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.
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.
CHIC Christmas Party for our local crossdressing club is just around the corner. It is the highlight of the year for all the members of the club. The party is dress to impress time from elegant dresses and skirt suits to formal gowns. Some shop all year while others rush to the finish line. My shopping is done and I opted for a formal this year after a dressy suit last year pictured below.
CHIC Christmas Party is attended by pretty much every member of the club and member wives make a special effort to attend this event. Because some members live great distances from Long Beach their wives only attend this one meeting. It gives them a chance to catch up with crossdresser wife friends.
FOOD AND FUN
The evening starts with club sponsored cocktails and hors d’ oeuvres in the bar of the restaurant. The venue is a popular mainstream long Beach restaurant so we are mingling with the general public. It is never a problem and attracts a bit of attention as we are better dressed than most patrons.
Wine and more hors d’ oeuvres await downstairs in our semi private lounge room where the picture above was taken. Around eight or eight thirty we sit for dinner and desert until about 11:30 when the night officially ends. The CHIC Christmas party may end but not the partying as some will head to the bar upstairs or across the street for more libations!
There will most likely be other Christmas Parties going on that night also as in the past. The ladies attending the other party are typically very complimentary of our cross dressed members. They appreciate the time and effort we put into our makeup and hair. Gowns also get a lot of attention being that you usually don’t seem them other than on TV.
The party is just days away and I can’t wait to start the process. Pictures to follow in a few weeks.
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.
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.
Crossdressing in Las Vegas has not been one of my favorite experiences as a rule. Its starting to grow on me though as I am experimenting with different hotels hoping to find a better match.
I don’t gamble more than $100.00 per trip on video porker machines so much of what goes on there does not interest me.
DIVA LAS VEGAS 2019
I attended this year again and stayed at the Flamingo which I did not care for at all. Too many people and my room was the absolute farthest from the lobby way too far in 4 inch high heels. Thank God I stuffed my foldable ballet slippers in my purse, they saved my tootsies.
THE CROMWELL HOTEL
Three weeks after DIVA I found myself back in Las Vegas again for a crossdressing in Las Vegas / golfing / shopping adventure. This time we stayed at the Cromwell Hotel. Its right next to the Flamingo and liked it much better. It is a much smaller property with only 188 well appointed rooms. The staff was great and the elevator was only 50 feet from my room. Once down on the casino floor it was a short walk to either the strip or valet parking in the back. Right next to the valet is the UBER & LIFT pick up point.
The only disappointment on the trip was the first night we had a dinner reservation at Giada De Laurentiis restaurant. Two years ago we had dinner there and it was over the top. We a window table overlooking the strip and a great server.
CROSSDRESED FOR DINNER
We were crossdressed both times but this night they seemed intent on giving us an undesirable table. I don’t know if it was how we were dressed or if the hostess was a moron or both. The first table had me sitting next to a wall looking at another wall. Like when I stood in the corner at school. I rejected it asking for the empty window table a few feet away. She said she had to check and see and took us back to the bar while she checked.
We arrived at the restaurant 15 minutes ahead of our reservation but sat at the bar for another 15. We sat while she filled all of the available window tables. Fifteen minutes after our reservation time she came back and took us to a table almost as bad as the one I rejected. She said the table I requested was in an area that the server was not taking anymore customers. The second table was not the window I requested and I only had to look at one wall.
Because it was almost 8:30 PM by this time we accepted the table and had dinner. Our servers were great and took very good care of us but I was so annoyed by the table incident I don’t even remember what I ate.
I can’t say for sure if the hostess was screwing with us because we were dressed or not but there are too many great restaurants in Las Vegas to give her another chance.
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.
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
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.
Closeups are very popular for some people in the trans world when it comes to selfie photography. Mature crossdresser’s magnifying mirrors allow for another closeup. The days of simply leaning forward to put you false eyelashes are gone sadly so we seasoned gurlz need technology.
Magnifying mirrors are a wonderful aid for those who lack the vision of the younger crossdressers. Over the years I have used a variety of them and had to rig an adjustable mounting system in order to adapt to various challenges. My dressing is done traveling staying in hotel rooms which vary in bathroom layouts so adjustments are needed. Over door hooks, suction cups, and braided cord has suited me well.
I found the JiBen lighted makeup mirrors last year and ordered the 7X and 10X lighted one from Amazon for about $26.00 each. I tried them out this last trip and absolutely love them both. The 10X is perfect for putting on my false eyelashes allowing me to get the corners right. It also works great for putting eyeliner gel in between my eyelashes. Mature crossdresser’s magnifying mirrors make this possible without poking my eye out.
The 7X is better for eyebrow detailing and mascara along with other tasks that don’t need that much magnifying.
Both mirrors are lighted using AAA batteries but I did not use them this time. They install on any smooth clean surface like window or mirror by pressing the base against the surface and then rotating the suction grip clockwise. The mirror will suck down on the surface and hold tight for days. When you remove the mirror just rotate the suction grip counter clockwise and the pull the small rubber tab on the back toward you. Thats It!
