Belle of the Ball

 This is actually a two part post combined into one because it involves a similar topic.

As I began to become more comfortable in going out on Halloween in feminine attire, I decided to try my good fortune by going to large so called straight venues. In my mind to do it correctly I had to go by myself without my wife.

The first time I tried it was with my first wife who was very vanilla and didn’t really seem to care. I often thought I could tell her I was going out for gender realignment surgery and she would not care. At any rate, as Halloween approached that year, I had already made up my mind I was going to the biggest venue in town as a woman and see what happened. 

My “costume” was all in black with a tight sweater, mini skirt, black tights and blonde straight wig. All topped off with a black beret. The whole outfit worked well as people I thought I knew merely passed me off as another costumed Halloween person. However, all of it came to a halt when a person in a full mask stopped to see me and said he knew who I was. I was floored! How could anyone see through my elaborate “costume”? Finally I said how did he know me and he said I looked exactly like my Mother. It turns out he was a childhood friend who knew my Mom. Turned out later he was a notorious transphobe who made extremely derogatory comments about me behind my back. But that’s another story.

Other than him, the night I thought went well and I enjoyed myself immensely. What I was discovering though was how natural I felt when I dressed in feminine mode and interacted with the public.

The second part of this post deals with another experience I had when I was away from home training managers for a company I worked for. This one occurred with my second wife who also knew I cross dressed but was much more strict about my comings and goings. 

Once I found out I was scheduled for a training seminar in a city I had to overnight in for a couple of days over Halloween, all I really had to do was figure out how to sneak a “costume” out of the house for the evening along with all my work clothes of course. With a little creative packing I was able to pack what I needed.

For the evening I basically had the same objective. Dress to blend with the other women at the venue in their Halloween costumes. I found a tight, short faux leather skirt and top, added fish nets, heels and heavy make up with a blond wig and off I went. 

Much like the first night, all went well except for a few unwanted butt feel ups. All to quickly as I always say, it was back to being my same boring guy self. The only problem this time was I had to chase my gender euphoric fog in a hurry. The very next morning I had to teach a class at 8 AM.  I made it time wise after triple checking I removed all the makeup from the night before. 

While I certainly wasn’t the “belle” of either ball, I still had a great time!  

Halloween Dreams

 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!


Halloween has become sort of a bittersweet day for me. 

While I have all the pleasant (even thrilling) remembrances of Halloween’s in the past, these days since I have been living all these years as a fulltime transgender woman, Halloween has become just another day. Plus, the covid virus has taken out any idea of having another annual witches ball this year, I can’t even put together a costume for that. 

Over the years though, I spent weeks (or longer) stressing on what I was going to wear on the one magical night a year I could go out and be myself. Typically I started with “streetwalker” drag and quickly advanced to a “professional woman” look. I wanted secretly to be viewed as a cis woman who showed up without a costume. 

Naturally, all these efforts met with varyingly levels of success. I went from my high heels killing my feet, to being recognized by an old acquaintance because I looked like my Mom, all the way to being asked by a future Washington politician (and his date) to another Halloween party after the one we were at. 

Then there was the first date I had with Liz (my partner) when we went to a major witches ball in Cincinnati when I was dressed as a wench and enjoyed all the pirates and belly dancers. 

As I seemingly close the door on Halloween this year though, I keep thinking there is always next year! 

Another Halloween

Another Halloween has came and gone…almost. I have seen a few places around here in Cincinnati which are having theme parties this weekend which are loosely Halloween based. After all, some people I know would want Halloween celebrated year around. 

One of those is the “moderator” who I have mentioned extensively here in Cyrsti’s Condo. She is the one who got bounced from the board (and all her activities as social director) of the established cross dresser-transgender support group I am a member of. I am rather proud of the fact I have taken the high road in the whole affair. In fact, at Monday’s meeting, I was prodded to give my true feelings on the subject. But just shut up.

Since, to my knowledge, none of them read my blog, I can do it here.  I really only have a couple problems with the “moderator”. I think she is and has been a little frenetic in the way she approached having “socials.”  Her invitations began to take on the idea of when you went out, you were going to meet her. Leaving the “group” idea out. In other words, the socials became Stacey’s and not Crossport (the group.) I think in her mind though, she was simply going out and inviting anyone else to join her.

