Year: 2016

My life as Carollyn Olson has been quite a satisfying ride.

Over the last three decades, Carollyn has figuratively flourished and matured, and developed so many great friends. I would not change a thing.

My story is a little different than many of yours. I did not start dressing until 35 years ago and it was very accidental. To make a long story short, I can blame it on the cat.

I was home working on my spouse’s dresser when she was out of town. Our cat decided to jump into a drawer and damaged two pair of nylons. I was going to show them to my spouse and let her throw them away, but for some reason I put them on. Before I knew it, I was dressed in her clothes, wig and shoes. Oh, what a feeling!

By the next weekend, when she was once again away from home, I had bought heels, two dresses, pantyhose, and had studied how my spouse applied her makeup. I completely dressed and went out for the first time. The first time I really looked in the mirror, I could not believe how good I looked.

Where did I go? I drove to the local mall, walked around a bit, went in to a couple of shops, had a bite to eat and sat on a bench to watch other women walk through the mall so I could study their mannerisms and how they walked and talked. Was I nervous? Yes, a bit, but not overly. I was “passing” and enjoying myself. When I look back at that first time today, I still wonder how I did it.

Since then, I try to dress two or three times a month. However, I have had to be careful with my dressing (my wife is unware of my hobby even though she has dressed me twice for Halloween parties).

Wearing Polo.