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The following is a true story written for publication in June of 1995 concerning the trials and tribulations of one of the most memorable days of my life - My Coming Out of the Closet. This version is essentially the same as the original with a few minor revisions mostly to eliminate some local references.
In The Closet
Like many others, I'm sure, for quite a few years, since I was a little 'girl', I have had the desire to 'dress' but have only had the opportunity to do so in private. That situation changed early in my marriage, over 30 years ago, when my wife was informed of my propensity to crossdress. During that time and only until recently have I worn more than just female undergarments. I can now dress openly at home with my wife's knowledge, but not necessarily her acceptance. Four years ago, I discarded ALL of my male underwear in favor of panties, which I now wear exclusively.
Over the years, there were many opportunities to shop and then dress in the privacy of my hotel room while on business trips . Not once did I get the courage to exit the safety of my room and venture outside as a female, although I entertained the thought many times.
Recently my computer provided an outlet to tap for information on crossdressing. I became a "lurker", that is, someone who reads the various topics on the on-line bulletin boards, but does not announce his/her presence.
I was surprised to learn how many people openly expressed their interest in crossdressing, and admitted to wearing panties and other female garments under their male attire. Also, as surprising, was the discussion of organized groups that held conventions and get-togethers. Ah - some day perhaps, I would be able to attend one of those affairs.
I spent a lot of time over the past several years reading the dialog in the CD section of Prodigy, and lately whatever I could find on the Internet. On those rare occasions when I would acknowledge my presence, the name Jill Ambrose was used.
The Turning Point
Perhaps six months ago, I was in downtown Cincinnati and as is my custom, I grabbed copies of the free tabloids that are available. The passage of time and old age has erased the memory of exactly which publication contained the information directing me to send for information about Crossport, the local crossdresser support group, but I followed through and sent for a brochure.
The introductory material arrived a few days later in my P.O. Box, and I immediately sent in my money . . . a twenty dollar bill, in lieu of a check which would have revealed my identity.
A short time later, an envelope arrived with a copy of the December and January newletters. After perusing these two issues, with my heart pounding, I decided that this indeed was an organization that I would like to belong to, but there was a conflict with the meeting night, which could not be resolved.
It was exciting to read of the adventures of the members who were relating their anecdotes while dressed in public. Although this situation was still foreign to me, I could empathize with their dilemmas and achievements.
Each succeeding issue talked about a 'Be-All' which would be held in Cincinnati, and while I fantasized about attending, the notion was out of the question. But . . .perhaps I could 'lurk' at the hotel and observe the activity.
The arrival of the May issue of the "InnerView" stirred me to action, but not immediately. Editor Bobbie asked for a volunteer to run the spotlight at the Be-All. It took a full three days of internal debate before I called the Crossport Hotline and offered my services. A few agonizing days later, Jennifer called and when we talked about what was involved, and with my background in the theatre, I assured her that it was 'a piece of cake.'
Am I Coming Dressed??
Everything seemed great until Jennifer asked, "You are going to come dressed?" No, I had not planned to do so, especially since I have worn facial hair for the past 30+ years. Jennifer explained that it was rare that people dressed with a beard, but it was not unheard of. This did nothing to alleviate my fears, and prompted many thoughts of backing out.
It took a couple of more weeks of agony, coupled with a strong desire to take advantage of this opportunity, to convince myself that now was the right time. When Jennifer called again to confirm that I was still coming, I said yes and announced that I would be dressed, . . . and clean shaven.
Since this was to be my first time out in public, plans were formulated to explain the sudden loss of my facial cover, get off work for the Friday events, and acquire a suitable wardrobe for the Be-All.
Most of my outer clothes were obtained second hand and would not be suitable for wearing in public, so a visit to a plus size shop was in order. I knew that I wanted a 'pretty' dress, but had no idea as to size or style. In addition, cosmetics, shoes and a wig were also needed.
The Shopping Trip
The make up portion of the package was relatively easy. Armed with a list of what I perceived to be needed, I trekked off to K-Mart and Wal-Mart. Over the course of several days, Jill picked up a good supply of various foundations, liners, lip-stick, mascara and blush.
