My trip down Crossdressing’s Rocky Road

I wanted share my storyn  Some of what is to follow might be upsetting but there is a happy ending …

I was born August, 1970 in Manchester, England to older parents. I was an only child, had half-brothers and sisters from my parent’s previous marriages, but they didn’t live with us as they were much older. My father ran his own business. I was brought up in an affluent part of Cheshire called Hale. The area was nice, but it was a lonely as I had no siblings around and only a few friends.

My mother had a violent temper, brought on because my father was a womanizer who stayed out until the early hours of the morning. I was subjected to their reoccurring arguments. I went to school with bags under my eyes over the lack of sleep and the worry it caused me. My mother was not maternal by any means.  I had to make my own breakfast and cross three busy main roads at the age of six. It was a tough life, even though I lived in a nice area. At times, my mother would totally lose it and beat me with a high heel shoe or anything else she could get her hands on. I continued to show her love and affection in return.  I didn’t know any better.

Unleash Your Inner Woman

My parents split up in the early 1980’s after he told her that he didn’t love her any more (I don’t think he ever did.) The feelings of emptiness and rejection grew stronger inside me. I couldn’t escape the thoughts of why this was happening.

My mother and I lived in Altrincham, Cheshire for a few years, where things calmed down. She met a man who lived some distance away in Bolton, Lancashire. Eventually, we moved there and I had to start at another school. I found it hard to mix with the others because of joining half-way through the third year and because I spoke differently as I didn’t have a Lancashire accent.

It was during this time I began to wear women’s clothing. I tried on a pair of my mother’s panties, but I didn’t fully understand what I was doing and why it felt good. With the supply of available clothes very limited, I didn’t often get the opportunity wear girls clothes. After my mother broke up with the man from Bolton, I once more found myself moving, this time to Great Sankey in Warrington, Cheshire. It also meant another school. I attended three different secondary schools, and because of our moving, my education was inconsistent and difficult. This is where my story becomes interesting…….

After moving to Great Sankey in Warrington, we lived in a row of four terraced houses. Living next door to us was a very beautiful woman and lovely man, both of whom I got to know very well. I was 15 at the time, and my feelings of wanting to be a part-time female were getting stronger. It was made worse by the beautiful woman next door, who happened to be from Finland. I had no female clothing I could wear; my mother’s knickers were too big for me. I couldn’t buy them from the shops without money or courage. I had to do something. I have never done it since, and I regret doing it, but I took something off a washing line! It was the woman’s underskirt from next door, and I cherished it for many years to follow. Her husband came round and informed us that his wife was missing some clothes off the washing line, (I only took one.) My mother found it quite amusing that there was a knicker-pincher about. I kept quiet because the humiliation would have been worse than the confession.

Over the next several years, I managed to scrape together a few items of female clothing to wear every now and then. I frequently wore the underskirt in bed.  It just felt so silky and the fact it had belonged to such a pretty woman made it that much better. I believe that my mother never knew about my crossdressing. She passed four years ago, and I am not aware that she had any idea.

By the time I was 30, my crossdressing had really taken hold of me. I moved out on my own and met a nice woman who is now my wife. When we first met, I didn’t confide in her about my crossdressing.  It’s not really a normal topic of conversation, is it? Trying to find time for crossdressing became difficult because she had two young sons at the time who needed lots of care and attention. I was restricted to wearing women’s clothing only at night and hidden under my pajamas. As time went by, my frustrations built up because of my desire to be female. I was supposed to be the man, responsible for holding everything together in the family. The boys grew up and became independent teenagers. I had time to spend on my own, upstairs in the bedroom, where I could dress up and be reasonably safe from being caught. My female clothes were still very basic. I was getting bored of them, as you might imagine, wearing the same ones for years.

It happened five months ago, as I felt I couldn’t keep holding back the stress of keeping my secret. The deceit, the hiding, the wanting, the needing, all became too much for me so I confessed to my wife. I told her what had been going on all these years and what my feelings were. Surprisingly, she wasn’t the least bit amazed, saying that she’d suspected something. It had been the little things, various items of her clothing being moved or missing altogether.

