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I have constant dreams about being dressed as a woman while being with other women. I'm not gay I should point out but I always feel really good afterwards.
It sounds like you feel like you aren't showing your true self to people. The woman's clothes represent something that (probably) isn't you.
I'm a heterosexual male with an obsession for women's clothing. I dress almost every day in the privacy of my own home. I am a widow and I too fantasize about sharing my femininity with a women. However, it won't happen on its own and I struggle with the thought all the time. I dream of being invited by a women to be a contestant in a women-less pageant and she helps me look my feminine best. I also fantasize about going to a renaissance faire wearing a period women's dress. I don't know how to make this happen but I continue to dream on. Keep trying - it may happen.
I love wearing womens lingerie and jacking off while wearing it. I used to wear my mom's and stepmom's when I was younger and love it! It will make you cum a ton
This sounds like a normal good dream to me. Socially conventional, of course not - but that's the beauty of a dream. It lets you explore. It gives you metaphors. Sometimes you even wake up feeling good after. You don't have to be gay to enjoy your mind's experience.