Yes, many times!
I've had several dreams, not necessarily of being a woman, but wearing women's clothes. In one dream I was wearing a very sexy bathing suit, and I got a pretty good look at it too before I woke up. I wanted to go back to that dream real bad, but was unable to do so.
But the dream that started it all for me was, the Princess Peach dream. I was playing Super Smash Brothers and chose Peach as my character, and as the first round was about to start, I got sucked into the tv. Next thing you know, I was wearing Princess Peach's outfit. I saw that I had breasts, and my hair was long and blonde too. I even felt taller, which I confirmed when I saw that my feet were nicely snuggled into a pair of dark pink high-heel shoes. Everything in her outfit was on my body, and I could even feel her crown on top of my head.
Since I had never crossdressed before in my life, and had not even given a single thought to wearing women's clothes, not even panties, one would think I would be weirded out by this. Actually, I did in the past wonder what it'd be like to be certain female characters in video games, such as Chun-Li from Street Fighter, or Seung Mina from Soul Edge. But I still did not have a desire to crossdress though.
But when I magically transformed into Peach, I suddenly felt very girly and feminine, and I was overcome with a strange but terrific feeling. I was enjoying this!!! I did not know why I was enjoying it, but I didn't even think about it for even a second. I took a good long look at myself as I glanced down to look at the outfit, and I admired myself. Then Peach's mind seemed to take over as the round began. I jumped right into the fight, throwing punches and kicks, determined to prove that I was not just a helpless princess, and also that girls could fight too. Sadly, the dream was very short, and I only got to fight for a few seconds. But I do have the satisfaction of knowing that I scored a few hits and did not get hit myself before the dream ended.
From there, the rest is basically history. I bought a couple of Princess Peach outfits and dressed up as her ever chance I get. But I figured it was just a fantasy of mine, and did not even give any thought to the fact that I was actually crossdressing. To this day I still do not know if I was crossdressing, cosplaying, or if they're both considered the same thing if a man wear's a woman's cosplay outfit. But this is how it al began for me.
I've had from time to time dreams where I was starting to transition(no plans to irl) or out shopping with friends and/or family and I would buy women's clothing right in front of them and they wouldn't say anything about it even though they don't know that I am a crossdresser irl. I've also had dreams where I was a drag queen and was getting help with my make up before a show. I remember on dream I had many a years ago in high school that I was having football practice and everyone of my teammates had their full equipment on except me. I was standing there in my favorite panties at the time, but no one noticed. To them I was still in full equipment but to myself I wasn't.
Maybe ... Does your head contain a closet full of dresses? If so, then I probably in your head. LOL
I had a similar image. I used to go to a woman regularly for a relaxing massage. But, I always tensed up whenever she got to my neck. One time she said, "What do you feel when I massage your neck? Tell me what is the first thing that comes to mind." I told her I feel like someone just came up behind me and started to choke me. But, I'm a girl with a short black pageboy haircut. She told me that it might be a memory from a past life. Kind of scary to think I got choked to death in a past life.
Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.