Women crossdressing on Halloween

Today we’re blessed to share a crossdresser success story from Miriam, who looks back on many years of crossdressing to share two experiences that started it all for her. She’s a wonderful writer and I was touched by how her story combines trepidation and excitement with the loving support of a good friend.

If you’d like to share, please submit your crossdressing success story and I’ll post it on Crossdresser Heaven in a few weeks.

Meet Miriam

My story is not unlike others. I started very young and have been a crossdresser for over 45 years. I am happy to say that in all this past time, I have always enjoyed my femme side.

Miriam’s Crossdressing Success Story

My first real time experience came at age 14. Sandra Dee was the girl of everyone’s dreams, blond, blue eyed, young and sexy. I had fooled around with wearing high heels and such for a few years, basically what most kids do as they discover their desires. My neighbor and I got together for a Halloween party, she was 16 and very sweet and supportive, it was she who actually bought me my first pair of heels.

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We decided that I would go to the party as Sandra Dee, great poodle skirt, pink angora sweater, brown stiletto heels. I was blessed with very smooth femme features, baby face as they say, no sign of a beard until I was in my 20’s. I was a girl size 8, shoe size girls 8 and a 32 c size chest.

She did my makeup in light tones, red lipstick, gold drop earrings. I wore beige panties and a beige bra with padding, neutral toned stockings with a garter belt and had my nails done in red even though they were short. She did my hair up in a French knot, my hair was naturally long, Beatles era. We went to the party as cousins and not one person was able to tell I wasn’t a girl. It was a breath taking moment. Every chance I had to dress up I did, mostly with her clothes until I decided that it was time to buy my own.

On my 16th birthday I bit the bullet and went shopping. I went to a local dress shop to buy my first outfit. I was sweating all over, but I decided I had to do it. A young sales girl came over to help me and asked was I looking for a gift for my sister, I said no. I said it was for me. She looked at me and said you look like a size 8 or so and I said an 8 and that was that, I had broken the ice. I bought a beautiful blue outfit and one in red too. They had a great shoe department  and I bought 3 pair of heels. I tried them all on with the dresses to see how they looked and I was very pleased, so was the sales girl. The rest is history as they say. I have been buying women’s outfits since and will continue being my femme self hopefully for a long time to come.

Not every experience is always good, I was lucky. I decided I was not going to hide who I was, maybe that’s what made the difference. Self confidence that’s what will make it happen


Would you like to live a crossdressing success story of your own? Lean how to crossdress and pass as a woman.


More Articles by Vanessa Law

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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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Joanna Santos
Joanna Santos
14 years ago

So glad to see a nice inspiring story full of early self acceptance. Good for you Miriam!

14 years ago

Miriam, What an exciting night that must have been for you going to the prom. I’m sure you had a “tremendous” time. It sounds like you were dressed to the “nines.”….from hairstyle, to makeup, to undergarments, to dress and heels. It amazing that you were able to share this night with your date, David. I’m sure it meant so much to him – lucky fellow. And for the gg’s to never notice that you were a boy. I love wearing pretty formal dresses and gowns. It really brings out my “Patrice” side….isn’t it great being feminine?…oh, I forgot to say… Read more »

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