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
• Write to Gabrielle: Dear Gabi submission page
• Crossdressing Myths & Misconceptions
• When Did Sexy Become Slutty and Why?

This is entry #5 in my vlog series. Hard to believe it’s been over a YEAR since posting my previous video! It honestly doesn’t feel like that long.

There’s been a lot going on in my life, which is why I haven’t been able to keep new content rolling out on a regular basis. I was however, able to take a little time and make this short video. I hope you’ll share a minute or two of your day with me to watch and comment. Video running time: 1 minute, 21 seconds

About the video
The video was shot on May 29, 2011 with my iPad 2, and later edited on it (mostly). The main reason for making it, besides the fact that it’s been so long since my last, was to put something out there and let people know I’m alive and well and… well, still me. Over a period of time, several people wrote to me and asked if/when I might publish another video.

For the record, if this ends up being the last video I publish, ever, please understand that I’ll ALWAYS be me (as in Gabrielle). Do not mistake my lack of time to write/share, as being anything other than a lack of time to share. Time permitting, I’d like to make more videos (and content in general) to explore and discuss various things in the future.

A picture in a picture in a picture in a picture…
The video was intentionally framed to show my back side in the mirror behind me. Not to show off my literal “back side”, but rather to offer another view of me actually holding up the iPad while talking into it. If you look carefully, you can see the iPad screen in the reflection, and in that screen, another reflection with another screen, etc. – kind of like holding two mirrors up to each other.

Gabrielle the musician(ish)
The background music is a custom arrangement by yours truly! I’ve always enjoyed experimenting with sound and music, though I’m far from being a real musician. The music track was made in a music composing application by dropping individual instrument “loops” (short audio clips) onto a timeline to form the final composition. The final result is a unique creation and I’m happy with how it turned out. If you’re a musician or just like to experiment like I do, tell me about it!

My first published iPad 2-taken photo!
The iPad 2 is an amazingly cool and versatile device. If you have one, you’re probably aware of the less-than-amazing quality of the cameras it sports. In good lighting, the image quality is pretty decent, but the lighting fairly dim where I took the photo shown here (also featured in the opening and closing of the video – click it to enlarge). I don’t think the photo turned out too bad… aside from it being grainy with blotchy color. I tweaked it a little (also on the iPad). Sorry about the blah pose – it wasn’t easy trying to take a decent self-photo in a mirror, in a small, confined space, while awkwardly holding and aiming the iPad 2 to capture the image.

If you’ve done any iPad 2 photography, chime in and let me know about your experiences.

Talk to me!
Please take a minute or two to answer the questions I posed in the video. Although I directly asked about “YouTube subscribers”, the broader intention was simply: What do you like about my video offerings? What, in particular, would you like to see in future videos? Tell me what’s on your mind – leave a comment or shoot me a private message if you prefer (using the contact link up top).

Thanks for watching (and reading), and have a beautiful weekend!

Related content:

• My YouTube Channel
• My Flickr photos
• Vlog entries

I’ve just recently discovered your website and wish I would have earlier in my exploration of crossdressing. ;) I’m 18 now and have accepted who I am, been dressing up since I was young, 5 or 6. I’ve come to terms with a lot of stuff, and I’m no longer ashamed of who I am. I have a loving girlfriend for almost a year now who knows everything as well, she is very accepting and supportive =)

My problem deals with my sexual orientation, I know I’m attracted to girls, thus my girlfriend, but while dressed, I find I’m always craving guys, so for a while I just thought I was bisexual, until when I was 16 had my first relationship and sexual experience with a guy. Now he was a full time crossdresser, even during high school, I think that was the main attraction. I was so turned on being with him, and kissing him. Anything to do with touching or seeing his genitals didn’t turn me off, but didn’t turn me on. I love the feeling of anal sex (from a male), turns me on immensely.

So basically I’m kind of confused, I look at a normal guy and I’m not turned on, but I always find myself thinking about having sex with a male and strap-ons with my girlfriend just doesn’t feel the same. I know it’s a vague question as well, I’m still young and exploring and advice would be amazing :)

Angel

Being a teenager is tough, period. When social taboos and sexual orientation uncertainty comes into play, it can make life that much more confusing and stressful.

