What happened that inspired us to be Cross dressers? Why do we want to be feminine and pretty? Was it an early experience you had in life? Perhaps your role model was women? Or you grew up in a house with sisters? 

For me, I was an only boy who was in the house with my mother and three sisters and my dad was always away. I saw their pretty clothes and how they got fixed up and made to look pretty. Boys didn’t do this, I was taught that pretty early in life, if you liked girly things you were a sissy, and there nothing was worse than being a sissy. Only problem was, I did like girly things, I wanted to wear silky panties and pantyhose, and twirl around in a ruffled skirt, I wanted to wear makeup and I wanted to fix my hair in a feminine manner. I was ashamed that I had these feelings and thoughts as It was in the late 60’s and early 70’s before computers and the internet, so I thought I was the only one who had these feelings.

I tried hard to resist, however, I could not. I always swore I would quit dressing up after this one last time only to give in to my temptations and desires again and again. I wanted to be feminine and wear girl’s clothes. Since I was at such a young age, I didn’t fully understand why I wanted to do this.

My first encounter with feminine traits was with a young girl in my neighborhood who painted my fingernails bright red one day, I felt something in me that was hard to explain while she was painting and then blowing on them, as I was only 5yrs old. I knew boys were not supposed to have their fingernails polished, but it was exciting, and then I figured out I couldn’t just wash it off so I had to go home and show my mother and ask her to help me take it off. I also remember the laughter from my sisters as they teased me. That same year when my Mother asked what I wanted to be for Halloween, I said a girl! It was that way for a couple of years afterward as well. I have Halloween pictures of me dressed up as a girl wearing a dress and wig and smiling.

Herbal_breast_enlargement_naturedaycom (1)

Later on, my sister caught wearing her pantyhose and it was so humiliating, however, it didn’t stop me. It was just like that time I had been caught with nail polish on. Getting caught was somehow exciting to me. I wonder if I had been encouraged, would I have lived a different life? As a young boy, dressing up did not have a sexual component to it  because I had not yet hit puberty.

I know others have shared their dressing up with their wives, however, I just cannot do that with my wife. It would hurt her more than it would help me, so I am content stealing private moments when I have the opportunity. As a matter of fact, my joining Crossdresser Heaven is my way of meeting others and accepting and sharing this side of myself with others.

This is my introduction to the world as Vanity and telling others for the first time in my life that I want to be feminine and girly. As I am aging, more of my time and thoughts are consumed by crossdressing and feminine feelings that I couldn’t stop now if I wanted to.

I am so appreciative to Crossdresser Heaven for allowing me and others like me the forum to express who we feel like we are without negative judgment. I admire most of the others on here who have shared this part of their lives with their wives and significant others. They are the brave ones who I admire and I have learned so much from them. Some of them are so feminine and pretty!

Nature Day 3

I would never be able to pass as a woman and I am alright with that as the majority of cross dressers in the world have that same difficulty. The cross dressers who can totally pass as a girl/lady/woman is such a very small percentage of all cross dressers. I just love the feelings dressing up brings to me and being 100% passable is not important to me.

There is a feeling I get right before it is time to dress up and when the time finally comes, there is a great stress relief that comes over me that is hard to describe. I am always going to have these feelings and desires and today I do not wish them to go away. I love wearing girl’s clothes and it feels right. It has taken me a lifetime to get to this point in my life.

Most of us are at different places along our journey and that will always be the case. My hope is that others will read this and see that it is alright to be exactly where you are right now at this moment and that it is OK to want to crossdress and feel feminine.

So the question was, “Why do we want to be Feminine?” The answer could be because it feels right and brings us joy and pleasure. If you are young and struggling with your desires and feelings, please know that it is alright and there is nothing wrong with you. You are who you are and I encourage you to be comfortable with who you are. Be the girl you want to be and don’t let others tell you otherwise. It is ok to be girly and feminine.  I only wished I would have accepted it earlier in life and I would bet many of you feel the same way I do!

