First Time Wearing A Skirt In Public

As an on again off again cross dresser from my early teens it was a big fantasy of mine to wear a skirt in public. But I let my fears prohibit me from doing it until I was about 30 yrs old. I was in Vancouver for a few days and i had some femme things with me so I decided that one night I would do it. I wore high heel patent black pumps with 3" spike heels, black fish net stockings, red panties, red corset boostier with garter straps, white blouse and blond wig. No make up or jewelery. I was super excited all day anticipating my up coming adventure. 

The shoes I bought that day and had an awesome time shopping for them and as soon as i purchased them I went straight back to my hotel room to practice walking in them. After a couple hours prancing around in them and admiring them on my feet I reasoned that i would be able to walk around in them that evening reasonable well. And then the fears crept in. What if I need run from trouble? I certainly was not going to be able to do that! Running in heels is a very advanced skill. But i beat back that fear by reasoning that if I needed to I would just have to get the pumps off and run in my stocking feet.

Finally it was time to go out and expose my femme mode to the world. I made my way over to the elevator and down to the car park. In the car park there was a car parking near mine. I swallowed hard and went straight to my car and got in it. Once inside my car I felt safe and not so exposed. I watched to see what the peoples reaction was from the other car but as they walked in front on me over to the elevator they showed no signs that they had just seen a cross dresser get into his car. 

I drove downtown and then drove around for quite a while looking for a place where I felt I could do this. I wanted people to see me but not too many. I wanted a place where i could get back to my car quickly if needed. I realized after a bit that I was letting my fears turn this into an impossible adventure! I beat back the fears and decided to just do it! I parked on a side street and decided I would walk around the whole block. I wanted to do more but I reasoned to myself that just once around the block first and I would see about more doing more after that.

I chose to walk around the block facing the on coming traffic. I felt this was safer knowing what was coming at me. there was no one on this side street which was a good thing because the side walk was in ill repair and was difficult to walk on with my heels. I almost twisted my ankle before i made it to the corner and was seriously thinking about abandoning this adventure. But when I got to the corner I could see that the sidewalk on that street was smooth and would cause me no problems. As I began to walk down the nice level side walk I focused on my walk trying to make it as fluid as possible. I could feel the skirt on my legs and the cold night air on my legs and i felt the shoes promoting a definite wiggle in my hips. I was in heaven. There was nobody walking on this street but plenty of cars were driving by. I was completely thrilled knowing that some of the people in the cars driving by were seeing me. I did not walk fast as I was just enjoying the moment too much. As I began to approach the end of the block I noticed that the up coming street seemed to have a somewhat steady stream of party goers walking up it headed to the bars. But that was good I was ready for it. I was feeling confidant and wanted to walk past people. A group of guys and girls walked up and stopped to wait for the light to change just before I got there. Most of them cast a glance at me as I walked around them and turned to continue my walk around the block. None of them said anything to me but I did hear one of the guys say "Is that a guy?".

I continued my walk pretending I heard nothing and noticed 2 girls were coming up the street towards me. They were attractive and dressed for the bars but they were engaged in a conversation with each other and much to my chagrin paid not attention to me what so ever. I even risked a glance backwards to them after we passed but they did not look back. The next street was the busiest street and most well lit. It had shops on it of which some where open and I was expecting their to be people but when I turned to walk down it I quickly saw it was empty. Despite that I wanted to be seen I was relieved that it was empty of people. But there was plenty of traffic and because of the better lighting I knew the cars driving by could see my face and know I was a guy In skirt and heels. I was just over half way down the street and totally enjoying my self induce buzz from this experience when I heard a horn blare. Instinctively I stopped and turned to see who had honked and why. It was a car full of guys and they had honked at me! Two guys on the passenger side were hanging out the window and one shouted "Dude your wearing a skirt!" They shouted more things but that was the only thing I remember them shouting. I didn't know what to do. I just stood there watching them drive down the street hoping they would not turn and come around the block. They didn't thank god!

