though, and happy to provide some insight.

The questions are often the same, but the answers are not
So why are some crossdressers straight, some bi, and others gay?  Perhaps it might put things in perspective to ponder the question: why are some non-crossdressers straight, bi, or gay?  The short answer to all of these questions is that crossdressers are as varied and different as non-crossdressers.  There’s really no way to easily sum up the choices and differences for all non-crossdressers.  The same applies for crossdressers.

Crossdressing is a mystery… but not really
The reason crossdressing seems pretty mysterious to many is simply the result of lack of knowledge, social intolerance, the taboo factor, and the fact that crossdressing is often seen as some kind of abnormality, sickness, perversion, confusion, etc.  Being trans is no more abnormal than being left-handed or having artistic tendencies or preferring the color green over blue.  Crossdressing is simply unpopular (in the mainstream), and unpopular things are often shunned.

The answer to the rest of your questions are yes or no, depending on the crossdresser being assessed.  I’d love to be able to give you a straight answer (no pun intended), but it doesn’t work like that.  Additionally, whether the answer to the questions are yes or no, it doesn’t necessarily mean that the “yes” or “no” has any direct connection to the motivation for crossdressing.

Lack of knowledge leads to incorrect conclusions
Because of the general lack of knowledge (about crossdressing) among non-trans folk, many people tend to fill in the blanks with reasoning that seems logical to them.  I would compare it to a young child watching television at an early age.  Not understanding the technology at work and having only a very limited comprehension of the world around them, it is common for young children to logically deduce that the people they see on the screen are somehow actually *inside* the device itself.

I commend you for choosing to research this topic rather than write it off as some kind of inexplicable oddity.  Perhaps the best thing you can do to understand what drives (genetically male) trans-folk to exhibit a preference toward a female appearance/expression is to forget all the cliches and misconceptions you’ve heard to this point in your life.  Keep in mind that being trans is (sadly) just unpopular and not some kind of separate off-shoot form of the human condition.  We’re all different individuals – trans and non.  Trying to figure out why someone crossdresses is a bit like trying to figure out why one of your girlfriends likes a certain type of guy, or prefers to dress in one style over another.  Why does anyone prefer what they do? Preferences are simply preferences, whether it be style, food, gender expression, or anything else, everyone has their own.

Here’s how it works for me
If it may help, I will directly answer your questions as they pertain to me.  My preferences do not reflect those of all crossdressers any more than the preferences/choices of any one non-crossdresser can represent all non-crossdressers.  I’ve interacted with many trans-folk and discovered more differences than similarities. The major similarity is the most basic element: genetic males expressing feminine tendencies, mainly in appearance and choice of self-presentation.

What is my sexual preference?
All I can say is that I love women, period.  I’ve always admired, been attracted to, and even jealous of beautiful women.  The thought of being with a male in any romantic capacity is repulsive to me.  As a tgirl, I guess I’m kind of a lipstick lesbian.  As a man, I’m just another straight guy.

Do I find dressing (in women’s clothes) sexual?
It used to be very sexually arousing to wear women’s clothing.  Over the years, the arousal (tied to dressing) has faded away. It has become more comfortable and natural feeling to dress up like and express a female presentation.  It reduces my stress, makes life more enjoyable, and in a nutshell, simply makes me feel more alive, period.

Do I have a special id/connection to my mother?
No, not in the slightest.  I love my mother, but never found her particularly attractive, nor was I particularly close to her.  I do not identify with her at all, in terms of my feminine expression.

Do I prefer soft, silky clothing?
Sometimes.  Don’t most genetic women?  I prefer that which makes me feel most feminine.  Soft, silky and comfortable are preferable, but I have a strong preference for certain styles and colors (noticeable in my photos). The feel of clothing is not as much a factor as how I look in them.

Am I attracted to female clothing…
I am more attracted to a woman dressed in a manner that I consider to be desirable (presentation, style, etc.).  I look at some women’s clothing and have a strong desire to wear them, and also see my wife wearing them, too, but I can’t say I’m attracted to the clothing itself.

