Elaine’s Best Day Ever

In the movie “City Slickers” the character played by Billy Crystal asked his friends to talk about their best day ever (other than the birth of their children). So, this is the story of my best day ever as a crossdresser.

A few months ago, through the wonders of social media, I reconnected with a girlfriend from 30+ years ago. As we were catching up, I told her I was a crossdresser, relayed some of my experiences, and shared pictures of me en femme. She seemed very accepting, as I thought she would be. A short time ago, she told me she and her sister were escaping winter weather for a couple of weeks and would vacation at a tourist/beach town about two hours away from where I live.

The sister had once studied to be a beautician and offered to do a makeover if I would come visit them. Two thoughts instantly and simultaneously flashed thru my brain: I would really like to do that, and I should not stay at the same motel for a couple of days with a former girlfriend without my wife. I asked her if she would like to join me, and she said yes. You should know (to fully appreciate her agreement) that she does not like me to dress en femme, and strongly objects to me even opening the front door when en femme to say nothing about going out. This was an enormous step for her. I packed my makeup bag and off we went.

After introductions, small talk, and dinner, the sister offered to do facials on all of us. I’ve never had that done before! What a terrific feeling. She also painted my nails for the following day’s events. We talked well into the night. I was very pleased with how everyone got along and our easy conversations about crossdressing (in general,) and me specifically, flowed. The next morning, I arose early and dressed totally en femme. We all met for breakfast and decided on shopping at some of the local thrift shops, then return mid-afternoon for makeovers, followed by dinner at a nice restaurant.

The weather was chilly that day, so dressed in my skort and ladies’ sleeveless golf shirt, I was underdressed. Clearly, I needed some ladies’ blue jeans, which we found at a shop early on. My first pair of lady jeans. “They look really good on you!” I overheard one lady say. We stopped at several more thrift stores where the object was to find lady clothes for me. It made me feel so special. Once back at the motel, her sister loaned me some of her sundresses to try on to judge size and style. Then the makeover session. It was every bit as grand as I had hoped for. She explained concepts, style, colors, brushes, products, methods, tricks, and more.

I was so pleased. That evening – although we had planned to venture into the city to do touristy things – it was too cold, so we settled for an early dinner at a seafood restaurant. The only time I had a desire to be in men’s clothing was during dinner–I wanted to attack the fish and chips like a man in a feeding frenzy.

It was a wonderful experience: I got to dress all day; had a terrific girl’s day out with a special friend; met a new friend; got a makeover, facial, and nails; didn’t hear a single snide remark or even see an odd stare anywhere around town, and did it all in the company of my wife. Bless her heart! My best crossdresser day ever!

More Articles by Elaine

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