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View Full Version : Dressing in Public - My first time wearing female clothes as a man



KlaireLarnia
10-08-2010, 05:33 PM
Hi, This is not going to be a short post - so I hope you are all sitting comfortably.

Shortly after joining here I asked people if they have ever worn female clothes in public without trying to pass as female. I.e. wearing female clothes while being obviously a man.

I got a few positive comments and a couple basically said that people take only a cursory glance at you and then ignore what you are wearing. This got me thinking. I occasionally have to travel away on business and when the next one came up I was hoping to try and wear something in public and see how it went and felt. This is my experience of what happened yesterday and today.

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I live and work on the south coast of England and I had to travel to Manchester yesterday for a business meeting today. I would be driving there (around 4-5 hours), staying in a hotel and then driving back today. I planned what I was going to do for a week. I bought a new woman's top, a pair of flat court shoes and a pair of 3" heeled calf boots. I sorted out a skirt, a long woolen warp-around cardigan. I also sorted out a little make up (nail polish which is part of my good luck routine each night before the meetings & some brown mascara). I also took a woman's shoulder bag as well.

I packed my case with all this and my business clothes and went to work as normal yesterday (just to point out, I wear jeans and t-shirt at work, and a suit for business meetings). When I go away I get a hire car, so when it arrived I loaded it with my case and bag. I left work at 2:45pm and went about 5 mins up the road and pulled into a lay-by. Here I changed into my female top and cardigan and changed my trainers for my flat court shoes. I then carried on my way. Knowing the bulk of the route well, I knew I would make 2 short stops for a toilet/comfort break along the way. These would be my first experiences of wearing female clothes in public.

The first, was around 1 1/2 hours in, a simple and short toilet stop. The place I would stop would be near empty so it would give be minimal exposure - which I thought a good thing. I got out the car and was in to the toilet and out as fast as possible. I was very nervous and worried as to who may have seen me. And was glad it was over. It felt odd and sort of wrong, but it did not deter me.

I carried on driving, about 2 hours later it was time for stop two. This time a motorway service station on the M6 just after the north end of the toll road for those who know it. I knew this would be more crowed so my exposure would be increased. I kept my flat shoes on, but removed the cardigan and swapped to my male zip-up sweater which was about ¾ done up. So in I walked, I went to the toilet and then into the shop to get a drink. Once done back to my car, I sat a moment and thought - they were right, people DO ignore you...

I then traveled on to the hotel in Manchester. Once in my room I prepared for the next part, which would increase the stakes a little. I get a meal in the hotel, this means going to the restaurant and eating with others around me. In my room I changed my dress slightly. Removing the court shoes and putting on my boots, but allowing my jeans to cover them. So while it was obvious I was wearing heels, you could not fully see them. I was still wearing the top I had on for the whole journey and my male zip-up top which was half undone so you could see the top under it. The restaurant had around 6 people in it and as I walked in I saw people look as they spotted my heels. Two guys a couple of tables away kept looking at me as if wondering what/who I was. Either way I was not bothered, I was comfortable in how I looked. That is all I cared about. The staff members (a man and a woman) treated me as any other person and made me feel a lot more comfortable there.

When I had eaten I returned to my room to wash and get ready for bed. My normal routine is to have a bath/shower, paint my nails (clear on my fingers, red on my toes). I then put on my nightdress and went over my documents for the meeting today before heading for bed and some sleep.

Today I got up at 5am, breakfast was at 6:30 onwards. Again I was to take another step forward in what I wore in public. Again I put on my jeans and boots - this time with my jeans tucked inside so you could see I was wearing calf boots. Again I had a female top on and not a male t-shirt and my zip-up jumper. When I got to the restaurant there were 6-7 people in them - all male. So in I walked with my boots on and had breakfast. This is a self-service all you can eat. So you get assigned a table and then you walk up and get your food from what is on offer. This means people DO see you as you walk to and from your table. Again I saw the stares and looks as people saw I was wearing heels and almost questioned as to why. But again I did not mind, I was comfortable and happy.

