Dear Gabi, I’m a Crossdresser and Don’t Understand Myself

Dear Gabi,

My name is Casey. I’m an 18 year old male who enjoys cross dressing but is very secretive about it. I am straight. I have not told many people, and don’t get an opportunity to do it as often as I like. I have a lot of questions and stuff to get off my chest.

I have only come out to four people. I came out to my parents when I was in the sixth grade, because I was going through puberty and didn’t understand my brain. They were both fine with it and didn’t love me any less. However I think as far as they’re concerned I’ve stopped cross dressing. We haven’t talked about it since. I shouldn’t have a problem with it because they are two of the most loving, liberal, open minded people I know and every day I’m grateful that they’re my parents.

I openly describe myself to people as flamboyant, and when I say it, I say it proudly. I am proud that I do all the no-no’s of being a manly man. I love my girly side, I just wish I could express it more. I suppose I get along better with girls (except for my best friend in the world who is a guy) and the ones I am friends with are open and loving. My two friends here at college would probably be fine with knowing I’m a cross dresser but I freeze whenever I even think about telling them. I’ve told two other people besides my parents. Purely by coincidence they were both girls who were struggling with their sexuality. One of them is now my best friend on campus, and we talk about the subject all the time.

What are some of the reasons that keep my from being myself? I suppose when you get down to it they’re that I’m worried about what my brothers will think, especially the oldest. He’s extremely bigoted when it comes to anything related to gay marriage. I don’t know how that happened because my parents are fine with gay marriage. My dad’s best friend is gay. While the third one probably isn’t against it, the youngest one is still very impressionable and I want to make sure he ends up more like his father than his oldest brother.

I go to school at a very conservative campus, to the point where it’s laughable. Our college is a Catholic institute (I’m not going into my religious views and i don’t want to say anything insulting) so they’re sort of nervous when it comes to anything LGBT related. Get this, we couldn’t do [the play] Hairspray because it featured a man in drag! Oh, grow up! You get the idea.

I don’t get myself. I’m flamboyant and goofy in real life. People even think that my best (guy) friend and I are a couple, mainly because it goes beyond bromance and we just love each other. We’re both straight oddly enough, but we’ve often said we’d have no problem marrying the other. So if I don’t care about people thinking I’m gay, why would I have a problem with them knowing I cross dress?

The other thing I find myself doing is putting up a front when I’m trying to attract and get to know girls. I start acting more tough and less flamboyant. I don’t try to, but it all happens subconsciously. I always find myself wondering, “if she knew, would she accept me?”

You seem very knowledgeable about this subject. I was wondering if you had any advice you could give me.

With great appreciation,


Gabrielle HermosaDear Casey,

You seem like such a beautiful person who has loving parents, great friends, and your whole life ahead of you. It’s not uncommon for people your age (or any age) to experience some confusion about their lives. So why all the feelings like something isn’t quite right?

The good news is that there’s absolutely nothing wrong with you at all, aside from misguided self-expectations and some over thinking. The bad news is that even after I pull back the curtain to expose how all this stuff works, it may take some time to quiet those troublesome, incessant thoughts. Pay close attention to what follows, be patient with yourself, and you’ll do just fine.

The wonders of cognitive dissonance
In each of the examples you offered, there was a clear pattern. Your personal realities are out of sync with your self-expectations, and you fear rejection from others if they knew the real you. Therefore you try to hide your feminine side behind a false masculine facade. In your mind, people will prefer the masculine act you put forth, to your true “flamboyant”, crossdressing self.

Human-invented conditions and expectations
Society starts conditioning us from the time we’re born. Boys get boy names. Girls get girl names. Boys get a blue room. Girls get pink. Boys get a football. Girls get a doll. Etc., etc. All the outward differences in gender, as decided by society, are driven into our heads repeatedly over our life. We’re conditioned to believe that people have to be either this way or that, and there is no in-between or alternative. When very common, normal human realities conflict with social “norms”, social expectations, naivety, peer pressure and mob mentality, those who feel a bit out of sync with (what appears to be) the world around them, question why and often develop insecurities.

