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.
Crossdressing for Christmas this year was the culmination of the years planning for all the members of CHIC. I was very pleased to see so many of the members and crossdresser wives wearing gowns this year. The picture below was my contribution for this year and I absolutely loved it.
CROSSDRESSED FOR CRHISTMAS
When I saw this dress at Macy’s in November I scrapped my plan to wear the blue cocktail dress I bought earlier in the year. I thought the sequins on one side and not the other looked glamorous. The rhinestone shoe ornaments on my black suede pumps topped off the whole look for me that night.
CHIC CHRISTMAS PARTY
This event has pretty much 100 percent attendance for CHIC members and wives. Our party is in the wine cellar private dinning room below the main restaurant. It starts with a hosted champagne cocktail hour with servers passing a variety of hors d’oeuvres as everyone mingles.
Dinner is a sit down affair with wine donated by a member and started with a pasta ravioli appetizer. Salad followed then the main course with a choice of veal scaloppine piccata, Salmon steak with shaved apple and fennel or, vegetable risotto followed by an assortment of pastries for each table.
CROSSDRESSED AT CHRISTMAS
After dinner the cameras come out and its picture time for those wanting pictures of them crossdressed at Christmas time. Not everyone wishes to participate so we do it in a special corner of the room away from the rest.
I did not have permission to publish Lady “L”s picture so I covered her face. It was easier than trying to cut her out and piece the picture back together.
Sadly we must wait until December 2020 to wear our formals again unless something comes up for New Years Eve.
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.
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.
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.
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.
We have all done it, everyone pretty much starts out that way unless someone dresses you as a joke or experiment. Most of us indulged in our fascination with women’s clothes all by ourselves. Many men will always be crossdressing alone away from prying eyes and the possible negative repercussions of others.
21ST CENTURY CROSSDRESSING
Thankfully there is much more acceptance of crossdressing today and there isn’t the stigma that existed in years past. I go out today to all kinds of mainstream businesses and entertainment venues without getting much more than a glance. It wasn’t always that way though.
I grew up crossdressing alone and just had an article published in SisterHouse based on my early crossdressing experiences. Actually lack of experiences would be more accurate combined with lack of knowledge of crossdressing. You can follow this link the the article GROWING UP ALONE. Tasi says it is somewhat sad in the beginning which is true but don’t feel sorry for me I have moved far beyond that time.
I am firmly invested in 21st century crossdressing and only look back only to share with others especially the younger ones what it could have been like for them.
Forget about using the ladies room you were more worried about being the scourge of the community and shunned by virtually everyone. Mothers would not want their children playing with you and you would never get invited to a birthday party. If discovered you would be immediately mistrusted and you’re motives questioned. It was against the law to impersonate a female in public and you could be arrested. I guess they assumed you were trying to trick some unsuspecting lad into being attracted to you.
Follow the link to SisterHouse for more growing up in mid 20th century California and crossdressing alone.
Crossdresser wives sometimes accompany their husbands out in public in fact some are quite comfortable doing it. Last weekend a group of CHIC members all rendezvoused in San Francisco for weekend of fun crossdressing. There were 5 crossdressers and 3 wives joining their crossdressed husbands.
The Redwood Room
Tonya (seated) and I are posing with the big chair in the Redwood Room near Union Square. Both our wives were with us but were camera shy but not us. We had just come out of the Redwood Room at the Clift Hotel after enjoying a nightcap. It was our first night in town and we enjoyed a leisurely dinner at Jardinière with other crossdressers wives and their husbands.
We were there a total of 3 days and dined at The Big 4 on Friday night and Farallon on Saturday night. All of us Crossdressers and crossdresser wives went to see Beach Blanket Babylon after dinner.
The days were spent shopping for most of the ladies at Macy’s, Nordstrom, Sephora and other lady destinations. All of the stores are Trans friendly and go out of their way to give you the help you need. This is especially true trying on clothes in the changing rooms where sales clerks will find an empty room for you. They will also check on you to see if you need a different size so you don’t have to keep getting dressed in between trying clothes.
I do not dress during the days when my crossdresser wife joins me for outings. It is part of the compromise we worked out decades ago because she is more comfortable under cover of night. However I do shop dressed during the day on outings that my crossdresser wife does not attend which, is the majority of the time.
Traveling T Gurl
I go to San Francisco several times each year in addition to Las Vegas, Seattle, Portland and other cities without her so I get plenty of shopping in throughout the year.
Passable vs. Acceptable is the question that prompted me to update my CROSSDRESSER PASSING IN PUBLIC page. Summer is almost behind us and my thoughts have drifted toward getting dressed again after a summer of doing guy stuff.
Micki is planning a new road trip and in that process security is always an important factor. Because passing is something I am not able to do. I don’t attempt to pass as a woman when I am dressed en fem. Micki made a decision many years ago that it is not practical for me to pull it off.
PASSABLE VS. ACCEPTABLE
That is not to say that I don’t put a maximum effort to look as glamorous and feminine as I can. I just chose not to attempt to deceive people into thinking I was a real woman.
The real me is far more interesting and fun than the hybrid I would be creating. Given the choice of being passable vs. acceptable as a crossdresser I choose acceptable crossdresser.
Most importantly there is no guarantee that I will be accepted when out and about which is why I take precautions to minimize my risk of danger.