My life as “crossdresser” 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 “sissy“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 “travesti” 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 “crossdressing” 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 “transgender” 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.
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Since then, I try to dress “crossdress” 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).
