Category Archives: Am I Transsexual?

Am I Transsexual – What Do I Fear?

This week we take a brief respite from our walk through my past and jump ahead many years to today. I was recently reading a passage in “True Selves – Understanding Transsexualism” that gave me a clearer picture of the emotional journey behind me, and the path stretching before me. For those of you following along – you diligent souls you! – this is from the section on page 112 that discusses the negative emotions and issues that transsexuals face.

The passage discusses the types of fear, anger, guilt, shame and poor self esteem that are commonly experienced by those who are transgendered. I recognized quite a few as intimate emotional companions, even while others (such as the many types of anger) I found difficult to relate to.

Emotions I’ve (Mostly) Come to Terms with

Shame is like a darkness that hangs over our heads, hiding the true light inside. For many many years I was ashamed of who I was and what I did. I had not dared to share my true self with another because I was deeply ashamed at how “sick” and “perverted” I was. By any measure – in society, in the church, or even how I felt inside – I was unworthy. I was a sinner who continued to live in sin despite knowing the “truth”. [If you’re struggling with being a transgendered Christian I encourage you to read this article ‘Crossdressing is a sin‘.

I crossdressed in private while clutching my dark secret close to my false bosom. Fear born of shame kept me cloistered and alone. Over the coming weeks I’ll share more of my journey, and how I overcame the shame and the fear that was it’s child. Realizing that I was not alone, and considering the blessings of being transgendered were vital ingredients to my growth. Words alone cannot give sufficient weight to how important it is to join a local transgender support group.

My shame is but a distant memory, and the fear I felt out in public has mostly been replaced with the joyous and easy calm of living as myself.

The See-saw of Self Esteem

For as long as I can remember I’ve had low self esteem. No doubt growing up a smart, overweight, socially challenged kid with a deep dark secret had something to do with it. Yet as long as I could take solace in the comforting glow of my computer screen this was manageable. After all, I was doing everything that was expected of me – I didn’t get into trouble, got good grades at school and left my parents undisturbed by my emotional distress.

This all changed when I left for college almost 750 miles away from home. The formula I had used so successfully in high school no longer worked. I had imagined college to be a haven for the intellectual elite where studious application to my coursework would ensure joy and prosperity. I quickly came to realize that the adoration of my Professors was irrelevant in the social world fueled by drunken revelry and frequent intimate engagement with members of the opposite sex.

Today I won’t regale you with my woefully inspirational tale of near suicide and joyous rebirth. My final years in college gave my self esteem a much needed boost, and the recent overcoming of transgender shame and fear of being out in public have fortified this further.

Yet I still play on the see-saw of self esteem. At times I’m assailed by negative self image (too tall, too fat, too masculine, …) or by the dastardly negative emotions you’ll hear about in a second that I’m still working through. Though continuing the see-saw metaphor further, I do feel as though much of the time there is a fat kid sitting across from me, leaving my self esteem dangling high in the air. Only on rare occasions does this kid summon enough strength to push himself off the ground and – momentarily – cause my self esteem to alight on the ground from which it came.

Fear

One of my favorite movies is The Lion King, and when I write about fear I can’t help but picture the scene where the hyenas mere mention of the name “Mufasa” causes shrieks of shuddering fear.

Yet I’ve found that in real life fear is not quite so humorous or easily recovered from. I had thought that once I overcame my fear of going out in public that I was done with fear, but three fears yet remain:

• Fear of losing employment and my livelihood
• Fear that I’ll never pass well enough to be accepted as a woman
• Fear of losing family and friends, and never having an emotionally intimate relationship again

I’ve come a long ways towards dealing with the first fear – the many tales of successful transitions in the software engineering field, and growing transgender support among large tech companies heartens me greatly. I’m also fortunate to be in a position where I’m able to save up enough to give myself some time should my employer prove to be less than generous in their transgender support.

The fear of never passing is harder for me. I’m confident that I could live successfully as a woman in society, yet I’m still wary of living as a transgender woman and having my genetic deficiency become obvious to anyone who gets to know me. I’m heartened by the times when I’m reverse read, and all the people I know have been extremely generous in their compliments. Yet brief encounters in public are different from lasting personal or professional relationships.