The clothing selection was not as easy. Except for undergarments, the pickings in my size, 18 to 20, were slim at the discount stores. This called for a visit to (shudder) a clothing store. With much trepidation, Jill arrived at a major Mall and walked the length of the facility several times, peering in windows and quickly visiting the plus size departments of Sears and J.C.Penney before garnering enough courage to walk into Stuart's Plus 20 minutes before closing.
A very friendly and helpful young lady spent a good half hour showing me various outfits and making suggestions on the pretext that these were to be worn at a party the following Friday. Jill selected a two piece blue suit with a long sleeve blouse in white, as the 'pretty' dress selection was non-existent. When I arrived home and tried on the outfit, I found that it fit well and thus gave me an idea of what sizes to look for in future trips.
Saturday morning, I was up bright and early with plans to visit two other Stuart locations and Kohl's, both of whom were having sales. All in all, it was a very fruitful trip which supplied all of my wardrobe for the Be-All, except the 'pretty' dress, for which I'm still looking. I spent a long time at Kohl's, picked out a dozen items to try on, and waited for my chance to use the women's dressing rooms, which never came. Perhaps it was best as I eventually carried my selections to the men's area and tried on the clothes there, eliminating over half of the items because of size problems. I was very happy with my purchases.
Two businesses that advertised wigs in the yellow pages were circled and the hunt was on for a wig. The purchase of the wig was very straight-forward and after trying on only two styles, Jill made her selection.
Shoes in my size presented a big problem. Almost all the shoe and discount stores only carry women's dress shoes in sizes up to 11, too small for Jill. I did find a pair of casuals in 11 wide that would do 'in a pinch', but still needed a pair of dress shoes. Someone recommended a store dealing in larger sizes, which I discovered was going out of business. Because of this, the selection was very small, but still I was able to find one pair that, although a little tight, would fill the bill. Fortunately, later, I was able to purchase both a pair of flats and heels at the Be-All.
A Bombshell
Everything seemed to be progressing smoothly for my planned transformation to Jill on Friday morning, when my wife dropped a bombshell. She would be covering for someone at work next week and changed her off day from Monday to Friday (POW / SOCK). At this time she had not met Jill, and knew nothing about the coming out party. What was a poor girl to do? My plans to spend whatever time it would take to get ready at home Friday morning were dashed. Luckily she was not home Thursday evening and I packed everything into the car and reserved a motel room.
No one in the family knows about Jill, but I had been making references for several weeks about Jill to my daughter-in-law, who I thought would be open minded enough to accept Jill, without hating me forever. I gave her no clue as to the nature of Jill's business with her, but indicated that Jill would like to meet her. Her first question of me was, "Poppi, is this Amway?" Other than to answer her questions with generalities, I gave no concrete information about Jill. She was flustered, but under the circumstances, could only wait until Jill contacted her.
The Big Day
After several nights of tossing and turning, trying to get to sleep while thinking and fantasizing about the Be-All, Friday morning finally came. A good-bye kiss to my wife and the luggage safely in the motel room, I set off to transform myself into Jill.
The transformation started with the removal of body hair. The first thing to go was 35 years of facial hair. Naturally, I nicked myself with the razor several times, but did no serious damage. Following a quick assessment of my new youthful look, I continued on and shaved my arms and legs.
Two and a half hours later, after fighting with eyelashes, press on nails and smudged makeup, Jill was ready to walk out the door. This was the first time that I had ever applied make-up and it was strictly trial and error, but I was satisfied with the final results. I breathed a deep sight of relief as I looked at Jill in the mirror and was pleased with the final results. I knew that I could pass.
REALLY Out of the Closet
With a lump in my throat, I opened the door and looked outside. Directly before me was my car and nearby was standing a couple engaged in conversation, who looked my way. Several other people were within sight. Bravely, I made my way to the car and started loading it, all the while 'knowing' that everyone was watching me. On the final trip before departing, a young man whistled and yelled to me, "How you doing babe?". I looked and smiled and immediately got into the car and took off, thinking to myself that I must either look good or like a slut, but satisfied that someone, a stranger, found me attractive. It was a very good, satisfying feeling.
It was then that I realized that I still had to check out of the motel, especially if I wanted my key deposit back. Unfortunately, my admirer was standing by the office, and now did not seem like a good time to check out. I was concerned about registering as a male and returning the key as a female. I stopped by later and to my relief, everything went smoothly.