Intellectualizing and the wrong conclusions
Everyone wants to be loved, accepted and viewed as desirable to others. People want to fit in. It’s human nature and very normal. Everyone is different, though. The degree in which people differ, from one to the next, or to the collective many, is where problems arise in the minds of those who register differences as potentially “bad” or undesirable. In this case, it is you who have taken note of one particular difference between yourself and those around you – your being a crossdresser.

Ok, so you’re a crossdresser, and those around you are not, or as far as you know. You also like to sing. What if the people in your life did not share your love of singing? That would be a difference, too. Of course, singing isn’t generally frowned upon by society as something “bad” or “wrong”. Crossdressing on the other hand, tends to be something most people know little to nothing about.

In the absence of any real knowledge or understanding, people often draw the wrong conclusions. They then compound and reinforce those wrong conclusions by intellectualizing how and why something is wrong/bad in conversation with others. This is where fear of the unknown mixes with the influential abilities of alpha-types, and soon mob mentality decides to fabricate whatever “reality” best suits the personal preferences of the influential, and consequently the easily influenced.

So at this point on the timeline, crossdressing is generally considered taboo, “wrong”, “bad”, whatever. Being a crossdresser, you’re self-conscious about what others might think and how they might treat you, if only they knew the real you. Timelines provide very interesting reminders of how wrong society has gotten it over the years, though. It wasn’t too long ago on the timeline of humanity, that people believed in killing “witches”, some races were inferior to others, and that the world was flat. False beliefs never alter actual reality, regardless of how many believe.

Lies, mind reading, story telling and insecurities
Unfortuantely, your fear of what others may think, if they were to discover you’re a crossdresser, has caused a very common reaction in your mind. In the absence of knowing what others think about your crossdressing, you’ve filled in the blanks with negatives, as if you could read their minds. The problem is, you’re not a mind reader. You’re projecting your own fears onto other people.

Conversely, the people you have come out to as a crossdresser have been very cool, accepting and understanding. I want you to pause for a moment and take note of the fear that people will not approve and not accept, in comparison to the reality that those who know the truth have been very accepting and love you.

Why all the fear of what others may think? Yeah, I know. Conservative surroundings, Bible misinterpretations, and mainly, that little voice in your head praying upon your own fear of the unknown.

Your thoughts are not reality, they’re just thoughts
That’s the real problem here. Your troubles do not reside in your surroundings, but rather in your own mind. There is not a single person on this planet that can fill you with more fear or insecurity than your own mind can. Who knows you better than you? You may feel confused or that you don’t understand yourself, but in reality the confusion lies within what I mentioned before: Your personal realities are out of sync with your personal self-expectations (aka: cognitive dissonance). Rather than accept that this just who you are, which includes being a male with a very strong feminine side and a crossdresser, you’ve been mentally beating yourself up about it.

The narrator in your head; that inner-voice you mistake for being “you”, has been feeding you lies based upon your fears. Because your mind has access to the sum of all your knowledge, life experiences, fears and insecurities, it can spin tall tales of gloom and doom that seem absolutely real to you. It is a form of insanity that most people suffer from or have suffered from at one time, myself included.

Fear is a lie
Whenever you experience fear about something you’re thinking, it’s always a lie. The thoughts aren’t real. Your mind has simply fabricated a story; a little mental movie of some hypothetical situation that does not exist. Then stress, anxiety and insecurities set in, and you begin senselessly questioning yourself.

Mindfulness is the key
Be mindful of and observe your thoughts, but do not believe them as reality. They’re just your mind’s intellectualizing and processing of ideas. Your mind is a tool. It’s there for you to use and help solve problems as needed. It’s not there to create problems, or the illusion there of. Do not allow yourself to become a tool to your mind. For the record, most people do just that. This is definitely one area you most certainly do NOT want to be in the majority!