Crossdresser Christmas Parties only come around once a year and some of us start the planning months in advance. Others never stop shopping for that special nights show stopping outfit year around. I am guilty of the latter and are always on the lookout for something special.
This year though it was a favorite beaded suit from my classic closet.
My CHIC Sister Wanda joined me for this photo at the 43rd annual CHIC Christmas Party at L’Opera restaurant.
The picture above was taken in the Wine Cellar at L’Opera Restaurant in Long Beach. It is a semi private room below the main restaurant elegantly decorated in elegant Italian motif.
In my 26 years as a member I have attended most of the parties. From my first in a members back yard to the Gable Lombard Suite at the Hollywood Roosevelt Hotel.
This years CHIC Christmas Party had 20 elegant ladies attending including wives. It was a joy watching each one descend down the staircase in their beautiful dresses and gowns. We have had over 40 attend at past parties like the Roosevelt but this year we opted not to invite outside guests. That made it extra special because you knew everybody at the party and we are a pretty close group.
The evening began with complimentary hot Hors d Oeuvres being passed around by servers. There was also cheese and fruit at a table for seconds. We had limitless champagne during the happy hour with the servers continually refilling your glass.
A sit down dinner followed starting with Calamari Fritti appetizer then choices of Veal Osso Buco, Salmon and Chicken Breast. Wine was included with dinner with both white and red selections. Again with attentive servers re filling your never empty glass. Desert was a special treat with an assortment of Petits Fours consisting of Tiramisu, Creme Brulee, Chocolate Mouse.
Dinner was followed by lots of fun conversations and a lot of laughter until almost midnight when most called it a night with a few exceptions. Some continued the party across the street at the Federal Bar until the wee hours.
It was a wonderful night of love with new and old friends from CHIC. I started looking for next years outfit the next day.
Crossdresser colors you say! What is that? Years ago I found out quite by chance at California Dreaming a San Francisco crossdressing event. I was wandering around the vendor area looking at all the wares available when I came upon the Donna Fujii Cosmetics booth. There wasn’t much going on during the day in that most everyone was in the city shopping. As I was talking to the lady in the booth she asked if I wanted my colors done. I replied crossdresser colors? She explained that everyone should know their colors especially crossdressers.
I sat down in the chair and she explained the difference between cool colors and warm colors. My skin is medium and I was wearing a dark brown wig so while my skin says warm my hair said cool. She started with cool and placed a piece of silver metallic cloth on my shoulder and asked me to look at my face especially my makeup. She then placed a gold metallic cloth on the other shoulder again asking me to look at my makeup. When she then removed the silver cloth it seemed like my makeup changed looking much more complimentary or warmer. She advised switching to warm tones like blond wigs and warm palette colors for makeup.
Clothes such as red really pop when worn with a blond wig.
Finding anybody wearing much color is difficult today women, crossdresser’s or anyone else. Yes black is slimming but gets old seeing everyone dressed that way.
HAIR AND MAKEUP
The most important colors to get right are makeup and hair so if possible get the makeup right for your skin then do the wig color and style. The ideal would be to try on wigs dressed with your correct makeup on. Shorter styles are easier to work with because you don’t get distracted with the style and concentrate on the wig color complimenting your makeup. I think you will be surprised pleasantly and please purchase a wig if you take advantage of the Solon’s expertise.
Another possibility is to attend a crossdresser convention / conference where there is a wig stylist exhibiting but again if at all possible purchase something from them. Diva Las Vegas this spring should have a wig company working with them.
Crossdressing for Halloween is probably the ultimate fantasy for every crossdresser at least when they first begin anyway. I think like me everyone thinks it would be the safest way to venture out for the first time crossdressed in public. Although I thought of it I went out dressed for many years before finally going to a Halloween party. It was safe given by a crossdresser and her wife in their home. I got ready in my home and my wife sneaked me out the door keeping watch for neighbors.
After many years one of the CHIC members threw a Halloween party last weekend, Of course everyone was crossdressing for Halloween. My wife talked me into wearing a “Queen of Harts” costume. She was not attending with me so I was to go alone. That is not a big deal other than I was not staying at a motel. Motels often let you park right outside your door so you only have a few steps to get in the car. I was staying in a high rise Marriott hotel on the 7th floor.
I have stayed in this Marriott many times and am comfortable with it. The staff knows me and I think they are always interested in what I will be wearing each night I am there. I am always overdressed and I think the ladies approve of my taste.
Saturday night was different because my wife goaded me into getting dressed in my costume at the hotel. That meant I was going to be driving to the party dressed in it. I wanted to rent rent a second room just for that night to get ready but had trouble selling her on the cost.
All dressed and ready to go I ventured out of my room and down the hall to the elevator as the Queen of Harts. I was probably only 20 feet down the hall when I heard a door slam behind me. I would have company in the elevator going down and he showed up 2 seconds behind me. Fortunately he asked if I was going to a party and I said yes, to which he said well you look great. I thanked him and we got into the elevator.
The usually quiet lobby was full of people checking in for a big wedding that night so I gave them something to talk about and left.
The party was about a hour away and was great fun but I left a little after ten. after changing into a more contemporary jacket, skirt and heels.