Coming Out to Employees?

 

Halloween Witches Ball Image
Liz on Right 

As we rapidly approach Halloween and my wife Liz's operation coming up, I thought it was time  for another Halloween experience while I still had time. 

This one happened when I was managing a fast food restaurant just outside of the New York City  metro area. More precisely, very close to the Bronx. As Halloween rolled around, once again  I was stressing out about what I was going to wear. The pressure was on since it was nearly impossible for me to leave the house we lived in dressed as my feminine self. I was back in the mode of waiting another year to escape from my mirror until the next Halloween rolled around.

As I faced the pressure head on, I decided to go all out as I decided what my "costume" was going to be. I put together what I thought would be a potentially a sexy look without crossing the line into being trashy. I pulled out my shortest dress, along with my highest heels. Most certainly, my wife's most hated outfit on me. In this case, I used her motivation of me to spur me on. For once, since she wasn't going anyhow, I decided she would have to get over it. I would have to put up with her displeasure with me for the next several weeks but it was worth it for me to pursue my dreams.

As I said, my outfit was going to be short and sexy as I to the best of my ability fool the world to what my true gender was all about. Little did I know, I would be able to find a situation where I was able to blend right in. 

As it turned out, one of my assistant (woman) managers was going out to one of her local taverns to celebrate Halloween with her friends and she invited me along. After I dressed, did my makeup and hair and was ready to go. When I arrived at my manager's house, it turned out the friends she was going with turned out to all be tall and beautiful . As it turned out, by pure accident, At least in the height department., I fit right in. When I first saw all of them, as the room grew silent, you could have heard a pin drop. Time seemed to stop for me as they examined me from head to toe. Of course I could only guess what they were thinking as we left for the short walk to the venue where we were going. Thank goodness for me (in my heels) it was not a long walk.

As we arrived, I learned a valuable lesson about being with other single women who were attractive. The first thing the women did was essentially split and worked the room. They left me on my own which was an experience in itself. After I bought a drink and found a seat at a small table, I settled in to try to enjoy my evening in the world as a novice transgender woman or even a transvestite. And it turned out, the night was far from over. As I tried to sit by myself, I attracted attention from an older guy who kept bugging me to dance. Which I refused although deep down I was flattered. Finally, the night was over, the group of women broke up and headed their own ways. 

I ended up back at my restaurant which I knew was closed by then. What I didn't count on was, the closing crew would just be getting done and they would see me in my "costume." Surprisingly to me, the response was positive even to the point of one of the guys saying I had good legs. 

More importantly, the backlash from me dressing as a woman for Halloween was a non starter for most of my crew and life went on. The only variable was my assistant manager who I think couldn't wait to tell my boss who smiled at me differently for awhile. However it was New York and there were bigger issues to deal with than me dressing as a woman for Halloween. Which was one of the reasons I wanted to move there from our native Ohio to begin with. 

As far as my second wife went, she finally made me pay my dues as only a woman knows how to do. I learned from it and moved on. Knowing I had been able to experience a truly wonderful evening to think about and remember forever. 

A Night at the Theatre

 This is yet another Halloween experience which helped me to break out of my gender closet and experience a possible life as a transgender woman. 

Image by Danie Franco
on UnSplash

Years ago Columbus, Ohio completely restored a very elegant classic vintage theatre downtown. With interest I learned the new venue would be hosting a late night Halloween horror show silent movie complete with accompanied music from the restored theatre house organ. Aside from being a total restoration geek, I immediately sensed an opportunity to extend my feminine Halloween adventures. From there the evening began to come together quite nicely. Little did I know how much fun I would have. 

The first thing I had to do was get four tickets. Two for my first wife and I and two for two other close friends I wanted to go with. Then I needed to put together a "costume" for the evening. Actually, back in those days, my options were as limited as my wardrobe. Following several unsuccessful trips to thrift stores, I settled on a mini dress which I had even worn on another Halloween adventure but with different people. Supposedly, changing up what I wore would keep people from guessing how serious I was concerning how I was perceived as a woman. The last thing I wanted to do was however was try to be an obvious jokester of a man in a dress. 

As it always happens, the time coming up to the Halloween evening seemed to go so slowly as this was the only time of the year I could escape my self imposed gender closet and explore. Before I could explore I had to decide if I was going to throw caution to the wind and go all out to appear as a sexy woman. Back in those days, shaving my legs was a rare and often wonderful experience and I decided to do it for the evening. Shaving of the legs is the one biggest giveaway I think between someone dressing as a woman as a joke and someone who is a serious cross dresser. In other words, going all the way for me was the only way to go. 

