Going Out Crossdressed For The First Time

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Were you nervous the first time you crossdressed?

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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About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

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  1. I’m not that much of a online reader to be honest but your
    sites really nice, keep it up! I’ll go ahead and bookmark your website to come back down the road. All the best

  2. Diane says:

    I have been cross dressing for nearly thirty some years and in the closet all of that time. My wife left to go see our daughter on the west coast of course as soon as she left I needed to get dressed and did so. Stayed dress all day in the house tho and it was really fun just to be dressed in those cloths. I had only about a month before gotten my first set of breast forms and I think that is what made it so special for me on that day. At any rate it was early spring and the days still were kind a short. So toward evening. I took off my the dress and underthings, took a bath and shave my legs. Got redressed in some new lingerie and had gotten along with those breasts forms. I sat down at my wife’ make up table and redid it ( I had been doing make up for a number of years and am pretty good at getting the look I wanted). I got done with that and went to my stash which was somewhat limited but got a black skirt and a cream colored blouse and sweater put it on feeling very much a lady, I put on my three inch black heels and just felt so good. I walked around the living room for a while thinking about what I was about to do made, a couple of trips to the door but didn’t open it. Just stood there wondering if I should venture out sort getting myself primed up I guess. Finally I got a light jacket and a black purse out of the closet and put it on open the garage door and got in the car, sat there for another couple of minutes deciding just what I wanted to do, started the engine and back out, drove down the driveway. Our home sits back off the main road so we do have a pretty long driveway. Got to the street and turned going toward town. Now I hadn’t eaten much all day and it seemed to have caught up with me. Just driving and feeling all those nice cloths on my body has sort of relax me and the feeling of hunger grew stronger I thought I could go someplace and get something to eat. The next thing I knew I had turned into the Mc Donald’s and got into the drive thru lane and ordered a hamberger baskets and a cola. When the girl said pull forward I sort a panic what would she think of me dressed like this and those thoughts ran ramped until I got near the window. I stop got my purse from the seat next to me and got out my billfold she said the price I turned toward her she smiled and I gave her the money she said something about needing some ones and disappeared, came back shortly handed me the food which I took and was about to go when she said, miss you have change. I was almost ready to leave she smiled again and gave me what I had coming, then said thank you and have a nice evening. I drove out of there and went to the park eat my burger and fries. When I finished I repair my lipstick in the car, got out and walked around the park it was early evening and mild, it felt so good just to feel so nice. I just about got to my car when a couple came along and stopped right next to drivers side door and when I got to the curb and stepped off between the cars the girl started to open her passenger side door then look up at me and held in close until I got in she then step out and smiled at me and sort a waved like she knew me. I smile back and started my car and back out of the parking place. When I put in drive I looked back at her she was looking at me smiled, I really don’t know if she had read me or just being friendly. I then went to the mall thinking that I would like to go inside and go to a movie Just to see if I could pull that off too, I sat there for about a half hour. Knowing what time the movie I wanted to see was going to end and the next one would start and wondering just how to go about buying the ticket, not do a lot of talking. Well the time came and I felt pretty confinedent got out pulled my jacket a bit tighter and walked into the mall entrance, from there to the ticket booth seemed to me at least a mile and a half away and the crowd was coming out past me. Listening to the click of my high heels, I just smile and kept my head up looking at all those folks. All the time wondering if I was pulling off the woman I felt I was, Anyway I got to the ticket counter and asked of one adult to, Mission Impossible, the girl didn’t look up just gave me my ticket and change and told me which theater it was playing in, smile and look right passed me to the next couple in line. I walked to the theater and found a seat and sat down, with the feeling of everyone who came in look right at me but after a few minutes the feeling of them looking gave way, to feeling so good about just being there. The movie started and it was very intense and about half way thru of course the drink I had gotten from Mc Donalds had to come out. I got up now what to do I really needed to pee and the lobby was empty so I guess dressed as I was I would use the ladies room so entered and did my business and washed my hands redid my lips again and went back the the movie. Setting down again as I did I notice the couple that had parked next to me at the park were two rows back of me. Wow now this will be interesting, if she remembers me. The movie ended kind of abruptly and sort of surprise me. I got to my feet and as I leaving my isle, when she came down the step and just smiled again when she went by her friend sort of waited for me and I justured for him to go ahead he smile and said nice to see you again this evening, so he surely had either talk to her about me during the movie or had seem me when he parked next to me as well. At any rate that was all that was to that. I walked out of the mall which seemed much shorter got into my car and went home. Much to my surprise everything had gone so great I dressed on Sunday again and every day during my wife’s absence the next two weeks. I did go out several times after that evening twice during the day which was way more of a challenge for me but seemed to be OK events too. Diane

  3. Blake says:

    to Diane,
    Just be you and go out dressed and do the things you would be doing if not looking female…i do..i only have female clothes.
    Just Do It ! ! ! you only have one life to live,so live it the way YOU want to,

  4. Barb says:

    Diane,

    I, and I am sure many other closet cases out here just loved and experienced empathy with your outing story.

