Growing up, I knew that my mom had wanted a girl first, but she got me. I know now that a part of her resented the fact that I was a boy. My parents got divorced when I was 7 or 8. After the divorce, we moved quite a bit and mom wouldn’t let our dad see us for at least a year. It was always just my brother, mom, grandma and me. I remember my grandma griping at mom for the way she treated me. My little brother was mom’s favorite and still is. If it wouldn’t have been for grandma I know my younger years would have been a lot worse. She stuck up for me and taught me a lot. She is also the one that instilled the pride I have in my Native American heritage which made me who I am today.

My mother bought me toys and things that were for girls and bought boy stuff for my brother. I remember one Christmas we both got a cabbage patch doll. I threw a fit because I didn’t want a doll and got in trouble because mom said I had asked for it. Not long after that, I remember trying on nightshirts in the little girls department that she was planning on buying me. Needless to say, mom tried to feminize me as much as she could without people talking about it.

As I got older I never really had a lot of friends that were guys. I seemed to get along with girls better. As I got closer to being a teen, I found that I liked the bright colors and pretty things the girls wore. I wished I could wear those colors but boy stuff wasn’t colored the same so I never could. I felt like I should be wearing girls clothes and would sometimes wear stuff in, I guess you’d say, a girly manner. When I was in the 9th grade, I was going to a small rural school and was in the Future Farmers of America. We had an initiation where the guys dressed as girls and the girls like guys. It was awesome. A friend of mine lent me her black pantyhose, black skirt, and a beautiful red top. My hair was halfway down my back so my friend styled it and did my makeup. When I looked in the mirror, I just about fell over. Mostly because I was so pretty but because I really like how I looked.  This bothered me because I thought it was wrong to feel that way. I never got to dress up like that until recently. Up until I was 15, my mother never let me cut my hair so it was always long. When I finally cut it off at 16, she just about freaked when she found out.

I have always been and will continue to be an avid outdoorsman and survivalist, but I always wanted to wear pantyhose and women’s clothes. When I was 21, my first child was born. My girlfriend would have never been okay with me dressing so I didn’t. After my daughter was born and started to get older, I got the chance to paint my nails and do girly things playing with her. But that came to an end.

For the last eight years, I mostly lived alone or occasionally with a roommate. I still couldn’t bring myself to buy female clothes as I was always afraid they would be found. I was lucky enough to find my beautiful wife a little over a year ago and from the moment I first saw her, I trusted her with things I would not have told anyone. I don’t remember how our conversation about me crossdressing happened but she said she was okay with it and so I started wearing pantyhose, women’s socks, and other things. After I started dressing, I found another great thing in my life and that’s this website. Crossdresser Heaven has given me the courage to get in touch with the feminine me. At times I wonder if my wife has a problem with my dressing.  I get that feeling now and then. Although, we went on an out of town trip and I only wore women’s clothes (even went out in public). She had as much fun as me.

Though I enjoy being out and about as a woman, I enjoy being a man just as much. And that is the biggest struggle I have, wanting to be both. I know a lot of you struggle with feeling like it’s not really you when you’re dressed in men’s clothes but I feel like me dressed either way. I wish I could find the middle ground and be able to dress either way but for the time being the only person outside of the members here that know is my wife. I’m hoping to tell my kids soon but I don’t know how that will go. Guess that can be my next article. Until then I want to wish all of you courage on your journey. May you find a place in this world to be yourself whoever that may be and may the spirits keep you safe, secure and happy in your journey. Chi hullo li ai okla.

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Ivy

Howdy I’m ivy I’m 40 and starting to dress more

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15 Comments
  1. Hi Ivy! Welcome to CDH. I sincerely wish that you find your dreams come true and go about dressed as you wish. Don’t let anyone tell you different. It is your life. Bon chance mon ami! All the best. If I may be of assistance please let me know or any of the other sisters here.

    hugs…..Lady Veronica

  2. Gisela Claudine 4 weeks ago

    Thanks, Ivy. I’m happy for you. I really enjoyed your article. I also think that I’m happy the way I am. Now much more than ever before. I think I have found the balance in my life.
    Cinnamon kisses,
    Gisela.

