After my miserable failure responding to a Craigslist personal, I vowed never again! Eventually I decided to try a little target marketing by posting my own personal. Here is what I went with:
Classy CD Seeks Mature Guy to Play With - t4m
I am a mature crossdresser who loves to dress up and go out as a woman. I pass with ease and go everywhere! If you're a clean, sophisticated guy who digs chicks like me, would you enjoy a charming companion for dinner, drinks, whatever? I am very affectionate and adventuresome when I'm dressed up as a woman...send me a picture and let's e-chat!
Needless to say, I was swamped the next morning with responses. After weeding out the sickos (like some guys sent gross pictures of their naked bad hairy bodies, ewwwwwwww!) I singled out three guys, gave them each a link to my Flickr site and asked them a lot of questions. They each sent me pictures of themelves, and after chatting with all of them at length to satisfy myself that none of them was likely to hurt me, I learned that they all have this fascination with crossdressing and crossdressers, eventually I even got two of them to admit that they'd secretly like to try it themselves, but they all wanted to hook up with me as the chick and them as the guy...what's a girl to do?
Rather than risk going out, I got a hotel suite with a kitchen, and I invited each of them over for lunch or dinner, told them if they brought the wine I'd whip up a lovely meal for them. I'm still coming down from an amazing 24 hours...I felt like Scarlett O'Hara! One of the guys is an absolute dreamboat, he was one of the ones who secretly yearns to dress as a woman. He is tall, dark and handsome (6'4" and very well built) but although he is gorgeous I told him he would be pretty in pictures but passing would be a challenge...after I fixed dinner for him, we played for a while, what a hunk! After him, the other guys were kind of a letdown, my lunch date was awkward and my other dinner date was okay but the chemistry just wasn't there....
I know I took some terrible risks and I don't think I'll be trolling on Craigslist anytime soon, but I sure can't complain about the result: my dream guy wants to see me again!
Cissy
Originally Posted by Annemarie
