Cross Dressing Tales from my Past

Early Days

My first recollections of cross dressing were when I was about five or six years old. For some reason, my Mum used to keep her stockings under a cushion in the living room. I remember taking the stockings from their hiding place and pulling them on. I even remember Mum coming in while I was doing it once. But the thrill I got from doing it was intense and it's a thrill I still get from pulling on some fully fashioned stockings, just the same now as it was then, nearly sixty years ago!  

I remember when I was still

about seven or eight, my older sister and I went to stay with our grandma for a few days. On this particular occasion I recall seeing my sister and grandma in the garden so I crept into her bedroom and put on a pair of her knickers and a suspender belt that was also in the drawer. I remember to this day the wonderful feeling it gave me and although on that occasion I didn't put on any stockings, It wasn't long before I started wearing her bra, knickers and suspenders and stockings and then skirts and dresses. It marked the start of a lifetime of cross dressing in her clothes.  

During my early years, I took very opportunity to wear my sisters clothes that I could. Whenever there were dressing up games I would always end up, by my design of course, wearing a dress and her shoes and socks and even remember on one occasion being left with a dress on that I couldn't get undone. She left me indoors to go outside and play. I ended up going out in the garden too to get my her to undo the dress in front of my Mum. It was all innocent fun then, or so my Mum thought? Soon I was taking every chance I could to wear her underwear and dresses, meticulously replacing every item when time came to put it back. Wearing her clothes never lost its appeal.

As a young child, probably like most of us, I went to play from time to time with the girl next door. This girl, whom we

shall call Lynn because that's what her name was, was for a time my best friend. I remember on one occasion going round to her house and we decided - I can't exactly recall who's idea it was but one can only speculate - we decided to swap clothes. I wore her dress and shoes and she wore my clothes. Great fun you can imagine especially as Lynn wanted us to go and show her mum whom I can remember to this day was very clearly less than impressed. I feel should would have been impressed even less had she realised I was wearing her daughters knickers and petticoat as well. Ah, those were the days.

In my early teens I seem to remember taking very opportunity I could to wear my sisters underwear and dresses. My Dad played cricket and the rest of the family would go off with him for a few hours on a Saturday, leaving me alone at home. I'd lock all the doors and dress up in bra, knickers, suspender belt and stockings and a dress and my

sisters shoes, at that time I could still get in to them. I started using makeup, a liquid foundation of my mums, blue eye shadow and lipstick but of course no wig at this time. My afternoons were a time of changing into a different dress or skirt every ten minutes or so and parading myself in front of a full length mirror. When the time came to put it all back, I'd systematically replace everything exactly in its original place, double checking to avoid being found out. I had a few close shaves but probably remained undetected. My sister probably knows that her clothes were moved but we've never talked about it.



In my early teens, as I mentioned before, I found any opportunity I could to dress in girls clothes. Going to an all boys school that I did, when it came to school plays, naturally the female parts were played by boys too. I'd had my eye on one of the girls parts in an up and coming play but was devastated when I had to go for a dental appointment on the day of the auditions. Of course I missed the female roles (which incidentally were hotly contested) and ended up with an unexciting male role. My devastation was further compounded by having to watch two other boys dress up for rehearsals and the four nights of the play in bras, tights, dresses, shoes and makeup to perform in front of the watching parents. The idea of dressing convincingly as a girl or a woman and parading on stage is a thought that haunted me for a long time and I've hated dentists since then too.

Teens and Beyond

In my early teens, as I mentioned before, I found any opportunity I could to dress in girls clothes. Going to an all boys school that I did, when it came to school plays, naturally the female parts were played by boys too. I'd had my eye on one of the girls parts in an up and coming play but was devastated when I had to go for a dental appointment on the day of the auditions. Of course I missed the female roles (which incidentally were hotly contested) and ended up with an unexciting male role. My devastation was further compounded by having to watch two other boys dress up for rehearsals and the four nights of the play in bras, tights, dresses, shoes and makeup to perform in front of the watching parents. The idea of dressing convincingly as a girl or a woman and parading on stage is a thought that haunted me for a long time and I've hated dentists since then too! This photo is from 2010.

Soon after going to secondary school I joined the photographic club and soon after that I spent my hard won savings on my own photographic darkroom. Needless to say it wasn't long after that, probably at about the age of thirteen I started taking photographs of myself in my sisters clothes. At first I took the what now seems like an idiotic decision of getting my friend to press the shutter while I was wearing her underwear and a dress, with eye shadow mascara and red lipstick. (As it happens, he didn't seem to mind and actually thought it was great fun). I then discovered the extended cable release and was able to start photographing myself in her underwear, suspenders and stockings. I built up quite a little album of photos - still no wig at this time so mainly in hats and headscarves. So, a lifetimes obsession (and I use the word lightly) of photos of me dressed started. I don't know what happened to the pictures and I lost touch with my accomplice - perhaps he might even be looking at these pages now? 


In my middle teens two significant events happened. The first was that my grandmother came to live with us. This had a serious effect on my cross dressing because now I had very little time on my own in the house. Not that this stopped me, but it did make life considerably more difficult. Fortunately she couldn't negotiate the stairs so I was resigned to having to take clothes up into the attic to wear them out of her way. I managed but I certainly couldn't indulge myself like I had before. The second thing was that I found a letter in a woman's magazine with a response by the infamous Marjorie Proops. (UK 's first real agony aunt). The response of course, went on to describe the writers husband as being a transvestite. WOW. What I did had a name! and not a very nice one at that, and there were other people doing what I was doing too!! I think it was turning point for me from doing something because it was fun to do into doing something that I couldn't stop or control. I was shocked for some time to follow, but it never stopped me, as if anything could.

As a growing cross dresser, the words "Fancy Dress Party" always conjured up an opportunity to wear a dress. That, coupled with my skill of inducing friends to persuade me to go dressed as a girl provided my only outlet for seriously taking my hobby outside the house. One such an occasion was a youth club fancy dress party when a female friend persuaded me to go as a girl. Resisting for at least five seconds it involved going to her house and trying on various dresses - with bra of course, stuffed with socks - tights, shoes and a blond wig duly encouraged by her and her sister. Having chosen a suitable dress and shoes and taken them home with me for the big day, of course I had to try them on at least three or four times just to make sure they were suitable! The fancy dress party turned out to be a great success made easier by other boys dressed as girls too. It was my first opportunity to spend an evening in a dress and wig but of course my attention to detail in wanting to look like a real girl rather than a parody of femininity that the other boys did, did not go unnoticed The picture is one from my archives, scanned from a colour negative. The skirt was a favourite pleated skirt long since departed but I'm just shocked to realise I still have the scarf.



Later on my school life another dressing up opportunity came along. I knew it would and it was one I was looking forward to. At Christmas each year, the senior boys served Christmas Dinner to the first year boys in fancy dress and for sometime before the event I'd decided that I would go dressed as a schoolgirl. I broached the subject with my Mum, who looked out my sisters old school skirt, a pair of her sling backed shoes and some black opaque stockings and suspenders. (Of course I knew where they all were but she thought she was finding them!) I used my own white shirt and tie but wore a bra stuffed with socks too. I actually had a dress rehearsal in front of my mum - the only time she's seen me in a skirt - before the day of the lunch. I had a wonderful time with my skirt hitched up to reveal my stocking tops in true St Trinians style and remember keeping it all on - as did the other boys in their fancy dress - for a couple of hours afterwards. A memorable day and I still love my school girl uniform to this day.