Sarah's Crossdressing Success Story – A Sister's Secret

Crossdressing Success Stories are real stories from crossdressers who have succeeded in an aspect of femininity. Their successes may be big or small, but their significance is important. Small successes lead to larger successes, and even though not all of us will be the perfect picture of femininity we all deserve to enjoy the crossdressing journey.

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.

Meet Sarah

My femme name is Sarah. I currently live in Fall River, MA. I am 53 and have been doing this since I was 13 – that may be the age when you figure out who you are.

Sarah’s Crossdressing Success Story

I started doing this when my sister dressed me up for Halloween (it was more of a treat than a trick,since i liked the feel.)  I went on to keep doing it, through service in the Army in the 82nd Airborne. I would rent a motel room for the weekend, and dress like I wanted.

I got married, but still liked to dress. Got seperated, spent 2 years dressing (at my own place and wearing frillies at work), then went to infantry combat in Afghanistan. When i came home I went to my sisters house where we exchanged secrets.

She told me she was a Wiccan – I did not care, freedom of religion ,right?  I told her about Sarah. She wondered where some of her underwear went!! As a result I spent a weekend with her as a woman. We went shopping for dresses, underwear, makeup, went out to eat (I can pass).

IT WAS FANTASTIC!!!!

It had nothing to do with sex, it was just about the bras, panties, stockings, garterbelt (HATE pantyhose), slip, skirt, blouse and heels(though i did learn how to choose shoes after that!) Still LOVE this!!!!!!!!!!!!!!!!


You can more wonderful crossdressing success stories such as Teresa’s first time passing. If you’d like to experience a crossdressing success of your own the world’s best crossdressing guide will give you the tools you need to look fabulously feminine!

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About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

20 Enlightened Replies

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  1. Crossdressers retreats | Gnboard | September 2, 2012
  1. Sarah says:

    to Jordyn Wayne-Stress induced my 6!We were like this to start with,we just went ahead and did the macho thing to prove we could,now that thats over,we can be who we want

    • Kenneth Ray Powers(Karen Rae) says:

      I was with the 101air born.did 3 tours in Vietnam
      .I go by Karen Rae.I started at a early age.am married and my wife loves that we are the same size.Idress all the time.

  2. Ragina says:

    Hi Sarah, I’m Ragina, and like you, I’m also a vet. Just wanted to say that I loved your story and wish you all the best.
    HOOAH
    My best to you, Ragina

  3. Sandra Jane says:

    Hi I have just come across this site I am a crossdresser my wife does not know so i have to dress when she is out one day I may get caught but thats the rixk I have to take.
    I am 56 years years old and have been crosssdressing since I was about 9 years old all the time in secrect

  4. Becki says:

    So nice to read about “success” stories from cross dressers. There are too many unhappy tales of woe out there.
    I am a life long cd with a very understanding wife who helps me with all aspects of my cding.
    She is especially helpful with makeup (eyes in particular) and accessorizing. I always look my best when she puts on the finishing touches.

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