Hello my name is Skyler, and I’m transgender

Readers beware. This article describes many aspects of my journey so far–some of which may be uncomfortable. I figured if I’m going to share my story, I might as well tell it all.

It all started when I was very young. I don’t recall any memories before age five. My grandmother passed away in November if 1995 and it’s about the earliest I remember. I do have a particular memory from the months prior; one that resonates quite well. It was Halloween 1995 and it was my first realization that I was “different.” I just didn’t understand why I couldn’t be Ariel for Halloween. Granted, I never expressed my feelings to my parents, but in my head, I was always in confusion. Why do I have to dress like the boys? The clothes are uncomfortable. Why can’t I wear what I want?

Growing up, I was the oldest of four kids. I was supposed to be the role model for my three younger brothers. Set the example, lead the way, and show them how to be little boys. The truth of the matter, I looked up to them. I had no idea what I was doing as a boy. I didn’t particularly do well with girls, I couldn’t play sports to save my life, oh, and I was more interested in girl’s clothes than in boy’s clothes. When I was around 8, we were playing in my parent’s attic and found all the old toys from when they were our age. My brothers were fascinated by the superhero action figures and toy trucks. While I enjoyed playing with them, I was drawn to the Barbie stewardess set and doll house. That’s what I wanted to play with. Once again, I hid those feelings. You’re the role model, the older brother who needed to set an example.

As we grew up, I did everything my brothers did. They played sports; I played sports, sort of. More specifically, they played and I was a bench warmer. I still hadn’t found my niche. No matter what I tried, I never liked it. I was more inclined to sit down at the piano or pull open my sketch pad.

During high school, I hit my dark days, round one. It was the first time in my life that I truly started accepting myself for who I was. I grew my hair out to about shoulder length, painted my nails (black or gray to keep with the excuse that I was a rebellious teen). I wore girl’s jeans and tight tops, and my family never once questioned it. After school, I would find a reason to stay late and go to the mall with the girls. I’d fix my hair into something more feminine, do my makeup and we’d be off. I came so close to coming out to my family and friends then, but I was afraid of rejection. There was a point when I really thought I would say something, but then it happened.

When I was 16, we had a family friend come out as Trans. My parents and family reacted in the worst way possible, they exiled her. It was hard to hear them call her a pervert, disgusting, etc. While I silently applauded her courage and desire to change her life, I understood my parents might never give me a chance to express my own feelings. I had to follow their lead in order to avoid creating tension between us. It still bothers me today; though I never ridiculed her, I also never stood up for her. It’s been 12 years since then, and I’m still dealing with the shock at how my family treated her.

This event put me into a tailspin. I shut down and locked everyone and everything out. I blamed others for my mood swings and outbursts. I eventually cut some really close friends out of my life. There were multiple times throughout high school that I contemplated suicide. I turned to self harm. That pain was a welcome release from the pain of my day to day life. I gave myself piercings because that pain was comforting in a way. Looking back now, I see that it wasn’t brightest idea.

In spite of all of my troubles, I graduated in the top 10% of my class, landing a scholarship to one of the best technical schools in the country. I had it made… but I still didn’t feel like it. I spent a couple years in school hating everything but the freedom it gave me. I could be Skyler whenever I wanted, which really, was all the time. The problem, I was constantly ridiculed and mocked. After suffering through two years of ridicule, I dropped out. I decided that I needed to make myself masculine to fit in with this overly, opinionated world.

During my manning up, I met a girl. She was great and stayed with me for six years, on and off. All the while, I hid this major secret from her. Through our relationship, I did a lot to make myself more masculine. During the first half of our relationship, I started an auto repair shop with a friend, and I was also the military reserves. I grew the denial beard and got a plethora of denial tattoos (still releasing my inner pain with the external pain of the tattoo gun.) Our relationship ended a few years later. Soon, I reached rock bottom. I was broke, on the edge of eviction from my townhome, and was the last person working at a failing business. Life was slipping through my fingers at an alarming rate. I was suicidal and my depression was uncontrollable. Between April and September, I attempted suicide, twice. When it couldn’t get any worse, my ex came back into my life. The parts of my life still standing came crashing down around me.

She called from outside my shop, saying that she needed to talk in person. I’d spent all day smoking and drinking. I wasn’t in any shape to talk, but she had me cornered. I let her in and she told me that after we broke up, she found out that she was pregnant. She had come directly to my shop after her doctor’s office appointment, where she found out that she had suffered a miscarriage. I was already planning another suicide attempt, but this set it in stone. It would happen that night.

I went into my office and wrote down what was sure to be my last words. I stared down the barrel of a .380 and questioned my existence. Why is it that I could never admit to who I was? Why did I hide for so long that I am now driven to this? I found a small sliver of hope; I stopped everything, unloaded the gun, locked it in my safe, and drove to the hospital. I checked myself into inpatient psychiatric care and took the first steps toward accepting me. After two months in therapy, I thought it was too much and quit.

After all that had happened, I felt it best if I left town. Being around all of the reminders of my past was too much. I picked up everything and moved to the other side of the state, starting a career in construction, believing I’d finally found something super manly that would wash this side of me completely away.

Uh, no. Not quite.

Instead, my feelings grew stronger. I began collecting a wardrobe again and wore what I wanted in private, when my now fiancé wasn’t home. It took me until this year to finally admit to her how I feel inside. I quit my construction job after almost 4 years and started a more comfortable desk job. On top of everything, our son was born in August of last year.

