Crossdressing with friends is something that I always look forward to. Especially because most all of them are members of my crossdressing club CHIC. Although the ages of members vary the common interests of crossdressing and wives bridge the age gap. Our August regular club meeting had a small turnout due to vacations and the same applied to the Friday night gathering. There were only three of us crossdressing with friends on Friday night, but it was really special. Natasha & Meridith joined me at one of our regular restaurants. What made it special was that although I have known them for many years we were always in a large group. With so many people participating in the conversation it limits what you really learn about people.
Friday nights crossdressing with friends Natasha and Meridith gave me an opportunity to learn more about them on a personal level. Knowing the restaurant owner pays off because they gave us a great table in the bar area and did not rush us. Besides comparing notes on our crossdressing evolution and other personal experiences growing up were shared. It always fascinates me when you reach the level of trust with crossdresser friends that you feel comfortable sharing your personal life. Sometimes I am very surprised at people’s backgrounds and experiences because I only knew them from crossdressing. That does not give you any indication of who they are the other 29 days of the month.
Crossdressing with friends who present very well in public does not give any clue about their life away from crossdressing. I won’t divulge Natasha’s details but others I have known had very interesting stories. Over the years I have been crossdrerssing with friends who were airline pilots, military officers, surgeons, lawyers, television actors, radio show hosts, policemen, firefighters, scientists, Engineers, construction workers, and teachers just to name a few. What’s remarkable is how similar each of our stories are regardless of where you lived as a child.
This personal interaction with crossdressing friends is what makes belonging to a club so rewarding for myself and the other members. Many of the friendships in CHIC have lasted decades.
Crossdresser perceptions go both ways which is to say how we perceive those we interact with along with how they in turn perceive us. The Friday before our monthly CHIC meeting I went to dinner with my BFF Ashley at a restaurant in Orange County California. Historically we have avoided it for many years because Orange County was a pretty conservative area and we felt uncomfortable going there. We did not really know what the crossdresser perceptions would be with the mainstream clientele conservative or not. We went once before in November, and it went well so we did it again this month.
I arrived by myself via UBER very early and was cheerfully greeted by the hostesses using all the proper pronouns. That is notable in that I always use my male voice when dressed. The hostesses took it all in stride and continued calling me Mam. They offered to seat me early in the area that I had requested on my reservation, but I declined. I sat in the chair pictured lower right side above on a busy Friday night. I got to see the public’s crossdresser perceptions of me. Those who reacted were positive and those who didn’t seemed indifferent going about their business. It’s safe to say everybody notices me because I dress for myself so its way different from casual California lifestyle.
Not many women wear a black velvet suit with an embroidered flower on the jacket and high heels on a Friday night. I think their crossdresser perceptions of me was positive regardless of if they approve. I got several compliments on my outfit from women I encountered. Our server was very attentive without being a bother and did not rush us to order or leave after dinner.
Saturday night was the CHIC meeting at one of our regular places in Long Beach and we had a private room, so crossdresser perceptions weren’t possible. I have been there so many times I don’t even think about it because its predictable. The crowd is getting younger as time goes on and they are typically more accepting of crossdressers. Should they have any questions the restaurant owner and his staff know all of us very well and can fill them in on our story. I requested outside dinning because some in our group are very concerned with the Omicron. They moved us inside to a private room. The high for the day was 61 and the low expected in mid 40’s which in Long Beach. That can be very cold being just blocks from the ocean.
The picture above was taken in the lounge section of the room we were in Saturday night. My wife has been encouraging me to stop wearing so much black, so I wore brown tones this month.
Crossdressing in public has come a long way over the years and the perception of us has changed to a far more positive one. The other ladies and I of CHIC always try to present the best possible image when out in public for positive crossdresser perceptions.
