Crossdressing success story - caught in the middle

Dear Readers,

Today’s crossdressing success story comes from a lady who is caught between a life with a loving wife of many years, and her deepest longings. My heart goes out to her, that she may find a tranquil agreement that allows both her and her wife to be who they are. If you’d like to contribute your own crossdressing success story send your humorous, emotional, joyful, courageous and heartfelt stories to and I’ll share them with our community.

My Story,

Sometimes beginning at the middle is a good place to start because that is where most stories are composed.
I am where I am, I do not know where I will be in the future. I have some recollection of where I have been – you know how it is as you get older!

My cross-dressing story has been evolving recently. I recently went to see a GP, then a Sex counselor then a psychiatrist. Interesting discussion; however, I really got nowhere with understanding why or what to do?

I am married with a wife who is aware of my need; but is not  accepting. We have been together for over 30 years. I only told her about my need  2 years ago. I have been lucky to the extent that she has not left me; however while she accepts the situation she is very emotionally against it!  Sexual relations have been difficult since my revelation. We have 2 children both of whom have left home. As far as I am aware I do not believe any of my friends or relations, apart from my wife, are aware of my dressing crossing.

We have agreed that given the time we have been together and the difficulties in getting another partner, staying together even with ‘issues’ is better than not. We have a session with my psychiatrist planned in a few weeks. We would like to explore where we might go with our relationship which we are keen to develop further rather than just let it lax.

Each week I have a day off from work while my wife is off with her work. I am Jane then. I dress, put on makeup and go out. Shopping for clothes, makeup, to the movies, the art gallery or just a coffee is my day out as Jane once a week. I would like more; but given work and other commitments it is difficult. Sometimes if I am away with work intercity I have opportunities to dress.

I look forward to ‘my day’ as Jane and see it as an opportunity to throw off my male shackles and immerse myself as a woman. It is a wonderful feeling that is hard to explain; but I have come to accept that this what I need to do and continue to explore and develop….the story continues.

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  1. Vivianna 7 years ago

    Jane; My first wife was the same way. I discussed things before we ever got married and I hoped her position would change. It never did, and our relationship died. This was not a bad thing, it gave me the time to find myself, love myself, and eventually go out and find that person who loved me, all of me. Now I have a wife, and children, and one hell of a wardrobe that I feel comfortable and fun wearing whereever and whenever I like. I wish the same for you and everyone else. Ending is harder than starting over.
    Ms Vivianna Van Gogh

    • Author
      Vanessa Law 7 years ago

      Wonderful sweetie! Oh it’s such a blessing when things work out like that. Sometimes life throws curve balls at us because we’re playing the wrong game.

  2. Tiffany Brown 7 years ago

    It was amazing how much my story mirrors Jane. Married nearly 30 years, sadly I kept my life secret until she discovered a couple of years ago. She hates my dressing and while I am keeing true to her I struggle with finding balance. She didn’t sign up for this so I don’t blame her for her feelings, not sure how this gets better.

  3. Isabelle Williams 7 years ago

    I have only been with my wife for twelve years,i should have told her when we first got together,but i didn’t;needless to say she was not happy at all when i told of my long desire to be female,and my dressing up en femme.We are still together,but she in no way supports or likes Isabelle,i only play at being Isabelle when she is either working ar away visiting;oh,what a life.

  4. Robin Michaels 7 years ago

    Hello Vanessa, Like the girls above, my story is close o the same. Married over 30 years, been a closeted CD, since my late teens(over 50 now). I miss my time being Robin, and used to also, enjoy that one day a week, by myself. Schedules canged, no day for Robin anymore. And yes, I told my spouse of my desire, she’s ok with me in panties, but gets turned off by anything more. And, she’s afraid of me becomming “gay” and leaving. Well, I could not tell her I’ve always had the desire to be dressed as Robin, and “playing” with another CD. And, I plan on finding that “special” CD,TV Girl friend, to be intimate with. I pray that this can become a reality, soon. Our “love life”, has been non-existant, for over 2 years.
    I wish you good luck, and keep ahold of your dreams. XOXO Robin

  5. Blake 7 years ago

    I really think we should be asking THIS question instead > “Why Do WOMEN Cross dress” ? Because look what alot of them wear and styles that are after mens. For example…Boy shorts undies for women with a fly were modeled after what gender?………oh yea,it was from the MALE’s dresser.And WHY are we not making a issue of that ?

    I saw a program on a tv news cast not long ago,about this boy/guy that like “female” things,and like to wear skirts and such.At the end of the report,they had a Dr.(psychologist) on and they were going to interview him as to why males like to wear female clothing,(like it is a sickness on the mind type
    a thing)But we NEVER hear about if a female likes to wear guy clothes,shouldn’t we be calling a Dr. for her as well for her wearing guy clothes ? It is sexist and hypocritical.Maybe the equal rights we had only apply’s to women and not men ? As we all know that females were not aloud to wear pant’s til the early 1930’s/war time.Look at pictures from the 1930′ and early 1940’s….Women wore dresses,not skirts.

    Hey,hows it going Samantha ?

  6. Gloria Janine 5 years ago

    I am a lot like you. I told my wife of over 30 years 12 months ago. Was not real happy with it but accepting things. The kids are grown and married off. I have been out en femme shopping with my wife and my sister. At first she wouldn’t be seen with me dressed, but now helps me pick dresses whilst I am out dressed. We talk a bit about fashion and other female trends, make up etc. I have been wearing false nails for almost a year now with regular appointments at the salon, I have even been there en femme. I live at home almost 24/7 as a female. Only my sister and a few very close friends know I crossdress and they accept it but are yet to see me dressed. At this stage my wife only knows that my sister is aware. Unfortuneately in my circumstances the more often I dress the more I desire never to change back to male attire. Hence now I am on that rollercoaster of emotions. But loving every minute of my femininity. Best wishes for the future.

  7. Dave Huck 5 years ago

    Luv ya Jane
    Happy Halloween. I was Dave yesterday but Daisy tonight.
    Dressed in Long Beach

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