TRANSVESTITE CROSSDRESSING 101 Archives Page 2 of 15 -

TG ROCKTOBER 2025

Posted on October 9, 2025October 9, 2025 by Micki Finn

I made it to TG Rocktober 2025 this afternoon in time to get my room and settle in which included checking in with the TG Rocktober 2025 registration folks. Because it was close by and convenient I went as the little old man version of Duke so nobody would suspect. Said high to Davina who was handling the check in with her wife Cindy and got all set up. Miss Micki will stay in the suitcase tonight as I tired and need to rest up for the TG Rocktober 2025 Opening Gala Thursday night. This year is going to be different because the long time home of previous TGR and other TG events opening nights closed suddenly earlier this year. It was decided to just do a dinner at the Bistecca Steakhouse here in the hotel for a limited group on a prepaid basis. I guess the response was overwhelming because based on the huge response it morphed into much bigger deal. The limited steakhouse dinner has moved to the banquet room upstairs so i think it is fair to say there will be more than 8 of us!

CROSSDRESSER EVENT PLANNING

Posted on September 26, 2025September 26, 2025 by Micki Finn

A very rewarding and fun part of crossdressing is the excitement and planning for an outing. Regular dinners rendezvous with friends are great but I am talking about large organized events like DIVA Las Vegas or TG Rocktober. The events are back to back this year with TGRocktober ending on Sunday and DIVA starting the next day Monday. I will be attending TGRocktober which is a different structure so planning what to wear for it differs from DIVA.

CROSSDRESSER FASHIONS

Posted on September 18, 2025September 18, 2025 by Micki Finn

When it comes to crossdresser fashions many of us have a certain style that we prefer as opposed to any current trend. My preferred style came about in my early twenties when tailored suits were the norm for business and social outings. I have evolved beyond suits these more casual days opting for tailored jackets and skirts instead. Mixing and matching skirts and jackets gives me a great deal more options than the limitations of suits. My style really never goes out of fashion because the cuts are more traditional. I have pieces that have been in my closet for years and you would not know it.

FRIDAY NIGHT CROSSDRESSER

Posted on September 13, 2025September 13, 2025 by Micki Finn

I feel sorry for all the crossdressers out their who are alone with their crossdressing. All of us were there at some point in our lives but many others have developed a network of other crossdressers. For some lucky ones they have a crossdresser bond with others they have met over the years. Last night four of us got together for dinner at a favorite restaurant in Long Beach. We all come from different backgrounds but share the crossdressing experience even though one of the four was Tonya’s wife. That might sound strange but wives of crossdressers if they are accepting take an active role in her husbands dressing.

UNDERCOVER CROSSDRESSING

Posted on September 6, 2025September 6, 2025 by Micki Finn

For many of us crossdressers who don’t indulge our girly side daily and live under the radar it is important to not leave any tell tale signs of being her. We all know people who seem to notice everything about you like the pimple on your nose from 300 yards away. They are the ones you have to watch out for so I will share some of my tricks to keep the big secret.

HARMLESS CROSSDRESSER / HARMLESS TRANSVESTITE

Posted on August 28, 2025August 28, 2025 by Micki Finn

I got the idea for this post after thinking about my last adventure. We all know crossdressing does not go away so managing it well pays off. My wife and I made a place for Micki Time in our schedule years ago and it works very well. The harmless crossdresser idea is based on what I do during Micki Time. A couple of days each month I get dressed as the most glamorous woman I can conjure up. I then go for dinner and drinks in a nice restaurant with friends or alone. That’s pretty much it other than possibly attending a show in Las Vegas if I’m there.

CROSSDRESSER MASK

Posted on August 10, 2025August 10, 2025 by Micki Finn

I got to thinking about the many crossdressers that never go in public for fear of being recognized. Then I thought about how many times I have walked past someone that either knows Duke or Micki. It’s one or the other with very few exceptions because they know either Micki or Duke. Only a hand full of very trusted people have seen both Duke and Micki. The makeup I am wearing while dressed serves as a crossdresser mask hiding my true identity.

CITY CROSSDRESSER FRIENDLY RESTAURANTS

Posted on August 3, 2025August 3, 2025 by Micki Finn

Saturday night I had reservations at the Portland City Grill and the entire afternoon to get ready with some makeup experimentation along the way. Years ago I would never just make a reservation and go to a new place without calling ahead to see if they were a crossdresser friendly restaurant. I don’t anymore because its not an issue in most places and my attitude is I belong their. I have never had a problem anywhere with that attitude and in Liberal cities its not even necessary as they are all crossdresser friendly restaurants.

CITY CROSSDRESSING

Posted on July 28, 2025July 31, 2025 by Micki Finn

I have always enjoy city crossdressing because there are so many great restaurants to choose from. People tend to dress up a bit more at the nicer places so I don’t stand out as much. This adventure has me back in Portland Oregon again at the Historic Benson Hotel in the hart of downtown. Built in 1912 the Benson is now in my collection of crossdressing VINTAGE HOTELS and it is definitely one of the more elegant structures.

HAPPY TRANSVESTITE / CROSSDRESSER

Posted on July 13, 2025July 13, 2025 by Micki Finn

I got to thinking the other day about my life as a Crossdresser which took me to the beginning. I was pretty young at around 6 or 8 years old from what I remember which, is a significant age that I will expand on later. I did not have a label at that age and was alone with my strange little pastime never even experiencing guilt at first. That was installed when I got caught the first time and when I vowed to never do it again. The first time! I would make that vow over and over again many times and getting quite good at it. I got better at guilt management over time as well which, came in handy when the time came to take the inevitable step and venture out in public.