My History

Holly Marie September 9, 2022 Crossdressing Success Stories 28

I was quite young when I noticed my sister’s underwear in the laundry basket; I was curious more than anything and didn’t really feel any need to explore further. Gradually, the idea of seeing what those strange items felt like took over. Eventually, I had no choice but to go into her room and steal a pair of her panties and whisk them away to the bathroom (the only door with a lock!)

They felt so soft as I slid them up my legs. They looked a little strange (what with there being a bump); it was weird – though an incredibly beautiful experience feeling them on. For a few years, I kept trying on panties but nothing beyond that. The feeling kept growing, there had to be something more. One day, I saw a teacher at school wearing tights… Frankly, I’ve never known such an immediate attraction. I just had to head back into my sister’s cupboard and “rescue” a pair. IMMEDIATELY HOOKED!

By now, I was savvy enough to never let my school friends know what I was doing, but every so often, I would borrow a pair of tights and wear them under my school uniform. I was nearly caught once but managed to take them off in the toilets and avoid being found out. For many years, I could do little else; I had neither the money nor the opportunity to buy anything beyond the occasional pair of tights, and I was more than happy enough with the situation anyway.

And then… I noticed this lady wearing a pair of black, not very high, heels; quite why, they fascinated me. The feelings that tights had given me seemed to well up to the surface, and while I didn’t really have any chance of buying any shoes, another layer to my complex personality was definitely established.

I came late to the internet age, and I really didn’t want a credit card either – not until I suddenly realised the possibilities. One night, when my wife had gone out for the evening, I drank a little too much wine and settled down in front of her computer with my credit card… The wine persuaded me to look at some sites of interest. Shortly, I was looking at a cute, sparkly black miniskirt and a pair of high-heeled knee-length boots. How could I possibly do this? Wouldn’t my wife intercept them being delivered and divorce me on the spot? Surely, the entire world would immediately know what I was doing.

I very nearly chickened out, but another glass of wine and I hit the send button. PANIC! What have I done? There followed five days of sheer terror when I didn’t dare to leave the house in case they delivered my parcel and my wife saw it – but then on Saturday morning… The postman calls as usual – and he has a package for me. THIS HAS GOT TO BE IT! I immediately took the parcel upstairs and hid it in the back of the cupboard. My wife will be out tonight. A bath and a shave later, I open the package; STREWTH! So beautiful…

I’d already selected a pair of sheer black tights and some black lacy panties; this is going to be awesome… The strange thing was that there was no physical reaction, just a feeling of calm and serenity; it felt so right, and I loved prancing up and down in front of the bedroom mirror, admiring how my new clothes suited me. Having gotten away with it, I ordered some tops and wigs and got up the courage to buy more underwear at the self-checkout at my local supermarket.

When I was finally able to select a full outfit for myself, I felt better than I ever had; the feeling was ecstatic, though I knew that the next big step was still in front of me. I found a local “Chameleons” group on the internet; would I have the guts to be dressed in front of other people – even though I knew they would be dressed up, too? Only one way to find out… I nearly backed out, but eventually got there and into my outfit in the changing room. My heart is beating three times a second and my palms are sweaty; I finally forced myself… and found that very few of the other ladies there were dressed in anything even remotely feminine… but on the other hand, they all seemed very friendly, and no-one cared that I was dressed up like… well, I don’t really want to say – let’s just say that it wasn’t conservative.

After a few meetings, I decided the Chameleons wasn’t for me – they mostly wanted to be full-time while I was very firmly a man who loved dressing up. It was obvious there was a new step I needed to take, and one chilly night in February, I managed it. Everyone in my house was used to me heading downstairs and watching the television at strange, early hours; this night, however, I screwed up every ounce of courage I could muster, pulled on my cutest outfit, and headed outside.

The streetlights seemed particularly bright, the sound of my heels on the pavement especially loud. I was hoping no one was awake at this unearthly hour. I walked over the road and down the alley. Turn right at the top, onto the side road, then right onto the main road. A taxi pulls up beside me at the corner – PANIC! He has two drunken girls in the back coming back from a night out, but no one notices me, or at least, they don’t realise anything is out of the ordinary, even though I’m at least ten inches taller than any girl they’ve ever seen thanks to these gorgeous high-heeled, platform boots.

The taxi moves off and I breathe again. I’m off past the shops and turn back towards home. A few windows are lit up, and some curtains flap a little, but there’s no indication anyone has seen anything out of the ordinary. Much as I’d loved dressing up, it’s a relief to take my outfit off. THE STRESS! Ever since, I’ve been getting up the courage to go out in the daylight and get a proper, professional makeover and photoshoot.

Hopefully, you ladies out there will get to see the results before long. It’s been a long, long journey, but this is where I am. I feel with every distinct step, I’ve grown. I don’t want the world to know (beyond suspicions) but I’m proud of myself for having the guts to get here. As a man in a skirt, I feel far more complete and at ease with myself than I ever could have if I had denied my curiosity all those years ago. It makes me wonder; do all boys experience the same feelings and curiosity that I did? Are there far, far more crossdressers out there than even we realise? Will society ever evolve enough to fully accept the idea of crossdressing? We can but hope…

Thank you for taking the time to read my story; please keep an eye out for my photoshoot pictures when they come up – if I can steel myself to have them taken.

Ladies: I love you ALL…

Holly.