Building confidence by crossdressing in a swimsuit

It’s been about 4 months since I started living as Natalie full time (except for work) and I’m loving it. I’ve never been happier or calmer. I have done, experienced and learned many things.

I’ve been swimming. I was invited to a friend’s pool party, so I went shopping and bought a cute 1 piece swimsuit and a sarong to match. I felt really exposed and scared to take off my sarong, I had never worn anything that revealing in public, well semi-public it was a small party, about 5 people. But it was really hot and the swimsuit is very comfortable to wear. I took off my sarong and got in the water and no one batted an eyelid.

I was out shopping recently and a woman came up to me and said “You look lovely, I really like your dress.”

Before I was fully out I would go to the shops of a night time, fully dressed when everything was closed and there is never anyone there. I’d practise walking, up and down the street, and window shop at the ladies clothes stores. So in the last couple of weeks I have made a point of going into every one of these shops, fully dressed and in the middle of the day. In every shop I went to the people were quite friendly. I started chatting to one lady shop keeper, we chatted for 45 minutes, and in the course of conversation I told her what I was doing and she congratulated me.

I went and had my eyebrows shaped and my eyebrows and lashes tinted. Turns out my beauty therapist for the day works in my hotel, and her husband is the concierge.

I started wearing ladies clothes to and from work. I have to wear a uniform at work, and I’m only wearing ladies jeans, a t-shirt cut in a feminine shape and underwear. I don’t think anyone has even noticed.

I went out for cocktails. A friend invited my wife and I to go out for cocktails. So we are sitting having a drink and a chat when this guy, who is sitting with his girlfriend gets up and starts walking toward me. He looks a bit sketchy and I’m preparing to either ignore him or defend myself when he smiles and says, “You look really good tonight, good effort” and holds out his fist for a fist-bump. I was so surprised, and strangely pleased, by all this I just mumbled my thanks and went back to my conversation. I wish I’d had the courage and the presence of mind to invite them over to join us.

I met other girls for the first time. I met some ladies on a local networking site and we met for coffee.
Each event generated a feeling, each was a completely new experience and each one gave me something to think about and learn from.

I still get afraid, but not as often. The fear is not as strong. I think I’ve worked out the confidence trick. You don’t actually go out with confidence. It doesn’t come to you, you have to go out and get it.

I think I saw this in a film, or maybe read it, and I’m probably not quoting it correctly, but it goes something like this:

A scared, young soldier can’t go over the trench because he’s paralysed with fear. The sergeant yells at him to go over the top and young soldier says he can’t because he’s scared and not courageous as the sergeant. The sergeant tells him “Courage is a myth. I’m scared too, but I’ve learned that the courage comes after. You don’t go out because you’re brave you go out because your scared. You go out scared, do the scary thing, and come back with courage.”

It’s the same with confidence. Confidence is just quiet courage. You do the scary thing and the confidence comes later. This is the confidence trick.

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Codille Benton


This is a great article! Congrats on your progress!!!! I see this is part one, looking forward to part 2!!!

Codille Benton
Tiffany Anne

Congratulations on going out and “getting your confidence”. Great article, thanks for sharing!


Lovely Natalie, you must feel so proud of yourself

Maggie Honey

Nice article. Congratulations! While I know that it is not easy for any of us to find the confidence to do what we want (and need) to do, I think that it probably harder for those of us raised in the ’50’s,’60’s and ’70’s due to the different attitudes society had and the emphasis placed on what others thought. I find that as I care less about what others think about what I am wearing, I become more confident and comfortable wearing it. Hugs. Maggie

skippy1965 Cynthia
Trusted Member

Great story NAtalie and so so true. In the TG /CD world as in many other worlds, confidence (and a smile if you can manage it 🙂 ) is indeed the key! Act like you belong there and people key off that confidence!

Frances walker

hi skippy its frances thats what i need more confidence ill bet you have plenty i hope iam contacting you i want to make friends

britney silk
britney silk

congratulations on your new found confidence,I’ve recently started going out dressed,fully made up,I’ve found out the same things you have,it’s scary at first but after a few times confidence starts to build,and I’ve really started to enjoy myself when out,i find the best part is when people just don’t realise your who you are , believe in yourself, and others believe in you,I work as a man,it’s getting very hard to change into a man for work now,just want to be a woman all the time, i don’t think it’s going to be long before I start being the woman… Read more »
Laura Lovett

Wow! This is exactly right, and exactly what I am doing instinctively. I could not have put it better.

Sisters, be inspired by this.



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