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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236 Comments
  1. Mia West 1 year ago

    I found a link to this older post in my email I thought I would reply. Over the last year I have been going out and exploring mostly to friends houses, a few walks, and even to a couple corner stores. Last week I took a really big step and went out to a Lorde concert with some friends. I had an exhilarating time and it seemed magical. Walking around so many people all the fear had melted and I was not nervous I felt comfortable in my own skin as my self and that was so liberating. Every time I leave the house dressed as my self gets easier and reassures me that all of the fear was really all my own most people did not even know that I was afraid and they are to busy with their own lives to worry about me.

  2. Stella 1 year ago

    It has been a dream of mine since the mid eighties but as yet unfulfilled. It is tough living on a fixed income and having to buy to separate wardrobes. these days all my clothing comes from thrift stores except for under things. Three years ago I bought some lingerie from HerRoom.

    • PY Marshall 10 months ago

      Stella I would think about 75% of my wardrobe contents are from carboot sales and charity shops and ebay the rest is new . And my wigs are bought on line. PY.

  3. Joanna Knight 11 months ago

    Never have in the day time yet I’m not sure I can! I have been out many times at night to smoke a cigarette at night when I know no one can see me dressed as my feme side I have come to enjoy going out at night to smoke a cigarette ! Where I live we cant smoke inside so I have to go out my front door to do so ! I love being me in feme !
    I just bought me 2 new High-Waisted Bikini’s that will be in this week so I can see what I look like in a bikini! I also bought me SHANY ‘Timeless Beauty’ Makeup Kit, 44 pc ! I want to try out the makeup to see how I would look!

  4. PY Marshall 10 months ago

    Hi Vanessa and the other ladies. the first time I ventured out in daylight hours was just after making a pair of longline leg shapers with a bum enhancer combined. I had been watching a drag queen making a pair on Youtube and thought that would do me perfectly. They were just so successful. to be able to ware them I purchased a electric carveing knife £8 an elasticated body girdle which when on goes from the knee to over the tummy the same as the drag queen used . I think under a tenner. £10 My wife made me a holder for the pads on her sowing machine. Here we go. girdle just above the knee and then introduce the shaper ! hard going but after 5 mins mission accomplished I did wonder if 3 rounds with Mohamed ali may have been a better option. I popped on a pair of stretch denims and calf length boots with maybe a 2 inch heel in black , a top ,any top a nice floral scarf my red bertex jacket from ebay £4 .99 and because I have some heavy working hands a pair of black leather gloves .also second hand I find that both the gloves and also feminine glasses are a special asset, The glasses are my wife’s last pair .Both our eyes seem to be 1 step behind the other. So I have a pair of bi-foculs that are extremely feminine for free. Kind wishes to all PY. x

  5. Deni Hale 10 months ago

    I have been dressing and sneaking out under cover of darkness mostly. You know, getting dressed in your car and cruising ateas to meet guys. I recently joined Trans Ladies of Baltimore and after reading crossdresser heaven stuff, I decided I’m going to for it .

    A meet and greet at a local bar, full of young lesbians btw, me in my split front little black dress, I showed up and had a wonderful time. There is quite a bit more to tell, but heck it’s my bucket list begining to fill.

  6. Deborah Jennings 10 months ago

    I well and “truly” came out on the Saturday 29th September. The time was just after dark when I knew that people would still be out and about around where I live either on foot or driving so I would definitely be seen. Since I was coming out I had bought my outfit on line all in pink. So I was dressed and made up under a black Bob wig and with a slave chain padlocked around my neck, a tight pink long sleeve top stretched over and showing of the d d silicon breasts that were jutting out in front of me. A pink waist clincher belt covered the meeting of my top with the micro tight pink mini skirt that came to the top of my tucked tuck. I had 20 Denier black tights on and a pair of p v c black patent boots. I left my flat and then ten steps later I was on the public pavement and then I started walking towards the centre of town the first person I saw was across the road from me I just confidently walked on even though i had obviously been seen. Next I was at the road junction at the end of my street wanting to cross I couldn’t because of the cars going by up the street and past me coming down I was stranded on the pavement but I stood there indifferent. Then when the road was clear I crossed over, not wanting to push my luck and it being a bit of a walk back to my flat I crossed to the other side of the road and turned to go home but at the junction a car pulled to a stop I waited for it to pull away since I could see it was clear but the car just stayed there and I just stood there under the over head street lamp, I had no where to hide and it was obvious what I was and I stood there breasts jutting out exposed to all. Eventually the car pulled away and I went home oblivious to the passing of cars. Once in my flat I confronted the truth that I had become and was going to remain a cross dresser, as a male I had become ever more girly and in so doing so the male self of me was going to not exist it would be Deborah from now on. From a defeated but accepting male me.

