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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Vanessa is a happily married 30 year old transgendered woman from Seattle. It's been a long road to acceptance for her, despite the fact that she has been crossdressing for more than 25 years. Sometimes, when she looks in the mirror she longs to see the girl that lives
within her. 
51 Comments
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.
I practiced for about 1 year before I first went out. And even that first time out was at about midnight so that no one could really see me.
After a few times out in dark of the night, I started to go to a transsexual / gay club. I would change in my car and spend the night as Carolyn. It was an accepting and supportive atmosphere and I needed that. However, I am really not into the gay scene.
Now I’m fulltime and will be having SRS in March 2010.
Go girls!
Congrats Carolyn – phew, that must have been a long year or trepidation for you dear.
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 Kimberly, the best advice is to take it slow, and to try and find a local crossdressing support group http://www.crossdresserheaven.com/about/crossdresser-support-groups/
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
Suzanne,
Going out for that first time when you are married is definitely scary. I have gone out a few times when my wife is out of town, always worried I would see someone I know. Or worse, they would see me! Last time, I convinced myself that I would just go out and have a great time. I got a massage from a wonderful therapist who turned out to be very supportive and sweet. (She had a boyfriend, though. Otherwise, she said she would have loved to go out with me!) Then I went out for a late dinner at a Chinese restaurant. (I have found that Chinese women are more comfortable than American women are with crossdressers.) Exhilarated after my positive experience, I went home and culminated what turned out to be a very romantic evening : ) ! I was so satisfied with the experience that I got up the next morning, dressed up again, took the train downtown and went shopping…en femme! Again, it was so wonderful! I just didn’t worry or allow myself to be too self-conscious. And no one gave me the evil eye. I even got to try on a wedding gown!
So, just be comfortable with how you look. You may even schedule a makeover for the morning of your day out at a local department store, like Macy’s. Make sure she knows ahead of time what you are doing so she can help you plan it all out.
Alex
Wonderful advice Alex!
Suzanne, good luck as you venture out. Make those butterflies fly in formation
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.
What a great analogy Emily. Anything we do that is different can draw comments from people. Most of them are probably just curious – we shouldn’t let other people’s interest stop us from doing what we know we should be doing. Let your crossdressing muse make artistry in your life
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!
Wonderful Sylvia, thanks for sharing! Even if you were read, it’s great that the shop assistant was still polite. I find that even when I’m read people are generally courteous – very rarely will someone make a scene.
For any ladies looking for a support group, you can find the web link to Renaissance and others here http://www.crossdresserheaven.com/about/crossdresser-support-groups/
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
Hi all, I too am from the UK, but am currently ‘closeted’. My wife is supportive and a few close friends know too, but I doubt to whether I could ever pass as a woman on the street, which makes me feel quite sad. I also have young children too and don’t want to cause them any distress either.
I am however trying to find the confidence to go out crossdressed for the first time (other than to a fancy dress party – how I love those), but I live in a small town in which I would no doubt bump into someone I know. Has anyone got any tips, or places where you can be eased into it gently?
Sylvia, your hotel sounds interesting, and I will look into that next.
Anyway, got to get back in my male attire before the family get home (sigh). Seasons greetings and much love to you all! Maddy x
Further to my entry above – I have been out shopping “en femme” several times since. I have again been to the shop I mentioned, and they are friendly.
I am trying to push the boundaries out, (ie using a restaurant for coffee, using the Ladies’ room, public transport etc) and taking every opportunity to interact with other people. Having a lot of fun, too! I hope my “english” isn’t confusing,
Hi Sylvia, I’m Ragina. Congratulations on your explorations. You are Breaking new ground for all of us. I only wish that there were more here in the states as bold as you. Perhaps then more of the “strait” world would not be as judgemental and condemning of the transgendered community, if they could see that we are just people, perhaps different in some ways, but people nonetheless. Good luck in what you are doing, and please, keep us all posted as to your progress. Love, Ragina
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.
Back in the mid 70’s was when i first started going out. i remember it well, i wore a short black skirt, red blouse, and suntan stockings. Had penny loafers on my feet . I threw my purse over my shoulder and out the door I went. still remember my heels clicking on the sidewalk. Now Im old, but went out last night, and guess what. I was wearing a skirt and blouse, suntan stockings, and my Mary Janes, and when I put my purse strap over my shoulder and went out the door….. the door, it was yesterday once more. Carol Ann
Thanks for the advice Vanessa, I think a car drive ‘en femme’ is very much on the cards! Your site offers an invaluable lifeline, despite being the other side of the Atlantic.