…or the idea of being sexually appealing?
I do very much like the idea of being attractive in my feminine form.  Don’t most genetic women want to be seen as attractive or “sexually appealing”?  Not all do, but I think you understand my meaning. My style-preference is toward more sexy looks and I exercise daily and work hard to shape my body so that I can pull off those looks.

I think it is important to mention
My feminine form is far preferable to my male, but even in guy-mode, I put more emphasis on, and take the time to look good as a man, than most do. In the 90′s, when I was still in self-denial about being trans, I pumped iron, bulking up to achieve a muscular physique in an effort to appear attractive and “sexually appealing” in a masculine form. It’s important to keep things in perspective – the desire to be attractive and sexually appealing is pretty universal, and is not unique to transgender folk, or even genetic women. It’s common for people to view transgenderism, in its many forms, as if it is a unique category with its own separate reasoning and psychology. The reality is, most humans share very similar psychological reasoning, in terms of the desire to feel attractive and be seen as attractive by others.

Am I attracted more to a feminine or masculine woman?
Feminine, definitely.  I’ve always been highly attracted to ultra-feminine women – those who have longer, well maintained hair, put great care into their makeup, have painted nails, wear form-fitting clothes, have nice curves, and an overall highly feminine presence.  I’m not against women not wearing makeup or not choosing to appear highly “feminine”, but it isn’t sexually appealing to me (not being highly feminine).

Self-attaction
It wasn’t mentioned directly, but I think it may have been the goal, at least in part, of the “the idea of being a sexually appealing or soft female” question. Self-attraction is a pretty lengthy discussion point in itself. Like crossdressing, it is also often viewed as some kind of strange, deviant behavior. Without delving too much into actual topic of how self-attraction works and the fact that it is fairly common (among genetic women, not just crossdressers), I’m not shy about addressing it.

Am I attracted to myself? Most certainly not in my male form. In my feminine form; as a tgirl however, yes I am… sometimes, anyway. There are times when I look at myself in the mirror, or in photos, and think I look very attractive, and also experience a sense of attraction to my own image. Once again, it is important to keep things in perspective here. I’ve written about how my wife is attracted to herself sometimes, too. It’s not too uncommon among genetic women. As it becomes less taboo (mainly among the younger generation) for “straight” women to exhibit bisexual behavior, engaging in sexual acts with other women, the self-attraction aspect is also becoming less “weird & unmentionable” and more accepted as normal.

Replacing mystery with understanding
I hope this helps put things more in perspective and provide a little more understanding. Believe it or not, this is the “short response” to the very complex array of answers and reasoning required to properly address these questions. I could write a rather lengthy book on the complexities involved, however I currently lack the time to devote to such an undertaking.

Publishers (or any financial backer) interested in putting out a book on this topic, written by an author who truly understands the subject and has the ability to explain the vast “mysteries” with logical, comprehensive analysis – please contact me.

Got more questions?
If you (or anyone else) have more questions, please feel free to ask. One of the main objectives here has always been to provide education about the realities of crossdressing and reduce misinformation and misunderstanding. I recommend first reading through the “Crossdressing Myths” series as they will have many of the answers already spelled out.

Crossdressers: how would YOU answer these questions?
Like I said, my own preferences are not representative of all crossdressers. I invite and encourage my trans-sisters to address these questions. This is a perfect opportunity to share our similarities and differences, to learn more about ourselves and each other, and allow non-trans folk some real-world insight about the realities of things.

Related content:

• Dear Gabi Advice Column
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I have just approached a therapist about some sessions as I feel my crossdressing is starting to effect my relationship. My girlfriend is understanding in a way but is still not overly keen.

It is just me who will be attending, as we both feel there are issues I need to address which could all be linked. Short temper for no apparent reason like I get really mad about the most silly things. My girlfriend thinks it’s always before I need to dress. She does not want to see me dressed though. I think I need to get a good understanding of why I need to dress other than “I love that dress!!”. I feel I’m rambling on a bit so apologies for that. I don’t wish for it to go any further than our home but I don’t want to always be alone when dressed but not sure she will ever want to get involved.

I just wondered what is the main objective of this type of therapy. I am nervous and not sure what to expect.

