Wow Look what I found ! What was your Best Surprise Day of Dressing

[Robbiegirl]

I am sure for most of us this is more a fantasy but sometimes dreams do come true.

Is there a memory in your life where circumstances presented itself that you had great outfits to choose for, time, and felt daring.

Like you some how ended up alone in a theater with a huge dressing room of women's costumes and all day to try on things ?

Like some girl you knew wanted to dress you up and she had an amazing collection of dresses ?

Or I know this is bad, but you are house sitting for some women and you open her closet and find it jammed full of party dresses and bridesmaid dresses that you can fit into

Or equally bad, you are a guest of someone and the closet in the guest room is filled with all sorts of fun things !

I have tried on a few dresses while house sitting but was almost always disappointed. Hope you had better luck !

[Micki_Finn]

Other people’s clothes are most definitely not a fantasy for me.

[Majella St Gerard]

Going through someone's closet and trying on their clothes without their consent is creepy and just wrong and an invasion of privacy. Just saying.

[Tamsin Secret]

Ok so going with what I think the OP meant I have often fantasised about finding myself stuck in a women's clothing store overnight for some reason.

Let's hope there isn't cctv as I'm taking home my fav outfit!

[Robbiegirl]

Sorry I was thinking about when we were young. Some of us didn't have the internet for our first 40 years and were very alone

[BillieS]

Right after I started dressing my wife surprised me with a “costume” for a neighborhood Halloween party. It was a red dress and black hose! I wore it to the party and, somehow, found use for it on many non-Halloween nights after!

[Stephanie47]

The best I can come up with is as a teenager with a job on Saturday's I convinced my parents to leave me alone for the weekend. I needed to work every other Saturday and they should go to see my grandparents without me. The rotation at work was for a coworker and me to alternate having off on weekends. While my parents, brother and sister were away overnight I had full access to my mother's clothes.

[Judy-Somthing]

As I was growing up in the 60s and 70s my mother kept two full closets of all types of women's clothes in the attic.
Dresses, slips, girdles, stockings, etc. I would spend hours up there dressing.
She caught me one time at about 16 and said I could play with the clothes, just to put them back when I'm done.
She said I was going through a phase! I'm still waiting for the phase to end!

[OCCarly]

I came out of the closet to a woman I’ve known since high school. She owns a clothing store. She asked for my sizes and sent me a huge box full of new clothing. That was a wonderful day.

[docrobbysherry]

That's what started my dressing! A female tenant moved out and left a pile of boxes of fem things for Goodwill! Even the SHOES fit me!:D

Goodwill finally got some of the boxes with clothes/things I didn't care for!

[Beverley Sims]

I had been dressed up by next door neighbours from the age four, but I found a bra on the footpath when I was eight and this set myfuture for me.

I still have that bra!

[MarinaTwelve200]

I had stopped for about 6 years until I purchased a house in '92.----The previous owners, a woman and her adult daughter, had left Two closets stuffed FULL of clothing, some of it even new in boxes. And yes, the mother's clothes fit me. (It's how I knew I was a size 22) And it was good stuff too. Lots of it was slightly outdated '80s stuff, but I didn't care. I am not into current fashion anyway. I gave away most of the stuff to charity, but I did keep many "selected" items for myself. They made a good basis for a new wardrobe.

[Jaylyn]

Not a day of dressing but mom always put old dresses in a sack or box to carry to our local Church were they found people that needed the clothing. I used to play dress up from those old sacks he would put in the shed out back. Mine wasn't a surprise but I kept a few out and hid in the barn when she discarded something I liked.

[Jillian Faith]

Ok so going with what I think the OP meant I have often fantasised about finding myself stuck in a women's clothing store overnight for some reason.

Let's hope there isn't cctv as I'm taking home my fav outfit!

I've had the same fantasy of being locked in a department store overnight and having the run of the store to try on all of the women's clothes, shoes and wigs. Also tried on Mom's clothes from the clothes hamper in the bathroom when AI was suppose to be taking a bath or later when I was old enough to be left alone at home. Luckily I was never caught and if she knew mom never confronted me.

[CarlaWestin]

Ok so going with what I think the OP meant.....................

I've actually had many opportunities nearly similar. Well, 'cause I'm old! Anyway, one that comes to mind was when I was the lone overnight facilities worker/security for a major shopping mall. After clocking in I was informed that several racks of ridiculously expensive fur coats for a fashion show were locked in the general manager's office. I had such a wonderful time trying on hundreds of thousands of dollars worth of coats and jackets. Throughout my career, there were many times that I worked in homes all day after the owners left for work. It's amazing how you can memorize exactly how things are folded in drawers!

[stephNE]

When I rented my office space, the unit next door to me was occupied but people were rarely there and there were no signs. Occasionally I saw a few people come and go and eventually I asked one of them what was going on. They told me they were a company that provided uniforms, and they used the space to store clothing that wasn't in use. I asked if I could see, and they showed me all sorts of clothing for a major hotel chain: uniforms for managers, front desk staff, cleaning, maids, restaurant waitresses, etc. I have thought so many times how much fun it would be to get in there and try on all of those.

[Tracii G]

These stories are pretty good LOL.
I never had dreams like some of you and I feel I missed out somehow..
Carla you are such a bad girl :D

[DIANEF]

Working as a supervisor in a retail store gave me access to all the keys for the entire store, including the area where the staff uniforms were kept. As the women wore skirts and blouses I often wondered how I would look dressed the same. One day I decided to find out and 'borrowed' a new unworn set. It wasn't quite as good as I thought and I put it back the next day, but at least I did get a picture of it on.

[Tracii G]

Pics please Diane LOLOL

[DIANEF]

Just for Tracii. I should have put a little name badge on really!!

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[Tracii G]

Thats cute for a uniform I would have tried it on too.

[DaisyLawrence]

I'm trying to see if I can think what store that was Diane, should recognise it really but just can't put my finger on it yet.

[Robbiegirl]

Just for Tracii. I should have put a little name badge on really!!

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Love the Uniform !

I worked at several restaurants in the 70s where the women had to wear short frilly cocktail dresses always wish I could try one on for fun !

[Pumped]

Not as interesting as some, but I worked at a service station in high school. The boss would bring in garbage bags full of clothes for shop rags. One day I reached in and pulled out a bra! After that in the evenings when I worked alone I would dig through the bags and see what I could find. Most was way out of style or huge granny panties but I would run across a gem once on a great while. I still remember the feeling l would get when I found panties or a bra that was a nicer style in my size. I had one real nice bra and panties, a couple tops, shorts and a skirt that were keepers. When I got married it all went into the trash and that was the end of dressing for thirty five years.