Carollyn's Other Times

This is part 2 of "Carollyn's First Time," which I posted here on Monday.

Skipping to October 2004...

My real life as Carollyn started on the 17th of October. My wife and family went to Disneyland while I had to stay at home. For six days, it was feminine bliss. By that time, I settled on my name, my overall look and style.

That week, other than work, I lived as a woman. It was wonderful. I went to movies, dinner, shopping, the casino and did many other "girlish" things. I was never harassed and was always accepted as a woman.

I had been using my wife's short wig, as my second-hand wig was "big hair" and I wanted a change. I visited a nearby salon where I had purchased my first wig. The ladies at the store were so helpful, especially Linda. She took my "big hair" and trimmed it into something more stylish.

I had first gone to the shop in male persona, but the girls insisted I come back dressed when I picked up the new hair. Unfortunately, the day we set for my return, my wife had to cancel her plans, so I would not have an opportunity to dress. I phoned the ladies at the shop and told them of my dilemma and they insisted that I dress there. So I did, and spent four hours with the ladies in my new hair while learning etiquette from one of the ladies who was a former model. I felt I was all set until a few months later.

The following May, I had the luxury of making a trip to I Love It Girl (ILIG) in Fremont, California. ILIG was a TG paradise with tons of clothes, wigs, shoes, etc., and a lovely and helpful owner in JoAnn. I was on a business trip to the San Francisco Bay Area and decided to visit on a non-social night. (ILIG has Wednesday night socials every week).

When I arrived, JoAnn was busy, but greeted me with open arms. I was dressed in a red skirt outfit and matching heels and she gave me so many compliments while she worked with another client. After a short time, she sat me down and chatted about dressing and then without asking my size, pulled out a number of different dresses for me to wear for pictures. For what seemed to be hours, I played dress-up with her help and we took numerous pictures.

Close to midnight, I drove back to my motel dressed, but with a new hair style and a new attitude... and total confidence. I was a woman. I even went to dinner the following evening to a fancy hotel restaurant as Carollyn.

During the next few months in 2005, I met a friend, Linda Holmes, who moved to my area from Maine. We got together numerous times to dress and go out on the town during the day for lunch, shopping and lots of pictures. Linda was about two years into her transition. She was a sweetheart and the co-founder of Mature Women Group.

My salon friend, Linda, recommended I change my hair style to what it is today. She told me that my current style makes me look 10 to 15 years younger.

In November 2005, I received the first "shock" of my life. I had been a member of URNotAlone and VickiRene.net, but my good friend, Lauren Phillips, nominated me for the prestigious Vanity Club. I applied with some hesitation concerned that I would not be accepted, but I received enough votes to become a member.

My second "shock" occurred in March 2006 when KC Tyler selected me to be a member of KC's Top 10. KC's was the first TG site I found on the Internet. I never thought that I would become a friend and a member of her equally prestigious site.

Now, we must jump to Christmas and New Year’s...

I decided to be daring! I had never worn a formal dress except at ILIG, so I paid a visit to my local JC Penney's and "borrowed" a red chiffon formal and a black party dress. My desire was to take pictures and send e-mail Christmas cards to my friends. So, in male persona, I made the purchases and one evening prior to Christmas, I dressed in a long red strapless formal and took my pictures. A few days before New Year’s, I wore a black strapless party dress. Both dresses were so great to wear and I felt so good being dressed "to the nines."

A week after New Year’s, I was back in the Bay Area and another trip to ILIG. I took the black dress with me and JoAnn flipped when she saw the new "complete" product. After a little touchup of my makeup and a few accessories, we took tons of pictures. I stayed for four hours and wore a couple of other dresses JoAnn had selected. Had I had the time, I would have stayed into the night. I drove home dressed and stopped at JC Penney's to return the black dress, as I had no place to wear it again. Sigh!!!

Life as Carollyn has been fabulous. I love dressing as often as possible and enjoying life as a lady. When I dress, I want to create an illusion of a classy, perky and joyful conservative woman. When out, I want to honor women and blend in with others without drawing attention to myself.

I strongly want to help other girls and that was one of the reason the now-deceased Linda and I formed the Mature Women Group ten years ago. I don't consider myself an expert and blush when others consider me an icon in the community. All I want to do is assist other girls and walk hand-in-hand with them on the same, wonderful journey I'm taking.

Wearing Bebe.

Logan Kesler at the 2011 Theatre Under The Stars' Tommy Tune Awards