If you’d indulge me, I’ll let you know how I get on – I know it’s a comparatively small step to what many have gone through, but it probably has some relevance in this thread. I think 2010 could be very exciting!!!
Love to all, it’s been a genuine boost reading everyone’s experiences regarding their first time out. xxx
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
Congrats dear! So wonderful to hear
Congradulations and way to go, girl!
wonderful to hear, Emily. I hope to do the same soon myself. I’ll keep you posted as to what happens.Lots of love, Ragina
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
You never know how anyone will react. I am lucky that I have only lost one friends since I came out to my friends. Many that I thought were going to not take it well have been some of my best supporters. I have been very lucky. Many others I have talked to say that some of the most open minded people that they have told that they expected would support them turn them away and those they didn’t expect to supported them. You really just never know.
I am now 42, and working on telling my Mom, who doesn’t know yet. Only very few in my family know about me, or at least they don’t know the whole story. Actually today looks like a rare opportunity to have that talk with her while everyone else is out of the house. So I am planning to finally do this after breakfast. (Wish me luck!)
But from my own experience, I would say that if you feel that you rfemale side is more than just a phase, but rather is a part of who you are as a person, you should tell your mother as soon as possible. The sooner, the better. It will make things easier later, not that it is ever easy being transgendered, but it is better than hiding your true self. You only get one chance at this life and you have to live it as you and do what makes you happy. Evenif your mother doesn’t take it well at first, give her time. Find any good educational material on the subject that will help her undertsand and find a support group if you have one available in your area. There is also a wealth of information, support and resources right here on the ineternet.
I bought my Mom a copy of “True Selves” by Mildred Brown and Chloe Roundsley. It is by far the best book for information on crossdressing and transsexualism to help family, friends, coworkers, etc. to better understand things from our perspective. I am hoping to give that to her today.
The main reason I have not been completely out before now is because of my Dad, who is the next big obstacle. He is the reason I stayed in the closet as long as I did because when I mentioned as a kid that I wanted to have surgery to be a girl, he made me feel like the worst thing in the world. I don’t hold that against him, but it did hurt. Now I am not worried if he accepts it or not, but he has a bad heart and I don’t want to kill him by telling him. I was actually transitioning to female in my public life when his heart got in bad shape, so that is the only reason I put it off further. I do regret not just being myself from the get go and then everyone would just be used to me and accept it more. Those who may not have, well, who cares about them if they are not going to care enough to try to understand.
I think the younger you let people know, the better off you are later in life, even if it is hard for a while.
Good luck in what ever you decide!
The one thing I have going in my favor is that I know my mother already knows at least part of it, because when I woke up in the hospital after my car accident, They had taken my jeans off, so I was in the hospital in my shirt and panties. I did have a blamket over me, but I know that everyone knew. When they came to take me for a cat scan, I heard my Mom ask the nurse if she could give me two hospital gowns because she didn’t want me to be ambarrassed by amyone seeing my panties as my rear hung out of the one gown. So they put one on backwards before they put the other one on. lol
Anyway, although it has never been brought up, I know that she knows that I at least crossdress, but she doesn’t know (as far as I know, unless someone else has told her) that I plan to become full female.
Once again, my opportunity to talk to her was interrupted by others coming in before I could bring it up. I think tomorrow I am just going to take her for a drive and talk to her that way.
Hello Sophie, I’m Ragina. Yes I think that you should tell Mom about your crossdressing as soon as you feel comfortable to do so. I speak from experience that it is better to tell her than to have her find out in an uncontroled way, such as catching you en femme without any warning. It can really lead to a very unpleasant confrontation that you just do not want. My Mom found out that way and it got ugly real fast. Fortunatly, after a while, cooler heads did prevail and we had a good chat about it later, after things calmed down. It took a while, but the aceptance did come. I only wish that I had access to this wonderful thing called the internet back then and all the great sites that are there.Take your time and make sure that you have plenty of positive information to share with her. Be ready to answer a ton of questions and be geady for a bit of guilt” where did I go wrong” type of comments. She did nothing wrong, and neither did you. Above all let love and understanding prevail. I will pray for you that all may go well.
