A cross-dresser’s story – The beginning

Since I started to wear retro and vintage foundations and stockings, I have met, spoken to and admired many cross-dressers. I have a fondness of genetic men who choose to wear what is considered to be women’s clothing, and greatly admire their style. More often than not, they share my taste in underwear, and choose to wear firm, structured foundations, as well as fully-fashioned stockings and RHTs.

I have seen a lot of hostility towards cross-dressers over the past few years, and as a consequence, I have become very protective of those genetic males who choose to style themselves in a feminine manner. It’s also very important to me that it is understood The Nylon Swish is very much an inclusive blog where everyone is welcome. 

As such, I asked Rachael to write a series of blog posts for me, covering a number of topics. I hope that you enjoy her insights. Please feel free to leave her friendly comments, letting her know how DAMN HOT she looks in her beautiful underwear!! 


I have been asked by Elinor if I would consider putting down in words some thoughts and details of my journey through life as a Cross-dresser.  I am very happy to do so and hope you enjoy my musings below.

The obvious place for me to start this blog is right at the beginning of my long road to thoroughly embracing Cross-dressing – Male to Female.


For me, now aged 63, it all started over 50 years ago, in the 1950’s when I was about 4 years old.  For some reason, I could not fathom at the time, I was deeply attracted to my Mothers’ underwear, especially her open girdles.

I cannot recall whether, because of this obvious interest, I asked her, or she offered me, one of her cast off girdles but I do recall treasuring it and wearing it as often as I possibly could.  I even wore it when we had visitors!  I must presume that then, it was firmly believed that everyone thought ‘Ah, bless him, he’ll grow out of it!’  Or at least they hoped I would as I am sure transvestism would not have been as openly accepted as it is nowadays.

I probably had that girdle for about 2 years and when we moved house, it disappeared and I never saw it again.  I cannot remember if it really bothered me or not and I certainly never received another from my mother to replace it.  If memory serves correctly, it had a satin front panel and four suspenders/garters although at the time I wasn’t at all sure what they were for lol.  Nor would it have been possible for me to wear stockings with it, as at age 4 my little legs would clearly have been way too small.

For some years after moving house I cannot recall even thinking about wearing another girdle and it was probably not until my early teens that I began sneaking into my Mothers lingerie drawer and occasionally putting one on.  She even had a rubber girdle which had a divine odour to it.  (This is all making me very jealous! – Elinor)


As I grew taller I also ventured into the wearing of her stockings with a girdle and recall how wonderful it all felt.

As much as I enjoyed these feelings, and yes, a lot of it at the time was sexual arousal however, I did also feel disgusted with myself!  Not because I may have been violating my mothers’ privacy, that thought never occurred to me until much later in life, but because it could not have been ‘normal’ for a rugged sport playing young teen to be wearing feminine clothing.  Especially as I was really attracted to girls.

Ultimately, I would dress fully in my mothers’ clothing, girdle, stockings, heels, skirt and blouse, even tried one of her bras.  Although it felt so good, I guess I had been programmed by society at that time, that I was a deviant! It took many years for that feeling and those thoughts to fade.  After all, It was the 60’s and I had started hearing of homosexuals and the labels society was putting on them:  ‘Queers’, ‘poofs’ etc. but I knew I did not fall into that category, I only liked females.  Yes, I had a few close male friends but my physical interest was totally in the direction of the feminine, and they remain so to this day.  I am most certainly not gay, nor am I bi-curious.

During my dating years, I didn’t ‘dress’ at all and didn’t start again until I was married and began buying my then wife nice underwear, most of which she flatly refused to wear.  But that didn’t matter, at the time we were the same size and I could do, so I did, lots.

I didn’t start building my own feminine wardrobe until after my divorce and I was settled in my own home and wow, has the size of that wardrobe grown!  I now own decidedly more feminine clothing than I do male.  However, I do not subscribe to the notion that I wear women’s clothes, I bought all of them so that makes them MY clothes.  Yes, they are feminine by design but they are mine.

