Crossdressing history comes in two parts, one is the personal crossdresser’s history. The other is part of the collective history of crossdressing men wearing dresses over the ages.
Younger crossderesser’s will have a relatively short history but, are none the less part of the collective history of crossdressing. The younger crossdresser’s are the inspiration for this post. It also pertains to others regardless of their age that have recently made the leap to explore crossdressing.
CROSSDRESSING FEAR AND TREPIDATION
Crossdressing in public isn’t what it used to be and the young and newly launched gurlz benefit from the efforts of those who came before. Long before Caitlyn Jenner drew so much attention to the subject when she came out to the world others were pushing the envelope. Some at great personal cost like divorce, job loss and in some cases jail. The farther back in history you go the worse it was.
30 years ago I would have been extremely uncomfortable going into the 555 Steakhouse dressed as a woman. It is an upscale restaurant in downtown Long Beach near the convention center. The 555 is always crowded liquored up convention folks. Getting the cold shoulder from the management and frowns from the customers would have been my expectation and that would be the good part. Fearing being asked to leave or having customers request being moved were also a consideration. My worst fear though would be to have had some dunce pull my wig off and play catch with his boozed up buddies.
Please understand my paranoia of the 555 Steakhouse was in no way based on the establishment but, my fear of society in general in those days.
Last month I made a reservation at the 555 online for 10 people on the Friday night before our club (CHIC) Christmas Party. I did not notify them in advance that we were going to be crossdressed. I did years ago out of consideration for the restaurant. The reason being that they know me there. Micki has eaten their many times in large and small groups being treated as a lady every time. I think I am in their computer system so they know what to expect when we arrive. That Friday night the place was really crowded but our food & service were exceptional. Other than we were dressed better than most of the women there nobody paid us much attention.
MATURE CROSSDRESSER HISTORY
I have posted before on mature crossdressing history when I wrote about a book my friend John C. Gunn authored called I’m Dressed Your Not. John went by the name Lane when we met at a CHIC meeting about 30 years ago. She is in her 90’s now and I and others learned a lot from her especially the fingernail technique I use. Another post I did was about Laverne Cummings who would be about the same age as Lane had she not passed a couple of years ago.
I recently came across some information on the internet that took me back to the early stages of my crossdressing history. It along with seeing how different things are nowadays for younger and newly launched crossdressers are what inspired this post. Possibly after reading it those with less crossdresser history will gain an appreciation for those who came before and blazed the trail.
CROSSDRESSER DOCUMENTERIES
I came across a series of YouTube crossdressing videos by JoAnn Roberts from the mid 1980’s along with a tape from the Phil Donahue television daytime show.
JoAnn passed in 2013 but not before making a significant impact on the crossdressing history of many of us.
She started her own publishing company and began producing LadyLike Magazine.
In 1985 she wrote and published Art & Illusion, A Guide to Crossdressing.
She was also one of the founders of the Renaissance Transgender Association, Inc. This was all done in an era where you could easily lose your job on just the rumor that you were a crossdresser.
Her courage and others like her eased the path for others by educating the public on crossdressing. In 1995 she was a partner in the online website Trans Gender Forum later named TG Forum.
It was TGForum and JoAnn that hosted the 1st CHIC website that I built almost 20 years ago. JoAnn was very patient with my lack of knowledge of websites back then.
Halloween crossdressing is a favorite for the men dressed like women community regardless of your preferred label. Halloween is considered the national holiday of crossdressers everywhere. This year I chose the pirate costume and took the name Captain Morgana.
The Halloween crossdressing party was again this year at Wanda & Susan’s house again. The members of CHIC gathered in their costumes from spooky or fun to sexy cat women for a fun evening. My wife picked this outfit for me this year and it fit great. The hat leather leggings and the bottle of Captain Morgan spiced rum was my touch.
PRE HALLOWEEN CROSSDRESSING FUN
Wanda lives some distance from our normal Long Beach haunts so some of us get hotels close to her house for the weekend. That leaves us an opportunity for Friday night fun or what we refer to as the FB4. Micki & Wanda at Agostinos Friday night you can see more pictures of Wanda’s adventures HERE.
