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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Hi I’m Paula, and I’ve been cross dressing most of my life. I never went out until I was 56 and I waited until Halloween, and I went out. I drove to a casino which I had planned on going inside to gamble. I arrived in the parking lot and I wanted to go inside so badly I could taste it but I just couldn’t. I ended up driving back home. Disappointed. Once again I’m going to try it again this Halloween, to see what happens. Thanks and still trying Paula.
Good luck hon! Halloween is just around the corner. Remember, everyone will be wearing crazy costumes 🙂
I go out everyday in a subtle way. I of course wear my bra and panties, but as outer wear, I wear women’s blue jeans, and a button down blouse, or a tee shirt. Foot wear in the summer can be sandals which do expose my painted toes. In the evening, if I go out for some adult entertainment, I might wear a cami, with a skirt.  Â
I have been dressing since I was twelve. But after college, I had the urge to do more than be by myself. So I checked into a hotel outside Pittsburgh, PA. I was so nervous! But in downtown I made an illegal right turn and got pulled over by a policeman. I always assumed that there were laws against crossdressing but there aren’t! He gave me a warning but then let me go. I was relieved! My soul was satisfied when as I was driving back into the hotel parking lot, a man gave me the “look."
Wow, the first time out, I do remember it well. I was 14 and how thrilling it was. Like most of us I started playing around with girls clothes and shoes at 11. I would try on my mom’s high heels and walk around the house. That sound that they make is so exciting. At 12 I was invited to a costume party by my cousin, She asked me to come as a girl. I told my mom and she went out to get me what I needed. It was a simple outfit, a blue party dress, white stockings and… Read more »
The first time I ventured out as Pippa was while on holiday just outside the coastal town of Ilfracombe. My wife is well aware that I dress and in fact it is when we’re on holiday that we are most relaxed about it, as there is no fear of being disturbed by any family members. I had already mentioned to her that I wanted to try and capture a nice sunset and as a keen photographer it raised no suspicions of wanting to be on my own for an hour or so. I showered and put on my undies and… Read more »
First Time out. I resolved a long time ago that I was a crossdresser. I had tried, and failed many times to quit. I had accumulated and purged complete wardrobes. I had prayed many many rimes that God take this need away, and each time He answered that His Grace was sufficient. So I finally accepted that I am, and always will be, a crossdresser, and that God loves me just as I am. I have forgiven myself, and now even love myself. So I shopped. As a guy, I would shop the smaller boutiques and clothing stores. Always as… Read more »
I am new to crossdressing need help
my first time out was on halloween. I drove an hour to our state capitol city. I parked in a downtown parking ramp with a suit case filled with my favorite outfit, makeup, wig and heels.I wore a grey sweater with flare leg jeans and matte black 5 inch heels. A blonde wig with a black beanie hat, and a black purse. my makeup turned out great and I knew I was very passable.I left my vehicle, walked down the stairs and onto the sidewalk. My heart was pounding a million miles an hour.I walked around the capitol buiding where… Read more »
My first time was in my teens. I had moved and was living with my Father and step-mother. I was given the chores that normally she would do but because they used to get home late almost every day, I became the housewife and Mother to my three step-brothers. While doing the laundry, I discovered that she was my size and I started wearing her clothes (mostly her jeans and blouses). I already had my own undies but I did wear the sexy lace bras and panties I knew she never did. It was a girl at my school that… Read more »
for some time i have been getting dressed up in my shop after hours and i will jump in the car fast because im still scared, love riding around in the car with a skirt or dress, i have teenagers @ home so i’m not sure yet about going home but the time riding around in public helps, its very exciting ! one of these days i’ll run into a friend to go out with and make it easier>