I went to a lovely party last Saturday night hosted by two of my fellow CHIC members in their new home. Their home overlooks the ocean but it was about 40 miles from where I was staying for the weekend. I decided to rent a hotel room close by rather than drive back to where I was staying. Several things contributed to my decision besides drinking at the party. I was wearing a red blazer and high heels which would not help my field sobriety test although I would look great.
The big decision was do I get ready then drive to the party dressed or pack everything I need and get ready at the hotel? Knowing it was a virtual certainty that I would leave at least one crucial item behind I opted to get ready then drive to the party. Where the “You’ve come a long way baby” comes in is that I did it in broad daylight. Twenty years or so back I would never have considered it but, my confidence has steadily grown over the years.
I wore a black knit skirt with a black vee neck tank under a red one button blazer. Black patent 3 1/2 inch pumps and nude stockings with an over sized black patent purse. I also wore by Godiva’s Secret short blonde wig with roots. Most CHIC members attending wore red dresses along with the hosts. After checking the bag of guy stuff I was taking for the morning after the party 30 times to make sure I had everything I was off. I strutted through lobby of hotel #1 around 4:00pm waving at the desk clerks as my heels clicked on the floor.
The drive down went great toll booths and all and now it was time for another decision. Do I check in to hotel #2 first then go to the party of wait until after the party. Even though my confidence is at an all time high checking in around eleven thinned out the guests in the lobby and made more sense.
After the party I headed for the hotel found a parking place and walked to the front door. I had to stand there waiting for a minute or so because you need either a room key or wait to be buzzed in. They opened the door and welcomed me in saying hello mam can I help you. I replied yes and gave them the name the reservation was under along with a credit card in a fem name. He then asked for me ID and I complied giving him my real driver license. He glanced at them both then returned them saying “sign here sir”. I thought about correcting him but I thought it was so funny that he switched pronouns without missing a beat.
The next morning I showered and left as Duke meeting up with two other CHIC members for a round of golf as guys. I think the hotel staff is still looking for the attractive blonde to come down stairs.
Makeup is the number one area of interest to crossdresser’s whether they are just starting out or have been at it for a while. I am not a big fan of trying to pass because I don’t think it is achievable for most of us. One thing is for sure though without it you have no chance of passing. After a bit of work I have updated the Crossdresser Makeup page with more detailed instruction and new pictures. I hope the illustrations and procedure make sense to you. I am attempting to give the reader more of a step by step tutorial along with product pictures.
My procedure has sped up my makeup time considerably by simplifying the process. It emphasizes doing the areas that are the most difficult first. The eyes have the most detail with multiple different products and techniques applied in a confined area. Doing them first allows you to make corrections without screwing up your foundation or contouring.
I just returned from a trip to one of my most favorite cities San Francisco with my BFF Ashley. We both crossdressed and met up with two of my Vanity Club crossdresser sisters Kelli and Diane. Diane lives in town but Kelli drove some distance to meet us at our hotel for drinks.
We Uber’d up then we went for dinner at Waterbar Restaurant. Water Bar specializes in seafood and it is the best along with the service. We got an awesome table next to the window with views of the harbor and Bay Bridge. The ambiance is wonderful with large 2 story column aquariums filled with large salt water fish.
This picture with my new short wig was taken in the Warwick Regis Hotel lobby while waiting for the other girls to meet me in the bar for cocktails.
I don’t do crossdressed pictures too often but, this one taken in the hotel lobby with the bar in the background. San Francisco is a special place so I make an exception while there.
I bought the Moto jacket this last summer but had the skirt already and fortunately the zippers matched. San Francisco is the most friendly place to crossdress in my experience anyway. I am crossdressed the entire time that I am there usually and shop to my hearts content.
Shopping while crossdressed is no big deal with Macy’s and the other stores in Union Square. I would recommend wearing flats though because the hills are killer for heels.
For years my wife and others suggested my wearing a short wig for various reasons. I know many CD’s that wear short wigs but never liked them for me.
A few years back I purchased short wig from a wig ostensibly for my wife. The woman dutifully sold me the one I liked in the wrong size and color for me but, then again it was for my wife right? I took it home, tried it on and scared the hell out of myself.
Had I been honest with the sales person and told her I was a CD she might have suggested something else. Maybe she would have told me that a jet black page boy would show every wrinkle in my pale skin. She might have told me it was too small making me look like a gear shift knob.
Do it right
She would have measured my head for the correct size and chosen a color to compliment my skin tone. She might have talked me into a short wig properly sized and shaped for my head. I was too embarrassed to tell her it was for me back then so I did it the hard way. Also the wig was parted down the middle so the hair covered part of my eyes and the curved ends kept falling in my mouth. I tried again some years later with a color that was better but the style looked like a football helmet on me.
