Young Is As Young Does

By Carollyn Olson

Carollyn Olson, the author of today's post

Ooooooooooooh, I wish I knew then what I know now. But, then again, would I have put everything I have learned in near 40 years of crossdressing to practice.

I was a late bloomer when it came to crossdressing, starting at age 32. When I started, the Internet was non-existent and Payless Shoe Source didn’t carry women’s shoes over size 10.

Now, at age 72, so many things have changed and there are so many opportunities for younger crossdressers to develop in to “the woman they want to be” at an earlier age. And, for the older crossdressers, we now have to change to continue refining ourselves.

A friend of mine once told me, “When you go to sleep at night and if you haven’t learned something during the day, the day was not worth living.”

That’s why I take advantage every day to learn something to enhance my ability to age slowly and continue to enjoy being out and about as an accepted crossdresser.

Even though I have always tried to dress appropriately for my age, when I was younger I desired to be more “sexy” and show more “cleavage” than I do now. The biggest plus from my early crossdressing days was that I have always been accepted when out in public. I don’t know if I can give credit to my mother, who always looked younger than she was, or to my genes. Either way, I have never received negative comments or treated meanly for dressing as a woman when out and about.

For me, there are good physical signs that make me feel even more natural when dressing.

Gravity and old age have helped with creating more natural breasts. For years I have worn 38C breast forms, but now I have enough sagging male tissue to fill a 38B. And if I want to go larger, I can wear a padded bra or add a little extra.

Another friend of mine has become so natural, she has developed perfectly formed 38C breasts and is often asked if her breasts are real or if she have implants.

When younger, I had to shave the blonde hair on my legs about once a month. Now, due to aging, the hair on my legs has virtually disappeared. What a pleasure to not have to “lather-up” when showering.

What to wear has never been a problem for me. I have always tried to dress appropriately and more conservatively.

I love dresses, so it is easy to find lovely outfits, many from my friends. I can’t keep track of the dresses I have received over the years and I have always been complimented on my appearance. My favorite may be the high-low dress,I purchased last year and have worn so many times when visiting my hair salon or going out with friends.

Dress hemlines and low-cut sweaters and blouses are still in vogue, but I don’t wear short skirts or expose my breasts as often as I did in the past. Both are still fun, but should be worn discreetly.

There are definitely a number of negatives from getting older, but I try not to worry and try to compensate the best I can.

The biggest drawbacks are “wrinkles” and “turkey neck.” One always wants to look their best and as young as possible, so I use aging creams, taping on my forehead to lift my eyebrows and taping under my jaw line to get rid of the “turkey.”

Makeup and dressing seem to take longer than in the past. I once could apply my makeup and get dressed in less than an hour, but now it has stretched out an additional 30 minutes or so. However, the older I get, the more of a perfectionist I have become. I will always want to look my best.

Mostly gone are the days of wearing 4-inch heels on almost every occasion, but that doesn’t bother me. What's an inch less anyway when it comes to keeping your balance and still looking stylish in one overall appearance? I have to remember I’m not 35-40 any longer.

Confidence remains the key to crossdressing no matter what age you are. Being older I have found an even greater desire to be out in public even though I never was “closeted” or afraid to get out and do things when I was younger. I always felt that “if I worked so hard to get dressed, why wouldn’t I go out and enjoy myself.”

Being an older crossdresser, I have also developed a number of relationships with other “girls” who have become confidants and dear friends from around the world.

When I was younger, I felt so alone and prayed to find crossdressing friends. As the Internet developed, it played a big part in opening the world to crossdressers and thank God it did.

I recall the first Internet website I discovered was Vicki Rene’s “Prettiest of the Pretty.” I could not believe the beautiful men-turned-women on the site. It definitely helped me with my desire to look “the best I can be.”

What does the future hold? I know I will never give up my desire to crossdress. It is imbedded in me. I figure if a friend of mine who is in her 90s can continue to enjoy being a woman, why can’t I.

Source: Rue La La

The ladies of the 2015 Boston stage production of Casa Valentina