Starting Out

I think it was 8 or 9 I first started thinking about and then trying on women's clothes. It was a gradual progression that began with just innocent thoughts of 'thats a nice dress' while I was looking at the pictures in the old mail order Kay's cataloges.  I know it was not a sexual thing and despite being taught that being a boy meant i dont wear skirts and deesses I wanted to feel what it was like to wear the clothes that I saw. So my first item of girls clothing I wore was a skirt. It was one of my mums; a below the knee length skirt, layered  underneth with 2 or 3 cotton petticoat slips. I do still really remember the absolute joy I got from wearing it. It felt just like I imagined it would and more. The fabric danced around me, something I later realised was unique to that skirt and it's petticoat under slips pushed outwards, while tickling me at the same time. I loved that skirt and I still like designs like it. 
Surreycrossdresser Surreycrossdresser
36-40, M
4 Responses Aug 11, 2012

I started dressing when I was 8! However I never went for my mums stuff! I would go shopping and find panties my size!

You are sooo brave

If asked I would tell them it was for my twin sister!! So we would be the same size!! Smart move for a 8 year old!!

I started at about the same age as you wearing my Mother's silky knickers and sometimes one of her nighties.

Petticoats and nighties were always my favourite and still are.

I love wearing a nice silky petticoat with lace hem.

Camilsoles are nice as well. Underware has to be lace trimed as I so love the delicate embroidery involved.

The first time I remember was a bridesmaid dress. It had many la<x>yers of skirts like you describe. The full story is in this group.

My mistake. It's in the group 'I like wearing dresses' x

That will explain why I could not find it! I'll look now.

That sounds wonderful. I could not find the story in either group. Maybe message me it one day. I would love to hear it.

Oh yes the first time is wonderful. Read my story about the first time I crossdressed. How my mother dressed me as a girl. It was heaven alright. I think you would like the story.