How did you get into dressing?

[Fiona pink]

It was a cold night sometime in the early 60s and my pyjamas were worn out so I was given a pair of pink brushed nylon pyjamas that belonged to my sister. When I got a new pair of boys ones and the pink ones taken away I was more upset than I had ever been before, I never said anything to my mum , but I started sneaking into my sisters room and trying on her clothes, and then as I got older I would wear my mums clothes whenever I got the chance

[Kimmi]

How sweet, young lady!

I read your bio on your profile page. How lucky for you to have an understanding wife.

And what a deal for her to have her maid!

Kimmi

[Tracysmokingwhore]

I was 6 when I was dressed in girls clothes by my mother was to put in dresses panties training bras Mary James to punish me for my unruly behaviour and troublesome acts to teach me a lesson and then develop more as mother was enjoying doing it punished spanked humiliated done to me in front of my sister an some of her women friends and eventually taught how to take cock like a girl as with strapon dildo I was turned more slutty looking put in chastity by mother.

[Glenda]

Brushed nylon pyjamas are excellent as sissy punishment nightwear and always induce floods of tears when correctly implemented. They are perfect for sissy to wear around the house while doing household chores and always attract derision and compliments in equal measures from guests when sissy answers the door to guests.


https://www.flickr.com/photos/41163807@N...ateposted/


https://www.flickr.com/photos/41163807@N...ateposted/

[Sissy Sandy]

I was always quiet a masculine guy and decided to try it for a laugh when nobody was in one night
then I realised it was no joke
I loved it
I loved they way it looked and it felt
I have never looked back
when I was younger I would have made a great looking femboi
I wish I could find a woman in the UK to feminize me
It's my biggest fantasy now

[Dena]

I have 5 older sisters, while I was never dressed up by any of them, their clothes were everywhere!

I'm sure I watched more Beauty Pageants than my male peers. I discovered the lingerie section of the Dept. store catalogs and when I was around 8, and began to have dreams of being in public in my underwear, usually a nice lacy full slip. I even had a dream about two girls who wanted to dress me as a girl, I woke up when I was presented the entire outfit they wanted me to wear.

A pair of my sisters' tights was the first piece of girls' clothing I wore. One day I was going to go ice skating, and my long johns were in the wash. My mother had me wear a pair of my sister's tights instead, I had a fit, and one of my sisters amusingly helped me into the tights. I was paranoid at first, then began to enjoy the way the tights felt.

When my mother did the laundry she would leave a laundry basket with sheets in our bedrooms for us to make our beds. Many times while making my bed a pair of nylon full brief panties would come floating out, which I would return with the basket. So I got familiar with nylon panties, and began to compare them to my underwear. Then the day came that I chose to try on the panties to see what they really felt like! They flt so good! Unlike anything I'd ever worn. I couldn't believe how good it felt the first time I wore a full slip, bra, panties, garter belt, stockings, and high heels! Like I died and went to heaven!

[Girlygirl]

Those sound lovely experiences are a and your finale there must have been quite something. I wore similar items together as a child but in my case while under punishment and at a stage in my life where I was not yet wise enough to appreciate my femininity so I envy you on that score.

Why do dreams always end just as you get to the best bit? 

[Satin Jessie]

Unlike nearly all the other posts on this thread I had no childhood experiences of dressing up, no sisters or cousins clothes to try on, but I was always envious of girls clothes. I've never wanted to dress as a woman, it was always little girls dresses with lots of frills and bows.
It was always something I thought about but never acted upon until , about four years ago, I had a pretty traumatic break up from a toxic relationship and that spurred me on to try things that I'd always wanted to do.
The first time I put on a petticoat I knew I'd found the thing I'd been looking for.

[Girlygirl]

That’s a lovely story and great that you made such a positive experience from the remnants of a negative one. 

[subjami]

hi,
At age 13 I start to explore my mom stuff. Her heels and panties and bras and pantyhose and dresses and skirts and blouses . She only worn pantyhose. I even tried even her one piece swimsuit. I dress for a while and she knew and came out dressed to her a year later and she wasn't happy and end making me see a Dr for help which didn't work out
and even tried to blame my folks marriage or my time with each of them.They end up stopping the visits.