Gather the courage to crossdress for the first time

You’ve been telling yourself for weeks that you’re going to do this. Debating with yourself, arguing with yourself, justifying why you didn’t go this weekend. Every time it ends with a promise that next time, next week, next month will be different. Yet somehow things don’t seem to change. You find that wearing your feminine finery at home doesn’t seem to satisfy a deeper longing inside you anymore. For a brief moment you wonder, “Am I cured?” Of course, you already know the answer to that question.

What stops you from crossdressing?

I don’t mean just crossdressing within the safe confines of your own home. I mean going out crossdressed for the first time. I mean gathering up all your self confidence and strutting out the door looking the best you ever have. Boldly going where very few other men have gone before.

Today I’m going to share a few reasons why you might be putting off such an important step, and how you can overcome your barriers to crossdressing.

You have nowhere to go: This is probably the number one reason why people don’t go out crossdressed – because you don’t think that you have anywhere to go, somewhere that is safe, where you won’t be recognized, and someplace that you can enjoy. Just before my transition I used to spend every weekend in a park just round the corner from my house. It was my sanctuary. I was able to be myself for a few hours, enjoy the sunshine with little fear of being outed. It was a safe place for me, and helped me build my confidence to go other places. You might find a local transgender meeting group (also a safe place), or a transgender friendly club or restaurant (your local transgender organization will know of a few) or if you’re fortunate enough – with a group of your friends who are accepting.

Join Our Community-cdh
What stops you from crossdressing?

What stops you from crossdressing?

You’re afraid: Fear comes in many forms. Fear that you’ll make a fool of yourself, fear that someone will recognize you, fear that you won’t pass and get into trouble. Since I have readers from all over the world it’s worth noting that you should take the time to understand local laws. Generally across the US, Europe and Australia it is not illegal to crossdress. The biggest antidote to fear is experience. Do it a few times and you’ll gain confidence. Spend a few hours en femme and you’ll build the habits and mannerisms that serve you well as you venture further out. Most importantly, start with a place that feels safe to you. Take baby steps.

You look horrific: Honestly sweetie, you don’t look that bad. This is a legitimate worry, since learning to be feminine takes time and practice. Even then many ladies aren’t blessed with the figure to pass there are still things you can do to improve your chances of passing in public. I’ve known many wonderful ladies who didn’t pass, but held their heads high and walked down the street like they belonged. Confidence is the difference between someone pointing and laughing, or someone coming over to chat with you because they find you generally intriguing.

So what stops you from crossdressing?

Hopefully with the few examples I’ve given you, you can see that it’s not the world that stops you from crossdressing, but yourself. Take a moment to think about what’s been holding you back, perhaps this weekend will be different…

Are there other reasons I missed? Please comment and let me know what has held you back, and how you overcame it. This will be a blessing to others just starting out!


P.S. Thank you to all the ladies who responded with their crossdressing success stories! I received them, I’ll reply individually soon. If you’d like to share, please submit your crossdressing success story.

En Femme Style

More Articles by Vanessa Law

View all articles by Vanessa LawTags:
5 1 vote
Article Rating
33 Comments
Inline Feedbacks
View all comments
Kevin
Kevin
11 years ago

This site is so helpful in so many ways . Keep up the the good work !!

princess sissy penny
princess sissy penny
11 years ago

thanks so much will do

vicky mynx
vicky mynx
11 years ago

Hi there Think this is a brilliant page, keep up the good work. i am a part time transvestite/cross-dresser & do go out dressed, but choose where to do it. Also try to get to a tranny night as often as possible in a city not too far away, but can’t always get as is expensive when have to factor in hotel cost. Think Another reason that can hold people back from coming out of the tranny closet if family, worrying what they will think. I must admit since I came out of the tranny closet a couple of years… Read more »

vicky mynx
vicky mynx
11 years ago

To previous reply, we men who cross-dress do so primarily because we like women clothes, & there is usually a hook. for me the hook was High Heel shoes, which I discovered at around age 11 or 12, when looking threw my mums catalogue. I don’t feel that women should have anything to worry about, if their man reveals to be a cross-dresser/transvestite (different words for the same thing)as this does not mean that he is gay. If anything, I think that its makes us more Heterosexual in a way cus another part of this world, is that we tranny’s… Read more »

Saundra P Ryan
Saundra P Ryan
11 years ago

I was very Pleased to read your Story Leah And for one i would Love to meet up with you for Coffee and chat as i admire any one who can take that step very Strong Minded of you Love x x x I would love to chat On line with you as well babe please if yopu can Love and maybe swap some Pics as well babe x x sean.riann@yahoo.co.uk

Kisses

Saundra P Ryan

simone88
simone88
11 years ago

This is amazing! this website is a dream come true for me. I have been shaving my legs, on and off, since I was old enough to have hair on my legs. I have had trouble admitting to myself that I’m different, and am only just recently free to explore my sexuality. I spent most of my life pretending to be a “macho man", all the while, scared as a little girl. Still scared, probably will be for a long time to come, but with sites like this, I don’t feel so alone. THANKYOU!

Mid
Mid
10 years ago

Such a lovely website! At over 70, proud grandfather, devoted to ex-wife, living by myself I have had such joy over the last few years to wear pretty things, feel satin against my body, and strut around feeling sexy in heels, earrings, and necklaces. Coming out totally? No. My friends, my family and my business partners would never accept that. But daily, every day now, a little makeup, lipstick, eye, everyone seems cool with that. Androgynous women’s silk long trousers, taffeta shirts, that button up the wrong side. These seem to be OK. Short ladies shorts and big belts in… Read more »

Sam victor rose
Sam victor rose
8 years ago

Hi it is very difficult to travel in train or air where identification has to be shown when u r having identification for ur mslr name. How to overcome this ? Can railways deny entry if u book in my male name ?

Lolita Hope
Lolita Hope
8 years ago

What scares me, is being raped and killed, en femme

Vanessa Law
Vanessa Law
8 years ago
Reply to  Lolita Hope

That’s not an unreasonable fear hon, as we’ve seen quite a bit of violence against our community in the past. I’d recommend finding a support group, and going out with friendly company.

Sarah' class='avatar avatar-64 photo' height='64' width='64' />
Sarah
8 years ago

Very helpful the reason I’m not going out as much as I would like is my 19 year old son move back and he’s home when I’m home

33
0
Would love your thoughts, please comment.x
()
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?