Early Days Out and About

I provide here for you a review of my early experiences that may be helpful to my sisters in this group.

It has been several decades since I first ventured outdoors while dressed. In those days, I went by the name Jill, mostly due to the character Jill in Charlie’s Angels, although I actually wanted to look more like Kate Jackson.

My first experience with crossdressing happened trying on my sister’s dress when I was eleven. I don’t know what possessed me to do it, however, I knew I wanted to. Even though it was very risky, what with my family being on the main floor of the house and me being upstairs in my sister’s bedroom, I couldn’t resist. I don’t recall if I took any of my clothes off, but I do remember that feeling when I pulled her dress over my head. Once I had it settled in place, I just stood there, looking down at myself and feeling a great sense of relief.

I next remember wanting to crossdress in my mid-twenties, during my early years in Canada. There was an ad on the Telly at the time for Aviance Perfume. The jingle was something about no matter what kind of a day you have had, it’s going to be an Aviance Night. The video was of a young woman slogging away in the office, then during her Aviance Night, she wore a black dress and looked stunning. Every time I saw that ad, I wanted to be able to do that. After a stressful day at work come home, shower, and once suitably attired have my “Aviance Night.” This was about the time when Charlie’s Angels first appeared on the Gogglebox, and Kate Jackson was making a big impression on me. I in part wanted to date her and to look and dress like her. From what I have gathered, many other crossdressers have experienced similar feelings.

Actually, now as I think of it, it may have been before the show first appeared on television that I started to think of myself as Jill. I do remember that in the early months of 1976, I planned a road trip from Alberta down to Southern Ontario. It occurred to me that I should let my hair grow to shoulder length, have it styled in a very obvious feminine way, purchase some suitable clothing, and make the journey as Jill. In my thoughts, I would introduce myself as Jill whenever the occasion presented itself. However, the mid-seventies, although wonderful years, were not like the times we are living in now. I didn’t know how to go about buying suitable women’s clothing, or how I would get away with wearing my hair in a feminine style in the environment I worked in, let alone explaining it to my friends. So then, I went on the road trip as my usual self.  I still thought about the idea of being Jill though, driving my 1970 Dodge Challenger wearing a miniskirt, strappy sandals, and a halter top, my hair shoulder length and wavy.

Some years later, when I was back in England, I remember coming across a short black skirt somewhere and then keeping it in the closet. When the urge came over me, usually when I was stressed about one thing or another, I would put it on and enjoy the look and feel of it as I walked around. This went on, sporadically, with different skirts at different times until I was in my mid-forties when the urge to have more women’s clothing other than skirts became very strong. We had been in Canada since 1981 and at this time, I was married with all the children living at home, so I had to be discrete. In the early nineties, I had a job for a few years that was far too stressful for me, and I think all that stress had more effect on me than I thought. There were also other factors that I won’t go into at this time.

For several months, I dressed at home whenever I got the chance. I would walk around the house and admire myself in a full-length mirror. To be honest, it became very stressful for me not being able to go out of the house and not being able to tell anyone. Then, one day, I became so desperate that I phoned my cousin in England. We had always been very close. I was very nervous telling her, especially describing what I was wearing. However, she said something to the effect of not being surprised that I was taking a walk on the wild side and was very accepting even saying that she looked forward to hearing more of my adventures.

The urge to go out while dressed became overwhelming. I decided I would go into the city, which was about a three-hour drive. I set off with my feminine clothing in a travel bag and changed at a big rest stop. It felt so good to walk around the car wearing my flared skirt, pantyhose, etc.

The experience in the city was not entirely a good one; I still found it exciting and stimulating. After several stops before going right into the city, I parked up and walked along one of the main commercial avenues. A very popular venue with the university at the east end, and a lot of young people around. While walking along, a hollerin’ and yellin’ began behind me. I did not look around. They sounded like they were quite close and shouting, “Look at the tranny! Look at the tranny!” This was accompanied by a lot of whooping and caterwauling. I ducked into one of the stores to evade them. When I came back out, I couldn’t see anyone around who might be the culprits, but when I set off down the avenue, they once again began their harassment. I had no choice but to duck into the next store, this time staying in there for a long time before coming out. When I did, I had no further trouble.

I went into a women’s clothing store, selected a top that I would like to try on, and presented it at the counter. The lady behind the counter was obviously not pleased to see me in her store. She told me that anything I tried on, I had bought. Just as now, women were free to walk into any men’s store, try on whatever they liked, and make the decision whether to make the purchase or not based on that; not me or those like us; not then!

Despite these negative experiences, I still enjoyed the freedom of dressing the way I wanted to and having a day out in the city.

I was in no way convincing. I did not have any make-up, nor did I have much of an idea of how to apply it. My dress style was more suited to standing under a lamp on the street corner than browsing the shops, and I had no idea how to fit in.

Soon, I began hinting at my dressing to my wife. In my mind, I had made enough of them that she would know. Of course, she didn’t. I made the great mistake of employing the “Shock and Awe” technique. I had been in the habit of running up the stairs to get changed before she came home. This time, however, I was set on letting her catch me. She was horrified, and even though the next few days we talked about it, I decided to back off and put crossdressing on hold. I even went so far as to purge all of my recently acquired outfits.

Again, this was in the nineties, a very different time than today.

Aurora Lynnette Eden

More Articles by Aurora Lynette Eden

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.