After breakfast I went back to my room and changed into my suit and business clothes; packing my female items so I could gain access to them again when I was ready to drive home. I look the stuff to my car and went to the meeting. I was all done by 11:30am and walked back to the car. There I sorted out my female clothes and changed into them in the front seat of the car. Once changed clothes, I walked to the pay-station to pay for my parking and headed home, putting on my court shoes for driving.

Again I planned 2 stops on the way home - roughly the same as before. So on the way back I stopped at the same service station on the M6, this time putting on my heeled boots (as opposed to my court shoes I had on last time). I had my money, wallet, phone etc in my shoulder bag. Placing it on my shoulder and using my woolen cardigan to cover it - in I walked. A man in heeled boots and a woman's long woolen cardigan. I went to the toilet and then into the shop while wearing these items; the bag mostly hidden from sight. When I got back to the car I felt really good. Yes I saw the looks. Yes I could almost hear people asking what I was doing or thinking. But again I was still not bothered.

On I drove.... the next stop was Warwick Services on the M40. Here again I wore exactly the same items. Again it was a crowed place (always is for anyone who knows it). Again I walked in, the only real difference this time was that I had a little further to walk from the car to the building and I was not so conscious of hiding my bag from sight. Whereas before I made sure no one saw it, this time it became visible a couple of times but again I was not so bothered. The looks came again, but this time I could almost hear people saying - I bet he is gay and ignoring me. I am NOT gay, but if it helps people accept what I am wearing when that is fine with me.

So I carried on, I had to stop a third time due to being a little tired. I stopped at the last services I would pass before I got back to work. Here again I walked in as before. This time something funny happened. I got a can of Red Bull from the shop (to help me wake up a little as I was under an hour from work and knew I was feeling tired). I went to the toilet while there as well. I did my business and stood there drying my hands by the entrance to the toilet. A guy walked in and stopped. Now a lot of men walk looking at the ground, so as this guy walked in the first thing he saw was a pair of high heeled boots. And then he stopped. Looked, looked up at me, looked down and looked again and then walked in realizing he HAD got the right toilet and had not walked into the women's toilets as he initially thought!!! I found this highly amusing, as the confusion on his face was a picture. His face had one of those “WTF???” looks on it. Brilliant!

After this I drove back to work. Changing my boots for my trainers before I got there and putting on my male jumper to cover the top I was wearing. And this was the end of my experience.

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So how do I feel for it? Well personally totally over the moon. The reactions I got where not as bad as I thought they would be. People DID ignore me after a couple of glances. I know I can walk into a place in my boots and top and still be accepted. That people will not shun me. I know the next time I go away I can and will do this again, but this time I will wear my bag as a woman does, on my shoulder in plain view. It does not matter if people see this; they will just assume something they are comfortable with and accept it/me. We as people put things in boxes so we can deal with them – this is how society works.

The only thing I could not bring myself to do was wear a skirt in public. I am not sure if I can take that step while looking male. This to me seems like a step too far and something which would cause me problems if I did. I am not sure if others would agree with me or not, but despite having a respectable denim skirt on me, I could not walk out in it. I had to have jeans on.


So anyhow, this is my experience. It was one of the best things I have done and I wish I could do it more. Sadly I am not due to go away again until the middle of November, another month to wait. This will be hell I know as I will want to go out in my boots etc – but cannot. Still the next time I also know I will move another step forward. The bag on show, different clothes as it will be winter, I will have more confidence in how I look and will be treated.

So there you go. I had to share this with you all, as I am VERY VERY proud and happy with myself for doing this.

Klaire
:D :) :D

helena.gcd
10-08-2010, 07:00 PM
wow, you are really brave!!!
i'm glad that you didn't have any trouble and that people reacted well to your outfit.
Most of us are really scared of what will people will say to us, but if you think about it, when we are on the other side and see someone who's behavior is beyond what you are used to , most people are really polite and won't start laughing or pointing at them, because people doesn't mind what others people do, as long it is harmless to them.

