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Third Times the Charm: Why I De-Transitioned Twice (Before Transitioning Again)

If my love life was a rom-com, it would be titled “How to Lose a Girlfriend in 10 Days (or Less).” My journey to womanhood was unexpectedly intertwined with my romantic relationships, and let’s just say, I wasn’t exactly winning any awards for “Most Stable Partner.” But before you judge, know this: my path to transition was filled with detours. Like my questionable driving skills, I took the wrong off-ramp more times than I care to admit. I’m sure I’m not alone in crumbling under societal pressure, but I hope this article gives hope to anyone who feels like their hesitation around transitioning is a reflection of their worth. Believe me, my path was a wild one, but looking back, I wouldn’t change a thing.


For me, personally, the biggest reason I de-transitioned so many times was in a last ditch effort to save my romantic relationships. The first time, I came out of the closet after three years of being in a long term relationship. While driving back from a day at the beach, my ex turned to me and ‘innocently’ asked “if you could be born again as a woman, would you?” It was like an anime freeze frame— frozen, a large bead of sweat trickling down my face and then came the tears (seriously, crying and driving on the highway? Not ideal). I broke down and confessed what I thought was my deepest, darkest secret. Apparently, the foundation, blush, and mascara had outed me long before. Go figure.


She was supportive as she came to terms with what this might mean for the future she had envisioned for us together and during the next year I pursued bleeding my bank account dry as I bought every girly thing I had ever wanted. For this, I took a ‘fuck it’ approach, money will come and go but lasting baby trans memories of me decked out in all pink are forever (damn internet). Unfortunately in the end, I was dumped on valentines day. And no, the irony wasn’t lost on me.


Cue the self loathing! I felt so unbelievably guilty, like I had just single-handedly snuffed out the life from a beating heart. I hated myself for who I was, the pain it had caused and what it had cost me. So, I did what any [ir]rational self hating human would do and I blamed the girly things. They were temptations to suffering so I tossed it all, the thousands and thousands of dollars worth of euphoria, gone. Aaaand there I was needing to buy an entirely new wardrobe again (can you say cha-ching?). It wasn’t a total loss though, I kept the long hair and just swooped it back, I had Loki thing going on and honestly, being compared to a villainous troublemaker still resonates with me.


Fast forward a few months. My beard was back, and I was seeing someone new. I was upfront about identifying as trans but not wanting to transition — it just wasn’t for me (this is what my Tinder profile said and again, for the record, I genuinely believed this at the time). Before I knew it, I found myself in a relationship and was falling head over heels fast, now for most people this is wonderful, for me however, that meant I was comfortable and felt safe. What I didn’t expect was that feeling of safety (which albeit, was new) was fertile ground for my female side to grow, and boy, did she grow. Before I knew it mascara and she/ her pronouns were a staple in my everyday diet. Now, as you could imagine, this posed some challenges in a straight relationship. Kylie, once again, had pulled the ol’ switcheroo, and solidified my role as my own worst enemy, I pushed someone away that meant the literal world to me.


As you could again imagine, the self loathing came out for act two, I know a bit repetitive but I promise there's a happy ending coming up. I’ll fast forward a bit in fear of repeating myself. New relationship (definitely a rebound), new haircut, a bit of comfort, and boom — Kylie was back, crying and heartbroken, single again. I feared more than anything else at this point, that me transitioning meant that I would forever be unlovable (how fucked up is that??). I couldn’t do this to myself anymore, hang the whims of my life on the hope of being lovable. Luckily for me, the third time was the charm and my transition stuck.


Am I happy now? Heck yeah. Do I love myself? Most days; depends on how many sweet treats I’ve had and how much my tummy is giving me the middle finger (seriously, why do I do this to myself).

What I hope most from this article is that it gives hope to people who believe that transitioning is as simple as A to B. It’s not, it’s messy, it’s complex and more importantly it’s different for everyone- there’s no one right way to do it.


Voice is something that’s near and dear to my heart and if you’re looking for help to bring yours out, hit me up at https://www.voicebykylie.com/contact


Till’ next time,

Kylie

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