Were you nervous the first time you crossdressed?
I’ll never forget my first time going out crossdressed, even though it’s almost eight years ago now. I had been dressing at home for many, many years and underdressing as often as I could, but I had never been out ‘en-femme’ before. A few weeks earlier I had joined a local crossdressing group and had finally plucked up the courage to attend a Tri-Ess meeting.
In my infinite wisdom I thought it would be a good idea to go out crossdressed for the first time. I was conservative in my femininity – I wore a blue blouse over some slightly feminine jeans with a bra for my breastforms and just a dash of makeup. With trepidation I exited my apartment, eager to quickly make the trip down two flights of stairs to my car without being seen. Then as I step foot into the parking lot I’m confronted by
Cops, everywhere – and they’re after crossdressers!
And I’m dressed. They’ll notice my boobs and my feminine blouse. Oh God! Now I’ve gone and done it I knew I shouldn’t have dared to venture out crossdressed. I almost died of embarrassment right there. I knew I was going to get into trouble, or at least a stern rebuke.
As it turns out, the police officer wasn’t outside my apartment waiting for crossdressers and he didn’t pay me much mind. I got into my car without any problems, and was off to my first Tri-Ess meeting.
Over exaggerated fear of what will likely never happen. That’s what I experienced the first time I went out crossdressed, and I have a hunch that I’m not alone. Our worst fears rarely come to pass yet we spend so long dwelling on them. It’s only when we’re out in the moment that the fear can be replaced with the joy of expressing one’s feminine self.
Going Out Crossdressed For the First Time
A few weeks ago I was blessed to take my good friend Vicki on her first crossdressing expedition into the cisgender world. She had visited the Emerald City (a local transgender club in Seattle) before, but leaving the safety of an understanding transgender group was new for her. We started out the afternoon with lunch at Chinese restaurant that we had all to ourselves, and despite some interesting smiles from our hosts it was a great way to ease into crossdressing in public.
Vicki truly showed mastery of her nerves when she suggested a quick trip to the mall together. Dining in a deserted restaurant is one thing, walking through a crowded mall is quite another. It was wonderful to see the sense of joy and accomplishment in her face as she took a proud step forward into the world as her feminine persona.
What was you first time going out crossdressed like? Was it nerve wracking, exciting, joyous, liberating or something else entirely? I’d love to hear, comment and let me know.
After fifty years as a closet crossdresser, two of my friends manged to coerce me into going out in public. Went to the beach and walked in the sand. Each time someone came toward us I looked away in case they spoke to me. I was frightened yet excited, when we returned home I was so pleased with myself.
Next time was a month later and the same friend took me to a casual restaurant. I gave her the money as I did not want to speak.
We sat down and had our meal quietly, then I held both her hands and
cried and cried. That was when I realised that living full time was possible. Two years later I go everywhere, frequently I go to
Karaoke bars and sing, yes I have a male voice, but nobody has yet
treated me any differently from the other singers.
I am fortunate to have a high level of confidence, I choose carefully what I wear when going out to ensure that I present as a convincing female of my age. Being part of a support group helps immensely.
Thank you for reading my story.
Sarah
Wonderful Sarah – that’s quite a testament to your courage. I’m so glad you found happiness in being who you are!
You are an inspiration to me. I am just finding myself, but it scares me to death. When I done my female self, I feel so inadequate and awkward. None of the womens clothing fits me right. I still have yet to go out in public. I'm too althelticaly built to pass it off properly. Reading your post has reminded me that careful wardrobe planning is ever more essential for us than a biological woman, Any tips or advice is appreciated. I posted below under "scared"
[...] shared with you my first time crossdressing at a Tri-Ess meeting. . This was followed by my first time out in public outside the meeting room, [...]
Hello,
I can only dream of going dressed as a woman because i am trapped because I am handicaped and I have no way to get to any place, or to go to. I would love to get some help but whare is my question?
If I could get the help that I need I would go to it?
I would love to go out dreess as a woman the very first time but cannot. what are we to do?
Thank you
Terri
im a crossdresser in bangladesh. i like women dress so much. i like to wear panty bra and other women dress. i want to meet other crossdresser
im done
I M A CROSSDRESSER IN BANGLADESH , JON PLEASE CONTACT ME AT MY E-MAIL PLEASE, I FEEL ALONE,HELPLESS. I WILL BE GRATFUL IF U MEET ME. WAITING FOR YOUR REPLY.
mitahoq@yahoo.com
VENESSA PLEASE HELP ME TO FIND BANGLADESHI CROSSDRESSER
I struggle daily with my need to crossdress. I have always felt the feminie urge. Luckily I have a bi wife who is fine with it (took 2 years for me to tell her) and now that she's helping me with it I'm terrified. I in no way resemble a woman. I am just shy of 6', well muscled, but not overly so. I could maybe pull it off in a dark room but my chest and face…oh god, its so embarrasing. I have never told her how insecure I feel but seeing some of everyone else's stories gives me a little faith. I have tried dressing in sexy lingerie for her, but it never seems to do it for her. I feel so hopeless in this. I fell as if I should go back to just supressing the feelings. Any advice, be it fashoin, psychological, or otherwise would be greatly appreciated. I don't know what else to do….
I have a slightly more unique experience, I'm colby. I am a genderfluid, so when I dress contrary to my masculine body it's not cross dressing, it's simply expressing that which I am, a genderfluid, neither male nor female yet both. Anyhow. When I go out dressed, which used to be rather normal…every other day or so, I had no problem with it, except now which it's been a while since I did, mostly I've been forced to live with less accepting people. I go out and have to steel myself to be myself, and when i finally do if a car comes driving by I am afraid it's someone I know, or someone my family knows, so on and so forth. Writing this maybe it's not so different. My reasoning may be different but the effects are the same in general.
ive gone out twice crossdressed onece for hollwen and once to adrive in move hollewen was no big deal the drive inmove was a lot more different i was nerve racking once i got too the city i was ok cause nobody new me i had a great time with my wife
My first time was 3 years ago. My wife took me to an inner city street full of pubs. Getting out of the car the first time terrifying but exciting at the same time. I was wearing a black net sleeved top, breast forms, jeans, boots, make up and a wig.
Anyway, we walked past 4 pubs with groups of blokes standing around. I had to walk right through the middle of them!
Scared to death I was, just waiting to get caught. Incredibly, I didn't get one double take!
The feeling I got from passing was the best thing out! : )