My story, as it stands now, isn’t perfect but it is a start. My wife now knows and she is reasonably agreeable for me to pursue my interests, within reason. She’s not willing for it to become an obsession but she is happy to interact with me every so often. I tend to model myself more as a girl at age 16 rather than a woman my age. I have a superb wardrobe with lots of pretty clothes – short skirts, tights, jumpers, leggings, pajamas, etc., all the things I could only dream of having a few years ago. I’m currently experimenting with make-up (with varying degrees of success.) I have three beautiful, long blonde wigs that I cherish and properly look after.

My road into crossdressing has been a rocky one. It had been mostly done in secret and in fear of being caught, up to recently opening up about my feelings and sharing them with my partner. There is still much to be done. I need to show my wife that I still love and cherish her, as I did when we first met. For me, the biggest lesson I’ve learned has been to stop selfishly thinking of only myself. My wife and kids come first and they always will. Whether Fiona continues to be as free as she is now or is once again constrained, I am and always will be a crossdresser for life.

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  1. Brianna Rain 1 week ago

    Hi, Fiona. Thanks for sharing this.

    Hugs,
    -Brianna

  2. Natalie Elaine 3 weeks ago

    Such a wonderful story of your life to date filled with so much. I hope you go from strength to strength and find a level of acceptance with you wife that is so hard to achieve.

  3. Mark Chadwick 3 weeks ago

    That lovely story Fiona about crossdressing and I love your story and me same like to dressed up woman clothes sometime I sneaked my mum wardrobe to get knickers, tight and dress to wearing it’s was great and I’m enjoy my mum clothes then I put all backto wardrobe

  4. Karl Schmidt 3 weeks ago

    Thank you for sharing your story. It is encouraging to hear that others have had the courage and strength to openly accept who they are.

  5. Torry Burns 4 weeks ago

    We all have different stories. My crossdressing started as an expression of my homosexuality. Now a lot of gays don’t like that type of confession for they want to say your not gay if you want to dress up and act like a womanl Bullshit! All crossdressers are not that way but I am. That’s part of my story.

  6. Jessica Rabbit 4 weeks ago

    Thank you for your story Fiona, although my story was not the same as yours, I can definitely relate to the last part. But I think it’s important for us to each get our stories out there (I’ll post mine one day) as it’s these stories that made me feel that I’m not alone, that it’s OK to be the way I am and it shouldn’t be something to be ashamed of.
    As for worrying about your femme age, don’t limit your happiness because of a ‘you shouldn’t be wearing that thinking’ I think we all have had enough of that . I’m sure you look great in it, and if not who cares, it’s part of who you are. Own it girl!
    Jessica x

    • Author
      fiona moss 4 weeks ago

      thank you very much Jessica, those are the true encouragement words I want to hear. as said before, I worry, I worry about everything! the last thing in the world I want is to be rejected because I was doing something someone may have thought inappropriate. I fully realised that it may make some people think that’s a bit strange an older man dressing as a teen girl but I do try very hard and choose my clothes age appropriately. I thank you so much again for being understanding, it really means the world to me.

      love fiona xx

      • Stephanie Rae 4 weeks ago

        I do not find your interest in teen girl clothes strange. That age has a lot of fun flirty girly clothes, and it’s an experience I would wager most of us missed out on. So I get it. Thanks for sharing your story ❤️

  7. *skippy1965(Cynthia) 4 weeks ago

    Lovely article, Fiona, and congrats to you and others whose spouses accept or at least tolerate heir dressing. My ex did not but we are still amicable 13 years after the divorce. Thanks for sharing your story!
    Cyn

    • Author
      fiona moss 4 weeks ago

      thanks cyn for your kind words. I am considering a follow up article regarding what happened after the kids grew up and after I told my wife, how I felt etc. I need to give it some careful thought!

      love fiona xx

  8. Marianne 4 weeks ago

    Thank you Fiona for sharing your journey with its ups and downs. I understand it must have been hard to return to some of those memories. I’ve been writing down Marianne’s memoirs, but they are much to long to publish here.

