Member-only story

The Ultimate Obsession

JJ Hart
3 min readNov 12, 2023
Image from Brett Jordan on UnSplash

As I recall, the ultimate obsession I had with being feminine began with explorations into my Mom’s clothing and makeup. Once I started I couldn’t let it go.

Little did I know, I would need to follow quite the winding and rough path as I crossed the gender border from male to female. As soon as I conquered one of my goals and escaped my very dark and lonely closet another wall or barrier would crop up to challenge my obsession. An example would be how I imagined just improving my outward feminine appearance would be enough to help me live in the world as a transgender woman. All the process really did was set me up for other huge challenges.

Challenges such as how I would or ever could learn to communicate with other women in their world. Nothing in the process was easy and often terrifying. The old “no pain-no gain” saying proved to be all too true. Just attempting to modulate a feminine sounding voice to match my appearance was the ultimate challenge. Plus I needed to learn to always make eye contact with other women as we engaged in conversation. A simple statement saying I loved another woman’s ear-rings often proved to be the ice breaker I needed to survive in my new gender world.

Through it all, my male self was fighting me all the way. Every move I made to try to enable me to be more feminine was a problem to him. Deep down he knew he was…

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JJ Hart
JJ Hart

Written by JJ Hart

Thanks for stopping by! I am a married Transgender veteran author and blogger. I write in the hope of helping others with similar gender dysphoria

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