I have often suggested to people who have talked in chat about dressing up that a good place to start is panties and a nightie. I know many have started by swiping a pair of their sister's or mother's panties or a bra or even a nightie. My start came years later, but it was with my sister's old lingerie.
It made sense that it would be a bra and panties under my clothes, then a bra and panties under her old clothes, then it was shopping for my own. More, more more...
Lingerie is the best place to start because you can do that in private and find out very quickly what it means to you and how it makes you feel.
My sister had a pair of red panties and a red lace nightie. I won't deny the many times I pleasured myself to the thoughts of dressing up and even being a real woman. So, I pleasured myself when I slipped into her old nightie the first time.
What frequently happens in these cases is the guilt sets in and you get that stuff off of you as quickly as possible. You feel ashamed. What would everybody think of you? This is a hard thing to get past, but frequently people will do this again and again. Always sorry for what they did, but always coming back.
You know why they come back? It makes them feel good to be in touch with their femininity. It is the most amazing thing when that guilt washes away and you are just you. You accept your feminine side, or the fact that your feminine side may be much bigger than your masculine side. There really is no wrong answer here. It's just who you are and what makes you happy.
That night, way back when, I pleasured myself, cleaned up and slept in my nightie. I knew this was more than just a turn on for me. Of course, I also knew I needed more lingerie, and I went crazy shopping for things. I'd even buy a bra and panties at The 99 Cent Store.
Body shaving came not long after, and I did it every week to stay smooth. It's tedious, but I love the feeling. When I slip into a satin nightie over my smooth body, it's an amazing feeling. And I don't have to pleasure myself to enjoy that feeling. I just am.
So, starting with a nightie, panties and even a bra is a good place to get started. You can get those items very easily and wear them in privacy. Is it a turn on? Then enjoy it and be happy. Is it more than that? You can explore those feelings further at your own pace. There is nothing wrong with who you are, so don't be ashamed. Be proud.
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