The afternoon of the party, when I left work, I was able to leisurely prepare for my night on the town in "C-Bus" which was only approximately a half hour away. I drew a hot bubble bath and made sure all of the hated hair was off my legs before I was able to slide into a new pair of panty hose without ruining them with a run. Then came the makeup, mini dress, long blond wig and heels which I would regret wearing later. After downing a couple of "road pops" for courage it was time to head out, pick up our friends and go to the theater. 

These friends in particular had seen me before dressed as a woman so I don't think there was much of a surprise to them when they saw me. My wife always knew I was a cross dresser so I know for sure she wasn't surprised. 

The unfortunate part of wearing the heels I did came when I learned how far I was going to have to walk in them as parking was at a premium. Needless to say my feet weren't used to walking that far in heels and were protesting. I had to hitch up my big girl panties and pay the price for fashion. It all was so worth it once we arrived and saw all the other beautiful and creative costumes. For better or worse no one seemed to notice the tall blond in heels and mini dress. The movie with the background organ was wonderful.

Not as wonderful as my big night out at the Ohio Theatre.  

October Already?

 It's difficult to believe but October has arrived again. Around here at least, for the most part, the weather has done her part to welcome in the Fall season. 

Most importantly, October brings with it the very important Halloween holiday. At least it's a holiday of sorts to most novice transgender or crossdressing women. It's a chance to break out of closets everywhere and experience the world as your authentic self. Who you were born to be. 

I know Halloween was very important to me in my progression out of the closet. Through my so called "costumes", I learned many things including if I dressed appropriately, other people would mistake me for a woman. It took me awhile to understand how deeply ingrained my desire to lead a feminine life was. Finally, I came to the conclusion all those years I was living as a cross dresser alright, just not as a woman. I was cross dressing as a man.

Throughout the month of October I will try to share the most impactful Halloweens I experienced. Very quickly my thrill in presenting as a convincing woman came full circle. I found my impossible dream of living full time as a transgender woman may indeed be possible. 

Also, if you have a Halloween story, please send it along!

Living the Halloween Dream

This experience goes way back into the days when I got out of the Army in the mid 1970's. I did what every other returning vet did (not),  used my GI Bill to get a second degree and bought a little bar with a friend.  My Dad came up with the classic quote about the bar when he said "At least it has two doors, so the flies don't have to stop when they pass through."

Of course I was into "warp" mode as far as my cross dressing activities were concerned. After years of forced depredation from anything feminine in the Army, the last Halloween party I went to before I got out primed the pump so to speak or the lipstick.

Last Halloween 

To put the time sequence in perspective, I was discharged in January, my first wife in March and we were married later that year.  I was out to her as a cross dresser and she made the comment (I have mentioned here in Crysti's Condo) that she really didn't know which one of me was going to pick her up at the airport.  She is a very good person, the mother of my daughter and we see each other and get along to this day...but... she is a just very easy going person. Sometimes I thought if I came home and said I'm going to go for SRS tomorrow, she just would have said that's cool dear. I know some of you will think,  "Wow, that IS  cool!" You have to understand me. If something is too easy then something is lurking in the shadows to nip you in the rear plus I had a very conservation macho family to consider too.

At any rate, Halloween that year turned out to be fun filled trip over to Columbus (Ohio) where one of the newly restored Victorian theaters was having a "Spook Out".  At midnight they were presenting the classic silent "Phantom of the Opera" with the restored house organ presenting the music. We went with another couple who were "kind of " in costume which I was too-mini skirt, long hair, heels, hose and all.

All these years later, I remember several things. First of all, this was one of my first experiences of feeling how uncomfortable an extended time walking in heels could be plus a mini skirt is wonderful to be admired in the mirror,  but took constant work to move in modestly.  Secondly, for the most part I wasn't even noticed at all because of all the other wonderful costumes. I still remember the guy dressed as the Pope, complete with two other guys following him in costume holding his cape.

As much of a rush these early Halloween's were though, the more painful they became later.  The next day I was already trying to figure out what my next cross dressing experience was going to be.  A very difficult process which made me a very grumpy person.  The problem was I knew staying home in front of the mirror in a dress just wasn't going to be enough and I had no idea of what enough may actually be.  So I took my "Halloween Fix" and moved on.