  • What do you believe the reaction of your wife would be if you decided to come out of your cross dressing closet and admit to her you are a cross dresser and have been for a very long time?
  • Would you like to share with me and our readers your very first time you cross dressed and how it made you feel?
  • Are you now happy we, as cross dressers, now have a site such as Crossdresser Heaven where we can finally share our thrill of cross dressing with others just like us with continued encouragement and support?

Please feel free to take the time to respond to either my article or to one or more of the questions I’ve posed to you above relating back to my writings in my article!

Thank you so very much,

Sincerely, Vanity




More Articles by Vanity Fair

    View all articles by Vanity Fair
    The following two tabs change content below.

    Vanity Fair

    No bio infio to share.

    Latest posts by Vanity Fair (see all)

    4.3 9 votes
    Article Rating
    Inline Feedbacks
    View all comments
    Polly' class='avatar avatar-64 photo' height='64' width='64' />
    3 years ago

    Yes, I agree with everyone else you are very beautiful and your story reminds me a lot of myself. I tell myself all the time I need to stop this, a couple days later I’m completely dressed again. So I guess I’m just lying to myself? I’m lucky to be open with my wife, she’s ok with it but not crazy about it. Take care.

    Anna Christ
    Anna Christ
    3 years ago

    Thanks for the post Vanity Fair. My first time crossdressing as around the age 18. Just a few items i used from my moms closet. I kept doing this untill i was found out. My mom was not to happy. Then i started buying a few items for my self & the feeling was great. A feeling i never felt before but i liked it. For me by dressing up i felt ok being with me. The dirty feeling went away. So for me it added to my sexy life. I moved out of my house & for probley 5… Read more »

    Yael Lyons
    Active Member
    3 years ago

    Thank you for your post Vanity Fair. I also agree with what you are saying. I have been dressing since I was old enough to be left at home alone. Not sure why I started but once I did I have never stopped. Neither of my wives accepted my crossdressing. At least my 2nd wife does not have an issue with it other than not wanting to see me dressed as a woman. I have even asked that if I could get to the point of being passable and she said no. She married me as a man and that… Read more »

    Daisy Marie
    Active Member
    3 years ago

    Thanks for the post, Vanity! Instantly I started remembering my early years when I tried to wear shoes and heels from my mother and some other relatives. As long as they were attractive to me (high heels being at the top of the list) and I wasn’t afraid of being caught, I tried to wear and walk with them. However, being the sole offspring up to my first 10 years of life, raised by a super restrictive and, sometimes, violent mother, led me to hide all my crossdressing desires. If I had been caught wearing girly attire and heels, probably… Read more »

    Suzanne Jeffries
    Active Member
    3 years ago

    Vanity Dear, First of all I can’t imagine you not being able to pass. You are absolutely beautiful. Just wanted to get that out of the way. I remember wanting to be a girl and trying on my mother’s things but I don’t remember the first time. These feelings persisted throughout my life and became over powering in my late 40’s. I started buying my own clothes and makeup. I looked terrible but it was a start. I came out to my wife a few years later and fortunately she has come to totally accept the feminine me. Even though… Read more »

    Alice Black
    Active Member
    3 years ago

    I enjoyed your article and could relate very much to your thoughts and feelings. One more thing, you look gorgeous in your picture.

    2 years ago

    You look absolutely fabulous Vanity Fair, sitting down with your legs crossed in a most feminine way. I am envious of you. I’ve been crossdressing for a long time and, although I don’t look anywhere near as good as you do I still am able to pass, when I’m out there in public. I have learned most of the many mannerisms of how a girl conducts herself ,so she looks like a lady. One of the hardest things to learn is how to sound like a girl when I speak. As long as I don’t get into a long conversation,… Read more »

    Jill Harris
    1 year ago

    Vanity, thanks for the great article. I agree with you “it’s alright to be comfortable with where you are at”.

    Would love your thoughts, please comment.x
    Subscribe To Our Newsletter

    Subscribe To Our Newsletter

    Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

    You have Successfully Subscribed!

    Log in with your credentials

    Forgot your details?