I crossdressed on a dare

Crossdresser Success Stories are stories from real crossdressers who have succeeded in accommodating their inner woman. Some successes are spectacular, others are more modest – all are important breakthroughs for the wonderful ladies who experience them.

Share Your Crossdressing Success Story

If you would like to share your crossdressing success story, please email me at vanessalaw@crossdresserheaven.com and let me know you’d like me to share with others. Please include:

  • Your femme name
  • A brief introduction (1-2 sentences about where you live, how old you are and such)
  • Your story (if you go over 700 words I’m going to edit you down :) )
  • Optional – A photo of you (no nudity please)

I’ll post your story on Crossdresser Heaven within a few weeks. You’ll be famous ( 🙂 ) , and you’ll be doing a good thing for everyone in the crossdressing community.

Meet Liberty

I am 53 years old and experimented with cross dressing for over 20 years.


Liberty’s Crossdresser Success Story

At first it was just a dare for a fancy dress party where men dressed as women, women dressed as men. So my ex wife did the business on me and we even borrowed a wig….and she made me into a tarty type women. At the time I thought wow I actually like this, putting on a suspender belt and stockings and a bra stuffed out with tissues to give me shape , I just felt good, and the swish of a skirt around my legs was so nice. I secretly love the way I looked and the shape I had.

After that I experimented in private alone and it started to dawn on me I was a transvestite, it was more than just cross dressing a bit…I wanted to feel and look like a proper woman, and felt so happy and comfortable when I was fully dressed. I would spend whole afternoons by myself dressed to the max .

I got divorced (nothing to do with that) and started to buy the most pretty things I could, from every day clothes to silk night wear, one shop assistant in an exclusive lingerie shop guessed what I was doing and asked me if they items were for me…so I just said yes…no problem she said…we get this a lot….and she started to advise me on what looked right and what did not……all my underwear was the best quality. Dont buy cheap it is false economy.

Then I met another lovely lady, (at a heavy rock concert) and we went steady and talked about so much and fell in love. Eventually the natural thing happen and we wanted to marry, but I decided I’d had enough of my secret side, so I told her, she never batted an eyelid, and just said that’s fine by me, she’d had another male friend exactly the same and it never bothered her…….she said, why should ONLY women know the feel of silks and nice clothes and if more men tried it they may find it a calming influence, and real chill out, especially after a serious hard and stressful day at work…….and she encouraged me then and there to cross dress anytime I felt the urge. She has taught me how to put to put make up on tastefully and the right sort of clothes so I look right……for a present she even secretly bought me a long natural hair wig. And she helped me choose a pair of proper synthetic boobs. So now when I am dressed up I do look the part with a beautiful DD curve up top, they were very expensive, made to measure and even skin toned to me and even give me a cleavage…..but you get what you pay for. And I can wear them all day without aggravation etc

So now my lovely wife and I spend what we call girly nights together, and when I transform I am known as Liberty…..I come home from work, and most evenings totally transform myself in a woman, I am still as heterosexual as the next man……and have NO gay or Bi-sexual desires…..I just love to dress and act as a lady. So what would you call me???

My Next step is to go out dressed like this…..but I have not plucked up the courage to go public….maybe one day. My wife tells me I am as natural looking as you could get and not many would notice I was a man especially when she applies make up on me, she really is an expert at hiding all my male facial lines.

I am one lucky guy to have such an understanding wife, but coming clean before we married was the key, so all you secret cross dressing men out there, tell your partners, you may well be surprised at their reaction……my wife feels she has a loving macho man husband and also the best girl friend she could ever want all rolled into one.

If you’re struggling to find the word’s to say when you tell your partner I highly recommend you read My Husband Betty and I Married A Crossdresser. You owe it to yourself and your wife to be prepared before you tell her.

Good luck!


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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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Mandy Bird
Mandy Bird
15 years ago

What a great story, Liberty!

While I didn’t get the chance to tell my wife before we got married, I did shortly after – and it was the best thing I’ve ever done. She helps me shop and do my makeup and it’s soooo wonderful having a real girl to help out! I never would have come this far without the support of my wife.

Best wishes!


15 years ago

Dear Liberty, Mandy,
You gals are so lucky and I feel so happy for both of you.
I am not as lucky. I discussed with my girlfriend on this and she could not accept who I am. She can only play ignorance and avoiding this topic whenever she can :,(


12 years ago

OMG that story is so beautiful just wish it were me, you lucky girl!!!! I hope you two have a wonderful life together!!!

12 years ago

Well hello there Elaine hon.

12 years ago
Reply to  Elaine

Hi Elaine, any chance you can chat with me, would love to hear from you.

Would love your thoughts, please comment.x
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