By Carollyn Olson

Ooooooooooooh, to 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 into practice?

Many of you know, from my earlier articles, I was a late bloomer when it came to crossdressing, starting at age 32. When I began, the internet was non-existent and Payless Shoes, or any major department store for that matter, did not carry women’s shoes above size 10. Now, at age 72, so much has changed and there are so many opportunities for younger crossdressers to develop into “the woman they want to be” at an earlier age. And, for the older crossdressers, we can 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 is not worth living.” I’ve taken my friend’s advice to heart and try to discover something new every day, no matter how small the revelation may be. I’ve learned so much and it has enhanced my ability to age slowly – I feel like I’m 55 and believe I look even younger – and continue to enjoy being out-and-about as an accepted crossdresser.

Even though I have always tried to dress age appropriate, when I was younger I desired to be sexier and show more cleavage than I do now. Unlike many girls, I have never had the sensation that is the sexual component of dressing. However, I do know a number of girls who did, and have related to me, that the feeling has diminished and/or vanished as they grew older. For most, when they were much younger, there was always a sexual tension that went along with dressing, and being sexually aroused when one looked into the mirror. Now, as we all age, one can simply enjoy the look of a pretty woman.

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 young, or to my genes. Either way, I have never received negative comments or been treated meanly when dressed as a woman.

For me, there are good physical signs that come with growing older which make me feel even more natural when dressing.

Gravity and old age have helped with creating more natural breasts and a bit of a beer belly. For years I have worn 38C breast forms, but now, I have enough sagging “male boobs” tissue to fill a 38B…and if I want to go larger, I can wear a padded bra or add a little extra cushion. Another friend of mine, who is the same age, has become so natural, she has developed perfectly formed 38C breasts and is often asked if her breasts are real or if she has had implants. She loves to tell the “inquiring fan” that “they are mine.”

A corset has become a necessity to eliminate the stomach bulge. Ten years ago, I would never have thought of wearing a corset in lieu of a body shaper and hip pads. Now, I would not dress without one, as my waist measurements can be reduced from 34 to 28 inches unless I pull the cords even tighter…ouch!!!

When I was younger, I needed to shave the blonde hair on my legs at least 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 somewhat conservatively. Short 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 at my age, I dress more discreetly.

I love wearing dresses, so it is easy to find lovely outfits, many of which I have purchased from my friends at En Femme. I can’t keep track of the compliments I receive when wearing my En Femme dresses. My favorite may be the blue and white checked Hi-Lo dress, which I purchased last year and have worn so many times when visiting my hair salon or out with friends for a movie or dinner or at social gatherings.

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

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

Applying makeup and getting dressed seem to take longer than in the past, as well. I once could apply my makeup and dress and be out the door 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 for almost every occasion, but that doesn’t bother me. What’s an inch less anyway? You can keep your balance and still look stylish. 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” from around the world who have become confidants and dear friends. When I was younger, I felt so alone and prayed to find a few crossdressing friends. Obviously, when and as the internet developed, it played a huge part in opening the world to crossdressers, and thank God it did. I recall the first crossdressing 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 embedded in me as it is with most “girls.” I figure, if a friend of mine who is in her 90s can continue to enjoy being a woman, why can’t I??? And, so can you!!!