Social “norms” vs. reality
In terms of your sexual orientation, your confusion is probably the result of feeling out of sync with the “social norms” that have been etched into your brain since birth. Your feelings are in conflict with that which you have been taught is “normal” and/or “acceptable” within society, hence the uncertainty.

Sexual preferences
You’ve expressed being attracted to both men and women. The definition of “bisexuality” (taken from Wikipedia) is sexual behavior or an orientation involving physical or romantic attraction to both males and females.

In terms of being attracted to woman as a man (not crossdressed) and being attracted to and/or fantasizing about men when you’re dressed as a female (crossdressed) – I’ve read many accounts of this kind of sexual preference expressed by other crossdressers. Categorically, it still falls under bisexuality. Exactly “how it works”, applicable terminology and semantics are often discussed to great length in transgender communities and message forums. There is a rather complex array of attraction preferences that may be explored and debated. My assessment and opinion is based on the context expressed in your letter.

It certainly sounds to me like you’re bisexual. Maybe pause for a moment and ponder that reality for a bit. There are literally millions of bisexual people, a percentage of which are crossdressers, too. You’re not alone in how you feel about men and women, sexually. People like what they like. Being bisexual is nothing to worry about or stress over. It’s just a very common (even if not always popular) personal trait, shared by many people.

Regardless of how or when you prefer romance with a female or male companion, perhaps what is most important is simply being with someone you love, enjoy, and are compatible with, who feels the same about you. It sounds like your current girlfriend is a pretty awesome gal, based on the little you’ve written. I hope you appreciate her and let her know how much she means to you.

Sexual curiosity, fantasy and monogamy
Whether you are involved romantically with a man or a woman, many partners tend to prefer a monogamous relationship. If your girlfriend (or future lover, be it girl or boy) is expecting an exclusive/faithful relationship, then it really doesn’t matter if you prefer women sometimes, and men other times, because you’re already taken. Even for straight couples, the question of “I’m with this person, but I really like that person, too. What should I do…” often pops up. It doesn’t matter if you’re attracted to another woman or a man. Cheating is just that – cheating. Unless you’re in an open relationship (as in you both agree that seeing other people is acceptable), feel free to look around and fantasize, but you’d best remain physically and emotionally loyal to your girlfriend (or current partner).

It sounds like you’re pretty happy with your girlfriend, even though you have a craving for men at times. Straight, gay, or bi, very few people ever have the opportunity to experience every sexual fantasy they desire. I’ve fantasized about many, many women over the years – far too many to count or even remember. Being married, I still look at and admire other women (and always will), but my wife and I enjoy a monogamous marriage. Point is, everyone fantasizes. You just happen to fantasize about women and men, but again, that is just how it works with bisexual people, trans or not.

Fear of the unknown
If you find yourself wondering “Where is this all leading?”, be it your sexual preference, gender identity, or anything related – try not to worry about it. Perhaps easier said than done, but it’s good advice, nonetheless. Remove sexuality and gender from the equation, and understand that most people still wonder where things are going in their lives. There are a zillion things we all sometimes feel very uncertain about. That’s not unique to trans folk, bisexuals, or any other segment of the population. It is common for people to make a bigger deal out of things when gender identity and sexual preference come into play, but that’s mainly due to those things being (generally considered) outside social “norms”.

Plan for the future, but live in today
Here you are today – not necessarily a physical location, but rather simply your place in life as it stands at this point in time. Did you have a good day? Was there something (hopefully many things) that made you smile? Did you make anyone else smile? Who knows what the future holds for any of us: trans, straight, gay, bi, or anything else. Life is a journey – one that is very unique for each of us. Try to enjoy each little pit stop along your journey and don’t stress over where your path leads. Enjoy the happy moments that each day holds. We all have bad days and hard times, but try to concentrate on the good times. Don’t loose any sleep over social “norms” or exactly what category [whatever] happens fall in to. Just be yourself and be a good person. You may experience changes in how you feel about or view things over time. That’s a part of the growth and evolution process we all experience, regardless of orientation or gender.

Teen life is a strange, strange place to be, so try not to let thoughts of being “outside the norm” get the best of you. In a few more years, you’ll realize that you are, in fact, very normal… or that no one is truly normal… or probably both.

Good luck!
Relax and make the best of things as they are. There’s nothing wrong with you. Seriously! Not based on anything you’ve written. Take things one day at a time and enjoy being young.