  7. Catarina 9 months ago

    I said before that I didn’t go out en femme yet. That is true and untrue. Looking the way I do as a man (somewhat broad shouldered and bearded…), it is far from evident to transform in a totally convincing way. Maybe some day I’ll try that. But some 10 or 15 years ago, I found a way to satisfy my oh so strong longing to dress up and go step sipmly out in the world as a woman. I had bought a pantyhose of a very thick Den number, and not the most convenient colour for women (something brownish with a sort of knitted pattern). I slipped into a matching skirt, and a top – without any breast form. The rest was simple: male shoes and a mackintosh, long enough to hide the skirt, and I could pass for a man wearing knickerbockers. Was that cheating? Well, I guess so, but I did go out in a skirt! Did anyone guess that my legs were conspicuously without trousers? The lady in the local drugstore, who knows me quite well, didn’t show any other than the most normal reaction to my showing up. Did she wonder about the stockinged legs? I, for one, never noticed her doing anything of the sort, so I think my ruse worked. :))
    Next dream: going out in an outfit resembling an air hostess uniform: so elegant and classy! I’ll let you girls know when I did!
    Love, Catarina

  8. Jennifer Love 8 months ago

    I like some many of us was deep in the closet, only dressing when the coast was clear at home. I was lucky enough to have a couple of on line girl friends who I could chat with about my desire to go out en femme. They told me to start slow, maybe go out side my door, which I did when it was dark, then I took a drive at night, it was scary especially when I would come to a red light. I just knew the car next to me would ID me. Finally I found a gay bar about ten miles from me and check the place out in drab. I was able to speak with the guy who was in charge of the drag shows there about me attending en femme. He was very nice and I was even able to send him some pics of my self in my different dresses to see if they would be okay for me to come down in. He liked them. I finally pick a Halloween night to go. I spent hours getting ready and then made my exit when no one was at home and got into the car. I was so worried one of my neighbors would come out and see me. I got out of the driveway and started the drive. It was exhilarating thinking no one know I was a guy. I made it to the club and went in. I did look pretty good and did fool a few of the other guests, at least for a bit. I relaxed and had a great time. At the end I drove home, it was late so I didn’t worry as much about my driving back and when I got home the coast was clear and I made it into the house and to my room. Wow I was walking on clouds still dressed to the nines and being home, with all the great memories of my first time out. Now years later I still do it, and the anxiety is a lot less. I have done it many times and actually got pulled over three times by the cops, no ticket but that was really scary. They were nice and made it clear up front they knew I was a guy, did there business, like advising me I had a rear license plate light out and then let me go. I love going out now when ever I can get the stars aligned to do it, I am still in the closet but now have the training and courage to make it happen.

  9. Alysson Manson 1 week ago

    I am full time and the looks and hate that comes my way ,it takes some strength to pull this off ,old farmers and church haters are my biggest threats in public, with freaky people I am a hit , I live in a rural town of 10k in Missouri ,this has been eye opening to me ,now I know how it feels to be on the outside being laughed at ,the stares ,fingers pointing , I cant even carry my purse without hate coming back my way , nothing can get you ready but a strong skin and some will power ,I made u tube videos about this and my life as a cd , I wont change to make them happy ,they don’t pay my bills or sleep with me

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