“The world seems a bigger place when you wear a skirt….”

“That’s one small step for man, one giant leap for mankind” quoted Neil Armstrong when stepping foot onto the moon.

Although not anywhere near the scientific or cultural impact, for me stepping out as Samantha at night was something of a big deal.

In this article, I want to share my experience with everyone and maybe inspire someone else to make that step.

En Femme Style

Before I get into details, a little bit about myself. I have been crossdressing for over 30 years; however, Samantha has come into her own as well as expanded her wardrobe during the last 3 years.

I do not want to go beyond the alter ego and have no plans to transition. Just like the pioneers of space, I want to keeping pushing the boundaries of my own limitations and have these wonderful and ordinary experiences as Samantha.

Whenever I hear the phrase “girls’ night out” at work, Samantha has always seen an opportunity to be a part of the fun but never followed through on it, until two weeks ago that is. Let me explain….

When a colleague was announcing she was leaving and having drinks at a local pub, I decided to chicken out no more. This would be the moment Samantha would come out of the training simulations. Before I describe the events of the night, a bit of background…

I work for a very accepting and understanding company. This means I can be in the office, working, dressed as Samantha. It’s not every day but every now and then. To be honest, I love the opportunity to put on something smart & professional then get on with the day.

This particular day at work, I was dressed as Samantha, as per picture above. As soon as 5:30 came around, following a little touch up to my makeup, a quick spray of Britney and a tug of the tights, it was time to make that giant leap out the door and into the pub on a Friday night, of all nights, Yikes!!

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When I say giant leap, it was more of a pub across the road, although for me and my overthinking brain, it may as well have been on the moon.

Determined, with a deep breath and handbag over the shoulder, it was out the office and into the pub. Walking in, the pub wasn’t that busy plus the girls were already there, so I pulled up a chair and sat down.

Task number 1, order a drink. If nothing else tonight, I was determined to do this. Walking confidently up to the bar I ordered a gin & tonic which seemed appropriate. That went well, score one success for the Samantha!

Sitting down, cross legged, as one of the girls and just chatting even for a few hours was so much fun, there was not an issue at all. I did make eye contact with a woman across a table, however this was just fleeting and she, like the rest of the ever-increasing number of patrons got back to starting their weekends.

As the pub got busier, I did start to retreat into myself a little and noticed myself clutching my handbag ever tighter on my lap, self-defense mechanism perhaps? Thankfully there was no bother from anyone all night. Come 9pm, it was sadly time to leave and bid farewell to my fellow girls. Stepping back out into the cold air felt like the end of a brief yet great experience, almost akin to landing on the moon, I suppose.

Perhaps the world doesn’t feel bigger when you wear a skirt after all.

I am not sure when Samantha will step out again but with freshly painted nails, touched up makeup and a with a firm grasp on the handbag, I will be ready and for another adventure.


Does this positive experience I’ve had in my recent past inspire some of you CDH girls to make that giant leap of taking your femme self out in public for the first time?

What is your specific issue which may be keeping you individually from making your giant leap out in public as your femme self?

Would you feel more comfortable going out in public as a lady your very first time in a girl group setting such as the one described above in my article? Or would prefer flying solo on your first time out as the femme version of yourself?


Thank you so very much for taking the time to read my article.

Please feel free to answer any one or more of the questions I’ve posed to you above! I look forward to reading your replies!



Sincerely, Samantha

En Femme Style


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Samantha Joan

My crossdressing journey started at the age of 13, although upon reflection, it probably started a lot earlier. Growing up and trying to dress was difficult. There was no internet, so my access to fully understanding and knowledge was almost zero. My parents knew, talking was tough as instead of confronting my crossdressing I ran away from the conversation, sadly never to be talked about again. Like my favourite sci-fi saga, there was an awakening in the force, Samantha came into being, thanks to some very supportive people who fully invest in my journey. I am here to be part of this wonderful community, support others and share my experiences, plus if anyone knows the secret to a perfect, flawless makeup look, please let me know. Thanks for reading! Hugs, Samantha x x x

Latest posts by Samantha Joan (see all)

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Stephanie Kennedy
Active Member
2 years ago

Hi Samantha I loved that story it must of been so exciting for you. That outfit looks really. cute on you. Just my opinion if it was my first time out again I would prefer going out with a cis woman friend. I felt protected when i as out with her for some reason. I think about it now it is almost acceptable for a cis woman to have a feminine gay man as a friend. It doesn’t matter if you are gay or not. Most girls will think that anyway. So just go with it and enjoy being one… Read more »

Shyanne Dee
Shyanne Dee
2 years ago

Thanks Samantha. I don’t know when my big time will be, but reading others stories give perspective and encouragement

Thanks, Shyanne

Alexis Thorne
Alexis Thorne
2 years ago

Thank you Karen, for a great article. It and a number of drag queen and CD videos I’ve been seeing on YouTube these past few years have inspired me to come back onto the crossdressing scene. Can you tell me how to upload pictures from my phone to the Crossdresser Heaven site?

yours truly,

Alexis Thorne

Cheryl Ann (Cassie) Sanders
Active Member

Great little slice-of-a-cd-life essay, Samantha. For me, it was always the just “being” a girl in the world that was the best feeling. For some reason, being another girl among a clutch of girls seems like among the best of those experiences. (Probably the second best of all.)

Curious about what kind of a office and group of co-workers is so accepting of your occasional presentation as woman. What industry is it, for example? (Imagination tells me that it would be more likely, for example, a design firm than a firm in finance or such. Am I right?)

Layla Jones
Layla Jones
2 years ago

A lovely read and glad it was as positive as it was x

Chrissie Cross
1 year ago

Thanks for sharing Samantha! What a great experience. I lived vicariously for a few moments. Thx Chrissie 

Sarah Kanter
Active Member
11 months ago

Hey Samantha,
I remember reading this article a while ago and enjoyed it again just as much as the first time. I hope you’re doing well a year later, and still able to get out when you want.

All the best!

Sarah Kanter
Active Member
10 months ago
Reply to  Samantha Joan

Sorry you’re not working, hope all is well. Not having a job is stressful. Good luck with the hunt! I think finding a job is more work than actually doing a job.

Sarah Kanter
Active Member
10 months ago
Reply to  Samantha Joan

I’m well. Just work and the usual. I haven’t been dressing up as much lately but everything is pretty good. Looking forward to summer trips.

Charlotte Bambi
2 months ago

I have to say. I love your look in this photo. I am going to try to emulate it for my first trip out in January. Thanks for the inspiration.

Kerri Smith
Active Member
2 months ago

Thank you for an inspiring story. I am so happy that your workplace is so accepting. I worked in an engineering company and most of the people there were homophobic. I have been out a few times as Kerri. Having a coffee at Starbucks or shopping in department stores. I would have loved to do it with another lady whether cis or trans. Please continue to expand your horizons tell us about your continued adventures.

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