Objectively I’m taller and larger than most woman, and my voice can still use a fair amount of work. I know that diet, exercise, hormones, facial feminization surgery and femininity training can take me far, but I must live with my bone structure. I steel myself, knowing that my fear of never passing pales in comparison to the anguish I would endure living out the rest of my days in my male façade.

My greatest dread is living the lonely life of an outcast. Never able to find love or emotional intimacy again. Knowing my lovely wife will leave me after transition it’s difficult for me to understand how I could be happy without a deep relationship in my life. Though I hope against hope, it’s painful enough coming to terms with an eventual separation from the person I love most in the world. Losing her and the hope of ever being loved is crushing. At times I’ve even thought that the lack of human connection could cut deeper than living the rest of my life in a male lie. Yet the loss of all human connection is but a chance, and the torture of maleness a certainty.

And Finally Comes Guilt

Before my wife and I were married I told her that I was a crossdresser, that I was not gay, and that I had no intention of becoming a woman. This was the best truth I knew at the time, yet as I have discovered it was not the whole truth. Now with talk of transition I feel as though I have deceived her and tricked her into a life led astray, in a relationship that challenges her sexual identity and social acceptance. I feel guilty.

I try to console myself that her life with me has been more prosperous and abundant in experience that it would otherwise have been. Yet I pretend knowledge of fate in doing this, as her marriage to me may have excluded other fulfilling life paths for her.

While guilt can vex me, I know that how I handle the coming months will play a significant role in her future happiness. Wallowing in guilt not only doesn’t help, it distracts me from the care and compassion I need to cultivate. More often these days my rational mind is able to push aside the guilt and realize that the past is lived and the future is unknown. Today we get to decide what the past means, and how we’ll live in relation to that.

Dear reader, thank you for reading this far, and indulging me as I search inside my heart. My muse is spent for today, so it’s with warm wishes and blessings I pause – I shall parlay more with you in a while.

-Vanessa

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Am I Transsexual – The Terrible Teens

We resume the story with our intrepid heroine about to enter her teen years and experience the joy of her first period, breast growth and discovering boys. In your mind you should now hear the scratching sound as the DJ hastily lifts the needle off an old LP record just before the crowd turns around to stare. Our unfortunate heroine had none of those delights to look forward to, but rather the twin tyrannies of massive height expansion and needless hair growth in places entirely unbecoming.

Not that I knew what to expect at the time, or even that what was happening was wrong. It was just what everyone had told me was supposed to happen. I never had the sense of identifying strongly as a girl when young – though honestly never really felt that I fit in as a boy. I was too big to beat up, too shy to find and too smart to get into trouble at school.

The computer in my room was the perfect distraction from all my social and romantic ineptness – it was something I could understand even as I failed to understand myself and my relationship with others. As it turns out this distraction would pay a key part in my future welfare – but we’ve jumped to far ahead already…

My First Pair of Pantyhose

Crossdressing - My First Pair of Pantyhose

Crossdressing - My First Pair of Pantyhose

When I was 12 or 13 I found myself obsessed with the idea of purchasing and wearing my own pair of pantyhose. I have no idea why that would be a good idea, and tried for many weeks to push the thought from my mind. Yet after fighting the anticipation for so long I finally broke down, and found both the courage and opportunity to purchase my first pair of pantyhose.

My mom, brother and I were out shopping and I found occasion to “browse the shops by myself”. I told my mom I’d meet her back at the car in a while, and off I went. I made a beeline to a store I knew sold pantyhose, but that was on the other end of the shopping center from where my mom and brother were shopping. I could feel my heart drumming a tune of nervous ecstasy in my chest as I circled the aisle where the object of my obsession was kept.

After what seemed like hours of mustering my courage I approached the forbidden temple – and panicked! What size was I? Where was the color I was looking for? My pending sweat gave me little opportunity to think straight and I grabbed for the first pair I thought might have a chance of fitting, hastily made my way to the cashier and then out the store.