 
Related content:

• Dear Gabi Advice Column
• Write to Gabrielle: Dear Gabi submission page
• Crossdressing Myths & Misconceptions

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

This is entry #4 in my vlog series. It’s been a few months (about five) since my last vlog was published. My, how time flies!

Clocking in at a whopping 30 seconds in length, this is my shortest vlog to date. Sometimes less is more, and I think this is a good example. It’s short and sweet. My apologies if you were hoping for something a little longer. You can always play it again a few more times. Don’t worry, it won’t wear out.

Why so short?
The video footage was actually recorded a few months ago, and meant to be longer. Trouble with my editing tools had me spinning my wheels and I gave up on it after a while. I talked about it in this post.

After playing around with some of the footage on and off, mainly as a creative exercise, I settled on an interesting, stylized visual presentation. A few short snippets of the original version were chosen to appear in the final 30 second video. It seemed more effective and meaningful to keep the “message” short and sweet. In the end I liked how it turned out, and there you go.

The day after
Like the video, this write-up also had to be chopped down to a more manageable size. I have a tendency to ramble on about my creative interests – in this case, video production and visual style. It was enjoyable to indulge, but most people don’t come here for that kind of thing. It seemed to clutter up the post, rather than add to it. Another good example of less being more effective. Exactly one day after publishing, I removed six paragraphs of “clutter” for a shorter, tidier post.

Where do you go when you’re “all dressed up”?
Like I asked in the video, is there a welcoming and safe environment you can be yourself and fem-out? Perhaps like myself, you find yourself all dressed up with no place to go? Please take a few minutes to share – either way.

Disclaimer and reminder
I have little control over the suggested videos offered after mine finishes.

Related content:

• My YouTube Channel
• Vlog entries

It’s been a while since I’ve had an opportunity to get out in public as Gabrielle. My wife, the fabulous Mrs. H., recently took me shopping at one of the local malls. It marked the first time we ventured out in public together, while I was en femme (not including drives we’ve taken in which I did not exit the car).

My public outings have had mixed results in the past. To increase the potential for a more successful outing, I took some drastic measures this time, or at least drastic for me.

In order to draw less attention and increase my odds of blending in with the crowd, I did something rather undesirable. I wore pants. I hate pants. It may be crossdressing cliche, but I really do hate pants. Women have been wearing them for several decades, but I just don’t feel very feminine in pants, even women’s pants, or skin-tight jeans in this case. At least I looked good in them, according to my wife. I do admit, my legs still have a nice, feminine shape in jeans (thanks to my daily treks on the treadmill of doom), but it’s not my style and I wasn’t happy about it.

The activity was shopping, but this outing was mainly an experiment in blending in – something I’ve failed to do in past public outings. I like to dress nice. What I consider “dressing nice” and “looking good” falls under the category of dressing “sexy” in the eyes of many people. We’ll spare my gripe with how society tends to frown upon “sexy” these days, but that is my preferred style and how I feel best.

What I wore
My outfit consisted of tight bluejeans, black knee-high boots (flat, not high-heeled), a black turtleneck sweater, and an outer black button-down sweater (that fell just below my hips) over it. My only accessories were a gold crucifix necklace, and basic black purse. I toned my eye makeup down dramatically and was careful not to over-do it on my blush. Mrs. H. and I had similar looks going on, each wearing black tops, tight bluejeans, flat (non-heeled) black knee-high boots, and black purses.

I snapped a few quick photos on the way to the mall while my wife drove, one of which you see at the top of this post. You can see her long, black hair draped over her right shoulder at the right edge of the photo. Sorry about the lack of a bull-body photo of how I looked in what I refer to as “fem-drab”. I didn’t feel compelled to capture my image in this less than desirable style. Update: Scroll down and click on the thumbnail image at the end of this post to see how I looked in the pants I wore.

As much as it pained me to dress down, it did help in terms of not drawing attention. As I’ve stated before – I do not pass in person. Don’t let my pictures fool you. In two dimensional photos where I have more control over things such as lighting and the angle in which I’m viewed, it’s a lot easier to appear passable. In person, angle, depth perception, and less than ideal lighting conditions easily reveal my feminine shortcomings.

