Winning Life's Lottery

Recently I have been fighting my feelings and needs to be Leeanna. I have not had the opportunity for months now. It's been hard.

I have had requests to write some more of my usual "forced" sex stuff. I just can't It just won't come to me. This is what came out when I tried. Definitely not a sex story. Sorry.

Normal kinkiness and perversity will be resumed as soon as possible. I promise x

I have been dressing for as long as I remember. I only fully dressed as a woman when I moved out of my parents home for a few weeks, that was until I got a girlfriend. The few clothes I had were hidden in a suitcase. I had asked Carole what she thought of crossdressers, drag, and trans people one night. She had told me they were all sick in the head and that a man would always be a man. It was strange in a way. She never had a problem with gay people.

Our marriage lasted until were both in our early 50's. By then, I guess there was just too much resentment and frustration between us. We never had kids. According to the fertility clinic we both had problems, although she blamed me mostly.

I took any excuse to be away from home and stay in hotels where I had restarted my crossdressing. I will admit, I did get a sexual thrill being dressed. I dismissed my desire as a kink. I didn't really want to be a woman, did I? Whenever I could, I would venture out for little walks in the evening. I would be careful to use the stairs. I did not want a close inspection by someone in a lift.

My confidence grew when I walked. I did not get any second glances. I think unless you draw attention to yourself you are just ignored. I went for the plain, almost mumsy look. Always skirts or dresses though. I had nice legs. Why not show them off I thought.

The turning point came when I hired a cottage in Norfolk for five days. I spent the whole time as Sarah. When I arrived, I had a long bath and shaved myself smooth. Then I changed into a simple blue cotton dress, with my stuffed bra, knickers, and tights underneath. I took an age to do my makeup. After all, this was for five days, not just a few hours in a hotel room.

I had to dab my eyes carefully with a tissue when I finished. For the first time in my life, I truly looked like a woman. The face looking back at me had the most wonderful smile. Steve never smiled like that. In fact, Steve never smiled much at all.

This was a revelation. I just felt an inner peace and calm that I had never felt before in my life. This is who I should be. I had wasted my life. The morning I had to pack and leave, I broke down and cried my heart out.

As I drove back home to my tiny flat I felt rage for the world that I lived in. It had taken me fifty years to find out what had been wrong in my life, but there was nothing I could do about it. I knew if came out I would be in for the worse experience of my life. I had read about the crap trans woman face. They lose their jobs, their friends, and their families. They are way more likely to end their own lives or be killed.

I had suspected I may be trans for a while, but shied away from the idea, not wanting to deal with the possible consequences. Now I had sampled the life for a brief moment I knew would never be truly happy if I did not do something. I had difficult choices to make.

I thought back. growing up I watched the girls at school just wishing I could be one of them. I wished I could look like them, dress like them and act like them. Not having any sisterS my chances of dressing like a girl were nonexistent. I retreated into my own little fantasy world. I was classed as a "thoughtful" boy. I was just imagining I was Sarah, instead of Steve, playing hopscotch instead of being picked last for football.

Now after five days of blissful happiness, Sarah had come back with a vengeance.

"You must Steve, you know this is what you want."

"No, the problems. If I had more money I could go away to somewhere no one knows me, but I need to earn a living. Can you imagine what they will say at work?"

"You'll be happy, truly happy, you know I'm who you should have been. All your life you have known it."

I sobbed as this went through my head and thought back to something I had read a few days before. There was an article about how great it was to be a man. How much privilege we have. Being a white man is like winning life's lottery. It made me feel sick to the stomach. I knew never wanted it. Being told how lucky I am to be what I am and almost hating my existence.

"Steve, you have one life. Do you really want to live with the regret you will feel if you don't become me?"

"Sarah, please I'm scared..."