Recently, I returned to therapy, and just last week, I started coming out to friends as transgender. So far, those that I’ve told have accepted me; one in particular has encouraged me to dress how I want when we hang out or go out together. The old fear still lies in the same place where it did when I was 16—with my family. They aren’t shy about calling us perverts, fags, or immoral. It terrifies me that they might cut me, my soon to be wife, and our son out of their lives. Worse, they may claim I’m unstable and can’t raise my son. I’m not looking forward to telling them, but it needs to happen eventually. When; who knows. How; haven’t got a clue. What I do know is that eventually they will need to know I’m now their daughter, sister, niece, or granddaughter.

I plan to start HRT as soon as possible. Following a couple years of HRT, I’ll likely pursue a full transition. This is only the start of my transition and of my story. It will be updated as I progress. This is an extensive story, but I hope some may find commonalities with their own and realize they’re not alone. Don’t let others get you down, and remember, you’re beautiful just the way you are.

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Skyler Anne

Scared, nervous and confused I guess sums it up. I’m Skyler. I’m 28 and from Chicago. I still live my life as a male. However, I have felt a strong sense of being “different” since I was roughly 5. Maybe sooner, but that’s the first I remember feeling the way I do. I’ve spent the last 28 years covering myself up. I’m finally to the point of “I can’t do this any longer.” I realized recently where my lifetime of depression and other psychological problems have stemmed from. I enrolled myself in therapy to help better cope with my feelings and emotions and to help better describe these feelings to family and friends. Specially my fiancé. She has been incredibly supportive, however used a line that stuck in me like a dagger. “I’m fine with you wearing what your comfortable in, just so long as you don’t want a sex change or something.” Hurt? Yes. But I understand her view. She wants to marry her husband. Not have a wife. She doesn’t understand exactly the thoughts and emotions I deal with on a daily basis but how could she? Anyway, I digress. I’ve been a member on crossdress heaven for a few months and have made some connections there, I just feel like most of the people on there see what they’re doing as a hobby. I wanted to come here to get more meaningful conversations from other girls who have gone through this and can help me find my path through this journey. I am an open book and am open to chatting any time. I’ll be around here as often as possible.

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Sophie BourneBrenda LeighMarcy HoseMeeka HawkinsBobi Hegony Recent comment authors
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Sophie Bourne

Hello Skyler. Such a very moving story, and thank you for sharing. Made me cry actually. The part about “manning up” after uni, when you knew you didn’t want to, but felt you had to… And then almost ending your beautiful, precious life… And I whispered “Me too…” And I thought: Skyler, you have been very, very brave. I do hope so much that you are still here. I do so hope that the love with your fiance was strong enough since you wrote. I do so hope that your child will know both his mums, as they both sound… Read more »

Breanna Leigh

Hi Skyler, You and I spoke a couple times about a year ago on CDH and I must say you were an inspiration for me at the time. You were fighting to be yourself against some tough odds at a time I was waking to my own truth. I admired your courage and strength doubting my own ability to come forward as a trans woman and it was stories like yours that finally inspired me to come out. I progressed very quickly beginning to CD just a year ago after pretending to be a manly man for twenty years. By… Read more »

Bobi Hegony

Skyler, I’m with you. I recently told my wife of the difficulty I have with living as a man, my desire/ need to banish the opression of our society and behave and dress as I want. It is a huge relief to have told her though she wants me as I present – as a man. I know if we ever broke up I would approach transitioning seriously, but I don’t want to break up. I am slowly developing myself. My style is changing as are my interests. I’m enjoying the process. I am in my 50s, with 3 boys… Read more »

Frank Rizzo

Very beautiful

Nolene Venus

Hi skyler i feel the same as you im starting hrt very soon i need to come out and tell wife and family but finding that so hard to do love nolene

Meeka Hawkins

I feel your pain Sister and I too have looked down the barrel into the darkness. That was years ago and today I’m in therapy and on hrt. I haven’t come out yet but that day is quickly coming. Some days all you can do is focus on getting through today towards a better tomorrow.

Marcy Hose

You said, I am about to make the plunge myself. I some how managed to stay very good friends with my wife/girlfriend, kindred spirits, hell I don’t know but we love each other no matter what or who. It’s not sexual, it’s not selfish, it’s just us. I can honestly say I love that she has a boyfriend. I am excited for her and she’s happy and know the real me, it’s crazy but it’s true.

Meeka Hawkins

Hi Marcy. You are very fortunate to still have her in your life. Mine have all disappeared from my life. I am making new friends and hope to have someone full time in my life someday. It’s either that or be the local old cat lady in the neighborhood. Still not a bad life.

Marcy Hose

Sometimes it feels like I am headed that way myself. Thank you for the comment. I needed that.

CC Webb
Active Member

Skyler, your perseverance through it all is astounding. I was the second of two brothers and to this day still look up to him, yet he calls himself the blacksheep of the family. The incredible strain of expectation on the oldest must have been like a straight jacket meant to keep you in line, yet you found a way to express yourself from within. That takes a courage and strength that most never even come close to realizing in themselves. You are more amazing than you may know and you have my admiration. As for them, I’m often amazed at… Read more »

Sabrina MacTavish

Very well put!

angel angelica
angel angelica

oh sjyler i know all those painful memories,hang in there sister.

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