Sincerly, Ragina
thanks for the advice it was really helpful i have told her and she was shocked or suprised att first but things have been sorted out now and i think its all goin well now
Hi Sophie, Ragina here again. I’m glad to hear that the talk with your Mother went well. Remember to keep things on the up and up so as not to betray the trust that has started to build. This is a positive start. Always be truthful in answers to questions, and if you don’t have an answer, get on the web and get the information you need. Don’t try to BS your way around. Always be well informed and I feel that you will be fine. Best of all to you. Ragina.
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?
thanks for the advice it is really helpful and i wish u luck as well
I use to crossdress all the time starting in middleschool. My first time being seen was dressing at home (mostly mom’s clothes) and having a pizza delivered to the house. I opened door totally en-femme and paid the driver… my knees were shaking so bad as I waited for him to count out change…I just wanted to tell him keep it… but I was in school and money was in short supply. The driver never paid me or my attire any notice. I remember being so nervous I couldn’t even eat the pizza..hahaha..
After that I was hooked.. the rush of going out was such a exciting event.. first just driving around, then late night walks at night, runnin g into store for cigarettes(didn’t smoke) to going to movies or walking in mall on other side of town.. each new adventure was more and more exciting
I have been crossdressing for about 10 years now but have only been out in public 3 times , I did get a few comments on one occasion but I felt so empowered I didnt care , the reason I havent done it I think is because I will reach a point where I cant be anything but female and I am not sure what will happen then
I have to say I love the feeling of putting on a pair of panties and a bra, Ive beem a crossdress of 9 yrs.and I love slipping on a mini skirt and a blouse with nylons and heels. You might ask how I got started my sister when I was 13I went and told her that I want to try on cloths and she.Took me into her room and made me into her sister I dont think she realize that .I lovedbeing dresses has a girl. But over the next year she show me how to wear makeup do my hairwalk in heels.So i could go out in public.And I have done that and will always be in her debt .
I just saw this article today, which is coincidentally the first time I’ve ever really been out while crossdressed, so I thought I’d share my experience.
When I say “really been out” I mean out in a crowded area during the day. I have gone walking near my home at night while dressed, and even driven to a mall after hours and walked around the parking lot, but today I took a much bigger leap.
I went to the store in the morning and bought a bunch of make-up, then I came home and set to work applying it, which took a long time and many attempts where I just wiped it all off and started over. Once I was satisfied with my overall look, I walked to the front door and…stood there. For about 10 minutes. Finally, I pushed the nervousness aside and walked outside to my car. I kept putting my hand near my face to prevent other drivers from seeing it, or pulling my hair down to cover up.
Finally, I got to the mall and…sat in my car. I was so, SO nervous. Instead of getting out, I stared into the mirror and talked to myself: “You are feminine, you are pretty, you look great, no one will know.” After about five minutes of this, I slowly opened my door, got out, and began the walk to the mall. I felt like I was on a stage, despite the fact that none of the people I saw even spared me a second glance. It was going well, but it got even better once I got to the door of the mall. The gentleman I was walking behind pulled the door open, gestured to the entrance, looked me full in the face, and said with a smile and nod “Ma’am.” I smile shyly back at him, and my stomach dropped like I was riding a roller-coaster.
I went straight to the women’s restroom, where I passed two older women coming out who said “Excuse us, dear.” After touching up my make-up a bit (unnecessarily, but I needed something to do) I went back into the crowded mall and walked down to the end, then back to where I came in. As I was walking by the Electronics Boutique, I passed a family near the window. The little boy pointed at the display I was walking by and said to his mom “That one, the one the girl in the black shirt just passed.” I wanted to just run over and give him a hug!
After that, I became very self-conscious again out of the blue, so I just bee-lined it right to the door and walked to the car. I’ve been crossdressing for about 14 years, and I finally found myself with the courage and opportunity to head out in public. For my first experience out, I really couldn’t ask for anything more, and after such an encouraging adventure it will most definitely not be my last!
Now I realize I’ve written a LOT, and I apologize for that, but I was so excited about the day that I had to tell someone.
You don’t have to appologize for a long post. ( At least I hope not, or I have a lot of appologizing to do myself! lol)
Congradulations on your accomplishment today. The more you go out, the easier it gets. Once you start getting used to being yourself in public, you tend to stand out less because your confidence raises up as you enjoy yourself more and more and you get relaxed, then your don’t have that look on your face that screams “Oh my God do they all know?” Once you get to the point that you do not care what people think or if they are looking, or you just don’t notice them anymore, then you start becoming more passable because you’re no longer trying to notice if you’re getting noticed. It all comes with time.