I have of course now ventured into make-up and occasionally going out and about.  I have been to dressing services on three occasions and thoroughly enjoyed my time there.  I have been to Susie Adams of Chateau Femme in Bournemouth on two occasions and Lizzy Hants in Southampton once.  I have picked up make-up tips from both and am sure I will visit with them again in the future.


I am now totally at ease with who and what I am.  I am a male to female cross-dresser who loves to spend time trying my best to appear as a woman and strive to be as presentable and passable as I can. Why do I dress is probably a question many of you would ask of both me, and perhaps yourselves and I can only say that I feel a very deep NEED to.  I need to express what is clearly a very strong feminine side to my make up as a human being.  I also believe that it is what makes me the ‘Complete’ person that I am.  I do know that if Rachael was not a part of my life, I would not be ‘Me.’

It has been a long road, with many bumps but I would not change it for anything.  I love Rachael deeply and have made many, many TGirl friends, through the internet along the way, socialising with some too.


10 thoughts on “A cross-dresser’s story – The beginning

  1. Thanks Rachael for sharing your story and thanks to Elinor for providing the forum and being so supportive of us guys who enjoy dressing in a “feminine manner”. Gender identity and gender expression are artificial constructs that really don’t have much to do with how your body is put together.

  2. Thank you for sharing, and thank you for letting her use your blog to share her story. I’m a fan of your blog because I love women in vintage underwear, but also as a cross dresser who enjoys wearing it and thinks it’s beautiful too. Thank you for being open minded and inclusive!

  3. “Although it felt so good, I guess I had been programmed by society at that time, that I was a deviant! It took many years for that feeling and those thoughts to fade.” Truer words never spoken. I know completely how you felt but we both found better places. Great read.

  4. For reasons unknown, my original comment disappeared 🙁, but such is life.

    Rachael – you look sensational! The parallels between us are rather striking. Mum was a girdle wearer, even though at 5’11 and 7 1/2 stone (105 pounds) she didn’t really need one! I first dressed to any serious degree at 12 – I think she knew but never said anything. Since then, it’s come and gone periodically until about four years ago when I realised that it needed to be let out from time to time. To this day, I’m a wearer of what I call “traditional” shapewear like girdles and corselettes – to me, my shapewear shouldn’t and needn’t be something I’d be ashamed or embarrassed to be seen in.

  5. Pingback: A cross-dressers story – Getting to know Rachael | The Nylon Swish

  6. That’s a great story Rachael and one that mirrors my own in terms of a fascination at an early age with my mothers lingerie draw. Its lovely to be able to read and comment on such stories in a safe and friendly environment so my gratitude goes out to you too Elinor.

  7. Pingback: A cross-dresser’s story – Rachael’s wardrobe | The Nylon Swish

  8. Wow sounds a bit like me. I got started with panty’s though and still wear them most the time. I don’t show off in my lingerie except on a very rare occasion. Although I have a few corsets I rarely wear one. Reason? The stretchy ones are to stretchy and I can’t lace a lace up one well by myself. Same thoughts on the style it may be girls/womens/ladies, but it’s my underware and I have paid for all of it ! Thanks Elinor and Rachael !!

  9. Pingback: The Nylon Swish

  10. Great article I don’t know how I missed this. Being a crossdresser Ian relate to everything said. I also started young at age 12 using my sisters clothes, she eventually figured it out and was supportive of my dressing and shared many things with me and taught me all my make up skills, I purged many times going thru high school and college but couldn’t shake my desire for femine clothing, thankfully I married an understanding woman who has supported my dressing for 50 years. When I retired we agreed I would dress full time unless I needed to appear as a male at some gathering, this has been the most exhilarating time in my life and I am so happy I found this blog and post. I am a huge lover of retro lingerie and garter stockings.
    Best regards Rhonda Whilling

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