Best regards,

Tina

 

Going to see a counselor or therapist for the first time can be a little intimidating. That’s the bad news. The good news is, most counselors and therapists are very easy to talk to and do a fine job of putting clients at ease within minutes of the first session.

Unfortunately, not all therapists have your best interests in mind. Some can be condescending, belligerent, pushy, and tell you how you should live your life rather than allow you to reveal how you’d like to live your life. If you are not comfortable with your therapist after the first session or two, discontinue seeing them and seek out another. It is also important to be sure you’re seeing a therapist who is well experienced in transgender issues.

Make sure you’ve done your homework in choosing a therapist. There are still those who subscribe to the archaic notion that transgenderism (in all its forms) as some kind of “condition” or defect in need of a “cure” rather than a personal trait. I would equate that approach to trying to “cure” someone of being left-handed or having artistic tendencies. The former was actually still employed by grade school teachers not too many decades ago. Sounds silly now, but being left-handed was once thought of as some kind of “evil sign” or “abnormality” that should be overcome.

What to expect
In terms of the “main objective” for therapy, that is up to you. Discuss with your therapist whatever you feel needs attention or isn’t going well in you life. Be completely open and honest about your life and feelings. The therapist will listen to you and ask questions based on what you share. Their job is to bring out thoughts and feelings that you may not be looking at on a conscious level, hone in on problem areas, and help you figure out how to improve on things that need attention.

When you’re in session, treat it like a conversation and not a confessional. You’re not there to “confess” anything, but rather discuss your life and issues. Everything is confidential so you can talk openly and freely without fear of ridicule or any negative judgment.

You may find that some of your “issues” are not truly problems that need fixing, but rather just things you are self conscious about. Your therapist will help you explore these things.

Although I’m offering my personal insight on some of your concerns, these things should all be brought up and discussed in depth with your therapist.

Short temper set off by seemingly little things
I understand very well the feeling of restriction and anxiety brought on by periods of not being able to crossdress. It is a sentiment commonly shared and discussed in online crossdressing communities.

Perhaps it might help to break it down on a simpler level. Dealing with restrictions and lack of personal freedom in one’s life is often a heavy contributor of stress. Remove crossdressing from the equation, and it’s still pretty much the same. When people experience the feeling of constant restriction and lack of personal choice/freedom, it takes an emotional toll. It can cause a variety of negative reactions including, but not limited to, increased anxiety and irritability – two potent ingredients in a quick temper that is easily triggered by seemingly little things.

To reference the idiom the straw that broke the camel’s back, consider yourself a camel who’s back is already loaded up with emotional baggage (stress) because of your limitations in personal freedoms. In this case, crossdressing, or the inability to do so as often as you would like, may be a significant contributor to stress. Over time it builds up, until a point is reached in which that load of stress is a bit much to bear. Any additional “straw” tossed onto the already heavy load can cause the “back to break”, or inability to control one’s temper.

One of my personal theories on why crossdressing so relaxing and has stress relieving qualities is because it allows one to break free of the socially imposed restrictions of how a man must behave and/or appear. Increased personal freedom often holds the key to reducing one’s stress level. Most people take personal expression for granted because in most cases, it does not cross the social acceptance threshold.

A girlfriend that doesn’t want to see the feminine side of you
It sounds like your girlfriend is tolerant of your crossdressing to some extent, but may never completely warm up to it or choose to participate. If she prefers a man who is 100% masculine or lacking in any signs of “femininity”, there isn’t much that can be done about that. She’s allowed her personal preferences, just as we all are. At least she knows about this part of you, which is very important in any long term relationship that might someday lead to something more.

It is in your best interest (both of you) to discuss how this may affect your continued relationship over time. Do so when the time is right; in other words, when you understand this aspect of your life better. At the same time, you should probably not wait too long before getting into this with your girlfriend.

You should try to find out if she can ever be truly happy with a man who has a strong feminine side. If she needs her romantic male interest to be 100% masculine, then it’s not fair to her to remain in the relationship. You should allow her the opportunity to enter a relationship with a man who is more compatible with her personal interests/preferences on that level.

It is also not fair for you to have to settle for a woman who cannot love you fully and completely for who you truly are; in other words, a woman who will love you completely, and not just your man-side.