  3. Joseph Escobedo 4 weeks ago

    To all my sisters is so overwhelming to keep reading your articles gives me the courage to enroll on CDH . at first time I was afraid of my wife knowing my desire to dress and I’m still doing it only when possible , my first time dress up and getting caught was at six with my friend’s sister dress it was a red dress with tight sipper and white petticoat , my parents came sooner than expected cause my oldest brother was outside playing and he only saw me playing with toys, but watching him from the window he wasn’t aware of me and in an instant door opened and I got caught and punishment by my Dad . From there I never understood why I was told never to wear nothing girly , when started was one night all my brothers were asleep and I try one of Mom’s dresses I put the sipper all the way up then I hear someone at the door it was Mon and Dad from a visit to Grandma’s house , I barely had a chance to get to bed and cover with my blanket, Mon came and helped me tuck in my blanket, that was close , one other time was at 14 when I got home and nobody was home I went to Mom’s wardrobe and got one of her dresses and look at one of her petticoats I feel fascinating and forgot that my friends were waiting for me the show at the door knocking and couldn’t get it off I went to my bedroom and on a corner I hide but someone kind of saw me I was hiding on that part I could change but I love the feeling of that crinoline from that moment I new I was to love wearing anything under my male clothing. Thanks again for your stories my sisters. Addrianna.

  4. Hope Clark 4 weeks ago

    I love being both too, hun. Blessings to you as you enjoy both sides of your gender.

    Hope

  5. kelli 4 weeks ago

    i knew my mother wanted a girl first and have wondered thru the years if her feeling that way when i was in the womb is the reason for my love of women’s wear.She didn’t do has your mother and push female attire at me the only thing she really ever did was to enroll me in a ballet class which because of the living situation at the time was the start of my wearing female clothes for pleasure at eight years old and my first time to have sex with a girl the only thing i want relay to you is to think more about telling your children though i know they will still love you not real sure how their respect will go good luck Kelli

  6. Leslies Ann Gray Girl 4 weeks ago

    Hi Ivy I know how hard this is to live like , witch way do we go . Good luck with your life as fem , it happens one day at a time.Love ya Leslie

  7. Angie Walker 4 weeks ago

    Hi Ivy,
    I can totally relate to wanting to enjoy both sides of yourself. After all it’s both the masculine and feminine sides that make you who you are. I think it’s wonderful that you have a supportive and understanding wife.
    Angie

  8. Victoria Egger 4 weeks ago

    I know how you feel. There are times when all I want to be, is a woman. But here are time Iam just as happy being a man.
    Love,
    Vickie

  9. Julie 4 weeks ago

    Hi Ivy
    Yes I can totally relate to your life. From the first moment I
    Put on one of my mother’s dress at the age of 12 I felt more like who I was meant to be. A female!! But being one of 3 boys my parents had I never told anyone and felt there must be something wrong with. I’m 71 now and have lived as a man, married and have a wonderful family but I still to this day wish I was a female.
    Thanks for sharing.
    Love
    Julie

  10. gloria 4 weeks ago

    Hi, love your story too , sound like me but full time cross dresser at 69 now . love Gloria

  11. Leonara 4 weeks ago

    Welcome Ivy,
    Thank you for sharing your personal story..
    it’s an inspiration for all of us. We are glad at that you embraced CDH we are here for you.
    Leonara

  12. skippy1965(Cynthia) 4 weeks ago

    Great story, Ivy! I’m sill figuring out my own path but always love to hear others’ experiencing!
    Cyn

  13. Rozalyne Richards 4 weeks ago

    Hi ivy i think most or all of us on this site have experienced the same sort of thing you have been through in finding our true self’s, some of us have still got a long way to go, I’m happy that you have found your soul mate and can be who you want to be best wishes Rozalyne x

  14. Hi Ivy – I can totally relate to enjoying both sides of yourself. I’m happy as April, but I’m also comfortable in guy mode, which is where I spend 95% of my time. Finding a balance and acceptance of both sides of your personality can be a long journey. I’m still on mine, but getting closer all the time.

    Hugs,
    April

  15. Bianca Everdene 4 weeks ago

    Thanks for your story Ivy, I am sure many on this site can identify with the difficult times you have come through, and I am sure come through to become a stronger wonderful person. You are so lucky to have found a soulmate with whom you can share your feminine side. For many this site is a place where we can truly express ourselves.
    Love
    Bianca

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