Can you remember the first time you put on a dress ? What it looked like, whose dress

[Larissa Cassandra]

Even though I had an interest in girly things from a very early age, I didn't have a chance to try anything at all since there were no females in my home during the last half of my childhood. Much later, when the pink fog started rolling in very heavily, I tried on a few of my wife's dresses, but they were too tight and it was very frustrating! But I did wear one of her larger nighties (given to her as a gift) before I even came out to her. I told her that I loved the feel of hers, and she said why don't you wear this other one? I was shocked but very excited, so of course I initially said oh no I don't do that kind of thing. Well, it wasn't long before she "convinced" me (I had to put on some kind of fight to protect my manly image at the time), and I totally enjoyed slipping it on and savoring the satiny feeling of it on my skin. I slept in it that night, and hoped she would make the same offer in the future. She did a few times, but it wasn't until several years later that I bought my first dress in my size. My wife was out of town, so I remember putting it on and it feeling and looking so good! I tried my best to give my long-ish hair some style, and I put on some of her makeup. It was the first time I ever saw myself in an almost-complete feminine look, and I loved it!
~Larissa

[Sara1950]

I think I was 9or10 my cousin put me in one of her dresses but what I liked most was the panties and stockings she put me into first

[Robbiegirl]

Wow Sara ! She put you in panties and stockings also ! LOL Thank god your mom or Aunt never caught you all dolled up ! Great first dress experience !

[Lori Anne]

Oh dear Lord; that was along time ago. I "borrowed" clothes from my sister, and it was the 70s. I think it was actually a knee length denim wrap skirt and a blouse, and I absolutely loved it.....now, THERE'S a surprise LOL!