Crossdressing adventures in the late 1990’s were becoming more frequent for me once I joined the crossdressing club CHIC. Some of the meetings/party’s 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 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 party’s were held. Especially pool party’s in the summer. It was pretty much surrounded buy 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 things 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 good!
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 seen. So on I drove for hours making loops down this freeway to another then another. Then circling back to the hotel.
Cop’s 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 that the reason I was so tired. Because I was up late dealing with the cops!
Kinda true right?
She had a good laugh and asked what I didn’t just explain everything to them.
Thank God for UBER I wish they had them back then.
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.
Being a traveling T Girl road trips are something that most of us do to at one time or another. Some often like myself others only occasionally but we all have the same challenge. What to take and how to get it there in addition to how to pack it all. If driving, you can take everything you own depending the size of your vehicle but flying takes some planning. My wife organized my packing process years ago and I have used her system for years with great success.
WHAT TO BRING
My traveling T Girl road trip starts with planning my evenings out differentiating between casual and dressy nights. Once I decide on an outfit for a night, I lay it on the bed and pick out some jewelry to go with it.
ACCESSORIES CAN MAKE OR BREAK THE OUTFIT
Setting the jewelry on the garment gives me an idea how it will look when worn with the clothing. Then I hang it on a door nob or cabinet nob so I can lay the purse and heels I choose below it.
ACCESSORIES
Once I am happy with the nights look the jewelry goes in a zip lock sandwich bag and hung on the hanger by punching a small hole just below the zipper.
I do this for every night I will be going out along with days outfits. Daytime outfits are far easier to put together because the emphasis is on casual as opposed to the night time glamour. Makeup is toned down also as not to stand out so much in the crowd. Shopping rules the days so jeans and flats come first followed by a thin top so I can try clothes on over it. My preference weather permitting is a light jacket with a zipper in front. That way I don’t have to take my wig or blouse off before trying things on. Jewelry is conservative also with smaller earrings and bracelets. My wig for daytime will be light brown as opposed to flashy blonde shades. Again, the jewelry will go in a zip lock over the hanger.
When all the outfits are selected, I put a clear trash bag over the hanger of each outfit to guard against wrinkles.
TRAVELING T GIRLS
Packing wigs depends on the wig short or long full or straight. I have used cases which take up lots of room but protect the styling and they are great if you are driving. Flying traveling Tgirls are another story due to luggage limitations on size, weight and quantity of suitcases. I have used a trick for traveling crossdressers taught to me years ago by the late JoAnne Roberts for longer and full hairstyles. You place the wig in a plastic bag folding the excess bag under the wig and insert it into a plastic she box. Takes up very little room in the suitcase and preserves the styling well.
You can take collapsible wigs stands with you or you can buy large pop bottles to use for wig stands when you arrive at your destination.
Milano 2 piece wig stands slide together with offset slots in each of the halves
My wigs are all short and can be packed inside out then shaken upside down. I can style them quickly and I bring portable collapsible wig stands. I just purchased two new stands pictured above that I will be trying out but think they are going to be great as they are very compact.
Fake fingernails are a must for crossdressers and they can easily be bought on line or in most drug stores. Size can be a problem as they are designed for women who have much smaller nails. Some of the prepackaged nails will fit but thumbs usually don’t. My solution is to but unpainted nails in my size form Talon Nails and shape them myself.
FRENCH MANICURE
A couple of years ago I started experimenting with doing nails in a French Manicure style. It takes more work than just cutting, shaping and painting fake nails but is worth the effort.
The process is the same as the one detailed on my CROSSDRESSER FAKE FINGERNAILS page. The big difference is when you paint the fake nails it will be with a French Manicure polish designed to look like your natural nails.
On the nails above I painted 3 coats of the polish on the right using my nail wheel.
I let the Polish dry overnight and then mask off the section of the nail I will paint white the next day.
Because I will be using an airbrush to paint the tips I need to mask off the back part of the nail. The masking strips are available at most any beauty supply or of course Amazon.
Now its time to fire up the compressor and get to work on the tips. I use the white tip paint mixed with nail polish thinner 50/50 so it will spray easier. I tried brushing the white tips on but, it was always too think. The fake nails did not look natural like you see women wearing on the street.
I let the paint dry overnight and then remove the masking the next day.
After letting the dry another 24 hours I put two coats of Orly topcoat on and i am all done.
I bought my airbrush equipment from Amazon and the compressor from Harbor Freight.
Mature crossdresser’s are seen more and more out among the mainstream public. The Friday night before our monthly CHIC meeting affords an opportunity for some members to go out 2 nights in a row. Some travel a great distance to attend meetings and like myself get a hotel room for the weekend. Wanda and some others joined joined me for the January Friday B4. She and I are in the lounge of one of our favorite restaurants in Long Beach. The only crossdresser wife attending that night was Wanda’s who took the picture.
SEASONED CROSSDRESSING
The member ship of CHIC ranges from 42 to 93 the average being about 60. We are a fun group who look forward to our monthly get together’s. The knowledge attained over decades is willingly passed along to the younger members if they are receptive.
MATURE CROSSDRESSER’S WITH STYLE
Micki Finn
I like many mature crossdresser’s prefer to dress on the conservative side without being dowdy or fuddy duddy! I love this jacket and skirt combo that I purchased separately and paired together. The look is timeless which is my goal when ever I purchase something. Only dressing a couple of days per month means if I buy something trendy I may only get to wear it once before it goes out of fashion.
MATURE CROSSDRESSER’S POSITIVE IMAGE
I have some shorter skirts slightly above the knee but mostly prefer the hem mid knee. They will always be in style if not fashion and don’t send the wrong message to those I encounter while out and about. The last thing I want is to give the impression that I am available to some boozed up dude looking for action. I always wear the wedding rings my wife bought me in case anyone looks but that doesn’t always deter people.
When I am approached in public it is typically from women curious about my being dressed as a woman. Some notice my ring and inquire whether I am married to a man and some are shocked to find I am heterosexual and married to a woman. I have enjoyed many enlightening conversations with these women and even their husbands on occasion. I am sure the conversations would not happen if I was dressed in a manner that made them uncomfortable.
This years CHIC crossdresser Christmas Party we had 20 attending and it was a joy watching each one descend down the staircase in their beautiful dresses and gowns.
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.
COLOR CONSULTATION
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.
Micki Finn crossdressed in red jacket.
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.
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.
