Mainstream crossdressing is something I only dreamed of when I was a young crossdresser. Actually fantasy is probably a more accurate term because it occupied my mind mostly while awake. Leaving the house dressed did not really start until my mid 30’s. It was still something you could be arrested for so was an irregular occurrence. My mainstream crossdressing only existed on business trips and consisted of driving around late at night then back to the motel. I think it was in the late 80’s when I made my first mainstream crossdressing trip In Dallas Texas.
MAINSTREAM CROSSDRESSING THE 1ST TIME
While at one of the beloved Texas “T” Parties friends insisted that a friend and I join them for dinner. We assumed it would be a Gay restaurant which was the typical (SAFE) destination in those days especially in Texas. I knew I was in trouble as the city lights faded behind us but hoped maybe dinner was in Houston. Nope! They reserved a very nice steakhouse in a suburb of Dallas filled with regular folks. Not my idea of a perfect place for a paranoid CD to do mainstream crossdressing. Everything went well when they seated us at a nice table until we took our seats. There were crossdresser wives with us so I let them decide who sat where and I guess one of them hated me because I ended up directly under the spotlight. Its the perfect place for a CD who rushed to get ready and not ecstatic about her presentation that night preferring a dark corner of the restaurant.
My first time mainstream crossdressing was an education as the guys I was worried about in the restaurant really did not want to look at us. It was the women they were with that kept looking at us all night. They kept pointing us out to the poor guys who obliged them with a brief glance then back to their meal. The staff was very nice to us and when we left their was no gallows or rope tied into a hangman’s noose so it was all good. Then again maybe the fact that we pulled up our friends new Rolls Royce Silver Shadow that night made a difference. The first and only time I have ridden in one but it was cool. So it was two firsts that for me that night mainstream crossdressing and the Rolls.
MAINSTREAM CROSSDRESSING TODAY
Fast forward to today and mainstream crossdressing is very common especially in big cities. Last weekend I met with 5 other CHIC members for dinner Friday night at a favorite place in Long Beach. We had two wives and 4 crossdressers for dinner and had a fun night eating inside for a change. I reserved a private room in the back of the restaurant which gave us a relaxing unhurried atmosphere to socialize in.
MAINSTREAM CROSSDRESSING WITH THE PUBLIC
I got a pleasant surprise when GG acquaintance came back to say hello after noticing me walk through the bar. I had just come in from going outside to take a picture for this article. She had not been around for a couple of years so it was good to know she was doing fine.
I intentionally blurred her face because I did not have her permission to put her picture online. I liked the picture of me so I included it.
This post was getting a little long so the rest of the weekend will follow shortly.
Crossdresser shopping is not new to me but although I have done it for many years I have never done it in Long Beach. San Francisco, Portland, Seattle, Las Vegas, Atlanta and Texas yes but, Long Beach no. I guess it goes back to my early years when crossdresser shopping was extremely rare. Crossdresser’s were not accepted and being asked to leave a store was a real possibility maybe by a policeman. Things are different now so I got to thinking about getting a pedicure. I used to do it all the time in San Francisco years ago and then go shopping.
Of course I wore my new mask a Christmas present from my wife and my lipstick was perfect.
I use the 4Ocean frame inside that keeps it from smearing my lipstick and it does look fabulous.
I made an appointment with a local nail shop for 1:30 pm Friday and got ready earlier than usual. There wasn’t time for a sit down lunch so it was Chicken McNuggets in the car then off to the nail shop. Turns out I was a bit early and the place was empty so they took me right away. I got in the chair and she went to work taking off my old polish then the pedicure.
CROSSDRESSING PEDICURE
I picked Marylin Monroe red and loved the way they looked. I wore black thong sandals so the polish would not smear inside closed toed shoes. They had a comfortable 2 1/2 inch heel. I was also going to the seamstress afterward for some alterations then some crossdresser shopping at Macy’s.
WELL DRESSED CROSSDRESSER
Next I was off to the seamstress to get some jackets taken in after losing a few pounds. Then I was off to Macy’s and the MAC counter inside for some crossdresser shopping to replace the eyebrow pencil that broke earlier. The MAC counter was empty so I was served right away got my pencil and left. I regretted it later because it was the perfect time to have the artist explain MACS new creamy powder foundation to me.
My crossdresser shopping adventure was very relaxed as Macy’s was not crowded so I was not rushed. That said I bought nothing again so my spending drought continues until the current trend passes. Tailored jackets are not trending now, active wear is so unless I want sweatshirt type styling I am out of luck. It might be related but fashion jewelry inventories seems to be shrinking possibly because nothing goes with sweatshirts and tennis shoes.
How I yearn for the days that Macy’s added 3 to 4 new tailored skirt suits to their website every Friday. Also leading up to Easter was a high heel extravaganza every year with feminine high heel sandals worthy of my pedicure.
Maybe this summer will bring some change to the fashion world hopefully more toward elegant VS sloppy.
Crossdressing clubs are still around and mine met last weekend in Long Beach California for our monthly meeting. We were just under 20 people with crossdresser wives making up about a third of the attendees. Those who commute a great distance typically stay at a local hotel for the weekend so we go out both Friday and Saturday nights. Under the current COVID restrictions it has been a challenge finding places to go but we manage. Our crossdressing club CHIC enjoys a very active membership with attendance at meetings being about 85 percent each month. With outside dining only in California (unless your the governor) jackets are becoming part of the wardrobe. Friday night I wore a hounds tooth skirt with a black V neck sweater. with the cool damp ocean air I needed the black leather jacket all night.
CROSSDRESSING CLUB FRIDAY NIGHT
CROSSDRESSING SATURDAY NIGHT
Saturday night wasn’t any warmer so I wore another leather jacket over my black and white dress. The dress was made of a light weight material so the jacket was a must.
CROSSDRESSING CLUB
There were 7 of us on Friday night two couples and three single where we ate at one of our favorite restaurants. We had a first when headed for the valet after dinner when we came upon another crossdresser on her way to dinner alone. We spoke with her and I naturally promoted our crossdresser club thinking she was eating alone. I am not sure if it was a coincidence or not but Saturday night she came to the same restaurant we were at. She got a table by herself when some of our girls spotted her and invited her to join our group. I did not want her to think she was being interrogated so I let others chat with her.
If she submits an application and is accepted she won’t have to go out alone anymore.
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.
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.
PRIVATE DINING
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.
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.
CROSSDRESSING PARTY
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.
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.
HALOWEEN 2018
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.
THE ELEVATOR
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.
CROSSDRESSING MARRIOTT
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.
Lucky me!
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.
GROWING UP
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.
GROWN UP
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.
Dining Out
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.
Shopping
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.
Compromises
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.
