What It Was Like To Transition: A Trans Woman Explains

I transitioned when I was legally able to because I refused to deny myself happiness. Can you imagine living with a false identity for nearly two decades? Like Caitlyn, I knew at a young age that I was born into the wrong body. My parents were accepting and allowed me to wear girl's clothing, and never questioned my desire to play with Barbies. Though, outside of my family, no one understood me. It was tough being surrounded by small-minded people in Montana.

Hormone replacement therapy began right before I turned 18 years old. The thought of injecting myself was frightening, especially because I was unaware of what the outcome would be. I spent years fantasizing about my transition, and I feared disappointment. Within three months my masculine features softened and my breasts began to grow. I purchased my first bra from Urban Outfitters, and I wore it every single day.

I had my reassignment surgery, when I was 20 years old, in San Francisco. My surgeon appeared on a transgender segment on Oprah. She is also transgender, which caught my attention immediately. If anyone in the world understood what the surgery meant to me, it was her. I was sold after seeing her work on a beautiful America’s Next Top Model contestant. She was a miracle worker, and I became her patient a few months later.

Nothing could have prepared me for the pain that followed my surgery. It wasn’t a simple tuck and snip — vaginoplasty is intensive. My testicles had to be removed, and my penis was inverted into the likeness of a vagina. The healing process took nine months. I could hardly even walk for weeks, and I cringed at the thought of using the restroom.

My only escape from the pain was sleep, but even then I would wake up in agony. The pain faded once I was fully able to see my vagina for the first time. I held a mirror in between my legs for a closer view and stared in disbelief because it looked so natural. I touched myself for the first time, and chills shot through my body. It was life changing.

For the first time in my life, I felt like a complete woman. I was only missing a boyfriend. Meeting guys pre-op was difficult, but I was anxious to put my post-op confidence to the test. I had a thing for 20-something skater boys. My first few dates went well, until I dropped the "t" word.

At first, I was hesitant to sign up. I thought that who I used to be might work against me, but I decided to give it a shot. After joining, I was surprised to learn that a lot of men were supportive and encouraging of my position. My first "sugar daddy" was fascinated by my journey, and he thought I was more beautiful for being transgender. Unfortunately, not everyone was as receptive. One sugar daddy pretended to be accepting, and then slammed me against the wall when he decided that it wasn’t okay. I left his place in disbelief that night.

One sugar daddy nearly lost his marriage when his wife found out about me. She didn’t mind her husband using the website, but she did not approve of him dating ‘men’. She felt that I had tainted her husband and it weighed on me. Getting involved with a married man was bad enough, but being called a man hit home. I had longed for acceptance and I was crushed.

My experience as a "sugar baby" has taught me various lessons, and I am thankful for the opportunities it has presented. The generous men have gifted me with something more valuable than money, and that’s the confidence to see my beauty within.