Marys comes out a a crossdresser with her three sisters

You look at all those perfect transgender woman in despair. Hair and makeup expertly done, a figure to die for, clothes hugging them like a long lost lover. ‘Surely crossdressing success is out of reach?’ you ask yourself, while analyzing your flaws in the mirror. Without realizing it you’ve ignoring all the success you have right in front of you.

Crossdressing Success Stories are a regular feature on Crossdresser Heaven, featuring successful crossdressing escapes of your average transgendered male. You don’t need to look like a beauty queen to experience crossdressing success!

Meet Mary Ruth

My en femme name is Mary Ruth. As with many others, my first recollection of desiring to dress in girl’s clothes was when I was very, very young. In fact, I vividly recall the day.

Mary Ruth’s Crossdressing Success Story

As both of my parents worked outside of our home, my sisters and I were often cared for by a baby sitter. One day our sitter was helping me get dressed (that is how young I was!) and asked me which tee shirt I wanted to wear. She had two for me to select from. One with short sleeves and the other with very thin straps – just like the one my older sisters wore. In my heart I so desired the one like my sisters, but embarrassment stole the day. I selected the “boy’s” tee short.

Join Our Community-cdh

With three sisters (one younger and two older), I have always had ample inventory of clothes to borrow (bras, panties, stockings, makeup, etc). The closes I ever came to going out dressed “en femme” was one Halloween when I was perhaps 8 years old. My sisters wanted to dress me as a girl for Halloween. I was overwhelmed with the idea. My two older sisters seemed to enjoy the transformation process. After a bit of work on their part, I was fully dressed, makeup and all. Then came the hour to go outside to meet our friends, and once again, embarrassment stole the day. I caved in at the thought of being teased by our friends for being dressed in “girl’s clothes.”

Throughout the years, as a situation would allow, I would dress en femme. Having to do this covertly, for fear of being caught, I only dressed in part. That is to say, as an adult, I have never dressed 100% en femme. I was forty years old when I purchased my first woman’s garment – a bra. Yes, I have made many purchases since then…and yes, I have later throw them out when the guilt took over!

I’ve been married for over 34 years and have a really great marriage. I did tell my wife about my CDing 8 years ago. It blew her away, to say the least. Even though she has tried to understand, she does not like the idea of it. So, I stay very deep in the closet. Fortunately, my wife is on a trip with her sisters. So, today I am 90% en femme (no wig and very little makeup). Yet, I am 100% enjoying the time to express myself 🙂

Thanks for reading,
Mary Ruth

P.S. Do you have a real life crossdressing success story you’d like to share with the readers of Crossdresser Heaven? It just takes a moment. Write down your success story (500-750 words), include a brief introduction, your femme name and optionally a photo. Send this to me at and I’ll post your success story on Crossdresser Heaven!


More Articles by Vanessa Law

View all articles by Vanessa Law
The following two tabs change content below.
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.

Latest posts by Vanessa Law (see all)

0 0 votes
Article Rating
Inline Feedbacks
View all comments
Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?