Crossdressing adventures are a fun part of my crossdressing journey although some were not fun at the time. I decided to do a series of posts because I have quite a few new to launch crossdresser’s following this blog that I think will enjoy them. Some are young and others just late getting started.

Crossdresser Adventures




Back in the early 1990’s long before I discovered CHIC and after constantly prodding my wife for several years, she agreed to accompany me to my 1st crossdresser convention. This was to be my first crossdressing adventures fully dressed. She was O.K. with it because we knew nobody in Texas so getting caught was a very low possibility. I meticulously planned the trip 1st registering for the Texas “T” Party then booking the hotel which I believe was the 7 Oaks on Old Austin Highway (more later) in San Antonio Texas. I then booked the airline tickets from Los Angeles to Austin for the convention. This was early internet days with nothing offered like today, so I kept paper copies of all my travel information in a folder in my briefcase. We planned to arrive early Friday afternoon then drive to the hotel so I could start getting ready. We figured two days would be enough for our first-time crossdressing journey.

Everything was on schedule, and we arrived on time, got the rental car and headed for the hotel. I gave my wife the map and told her to locate the 410 Loop which would take us to the hotel. She could not find it after repeated attempts so frustrated, I pulled over to do it myself. To my amazement I could not find it either which just never happens! I broke out the folder to get my travel documents in my briefcase and AHA! the mystery was solved. My crossdressing adventures was off to a great start. We were in the wrong city 75 miles from the convention. After booking the hotel on the Austin highway I called and made the flight reservation with Austin fresh in my head. I then booked the flight to Austin instead of San Antonio where the convention was. So, it was Micki the road warrior through the Texas Hill Country to San Antonio.

crossdressing adventure


 Behind schedule we arrived at the hotel in San Antonio, checked in and went to our room to get ready for our crossdressing adventure.

We missed the Friday night cocktails and dinner but got to the lobby shortly after. Walking down the hall of the hotel my wife asked me if I had been out in public like this before. I was dressed as a woman so took the liberty of answering like a woman with a question. I said why do you ask? To which she answered, you walk very well in heels and are not the least bit nervous. BUSTED! Then she said slow down, point your toes and put your shoulders back.

We had drinks in the bar chatting with some other folks there and retired about midnight. Saturday, the crossdressing adventure corrected course and after breakfast we shopped in the vendor. My wife attended a seminar for wives in the afternoon. In those days nobody left the safety of the hotel congregating in the bar or vendor area instead. Having said that the 9-hole golf course on the property was closed for the season but they opened just for the “T” party tournament.

Saturday night’s dinner was both a welcome and a farewell for us having missed Friday nights fun. Saturday night was dressy with formal gowns, cocktail dresses and tailored suits. After dinner they had the usual awards for this and that in the community followed by the golf tournament winners. Yes, they wore ladies golf attire and played from the ladies’ tees. Then everyone was off to the bar for dancing and more drinks until the wee hours.


The TEXAS “T” PARTY was truly a crossdressing adventures and had a tradition of the Sunday farewell breakfast that was not really an official event. It was where everyone hung out all morning watching people walk in and tried to figure out who they were last night. It was great fun inspecting everyone up and down trying to place them the previous night. My wife and the others at our table were intent on discovering the mermaid from the night before. She was not in costume but wore an exotic green dress that really popped with her red hair. Her very attractive wife I nicknamed the dancer because of her skill on the dance floor along with her toned legs.

The excitement grew when the dancer came in by herself and sat down at a table. Nobody moved staying seated knowing the mermaid would soon appear. Every guy that walked into the coffee shop that was of similar build was stared down until he passed the dancer. Then he was cast off like a used Kleenex eyes darting back to the door. Then it happened, a meek little man with balding red hair resembling bookkeeper from a Hollywood movie came in. He was walking in the dancer’s direction then sat down with her to everyone’s shock. Nobody would ever guess this guy looked so good as a woman. Now that the excitement was over people started paying their checks and leaving the restaurant. More than one stopped and complimented the mermaid on how good she looked the night before. It had to make her feel good which she deserved. I wanted to compliment the wife on how good she looked the night before but decided it would not be a good idea to fly home with my ribs taped up. My wife is funny that way.

I will forever owe a debt of gratitude to Linda & Cynthia Phillips and their crew at the Texas “T” Party for getting my wife and I started crossdressing adventures the right way at the classiest crossdresser event ever done.

More adventures here!

crossdresser trust

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