    • Author
      fiona moss 4 weeks ago

      hi Marianne. thanks for your feedback, it was certainly hard to re-live some of the memories as over time you try to forget and move on. it is true to say though, that I still think about it from time to time. maybe you could publish a series of articles if you feel just one would be too long?

      fiona xx

  9. Mandy Cross 4 weeks ago

    A heart felt article Fiona, sad in parts and can certainly relate to parts of it. Thanks for sharing this, it certainly sounds like you have had a rocky road but are now strong in your conviction of who you really are, some of us never find that peace, I’m glad you are getting there. Mx

    • Author
      fiona moss 4 weeks ago

      hi mandy. so many people have said they can relate to different areas of it. I thought I was the only one. it puts life in perspective knowing others have also had a hard upbringing or similar. I hope that you also gained a degree of comfort reading it too as that was my intention to help others come to terms. take care, mandy.

      fiona xx

  10. Sammy 4 weeks ago

    Fiona dear… Thanks for writing, for sharing about yourself. Your article grabbed hold of me, because in every paragraph I found an echo of myself, either as the child or as the parent…
    Btw in regards to your forum post: I think a lot of us see our feminine side as at least somewhat younger than our masculine…ask me in drab and I’ll tell you I’m 40. Find me en femme and I’ll swear to you I’m 31

    • Author
      fiona moss 4 weeks ago

      hi Samantha. it seems a lot of people can relate in parts to my article which, I admit, I did find suprising. you think that only you have suffered in the hands of someone else when in reality it seems to happen a lot. I am hoping the article will at least bring comfort to our members that have suffered similar pasts and hopefully gain some comfort from reading it and realising that they are indeed not alone. regarding my femme age, I just worry, I am a born worrier, I always worry what people think or say, how they might react, if it is acceptable etc etc. some people can be very unaccepting of such things even though its perfectly innocent.

      fiona xx

  11. Michelle 4 weeks ago

    Thanks for sharing!

    And am I the only one that read that voiced in a proper British accent?

    Michelle
    xoxo

    • Mandy Cross 4 weeks ago

      You aren’t alone Michelle, I can do a pretty good Manchester accent too! Mx

    • Author
      fiona moss 4 weeks ago

      lol michelle and mandy. bolton accents are really strange, me originating from south Manchester, we spoke ‘posh’. I then find myself years on with a fairly broad bolton accent with a bit of south Manchester thrown in for good measure! it makes a very weird combination lol.

      fiona xx

  12. Lisa watson 4 weeks ago

    Interesting story they all seem to be that way.

    Thank you for posting as I could relate to a lot of it.

    Lisa

    • Author
      fiona moss 4 weeks ago

      hi lisa. just another hard luck story lol. at least though, it has a good happy ending. I think the only downside to it all is its made me nervous around people, I thought I should have grown out of it by now but it could be a whole lot worse.

      fiona xx

  13. Michelle Liefde 4 weeks ago

    Hi Fiona, thank you for writing your story. When we share our pasts with each other, it can only help each of us to understand and grow in our community. And as someone whose wife knows and is supportive, I agree that always showing your partner that love and cherishing what you have made together is so important in keeping each other happy. So I am rooting for you, my dear CDH sister!

    Hugs,
    Michelle

    • Author
      fiona moss 4 weeks ago

      hi michelle. so nice to hear your words of encouragement and support. I certainly have had it hard but I am sure some people must have had a tougher time than me. its nice to have an insight into other peoples lives, even if its just to make you realise that you really are not alone.

      fiona xx

  14. Jade Smith 4 weeks ago

    Hey, I also moved around a lot when young, albeit for different reasons: my dad seeking promotions. Also left largely to my own devices as my parents were always busy with something work related. I’m also familiar with your locations, being a Northern soul, though the Eastern side. I’m glad you’re beginning to find happiness and fulfilment. Pm me if you wish.