Just friends, not lovers
When in girl-mode, my wife prefers I behave like a friend, rather than romantic love interest. It’s understandable, as it should draw less attention in public that way. Even so, my arm kept finding its way around her shoulder somehow. Muscle memory, old habit, or subconscious need, it was quite difficult to keep from showing romantic affection for her while we were out. I never realized how automatic (and frequent) my spousal public shows of affection are, nor did I expect it to be so difficult to refrain.

Mrs. H. did a good job of helping me feel more comfortable out in public. She coached me on “feminine shopping behavior”, mannerisms, posture, and appropriate facial expressions. Yes, facial expression is an important point to her, and I agree. As a not so youthful genetic male, my face doesn’t look very feminine on its own – even when coated with gobs of makeup, carefully applied so as not to appear like “gobs of makeup”. I have to try to keep a “perky” look on my face, which includes a hint of smile, that does not appear to be a full-out smile. Walking around with a constant smile on my face would just be weird. It was tricky, but I did my best to pull it off.

One thing that was no different from any other shopping experience with my wife was that I ended up carrying all the clothing items picked out as we browsed. As a loving spouse, in guy-mode or en femme, I am always happy to do so.

Blending in… more or less
My attention was a bit divided. My wife kept trying to get me to behave and act “naturally” (which included browsing through clothes), but I couldn’t help but try to look at each and every face around me for signs of being “read”. Most people seemed to be completely unaware, which is exactly what I wanted. That was the point in dressing in “fem-drab”. So long as people don’t look directly at me, and there was little reason for them to, I would remain just another body in the crowd.

I did not go completely unnoticed, however. As my eyes scanned about, I did notice a handful of people who appeared to have read me. There were at least a few occasions in which people reacted directly to my presence.

Deer in the headlights
Shortly after entering the mall, in one of the main hallways, two teen boys (maybe early 20-somethings) walked in our direction while conversing with each other. Our eyes met briefly. A few yards away, their conversation stopped abruptly and I got a rather obvious look of surprise. Just after passing by them, I couldn’t help but laugh out loud. Their eyes open wide, almost popping out of their heads, and jaws hanging open in surprise, was rather humorous.

Nice boots
In the clothing store that we spent most of our time browsing (it had clothing styles we both enjoyed), I was approached twice. A young male sales associate came up to me and commented on how he liked my boots as he showed me his own boots… women’s boots. Footwear was his only “female” attire as far as I could tell. He read me, and we read him as well, though not as a transgender in his case. He was an effeminate, stylish, gay man. With only one or two exceptions, I’ve always clicked well socially with gay men and women. They’re pretty open-minded and cool, or at least those I’ve had the pleasure of knowing over the years.

I did not actually talk to the sales associate because Mrs. H. jumped in and began chatting with him, believing he was commenting on her boots and not mine. I stood by and smiled while they talked for a minute or two. There was some hesitancy on my part to chat with strangers on this day, which I’ll explain later. Even though I didn’t participate in the brief conversation, it was still a cool experience. He knew I was trans and was genuinely welcoming to me – perhaps more so because of it. How I wish that could be the case with everyone, or at least the majority.

Excuse me, ‘miss’…
After our shopping in this store was concluded, Mrs. H. and I quietly conversed with each other while waiting in the rather long, slow moving check out line that extended back some distance. After some time, another shopper approached me and asked me for some assistance. She was in her late 50′s, I’d guess.

“Could you tell me what the price on this is? I forgot my glasses and can’t read the tag.” “Seriously? That’s her approach?”, I thought to myself. I almost busted out laughing… again. It was a rather obvious attempt to get me to speak so she could confirm whether or not I was a “real” woman. The moment seemed like it was ripped right out of a Seinfeld episode. Smiling larger than life and trying not to laugh, I leaned over to look at the price tag. Just then, Mrs. H. intervened and “helped” the woman read the price tag. My wife’s intent was to “come to my rescue” and prevent a potentially uncomfortable moment. I love her so much for that. Had she not been there, I would have “played along” and probably gotten “probed” a bit further by this curious woman. Her polite, if obvious, approach to “reading” (or confirming) me was amusing and probably well intentioned but I knew it was best to not converse with people on this day. It might have been a great opportunity to engage in a potentially educational conversation, but I was filled with a mix of nervous energy and adrenaline and very much off my game.

An alarming reaction
Shopping bags in hand, Mrs. H. and I slowly made our way through the mall’s large hallways. As we walked and chatted, my eyes continued scanning about looking for signs of being read. Most people seemed not to notice, and that was very pleasing.