When I was sure they were not turning to come back I turned  to continue my walk to the corner, knowing the safety of my car was would be closer with every step. But when I turned I saw I was no longer alone on the side walk. There was now a guy about the same age as me standing about 40 feet away. I have no idea where he appeared from. He looked like one of Vancouver's street drunks and as such looked creepy. But I had no choice except to walk past him to get to my car. He was openly ogling me only as a drunk would do. I had no idea how to handle this. I did not want to encourage him in any shape or form but I knew very well that to a drunk my attire alone was encouragement enough. The male side of me said there is nothing to fear from this guy but the female side of me which was in total control at the moment was scared and did not want any kind of confrontation with a drunk on the street! I walk past him doing my best to not wiggle my hips and to only watch him out of the corner of my eye. I got a little bit past him when I heard his drunken foot step begin to follow me. I sped up my walk a little so as to maintain the distance between us. Then as I started to near the corner I sped up a bit more hoping to gain some distance. When I got to the corner I walked out on the street and turned to walk up it to my car as I knew I needed to avoid the broke side walk. I got my keys ready so I would be able to unlock and get in the car as quickly as possible! I fumble with the key trying to get it in the lock and as soon as i did unlock it I opened the door fast to get in. As i turned to get in I saw he was standing right on the other side of the car looking right at me. I froze for a moment and he said " Hey baby wanna have some fun?" in a drunken slur. I looked at him and said " No Thanks" and got into my car and quickly locked the door and started the motor. Just before i pulled out from my parking stall I looked over at him and he shouted " A blow job please" I drove away!

I had hoped to do more that night but after being creeped out by that guy I just drove around for a bit and then went back to the hotel.
0hBrandie 0hBrandie
41-45, M
71 Responses Jan 4, 2012

Good going,Brandie. It took guts to pull it off but you made it work. You are an inspiration


Well just think of it you looked so good to him he wanted a BJ.
He paid you a complement. I don't know how long you have been dressing for but usually after a guy learns how to act like a women and is comfortable then he wants to see if he can perform as a women too. Samantha Lynn

I do accept it as a compliment but I was not ready for that as it was my first time out.

I have a friend on ep who is in somewhat of the same situation..have u ever gone out in daylight dressed as a woman? Do ur friends or family know? Do u think only the clothes and shoes are what u are attracted to or is it the feeling of being a woman that ur trying to achieve? I'm sry I asked too many questions n I'm also sry if I may come off as rude asking these questions..but I just wanna understand better 😃
U can totally ignore this too if ur uncomfortable ..i won't be offended 😊

Yes I do go out dressed in daylight as a woman now sometimes. But most of the time I go out as a male wearing fem clothing. My friends and family know. I think for me it is more about the clothes and shoes then it is about being a woman. I am quite happy being a male who has a strong fem side. Now having said that when I go out fully dressed I do love the feeling of being as much of a woman as I can be.

very true

i heard of small steps but that was a very large step good story

Well the small steps happened before that But ultimately the first time you go out cross dressed it is a huge step no matter what.

I enjoyed your story... Its full of the adventure feeling and is definitely an interesting read. I too want to go about it just for the thrill, but have had no courage to do so... I guess its not for everyone to do it!

I wanted to do it but still I thought about it many days before I took the plunge.

Wow that really gives me hope for myself, I have walked around in my yard a few times when it was dark out, and been dressed up in my black leather boots with heels and a nice lovely dress

Start with small steps!

love your story. Would love you to add me please..


It can be nerve wracking to go out when you haven`t done it but that mostly goes away. The fear of being seen enfemme seems to outway the reality of what actually happens if someone can tell. except for some rare instances of assault, the worst that generally happens is a rude comment. the world doesn`t stop turning and civilization doesn`t crash to a halt just because I`m out in public in a dress and heels. although it can feel that will happen lol. keep going out. you`ll be glad you did.

It does get much easier the more we do it!

Years ago I worked at K-mart and every now and then a crossdresser would come in fully dressed. Every employee knew she was a guy.
Being one who likes to crossdress and go shopping too, it was interesting to be on the other side and knowing the reactions first hand. I found there was nothing more than a few chuckles and comments between employee's and then everybody went back to work and paid no more attention. People may read you and for a few seconds they may think your strange, but then they go back to their own business.
My point is, if they don't know you and you aren't out to make friends with them, then what you do is your own business As you said...The world is not going to stop because you enjoy going shopping in a dress. When I'm out shopping I'm enjoying myself and I'm in my own little world and I don't care what other people may think or say.

