Going Out Crossdressed For The First Time

Hi Vanessa,
your article brought back many memories. I was historical. I knew I had to step out dressed and I walked towards that door literally 100 times before actually stepped outside. I was so paranoid I had rented a motel room in a nearby town to make m first foray and I knew, just absolutely knew that ALL the people in he motel looked out of there Roms at that moment and where laughing hysterically.
That day was the first step. I am now legaly female and work as a cashier at a major retailer in a conservative southern state. I have the highest regard for our Tri-ess chapter. The president of that chapter was one of three transgender people to speak infront of the Fort Worth Council before the passage of its gender inclusive city ordinance.

Hi Kelli Anne,
Hehe - it's amazing how everyone has perfect tranny radar, and know just where to look isn't it 🙂

Congrats on your successful transition dear, it must seem like so many years and memories away from the first time you ventured out crossdressed.

Hugs,
Vanessa

I guess my first time was as a kid, but it was halloween. I said I wanted to go as a girl and my mom threw everything together on me and made it comical. I still had alot of fun, but it wasn't the outfit I would have picked out or the look I was after. It made for a fun night trick or treating but did not do so much for reaching into the real me.
As I got older, as most crossdressers do, I dressed up as myself for halloween, or at least as a female character. Many times I just went as my female self and usually passed really well for the most part, even alot of people I talked to every day did not realize it was me until I started speaking. Other times I would go as a female character. I tried being Morticia from the Adams Family (the old TV version), which was okay, but wasn't the best. A couple of years later, I went as the Angelica Houston version of Morticia, from the Adams Family movie and everyone thought I made the perfect Angelica version of Morticia.
I had gone out occasionally as a female in my late teens/early 20's with a few girlfriends that would like to have fun playing with my hair because I have always had my own long hair, plus being in bands in the 80's I never went out without eyeliner on at the least. So girls always loved taking turns fixing my hair for gigs or just for fun other times. Many times they would also want to put make up on me and, of course, I would let them. They often would tell me they thought I would make a good looking girl and would ask if they could fix me up sometime and do my hair and make-up more feminine instead of rock n' roll/glam rock, but to intentionally make me up to look female just so they could see what I would look like. You never heard me refuse! lol I actually loved it and was wanting that look before they even asked.
(The great thing about the 80's is that you could be crossdressing in plain sight and no one would know! lol unless you had a skirt, high heals or a bra on that was stuffed, no one thought much of it, you were just another cool rocker or a poser! lol)
Girls would do my hair up, put make-up on me and then let me riad their wardrobes or they would pick things out for me, (Sometimes they let me wear their clothes for band gigs, other times they would let me wear other clothes to see what I would look like as a girl.
Although I was not actually out to anyone back then that I actually identified as being a female and wanting to have a sex change, or that I even liked to cross dress, I was comfortable going out with friends after the girls made me up as one of them. I wasn't really considering it as crossdressing at that point as much as just being silly and having fun with my by best female friends. We all did have so much fun together.
So even though I was dressed female and going out, I wasn't really trying to pass myself off as female, but loved it when I was passing.
I think that is why when I started going out crossdressed later in life, intentionally trying to pass as female when it wasn't halloween, I realized pretty quicky that when you are comfortable with who you are and not worried about what others think and just live your life and having fun that you are more passable and more accepted by others than when you are nervous and scared and worried about being outed.
You can look your best and be outed faster when you are afraid of being found out than when you don't look as perfect, but you feel confident and just don't care if anyone knows.
I guess my first time that I went out intentionally trying to pass I was pretty nervous at first. Getting out of the car to go into a store was the longest walk I think I had ever taken. I did get a few looks once I got inside (6'1" tall woman, it's bound to happen. lol) but people are actually great in most places. I went shopping and then went to work that night for the first time as Racquel. I thought I would be more nervous about work than the general public, but a few people there already knew about me and the rest that found out that night were very supportive. The more places you go, the easier it gets, at least in my experience. The first time is the hardest, and I think you should make a day out of it and have someone close to you who supports you to be with you. I think it's much harder to get ready and then go out to only one or two places for just a short time and then rush back home where you know it's safe because you have let the fear, nervousness or everyone staring at you get to you.
The longer you stay out and around other people, especially crowds of people that you don't know, or may run into someone that you know, is actually better for you in the long run. You will get more relaxed as the day goes on and start acting more naturally and start learning to ignore the stares and the talking. Then it starts feeling easier.
I have had a few jobs that had absolutley no problem with me coming to work as Racquel. Even during times when I wasn't doing it full time.
I am looking forward to soon being able to live full time as Racquel again. It really sucks that we live in a world that just to survive, we have to not be ourselves. But my day is coming and when it does, I will never go back to living as a male again.

hi im a new crossdresser out of the closet . i live in a small town hear in cal and i try to go out but i git so far and i git nerves and go back home thar is no one hear for me to help me git me over the shaking nevis that i have is thar eny one out thar close to me to help me out i live in orland calafona . help plees

Hi, I am still in the closet but use all the opportunity I could get to crossdressed. My wife is going away for vacation in a few weeks and i am looking forward to crossdressed during that time. I am also looking this time to try to go out for the first time, just hope I will be able to do it. Have a Merry Chrismas to all.

Suzanne

hiya Suzanne,
Same here I'm still in the closet where going out is concerned, the only people I've come out to is my friends and family.

