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

A sisters secret that she shares

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 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 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!

  1. Becki 3 years ago

    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.

  2. Sandra Jane 4 years ago

    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

  3. Ragina 6 years ago

    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.
    My best to you, Ragina

  4. Sarah 6 years ago

    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) 1 year ago

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

  5. Sarah 6 years ago

    What I intend to do is leave my former life behind,dont care to be a male anymore,want to become Sarah forever,need a place to go,transition,and restart a new life

  6. Sarah 6 years ago

    Thank you-never expected to turn out like this,but,life is full of surprises,and did in fact set out to prove manhood,only to find out that it is all a cruel joke-point being go as who you want to be-defy convention

  7. Joanna M Phipps 6 years ago

    One of the main covers for Transgender is for an MTF to take the hypermasculine jobs. Part of this maybe to try and prove to himself that he is indeed a man and can do as society expects. There maybe other familial reasons, such as a family tradition of military service that push the transperson in that direction.

    Even if on the outside they appear to be successful there may always be a sense of incogruity, yes that male did a good job but that isnt really me. There appear to be 3 courses of action,
    -transition early and avoid a life of confusion, depression and problems,
    -try the ‘I am male role’ and see if you can keep the female burried
    -retreat from life and everything else because its all too painful.

    Some of us have lived the lie for most of our lives and it doesnt get any easier with practice. I know of transwomen who, like me, began the journey to completeness in the middle years of life.

    It doesnt seem to matter when you transition as long as you, if you are trans, do so at some point in time so that you can enjoy how it feels to be complete.

    Love Joanna

  8. kimberly 7 years ago

    its funny how we are all macho in our ordinary ways…I too have been crossdressing for 25 years ..and Iknow i cant live without it

  9. Nicolle Robinson 7 years ago

    Lovely story. I am also in the military in Canada but am out to a number of people around me, mostly because of my online crossdress store, Genie. I also have a friend who is being helped in transitioning by the Armed Forces because the Canadian Army is much more accepting than a lot. We even have contingents in the pride parades and a CF LGBT group on Facebook. I am even hoping to have a CF recruiting booth at the crossdress and transgender weekend I am hosting in November called an alluring Affair (

    Although it can be a little tough, the freedom of getting out is worth it. I really enjoy attending the crossdress and transgender vacations and conferences because it is so much easier when you are with others who share the same interests. And, the nice thing is many of these include wives and significant others so they can particpate as well.

    • Ragina 6 years ago

      HelloNicolle, My name is Ragina, and I live in Georgia, USA. I am a retired member of the Army. I wish that our Army was as tolerant of the Transgendered as yours is. If it was, I’m sure I would have come out long ago. However. I’m sure that there are many here who would love to serve, but being transgendered they cannot. I would love to chat with you and share stories. If you would, you may e-mail me directly at:
      Good luck with all you do to advance the cause, and thank you, my brother-in-arms.

  10. Lynn Jones 7 years ago

    Arlivon: While the world isn’t always a nice place, things have (IMO) got better for TG folk. You’re right to be worried – who wouldn’t be concerned for a loved one? But it isn’t as bad as it used to be. Plenty of cross dressers are out or ‘go out’ and live to tell the tale with no more event than you or I visiting the shops.

    Take care

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Arlivon, my prayers are with you and your grandson. As Lynn said, the world isn’t always a nice place for those who are different. I do believe that with every passing year society grows up. We’ve seen tolerance slowly wash up on the shores of hate and injustice – and if we work together it will be a better world for your grandson to enjoy than we’re living in.

  11. Jordyn Wayne 7 years ago

    I’m an emerging crosdresser been married for 9 years, in the military currently deployed to Iraq. My wife didn’t take the news very well, and my military therapist thinks it is just astress induced phase, however i have been dabbling in crossdressing for 20 years now it wasn’t untill just recently that i realized how much i wanted to pursue it as a lifestyle. it has been a difficult time and i think with a little perseverance i’ll make it.

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Hey Jordyn,

      First, thank you for your service to our country, and for sharing a comment on Crossdresser Heaven.
      I’ve heard of very few crossdressers who just have a phase and move on, as much as they may tell themselves it’s just a phase at the time. Good luck with you and your wife, I hope you can work through any challenges together.

    • Ragina 6 years ago

      Hi Jordyn, my name is Ragina. I am a retired member of the Army, having done my 20, mostly National Guard, but I have 7+ active duty. I also have been where you are now. I hope that you are doing well. Enjoy your time there, and do try to meet some of the Locals, they really aren’t bad people, just a few bad apples in the barrel. I’d love to talk to you and find out what things are like there now. I was there in 03-04. I’m sure things have changed a lot since then.
      If you want to chat, you may reach me at :
      Best of luck to you and come home soon.

  12. ARLIVON 7 years ago

    Great story..who would imagion you could be in the service, but each to his own…i pray all will go as well with my grandson.i hate to think someone will hurt him because he is different..may someday i will have a sucess story of my own…god bless..arla

  13. Patrice 7 years ago

    Sarah, what a beautiful story. It must be so nice to have had a “girl-to-girl” session with your sister. It must have been so feminine for you. I bet your sister enjoyed helping you too become the woman “within”. I bet you told a lot of girl stories. You must have been so jealous when she started to develop. Looking back, it would have been great if she helped you with your first training bra. We (I say that as “sisters”) are lucky in some ways that we can share and express our feminine side. I know I wish I was born a girl. Keep in touch and hugs. Patrice.

  14. Lynn Jones 7 years ago

    > infantry combat in Afghanistan

    I love the fact that some of our number have some of the most macho jobs going!


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