So true and so well said. The reality is I dress for my own enjoyment too.

Wow, this story and all,of the responses .... All ..sound like me.. The same , excitement, same situations, same scared feeling when the drunks, the yellers , the close proximity of girls is upon you....
The fancy dress party sounds like the ticket!! Wish we had them here too... Second best , would be to go out with other friends in drag or better still women that don't hate me or give me grief or are discussed by my gross, disgusting sick form of pleasure.... Like my current girlfriend. Very sad for my situation... :(,

I think going out with other cd's would be a blast.

Agreed, just wish I could meet up and compare notes and fashion ideas...especially using make up... Argh that has been difficult for me...

It feels great to me, we would have fun going out dressed together?

For sure. I would love that!

I love dressing up and going for walks totally fem .

My wife made a date for me to go to a party dressed female on a Friday night in the summer with a later sunset so I would have to go there before dark. She selected my clothes, wig, nail polish, make up and lipstick. It was at an apartment and I had to park on the street, and walk past some houses before knocking on the apartment door. The wife of one of the men opened the door for me.

I do not know how many others saw me driving or walking.

That was wonderful of her to make you do that!

She thought so too

I loved your story. I can't begin to tell you how much I relate to it. I've done what you did many times. I've always noticed that girls will not give you a second look, but guys will always check you out and read you.
I also had an experience with a guy standing at my door and wanting to just sit next to me and **********, ya right? I can only imagine what would have happened if my door wasn't locked. My feminine side was feeling very vulnerable and I was scared to death.

That is why it is safer to go out with a friend but that is the chances we just have to take when there is nobody to go out with!

you sound like you where enjoying yourself pity you got put of by the drunk guy. I have always wanted to go for a walk at night all dressed up . Have you done it again

Yes I have. This experience happened quite a while back and the thrill of going out dressed up never faded so now I have done it many times.

Do you go all the way and have your make up done

Sometimes it got out with make up and a wig etc other times it is just plain ole a guy in womens cclothes

Good story. I bet your heart was pumping like

Yes it sure was!

You write so very well, perhaps you should think about taking it up for a living...≧✯◡✯≦✌

Thank you! That is very sweet of you to say. I would wish to have the time.

I need to do that

You can do it. Just be careful.

I hope you chose the west end for your stroll. When I'm done my diet, I plan for making an excuse to make an overnighter into the city doing exactly what you did!

It was around davies and grandville....I think that is kinds westend?
You will have a blast!

Wish I could go with you!

hellyeah. i wanna do that. i live in deep south though so i may need a gun in my skirt

And if someones asks if that is a gun or you are happy to see them you can answer both!

But you have to admit, it is always great to have something to shoot......
whatever the situation.

Good for you! Glad to see that you got to engage a fantasy and face some fears. That was quite a milestone.

Thank you

Very brave of you hun. xox


I am impressed with your courage. Also, you look cute as hell in that outfit!

Thank you very much Jennie!

I think we can all safely assume which category you fall into.

You should understand that I think could care less as to whether you do or do not look like a mentally ill idiot as you journey around the world. However you do a very good job of removing any doubt as to the fact that you act and speak like one.

Lets see...You are a man who wears womens clothes. You are attracted to men who dress like women. You question the sanity of such things. Fair enough...but I have no desire to help you in figuring out your sanity. If you want to think of yourself as a mentally ill idiot that is insane, that is your choice. It is a free world.

Just because men are not attracted to you does not prove you are not attracted to them. Your actions of chasing and pestering cd's here on ep is proof enough to as to your true desires. That is a FACT.

yes, we can all see that,,, some times in a crossdressers lifestyle we all have to go out in public and see if we're excepted... its very tempting

deep inside him , he loves wearing womans clothes.. he he he

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stay safe out there when your doing that, a lot of people are jerks, bet you looked amazing !

Thanks hon and yes I do try to be careful and safe.

Took courage - don't stop after that what gives you pleasure as long as it doesn't hurt anyone.

Thank you.

You're welcome - fyi - I much prefer Women's tights over men's - they are softer and therefore more comfortable - I also have tried on supressing my bits a little with tight women's underwear - not sure it works.

any suggestions? - as to how to maintain a little modesty while wearing my tights in public?