You’re not as different as you think
How different are you, really? Let’s examine your point of “putting up a front when trying to attract and get to know girls.”

Most, if not all people, who are attempting to enter a romantic relationship, put forth an act that they believe will be found most desirable by their love interest. People go out of their way to look more attractive, be on their best behavior, and embody whatever it is they believe will win over their love. As a relationship grows and evolves, it becomes harder to keep up the act, and soon the honeymoon period is over. People slowly start to behave more like their true selves with each other. Expectations go unmet because their act was just an act to begin with. Conflict arises, etc.

Bet you already know
Isn’t your “acting more tough”, just an act, like any non-crossdressing man might attempt to put forth while trying to impress the ladies? How, exactly, is this any different from what a zillion other people do? It isn’t. You just think it’s different because that voice in your head has you convinced that being a crossdresser somehow makes it so. Remember what I told you about your thoughts. They’re not reality! Putting on an act to impress someone is universal and not related to, or in any way unique to any form of transgenderism. I bet you already know this to be true on some level, but those pesky little fear-laced thoughts and insecurities have clouded your mind. I hope this has offered some clarity.

Don’t waste time on those who do not deserve it
There are people so filled with fear, it literally controls their life and how they live it. I call them “zombies” (not to be confused with rotting, walking dead beings who who have an appetite for brains). They’re not hard to spot. They’re the ones who always tell you how you should live your life and how you should behave and think, and then remind you of the consequences of not conforming to their ideas. They always have some kind of intellectual “justification” for their way of life and general actions. Their ideas and opinions are almost always passed off as “fact”, coming from some authority or higher power and not from them. Remember what I told you about that little voice in your head? These folks have allowed their own internal voice; their fear-filled ego, to control their lives. Do not allow them to control yours. They may seem friendly and charming at times, but be careful. Entering a debate with them often results in a pointless battle of wits that can’t be won because they’ve already decided they’re right and you’re wrong, and will consequently say whatever it takes to make you seem wrong. Their whole personal belief system and ego is at stake, so you have to be wrong as they cling for dear life to their false core beliefs. In other words, their world is still very flat and they like it that way, and don’t you DARE suggest otherwise! Just let them be, and minimize contact with them as much as possible.

People who do not love and accept you as you are, but rather place conditions on their acceptance of you, such as, “If you want me to accept you, then you have to change…” – these people just don’t matter. Brush them off. Don’t allow their misguided judgements to get under your skin. They’re the ones with the problem – NOT you. Leave them, and their problems, alone and move along. These are definitely not the droids you’re looking for!

People that matter
People who love and accept you as you are – a talented, beautiful person filled with endless potential, who has been blessed with the gift of femininity and is a crossdresser, these are the people who really matter. They are worthy of your love, attention and precious time. Time is so very precious as it seems to fly by so fast, and only speed up as you get older (or at least the perception of it does). Don’t waste your time seeking someone’s conditional love. Invest it in the hearts and lives of the people who matter; the people who love you, as you are, unconditionally. You will discover there are plenty of people who will indeed love you for who you are, too. You need only to allow them. In other words, stop putting up fronts so they can get to know and love the real you.

We all need our privacy
You don’t need to tell everyone in your life everything about yourself. Only share what you’re comfortable sharing, with those you feel comfortable sharing it with. When it doesn’t feel right to share, then don’t. Everyone has a right to privacy. Trust your feelings, not the voice in your head. There’s a difference. One way to tell is that thoughts (the voice in your head) often lead to confusion. Feeling something deep down, does not. Unless of course, you attempt to intellectualize the feeling, as mentioned.

Be good to yourself!
There’s nothing wrong with you. You’ve simply been over-thinking and drawing the wrong conclusions. Stop over-thinking and get into what really matters in life: living, learning, loving, growing, exploring and enjoying it! If the confusion or uncertainty creeps back in, visit this page again, read-read-READ, and burn off that blinding mental fog. The concepts here (in this article, and most of the site) are universal. Only the particulars are unique from person to person.

