I will keep this short. JUST KIDDING I don’t write short so sit tight and enjoy yourself.

I saw this question because numerous people I follow either upvoted or responded and obviously caught my interest. There’s a stigma about cross-dressing, for example, when I came out to my girl about my bisexuality she already suspected it based on how nice I was to people specially to beautiful women or really good looking guys and how I wouldn’t oppose to watching gay porn “she was into” but was to test me. However, me being a cross-dresser nearly split us. It was something me myself didn’t accept at first but gradually became comfortable, I felt the need to connect to my feminine self and once the excitement, feel good stage ended I would curse at myself and call myself terrible names for doing so. In fact Tasmin Janus somewhat described me perfectly growing up a cross-dresser I did everything possible to look ugly in makeup and a dress. Imagine how unfeminine and ugly someone look with eyeshadow on, lipstick but beard and mustache. I would try my best not to cross-dress and when I didn’t I instead turned violent. It was for suppressing that part of me. I do believe that a reason you may be suppressing this is because of lack of style, not seeing a piece of clothing you are eager to wear. I grew up wearing my mother stuff since I had no sisters and I looked too old and may be a reason why I didn’t like cross-dressing so much, it wasn’t fulfilling, then my girlfriend stuff temporarily. She is a nice girl but dress too conservative. I like lingerie, mini skirts stuff like that. In the age of Amazon, Ebay, Jet, you can buy stuff discreetly and ship them either to work of a locker from UPS you can pick up from later. Go ahead, dress and if you don’t like it fine give you can always give to charity.

Considering the fact you are starting late and have questions and doubts, perhaps you should seek professional help. Whether you try cross-dressing first or later you need to find professional help. Tayren is in the field and can tell you that patient privacy is important. But if you still panicking over your privacy FINE find someone in the next town where nobody know you but that should be addressed. Even I who am sure I am a man, I love being a man and love both men and women and women clothes (by the way, being bisexual cross-dresser in a hetero relationship is super expensive geez) I still addressed this with my psychologist. Your happiness should be important to you and yes that first time is exciting even for me cross-dressing since age 6 was exciting finally looking at the woman I wanted to see on the mirror for the first time. You may not want to get confused and think “I am a transgender” and make changes you regret later when you find out you were in fact a bisexual cross-dresser.

In the end and this is what Venus told you, life is too short, live it to the fullest, be happy and don’t waste it asking questions. Every time someone dies young it always reminds me I am lucky to still be alive to live my life.

I always say this and you will notice if you read my responses. And Venus pretty much says the same thing that you will be old someday, I always say you are writing a book for a 90yo you will be someday, when that 90yo open that book, better be full of DID than IF and WONDER IF and regret not to. There will be many things that 90yo will look back and laugh about how foolish young you was like cross-dressing then finding out you didn’t like it, or probably thank you for finding out you like it then laugh at you for wearing blush as eye shadow, or probably thank you for realizing you were in the wrong body. The whole point is that the old person you will be some day will thank you for living and look back and say “I was a fool when I was young but I LIVED THANK YOU YOUNG ME”

The worst thing that could happen is not try then live a life sad and full of regrets. I unfairly lashed out to my family. Why? they didn’t know I was bisexual and was once hurt by the love of my life they didn’t know about a man I loved with my heart and he loved me too but hurt me and I had to lick my wound on my own and not share. What you prefer this feeling you have right now or be happy and free?