How would you feel about your girlfriend potentially never fully accepting this? How would you react if she were to some day proclaim that you have stop crossdressing or she’s leaving? How about the possibility that she may try to use this aspect of your life against you – in an attempt to embarrass you in the eyes of others, perhaps in order to gain compliance with her wishes? These are each real life examples of what regularly takes place in long-term relationships (often marriages) in which the woman is not accepting of her man’s feminine side. I strongly urge you to put serious thought into your future, and discuss with your girlfriend. Again, it’s not only unfair to you if she were to try and change you, but it is also unfair to her if she needs something in her man that you cannot adequately provide by design.

There are plenty of women out there who are, in fact, openly accepting of crossdressing men. Many also encourage and enjoy it. They’re not as easy to find, but it is something to think about. You may reach a point when you’d like to expand on this aspect of your life. I once believed it would be something I never shared with a soul, let alone do in public. Now my wife knows, is an active participant (and in many ways makes possible) this aspect of my life. I simply want to be able to be myself regardless of in-home privacy or out in public. There are several people I’ve come out to thus far.

I do not imply that the relationship with your current love interest is doomed to fail. There are plenty of happily married couples in which the woman is not an active participant in her husband’s crossdressing activities. So long as there is a mutual understanding and respect, things can work out well. Open, honest discussions with your girlfriend about things is what I recommend.

Why you “love that dress”
Being drawn to and/or exhibiting traits that are generally considered to be masculine or feminine is not dependent on one’s sexual organs. That is how it’s been treated in society for centuries, but that is not how it works in reality.

There has been change in the way society views displays of masculinity and femininity over the years. Women have won many freedoms in “masculine expression”. Having short hair, wearing pants, the right to an education and voting are some of the advances made by women. It is generally not even considered a sign of masculinity anymore for a woman to have short hair, wear pants, or even wear (only) men’s clothing (purchased from the men’s department in a retail outlet).

Although women have advanced, men have not. Any show of femininity, or non-masculinity, by men is generally regarded as a weakness and/or undesirable trait. This perception does not reflect the reality (as in, it is certainly not a weakness or flaw), but rather the current state of socially accepted “norms”.

Much of society still has a significant problem in accepting certain differences in people. Simply put, the divide between those who prefer more feminine looks and styles and those who do not, is not based on one’s genitalia, but rather one one’s being. Society (people) collectively decided how men and women should look and/or carry themselves, as in what is deemed “proper”. Nature made up how men and women truly are and feel inside. It’s a LOT more complex than that, but I’m trying to express a point in short, simple terms, without writing terabytes of data on the subject.

In short, you “love that dress” simply because you love that dress. It’s not too different than why a genetic woman loves that dress or those pants on sale, or shoes, or prefers short hair over long. It’s called personal preference and style… and it’s not based on, or limited to one side of the genetic gender divide, or the other, regardless of where the majority fall.

 
Related content:

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

Halloween is often regarded as the “crossdresser’s holiday”. On this single day of the year, it is generally socially acceptable to venture out into public en femme without being ridiculed, harassed, or facing harm (from haters). Because a man dressing up as a woman is regarded as a simple “costume” rather than a social deviation, the rules are changed, if only for a short time.

In years past, I remember some of my male friends dressing up as women on Halloween. Their costumes consisted of ridiculous looking dresses, mismatched jewelry, a bad wig, over sized breasts, and absurd makeup (applied almost clown-like). I observed similar displays at various costume parties. In addition, the men behaved very much like men with only occasional feminine behaviors displayed, and usually highly exaggerated for comical purposes.

I am not a costume
Although many of my crossdressing sisters will be going to Halloween related events as their fem-selves, I will not be. The idea of “Gabrielle” being some kind of costume or sight gag is insulting. Wearing a women’s costume however, would be a very different story. A women’s Star Trek dress uniform was on my mind for Halloween this year. The uniform itself and presentation as a Starfleet officer would be the costume. Being en femme (Gabrielle) would not be a part of the costume, but rather my gender expression, or simply put – me, as in the one wearing the costume.