Be your beautiful, unique, feminine self! Make no apologies for who you are. Carry yourself with pride. Respect yourself and others, and people will show you respect, too.

Love and best wishes! :)

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6 thoughts on “Dear Gabi, I’m a Crossdresser and Don’t Understand Myself”

  1. I am a closet cross dresser and have been for many years on and off. I am 50 years old. I seem to want to dress up more then ever but my 2 oldest children still live at home. so it’s hard to dress up. I love to dress up all the way, pad, nylons, bra, dress, make up, perfume, jewelry, heels. When I do have the chance to dress up I feel 100% stress free but my wife will not see me dressed up. How can I get her to understand why I dress up pretty when I do. I would just like to sit and watch TV with her as a female and be me. But she will not let me sit in the same room with her? I just want to be me and be free while I can. I would talk to her a whole lot better as in how I feel when dressed as a female, why? What do I feel when dressed up. This doesn’t bother me any. I feel like myself, but it bothers her. How can I get her to have it not bother her. I buy my own clothing, perfume, jewelry, make up, and pad and nylons and bra’s.

    1. Hi Lucinda, thanks for sharing. :) I’m sorry to hear your wife doesn’t understand and is bothered by your crossdressing. This scenario plays out with a lot of crossdressers and it really saddens me. From my own personal interactions with others, this seems to be almost exclusively limited to those who did not divulge their transgender status with their romantic interest prior to marriage, and/or those who have chosen to remain with their love interest, prior to or without plans of marriage, because they feel it would be too painful to separate. For the record, I did not come out to my own wife about my transgenderism until after 13 years of marriage.

      Education is the best route to take, in terms of opening up your wife’s mind a little. Most people know little to nothing about how crossdressing/transgenderism really works. She may be filled with all the negative cliches, misconceptions and flat out lies that are perpetuated throughout society. Given your understanding of your own wife, monitor her for a time when she seems most open to a dialogue about these things. Make sure you’ve done your homework and are prepared for her questions. If she is resistant to the discussion, don’t push it. Leave the topic alone and try again at a later time, again – when she is a state when she may be most open to discussing.

      Some women will simply never be open to, or accepting of anything less than a 100% masculine husband/boyfriend, regardless of how much they understand crossdressing, or one’s need to explore their femininity. Everyone is allowed their own personal preferences. If your wife falls into this category, you’ll probably be limited to expressing your feminine side on your own, without any participation from her. In every marriage, there are many things that each spouse does separate, without the other. This is normal.

      You might consider trying to discover a local group that gathers to offer each other support and the opportunity to socialize and share with other like-minded individuals. This may offer some relief, if you’re feeling kind of alone in all of this.

      Best of luck to you, Lucinda. Hang in there! :)

  2. thank you for your comment back. i will give it my best and go from there.thanks so much. in the mean time i will try to find a group in Niagara county and see what they have to offer. i would like to join one and go out as Lucinda and be my self and talk to other cross dressers.if you know one in my area feel free to email me the site.

  3. Casey there are a lot of us girls who like crossdressers but we’re not very well known because we get overrun by two groups 1. Women who like cis men or “manly men” and 2. Domme women who are into humiliation and forced feminization. The second one is a killer because you would think that you could find a kindred spirit on the internet (like fetlife) in terms of females and crossdressing males but of course you can’t because females and crossdressing males is always depicted as a sexual thing (not saying that shouldn’t I’m just saying there’s crossdressing out side of sex) and usually fraught with BDSM so it makes it nigh impossible to even date online with your peculiar interests. So we have no place to congregate and so no one finds us.

  4. More than one author has commented that the Internet allows new groups to form-with people who are otherwise too few and too scattered to find each other.

  5. I was considering Clarissa’s comments. Does the feminine side of CD males appeal? It occurred to me that might mean something in common between women and CD males, something not shared between women and cis-gender males.

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