This time I chose Augostino’s Ristorante Italiano for the dinner of nine ladies. It is located across Pacific Coast Highway in Capistrano Beach and they treated us great. To say we were overdressed is an understatement with it being a casual beach restaurant no Halloween crossdressing.
Augostino’s closes at ten but we are just getting started so we went two doors down to the Sunset Grill for some cocktails and dancing for a few of the brave gurls.
We sat outside and enjoyed the cool breeze and sipped Cosmo’s listening to the DJ while watching the ladies dance. Once again we were severely overdressed but they did not mind or maybe they just thought we were Halloween crossdressing!
One thing that has definitively changed over the last twenty years is the public acceptance of who we are. People are treating us very well in most cases. It is just a matter of educating them and showing we are worthy of their respect and actually pretty fun if given a chance. This was evident when our gurls invaded the dance floor and the women already dancing turned around and started dancing with them.
Crossdresser wife support for your dressing is truly a gift. My wife has always been a great help with my crossdressing even though she chose not to actively participate in the beginning. Wigs, makeup, shoes, outfits and accessories are areas she has helped me with. Most things I willingly accepted but the short wig took decades for me to buy into.
Crossdressing Wig
My wig style was pretty much shoulder length through most of my dressing career. Like a caring crossdresser wife support she was constantly suggesting the shorter ones but I never liked how they looked on me. That changed a couple of years ago when we returned to our hotel from the CHIC Christmas Party. She took off the short wig that she was wearing and asked me to put it on. She wanted to see how it looked on me as it was a complimentary color. I knew what she was up to but put it on anyway. She teased it up a little higher than she wore it and the look on my face said it all. I loved the way it looked but, the wig cap was too small for me. The two wins for her was I now was ready to explore the Micki in short hair concept along with she one the argument.
Godiva’s Wigs
I was fortunate to discover Godiva’s Secret Wigs online because they are great quality and come in large cap sizes. I have purchased several large cap wigs from them but what I call a short wig they refer to as medium which, refers to the length. The two wigs below come in large cap size but are medium length.
Freedom in Nutmeg F colorTrixie in Creamy Toffee color with roots
For a Traveling T Girl like myself there is a wonderful advantage to these wigs. I pack them in a large zip lock freezer bag with the wig turned inside out. When I arrive at the hotel I open them up, hold them upside down by the tag and shake hard 3 times. I style them later when I go out with my long fingernails. It only takes a couple of minutes and has cut down my time getting ready.
Trixie wig Creamy Toast R (with roots)
On trips where my wife accompanies me she takes over on the styling which always looks better than mine but, she has been at it longer.
She has also bought me numerous Betty Boop figures over the years because she knows Betty was my first love as a child.
Maybe Betty was the influence that made me dress in the 1st place.
Weekend crossdresser pretty much describes the majority of us even those who have retired. I am no exception and joined some of my CHIC sisters for a couple of nights of partying in Long Beach California last weekend.
FRIDAY NIGHT CROSSDRESSING
The Friday night before our regular monthly CHIC meeting has turned into an additional weekend crossdressing outing. Originally it was just a few people some traveling from afar and others living local but a couple of years ago that changed. Younger couples joined the club and discovered the fun of spending a weekend crossdressing in the safety and acceptance of Long Beach.
A couple of months ago Wanda & I posed for pictures on a Friday night.
Last Friday it was Erica Marie and I mugging it up at the same location as above only a different room.
Erica was smart enough to know she should go back to her hotel room or possibly it was her lovely wife prodding her. Either way she took the smart path and left leaving me with another sister to close the bar that night. I hate when I do that! Tons of water and a nap Saturday afternoon got me back on my feet just in time to get ready for that night.
Saturday afternoon I started the wonderful process of getting ready for the evening. I already knew what I was wearing that night and was overdressed as usual so it was just makeup, hair and nails. This night we added a few more sisters and wives to the weekend crossdresser event heading to the opposite side of town for a wonderful Italian dinner. We were 15 people in all more than half of which couples. The restaurant was on the famous and happening Pine Avenue section of Long Beach.
