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Jessie's Path

"A true story of the Path that Jessie took."

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One’s path in life has three primary sections. The first one is what made a person who they are. Everything from their parent’s genetics, to how they were raised, the environment they grew up in, and any uncontrollable outside influences causing a life changing event. The second section of the path is what we see, feel, hear, taste, and touch at this very moment in time. It is a collection of fleeting moments that may or may not influence us immediately, but could have a big impact on us sometime in the future. The final section is the path ahead. This path is filled with unknowns and uncertainties, some of which leads to fear because of the unknown. Other parts of this path will lead to key decision points where we have to decide if we want to take the left fork or right fork. Once that decision is made, there is never a chance to explore the other path.

One of my friends recently texted me a very unique comment that immediately caused concern. It was a simple, “It’s Steve (name changed to protect identity)”. Followed by, “Still Steve. For now at least”. My first thought was that a friend of mine who I had known for over thirty years (since we were in sixth grade) was going to do something rash in his life. When I called him, I was fully expecting to hear his last words, and there was nothing I could do to save him.

But that was not the case. Steve told me that he is transgendered. I had a little bit of a surprise in my voice, when I said “Really?”, but other than that, it was more like questions entered into my mind. “How did you find out? When did you start dressing up in women’s clothes? Did your wife ever catch you dressing up? How far down the transgender spectrum do you think you’ll go?” So many questions went through my mind with that phone call. After a while, I told him that I support him and will always be there for him.

A week later, I texted him and asked if he was free on the weekend. His reply was that he had potential plans on Saturday but will call if things change. Just before Saturday, we got into a weird Facebook discussion on current politics. We are both on opposite sides of the political spectrum, so obviously we didn’t see eye to eye on something. I replied with a very curt tone on a slightly different political topic. It was implying that I was anti LGBT rights, which stung me, so I replied back. Saturday came and no reply from Steve. I texted him only to find out that he had solid plans on Saturday. We agreed to get together at my house on Sunday.

Remember what I had stated about the path of life? That the future path is shaped by the decisions we make? Well little did I know that something significant was going to happen on Sunday.

My friend Steve came over that fateful Sunday. He was dressed up in plain woman’s clothing, nothing fancy, provocative, or outlandish. He introduced me to Jennifer or “Jen”. After a brief conversation about Jen, we sat down and started talking politics and its impact on LGBT. Kind of interesting that we immediately got into that, but obviously we needed to clear the air. She even commented to me how she didn’t think she could be friends with me because we were so different.

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That was my decision point.

I said, “Jen, I really don’t think we are all that different.” I proceeded to lift my jean covered leg up to the couch. Now, not expecting what was going to happen, it would be very easy to miss one important detail about my feet. I wasn’t wearing socks. I was wearing a pair of my crotchless black opaque tights. I not so subtlety pointed to my foot. “Do you see it?”

With a stunned look, Jen exclaimed, “No way!”

My foot was out. A foot out of the closet.

Through the stretched out fabric on the tights, you could just barely see my pink colored toe-nails.

No one close to me knew of my secret love of anything womanly. Like so many before me, I was in the closet, afraid to show my true self to others. However, just like Jen, I shared a love for women’s clothing. Just like Jen, I played the girl when having a choice playing games. Just like Jen, the desire was there at a young age. Just like Jen, countless buy and purge cycles. I was just like Jen.

I went into my room and grabbed my corset and my breast forms. With a big smile on my face, I brought them in for Jen to see. Next came my make-up box and my red high heels. Jen was smiling at her friend who started coming out of the closet.

We tried to watch the football game, but it was filled with conversation of the path we already walked. As we discussed our past desires to dress in women’s clothing, it then gravitated toward Jen coming out to various old friends in our lives. But what most struck me was Jen’s happiness and giddiness of how I chose the path. It was the path of showing her my secret.

I excused myself and walked into the bathroom. I looked in the mirror and pondered today’s journey. All I saw before me was a reflection of myself in the mirror with a big smile on my face. I took another step down the path. I took off my jeans and t-shirt and placed them on the floor. All that I was wearing at this point was a pair of mauve colored women’s bikini panties and my black opaque crotchless panties. I placed my black five inch high heels on my jeans so Jen would not hear the distinct clicking of the heels hitting the floor. I placed my foot into one of the heels and carefully put it on. I repeated it with my right foot but with care that I did not step down on the tile.

Next came my bra and breast forms. I made sure that they aligned and looked as natural as possible. After that, I carefully put on my corset. It is a steel boned corset which really gave me the womanly shape I desired. After securing the small latches, I started pulling on the strings to tighten the corset up. After I got the corset as tight as possible, I tied it up and tucked the lace inside. Next I put on my leopard dress. It is by far my favorite dress that I own. Finally, I placed a woman’s wig on my head, teased the hair a little and opened up the door.

I took my first step down a new path. As I stepped out of the bathroom, I saw Jen look at me.

“Jen. Meet Jessie.”

I walked into the living room in my high-heels and sat down next to Jen on the couch. It was an amazing two hours talking as Jen and Jessie.

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Written by JessieCD
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