My First Date As A Woman

I have been fantasizing for a long time about going on a date as a woman. I have been going out dressed for many years. But dating was just a fantasy. I met a guy online and chatted for a few months. He asked me to go on a date. I was apprehensive at first because we are never totally secure with our female looks.But I have become more comfortable out in public as Jessica. I have been shopping and spending extended periods of time as a female.
So I decided to go for it. He picked me up and told me I looked beautiful. He opened the car door for me and was quite a gentleman. We went to a Mexican restaurant. I was very nervous about walking in and having everyone look at me. I was also scared to order thinking my voice would embarrass me. Well it all happened so fast I didn't have time to think. We walked in and the waitress sat us in a booth. We were chatting and the waitress came for our order. She looked to me first. Without thinking in my best girly voice I ordered. I relaxed after that.
We had a wonderful time. I am soo glad I did it. I will be seeing him again.
ka851 ka851
51-55, T
1 Response Dec 16, 2012

Hey girlfriend, I know the first date jitters myself. Actually I had been going out in public as young woman before I ever went on a date. It was exciting having men flirt with me because they thought I was a real woman and wanted some of my vagina. If I try to write p_ussy in here I always get 5 asterisks instead. I knew my deception was good. I was 19 when I gave up my female (anal) virginity to a 35 year old man that became boyfriend for several years. He was the first man I went on a date with. I practiced my female voice using a tape recorder but when he first started taking me out he would order for me. It was, "The lady would like," or "She would like," and order it for me. But I did start eventually ordering for myself. He got me a fake female ID with my sex listed as female and a picture of me as a woman so that he could take me out to nightclubs, bars and restaurants so I could drink alcohol. The legal age in California is 21. We were just like a man and woman on a date. As we walked I would hook an arm around his and carry my clutch purse in my other hand. If in a crowd he would put his hand on my bottom and kind of guide me. Of course I also had to be a woman for him in bed later in the evening. It was an actual boyfriend/girlfriend relationship and I was the girlfriend of course. I spent many nights laying face down on my tummy with him on top of me thrusting into me and I absolutely loved it. It made me feel so much like a female being made love to like I was a girl or woman. It was just through a different hole. I have dated as a woman with a number of men over the years. I feel so feminine and womanly being taken out on a date by a man and then later being a woman in bed with him. If I could have been made pregnant I would have a lot of kids by now.

true love never forgot

Julie - I would absolutely love to date a trans lady like you !! I would enjoy soothing away your insecurities and vulnerabilities and have you proudly on my arm. That would be so wonderful.