Start as you mean to go on
Read This Blog
Discover real stories, advice and experiences from the Club CrossDressing community.
Join free in under 30 seconds.
Already a member? Login here
How did I start on this rocky road of dressing? (hint – don’t wear hiheels on a rocky road…)
My first attempt was purely accidental when I was a young ****. I think my Mum hadn’t completed the laundry, or something, and I needed a shirt, maybe a T-shirt, to go out and play. She tossed me this black shirt I didn’t recognize and said that’d have to do until my stuff was ready. It was my brother’s (almost 4 years older than me). Of course, I started whining, saying I couldn’t wear that. She told me to just tuck it into my pants and to stop being a sissy (!) Ah well….
I was just in my tighty-whities, and flung the shirt over my head and was enveloped in this, to me, huge tent. But as I bent over to pick up my pants from the bed, I glanced over at the mirror. It was only fleeting, but what met my eyes looked like this young girl in a voluminous dress which came down to her mid-thighs.
Mm. I closed the bedroom door. My Mum knew about kids my age and that we want a semblance of privacy, so I knew I wouldn’t be disturbed without a first timid knock on the door. I returned to the mirror for a closer look. Yeah – nice. I brought my hands to my waist and held the shirt in at my middle, which made it flair out a bit at the bottom. Yes and more yes, thought the figure in the mirror, adopting a coy pose by bending one knee slightly and turning sideways-on and looking over her shoulder.
So what else could I do to improve my new look? Well, my hair was relatively shaggy and longish, so with my fingers I gave myself a centre parting and the hair hanging down at the back I brought it round until it was in front of my ears. Wowsy. What next? It still looked like a T-shirt – at least it did until I folded the short sleeves in on themselves, baring my shoulders.
Now all girls have a bosom, even if only a small one. I knew I needed something to pull off the look, but remember I was just a boy with no access to those gorgeous things I now know were just around the corner in my Mum’s bedroom drawer. So – socks, of course. Fold one into there, and one into there….they dropped out. Oh. So a belt (also black, of course, I thought with my budding sense of fashion). One sock in, two in…they dropped to my waist and suddenly I resembled a granny without a bra – ugh!
My next brainwave was to approximate a bra, so I took off the T-shirt and pulled on a sleeveless vest which I rolled up above my midriff then re-inserted the socks. They stayed where they were. Then T-shirt, belt, re-adjust hair, and – wow! Then I heard someone coming up the stairs and it was all off in a flash….. to be repeated.
- 16 Oct, 2024
- 15 likes
General information only. Disclaimer.
Enjoyed this blog?
Discover more member-written stories, tips, and crossdressing dating insights from our community.
ClubCrossDressing ®


























Versatility and the ability to adapt with a creative mind. xx
Fun Fun Fun all the way Charlene....luvvit xxx
SOO similar to my first encounter with my “up til then unknown” feminine side- I used socks initially and then graduated to bunching up two soft knit caps into “boobs” and then- eventually was overwhelmed with temptation of taking an old bra my mother had tossed into the waste can- it was my task to empty all the room waste cans each week for garbage pickup- I snuck it and hid it and soon “graduated” to filling balloons with water and VOÍLA- it was as close as a young boy might come to actually “feeling I had realistic breasts” - they were close to what my young mind could imagine real breasts felt like and the jiggled and - if I set the balloons “just so” in “my bra”- I could make the “fill opening” that was tied off look like nipples- I was “off on my life’s adventure”.
Thank you my darling Charlene for helping me take that trip back down memory lane