However as a male I do amateur photography and going out with professional grade equipment was something quite nerve wracking at first, people looking and commenting on the size of my camera, but now when I go out I don't even notice the comments anymore, just focus on great photographs (landscapes and macro).

Hopefully it will be the same if I decide to go out crossdressed as Emily, like the photographic side, over time it would become more second nature.

I attend a group based in Blackpool, UK, at an small hotel. Please visit the website, by putting renaissance blackpool in the search engine.

A couple of weeks ago I was able to get to Gynway (the Hotel), and dressed about 10.am. Petra went out shopping, but I was able to chat with a rather poorly Lynda. I then decided that I would brave the big wide world for the first time!

I walked down to the Prom' (ie sea front), (grey pleated M&S skirt, pink top with cardigan. I thought the front, being deserted, was not a place for a woman on her own, unless walking a dog, or accompanied.

So I headed up to Dicson Road. Near to this road, a family were getting into their car, and the small daughter waved to me, smiling. I waved back, and exchanged an understanding smile with mum. I am sure she did not "read" me. I walked Dicson Road, passing quite a few people, without anyone, that I could see, giving me a second glance.

I came across a shop selling second hand goods,including clothes. I found a skirt, and some boots, both unworn. There were two ladies serving (actually playing cardsmainly!) and I asked if I might try the skirt on. The older lady replied that there was nowhere to do this, but that if I returned it, they would credit me. I was probably "read" because of my voice (I am working on this!), but no comment was made.

Returned to Gynway, and tried the skirt on. At size 16 it seems slightly large, but it is so pretty, with two front splits, that I will probably keep it.

My shoes (size 6 black courts) seem to be getting larger, so it could just be that my efforts to lose weight are paying off.

This was originally written as a blog entry - I hope my English is not to confusing to our transatlantic sisters. Date was middle of October. I have since been out (shopping esp.) several times. My blog can be read on the renaissance website.

Love to all, and a Merry Chrismas and Happy New Year!

I attend a group based in Blackpool, UK, at an small hotel. Please visit the website, by putting renaissance blackpool in the search engine.

A couple of weeks ago I was able to get to Gynway (the Hotel), and dressed about 10.am. Petra went out shopping, but I was able to chat with a rather poorly Lynda. I then decided that I would brave the big wide world for the first time!

I walked down to the Prom’ (ie sea front), (grey pleated M&S skirt, pink top with cardigan. I thought the front, being deserted, was not a place for a woman on her own, unless walking a dog, or accompanied.

So I headed up to Dicson Road. Near to this road, a family were getting into their car, and the small daughter waved to me, smiling. I waved back, and exchanged an understanding smile with mum. I am sure she did not “read” me. I walked Dicson Road, passing quite a few people, without anyone, that I could see, giving me a second glance.

I came across a shop selling second hand goods,including clothes. I found a skirt, and some boots, both unworn. There were two ladies serving (actually playing cardsmainly!) and I asked if I might try the skirt on. The older lady replied that there was nowhere to do this, but that if I returned it, they would credit me. I was probably “read” because of my voice (I am working on this!), but no comment was made.

Returned to Gynway, and tried the skirt on. At size 16 it seems slightly large, but it is so pretty, with two front splits, that I will probably keep it.

My shoes (size 6 black courts) seem to be getting larger, so it could just be that my efforts to lose weight are paying off.

This was originally written as a blog entry – I hope my English is not to confusing to our transatlantic sisters. Date was middle of October. I have since been out (shopping esp.) several times. My blog can be read on the renaissance website.

Love to all, and a Merry Chrismas and Happy New Year!

Reply

Hey Maddy,

Support groups are always a great place to start. If there isn't one close by, perhaps going for a drive in your car would be a good way to be 'out' without the fear that you'll run into someone you know.

When I first went out back in 1975 I wore a black skirt, red blouse, and penny loafer flats. I wore plain suntan stockings, and a brown page. I swung my purse over my shoulder and out the door I went. I got to thinking that the other night I had on my gray skirt, suntan hose, purple sweater, and Black Mary janes. My hair style is longer now but I look near to what I did 35 years ago. when I swing my purse up over my shoulder its yesterday once more. carol

My first time out happened about 5 years ago.I found a cross dresser entertainer who did make overs and I brought my own cloths.She did a wonderful job with the makeup and I felt great until I stepped out of her appartment. I thought every eye was rivited on me and even in her car I felt nervous. We went to a cross dressing show and even got a free meal on the house as we were cross dressed. The night finally ended but I didnt want to take off my make up or cloths. I felt wonderful and now feel absolutely at ease when dressed up.If my wife was more understanding I would dress every day.

I've done it....
Went out as Emily today, enjoyed every minute of it. I was a little bit nervous at first but after a few minutes had passed, I'd got into the flow of things and just enjoyed the day.

have a great new year

Kind Regards

Emily

well i am fairly new to cross dressing and io want to tell people but i find i cant. i mean i am only 15 and i should tell my mum but i'm not sure about it . should i tell her becuase i am not sure wot she will think of me. she has always been proud of me but will me telling her this make her think differently of me need some help here any advice

i been out in public before and i found it liberating i found tht it gave my confidence and i enjoyed it yet i still havent told my family i dont no wot to do but i made a step in the right direction but any advice?