My trip down Crossdressing’s Rocky Road

I wanted share my storyn  Some of what is to follow might be upsetting but there is a happy ending …

I was born August, 1970 in Manchester, England to older parents. I was an only child, had half-brothers and sisters from my parent’s previous marriages, but they didn’t live with us as they were much older. My father ran his own business. I was brought up in an affluent part of Cheshire called Hale. The area was nice, but it was a lonely as I had no siblings around and only a few friends.

My mother had a violent temper, brought on because my father was a womanizer who stayed out until the early hours of the morning. I was subjected to their reoccurring arguments. I went to school with bags under my eyes over the lack of sleep and the worry it caused me. My mother was not maternal by any means.  I had to make my own breakfast and cross three busy main roads at the age of six. It was a tough life, even though I lived in a nice area. At times, my mother would totally lose it and beat me with a high heel shoe or anything else she could get her hands on. I continued to show her love and affection in return.  I didn’t know any better.

My parents split up in the early 1980’s after he told her that he didn’t love her any more (I don’t think he ever did.) The feelings of emptiness and rejection grew stronger inside me. I couldn’t escape the thoughts of why this was happening.

My mother and I lived in Altrincham, Cheshire for a few years, where things calmed down. She met a man who lived some distance away in Bolton, Lancashire. Eventually, we moved there and I had to start at another school. I found it hard to mix with the others because of joining half-way through the third year and because I spoke differently as I didn’t have a Lancashire accent.

It was during this time I began to wear women’s clothing. I tried on a pair of my mother’s panties, but I didn’t fully understand what I was doing and why it felt good. With the supply of available clothes very limited, I didn’t often get the opportunity wear girls clothes. After my mother broke up with the man from Bolton, I once more found myself moving, this time to Great Sankey in Warrington, Cheshire. It also meant another school. I attended three different secondary schools, and because of our moving, my education was inconsistent and difficult. This is where my story becomes interesting…….

After moving to Great Sankey in Warrington, we lived in a row of four terraced houses. Living next door to us was a very beautiful woman and lovely man, both of whom I got to know very well. I was 15 at the time, and my feelings of wanting to be a part-time female were getting stronger. It was made worse by the beautiful woman next door, who happened to be from Finland. I had no female clothing I could wear; my mother’s knickers were too big for me. I couldn’t buy them from the shops without money or courage. I had to do something. I have never done it since, and I regret doing it, but I took something off a washing line! It was the woman’s underskirt from next door, and I cherished it for many years to follow. Her husband came round and informed us that his wife was missing some clothes off the washing line, (I only took one.) My mother found it quite amusing that there was a knicker-pincher about. I kept quiet because the humiliation would have been worse than the confession.

Over the next several years, I managed to scrape together a few items of female clothing to wear every now and then. I frequently wore the underskirt in bed.  It just felt so silky and the fact it had belonged to such a pretty woman made it that much better. I believe that my mother never knew about my crossdressing. She passed four years ago, and I am not aware that she had any idea.

By the time I was 30, my crossdressing had really taken hold of me. I moved out on my own and met a nice woman who is now my wife. When we first met, I didn’t confide in her about my crossdressing.  It’s not really a normal topic of conversation, is it? Trying to find time for crossdressing became difficult because she had two young sons at the time who needed lots of care and attention. I was restricted to wearing women’s clothing only at night and hidden under my pajamas. As time went by, my frustrations built up because of my desire to be female. I was supposed to be the man, responsible for holding everything together in the family. The boys grew up and became independent teenagers. I had time to spend on my own, upstairs in the bedroom, where I could dress up and be reasonably safe from being caught. My female clothes were still very basic. I was getting bored of them, as you might imagine, wearing the same ones for years.

It happened five months ago, as I felt I couldn’t keep holding back the stress of keeping my secret. The deceit, the hiding, the wanting, the needing, all became too much for me so I confessed to my wife. I told her what had been going on all these years and what my feelings were. Surprisingly, she wasn’t the least bit amazed, saying that she’d suspected something. It had been the little things, various items of her clothing being moved or missing altogether.

My story, as it stands now, isn’t perfect but it is a start. My wife now knows and she is reasonably agreeable for me to pursue my interests, within reason. She’s not willing for it to become an obsession but she is happy to interact with me every so often. I tend to model myself more as a girl at age 16 rather than a woman my age. I have a superb wardrobe with lots of pretty clothes – short skirts, tights, jumpers, leggings, pajamas, etc., all the things I could only dream of having a few years ago. I’m currently experimenting with make-up (with varying degrees of success.) I have three beautiful, long blonde wigs that I cherish and properly look after.

My road into crossdressing has been a rocky one. It had been mostly done in secret and in fear of being caught, up to recently opening up about my feelings and sharing them with my partner. There is still much to be done. I need to show my wife that I still love and cherish her, as I did when we first met. For me, the biggest lesson I’ve learned has been to stop selfishly thinking of only myself. My wife and kids come first and they always will. Whether Fiona continues to be as free as she is now or is once again constrained, I am and always will be a crossdresser for life.

More Articles by Fiona-Ann Moss

• Good to Be Back!
• Feeling like a caged animal…
• CDH. A testimonial from Fiona Moss.
• What Makes Fiona Tick?

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and articles from Crossdresser Heaven.

SUBSCRIBE!

You have Successfully Subscribed!

We hate spam too, unsubscribe at any time.