Usually I will wear a long enough top to cover my bits when I wear tights. That works for me. Something else I do is wear some firm control panties. The effect of this is still a bulge but nothing is defined and I don't mind that being seen. I have not tried wearing them with a complete tuck as I find that uncomfortable. Oh and yes for me it is womens tights only.

I think I will also stick to women's tights - I actually bought a load of them on sale...I honestly can't stop wearing them (four straight days) - I am not sure I want to wear anything else. Thanks for the tip...control panties (particularly black or red) work for me too.

My female friends say Just make sure you leave something to the imagination. We don't want to see the individual parts on display.

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Wow what an experience! You described so well the excitement and fun of going out dressed for the first time. I have done similar things to this many times over the years. But then to be followed by that creep. That must have been so scary. I can only imagine. I'm glad you got through it safely, and I hope it didn't totally ruin the wonderful experience of going out dressed.

It really did not ruin the experience for me. I really just wanted to break the ice and wear a skirt in public. I wanted it to be a place where I would not run into anyone I knew. I tried to anticipate all possible outcomes of my adventure and knew that there was risk involved no matter what. From that first time till now I can not remember all the times I have worn a skirt in public but I still remember that first time with such clarity. At the time I was more scared then I can describe but the wonderful feeling of being brave enough to do it made me feel proud of myself. It is still a wonderful feeling to wear a skirt or dress in public and I try to do it as much as i can manage.

Creepy! Lucky you had the car!

It was creepy.

You might need a genetic female to walk with you and show your faults. The aim is to remain unnoticed and accepted as a woman just passing by? If you want to exhibit yourself then the street is not the place to be.
If you are male shaped then this attracts the wrong attention, louts in cars are very quick to pick body shapes. They practice all the time to seek out prey. Something in your shape, height or demeanour showed them you weren't a true woman. But keep practicing, you'll get there hopefully.

You are so right.

Yeah, be careful. There are some really awful people out there. Get yourself some mace or something, if they can't see you they can't **** with you.

cool story hope you still go out dressed

I do still go out dressed!

It's tough doing this by yourself. Next time take a friend. When you get good at it then confidence will grow and you won't worry what might happen.

Yes being with someone sure does help in keeping unwanted advances at bay!

We all have our fantasies, let no one say they don't. You lived out yours, many people go through life not living, period. They just wear blinders and move so one notices them, kind of a dull existence if you ask me.

So very true!

Have you tried this since that time?

Yes I have. I do it fairly often now.

That Was A Great Storey And You Are Very Brave To Have Played Out Your Fantasie. I Hope That Drunk Doesn't Keep You From Doing It Again :-)

Honestly it did slow me down. If I had a friend to do it with I would have done it more often back then. Now I have more confidence and do it fairly often.

right On ... Love It..

i'd like to be your friend to do it with,,, just need a little encouragement

Too bad we do not live close to each other as I would happily do it with you!

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That is a great story. I remember the apprehension and excitement of being a girl for the first time in public. you should have sucked his drunk **** and swallowed his ***. I love ***.

And yet here you are reading it......that sure does show what you actually do desire despite your comments. But you are not the only guy out there that thinks if they speak loud and often against LBGT's that it will deflect people from figuring out your true colors.

And you are a twatwaffle.

i dont blame you

oh wow ! great story ! glad nothing bad happened ! :- )

Thank you very much hon!

Dear Brandie,you can be very proud off yourself,i have to admit,i dont have the courage ye to do what you did,but i aploud you very brave,i hope to get the nurve to do that too soon,big kiss

Good luck hon. You will love it so much!

My first time out dress up was at night fully dressed ,make up ,and high heels on, also very short skirt I decided to go to gay bar where I would not be judge as much I am 6.1 tall,slim ,but wearing a corset. Walking down the street from my hotel was the most exciting part.

Love it! what a wonderful experience for you!