On a bigger stage, I think her biggest problems came with her attitude concerning transgender safety as a whole.  Since she hadn’t had much of a problem with going public with her transition, she figured society had changed and no one else should have a problem either. While times have changed, we all know they haven’t changed that much. I think she was ignoring the people in the group going through heart wrenching times with spouses and family. 

Finally, I think her total willingness to to throw caution to the wind and give out her personal phone number to anyone who wanted it was ill advised. 

Going full circle back back to Halloween, Liz and I actually went to two themed events, so life was good. My costume was simple, I dressed as a witch. Complete with long flowing skirt and spider accessorized witches hat. My goal was simple, to be viewed as a woman dressed up in a simple costume. 

Plus the actual Halloween evening was so nasty weather wise, there weren’t even very many Trick or Treaters. 

I do hope where ever you are, you accomplished all your Halloween dreams!  

Halloween Dreams

It amazes me after all these years I can still have so many vivid memories of my early Halloween experiences.

One of the earliest goes back to the 1980’s when I lived near Yonkers, New York. I was working for a Wendy’s franchisee then and one of my assistant managers invited me to a Halloween get together she was having. I saw it as the perfect opportunity to get out and live as a woman for a short period of time…if I could figure out how to do it. 

Since my wife wasn’t really into Halloween and knew why I was, it was fairly easy to convince her not to go. Plus, she was always against what she thought were my sleezy costumes. With her out of the way, I was free to costume myself anyway I pleased.

I picked out a short mini dress, heels and one of my fave wigs for the evening. If you remember, big hair was “in” in the 80’s, so I fit right in. After freshly shaving my legs, applying my makeup, panty hose and getting dressed, it was time to go.

What I wasn’t prepared for was how well I was going to fit right in. 

It turned out, the Halloween “party” she invited me to was actually a group of her girl friends who all were going to one of their local taverns to party. I was in heaven when I saw all these women dressed almost like I was. Initially they were in shock when they saw me and looked me over head to toe until my friend told them who I was. Then I was accepted. 

The tavern was within walking distance of her house, so here we were all in our heels clicking along as we walked to the party. Again, I blended right in and felt great. 

Once we arrived at the tavern, we proceeded to order drinks and the other women got up to dance. Unfortunately I have exactly no rhythm and kept my seat. Inwardly though, I was savoring every moment and even got asked to dance. Again, I politely declined. 

All too quickly the evening had to end and I had to head back to my routine existence. However, the word spread through out my store how I had dressed for Halloween. Nothing much happened as I just said I always wanted to do it. Resulting in a few “yeah right” smiles.

Little did I know how long the memories of the evening would linger. It showed me how it would be to interact with women on their own level. If only for one evening.   

Witches Ball

What a night! Liz went approximately two days without sleep getting decorations ready. The good news was we filled the venue and made a nice amount of money for the two charities we give to. 

As far as a costume goes, in a moment of panic, the two outfits I was planning on choosing from didn’t work. I finally decided on my long flowing black embroidered skirt and black and white print blouse/top. I also bought a lighter foundation to give me a more “witchy” look. Finally I added the sparkly witches hat Liz bought me with a big spider on the side.

The reactions were varied and took me back to previous Halloweens. Of course I received quite a few looks and one compliment from the best looking cis woman in the crowd. I believe she was biased though because she has known me for a while now. She is obviously a big fan of transgender people. Still, a compliment is a compliment! 

Anymore, Halloween is a different type of evening for me.  I have nothing to prove anymore with a feminine costume. In fact, I think the whole evening tends to get me clocked.  I am always aware of the compliment “you look beautiful”…for a man in a dress. Oh well. 

Since we decorated the venue, we had to clean it up.  All of a sudden, a late night turned into an early morning. We had to be out by one o’clock and made it by five minutes. 

By the time we finished loading and finally were done chatting it was around two in the morning. 

The trip home was unremarkable outside of me getting my skirt stuck in the door. You could tell I don’t wear a skirt much.

The major problem we encountered was stopping at a certain 24 hour hamburger chain I’m sure you would recognize if I told you. Every time I go there, I come away with the feeling being hungry was a better bet than eating there. So shame on me.

At least the employee at the drive thru window kept referring to us as “ladies” as she apologized for how long the order was taking.