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    My journey to becoming a crossdresser

    I have been asked a number of times by friends on this site about my journey to where I am today, a chap who loves crossdressing and everything associated with it.  I have always replied individually but today I thought that I would share my journey more widely.

    When I was a schoolboy I first started wearing ladies undies, in those days typically roll on corsets and stockings which I " borrowed" from my older sister, I gradually built up a small wardrobe of lingerie either from my sister or female cousins. Whenever I dressed up in lingerie I felt really excited especially when wearing stockings, sliding stockings over my legs and clipping on suspenders drove me wild and had me moaning out aloud in pleasure, that has not changed to this day. At about this time a friend who was to later become gay and live life as such openly, gave me a hand job while I was looking at "dirty pictures" in a man's magazine, looking back I realise it was one of the best I ever had. But, at the time I would have regarded myself as straight.

    My teenage years were  "normal" enough and I had many girlfriends  but there was just one occasion when we went to a dance at the local hospital and I "fell in love" with one nurse who I danced with most of the evening until I discovered she was a he, oh how the lads laughed!

    I married in my mid twenties and had three children but the marriage wasn't to last as my wife turned out to be a binge alcoholic with schizoid tendencies, life really was traumatic and highly dangerous in those days. As my marriage was breaking up I met at work "H" who was eventually to become my second wife. "H" was ten years older than me but had more energy and drive than my first wife had ever add. "H" and I moved in together in the early 90s and for many years after enjoyed a phenomenal sex life both here and in France where we lived for a number of years. In those early years I had a job where I had to travel round the world a lot and often "H" would meet me at Heathrow when I returned from a trip. The first time "H" met me was in winter and there she was looking super in a long camel coat which when we got to a quieter part of the concourse she opened to reveal she was only wearing stockings, suspenders and the flimsiest of bras. Thereafter whenever the weather dictated wearing a coat "H" would turn up so dressed.

    Gradually however our relationship changed, I began to build up in secret a new wardrobe of ladies clothes and I encouraged "H" to use strap ons on me which I soon found I loved, also I gradually persuaded "H" to let me take her analy which I also loved. At no point in this process did I think about my sexuality I just thought "I'm loving this". Gradually things slowed down sexually and we went through a period where we did not have sex in any form, for my part I kept myself amused buying, wearing and posing in lingerie in secret and developing a taste for cum (my own), I assumed wrongly that "H" had just gone off sex BUT one day when I could not live with the secrecy any longer I told "H" only to find that she had figured it out but also that she had found her lesbian feelings reawakened and started a friendship with a dear friend of ours Caroline. After this there was a brief halcyon period where every so often "H" and I would make love but with me fully "dressed", I loved it.

    "H" and I still live together very happily, I dress, pose, take pictures and make little trips out whilst dressed, "H" sees Caroline from time to time. Should one day I be single again I long to establish a relationship with a gurl and fulfill all of my dreams.

     
      Posted on : Dec 16, 2022
     

     
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