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 Girls.
I have been out quite a few times I have also been in work as Jane and had a great time everyone was so good the girls were best and offered so much advice. I also started when I was 9 with my sisters clothes but now I am 60 I have my own stuff which is so much better. I love mini skirts and everything fem. My wife knows about Jane and even buys me stuff but she dont like me going out or seeing me dressed.
Jane xx
I started crossdressing when I was young, but I didn’t go out dressed up as a girl until I was 13 & I dressed as a girl for my boy scout Halloween party. My mom said she didn’t have time to get me a costume, then she said if I’d dress-up as a girl I could wear her old school uniform, my sister’s cheerleader uniform or my mom’s white tennis dress. Little did my mom know that I had started dressing up in her clothes earlier that year & now she said I should dress-up as a girl, this was… Read more »
Hi. I’m a tri-athlete and I love going out wearing micro race shorts to show off my legs and sports bra to show off my midriff. I have a slim but very trim body and shave my legs as other cyclists do so I think I look really good. I just came back from a solo ride and got whistled at and honked at so it was really exciting! I like this feeling of being feminine but at the same time I feel more sexually potent.
hi julia! sounds familiar except my sisters were the ones who liked me better dressed as a girl. i've continued it for over 52 years now cause it felt so right the first time why stop? it (i) just got better!
That would be a dream come true! I remember one miserable rainy day l was 12 and our neighbours mom phoned over if l could come over and play inside with her son Jeffery for the afternoon, we weren’t really friends more just neighbours, anyway my mother gave me the phone and told me who it was, she said that Jeffery was wondering if l could come over and play what she called dress up, not sure what to think l said ok, and told my mom l was going next door to play Well have fun she said ,… Read more »
Dear Julia sounds your very lucky When I was young I lived on Lake My parents renter cabins helping my ma. clean them I found a girls 2pice. I couldent wait to try it on later I did Then sliped a tee on over and down to beach Igrue up in the 60s I had long hair, there was a beach down the rd.when I got there I looked around to see if I new aynone. Then took off the Tee and played on the beach it was the best.
Hi all i had to comment on first tip out . I was introduced to dressing at a halloween party , like so many of us. well i was 12 yo old and did not realize then that I wanted to be more fem than male type. As the years passed I started dressing more and more but never realy thought I could ever pass. A couple of years ago I happened to meet a dom cd on line, we made a date to meet up in her part of the state. I was ordered to arrive dressed , and… Read more »
I need help with this , come on girls give me some help how to dress hot!!
hi kevin sophie here i think tht it is upto you if u think something is hot then where it i have okay maybe it is slightly strange to see someone walking down the streets of corby in the middle of winter wearing a mini skirt but if u think it makes u look hot then why not? it also helps if u have someone hu can help u suck as a friend or girlfriend ect. so just really be yourself and where wot u think makes u hot
No doubt that is the right attitude to have. Just do what makes you happy and what you are comfortable with.
I used to work at a bar and was always amazed at how little so many women would wear in the middle of winter just because they want to look like the hottest girl in the bar. They will totally risk Pneumonia for the sake of vanity.
So if a genetic female can do it, why not us? Personally, I bundle up when it’s cold. 😉
I'm wondering if dressing HOT by women is any different from a man dressing HOT. Opinions or ideas? As a qualification I have underdressed for 30 years.
At this time I went to meet a friend crossdresser. I had to travel on the toll roads and yes the blood was running . I became more at ease when I went through a few booths . It was a diffrent way of life. would I go out again. Yes but I would like people to see there are people out there that are not trying to do anything wrong we just want to blend in too. Help us if you wish. Or leave us alone let us live are lifes are way as long as it isent getting… Read more »
am older and look silly but love it
My first time, I was 35 married in a boring marriage. I had connected with a woman who was a professional call girl. We connected on a non-sexual level and dated for over a year. She had a closet full of female clothing for her clients to wear. I had no idea other men like to cross-dress too. One evening she told me she was going to take me out. I was nervous, no I was scared. I’m 6’6”, and at the time had a 32 “ waste and 54” chest, not exactly the female looking type. She bought me… Read more »
After fifty years as a closet crossdresser, two of my friends manged to coerce me into going out in public. Went to the beach and walked in the sand. Each time someone came toward us I looked away in case they spoke to me. I was frightened yet excited, when we returned home I was so pleased with myself. Next time was a month later and the same friend took me to a casual restaurant. I gave her the money as I did not want to speak. We sat down and had our meal quietly, then I held both her… Read more »
Wonderful Sarah – that’s quite a testament to your courage. I’m so glad you found happiness in being who you are!
You are an inspiration to me. I am just finding myself, but it scares me to death. When I done my female self, I feel so inadequate and awkward. None of the womens clothing fits me right. I still have yet to go out in public. I'm too althelticaly built to pass it off properly. Reading your post has reminded me that careful wardrobe planning is ever more essential for us than a biological woman, Any tips or advice is appreciated. I posted below under "scared"
Hello,
I can only dream of going dressed as a woman because i am trapped because I am handicaped and I have no way to get to any place, or to go to. I would love to get some help but whare is my question?
If I could get the help that I need I would go to it?
I would love to go out dreess as a woman the very first time but cannot. what are we to do?
Thank you
Terri
im a crossdresser in bangladesh. i like women dress so much. i like to wear panty bra and other women dress. i want to meet other crossdresser
I’m really wanting to be turned into a cute girl, I’m 24, 6′ 3″, 160, long legs, cute face, long hair. I have been having this fantasy for the past few months and i really want to act on it! I live in Atlanta, GA. so if you are close and can turn me into a girl, please reply! thanks J.
im done