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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The first time I went out cross dresser I was 21. I had a cute little dress on with huge breast that I cut off a sex blow up doll & stuffed in a bra that was way to small. They were so big they almost would not stay in the dress I was in. The dress was my moms and so was the black wig that was long. To this day I can not believe I fit in her stuff. Gosh even the shoes were way to small she being a size 6. 1/2. I’m a size 8 1/2… Read more »
unsure of my age at the time,think i was 8 or 9,and i was being punished (and trained),at the time.Gran(curtsey),had decided that “horrid and elly little bois",would not be allowed back in Her house……,so if She(curtsey),required me to be Her grand-daughter or “sissymaid",then that’s what i had to be.took me until i was 27,before i realised that Her(curtsey) reasons were obvious……,thank you,for everything Gran(curtsey).love,hugs and sissygurl maid kisses,millie(c.d.maid) de c.
I had met a freind on line at the DC Transgenedered Ladies Site, she liked the picture of my legs! She was renting a time share on the beach where I live and invited me over to talk, drink champagne and to bring a few different outfits so we could play adult dress up. She also suggested that I arrive in my male persona but I thought that if I were to be true to myself I would arrive as the woman I intended to be that night. So. I dressed, packed a few different outfits and wigs and sent… Read more »
A Very Important thing that everyone must know, is that once you’ve been out a few times, it’s hard to put the genie back in the bottle. Press yourself to take that walk around the block…walk to the park…wherever. One good place…drive thrus…and place will do. Going through the drive thru will let you feel the exposure of being seem femme and interacting in a limited way at the same time. Move up to convenience stores…then department stores. Gay…or trans friendly bars are a given, and provide a safe environment…but they are too shielded. Go grocery shopping!! Getting yourself out… Read more »
The first time I went out dressed I went to a Halloween party dressed as a hooker . Most of the people at the party knew me but no body reconised me. I did my own makeup wig, false nails, False breast, woman’s cloths and looked great and won second prize $50. There is the short version of my first time out.
Many good stories and much good advice. Nearly all mirror my own experiences going out in public for the first time as a woman. My first time was also the first time I used my girl name in public. The whole experience was FABulous. My smile lit up, my heart skipped beats. Makeup – I am a minimalist in that regard – use enough to look good but avoid looking like a clown or a slut. Unless you are going to a slut party that look won’t work well and might get you the very worst kind of attention. Smile… Read more »
Wonderful advice, Rosaliy,
The makeup “less is more" is so true.
Act as if you belong and smile (because you’re enjoying it!).
The first time I crossdressed in public was about 18 years ago. I was living alone in small apartment. I had a day off from work, so I had shaved my body. Next, I spent some time applying my makeup, picked out a nice dress. The dress length was about three inches above the knees, so not too short. I put on pantyhose and a wig and looked at myself in the mirror. I was beautiful and was very nervous. I had no car, I walked everywhere I went. I put on a pair of flats, packed a small purse… Read more »
im scared of going out dress as a female in public i tried it at the last place i lived now i moved out west have a girlfreind and her and her family think im gay for dressing as a female
I started dressing around 9 or 10 after mom had me help with the laundry and I found out how nice and silky panties felt. Stayed closeted till about 30 when I had cover a night shift at work for a while. I was the last to leave around 10pm each night and I thought it would be a great chance to practice walking in my heels. Started with just the shoes but soon changed completely after work and would walk around in the building all dressed up. But when spring hit it was nice to step outside and soon… Read more »
I have been going out more feminine and shopping for women’s clothing when I can I wear panties all the time and wear women’s jeans and blouses with my boots.I shop for womens clothing at stores and no one cares about me.I am happy to be able to be the woman I want to be.It gets better and easeyer each time .Don’t hold out to long and enjoy the wonderful times.