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.
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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… Read more »
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… Read more »
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… Read more »
My first evening out came after a wonderful makeover at Janna's in Chicago.
She did a remarkable job on my makeup and set me up with a new wig. I had picked out clothes for the past months in preparation for this night. Two other girls were made up at the same time and off we went to Hunters in Chicago. The evening was uneventful, chatting and drinks, but being totally enfemme was such a rush. I was totally hooked.
Kerrie
I made my first foray into the world, while dressed this morning at 1 AM. I was sitting at home, dressed (as is my usual wont in the privacy of my own home) and was out of cigarettes. I thought, "This craving will pass – I will wait until morning, and go out dressed in male clothing to get more." Finally, at about 1 o'clock, I could stand it no longer. I was craving nicotine in the worst way, and really did not want to cahnge, just to make a short run to the local convenience store. So, girdling my… Read more »
I was not dressed "over the top" by any stretch. I was wearing black leggings, and a rust-colored jersey knit long sleeved dress, with a wide black stretchy belt. Conservative black 2" pumps on my feet, and a simple silver pendant completed the look. I had on very little makeup; just normal daytime concealer, mascara, eyebrow pencil, and lipstick in a subdued rust color that matched the dress. I carried a classic Coach shoulder bag. I thought the young lady at the counter had "clocked" me, but wasn't sure, because she said nothing while she was waiting on me. But… Read more »
Hello, I was born female and I saw this website advertised, I just want to say that I'm very supportive of men who cross-dress, a lot of people actually find it very attractive!! Don't ever be afraid to show who you are, if people mock you it's only because they're so ignorant, probrably from cultural views and follow what they've been brought up on, they haven't ever really made a decision based on their own heartfelt opinion. But yes, I would just like to add that I'm supportive of any men who crossdress as you should never, ever feel you… Read more »
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hi i'm from india
i want to be cross dresser
is any one in chennai
Thank you, this article has helped me to go out in public for my first time. What an outstanding experience. Every woman I met at the hotel I was staying at, with helped me or some how encouraged me to dress up as a woman. I am in heaven. Thank you, Michelle
I’ve cr0ss-dressed since I was 13, but didn’t go ‘out’ until over 50. Yes, I was scared, but it was exciting & fun !
Thanks for the article. Yours is the BEST c-d site in cyberspace
Thanks Polly! Great to hear you finally made it out 🙂
Feel free to tell others about Crossdresser Heaven if you feel it can provide some insight or encouragement to them.
*hugs*
Vanessa
I’ve cr0ss-dressed since I was 13, but didn’t go ‘out’ until over 50. Yes, I was scared, but it was exciting & fun !
Thanks for the article. Yours is the BEST c-d site in cyberspace
Thanks Polly! Great to hear you finally made it out 🙂
Feel free to tell others about Crossdresser Heaven if you feel it can provide some insight or encouragement to them.
*hugs*
Vanessa