The First Date

I wait nervously by my front door. I am trembling. This is my first date. Simon is picking me up at 7.30. It is 7.35 now. I have been ready for an hour. I check my reflection in the hall mirror for the 50th time.

My red tinted shoulder length wig looks perfect. It cost a fortune. Real human hair. I have been spending most of my wages on clothes and makeup since I decided to stop fighting against my desire to be a woman. I have struggled to be a real man all my life. At 5ft 6 inches it has been difficult to look the part.

My slim figure and gentle ways made me popular with women. I had lots of girl friends, but they were just that friends. I learned from one that they thought I was gay, so I was a "safe" person to have around. One told me I wasn't like other guy's, who were always trying to get into their knickers.

If only they knew. I loved women, not sexually, I admired their looks, their clothes. I wanted to be them. I always looked at women, but it was their style and clothes I was looking at, not their figures.

I moved out of my parent's house to London when I was 25. I have been living here for 2 years. One thing about London is that it seems anything goes. A few months ago we had meeting in the office and I met my first real life trans woman.

She was an I.T. engineer on a temporary contract updating out laptops. She looked amazing. She was wearing a leather mini skirt and fishnets. She had goth style makeup. I stared for too long.

"Yes, before you ask, I am trans." She said.

I apologized and swore I looked at her because I admired her style. She forgave me and we had a chat over coffee at lunch. She told me her life story. It reminded me of my life. She seemed so happy. Right then I made the decision to stop fighting and pretending to be a man.

That night I spent most of my saving on clothes, wigs and makeup. After a few years of dressing at home I had a yearning to be seen, but I was just too scared. In my early 20's I started to notice men. I found myself looking at their eyes and their backsides. I assumed I must have been gay.

I needed recognition. I thought I looked good as a woman, but I was too scared to go out. My solution was to put my pictures on a trans dating site. Within hours I had hundreds of messages. Most were filthy, crude and horrible. How some of these guys ever meet trans women or any women amazes me. If your idea of a chat up line is. "I'd like to bend you over and ......" good luck.

Simon seemed nice. He warned me that the site was a "meat market", and to be very careful who I met with. We messaged each other for a few days when he asked me out on a date. My first ever date.

I'd gone flat out. I had shaved every inch of my body and taken ages with my makeup, I even wore a corset to give me a more feminine shape. This was my first date, and my first time facing the world as a woman.

There was a knock on the door.

"Hi Kerry, it's Simon. Are you ready?"

I could almost not breath as I opened the door. He stood back from the step and looked me up and down. I was wearing a long-sleeved knee length velvet dress, it had a small split at the sides. I was wearing 3-inch black sandals. My red painted toes could be seen through my seamed stockings.

"Wow Kerry, you look absolutely amazing."

"I'm not sure about this Simon. I am so nervous I can hardly walk."

"Honestly Kerry, no one would ever take you for anything other than a beautiful woman."

He leant forward and gently kissed my cheek. He offered his hand, which I took as I closed my front door.

I could hear my heels click on my garden path. I just hope my neighbors were not looking out of their windows. My handbag slipped off my shoulder. So much to get used to. As I walked the hundred yards to his car, the light breeze blew the perfume about me. I loved the sweet smell.

Simon turned to me and smiled. He looked so confident.

"Not far now beautiful."

Beautiful? This was the second time me called her that. I wasn't used to anyone complementing her appearance. A little thrill ran through me. I was aware of her garter straps tugging gently on my stockings as I walked. My legs were rubbing together. I could hear the faint zipping noise of my stockings.

She could feel my knickers being moved slightly by the garter straps. The silk was gently caressing my small member. I was starting to get hard. I had to stop thinking about how I was dressed. I didn't want to show through my dress.

We arrived at Simon's BMW. He stood by the passenger door and kissed me on the lips. I wet my lips as I drew away and he opened the door for me. I could taste my lipstick. I thought back to youtube videos I had seen. I gently eased into the car seat and swung my legs in, keeping them together. So many things to remember. So different doing it as a woman.

Simon closed the door for me. No one had ever opened a door like that for me. It felt like I was a precious thing. Something to be cared for. It was intoxicating.

When we arrived Simon parked, opened my door and took my hand to help me get out. As I sat in the Italian restaurant I could feel my knickers had ridden up between the cheeks of my bottom. I could feel the lace slightly tickling me.

I smiled at Simon when he asked if he could order for me. I had little experience in eating out in restaurants. Simon ordered in perfect Italian. Well, I thought it was anyway. As we drank wine, he held my hands and stared into my eyes. I felt myself melt inside. He looked so manly. I breathed in his musky aftershave and felt so "womanly" next to him.

No one gave me an uncertain glance. I got a few admiring glances by some of the men. It felt so right. I felt I belonged in this life. I wished I could stay like this forever. Simon paid the bill and rushed around to pull my chair out for me. He offered me his arm and we walked to his car.

With each step my sensuous clothes made themselves known. I was in heaven as I sat in the car with him. I was his woman at that moment. He was my man. He leaned across and pulled me in for a deep kiss. His tongue explored my mouth, probing and tickling. I felt so vulnerable as he penetrated my mouth. His hand was on the back of my neck holding me in place. I was his.

"Why don't you come back to my place for a coffee?"

My heart felt like it would break through my chest. So many firsts tonight. Would Ishe let this be the first time I made love? Could I?