Going Out Crossdressed For The First Time

Nervous about going out crossdressed for the first time

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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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
  1. Sissy Minister Pope 2 days ago

    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 men and have found that a female size 8 1/2 fits well.
    Wow right.

    It was night time & I was doing my usual drive.

    There was at the time 2 stores because I was 21 & am now 38 & now there not there.

    I would go to 2 adult porn store & the rest area of a I-94.

    Then had to get gas & was like oh no I have to walk in to a gas station.
    Oh fear came across me so hard.

    What will this guy say?

    Will he laugh?

    Ah my heart beating so hard.

    But he was just like ahhh.

    Probley like gosh what big breast or something.

    I was ducking my head.

    Then got out of the store & to the car walk ing fast.

    Well that’s my first time.

  2. Profile photo of LadyCDJennifer
    LadyCDJennifer 3 days ago

    I’d be too scared of going out en femme. as I fear winding up like the late Gwen Araujo, a young trans-woman, who was raped and beaten to death at 17.

  3. sunita 4 days ago

    i am wearing every day saree and blouse indian dress and with light make-up but i dont store courage to out of home it may be i will be prepare to go outside as female thanks for yours initiation –sunita

  4. Profile photo of Toni Ginamaria
    Toni Ginamaria 1 week ago

    My first outings back in 1990 were to gay bars hair dressers and shops out of town. I would go out Dressed As a Boy DRAB first and later in the day in DRAG. My spidey sense was off the charts, but as nothing bad happen and what did I could handle, I became more relaxed. I got drinks bought for me doors opened and cigarettes lit propositioned by some, other times I would attract admirers that would hang around and look down at their feet and talk awkwardly till I would take the lead and flirt and reassure them. I would smile look them in their eyes play with my hair and brush against their arm or touch them on the thigh. Eventually I would go shopping ask for advice and try on in the dressing room before purchasing. I wore 4″ heels around the house and packed flat slippers in my purse. I practiced my make-up skills, went for applications at the hair stylist and department stores. The advice I got was to prep my skin shave clean tone moisturize. As for make-up less is more. My girlfriend would tell me that department stores work on commission drug stores are more affordable and you can return anything that doesn’t work. Note I have never before returned anything, ever. Go easy on the eye make-up, less slutty/ clownish rather more natural, better appearance to blend in with natural women. Watch how other women dress in the places you are going. No leather outfits short skirts and high heels at the grocery store. Try to copy to blend in and not to stand out. Sweater if you don’t yet shave your chest & arms tank top cardigan or blazer if you do, jeans and mid-heel boots or flat unisex shoe. My mom advice: go easy on the perfume to always stand up straight look people in the eye, ask for things in the form of a question smile often and say thank you. And finally don’t worry about what other people think unless they pay your bills. Get dressed put on your make-up and a touch of perfume grab your purse and go out stay safe and have fun.

  5. Janine 2 weeks ago

    I just got through reading about all of the first time out.
    I recently had my first time out and it’s true. Dress so that you can blend in walk like a lady dose. Try to keep from speaking as little as you can. Always look at whoever you are looking at in the eyes and most of all smile.
    I noticed that if you smile people just seem to look past you. Some smile back others don’t. Last night I went out dressed in a skirt and turtle neck long sleeve top with 3 inch heels. I went to a local Walmart and bought a new dress and a blouse. Afterwards I went to a sports bar and grill where I got a light snack after I had to use the ladies room which I did without any problem.
    Driving back to my motel I got caught in a traffic jam stop and go but by being patient I didn’t have any issues.
    Looking forward to going back out again today wearing my new dress

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