Crossdressing adventure in the late 1990’s were becoming more frequent for me once I joined the crossdressing club CHIC. Some of the meetings/parties were at members’ homes and were very popular with almost all members attending. CHIC member wives came to the home party’s because they were considered safer than going to public restaurants. One of the wives’ fears was that if someone recognized her, they would soon notice who she was with outing the husband. My wife had no interest in attending my crossdressing adventure in the beginning but was fine with me going. She only requested that I stay the night in a hotel as close to the party as possible. I agreed and found hotels close by that were secure and allowed me to go in and out with minimal exposure to the public.
CROSSDRESSING ADVENTURE HOTEL
Finding a Residence Inn by Marriott near Jo Ann’s house where many of the parties were held. Especially pool parties in the summer. It was pretty much surrounded by commercial Monday thru Friday businesses that closed on Saturday. A freeway behind so the only people around on weekends were at the other hotels on the same street. The Marriott was at the end of the street and had one building in the back by the freeway separated from the main facility. It was usually empty because they filled from front to back of the hotel by the pool and other amenities. PERFECT!!!!! I always requested a ground floor room in that building so I did not get complaints about walking late at night in high heels. I backed the car in so it was a short walk so I could leave quickly if I encountered someone. It was a favorite spot for a couple of years and worked out perfect. I could even get an early check in because they were not busy on weekends giving me much needed time to get ready.
CROSSDRESSING ADVENTURE POLICE
Then I had a crossdressing adventure like never before. After a fun night with friends at Jo Ann’s house at a January meeting thing wound down and I said my goodbyes. Taking the least traveled route back to the hotel it was time to turn left onto the street my hotel was on. To my surprise the street was full of police with lights flashing and people sitting on the curb in handcuffs.
ABORT!
ABORT!
ABORT!
Flashed through my mind while I continued straight down the road without turning. Possible alternatives flashed through my mind but were quickly dismissed because there was still only one way into the hotel. The only feasible alternative was to go into the industrial complex the other side of the fence from my room. It would require me to scale a small fence in a dress and high heels. Police noticing a woman climbing a fence in an industrial park at midnight on a Saturday night. Not the kind of good crossdressing adventure I would enjoy!
Not thinking I could pull that one off I thought maybe I could just drive through the police area. I thought possibly they would just wave this nice lady on her way. Wondering what would happen if they stopped me to inquire where I was headed down a dead-end street. Albeit at midnight on a Saturday night. Thinking this was not the time to create a believable female voice I had never practiced. Especially given the fact I had been drinking that night I dismissed it also.
CROSSDRESSING ADVENTURE DRIVING
I thought about just driving up making no attempt to fool anyone show my room key and hope they would let me through. Today not so much a problem but in the the late 1990’s they might be very curious what I was up to and ask lots of questions, so I dismissed that one also. I was not good at getting ready in those days and had girly stuff all over the room. If they escorted me to my room, I was sure they would think it was a violent crime scene. So, on I drove for hours making loops down this freeway to another then another for my longest crossdressing adventure of my life. Then circling back to the hotel.
Cops were still there every time and I remember thinking that Al Capone was convicted and sentenced in less time than this. I even thought about calling in a bomb scare momentarily figuring they would have leave and go to it. But then I thought they might only send half the cops so I would still have my problem. All this on top of the fact that I had to pee in a big way.
Finally, after about 2 hours I returned and found the street empty and drove to my room. Then immediately went to the bathroom and almost passed out from relief then cleaned up and went to bed. I only slept for about 5 hours and got up. I cleaned up the crime scene packed and went home. Once home I got to explain to my wife the reason, I was so tired. Because I was up late dealing with a police crossdressing adventure.
Kinda true right?
She had a good laugh and asked why I didn’t just explain everything to them.
Thank God for UBER I wish they had them back then.
I use UBER now everywhere I go when dressed and have not had any crossdressing adventures like this one since.
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.
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 you’re the governor) jackets are becoming part of the wardrobe. Friday night I wore a hound’s 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 lightweight material so the jacket was a must.