    In my case I have visited a professional photographer who indeed was good to me, and I have done similar under the radar outings all dressed up.

    How exiting those outings were!

    But normally I am restricted to less than one hour ventures when I get that time alone.

    This means I am able to don the finery and strut around for a while and then it all comes off and goes back into storage.

    Today I worked on rebuilding the pool pump in my workshop wearing just a pair of shorts and very sexy satin four inch high heels.

    I enjoy every moment I can…..

    Barb.

  5. Karen says:

    Like many others, I’ll never forget my first time dressed out in the real world. I had been dressing for so many years and never having the oppertunity to go out en femme. Then one day after a snowstorm, the snow was shoveled from the sidewalks, but there was still icy patches in spots, and needing money from the bank, I decided to go out and just do it! Dressed that is, so I donned a pink running suit, some subtle make-up, page boy wig, white sneakers with pink accents, and a white goose down vest jacket, I headed off to the bank. After parking the car about a half block away (no parking lots, just street parking in this area)I sat there debating whether I should get out or just go back home. Well, I decided to go for it, and got out. Walking to the bank, passing people, I was a nervous wreck, but nobody paid me any attention so my confidence grew and I relaxed a bit. Walking to the front door of the bank, a man got ther just ahead of me and then…..Lo and behold!, he held the door for me and allowed me to enter first!!, I smiled at him and nodded my thanks and he returned the smile. I went to the ATM and he entered the bank proper. Now I was on cloud nine, nerves just about gone and replaced by elation! After leaving the bank and walking back to my car. though most of the sidewalk was clear of snow, there were patches that the sidewalk was narrow and icy, and this where my second moment of elation occured, a man coming the opposite direction, stepped into the snow and held out his hand to assist me through the narrow and icy path!…I was so excited, I thought I would orgasm right there! (I didn’t though). This little adventure was the start for me in going out in public en femme, though they are infrequent, they are still exciting and enjoyable.

  6. Blake says:

    to Karen,
    What a great feeling that is uh Karen ?!Do that everyday and it wont become difficult to out dressed……I do,EVERYWHERE i go,normal part of life for me.. Way to go Karen ! ! !

  7. stephanie says:

    Just went out for the first time today. Put on my makeup and hair. Got dressed. Sat around for hours imagining what could go wrong, then said “to heck with it!” and did it! SUCCESS! Why did I wait till I was 59?! God, I had fun!

  8. charlotte says:

    Also had been dressing for years and years, never felt confident enough to go out. 6 years ago I started looking at some pictures of myself and realized I could pull it off if I dressed conservative and low key. So I planned everything out. Worst part was I live in an apartment with a doorman and I had to get in and out past him! Luckily if you come and go with a key, they don’t ask questions. So I get all shaved and dressed, not too much makeup popped a xanax and out I went and it was surreal. I was watching to see if anybody looked at me funny but no, I was doing OK. Finally I got up the nerve to go into a store and buy something, and someone referred to me as “she” – then I figured for sure all was well. Since then I go out every weekend, and I’ve gotten more and more daring – different fashions, long hair, heavier makeup – but never a problem except once, when I was careless and got read a few times – so I head home quick!

  9. Gabriela Almeida says:

    I have read the post and the comments with pleasure and sympathy. In my case in take refuge in my car(rather late at night) but in my way to it I felt the exhilarate experience of the wind in my legs(I was wearing knee high dress) , that give my the courage to keep going, after drive for a while, fearing to by stopped by the police, I parked in a popular street and walk around the block…guess what?, I don’t know if I was figure out, or not… but nobody cared…an exhilarating feeling. I only regret non having enough practice with high heels. Not having an excuse to stay there I went to a convenience store and bought a bottle of water, very nervous about facing the cashier…again, no reaction.
    Conclusion: get out, be your self, you are going to be noticed by the ones that are attracted by you

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