I was so scared about my first attempt at going out en femme. It is something most of us understand, either because we have gone through with it, or because we have not had the courage or opportunity to take that first step into public. For me, it was a little of both. This is how I finally got from the closet to realizing my first outing – and it was a TOTAL success!!

Reading through the articles and stories in Cross Dresser Heaven, you can find so many common threads about our experiences, which is why I think we congregate here. We find enough commonality in our struggles with identity and acceptance to validate our experience, and the differences we find in these stories may stir some new thoughts or inspirations of possibility for us.

When I discovered CDH earlier this spring in the midst of the COVID pandemic, I finally realized that THIS would be the time I came to terms with my dressing and identity. I had been in the closet and the shadows long enough. I needed to officially recognize and honor this part of my personality and come to terms with the fact that this feminine side is something that makes me unique and wonderful instead of something I believed was wrong or perverted and should be hidden from the world. At 45 years old, the mid-life crisis might just be kicking in, but I know I have felt this way my entire life. That back story will have to wait for a different article, but you would find it to be very much like so many life journeys that have already been told here on CDH.

My wife is the most wonderful lady in the world, and I am so thankful every day to have such a great partner in life. She has supported me in so many different ways in life and career, and has put up with some pretty challenging explorations of my inner demons throughout our 23+ year relationship. She really is an angel. She has been aware of my crossdressing interest for many years, mostly showing up shortly after we got married. Leotards, pantyhose, the occasional one piece swimsuit would work its way into some bedroom fun, and she tolerated it. It came and went over the years, and much like so many of you, I went through many purges of my stash. Over the past several years, I’ve been slowly collecting some impulse items which has caused a few challenges in our relationship. I had been passing it off as frivolous and just satisfying a fetish, so she did not understand why I needed to keep buying new items when I already had a bunch of things I was never going to wear in public anyway. I had a very hard time coming up with a good answer because I couldn’t come up with an answer for myself.

EnFemme Style

Why do you need this? Don’t you have enough already? You can spend your money better on other things.” “I don’t know, I just know that I do. It’s important to me, and I can’t really say why. I’m sorry.” The truth is that I have always fanaticized about dressing in public en femme, and passing. I have never wanted to live full time as a woman, and I really enjoy being a guy and doing guy things. I also REALLY wanted to explore this feminine side and see what it is like dressing, acting, passing, and being publicly accepted as a woman. Not for any sexual thrill (although there has been some confusion in my life in that regard), but to just feel it, and know it is touching something in my heart to express it. So I had started collecting more “passable” items, without consciously pursuing a public outing dressed. I purchased a gaff, some nice shiny nude dance tights, heels, silicone forms and a pocket bra, and most recently, a wig. I had done some costuming drag the last couple years, but it wasn’t satisfying because although it was fun & sexy, it was still obvious I was a man in costume. I was just a boy in a dress. This last spring, being locked down and spending 24 hours a day with my wife and having time to deal with myself, I realized I needed to get my feminine side out in a more tangible way and finally learn to accept myself. Joining CDH was a first step to admitting I am actually a crossdresser. Filling out my profile, and just saying the words out loud “I am a crossdresser” changed my perspective. It changed how I viewed myself, and with the support of everyone at CDH, gave me the courage to start a dialogue with my wife. It was rough at first, but we had a few very good conversations and it has been a great opening up for both of us. The result of this long process finally came to fruition a couple days ago, on my birthday.

When my wife asked me what I wanted for my birthday, I said I wanted a day out en femme – shopping, makeover, nails, lunch or coffee, and to just spend the day with her as a couple girls having a great time together. That, and a bottle of Laphroaig scotch. I don’t think she really believed I was as serious about it as I was. We had tentatively planned the “day out” for earlier in the week, when I had a hair appointment to get my hair cut and to get my wig styled. When my hairdresser didn’t have time to style my wig, it actually was more deflating than I had anticipated. I called every salon I could find to see if I could get a makeover, and nobody was taking appointments due to COVID. I started reeling and losing my confidence, and at home my wife just didn’t seem into it. I just packed it in and gave up on thinking I was ever going to pull it off. That was Tuesday, and my birthday was Thursday.

