Monday, May 9, 2016

Carollyn's First Time

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).

I invite all Femulate readers to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Source: Polo
Wearing Polo.

Harvey Korman
Harvey Korman (center) on television's The Carol Burnett Show (circa 1972).


  1. Funny that you had Harvey Korman on today, and yesterday's "Both Father and Mother" was the name of a show-within-a-show" in Americathon, where Korman had a brief drag scene.

    1. I was familiar with the "Both Mother and Father" bit in "Americathon," so that is where I swiped that from, but using Harvey's photo today was just a nice coincidence. (I wrote the Mother's Day post on Friday and the Monday post on Sunday. I assure you that by Sunday I had forgotten what I wrote on Friday!)