At one point, my eyes met the eyes of an oncoming man who was walking in our direction with his young daughter. He was about 5′ 6″ (noticeably shorter than I), very thin, and probably in his mid 30′s. I looked away to be polite. A moment later, I looked back to find him still starring directly at me with a rather odd look on his face. He pulled his young daughter close to him, pressing her against his body, as if to protect her from imminent danger, and quickly altered direction into the nearest store entrance. Our eyes remained locked for several seconds during his “escape”. The “odd look” on his face appeared to be that of fear, perhaps anger. I’ve gotten nasty looks from people before, but never the look of fear, if that was what he experienced.

I asked my wife if she caught his reaction, but she was looking in another direction. I explained what I saw – a worried man attempting to “protect” his young daughter from… well, me. Mrs. H. tried to convince me that I misinterpreted things because I was nervous. Well aware of my own nerves, I disagreed.

It took some time, but I think I figured out what really took place. The over-protective father probably did experience a genuine sense of fear. The fear was not of me however, but rather of his own daughter. More accurately, he likely feared having to explain what I am (as a transgender) to his daughter had she gotten a look at me.

I understand his discomfort in context with where much of society currently sits with things. Even so, his reaction was cowardly and unnecessary. Children look up to their parents for guidance. If they sense discomfort in their parents about something, they will in turn learn to become uncomfortable about it themselves. My own parents were very uncomfortable answering certain questions when I was a child. Consequently, I “learned” that these things were just “wrong” – even to simply inquire about. Looking back, there was nothing wrong with most of the things that made my parents uncomfortable. I’ve made it a point to remind and embarrass them about it in recent years, mainly in jest.

It is sad that certain realities, perfectly natural and quite harmless, are still taught to be immoral or flat-out “wrong” in the eyes of impressionable children. This is a topic best suited for another concentrated discussion… or many discussions, however.

An interesting learning experience
Our mall shopping concluded, Mrs. H. picked up a few tops and a dress. A single new miniskirt was in my bag – not exactly much of a wardrobe expansion, but finding things in my size (mainly tops), AND in styles/colors that I like, is no easy task. In addition, I was quite distracted with my “people watching”.

For the record, I quickly changed into my new miniskirt upon arriving home. I couldn’t get out of those pants fast enough. It felt so good to feel “normal” again. I am literally laughing as I share this, but it’s true. The skirt looked very nice on me, too. Again, my apologies for not having photos.

Although it was a good learning experience, I’m not pleased with many aspects of the outing – mainly how it felt (or how I felt during it). My attempt at blending in by dressing exactly how I do not like to dress did work to some extent. The cost of blending in was that I didn’t feel very feminine, even under all that makeup and completely in “women’s” clothing. I didn’t feel like myself. It almost felt like I was “playing dress-up” (“dress-down”, in this case) or wearing a costume. Have you ever felt really awkward or “not right” because you dislike what you’re wearing, regardless of gender expressed?

Feminine vocalization issues
According to Mrs. H., I was unable to produce my feminine voice properly, which she noted as we quietly talked to each other while shopping. That was, to some extent, why I was hesitant to engage in conversation with anyone. I practiced my feminine vocal exercises for about 10 minutes in the car on the way there. My wife got a big kick out of that, and even I am laughing as I reflect. Maybe the vocal exercises were not long enough, or perhaps I was simply not feeling enough like myself to properly feminize my voice. Many crossdressers do not try to hide their male voice, however as Gabrielle, I do not aim to be a “crossdresser”, but rather a trans-woman, if only part time. I’d rather not get into the “labels” and “terminology” debate right now, though. This write-up is already triple its intended target length.

Analysis, Mr. Spock
I’ve got a ways to go yet, in terms of blending, acting “naturally” and feeling comfortable out in the “wild”. A controlled environment, such as a planned gathering where I know people or have a specific purpose, is a lot easier for me right now. Life is a growth process and this part of my growth has been stunted for a long time. I’m playing catch-up, though it’s moving at a very slow pace – mainly due to lack of time and opportunity to get out and grow. My own feelings and emotions are under constant psychological self-analysis. This trip out gave me a lot of good data to sift through, odd as that may sound. It’s something we all do, although I sometimes speak about it in direct analytical terms.