Poor planning
So why do you see a photo of Vamriress Gabrielle rather than Yeoman Gabrielle? The costume shown to the right here is only available online (or I could only find it online). Is I’ve said before, nothing I order online ever seems to fit. I’m rather tall (for a woman) and it would probably end up fitting more like a shirt, than a dress. Most Halloween costumes are not returnable, or involve penalty restocking fees. Because no specific measurements are offered for such an item (just small, medium, etc.), I didn’t bother. Mrs. H. and I checked out a couple of local costume stores, but they didn’t have anything comparable. Had I started my search sooner and put a little more effort into it, things may have turned out better. As friends suggested, I might have made my own… or have Mrs. H. make one for me (I can’t sew). It was poor planning on my part. As usual, time elapsed rather quickly and somehow summer morphed into October while my mind was preoccupied with other things. Perhaps next year. Truth be told, if I happened across a women’s Star Trek uniform (that fit right), I’d buy it any time. I’m a big Star Trek nerd and would love to have one just to geek out en femme, not to mention all the fun that could be had with Trek-style photos and imagery.

I’ll be en femme, but not because of Halloween
Saturday, I will be done up as Gabrielle… but only at home. Simply put, the opportunity to spend some time as Gabrielle will be present. After a long, busy week stuck in guy-mode, Gabrielle needs some time to relax and unwind. It has nothing to do with Halloween. As stated, I am not a costume and will not present myself as such. My wife suggested I “be Gabrielle” for Halloween (as in “Gabrielle” would be the costume), but I explained to her why I would only be Gabrielle for Halloween if Gabrielle had a costume to wear… which this year, she does not. The vamp-photo is just a manipulated image – I won’t appear like that on Halloween… only in the haunted digital world of the computer. Nothing worse than a byte from a digital vampiress. lol Sorry, geek humor.

Why pass up a rare opportunity to move about freely en femme?
I’ve explained why it’s not for me. Best wishes to my trans-sisters who will venture out en femme (as a costume). If you can enjoy yourself as such, then by all means, go for it. :) I’d rather see (tg) people go out for Halloween in an actual female costume of some kind rather than just en femme (as in just presenting as female in appearance), but to each her own and I respect the personal choices of others.

If I had a women’s costume to wear, I probably still wouldn’t be going out this year. I’m not much of a party-goer these days. The last time I went out to a Halloween themed event was 16 years ago. Back when I used to have more time on my hands, Halloween was a big deal to me and I’d invest much time and money into a convincing costume presentation.

Sexy = bad, but sexy Halloween costumes = good?
Ever notice how most adult women’s Halloween costumes are very sexy? Don’t take my word for it, check out this Google image search on “vampiress costume”. Perhaps a better example is this image search on a “nurse costume”. Some may call it “slutty”, but that’s usually just a sentiment expressed other women out of jealousy. Slutty is a behavior, not a look or appearance. Our sexually repressed society (mainly American) just loves to chastise women who happen to show just a little “too much” skin, or sex appeal in their appearance. Oh God forbid!

De-evolution of self-expression
It is interesting that on Halloween, it’s socially acceptable for women to express themselves in a very sexy appearance, so long as it is just a costume. Some may justify it as just “fantasy play”, which is considered to be ok on Halloween. My question is why is it only ok to be sexy in “fantasy” and not in reality? In the late 80′s and early 90′s it was fairly common for women to express themselves in a variety of sexy styles in public and at work. I loved every minute of it and miss those days immensely.

My personal feminine style is fairly sexy in presentation. Short skirts and dresses are my favorite. I love wearing them, and I’ve got the body to pull off the look. Please do not mistake my words for bragging – I pay my dues with hours of exercise every day. For me, miniskirts and short dresses are the ultimate show of feminine expression. Unfortunately, they’re also considered “too sexy” by much of society… except for on Halloween. That irritates the hell out of me.

Let’s not loose focus
Enough of my indulgence into some matters of a more serious nature that occupy my mind this Halloween. I appreciate your taking the time to read while I explored some interesting issues and would love to hear your thoughts on them. Halloween is supposed to be fun and it’s time to get back to that aspect of it.

