I've read a few stories on here some good most bad.
I figured I would throw my own experience into the mix and try to bring something fresh to the table.
I feel like you can tell most of these are fake, so here is a TRUE story about my first time with a trans girl.
Backstory - I've been closet crossdressing ever since I can remember. My older sister was in pageants and dance recitals growing up, so I guess maybe her getting all the attention may have led to the start of my fascination with dressing up and feeling "pretty". I'll probably add some stories about my experiences with me in girl mode, but for now just know that my own interest in the CD world is what led me to talk to this girl. I knew that trans girls were usually not into crossdressers so I approached a girl who lived in my state in full on straight boy mode ONLINE of course in fact it was in the good ole days of Myspace. For her privacy Let's call her "Ashley".
To this day all my family and most of my friends know me as a normal straight guy. I sent her a couple cheesy introductions online. Ashley was hot in her pics!!! She was short, skinny, tan, had gorgeous legs and a perfect smile. It was obvious she was a full time girl and I was really excited to get to know her. I never thought I would actually meet her in person so I flirted her up as much as I could just to dream about being with her. She was really into the club scene and definitely out of my league but hey what was the harm in trying. She ignored the first few attempts but finally she started talking back more and more. I was fresh out of high school and kinda just dating around trying to figure out what I wanted out of life.
We talked back and forth for a few months up until I started my freshman year in college. We did not chat as much but we did jokingly say we should meet up one night a few times. I had never been on my own and had true freedom to come and go as I pleased. By then I had a semi serious stable girlfriend and had no intention to cheat on her. One night Ashley hit me up on Facebook asking to come pick me up and hang out. Winter break had just started. It was late, I was really horny and almost everyone had gone home for the Christmas holiday including my girlfriend. I was in my dorm alone and bored.