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.

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.

Exceptional Voice

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.

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Janet
Janet
9 years ago

I was one of the afraid for going out dressed. Fear of being ridiculed or at the time didn’t know what the local laws were. It was 1981 before crossdressers were not out in the public view very often. Eventually dressed and worked up the courage to go to a movie. I know not a lot of exposure. Maybe a minute crossing the lobby into the screening area and back to go out of the theater. I was noticed and no one made any negative remarks. I didn’t attempt to use the women’s restroom until I had been out in… Read more »

Johnny
Johnny
9 years ago

There are other reassons for being afraid to “go-out”. My personal reason, was being afraid of exposure, but for me it was part of my need for humiliation while being “forced to crossdress”. My wife was accepting, and would assist me while dressing as her “sissy”. It was sooo scary to be put out onto a rather dark and lonely residential street, and having to walk to catch up to the car that she would drive away in as soon as I would reach for the car door. I would be dressed up completely with makeup and a wig, but… Read more »

Judy West
Judy West
9 years ago

I am still trying to get enough courage to go out in public and keep putting it off for the reason I might be noticed or get stopped by a cop or I just don’t know if I look good enough like a woman. I want to start out by taking a ride to mail some letters late at night when not too many people are out. I only want someone to look at some of my pictures and tell me what they think of me crossdressed. Please let me know if someone can look at my pictures and I… Read more »

Janet Wyrock
Janet Wyrock
9 years ago
Reply to  Judy West

Also might check to see if there is a Tri-Ess chapter near you. This is a group for married heterosexual crossdressers. They also encourage wives to attend with their husbands. Most Tri-Ess chapter will also allow single crossdressers. http://www.tri-ess.org/SSS_chapdir.html I do not believe that is against the law to drive while appearing female. Obey the traffic laws, make a check that your vehicle is in operating shape, that is headlights, tail lights, turn signals, brake lights and license plate light are working. That will minimize the chance of getting pulled over by the police. Also do not drive after consuming… Read more »

Ronda' class='avatar avatar-64 photo' height='64' width='64' />
Ronda
9 years ago

Two months ago I started meeting a CD girlfriend at a bar in town that she been going to for about a year. I was very nervous until I had my first margarita and then a second, I finally calmed down. What a rush, after that it seemed that I was accepted by everyone in the bar.
I am now a member of a TG support group in Sacramento California and attend their monthly social. So get out there and enjoy being the women you want to be, I know, I have.

John/Saundra
John/Saundra
9 years ago

Well like everyone else. I was just a very part time. But scared C/Dresser. I never really got to the full stage at home. I even got Balloon’s for Brest’s now you could Imagine what I must have looked like really some freak. Any way I was on the site called Gaydar one night and I spotted someone, who was to become a very good Friend and yes Later a very good Lover as well. Any way Yes I was invited down to Waterford. Now I come from Tipperary. Yes in Ireland. So I packed i think it was 2… Read more »

sindee J' class='avatar avatar-64 photo' height='64' width='64' />
sindee J
9 years ago

motly my wife’s not willing to accpet me as sindee.so i do it and lie about it. Not to mention i really don’t ue make up well

Maliika
Maliika
9 years ago

A good site!
Thanks a lot!

Katie
Katie
9 years ago

Acceptance is definitely the primary fear along with the fact that I don’t have a girlish figure – though I do look better in a dress than the wife does (even if I say so myself). My parents were not supportive of my desire for interracial relationships, they would absolutely disown me for this transgression. Then, add the wife into it. I’m not sure how she’d react – then if anything happened between us, I can see the mud flying. So, as much as I’d like to admit to her at least, I can’t even bring just that one person… Read more »

Saundra/John
Saundra/John
9 years ago

Firstly as you know I had been out quite a few time but I was chatting to my G/Friend on the Internet and something Slipped out about cloths or something. Then out of the Blue. Carol said are a C/dresser or do you wear Female cloths. Well i was stuck to my chair and said I have to go now. But I Didn’t have to go any where but as I was crying at the fact that she knew. I was So shocked. Well Carol then Phoned me to ask the same question. said that yes I was a c/dresser… Read more »

Leah Lynn
Leah Lynn
9 years ago

I live in a small town where everyone knows you or at least knows who you are. My wife is not supportive, other than Halloween. A few years ago I dressed for a friend’s birthday party as a prank, that his wife suggested, so I have been in public, but not really as a woman. Last Halloween I was dressed as a normal woman, and a friend thought it was great; he wants to see me as Leah again. I’m planning to attend his birthday party as Leah, and I’ll stay dressed, instead of changing back to male personna.

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