Zoe Dawn
10-08-2010, 07:07 PM
Glad it went well for you. :)
Good luck with your next trip.

KlaireLarnia
10-09-2010, 02:03 AM
wow, you are really brave!!!
i'm glad that you didn't have any trouble and that people reacted well to your outfit.
Most of us are really scared of what will people will say to us, but if you think about it, when we are on the other side and see someone who's behavior is beyond what you are used to , most people are really polite and won't start laughing or pointing at them, because people doesn't mind what others people do, as long it is harmless to them.

I agree with this. While most people do have issues with it - and I understand why as it is outside the "normal" - in reality people are not that bothered as long as it does not cause them any direct issues.

Yes you get odd looks and stares, but as long as we can ignore these and deal with it, there is no real problem there. I am quite certain there where a few whispered words from people out of my earshot but again that is perfect normal and causes me and them no harm. The way I planned it for Thursday/Friday and the steps I took to increase my exposure as it where, worked well for me and each time gave me more confidence in both what I was doing and how I looked. And while looked like a man in heels and women's clothes - reactions where surprisingly good and that is what mattered.

The other good thing is that I now have time to reflect and plan the next time I will be able to do this. I can get clothes that will suit the weather better and make sure that i look right again. I may try and take the makeup a little further as well perhaps. At the moment I will not be wearing a wig as I am not trying to pass as female, just as a man in female clothes. It is nice to know that while I am away on these trips I can be myself and not worry too much.


A question for anyone who cares to answer it. Given my positive experience above - has anyone worn a skirt in public while not trying to pass as female? This is the one part I could not do yesterday and I am still unsure of it.

JiveTurkeyOnRye
10-09-2010, 02:51 AM
A question for anyone who cares to answer it. Given my positive experience above - has anyone worn a skirt in public while not trying to pass as female? This is the one part I could not do yesterday and I am still unsure of it.

Yes, I do it quite frequently actually. I have posted about it a lot, but if you want to read a long post I just made on this very subject, you can find it here in this thread (http://www.crossdressers.com/forums/showthread.php?140852-I-want-to-go-in-public-as-a-man-in-a-skirt-advice&p=2285804&viewfull=1#post2285804)

Or you can feel free to pm me if you have any more questions.

Brendastevens47
10-09-2010, 08:14 AM
Loved reading your experinece. I have wished I could be so brave. I have underdressed many times and dressed fully when outdoors but not with others around. What an absolute thrill it must have been for you and it was so wonderful to read how others responded to you dressing in a feminine manner.

.Thank you for sharing your experience. What a wonderful story.

Emma England
10-09-2010, 08:32 AM
A question for anyone who cares to answer it. Given my positive experience above - has anyone worn a skirt in public while not trying to pass as female? This is the one part I could not do yesterday and I am still unsure of it.

Yes, so many times I have lost count.

Must be hundredes of times, especially in warm weather.

KlaireLarnia
10-09-2010, 08:51 AM
Loved reading your experinece. I have wished I could be so brave. I have underdressed many times and dressed fully when outdoors but not with others around. What an absolute thrill it must have been for you and it was so wonderful to read how others responded to you dressing in a feminine manner.

.Thank you for sharing your experience. What a wonderful story.

The thing I have learnt through what i did this week is this:

1) No one really cares. As long as you are not offensively dressed or being a nuisance most people will ignore you.
2) Yes you will get looks and stares. But stand tall and ignore them. People see what is different and then box it away under something they are comfortable with. Makes no difference to you.
3) Start small, work up. This is what I did in the space of two days. Each time adding something or making something more obvious. It builds confidence without requiring a massive leap of faith.
4) Be yourself. As long as you are true to yourself it will work. Being true to yourself, adds confidence to the above and helps strengthen your resolve.