Fast forward 30 years and I found one that I liked so I bought another one in a different color. The style is Freedom by Godiva’s Secret Wigs located in Southern California but they have a website. I am now a confirmed CD wearing a short wig all the time.
What I like about the wig besides the cut is it comes in a large size (23 inch diameter) the length I need. The nape down the back is is about 2.5 inches and there is enough hair on top to style it high. Increased height adds length to my face and gives the appearance of narrowing it. The wig is also their own brand and very good quality. It is the only brand that they sell.
I have been wearing high heels for many years and pretty much putting up with the pain. The toes are smashed together in a triangle like the bow of a boat. My toes are bent upward until I walk a few feet barefoot.
A couple of years ago I discovered Vivian Lou Insoles for high heels which, are shown in the picture below.
The clear gel pad going from the arch to just shy of the heel back shifts your weight back. It moves your weight from the ball of your foot to the heel. It more evenly distributes your weight over the whole foot.
Ice them up
Vivian Lou insoles help a great deal but the old ice trick makes high heels even more comfortable. A couple of years ago I wrote about this technique on my other site www.chicladies.org. Recently I made a discovery that makes it even better. I was getting ready to go to a Vanity Club outing in Atalanta and had two new pairs of high heel pumps to wear.
I inserted the zip lock plastic bags with the corner deep into the toe of each shoe pushing it in with my finger. Make sure that the corner is all the way in. Filled the bags about a third of the way full with water and put them in the freezer over night.
I did this three times on one shoe but the other needed a fourth time. I put them on in between to check the fit. When the water froze each night it expanded gently stretching the shoe a little each time. The high heels pictured above are satin but the ones I did multiple times were black kid and black patent leather.
Staying in hotels has its advantages like room and maid service but some drawbacks also. Typically I leave the room in the morning as Duke doing guy stuff returning around 3:00pm to become Micki.
When I leave the room at around 6:00pm as Micki with my heels clicking down the hall hair and makeup perfect I definitely look different. It used to bother me a great deal that the maids would see my wig stands on the dresser which, is the only hint that Duke and Micki are sharing a room. I was worried they might tell other staff and snicker about a crossdresser in the room when they saw me as Duke but not so much any more.
I discovered these hangers on Amazon and tried them out on my last trip.
They go together quickly and disassemble quickly storing flat for shipping.
Maids don’t go into closets or open drawers so the wigs are out of site hanging in the closet. Wives traveling with crossdressers will appreciate the privacy also.
This post is a first for me in an attempt to review a book now online and in book stores. I found Caitlyn Jenner’s book authentic and believable but, am concerned about people generalizing who she is versus crossdresser’s. In my case a heterosexual crossdresser who dresses a couple of times per month. Married with children, grand children and all that. I know Caitlyn Jenner has many children but you need to read the book to learn about that.
The book gives a fascinating look into what goes on in someones mind versus their outward appearance. I remember in 1976 when Bruce Jenner won the Decathlon he was America’s hero and made his country proud. I am sure I am not alone in envying his looks and his life, the guy was a stud. Most guys were sure he was bedding different women 7 days a week especially when he went to Hollywood. Caitlyn sets the record straight with a very different account.The book has many other surprises based on my and other peoples assumptions about Bruce Jenner.
We are the same age and grew up in the post WWII era but on different coasts. Being a crossdresser in those days was a very lonely existence because there was really nothing readily available on the topic. It was never discussed in school or church and nobody spoke of it. We were totally alone with our thoughts and desires. I never heard the term DRAG QUEEN until I was 22 which, was about the time I read something about a Transvestite in a magazine.
She explains in the book pretty much what we all went through as most crossdresser’s. Starting at an early age with Mom’s stuff and in her case an older sister in her teenage years. The guilt, shame and self loathing she describes are a familiar story for many of us. We were raised by men who fought in WWII just a few years before and survived it’s horrors. They were tough and expected the same of those they fathered, coached and mentored teaching us to be men. We could never bear their disgust and being thought of as a sissy. It is one thing to self loath but quit another to experience being loathed by someone you loved and respected.
Crosdresser no more
Caitlin’s Jenner’s decision to start her transition to become the woman she feels she needed to be is where the similarity ends. Although much of what Bruce Jenner did through the years parallels most crossdressers experience the decision to become CailtlynJenner is where it ends. Most crossdressers don’t have desires like hers and are content to manage their urges to dress like women.
I hope that people understand the difference between the two groups especially loved ones of crossdrerssers such as wives, children, girlfriends, parents and friends. Crossdressing does not necessarily lead to a sex change. The majority of cross dresser’s live normal lives indulging their desire to dress in women’s clothing part time.
I recommend the Caitlyn Jenner book to anyone interested in crossdressing or sex reassignment surgery. It is a well written interesting story and enjoyable read especially if you think she is trying to be the spokesperson for all trans people. She takes some heat on that label given to her by the media.