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Cleveland, Four Special Days – Part 1

How lucky am I?

By the lovely Jocelyn Johnson

I’m a transgender woman. No matter what clothing I am wearing doesn’t change that fact. I am somewhere along the spectrum between male and female.

My home situation does not allow me to physically express the female side very often. But when I get the chance I fully embrace it.

I live in Ontario, and when given the chance in the winter to spend a few weeks in Florida golfing, I organize a trip for myself. I find driving the 2,300 km (1,430 miles) one way, is more enjoyable and cheaper than flying. It also gives me the opportunity to stop in Cleveland on the way down and also on the way back home. Last year I spent one night in Cleveland going and returning. This year, January 2024 it was three nights in Cleveland. And we all know what the big draw is there; Kandi and Sherry.

It had been over five months since I expressed my feminine side through clothes. The need and urge was very strong. I believe all of us CD/TGs experience a special, exhilarating feeling while dressing and presenting ourselves out in the world. During the five month interruption I had nearly forgotten the absolute joy of looking beautiful.

I had purchased two new tops and skirts, plus a pair of shoes for the trip.

My first evening in Cleveland, Kandi and I met for dinner. As I was preparing to go, getting dressed and putting on makeup, my mind, heart and soul experienced the sheer ecstasy of slipping on stockings, skirt, blush, lipstick and shoes, plus all the other appropriate things.

As I looked in the full length mirror before I headed out, I felt completely natural; so comfortable in my appearance; so feminine; so beautiful.

The hours I spent with Kandi during dinner were marvelous. Old friends catching up on our lives. The depths of our sharing is remarkable. I am so blessed to have her as a very close friend. Of course Kandi’s appearance was perfection [Editorial comment: I looked like my head was a concrete block, as we all have already seen here.]

We received compliments from the restaurant’s staff and photos were taken.

It all ended with a big hug and plans for the next day. Part 2 coming soon.

Love to everyone,



6 Responses

  1. Jocelyn, that’s quite a road trip – I just looked on the map and if I set out to drive that sort of distance, I’d end up 100 miles or so away from Moscow!

    Anyway, glad to hear that your trip was such a success and you were able to spend time with Kandi (and Kandi, I’m not sure what concrete blocks are like in the USA but you’re far better looking than the ones we have in the UK!). Great outfit too – I’m not surprised you felt so good and comfortable!

    1. Thank you so much Amanda for the compliment.

      If and when you do the drive towards Moscow, I hope there is someone as wonderful as Kandi to greet you.

      Kandi’s editorial comment is amusing. As I said last week in a comment during Kandi’s post on February 7, 2024, being seen side-by-side with Kandi is not always a good thing. Kandi is so beautiful and well dressed, it makes her companion look somewhat diminished. Which is OK with me. Her wonderful conversation is rewarding.

      I just love wearing a skirt and other feminine attire and going out for dinner.


  2. Jocelyn,
    Gosh five months is waaay too long , so good you finally brokeout and looking good for all that waiting .

    In the Uk we just don’t appreciate distances as Amanda comments but I do recall a group of us were in Utah and drove 400 miles for breakfast , according to the locals it was just down the road !!

    Even being full time I still get a sort of buzz when driving and looking down seeing the hem of a skirt and my legs in stockings .

  3. Teresa,
    Let me tell you, that it is certainly worth the drive to Cleveland and then on to Florida. The driving was good and everyone I met was kind.

    You are very correct; looking down while in the car and seeing your legs in stockings and the hem of your skirt above the knees is exhilarating.

    Thank you for the kind words. I wish outings were every day, but my home situation prevents that. I’m OK with it.


  4. Jocelyn: I like your outfit. I have a very similar necklace. It certainly is a long drive. Check out the autotrain from Lorton, VA to Sanford. I have used it twice. Look forward to your other posts. I am here in FL until mid-March but back again by myself (Yea!!) for two weeks in late April. I would be interested in any experiences you had while dressed in Florida. Have fun golfing–I just started playing pickleball here and it’s a blast.

    1. Donna,
      Thank you for the compliment. I love wearing a skirt. The necklace adds a little “bling”.

      I have a post coming out, probably the first part of March about my visit with Lee. She lives on the east coast of Florida.

      I hear pickle ball is a good workout. Keep playing it.

      Florida has so many wonderful people.

      Take care and enjoy the warmth.


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