A Potentially Bad Situation
While dressing, I entertained thoughts of introducing Jill to my daughter-in-law and as I still had some time before my noon 'Be-All' meeting with Jennifer at the Holiday Inn, off I went to her place of employment.
It was indeed a long walk to the reception desk, where I asked for Jackie in my best female voice. As she was being paged, I stepped back a few paces and waited, my heart again pounding wildly. Jackie came up front, looked at me and asked, "Is someone helping you maam?" I acknowledged with a meek "yes" and she turned to the receptionist to inquire who called for her. I felt great that she did not recognize me. After ascertaining that I was there for her, Jackie approached me again and I extended my hand asking, "Hi, are you Jackie?" I knew that my next words would hit home, as I volunteered, "My name is Jill."
In the next few seconds a thousand thoughts raced through my mind, wondering what her reaction would be. With a look of total surprise, she uttered, "Poppi, it's YOU." "We need to talk."
We went to her desk and talked for perhaps fifteen minutes, holding hands all the time. Her response to Jill was mostly positive, but she had many questions, and said that we needed to do something with my clothes.
On The Road Again - To the Be-All
This experience was very comforting and gave me the confidence to venture forth as Jill. As I traveled to the Be-All, I was elated with myself and looking forward to many happy times with my alter-ego, Jill.
Arriving at the Be-All registration table, I found Jennifer and introduced myself. Her approving look helped build my confidence as we settled in working on the staging for the evenings' Miss Be-All Pageant. As the afternoon progressed, the room transformed into a suitable place for the Pageant with stage, runway and lights. During the afternoon, I met so many wonderful, encouraging people who helped me get over whatever butterflies I still had. As did most others, I shed my female voice for the balance of the Be-All.
Around six-thirty, we went upstairs and prepared for the evening. A change of clothes and some fresh make-up and Jill was ready. I purposely sat with CrossPort members at dinner that evening so that I could meet some of the girls that I had been reading about in the newsletter for the past several months. It was a very pleasant experience, and especially reassuring to me, as most were surprised that this was my first time in public enfemme.
Soon it was showtime. I took my place behind the spotlight, where I had a great view of the room. It was difficult keeping my mind on the assigned task, as my eyes wondered over the assembled crowd, admiring the many gorgeous women in attendance. I was thrilled when Jennifer introduced me while working the spotlight and commented that this was my first time dressed in public. I relished the applause. What a high!
Time To Face The Music
The evening was over too soon and now it was time for what I perceived would be the toughest part of my transformation. I was going home to introduce Jill to my wife.
On the way home, I again had many thoughts about backing out and not telling her, but rationalized that my life as Jill would be much easier if my wife knew, and approved. Ha - fat chance.
The confrontation went much better than I had hoped. We spent a long time embracing and crying, and in the end, I was satisfied with the knowledge that my wife had met Jill and now knew my secret. The next morning, she was surprised that she had not observed the loss of my mustache, and acknowledged that she had not recognized me as Jill.
Day Two
In the back of my mind, I had planned on returning to the Be-All on Saturday. We talked at length and came to a general understanding about Jill and I, and she agreed to help me pick out a new wig, as the present one made my face look too full. With this partial approval from my wife, Jill got ready for day two of her new life.
After spending a good two hours with make-up and clothes, I set out again for the Be-All. Arriving at the Hotel, I ran into Jennifer, who was surprised to see me again so soon, as my original plans did not include a second day at the Be-All. Taking advantage of my new status, I attended several seminars and visited all the vendors.
In the interest of brevity, although this account has already grown too long, I will conclude with the note that Jill met so many decent, interesting, and supportive people over the weekend who offered help and encouragement. I especially want to thank Jennifer for making possible and laying the groundwork for my coming out. Many thanks also to Bobbi and Beverly for being there and acting as a sounding board for my many questions. Thanks also to Dr. Richard Doctor for his helpfulness and the quality time that we spent together.
Although Jill will always be in the closet to a certain degree because of the dictates of society, more and more people are aware of Jill's existence and I am confident that Jill will venture forth into the outside world on a frequent basis.
I LOVE being a GIRL!!!
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 ..
My Brushes With The Law . . . A Trip To St. Louis .. or ..
Prelude To Dallas .. or ..
My Enfemme Flight to the Texas "T" Party .. or ..
Jill Goes To Work Dressed . . . and Survives
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