Note: I wrote this a couple weeks ago, looking for input before I write another.
How I became a Crossdressing Sissy Slut –
When I was 16, the summer before my Senior year in High School; I use to chat and cyber with men and women from around the US. I use roleplay/catfish as a teenage girl, most of the time if they asked, I would tell them the truth. I found a guy that lived near me and he convinced me to meet him. He knew I was a boy and enjoyed being a girl.
We talked about what we could do together. We concluded that I could probably fit in his daughter’s clothes, who’s a year older and just graduated. She was out of the house a lot and he found himself alone on his days off while his wife worked.
The day came and I showed up at his house. He was super nice and offered me a alcoholic drink that I took him up on, to calm the nerves. We both were nervous, neither of us had done this before. He showed me his daughter’s room and he had laid out an outfit he would like me to wear. Short while skirt with a lacy tank top. Matching bra and panties of course.