I had a few more minutes left, and I could wait no longer – off I rushed to the public bathroom to put on my new stockings, only to discover that they were gray! Damnit. I imagined my legs encased by sexy black stockings, not gray. Not gray! It was too late though, the deed was done and I was half naked in a bathroom stall trying to figure out how to put on pantyhose when someone banged on the door.

My heart dropped to the floor, “How could this be happening?!”. I was about to hastily scramble and get dressed – sans stockings – when the person identified themselves as the cleaner. I mumbled something and pulled those stockings on as fast as I was able to. Anxious beads of sweat were dripping down my face as I realized I was late meeting my mom, and rushed out to the car.

I could feel the pantyhose brushing against my pant legs, and in the car ride home I kept pushing down my socks to feel the texture of these divine encasings, riding the thrill of a desire achieved for the rest of the afternoon.

I’ve never felt such a heightened level of excitement at purchasing woman’s clothes before. Perhaps the energy was sexual, but this was before I had any experience or knowledge of what a sexual experience would entail. I was a naively innocent pre-pubescent boy who had re-discovered the wonderful world of femininity.

I won’t bore you with all the details as to how this pair of pantyhose caused me so much joy and tension. Wearing them, sleeping in them, stressing because I had to wash them without being discovered, finding a place to hide them so noone would discover them – as it turns out my calculator case was a fabulous hiding place :)

This was also the period where I began to derive sexual pleasure from woman’s clothes in one way or another. I won’t dwell on this, since just mentioning it has me blushing behind the luminescent screen of my laptop and anyway, this aspect is no longer an important part of my journey. I must admit eagerly looking forward to the time when the correct hormones are flowing through my body and such desires are under the controlling care of my mental and emotional faculties.

What do you recall about your first shopping experience for feminine finery?

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Am I Transsexual – In The Beginning

To get where you’re going it’s critical to know where you are, and often helpful to know where you’ve been. I must confess that much of my childhood is shrouded in the fog of memory, but I will strive to share those moments which shine brightest in my mind’s eye.

Crossdressing at Age Five

crossdressing-childhood.jpg

Crossdressing Childhood Dreams

My earliest memory of being different was when I was about five years old. I can remember it as if it was yesterday. I was besotted with the idea that I would wear my mother’s nightie to bed, yet knew that this desire was wrong. At such a tender age I have no idea how I knew that it would be frowned on, though I’ve heard other ladies say that they were similarly aware at a young age.

As much as a five year old could, I hatched a plan. Early in the evening I would smuggle my mom’s nightie from her room and hide it in the hallway closet. When she came to check on me before going to bed I would pretend to be sleeping, and then wait the torturously long while until my parents went to bed. Once they were soundly asleep I would sneak out to get the nightie, put it on and enjoy a night of bliss.

I must say that I’m quite surprised my plan went off without a hitch, and the next morning I changed back and reversed the “nightie from mom’s room to hallway closet” routine. I remember feelings of anticipation, excitement and then a deep abiding calm as I drifted off to sleep in her nightie.

Crossdressing in Bathing Suits

Still in early childhood I recall one day when a neighborhood girl came to play and then sleep over. In the afternoon sunshine I convinced her to trade bathing suits before running to the pool and jumping in. We bounced around in the water, and I remember loving every moment of it. I was scared that my mom would think something was amiss, yet delighted when she noticed our swap with what I can only imagine was a joyful laugh at the innocence of youth.

Later in the evening we tried to swap pajamas, but the lack of any expandable material in hers meant they didn’t fit. I grudgingly spent the night in my own PJs. My first blocked crossdressing moment, and transgender disappointment…

Crossdressing Party – It’s Allowed!

One of my fondest crossdressing memory came not too many years after the bathing suit event. I’m not sure how old I was, at best I can remember I was about nine or ten. A neighborhood girl (she who was generous with her bathing suit) was throwing a “Crossdressing Party” for her birthday. Everyone had to come crossdressed as the opposite gender, and I went as a Hawaiian hula girl, complete with grassy skirt and appropriate chest coverings.

