Jill Goes To Work Dressed -
As A Railroad Engineer
. . . . and Survives !!!

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A New Year's Resolution?

By Jill R. Ambrose

This true story originally appeared in the February, 1997 issue of Innerview, the monthly newsletter of Crossport, the Transgendered support group in Cincinnati, Ohio, and the Spring Issue of "The Femme Mirror", the quarterly publication of Tri-Ess.

Working Enfemme! A Pipe Dream?

A New Year's Resolution?

Did I make any this year? Yes! They will go un-named but I'm still working on them. One item that was not included on my list, but was certainly in the back of my mind as the clock clicked over to 12:00:01 on January 1st was the idea of actually working enfemme.

For some time now, I have been fantasizing about the possibility of Jill being a female railroad engineer.

Perhaps it was a combination of events that led to the possibility turning into reality. Maybe it was my sometime utter disregard for negative consequences. And then again, it could have been my need to 'push the envelope' just a little further.

Several times over the past year, I have gone to work from dinner or a meeting, and then changed into my work clothes upon arrival. Most of my co-workers and the office staff know of my transgendered status, and they have seen my photos.

On the occasions that I have arrived at work 'dressed', only a few other employees were present, and they either accept the fact or don't care. Since I usually work the third shift, the number of people on duty is minimal.

As fate would have it, one night I arrived to be greeted by my immediate supervisor, who knows,and the new General Manager, who had only heard about my crossdressing. The encounter went well, as far as I could tell, but there was certainly uneasiness on my part, and probably theirs also.

Nothing was said to me directly afterwards, but the GM nows refers to me as 'our crossdressing engineer'. I can only imagine that he would not like the idea of me working as a female engineer.

Left My Shoes At Home

On another occasion, I arrived at work and during the course of changing clothes, realized that I had left my (required safety) work shoes at home by the front door. Wouldn't you know that the GM would pick that night for a safety meeting. I sat two chairs from him in my stocking feet, trying to keep my feet hidden under the chair. I managed to get through the meeting without incident, and quickly got out of the office, where I felt a modicum of safety.

The night went well, except that I felt weird running the engine with flats. Fortunately for me, I did not have to disembark from the engine . . . UNTIL - - quitting time. I had planned on shutting down the engine and quickly going home, with no one else aware of the situation, except for my conductor. NOT!!

As the night progressed, it became apparent that we were not going to make it back to our terminal, and that we would have to be relieved on the road. When our time was up, my supervisor arrived with his van and the relief crew. They were all standing on the ground near the engine as I climbed down. Later, he pulled me aside and asked if I had worked that way all night. I truthfully admitted that I had (what else could I say?), and he reminded me of the rules. THAT was IT! What a relief!!!!

Buoyed by the apparent acceptance of those around me, but still fearful of the consequences, I had all but dismissed the idea of actually working enfemme, until recently.

The Plan Unfolds

My regular conductor was transferred to another run, and the person that was sent as a replacement was an old friend that I enjoyed working with. In addition, I knew that he was open minded. Another new addition to the crew was a third person, a young man in training. Chris, my conductor, and I (read Jill) had in the past made arrangements to meet for some late night visits to the local hot spots. Unfortunately, something happened both times and we never got together.

The three of us worked together for the better part of the week, with Chris constantly making remarks about Jill to me and in front of our trainee. I tried to skirt around the issue, not wanting to involve the young man, until he admitted that he knew all about Jill, having been told by my former conductor.

One thing led to another and Chris suggested that it would be neat if Jill were to be the engineer some night. I countered that if it were to happen, a Friday night would be best. Plans were then formulated for Jill to work on Friday. Everyone was ecstatic.

The Moment of Truth

Knowing that I would have to change into workclothes once I arrived, and to show the trainee what Jill looks like dressed up, I arrived in heels and a two piece outfit. Imagine my surprise when I walked into the office and the daytime crew was just getting off duty. Neither had met Jill before and, although they did not look shocked, I'm sure that they were at least surprised. I calmly said hello and sat down to consume the food that I had with me, while carrying on a light banter with them.

Shortly after they left, my crew arrived. Our young trainee was impressed and commented that had he not know it was me, he would have assumed that I was a GG. After that, it was time to don my jeans and work boots. I almost decided to work in my skirt, but it was too darn cold outside.

Even thought I was bundled up against the cold, and there were few outward signs that Jill was at the controls, all three of us knew and we enjoyed the situation. I was in heaven!!!

The evening was uneventful, and I had a great time, playing the situation to the hilt. My hair kept getting in my face and I constantly had to brush it back to my shoulders. When the engine eventually warmed up enough, I shed some of my outer garments and rode without a jacket so that I could experience the joy of working in my sheer black blouse. I was very aware of my breasts all night and relished the thought of the nipples pushing against the sheer fabric and of feeling them every now and then. I was on cloud nine all night.

After our tour was over, Chris suggested that we get a bite to eat, so we all headed for Denny's. I took the time to get out of my jeans and boots and slipped back into my skirt, and off we went. The three of us spent a pleasant time together reminiscing before we headed in separate directions.

Time will tell if there are any repercussions, but I have talked with my supervisor since my FIRST experience, and nothing was said. I'm sure that Jill will be at the controls again soon. When the weather warms up again, we plan to do a photo shoot on the engine.

To continue reading about Jill's Real Life Adventures, Go to Index of Jill's Real Life Adventures
.. or go directly to one of the following items .. Out of the Closet . . . Into the Spotlight .. or .. My Brushes With The Law - Trip To St. Louis .. or .. Prelude To Dallas .. or .. My Enfemme Flight to the Texas "T" Party.

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