It’s also a great thing if you have someone to go out with and just spend time out in the open with a friend, wife, girlfriend, family member….anyone that is supportive and accepting of you.
Keep it up and keep posting!
Ummmm, the first time was in Manhattan many years ago. I had been dressing and mking dresses with a friend at her apartment and mine. We would go to cross dressing groups but I would not dress to go. Then a couple invited us to their apartment for dinner and we accepted only after they accepted to come to my apartment. We had a lovely time and I cooked with my girlfriend for them and we talked and got to know each other as couples. The wife to the other couple wwas very open with me about my dressing adn complimentary adding to the night’s pleasure. It was so fun being dressed adn having guest over for the whole evening. When they left my girlfriend said to me “Now do you envy him leaving dressed to go home wouldn’t you like to dotht?”I quivered and said yes. A few weeks later we crossed town in my car with her driving with me dressed for dinner. I was terrified leaving the apartment to the car adn even in the car. We were stopped by a cop for making a wrong turn and we talked our way out of a ticket. As we continued our drive my girlfriend said to me “That cop couldn’t take his eyes off you, I’m jealous!’ I answerred, “He was checking me out to see if I was a guy in a dress adn I think he was confused.” “Oh he wasn’t confused, he liked what he saw, he saw how pretty you are.” I blushed crimson with her remark. When she asked me if I thought the cop was cute I refused to answer.
Leaving the car and walking several blocks to our host’s apartmetn was a continuing shaking at the nylon kness experience. I am 6′ 8″ in heels and everyone we passed on the New York City streets turned heads. No one said a thing. Just looked. I couldn’t wait to get inside. Once there it took me ages to calm down and enjoy dinner and dreings adn dance a bit. Then I had to tread going home. I was so excited i almost fainted. Once home I did what every red blooded girl does. I ripped off my bra and heels and fell to the coach and cried running my mascara all over my cheeks.
Years went by before I did it again. And I learned a great thing by waiting. It isn’t scarey now. Oh when I went out the first time I was again very self conscious. But then I noticed nobocy in Manhattan gave a damn. I hailed taxis, went to restaurants and events with so much more ease.
I loved it. It’s a lot of work even when I dress down and casual for an afternoon shopping tour. I get kids now an then giggling but I understand I’m an an unusual sight for them as they are looking so intently for thier own identity at that age. Most adults and all store keepers love my money adn me coming into their place.
Being with other girls is the secret to enjoying yourself. Hearing “yes dear, that’s looks lovely on you. or Oh no sweetie never on you” is so fun and girlie.
I can get up tight from time to time and think twice before I go through the work of looking nice, but I’m always thinking when I see a dress or skirt or demin slacks on a girl how i would look in it.
the first time…it was bad and good. just not good at makeup, but a couple gg asked me were a local beauty shop was at. my voice croked out a ‘no’.
getting out in daylight, all dressed up…..O how can one put it into words. if you long to dress and walk out the door. do it before you get too old. it is great.
the excitment, fear, you are scared to death. but nothing happens and you have been addicted to being your self. it’s great fun.
been some time back, had to lock up loni for a couple years…but this year she is back. and kicking up her heels….still need makeup help, but now i know of a couple places.
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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 a dream come true. I wore mom’s white tennis dress (it was very short & tight), plus a bra (well padded, stuffed), panties, pantyhose (I shaved my legs too) & a pair of white go-go boots with 4″ heels. Then a curly brown wig, make-up, nails, jewelry, perfume & then I was off to the Halloween party. That was my first time going out dressed as a girl & my beginning of going out crossdressed.
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 not to bring any thing male with me. I drove across the state dressed enfem, and so scared that i was trembling non stop. Once I arrived at her home she took me shopping at a local fetish store she went to. I was tarrified as she told me to get out and go with her, once in side I acted as her personal servant, i was to serve customers in their friendship cafe area , coffee ect. After about an hour I was starting to reaalize that few people realy cared how i looked. Once I was feeling a little less scared , I was instructed to go find some new out fitts and try them on , a kind of fashion show for any one there . I ended up with a stunning pvc chambermaid out fit , which I still love to wear lol. Well my New domm friend took me out in puclic dressed of course and i found that noo one except me seemed to realize that I was not dressed the propper way for my gender . Now i dress more pften and try to go out as penny , god it is such a wonderful feeling dressing in the fem styles that I love . Thanks Penny
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.
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.
am older and look silly but love it