Wednesday night, while we were in bed getting ready to fall asleep, my wife asked me again what I wanted for my birthday. I mustered all the courage I had and described what my perfect day out en femme would be in great detail. I said it would be the best birthday present if we could figure out how to make it happen. She agreed we should go for it! I set my alarm early.

I woke up and started the coffee. Made my daily protein shake, and sat on the couch reading CDH updates, sipping coffee & shake, wearing my rip-stop nylon dance warmup jumpsuit and dreaming about how the day would go, and hoping it would work out. I was terrified.

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I took my time shaving my face to get the closest shave I possibly could. Took a shower and although most of my body was already shaved, I took the extra step to shave my arms for the first time, which in retrospect was a very good decision to help with the illusion. I had been watching a few eye make up videos for getting heavy eyelids to look better, so I finally had the confidence to take my first shot at creating real-life passable women’s make up.\

I have some stage make up experience, and I am a very detail-oriented person, and I think I pulled it off pretty well. I was very nervous, because my actions this time would have real consequences as to how I would be perceived all day. It took forever (which my wife was happy to remind me of how many times I have criticized her about taking so long to get ready), but I was finally ready to get dressed and head out. My clip-on earrings were a challenge and was a source of some very real frustration, but we finally got them on. They hurt all day, but I loved having them on. I felt so feminine! We headed to Kansas City, with me in my wig, some feminine glasses, beige strappy sandals, pantyhose, a mid-calf a-line brown skirt, appropriate underdressing and forms, and a pink slim fitting man’s shirt with the sleeves rolled up. That’s the best “going out” outfit I had.

Part 2 next week……………


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Philma Bierstein

Mid-life CD. Professional, and I get out as Philma when I can. Slowly getting more comfortable in public, but not in my midwest mid-sized bigoted town... I have to travel about an hour to get to a town without aggressive criticism. Out to my wife and a few select friends, but closeted at work and in general, especially most of my family. Wishing acceptance was more normal, but knowing this region just isn’t ready for girls like us!
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Paula Malmborg
Active Member
3 years ago

Great Story and happy birthday I cant wait to read the next part

XX Paula

Rikki Edwards
Active Member
3 years ago

Nice story! Like so many people here, I identify with it very much. It took me a long time to admit to myself that I was a crossdresser and since I have done so I am much more comfortable with myself. I had my times where I put my dressing down to fetishism, for many of my younger years there was a sexual component for me. Now I dress because it just feels so right. I am a man who loves dressing as a woman, and I have no intention of transitioning, but like so many of us, I dream… Read more »

Cassie Jayson
Trusted Member
3 years ago

Thanks Philma, for your great story. I to am planning an outing the day before my birthday in 2 weeks. I have an apt at Ulta to color and style my hair! I debated with myself weather to go in drab or go dressed in fem. I believe I will go in fem and I can’t hardly sleep at night in anticipation. The only big thing I am missing so far is someone who can come with me to share my experience.

3 years ago

Wow, I read this story But first and foremost, I wish you a happy birthday, and I hope you will have the best present you can imagine for yourself I just want to say, that I understand your feelings and how I feel almost the same, even tho I can’t say that I’m experiencing the same as you do, but I feel the same way, I’m 25, almost 26 really soon And my feminine side is now burning with more passion than ever before, I don’t have the luck to have such a great SO, yet one that I thought… Read more »

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Vanessa Vanreed
3 years ago

Thanks for a great story sounds like you had a wonderful birthday

3 years ago

Dear Philma
That was a very encouraging story outgoing as Philma with the most loved person as a close friend which is your wife ,,,,I envy you ,,,Yet my wife has supported me for being a crossdresser with no going out since it is very dangerous to our family public image ( her reply ) may be because we live in Dubai and that is very conservative in accepting such behavior ,,,which is a Taboo

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