Your comments scream fascist *******

wow quite an adventure,it takes courage even when its natural for u to wear a skirt to take a walk in a busy down town.good going sweety,but next time find the nearest lounge that caters to lgbt people and get use to it in a n excepting envioerment u might learn a few things to help your image and self confidence .good luck in your futureadventures b safe

that is quite the adventure,,, wish i had the guts

LGBT clubs are a wonderful place to start off for sure.

i'll have to look for some near me

i looked up in the computer and the nearest one to me, is 40 miles away

Thats a lot closer then the one nearest me hon! Take a drive and have fun!

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Hoped to do more? You did loads, girl! I wish I could be as brave as you. What an experience.

I guess it is brave but for me the desire over rode my fears!

I'm getting there... slowly. :)

oh here goes with the threats

Me thinks someone protests a little too much ;-)

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nice story, could have been trouble though

Well thank goodness it wasn't. I am more careful now but go out dressed much more too.

I am sorry for your bad experience! I had a good one that I wrote about here on EP, I went to a train show in a skirt! PLEASE read it an let me know what you think!

Shall do.

I went out a lot in Seattle at night. I went often to the gender support center, and to the friendly places on Broadway. I remember I was petrified when I finally worked up the nerve to go out in the day time. I chose a denim skirt, long sleeved blouse, and keds type sneakers. Wig, makeup everything. I went for pizza and then across the street to the small shopping mall. Needless to say, I did live through it!

Yes we all do live through it when we do it that first time even if we are so scared that we won\'t!

ahh the fun of being a x-dressed sissy, luv it

Yes indeed!

I once spent a couple of days cycling around Vancouver in mostly female mode, i.e. shorts and pantyhose, bra and boobs, and long wig. No heels, though, on my bicycle :). I don't recall getting any funny looks, although I wasn't really hanging around in any one place for much time. By the way, it's a great city for cycling in!

It sure is and actually Vancouver is pretty accepting of such things.

Exciting story, I had my first going out around a ***** mall near where I lived ! Congrats on your first walk !

Way to go! More of us need to to this.

I'm not passable, and don't try to be, but always try to be tastefully dressed. More guys should wear heels in public, even wore 4" black patent heels one time with a suit, got glares from men, but huge smiles from women who could tell I was wearing stockings under my trousers, very sexy night !

I never think of myself as passable but people tell me I am....Most of the time I prefer to be a guy wearing a skirt or whatever with no intention of passing. Yes i do wear heels with jeans and dress pants!

You should never be afraid to be yourself!

I agree! Thanks.

Thank you for sharing your experience. I hope you get to do it again and enjoy yourself.

I do it quite often now and love it! Thanks.

Sometimes a fantasy is just a fantasy ,you my Dear have crossed that line .Best of luck and be safe

I do my best to be safe. Thanks

Thank you for sharing Brandie that took a lot of courage, more courage than I have. I am so proud of you for doing it.

Thank you so much!

I live in a small town and there is on gay anything around

Same here hon

I would go to gay clubs dressed as a woman and some time go to a hotel and some time go home buy myself but it was fun

I go to them when I can now but there is none where i live.

lesbian bars are sometimes more fun to me, but they're harder to find

Very much harder to find but they sure are more fun!

Reminds me of the first time I went out. Only I didn't have to deal with slugs.

Yes well i did not expect to have to deal with that. And I like your term slug...very appropriate! But when I look back on it I see it was a valuable part of the learning curve.

i wish to do the same thing with out any clothes on me...

Well some people do that...but even I would like to do that I would not have the guts to do it. Good luck to you!

I the first time I wore a skirt to school was the original day of high school, and my GF was so scared of going to school for the first time in her life as she had been born.

We had matching out fits to wear that day she had a skirt that matched the kilt I wore to school, and we had matching tops as we got out of our car and walked into the office to get our class assignments, and no one noticed her but no one for got me as the boy who wore a skirt to school each first day of school from then on.

That is wonderful and was very brave too!

Great story


Hi brandie
It is a good wakeup call for all of us T Gurls to feel a dose of reality that women feel from time to time
Aren.t women so amazing that they bounce back from similar experiences to this and still want to date guys?

No kidding!!! I dress up and go out a lot more often now and it never ceases to amaze me all the things women have to put up with from

Oh I do not mind a nice grope now too haha

I have some fears about going out in panties and skirts

The fears will become less once you do it for the first time.

Great story.


