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My First Time Crossdressing

My first time crossdressingWhen I was about 12 I did a paper round in my local area and I used to deliver to an older lady she asked me to do some chores for her . I agreed to moving some boxes for her on the day in question I turned up to see what the job entailed just moving some boxes into the loft for her.

She had 3 daughters all now left home and these where spare clothes that where left behind Them Margret the lady said she would be out shopping and had left me some lunch in the kitchen for when I got hungry.

So I started moving some boxes and came across one that was partly open showing off the local girls school uniform I took this out it was a gorgeous plaid skirt, a navy blue blazer and a white blouse.

Well I could not wait to try these lovely garments on I shrugged my boy clothes off and started with the tights then blouse and skirt. I then rummaged around the box for shoes and came up trumps with a pair of girls loafers with a 2 inch heel these fitted perfectly then I put the blazer on at this time I was feeling a bit peckish and went down to the kitchen the sound of those heels clip-cloping on the kitchen floor was music to my ears.

I had my sandwich and juice then headed back upstairs to move more boxes. I soon forgot the time and came down the loft stairs straight into Margaret I was shocked and tried to stammered some excuse out but Margaret just held her hand up and said so you like to dress as a girl then I think that we are going to have some great fun this summer.

Submitted by Kevin

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  1. Thank you so much for publishing my story I love that it’s in print and others can read it I get such a buzz out of seeing it

    1. Hope to hear about the fun you had that summer.

  2. Would love to read more stories…i 2 love 2 dress up in girls clothes…and love 2 go shopping for sexy clothes

  3. That was a great story, I loved it.

  4. I started about 12 when we hit the Sears catalog and I loved the girdle and panty section. That led me to trying on girdles I found around the laundry hamper. I got away with it until my mom found my cum stains in one of them. Busted. Went on from there to full dressing after I turned older. I still do dress at age 75. Fun, fun, fun.

    1. Fun, just playing around

  5. dressing at thei age you said bet your lovely

  6. Nice one I use to dress in my girlfriend uniform she love it on me started at age 7 still dress up now
    You always see me in panties. Love to dress up. Even my gf buy me sexy new and used. Be proud what you our I am.

  7. I like been a cross dresser i have been a full time cross dresser for the 17 yrs i started to be a cross dresser when i got my 1st pair of women’s boots i pay $20 for them from k mart back in the 70,s.

  8. I started seriously when I was about 16/17, I’d done it before then, but I thought of it as a phase I was going through but crossdressing never leaves you & I’ll never forget the look on my older brother’s face when he caught me dressed as a schoolgirl wearing a navy pleated miniskirt & 4″ stilettos, when he realised weeks later, I was a serious crossdresser his got girlfriend to do my makeup/nails & hair. & I found myself been taken out that night, WOW what a night, I’d always been rather envious of girls wearing minidress & high heels & here I was dressed to the nines enjoying myself

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