What’s your story?
For those of you who are more advanced than I when it comes to public self-expression, what have you discovered in terms of successfully blending in? Those of you who have yet to venture out in public, what keeps you from doing so? Please take a moment to share experiences, thoughts and ideas.

Update:
Click the thumbnail to see how I look in pants. The outfit in this photo is different than when I went out shopping with my wife, but from the waste down, including the boots, that is what I wore. I’m not a fan of wearing pants, but I don’t look too bad in them. Honestly, I look a lot better in these kind of pants than a lot of genetic women half my age who squeeze into them… but of course, I have to exercise my fit little butt off to achieve it.

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

It’s been one year since the opening first post was made here on myCDlife.com. This “one year” post happens to be the 111th published to date, which fits in nicely with the “one” theme.

If curiosity piques interest enough to look back at some of the early posts, you will notice that many of them were not crossdressing related. One of my initial ideas was to simply share with visitors, the life of a crossdresser (me), specifically to illustrate the fact that, for the most part, trans-life isn’t very different than the “norm”.

Being a crossdresser doesn’t mean that life is all about lipstick, fashion, heels, stockings and wearing dresses. I think there is a perception to many (non-trans folk) that this all crossdressers ever think and talk about. Although that may be the case for some, it is certainly not how it works in my life or the lives of several others I’ve gotten to know, including many who regularly blog about crossdressing. The trans-related posts drew more interest than the non, so I settled into a routine of concentrating more on that end of things over time.

Many of my original plans for this site were never realized, mainly due to lack of time and resources. Even so, I’m happy to have accomplishd at least some of my goals: educate visitors about the realities of crossdressing, make a positive difference in the lives of people who struggle with this aspect of their lives, share some of my own related struggles/stories, and have some fun along the way.

Having this online presence has allowed me the opportunity to interact and share ideas with some unique and interesting transgender people, from crossdressers to transsexuals. The diversity within the vast transgender spectrum is extensive and I’ve enjoyed learning about the wide array of differences while celebrating what we have in common. Although not as great in numbers, I’ve also had the pleasure of interacting with non-trans folk, too – mainly family and loved ones there of.

I don’t know what year two will hold for myCDlife.com. Even though I have trouble keeping up with things due to lack of personal time, I’d like to see it continue, if only on a limited basis (in terms of new content updates). There are more crossdressing myths to bust and countless other aspects & ideas to explore.

I’d like to thank everyone for visiting this site over the past year and hope you’ll continue to do so in the future. It’s been my pleasure and an honor to be your humble myCDlife.com hostess. Thank you so much for your time, attention, feedback, and sharing a little about yourself in return.

If you wouldn’t mind sharing, what have you enjoyed most about my offerings here? How did you discover myCDlife.com? Is there anything in particular you’d like to see more of? What would you change, if anything? Please take a moment or two to share.

I came across this in a local paper. It has not been doctored up. This is exactly how it appears in the full page ad. It clearly illustrates the evolution of man is, in fact, crossdressing… or so it is in the automotive business. Hey – it’s a start, right?

As crossdressing grows in popularity in the automotive business, it will also soon spread to other industries. The business world can be pretty cut throat, with a growing emphasis on the word “pretty”. It’s about time crossdressing entered the mix.

Suit-up, folks… er, make that, skirt-up if you want to climb that corporate ladder. The old school businessman in a suit and tie is going the way of the dinosaur. As they die-off and fall out of power, they’re quickly being replaced by smarter, more innovative people with much better taste in clothes. Make way for a new era of smart, sexy, stylish and powerful corporate leaders known as the businesstrans.

Of course, the ad in the paper refers not to crossdressing, but rather the rise of women in positions of power. Perhaps in time, the ‘businesstrans” will replace the businessman though. Many crossdressers already own their own business. I’ve been in touch with several personally. Of the ones I know, it is the man-side that takes care of the business end of things. Personal appearance still holds a lot of weight in the business world, and today, the prettier side of things is still less attractive in the eyes of many would-be clients. That will change in time though.

For those of you who fall under the category of “businesstrans”, do you take care of (face-to-face) business in guy-mode, or en femme? Where do you see the “evolution of man” going in the business world? I know where I’d my own (business) evolution to go. Whether or not I’m smart enough to pull it off has yet to be determined. What’s in your business future when it comes to gender expression or just feminine fashion?