I never in a million years thought this would happen, but I've started dating...as a woman. A few weeks ago, I hooked up with another CD'er who was visiting Chicago and we spent some time together en femme. We really hit it off, although we have very little in common except our crossdressing. I asked him if he would ever want to go out sometime with him as the guy and me as the girl, and he said okay.
The next time he was in town, he asked me out on a date! I know this sounds ridiculous, but I was so nervous putting on my makeup and deciding what to wear. I really wanted to look pretty for him. He may be a "plain Jane" as a girl,but he is a very good-looking guy and a well-mannered gentleman. After he picked me up, it was one thrill after another as he opened doors for me and told the waitress that "the lady will have...." I took his arm as he walked me home, which felt wonderful, and when we kissed goodnight, it seemed so natural.
He's been back twice since then, and last week I cooked dinner for him. You should have seen me in my apron setting the table and lighting candles. It is all so innocent: we haven't gone beyond hugs and kisses - we are both straight - but I am starting to like this way too much....
Usually I'm the one giving advice, but I could sure use some now. Should I break this off before it goes too far? Or just enjoy it while it lasts and see what happens?
Windy