A very liberating story. It's the shoes that prevent me I'm a size 12 they are hard to find!

They are hard to find for sure. Here we do have a few stores that sell them. Try online perhaps....

Payless does carry shoes in size 12 which you can try on. And DSW carries size 12 in medium widths.

Very exciting experience! I'm proud of you for doing it,and hope to do it myself sometime!

Please do. You will love it!

Great story and really proud of you. Even if i do not know people it still makes me proud to know that other gurls get out even when fear tries to say no.

Ty and yes that is the trick: denying your own fear.

It's so easy to let your fear take control. Good you were able to manage them. Have you been out again?

Yes I have. I try to go out fully dressed once a week now.

Wonderful, it gets a little easier to go out when you are more comfortable.

It sure does but there is still always a little bit of fear to fight back.

Red corset bustier...wiggle. :)) Wonderful!

First time is the hardest time. Once you get the hang of it it gets better. Many of us have probably had similar experiences to you - you are not alone!

Very just feels like you are alone until you find out others do it too.

It sometimes feels that we are alone in the world but looking around on EP will tell you that you are far from alone or weird. So keep dressing and be who you want to be!

Brave gurl! I have not had the courage to do that yet

The first time is the hardest and it is an occasion that you will never forget.

Well you had a night didn't you. i know what it's like going out. I did it recently and it was a blast. Read my new story "a girl is born". You were very brave to do what you did.

Thanks and i will read your story.

That sounds like quite an adventure. I am still building up the courage to go out dressed myself. Plus I need to expand my wardrobe some first.

I can understand that. The biggest thing about getting the courage is selecting and outfit that you love.

I so need to go shopping. I dont have anything I would feel comfortable wearing out.

awwww such a pity a drunk ruined a thrilling experience. You could have sobered him up lol

Well a big part of dressing in public is you need the confidence and courage to handle whatever comes your way. I did not know that as it was my first time. But he did not ruin it...he just cut it short that night. I was still proud of how brave I was and thoroughly excited with the experience.

proud of you angel X

I loved your story! I have only made very short forays out of the house en fem. No courage I guess. I have senced, to a much smaller extent, the fear and excitement you discribe. I'm sure, without you going into detail, we that crossdress and go out into public know exactly the feelings you did. <br />
I would like to praise you for a job well done with your story. Good writing, good story line, and plenty of excitement.

Thanks so much for the compliment. I do enjoy relating some of my experiences for other to read and see that they are not alone in their fears and desires.

You are very welcome. I am glad you are helping us timid fem's to learn to enjoy and not be as self consious as most of us are. We are dying to get out there and scared to try.

Thank you very much JaxSkirtz! I don't fancy myself as a great writer and so when I re-read this after posting it I felt that I didn't come close to explaining the fears , emotions, tingling nerves and excitement that came with the experience.

rndma1960, I enjoyed your story...It reminded me of a simular experience I had in a large upstate NY city. My wife and I were visiting relatives and staying at a hotel.One afternoon i got all dressed up, make-up and all. Our room was on the second floor so I had to walk down the stairs to the parking lot to get into my car. I did this with no problem. We drove downtown and parked on a street just off the main square of the town. I was nervous and excited at the same time. It was eariy evening around 6, so there weren't many people around. We walked past the court house and started around the block, walking as lady like as I could. There were some people setting at an outside cafe' on the other side of the street but no one noticed me. As we rounded the corner we came across what looked like a family,mother and some kids, I almost paniced but took a deep breath and contuined one said anything. We got to the corner and started to walk back up to the car and a guy in a pick-up truck yelled something as I was getting in the car, don't know what he said, but at least I got his attention. We drove back to the hotel and started up the stairs and were met by a group of men going down, I just lowered my head a bit and walked up to our room. I was relieved to get back to the room, but sorry the walk was over. I wish I had taked some pictures in front of the court house, but we didn't. The whole experience was very exciting for me. If you look at my pictures, I was wearing the white sweater and black skirt. I believe i wore that home also!!!

Yes I so wish I had pictures of that outing too! But at least we do have those images in our memories. One of the things I learned from that first time is to try my best to take full advantage when ever the opportunity arises now. I have seen the pic you are talking about and I think you look great in that outfit as you do in your others also.