It was late summer when I noticed on Facebook that Pride day at the fair was coming. This is a big event for the city with tens of thousands attending. So for this gurl who isn’t afraid to go out dressed, this was a big step forward.  I met up with a friend and drove to the fairground, parked the car, and took a deep breath. In the past, there would have been a half hour or more contemplation—should I or shouldn’t I. It was the middle of summer and it would be daylight for hours, darkness being a crossdressers best friend. What if I run into someone I know? I wasn’t going to fret this time. It was freshen up my lipstick, straighten my wig, and off to the fair.

Across a busy street and up to the ticket booth, “Two adults please,” and we were through the turnstiles and into the crowd.  Was this real?  Am I dreaming? The fair that I’ve been to so many times before, and today, on one of the busiest days, I’m dressed in a very short sissy dress. How can this be? A few short years ago, I would not dream of going out dressed in daylight. On one of the longest days of the year, I’m at a fair with thousands of people with darkness hours away. Any level of comfort zone is long gone, but there I was and as confident as could be.

The first ride had to be the roller coaster, the busiest ride of all, and with a long line up. We walked right over.  There were a few people staring, but I stood there proudly in my dress, wearing a smile. The fifteen minute wait was over and we stepped into our cart. Click, click, click as the coaster was dragged up the rails. The thrill of the coaster and the sensation of wind flowing through my hair (well wig) and up the skirt of my dress were wonderful. We ran back to the line up to go again.

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A few more rides and we went off for dinner, and it was peak dinner hour. There were big line ups at all the vendors and crowds and crowds of people, yet the normal fear was replaced with confidence. We lined up and enjoyed our dinner, and then it was off to explore the fairgrounds. We wandered all over until we stumbled into a drag show on one of the stages. We spent the next hour dancing to the music with the show as we became part of the entertainment. Off to the carousel, and then the swing chairs (with the wind up my dress and a big smile on my face) we went.  We took in a few more rides before the midway and games of no chance. More laughs and smiles as we tried so hard to win a stuffed bear.

It was time for a snack, and the discovery that cotton candy and a wig are not friends. To the ladies’ room to freshen up and back to the rides for more spinning and turning until my head was spinning.  I am feeling ill, it is dark, and we had been at the fair for almost five hours.  Time to go home, or is it?  No! One more ride of the coaster before we pack it in. We walk to the car; I am exhausted but so happy to have spent the day at the fair in a dress.  The only regret I had was why I hadn’t done it years ago?

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Cross dressed most of my life.

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melissa la quinta
Trusted Member
melissa la quinta (@melissa-la-quinta)
8 months ago

You look so adorable, Nicki! XXOO

Active Member
Marianne (@marianne65)
8 months ago

Well done Nicki. A girl must have some fun at times.

Amy Myers
Trusted Member
Amy Myers (@amylove2dress)
8 months ago

Sounds like it was a great experience, and thank you for sharing it with us. Though I’ve been out many times, I’ve never done anything like that.

Dani Bryn Denali
Dani Bryn Denali (@heelssixnine)
8 months ago

Good for you Girly! How fun! You look adorbs!

Nikki Dahl
Nikki Dahl (@smoothbill)
8 months ago

You rock!! it must have felt incredible!! My “day” is coming up soon. I’m partipating in an event called Walk a Mile in Her Shoes. This will be my sixth year walking. This year I’m dressing for it. I’m going as Sandra Dee. A little nervous to say the least. There’s alot of guys that dress enfem. We even have several drag queens walking. Thank you for your article. You’ve given me a little more inspiration!!

Ashley Wayne
Ashley Wayne (@ashley92116)
8 months ago

Thank you, I really enjoy reading the posts, of members. It gives me hope that I’ll go out some day dressed up,
instead of the 3AM breakfast runs to the drive through. .

skippy1965 Cynthia
Trusted Member
skippy1965 Cynthia (@skippy1965)
8 months ago

Congrats Nicki !I love hearing about success stories like this!

patty williams
patty williams (@pattygurlcd)
8 months ago

Hi Nikki,
if that’s the outfit you wore to the fair I love it you look adorable.
How can someone so adorable be so courageous.
Thank you for the story and inspiration.
You are an amazing person

patty williams
patty williams (@pattygurlcd)
8 months ago
Reply to  Nicki

well I love your boldness and your dresses

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