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.

En Femme Style

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!

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    Elaine

    70 y/o male crossdresser. Been dressing in private for years. Came out to my wife about 15 years into the marriage. She's is accepting but not supportive.

    Latest posts by Elaine (see all)

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    Laurie Tidenow
    Member
    6 months ago

    What a significant step forward with your spouse! My “D” is in quite a panic whenever Laurie wants to step outside to our very private patio. I would be thrilled to have her take the two of us for a short vacation stay – say in Las Vegas or another accepting venue. Over the years her participation has somewhat lessened and now it is more like “oh THAT again today”! I never hear negative comments but the “why don’t you go set pretty” has become a thing of the past. I’ve become so comfortable in casual feminine attire that the… Read more »

    Pamjoe Rowo
    Pamjoe Rowo
    6 months ago

    Hello.i am very new on here.i like what i see at the moment.but if i want to delete my acccount how do i do it.i do love chatting.and i got so much to tell .and so much i want to know.so please come and say hi.

    Kristen Smithly
    Active Member
    6 months ago
    Reply to  Pamjoe Rowo

    I am not sure how you would delete your account, I suppose contact one of the administrators, but I have to tell I sure wouldn’t! It’s a wonderful, safe secure place for us, and Welcome!

    Haley Ann
    Member
    Haley Ann
    6 months ago

    Very cool!

    Trish White
    Baroness
    Active Member
    6 months ago

    Wow, that is so awesome Elaine, I’m sooo happy for you. I’m jealous too, I can only dream of my wife saying that to me. Have a great time and fill us in when you’re back.

    cheers,
    Trish

    Trish White
    Baroness
    Active Member
    6 months ago
    Reply to  Elaine

    I’m glad to hear that Elaine, sooo happy for you.

    Love,
    Trish

    Patricia Marie Allen
    Active Member
    5 months ago

    Love your story. It shows you are a very responsible person and I’m sure your wife saw that when you asked her to go with you rather than go on your own. It’s quite possible that was the tipping point that got her to agree. Like your wife, mine isn’t exactly thrilled by my feminine nature being expressed. She’s learned to endure it when I go out dressed and not get uptight when I venture into the city on a regular basis in unmistakable women’s clothes. On the other hand, while she knows that everything I own is off the… Read more »

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