My life as a crossdresser didn’t come easy at all at first. I knew at age 15, I was feminine and kept it in the closet. Being the youngest of 3 sons, I didn’t see myself as one. There was an issue to it, my parents were bias on LGBT people. They had their opinions on it. Some of it was good and some were bad. I remember them talking about it and never mentioned me. I was mentioned when I wasn’t around and was never told until my mom’s death 4 years ago. Other family members told me my dad whom passed 5 years ago and my mom thought I was transgender or gay. I was a little angry and asked why it wasn’t mentioned to me. They thought I was too young at first and wanted to keep it a secret.

First time crossdressing was when I was 32 years old during my marriage to my ex-wife. It was private when my ex-wife wasn’t around. I didn’t want her to see it.  I didn’t know how she would react to it. I never went into her closet.  I didn’t want her to suspect me going into her closet at all. I would go to second hand stores and buy the clothes. It was fun finding dresses.  I loved shopping for tops, jeans, and skirts. I brought everything home keeping everything in the trunk until my ex-wife would leave. I never wanted her to ask about it which she was nosey at times which I hated. I thought she would not find my stash of women’s clothes and shoes and I was wrong.

It was in January of 2018 and she was doing some cleaning in our master bedroom and pulled my box of women’s clothes out and pushed it back where she found it. She wasn’t happy with me and knew something wasn’t right when I got home. She had me come up and pull it out and I told her they were mine. It got even worse and my ex-wife told me I needed to pack my things up and leave within 3 days.

It was horrible and I knew I had let her down. I wasn’t honest to her about it and knew I should of never did this to her. I was lucky, my oldest brother let me stay at his place until I found a house to buy. He trusted me very well, helped out very well knowing I don’t take advantage of him freeloading.

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He looked at me and said I had problems and I told him that was certainly true. I was 39 at the time and told him to have my second older brother come over and he did. Both knew I had a secret in the closet and I came out as a crossdresser. They knew I was in a lot of pain holding this 24-year secret in. My ex-wife and I divorced. She didn’t want me in her life anymore finding what I did was disgusting to her. After the divorce was final, I.had to put in a new chapter in my life. I wanted a new life as Kimber fulltime and I did just that.

First thing that happened was my male wardrobe was completely purged of completely. I found men’s clothing was boring to wear and this purge was the start of my journey as Kimber. Kimber’s wardrobe stayed and knew I was never going back. The best part was showing my brothers their new sister in their life.  I was finally completely happy!  I was relieved my brothers loved and accepted me right away. They call me Kimber now using the pronouns she, her, and herself.

To this day, my journey is going well. Family members and friends see me much happier. I still have my son and daughter in my life as well. My son accepted it right away I was finally happy as Kimber fulltime. As far as my daughter was concerned, it took her time to accept my cross dressing. She learned I was hurting for a long time and now have a much happier life now thanks from help from my son. He was 18 at the time and she was 15. I taught her I am still a normal dad much happier as Kimber fulltime. She listened and her first words were, “I love you dad!” When she finally accepted me and I was speechless with tears of joy coming out of my eyes after she said she loved me. We did hug after that and things with her have been great ever since.

Finally, some questions you might need to ask yourself below:

How did things go when you decided to come out of the closet with your thrill of cross dressing to your entire immediate family?

How did your wife react the first time you either got caught cross dressing by her or when you had “The Talk” with her and came out to her as a cross dresser?

How long were you in the cross dressing closet before you decided to come out of that cross dressing closet to your wife?

Think about it, living a life unhappy and miserable is not the way to go. Also don’t take your life for granted. You will have road blocks in your life which you need to overcome. There might also might be someone trying to hold you back as well!

Thank you for reading my article and my questions to you as well!

Sincerely, Kimber



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    Kimber Callen

    A fulltime crossdresser of 2 years late in my life.Did cost me my marriage to my ex wife after she found my stash of women's clothes and shoes 3 years ago.Was not too happy about it at all.A new chapter in my life after the divorce was final,discovered I loved the women's clothes more and now happy as Kimber fulltime.

    Latest posts by Kimber Callen (see all)

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    Julie Clarke
    Julie Clarke
    2 years ago

    My ex partner found my knickers and thought I was having an affair with another woman, I confessed to my crossdressing, she did not believe me so I showed my vast variety of clothing and breast forms, after that she incoraged me to dress when alone.together We also went shopping for dresses for me dressed in drab for some beautiful dresses, but when home would get dressed up and relax together and watch tv. With a new partner now I told her straight away and showed her my now wardrobe, she was ok with this but does not want to… Read more »

    Amy Myers
    Noble Member
    2 years ago

    Kimber, I am so glad to hear you have found your true self, and am able to live that life now. I feel that you are so lucky to have brothers who accepted you, for what you are. I suspect that they knew for a long time, so it wasn’t so much of a shock for them. Now to try to answer your questions. Though the circle of those “in the know" keep widening, none of my immediate family, other than my wife know about Amy. I very much want to tell my adult children, though my wife doesn’t want… Read more »

    Ashley Konners
    Trusted Member
    2 years ago

    I’m so glad that your living the way that makes you happiest hun! To answer your questions… I haven’t told my whole family , just my wife, older sister, sister in law and my 20 year old niece and my female boss at work. They all accepted it whole heartedly and have supported me and given me lots of encouragement as I’m venturing out more frequently in public. My wife always knew of my love for pantyhose since we started dating but I didn’t tell her about my secret until 6 years ago now. I felt I needed to tell… Read more »

    Bobbi Watt
    Active Member
    2 years ago

    Kimber you have two kind brothers and I wish every one could be kind. I was married for 33 years and had never been caught and for some reason I told my wife . It went well and since then I have told my two sons . They were both under standing my youngest said what ever makes you happy its cool. I am coming up on 39 years of marriage and yes we have our ups and downs but it is going good . I have told my sister and her husband and they have been grate and I… Read more »

    Trusted Member
    2 years ago

    Inspiring post Kimber, the combo of situation and decisions led you to a positive outcome. Mant of us fear our lives would be over if our wives left us, our kids temporarily disown us, our families forget us, and our friends despise us. Could we really end up 4 for 4 in losses. Would 2 for 4 in losses be all that bad. Or would having everything but ourselves be any better. Either we have all else and live a life that’s not us, or risk some of it and have a life that is us. Looking back, with your… Read more »

    Hope Roberts
    Active Member
    2 years ago

    Thanks for being so brave KImber and coming out to your family. Only my wife knows I am a crossdresser.


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