The Crossdressing Journey

The crossdressing journey is probably similar for all of us. It can be quite harrowing in the beginning and develop into a wonderful thing as we grow in confidence and are prepared to face the world without fear.

I compare my journey to a long bus ride which has a number of stops.

The first stop is quite complex. We all realize that we are crossdressers at different stages of our lives. In my case, I put on female clothing at 12 years old. I felt a tremendous guilt as a result of this excursion, and my parents could have found out very easily, but luckily didn’t, This was of course a great relief to me. One must understand, at that time, mid-1940s, I would have been put in some kind of treatment facility or youth correction centre. Homosexuality was an actual crime; as was wearing clothes of the opposite sex. While they are not the same thing they both would have been considered serious moral crimes against the state.

Obviously it is not the same for all crossdressers as we each have our different starting points.

My personal journey, my desire to dress, was suppressed for many many years. Morality of the era, Naval boarding school, fourteen years in the Navy proper and fifty years of marriage to the mother of my children. My wife died in 2009 and a few years prior to that happening my urge to crossdress came back. I would spend time on websites with crossdressing themes and dress in secret. My wife’s death released me and my journey began in earnest.

The First Bus Stop: Home alone

Dressing at home with this fear of going out in public dressed in female clothing. On-line shopping was in its infancy, so the main source of clothing was that of my deceased wife. Fortunately it fitted quite well. I would also shop for clothes, and if challenged in some way would make it appear as if I was gift shopping. This was particularly easy for jewelry and items of clothing such as dresses. So here I am, dressing as often as possible with nowhere to go and no one to see me. What to do about it?

The Second Bus Stop: Hello World

The internet? Toronto is a big city so there must be some crossdressing activity; and there is. There is a fairly well established organization called Xpressions. Besides many other functions such as monthly dinners, Xpressions holds a Pub Night once a month in a regular pub, and an annual gala. To encourage newbies, one is allowed to attend Pub Nights dressed in drab. I don’t think I need to explain this term. Also, the event takes place on the second floor so, it is not too exposed to the general public. Food and drinks are both served at cost. It happens that the pub is situated close to Church Street, which is known as the Gay Village. It is also very close to a subway station, and has a parking lot close by; it is very convenient. Finally, one works up enough courage to attend one evening, even though one goes to the event dressed as one would going to work. Nerves are on edge and I was an absolute mess. Guess what happens? You bump into a lot of nice people. Some en-femme and a lot dressed in drab; it was a work day after all. One can’t say normal street clothes because dressing en-femme to a trans-gender person is normal street clothes. You have a couple of drinks and some food and you wonder what all the fuss was about. The President comes over to talk to you and you find out more about the organization and others come by and welcome you. After a couple of hours you go home feeling that you have made a lot of new friends, which you have, and you feel much less guilty about your crossdressing, as you are not alone.

The Third Bus Stop: Feeling One’s Way

One continues to to attend the occasional Pub Night, and with each visit gain more confidence about being dressed and what it entails. As yet I haven’t ventured out dressed in female clothing.

During one Pub Night a fellow attendee sat with me. You find that you have quite a lot in common; we are about the same age and she lives quite close to me. I had come in by train, but she offers to drive me to my car at the G.O. station, which is just off the highway on her way home.. This enables more conversation in the car and eventually I get to my car and she goes home. When we part I am grateful for the interaction and just expecting to possibly meet again at the next Pub Night.

The following Saturday morning I get a call from my new friend telling me to be dressed ready to go out at 6:00 p.m. She and two other girls are going to pick me up and take me to dinner. Wow! The blood pressure goes sky high and you start to seriously wonder how you will handle it. You ask them to park their car across the bottom of my driveway so that not too many of my neighbors will be able to see me go out dressed. When the car arrives out I go. If I ever really wanted to know what self consciousness is, I found out that night. We drove to a restaurant in a nearby town and I thought every one in the world was looking at me all the time; even in the car in the dark. What an experience that turned out to be. That was my first venture out of the house dressed en-femme and the beginning of my real adventures as a crossdresser.

The Fourth Bus Stop: Getting Venturesome

I started to drive to Toronto to attend the Pub Nights instead of going by train. Now I am going dressed en-femme. It is still a struggle, but I bite my tongue and live with it. I find out that there is yet another girl who lives quite close, so we share rides. To get to downtown Toronto at seven in the evening takes about two hours due to traffic volume. So we have to be on the road by 5:00 p.m. Obviously coming home it is not so congested. Unless they are doing repairs to the elevated highway.

Confidence is increasing. Not only do I attend pub nights, but I also go to the monthly dinners. These are held in restaurants situated in different locations around the Greater Toronto Area so that they are convenient to everyone. I am now in the outside world dressed quite often and my personal confidence is increasing in leaps and bounds.

The Fifth Bus Stop: Out and About

The next is the stop where one goes out in public on one’s own, or if in company when one is just with friends. It was about this time that I met my now wife Gail. She was a terrific help with my makeup and clothes selection which also did a great deal for my confidence.

I have to mention Xpressions’ annual Christmas gala. Gail took me to a used clothing store to buy an evening gown. I already had dress sandals to go with it. During the evening we volunteered me for the Xpressions Queen for the year contest. Surprise, surprise, I won it; so I had the crown for the year. Unfortunately the crown was mis-placed , which is another quite amusing story. My goodness, I couldn’t get over it. Seventy year old me, Queen of the Ball?

Now I am going out dressed on my own. I go out dressed to the movies, I go out to dinner or in the summer I just go out. Usually with Gail, my neighbor, or friends. We live in a very close community. It is semi-gated and most of the residents now know I dress. I even go to the Friday night dances dressed.

I also have a fairly close friend who was living in a townhouse complex and felt quite uncomfortable with it for several quite valid reasons. She moved to an apartment in a different town, and is now living quite happily on her own away from the problems she was experiencing. She also joined a church congregation which actually encouraged her crossdressing. So at 8-years-old she is perfectly happy living her life en-femme

I must be perfectly honest, there are occasions when I still feel a little uncomfortable. I don’t know if it will ever go away completely.

The Sixth and Final Stop: Transition

A few girls have this inner desire to become as female as they possibly can. This usually entails surgery. Changes with the jaw arrangement to soften features and surgery to the male anatomy. To do this one must have a lot of courage and a deep sense of femininity to undergo this painful and serious process. Once done it is irreversible. Taking this step is not for everyone. The factors which have prevented me from taking this step are — my age, the cost and the fact that there is another person in my life who is equally in love with my male persona, Paul. Kudos, to all the girls who go through this serious event. I sincerely hope that they each become exactly who they really are and want to be.

Live your best life: Be your true self.

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Tags: crossdressing, featured, opinion

Category: Transgender Body & Soul