I had died and gone to heaven and then died again and gone to heaven’s heaven. I still remember my mom telling my to “sway my hips” as we walked around their pool for the final judging. I ended up winning the prize for “best crossdressed boy” (the girls had a similar prize). I don’t recall how I acted after that, though I suspect a combination of hesitant joy and uninterested aloofness. Crossdressing was a fun thing to laugh about, not something to truly enjoy…

All I Want For Christmas

The last memory from my childhood was about a Christmas wish almost fulfilled. Like many youngsters we wrote letters to Santa asking him in our most polite and grateful way what we would like for Christmas. As was routine, we would write the letter, mom would read it and then we’d put it in an envelope and mail it to the North Pole.

I couldn’t have been much older than eleven, when I remember desperately wanting a dress for Christmas. Somehow I knew that telling my mom I wanted a dress was not a wise course of action. I had planned to wait until after she read my Christmas list and then discretely add “A Dress” at the end of the list before mailing it to Santa. After all, what harm could come if Santa brought me a dress? It would be Santa’s fault, not mine.

Unfortunately I chickened out at the last minute. I’m not sure why – perhaps I was afraid that Santa would tell my parents, or that mom would take one last look at the list before I could safely wrap it in an envelope. Whatever the reason, I remember a sense of lost opportunity that Christmas morning despite my abundance of gifts that included a really neat Capsela building kit [Hey, I've always been a geek in my feminine heart…]

The rest of my early childhood fades back into time. I vaguely remember times I sat longingly watching my mom applying makeup. Perhaps it was just an imagined fantasy, but I seem to recall her doing my hair or letting me play with her makeup. Things would only get more interesting when I took my first tentative steps into adolescence…

What memories do you have of your early crossdressing childhood?

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Am I Transsexual – Starting Therapy

transsexual-therapy.jpg

Transsexual Therapy

Even though I’ve been walking this path all my life I finally feel as though I’ve started my journey to womanhood. As many of you may know I recently began my transgender therapy. My aim is to validate that transitioning is right for me, and to find a partner who will assist me in the next steps along the journey (hormone therapy, going full time, and eventually the necessary surgical changes).

The beginning of therapy itself was a moment that my life took an irreversible turn – I was going to deal with my gender dysphoria one way or another. I had spent many years running from myself, exploring who I was, learning about the transgender community, discovering my feelings and testing my true nature.

After many years I have been able to overcome the shame I felt at being transgendered and the fear I felt at being myself out in the world. It’s these many years of learning, experience and testing that lead me to therapy almost completely certain that the next stanza in my life needs to be sung in soprano. Yet I know that I must temper my certainty with skepticism and allow my therapist to ask me the hard questions. I must seek new insights and self discovery. For if I don’t my experience through therapy will be poorer, and I would have missed a beautiful opportunity to validate myself.

For myself I find that sharing my experience in words with you lovely ladies is healing. The process of expressing my emotions, and the wonderful comments and insights you share have made my life richer up until now. I would be remiss if I didn’t share my rebirth as a woman with you as well. In advance I thank you for your gracious ear, your wise counsel and your continued readership.

Over the next few weeks and months I’ll share a new series I call “Am I Transsexual?”, where I seek to answer that question with more completeness and certainty than I’ve been able up until now. You’ll hear my journey, see my changes and get to join me on my experience into my true self. Rest assured that this more serious series of articles will be punctuated with great crossdressing tips, your crossdressing success stories, polls and many other goodies. Crossdresser Heaven has and always will be for everyone in the transgender community – across the gender spectrum – and for the loving (and at times shocked or confused) family and friends of a transgendered soul.

Before I begin I want to offer a disclaimer. This is my story, my journey. Everyone’s life song is unique and beautiful. There may be aspects of what I share that resonate with you and others you can’t relate to. This is not meant to be a map for navigating your transgender experience – as similar as we are, we are still different, and I highly encourage you to travel your journey along with a licensed professional. If any of this is helpful please let me know – your comments are a true blessing to me.

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