Women Out in Public

Ok, so I have dabbled in dressing out in public, but only driving the car wearing lady’s clothes and never getting out. I’ve been lucky enough in the last year to do a few long distance journeys on my own. A couple of the trips were from one end of the country to the other. About three months ago, after many years of struggle, it struck me that I was a crossdresser and did not want to transition to a woman. I made the decision to go all out in my effort to pass En femme at some point in the near future. I started to plan a night out at the local crossdressing pub in Norwich, using an excuse as a photo walk with a local club I am with.

I started to purchase all the things I would need for the event. The items would make me look and feel as close to a woman as I could make myself. I purchased hip pads, foundation (challenge to find my match), eyebrow pencil (I am lucky enough to have light and quite feminine brows for a man), nice cherry lipstick, eyeliner, and mascara. I also bought some jewelry (small hoop earrings and some nice bangles, which needed slight modification in order to fit my wrist. The final touch was a nice, passable, brown shoulder-length wig. I also bought some nice everyday black underwear and some comfy nude kitten heels.

The house was empty for a few weekends so I was able to practice my makeup skills, self taught as it were, in an area that I have never attempted before. The first foundation was far too light, and I never realised the eyeliner, mascara, and eyebrows were so hard to apply. After a few times, I started to get a reasonable result.

Then it happened; I had the chance to go out to the cinema, on my own, to see a one off showing on a Monday night in December. A slight change of outfit was needed; something a bit more casual. I chose a nice Joe Brown skater dress, Cami top, and casual ladies trainers. I also bought a nice scarf, clutch bag, and a pair of fake glasses to help with the look.

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The night came, and I shaved as close as possible. I also shaved my arms as I don’t have much hair on them, and I thought I could get away with it. There was no chance with the legs, but I felt the tights should do. There wasn’t any chance to get sorted at home so I left early and found a quite lay-by on the way. Beard concealer and basic makeup applied in the car using the vanity mirrors—fun times for our cause, but I think I pulled it off. Pulling into the car park, the last thing to go on is my wig. I needed the foundation to dry as I found that the fine strands of the wig stuck to my face. No-one tells you about these fine details.

And so; I stepped out of the car…

I have never felt so exhilarated. I felt awesome and empowered and not nervous. This is what I should have done years ago, and I wanted to enjoy it. It was very quiet, I admit (Monday night at a cinema), but there were people about. A lone woman checked me out with a quick scan. Was that a catty look? I really hoped so, and it gave me a kick inside. The rest of the evening went without drama, I wanted to checkout my look in the ladies room, but the quiet loos, near the entrance to mall, were closed. Just have to go with it this time as I was not going in the main cinema toilets. Not brave enough my first time.

I didn’t have to talk to many people, but I seemed to pass the whole evening. It was that or no one confronted me. I didn’t notice people gawping at me. Just remember to act and walk like a woman and be confident I told myself. What a fantastic experience, and one that I can’t wait to do again. I just need to make sure that I get all the makeup off before I get home.


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    Rachel Ousten

    I have been crossdressing since a child. Thought I was transgender until very recently discovering crossdressing is what I really am, the best of both worlds

    Latest posts by Rachel Ousten (see all)

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    4 years ago

    Thanks for posting this. I am planning to go outside and visit somewhere casual in the next couple of weeks. Can’t wait but I am sure I will be nervous.

    Kendra Carter
    Active Member
    4 years ago

    Hi Rachel and thanks for posting a great going out story. Once I get my makeup looking somewhat feminine I’ll try my best to step out for part of an evening!

    4 years ago

    Hi Rachel, thank you for posting up your story! I love seeing where our sisters go out, love reading the stories about it, and stories like yours illustrate that it’s not nearly as fearful a thing as we often build it up to be in our minds beforehand. Congrats & cheers hon! ❤

    skippy1965 Cynthia
    Trusted Member
    4 years ago

    Congrats on getting out and about Rachel!

    Daisy Marie
    Active Member
    4 years ago

    Congratulations Rachel!
    That’s a huge step for any crossdresser….go out and about, get rid of their inner fears and replace them with great memories.
    I hope this first experience serves as a springboard for many other outings.
    I haven’t done my debut in public yet but I’m feeling it’s closer than ever…..and the feelings I have are quite similaar to yours right before your endeavour.


    Clare Jackson
    Active Member
    4 years ago

    Well done you. Lovely to read and very happy for you XX Clare

    Danielle Silverfeather

    Rachel, I love your story. I remember my first time. But it feels so right. I went through the struggle of thinking I was transgender also. But realized who I really am

    4 years ago

    This is almost the exact same experience as my first time out! Movie and all 🙂 Thank you for sharing!

    4 years ago

    Rachel; wow thanks for the story and postings as well – it was very hard to do and well worth it also – it took me several weeks to finally get up the nerve to get fully dressed and venture out and about – I got dressed and waited until it was somewhat dark outside so I could leave the house with nobody seeing me – I got in my car drove around for awhile to try and find a place that didn’t have a lot of people out and about walking around – I found the place sat there… Read more »

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