CROSSDRESSING CLUB
There were 7 of us from our crossdressing clubs Friday night two couples and three singles 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 wigs are probably the most important item purchased by men seeking to look like a woman. Selecting the right one for you will make a world of difference when you are out and about in public. It’s not that the correct wig will make you passable it’s that without it you will stand out from the crowd. Even if you pass people will still notice and say BAD WIG!
A good crossdressing wig will compliment your face and many times your overall look. If you are older and have pronounced wrinkles and saggy skin straight wigs can accentuate them. If you are light skinned and wear a dark colored straight wig it will make them more pronounced. Shorter crossdressing wigs are probably the most important item purchased by men seeking to look like a woman. Selecting the right one for you will make a world of difference when you are out and about in public. It’s not that the correct wig will make you passable it’s that without it you will stand out from the crowd. Crossdressing wigs within lighter colors with waves, curls, or feathered styles are more complimentary for older ladies. I fought it for decades but finally made the change once I found the style for me.
WIG STORES
Trust me on this one you won’t be the first crossdresser to call a wig store and make an appointment. When buying your wig, it is best to go in dressed as a woman if your makeup is correct. The wig and makeup should be compatible so they will work together making you look your best. If you’re not confident in your makeup go to the appointment as a guy without it. Because at least the wig stylist will be able to see your natural skin tone. They will also help you select the most complimentary wig style for your face shape which is important. Then once you get your makeup correct for your skin tone the crossdressing wigs will work.
If Diva Las Vegas happens this year 10/27 to 11/1 you can accomplish crossdressing wigs and makeup in Las Vegas a lot less awkwardly. The Diva people help with appointments at local stores for those attending the event.
I currently own about 12 crossdressing wigs after giving away about 20 to a women’s cancer charity a couple of years ago. All are in shades that compliment my skin tones and are shorter with one exception. They are all from Godiva’s Secret Wigs and are their own line of wigs. I like the quality, colors, style along with the short time it takes me to style them. I am wearing on called Trixie in the picture below right. The wig was just washed, shaken, then styled with my fingernails.
WHAT STYLE?
The picture also is a good illustration for a crossdressers wigs selection because of the three different people and styles. Tonya on the left prefers shorter wigs piled high with curls and the dark brown color goes well with her skin tones. Erica in the center is wearing a straight black style and the color matches her natural hair color complimenting her skin tone. Erica got it right where others get it wrong because her long straight style has height and is parted on the side.
WIG STYLING
The #1 mistake I see all the time with this style is crossdresser’s pull a new wig out of the box and plop it on their head then walk out the door. Out of the box the wig is flat as a pancake and typically parted down the middle. Always give the wig a couple of hard shakes when you take a new wig out of the box. After that gently brush it from front to back a couple of times. You can also use a comb to lift the Perma tease that is located at the base of the hair.
CROSSDRESSING WIGS HELP
I recommend watching this video from TAZSWIGCLOSET which is where I get a lot of good wig info. She goes through the whole process of opening a new wig. One difference between her and other wig experts I have seen is she wears one every day, so she is a bit more passionate about wigs I feel.
Pictured on the right is me in my Trixie wig. I moved the part to one side which is against the grain (Perma tease) so to speak making the hair stand higher. It also gives a softer look with the hair separating on top. I washed the wig last week letting it dry in the shower then when dry turned it inside out. Placed it in a plastic bag inside one of my purses in the suitcase. I pulled it out in the hotel room, shook it 3 times the combed it from front to back a couple of times then put it on. Then adjusted the part then styled with my nails adding a light spray to keep the part in place and I was off to dinner.
Take your time when choosing crossdresser wigs and get it right the first time.
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.
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 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.
This event has pretty much 100 percent attendance for CHIC members and wives. Our party is in the wine cellar private dining 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 for crossdressing Christmas unless something comes up for New Year’s 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.
