My First Skirt

I've been cross-dressing for as long as I can remember and will never forget when I purchased my first skirt. About 25 years ago I was living in the UK and got my own place, so decided it was time to get my own clothes (rather than sneakily trying on my mother or sisters stuff).
I went to a local indoor market and went to a ladies wear stall with the story I was going to a fancy dress party as a woman and needed a skirt. The lady was really helpful and we ended up choosing a knee length grey pencil skirt with a split up the back and two small pleats at the front. As soon as I got home and tried it on, there was no turning back.
The following week at work, one of the girls in the office came in with exactly the same skirt. Oh how I wanted to chat to her about it, but wasn't that brave.
A few weeks later I was out with friends and one of the wives turned up with a beautiful black pleated long skirt - all the girls in the group were complementing her on it, while the guy's talked sports or some such thing - I knew which conversation I wanted to join.Needless to say I went out the next week and got my own black pleated skirt and I was off down the happy road of cross-dressing.
I love shoping for womens clothes and hopefully will post a story on that forum soon - I have progressively got braver and braver, to the point I openly discuss the dresses or skirts I'm looking at with the shop assistant and ask for opinion in the changing room. I live in the US now and go to womens stores (Lane Bryant, Dress Barn, Avenue due to my size) and have always had respectful and friendly service. Going to general stores like Target and Kohls doesn't have the same challange, or give the same buzz.......
michelletrans michelletrans
51-55, T
12 Responses Dec 2, 2012


Shopping for women's clothes is so much fun. Like you said, most places are very helpful and respectful. Perhaps there are more of us out shopping than we realize.

I think you're right it must be a fairly common thing as the clerks I've run into hardly batted an eye and were very respectful and helpful. Now if I could just find a cute bra with a 48" strap size that's not prohibitively expensive. :)

I always get so jealous when I hear women being complimented on the dress they are wearing. I have many pretty dresses and would love to be accepted as one of the girls and have all the other girls compliment me on my pretty dress.
I don't crossdress to attracted men. I crossdress to feel like one of the girls and dream of being accepted by them.

That is sooooo nice.....

I can agree with almost all of this, oooh how I love seeing a woman wearing something I own also, and wish I could converse with them about it! I don't Always desire the conversation when I'm out shopping, but many years ago, probably 15, oddly enough, I did initiate conversation at Victoria's Secret, the salesgirl noticed I had two different sized bras and asked if I needed help, and I actually was buying for my gf at the time, so we picked out the appropriate sizes, as they didn't have one of the two in the same color I wanted, very delightful! She and the other two girls elected to tell me how they would find their lovelies stretched out from their husbands apparently wearing their garments, I just guess that they knew allthe items I was purchasing weren't just got my gf, overall a lovely convo....

I get most of my things at thrift stores. There is no one to assist you, so you are on your own. I really enjoy looking through the racks. You would be surprised at all the sexy things you can find. I always try everything on first. The sales people in the stores do not care what I try on. They are just interested that I do not steal anything. This way you can have a nice, sexy wardrobe and not have a lot of money invested.

What great fun!!!!

I have to agree with the others for clothes is one of the best parts of cross dressing. There is such a variety of women's clothing out there that you can get on a mission to own one of everything. Not the best idea but always a tantalizing thought. I do shop in Kohls, Penney's, Macys, Target, Shopko, Ross, Dress Barn, etc. To date I haven't tried on too many things but if given an honest invitation to do so by a sympathetic sales person I will take it. I will also try out Lane Bryant, they sound like good people.

I have never had a bad experience in either of the stores you mentioned. First I loved to shop around Christmas because I could always say I was buying for my wife. Then one day I was holding up a skirt to check size and a female voice from behind me asked if it was for me, I turned and it was one of the workers, at fist I was going to say no, for my wife then decided what the hec...and told her for me. She then informed me that there try on rooms were all separate and if I wanted to I could try on some clothes. From that day on I just go whenever I get the chance to shop and shop for the way, the store in my story was Lane Bryant.....

Wonderful, evocative experience for you. Living in the UK there are not so many [classy, sexy, shops] I plucked up the courage before I was 'out' to anybody except mum, to go to Ann Summers shop. I was delighted at the friendly greeting I got from the staff. They were so helpful with telling me about matching clothes so that I didn't look awkward. I remember buying my first ankle length skirt, hip hugging, the feel of it as I walked was really wonderful. I felt so chic, and the girls advised me not to wear suspenders with a figure hugging skirt, but to wear hold up stockings. I was disappointed because I adored wearing my suspender belt, suspenders and stockings, but the suspenders would spoil the line of the skirt. I will ever be grateful for the kindness of those shop assistants. Your experience really thrilled me, thank you so much.

Thanks for your comments - love your photos - very classy!

I was the same in Australia..a very kind,but receptive lady helped me choose the right size basque and matching panties ( she guessed rightly they were for me and never passed comment on the fact )
I went to her many times and struck up a long friendship which culminated in me taking her out and sleeping with her... I was 44 and she 59
She also helped with my dressing and make up - I did tell her I was bisexual too,but she fully accepted that side of me


After I came out to my wife, she made it clear that she didn't want me wearing her clothes (I still do). We both wear about a size 7-8. She was good with me buying some of my own and even gave and bought me a few things.

I immediately went out dressed (cute tight white capris, wedge heeled sandles, and a cute pink blouse, to a second hand store and bought a couple of beautiful pencil skirts. The clerk asked of I needed assistance and I told her I was "fine" shopping on my own. She politely smiled and told me to just ask if I needed anything. She was very nice. When I made my purchase, she called me "sweetie" and told me to come back anytime! I felt like such a real girl! I was in heaven.

Like you, I absolutely love (tight) skirts!


It is such a great thrill and wonderful feeling when the shop assistants help out with advice and comments
Your next step is to get a professional bra fitting that bakes a big difference
Good luck in the future

Fabulous sweetie