    • Author
      fiona moss 4 weeks ago

      hi jade. it is so tough moving around as a young child and leaving your friends behind due to no fault of your own. I would like to say it has ‘toughened me up’ but it has not. I became very wary of people and did not make friends easily, not that I am hard to get along with, it was simply a matter of ‘trust’.

      fiona xx

  15. Terri Anne 4 weeks ago

    Hi Fiona,
    Such a beautifully writen article. Thank you for sharing your tearfull story. My life has never been so hard as yours. Even though My mum was of a similar nature and we moved fairly often.
    Bless you and your new journey love.
    -Terri Anne

    • Author
      fiona moss 4 weeks ago

      hi terri, thank you so much for your kind words. its really nice to be thought of. the story is sad but I thought it was apt to share a story which quite a few I suspect, can relate to in parts.

      fiona xx

  16. PY Marshall 4 weeks ago

    Hi Fiona,Thank you for sharing your story with us .I felt the emotion In the letter and have read it several times.This is a special place for us all.For the first time in my life i am able to relax and speak freely and i hope that by joining ,It will do the same for you.Good luck on your journey Py xx .

    • Author
      fiona moss 4 weeks ago

      hi py. I am happy you enjoyed reading my article and I was very emotional putting it all together as there were things in there I would rather forget. cdh for me has been a huge support, certainly after suffering many years in silence.

      fiona xx

  17. Alice b Carpenter 4 weeks ago

    Glad you found yourself, i must put my story down one day,
    Its getting over that hump i think and having support from your partner. Support makes all the difference hugggs

    • Author
      fiona moss 4 weeks ago

      hi alice, yes I would certainly agree that its a massive relief, even just to tell your partner, at least its then all in the open. I hated keeping secrets from her. regarding your story, you must do it one day, it was very emotional for me to re-live my past as I try my best to forget it but at the same time I felt people needed to know my reasons and also my background. it sure has been a rocky road!

      fiona xx

  18. Bianca Everdene 1 month ago

    Thanks for sharing your story Fiona. You are in good safe company here. A Rocky Road indeed, life is a rollercoaster, and if you have experienced the lows, the highs become so much sweeter, an ability to appreciate the simple pleasures such as a beautiful sunrise, or the feel of a silk underskirt.
    This site allows us to share stories we would probably not be comfortable sharing with others face to face. Many of us can empathise with these hardships. It was a kind of therapy for me, to finally open up to others about crossdressing, and finding thousands of others who share this love is comforting, knowing we are not alone.
    Glad you have found happiness, and the chance to occasionally indulge the Fiona in you.
    Love
    Bianca

    • Author
      fiona moss 4 weeks ago

      thanks for your kind words gabriela. I felt that other members deserve a view into my past and what eventually brought me here. it has been an uphill struggle and many questions, fears and worries along the way. there is no doubt I am totally at peace here knowing (hopefully), I am accepted. the biggest fear of mine, really, was my femme age, I seriously thought many would certainly disapprove thinking I was some sort of weirdo. all I can say is its perfectly innocent and its an age I feel most comfortable with, I suppose in a strange way I am trying to claw some of my lost childhood back but in a femme way.

      fiona xx

    • Author
      fiona moss 4 weeks ago

      thanks Bianca. its lovely and reassuring to hear that I am in safe company. my biggest fear has always been acceptance and what other people will think.

      fiona xx

  19. Gabriela Romani 1 month ago

    Fiona,

    Thank you for sharing your story with us. I know you have touched our hearts as many are able to see themselves in that lonely child looking for affection at some point in our lives.

    I so hope you will be able to keep your marriage and that you will continue discovering more about who you are, but above all, I wish for a smooth road for you from now on.

    Hugs,
    Gaby

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