Tomorrow I need to travel 250 miles to grab a large quantity of womens magazines I won on ebay. I will be going alone. If all goes to plan (and I can sneak out what I need) the person will see a guy turn up in heeled boots, a shoulder bag and purse. Am I bothered by this? No. Why? Because I know I am comfortable with how I will look and that the person will do a double take and then just deal with me. My money will be perfectly good for him. Yesterday thought me a lot about myself and how others see me when dressed. While I would never do this in the local area, going places where I have a million to 1 chance of seeing someone I know is totally fine.

I am VERY pleased with what I did. It took a lot of guts, but was well worth it. It taught me a lot about myself and how people perceive others. The only awkward spot was going in the mens toilets dressed in boots, a flowing cardigan etc and seeing a crowd of men there. I had to dive in a cubical to go to the loo and not stand at a urinal as normal... But I was perfectly happy being seen when washing/drying my hands.

Klaire

MrKunk
10-09-2010, 01:13 PM
Really awesome experience, keep bringing us the news, your really daring and it makes us want to do more.

Linda St. John
10-09-2010, 02:09 PM
Very upbeat, Klaire. Thanks for giving all of us a happy ,positive feeling ..

Butterfly Bill
10-09-2010, 07:27 PM
You'll be wearing skirts soon. I progressed thru knit pants and then skorts. Keep pushing the envelope

Nick2Nikki
10-10-2010, 12:42 AM
A guy walked in and stopped. Now a lot of men walk looking at the ground, so as this guy walked in the first thing he saw was a pair of high heeled boots. And then he stopped. Looked, looked up at me, looked down and looked again and then walked in realizing he HAD got the right toilet and had not walked into the women's toilets as he initially thought!!! I found this highly amusing, as the confusion on his face was a picture. His face had one of those “WTF???” looks on it. Brilliant!

Hahahaha! Priceless! :laughing:

Dian077
10-10-2010, 08:52 AM
Originally Posted by Klaire Larnia
A guy walked in and stopped. Now a lot of men walk looking at the ground, so as this guy walked in the first thing he saw was a pair of high heeled boots. And then he stopped. Looked, looked up at me, looked down and looked again and then walked in realizing he HAD got the right toilet and had not walked into the women's toilets as he initially thought!!! I found this highly amusing, as the confusion on his face was a picture. His face had one of those “WTF???” looks on it. Brilliant!

LMAO......I would have done the same thing and most likely had the same look. I can not count how many times I have walked into the Womans restroom :o. Especially these new ones that done have doors, just little maze thing.....:D

KlaireLarnia
10-11-2010, 12:35 AM
I just wanted to add a little update.

Yesterday I had to drive around 140 miles to Coventry and back to collect a load of womens magazines (around 300 it turns out). The plan was to sneak out my boots and cardi and basically turn up looking female and see what reaction I got and also give me another taste of dressing in public.

The drive up was fine. But my toilet stops where more uncomfortable than the last time due to there being more people around.I was more wary due to there being children around and more "youths" who where more likely to make a comment about me. I also noticed a LOT more stares and odd looks. One of the girls who served me in the services shop really did not know where to look, you could see she was uncomfortable as she spoke in a very low tone. So this kinda showed me it is not simple and that even I have some confidence to build up. In smaller crowds I am fine, in large crowds I am not.

However when I got to the house I was to collect the magazines from. There was NO issue at all. There I was in a womans top, cardi and heeled boots and the two people (a retired couple) treated me like I was dressed as normal. They addressed me by my male name, spoke kindly and nicely. It was a lovely experience. They had no issues - then again they really just wanted my money and the magazines gone so this could be part of it too.

I am now planning for my next trip which will be in November. I have ordered a female coat to wear and a couple of new bags. I will look to see if I can get a new pair of shoes too next month and then see how it goes. I am looking forward to the trip and hope it will reinstall a little confidence which has been knocked this weekend.

Klaire