The evening ended with some pictures and hugs goodbye. This top got several compliments throughout the evening which made me very happy as I was a bit timid about wearing it.
Crossdressers passing is a popular topic across the INTERNET and the world in general. I don’t worry about it and have discussed my thoughts in another post dealing with acceptance vs. passing.
I attended DIVA Las Vegas 2019 this year but only attended a few evening events. My days were spent shopping at the Miracle Mile Shops and the Fashion Show Mall crossdressed of course. Did I pass? Was I one of the DIVA crossdressers passing among the crowd? I will never know because everyone treated me as the lady I was dressed as. They addressed me with the correct pronouns, greeted me with a smile and in general gave me good service. I was surrounded by hordes of people all over town doing what people do in Vegas.
DAYTIME SHOPPING
The first day at the Miracle Mile I wore a black denim jacket with lace accents sewn on. Blue jeans and clack suede flats. The second day at the Fashion Show Mall I wore black jeans with a buckskin faux suede jacket and black suede flats again. Nobody gave me any significant looks or attention. I did get looks mind you but considering everyone else was in shorts and thongs can’t judge one way or the other. Was I read or a crossdresser passing? Did they look because I was a nicely dressed woman? Could being over dressed cause them to look longer? Who knows? Based on their demeanor I will say they accepted a crossdresser for how she was dressed and moved on.
DINNING WITH CROSSDRESSER FRIENDS
I joined Wanda & Susan friends from CHIC on Tuesday night at Ruth’s Chris Steakhouse for dinner followed by cocktails at the Cromwell Hotel.
Wednesday after shopping I had a 5:30 dinner reservation at Stack Steakhouse in the Mirage Hotel. I dined with four CHIC members who were attending DIVA Las Vegas 2019.
Dinner was earlier than normal because Wanda had gotten us tickets to the Terry Fator Show. The show was at the Mirage so it was a short walk to the theater.
Thursday night was the DIVA Las Vegas farewell dinner at Off The Strip.
I attended with four CHIC members and met two prospective members. I also had dinner with Cassandra and Susan from the Rose City “T” Girls in addition to Michelle the current Vanity Club President. CHIC members Wanda and wife Susan joined for a picture below.
A fun week for sure and if you have never attended DIVA Las Vegas you might want to try it. They have a big sister program for newbies.
Being a traveling T Girl road trips are something that most of us do to at one time or another. Some often like myself others only occasionally but we all have the same challenge. What to take and how to get it there in addition to how to pack it all. If driving, you can take everything you own depending the size of your vehicle but flying takes some planning. My wife organized my packing process years ago and I have used her system for years with great success.
WHAT TO BRING
My traveling T Girl road trip starts with planning my evenings out differentiating between casual and dressy nights. Once I decide on an outfit for a night, I lay it on the bed and pick out some jewelry to go with it.
ACCESSORIES CAN MAKE OR BREAK THE OUTFIT
Setting the jewelry on the garment gives me an idea how it will look when worn with the clothing. Then I hang it on a door nob or cabinet nob so I can lay the purse and heels I choose below it.
ACCESSORIES
Once I am happy with the nights look the jewelry goes in a zip lock sandwich bag and hung on the hanger by punching a small hole just below the zipper.
I do this for every night I will be going out along with days outfits. Daytime outfits are far easier to put together because the emphasis is on casual as opposed to the night time glamour. Makeup is toned down also as not to stand out so much in the crowd. Shopping rules the days so jeans and flats come first followed by a thin top so I can try clothes on over it. My preference weather permitting is a light jacket with a zipper in front. That way I don’t have to take my wig or blouse off before trying things on. Jewelry is conservative also with smaller earrings and bracelets. My wig for daytime will be light brown as opposed to flashy blonde shades. Again, the jewelry will go in a zip lock over the hanger.
When all the outfits are selected, I put a clear trash bag over the hanger of each outfit to guard against wrinkles.
