My very first time !

So today after cleaning up my garage, I decided to dress up and enjoy my evening. Then a whim came over me. All at once I found myself driving the 10 miles to town in black thigh highs , a burgundy pencil skirt, (i hiked it up mid thigh). A black spaghetti strap top with a knitted short pull over. I grow my hair long so I let it down and headed to town to recycle my recyclables. In a town of 3500, if I was seen I would have been noticed, but I did it anyway, I was careful and smiled the whole way. Nobody noticed me, I'm sure and it was uneventful. But, it was my first time out, I'm positive it wont be my last!

Sounds awesome Ricky - I'm proud of you!

Congrats! Hoping u enjoyed..

First time is definitely the hardest.

It will get easier and less stressful.

How great it must feel - big congrats!

Hi Ricky, The first time is the hardest, but what a rush. Glad you got out, waiting to hear about your next time.

About twenty years ago, I went out on my errands dressed as a witch on Halloween. I joked that the ex wife got all my money and I got left with her clothes. I had a good time at the mall and noticed that many women seemed not to notice that I wasn?t a woman when they passed me. That gave me the courage to try another outing.

I dressed very plainly in a long denim dress and went to a distant mall. I was beginning to chicken out but I had to use the restroom. The first store had bathrooms way in the back so I figured that I would have privacy. Wrong! Women kept entering and leaving. I just went in, did my business, washed my hands and left. No problem there or anywhere else . That got me hooked for a while.

I did my first real outing just the other day. I was wearing a skirt, top and wedge sandals from Kohls. The only thing missing was hair and makeup. I drove for six hours from Stockton CA to home. I stopped for gas twice, at Costco so you know it was crowded and I was seen by several people, and went through a fast food drive through. It was a thrill and can't wait to go out again.

I think the best way to get your feet wet is to invent a purpose for being out and about. I've seen a lot of Youtube videos of cross dressers walking up and down empty parking lots at closed commercial strip malls and the like. Surely on video cameras and a great way to attract attention. If you run an errand in a place where that is expected I think it will offer more comfort than aimlessly walking around.

In the beginning I created brief trips. I would return library books to the night return slot, mail a letter at a post office, grab a newspaper from one of those free newspaper boxes. On a more lengthy outing I take a stroll in the early evenings in a very safe residential neighborhood that has two grocery stores. I carry a tote with the name of one of the grocery stores so it appears I am returning from a shopping trip rather than just aimlessly walking around. I think, if one appears to actually be doing something normal, it does not attract attention. Walking aimlessly up and down a busy street in a short mini-skirt (I've seen those posts) will definitely attract unwante3d attention and interactions.

Yes that can be a wonderful experience. I don't go out dressed, I o take car rides dressed.
it can feel great knowing you are being you, and nobody see's or cares.

I would love to do the same thing, Ricky. You should be happy, proud, and thrilled of your first trip out. My issue is not whether or not I'd be noticed because I know I would even if I were 100%m passable (which I'm not). My issue is my car is 1 of 2 produced by the manufacturer so everyone I know also knows my car. It's a dead giveaway. That is why my first public presentation (if it ever happens) has to be in a town where nobody knows me. You are one brave girl.

As I said a few times before, once you realize that no one will laugh or point at you.... you are passing.
It's all how you carry yourself and have the mindset that you are just wearing the lingerie and clothes that is normal for females to wear and are not doing anything out of the ordinary.
If you act nervous, you will just attract unwanted attention.

MY first time out dressed was in 2004 for our Adult Sunday School's Halloween party. The year before I had noticed that our costuming had dropped way off and I decided I would do something DRASTIC the coming year to "shake things up" ---I thought about and rejected just dressing as "A woman" as THAT lacked "imagination" (I am closeted anyway). One day, however the perfect "inspiration" hit me. I would dress as a "GYPSY FORTUNE TELLER. Perfect! It was Halloween themed, I got to "bend my Gender" and got to wear over the top exotic clothes and makeup. Needless to say, I was the "HIT" of the party and won first place with my costume. It's a great way to meet the ladies too ;) they ALL lined up to have their "Cards read". we ALL had lots of laughs and lots of fun. And my PLAN to revitalize the costuming worked TOO well. Next year, I was a dead -on MARK TWAIN but only won second place --defeated by an 80 year old "Pregnant nun".

I bet it was very exciting! Congrats!!

:cheer::cheer:

You remind me of me in a way. It is kind of interesting how some will tone down their first outing to the point of wearing something minimally feminine like jeans and flats. You took the other route - wearing black thigh high stockings and a skirt pulled up to appear very short is quite noticeable to any casual observer. I did the same back in 2017 when I wore all lingerie into a bar. It was quite the thrill for me as well as I also had black thigh highs on.

It is weird how the so called pink fog can make us throw all caution to the wind. Of course I was hundreds of miles from home when I did it. Note that this can be quite addictive, but fun just the same. Just be careful.


Sandi

From personal experience I can say you've more chance someone will recognise your car.

Some years ago my SO went to visit friends so one evening I went out for a drive dressed. On the way home, stopped at lights the car behind me started flashing his lights. I realised it was someone I knew. Thankfully within a few hundred metres we went our different ways but it certainly had my heart going.

It's really fun, isn't it? I like to take a drive and feel feminine in a typically male setting for me. I have to be careful of my route because I live rural and have a somewhat distinctive vehicle. I have to position my legs different, and that's part of the charm.

Thanks Ladies, I just decided if I was going to go out and about, I just needed to do it and off I went, Id talk myself out of it if I thought too much about it. This is what i have on and I'm going! Yes I was worried , YES I was nervous, But I had to do this in order for me to be me. SO I did it and will again! SOON!

Ricky, obviously worth the risk.

You've really gone and done it now!