A nightmare on my street
In 1993, I attended a costume contest at a sports bar. It was the last time I went out anywhere in costume for Halloween. There were some very cool contestants there, in a variety of creative forms. I received quite a bit of attention from people that dark and spooky evening. I went as the dream demon himself: Freddy Krueger. Rather than wear a simple (and fake looking) mask, I spent weeks meticulously preparing custom made latex facial appliances to simulate the disfigured, burned/melted look of Freddy’s face. It took about 3 hours just to apply it all properly, and was very hot and uncomfortable to wear. The judges thought my costume was not “original” and I won no prizes. Oh well. I collected their souls anyway. heh heh heh :P For those who are curious, I offer a photo (the background has been altered, but the rest is all me). I was a little heavier, my nails were very long and razor sharp and my hair was very, very short (heehee). My man-side as Freddy Krueger. I kid you not, that really is me under all that rubber, paint, and striped sweater. I believe I’ve mentioned before my fascination with slasher and horror movies.

What are your Halloween plans?
I want to know how many of you will be en femme this Halloween and whether or not your feminine Halloween costume is just you en femme, or does it include an actual female costume? I’m sure many of you will be in guy-mode this Halloween as well. What costume will you be wearing, regardless of gender expressed? Will you be going out, or just handing out candy to trick-or-treaters? Tell Vampiress Gabrielle all about it. :)

This an old argument among male to female crossdressers. Why can women dress in clothes that are considered feminine or masculine, whereas men can only dress in clothes deemed masculine? There are no laws about this kind of thing, but the socially acceptable factor has a lot of weight on how we can live our lives in the public arena.

Extending well beyond just clothes, it encompasses total physical appearance, behavior and mannerisms. I’ve put together a very basic chart to illustrate the socially accepted gender expression norms:

This chart is very general and some points may be argued, but you get the idea. We all know the clothing side of things. Women used to be restricted to wearing clothing purchased in the women’s department. Of course, over the years and it became increasingly socially acceptable for women to wear pretty much any clothing items they chose, regardless which department it was sold in or which gender it was intended for. Men however, have been stuck in the men’s department in wardrobe choices, with no signs of society letting up any time soon.

Some men might ask the question, “Why would a man want to dress like a woman?” Well, how about because some of us have a strong feminine side and have the courage to live our lives wholly rather than being restricted to all that is masculine.

The chart reflects today’s general reality. It’s socially acceptable for women to fully explore all criteria listed. Men are restricted to half of them. There was a time when there would have been a pretty clear split in choices between men and women, without much crossover.

Times have changed. Society has let up on women’s freedom of choice, but strictly enforces the man-code of masculinity, only for all humans with male genitalia. I don’t understand why choices always gravitate toward the masculine and not the feminine, but that is how things have worked out. Is there something wrong with the feminine side of things? Will feminine choices fade away completely in time, leaving only that which one might consider (today) to be masculine? That is quite an unpleasant thought to someone like me.

What’s wrong with our society in terms of accepted gender roles and appearances? How come in this day and age it is still frowned upon and even potentially dangerous for a man to express his feminine side in public?

Sadly, as some of us choose to express our feminine side, some of the more masculine men are saying, “Men dressing like women? What’s wrong with our society?” We really do have an up-hill battle ahead.

I think women are generally more open to seeing men express their feminine side in public than other men are. I’ve never heard of a crossdresser being attacked by an angry group of women. Macho men seem to have trouble with it though. Somehow the sight of a crossdressing, feminine, girly-man makes some men feel threatened. Perhaps, they may find a crossdresser/t-girl attractive and that offends their macho, homophobic ego.

Not all crossdressers will be considered attractive in their feminine form. Many simply look like a man in a dress, sometimes an ugly man in a dress. That sight may be disturbing to some people and add to the struggle of crossdressing becoming socially acceptable. I would argue that there are plenty of men and women that dress “gender-appropriate” and are just as disturbing to look at. Aside from occasional rude comments, no one seems to have a problem with “ugly people” so long as they’re “properly” dressed according to gender. I find that very interesting.

I’m not sure what it’s going to take for crossdressers and transgender people to gain social acceptance, but I believe it is achievable. In the future, ridicule and poor treatment of crossdressers will be seen as absurd as racial segregation was years ago. I just hope that future isn’t too far off. I’m not getting any younger.