TRAVELING T GIRLS
Packing wigs depends on the wig short or long full or straight. I have used cases which take up lots of room but protect the styling and they are great if you are driving. Flying traveling Tgirls are another story due to luggage limitations on size, weight and quantity of suitcases. I have used a trick for traveling crossdressers taught to me years ago by the late JoAnne Roberts for longer and full hairstyles. You place the wig in a plastic bag folding the excess bag under the wig and insert it into a plastic she box. Takes up very little room in the suitcase and preserves the styling well.
You can take collapsible wigs stands with you or you can buy large pop bottles to use for wig stands when you arrive at your destination.
Milano 2 piece wig stands slide together with offset slots in each of the halves
My wigs are all short and can be packed inside out then shaken upside down. I can style them quickly and I bring portable collapsible wig stands. I just purchased two new stands pictured above that I will be trying out but think they are going to be great as they are very compact.
Fake fingernails are a must for crossdressers and they can easily be bought on line or in most drug stores. Size can be a problem as they are designed for women who have much smaller nails. Some of the prepackaged nails will fit but thumbs usually don’t. My solution is to but unpainted nails in my size form Talon Nails and shape them myself.
FRENCH MANICURE
A couple of years ago I started experimenting with doing nails in a French Manicure style. It takes more work than just cutting, shaping and painting fake nails but is worth the effort.
The process is the same as the one detailed on my CROSSDRESSER FAKE FINGERNAILS page. The big difference is when you paint the fake nails it will be with a French Manicure polish designed to look like your natural nails.
On the nails above I painted 3 coats of the polish on the right using my nail wheel.
I let the Polish dry overnight and then mask off the section of the nail I will paint white the next day.
Because I will be using an airbrush to paint the tips I need to mask off the back part of the nail. The masking strips are available at most any beauty supply or of course Amazon.
Now its time to fire up the compressor and get to work on the tips. I use the white tip paint mixed with nail polish thinner 50/50 so it will spray easier. I tried brushing the white tips on but, it was always too think. The fake nails did not look natural like you see women wearing on the street.
I let the paint dry overnight and then remove the masking the next day.
After letting the dry another 24 hours I put two coats of Orly topcoat on and i am all done.
I bought my airbrush equipment from Amazon and the compressor from Harbor Freight.
Mature crossdresser’s are seen more and more out among the mainstream public. The Friday night before our monthly CHIC meeting affords an opportunity for some members to go out 2 nights in a row. Some travel a great distance to attend meetings and like myself get a hotel room for the weekend. Wanda and some others joined joined me for the January Friday B4. She and I are in the lounge of one of our favorite restaurants in Long Beach. The only crossdresser wife attending that night was Wanda’s who took the picture.
SEASONED CROSSDRESSING
The member ship of CHIC ranges from 42 to 93 the average being about 60. We are a fun group who look forward to our monthly get together’s. The knowledge attained over decades is willingly passed along to the younger members if they are receptive.
MATURE CROSSDRESSER’S WITH STYLE
Micki Finn
I like many mature crossdresser’s prefer to dress on the conservative side without being dowdy or fuddy duddy! I love this jacket and skirt combo that I purchased separately and paired together. The look is timeless which is my goal when ever I purchase something. Only dressing a couple of days per month means if I buy something trendy I may only get to wear it once before it goes out of fashion.
MATURE CROSSDRESSER’S POSITIVE IMAGE
I have some shorter skirts slightly above the knee but mostly prefer the hem mid knee. They will always be in style if not fashion and don’t send the wrong message to those I encounter while out and about. The last thing I want is to give the impression that I am available to some boozed up dude looking for action. I always wear the wedding rings my wife bought me in case anyone looks but that doesn’t always deter people.
When I am approached in public it is typically from women curious about my being dressed as a woman. Some notice my ring and inquire whether I am married to a man and some are shocked to find I am heterosexual and married to a woman. I have enjoyed many enlightening conversations with these women and even their husbands on occasion. I am sure the conversations would not happen if I was dressed in a manner that made them uncomfortable.
This years CHIC crossdresser Christmas Party we had 20 attending and it was a joy watching each one descend down the staircase in their beautiful dresses and gowns.
I attended with four CHIC members and met two prospective members. I also had dinner with Cassandra and Susan from the 
