Warning: count(): Parameter must be an array or an object that implements Countable in /home/customer/www/crossdressersociety.com/public_html/wp-content/themes/karma/framework/truethemes/metabox/init.php on line 757
Deidra Reveals Her Crossdressing Desires – Crossdreser Society | An Online Resource for Crossdressers | Transgender

Deidra Reveals Her Crossdressing Desires

Posted by:

Deidra Gets to Enjoy Crossdressing at last!

I am 72 about 5′ 6″ with blue eyes and gray hair (it was once black).  For almost my entire life I wanted to try crossdressing but I was always afraid of getting caught & being the target of scorn.

I have been crossdressing for 3 years as part of my “bucket list”.   I have done several benefits for families of sick & injured children and plan to do more.  My only regret is that I didn’t start this many years ago.

About 3 years ago I finally decided to stop living in fear of what someone else thought and went for it so here is Deidra.

I’ve never been this happy before!!!  I do all my shopping online except for make-up which I buy at a local beauty supply.  The ladies there are most helpful.  I go to the mall here occasionally to strut around a bit and sure get a lot of attention.

I now have about 40 dresses–all of them short, tight, and shiny along with 22 pairs of 6 inch heels.   I walk in them like I was born with a pair on.  My friends marvel at that but its all about ATTITUDE!

I would like to say to all younger people–don’t let “society” dictate how you should live my life.  If I could go back Deidra would have happened 40 years or more ago.  I’m not saying everybody should be a tall skinny drag queen but if that’s what you want go for it with gusto.

When I go out you would be amazed at the “straight” (and married) guys ask for my phone number.  I always give them one of some kind.  Again, Marcy,  thank you for your time.  Much love to you and your viewers.




deidra crossdressed


About the Author:

Hi, I’m Marcy Simpson, the founder and creator of Crossdresser Society. I have been a crossdresser for over 25 years and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.


  1. Nel  January 16, 2014

    Deidra is terrific…!

  2. Karla  January 16, 2014

    Hi welcome I must say your fantastic I go by my name Karla aim public for fun but well I enjoy crossdresding thanks

  3. Carol  January 16, 2014

    Awesome Deidra you go girl :). Age is nothing more than a number. You look beautiful in your photo’s and your enjoying yourself. Have a fun 2014

  4. Patti  January 16, 2014

    Amazing tale and remarkably similar to mine. I did not come out until told I had less than a year to live. My only regret. But it is better to have come out than to never have dressed at all. PS You are very attractive

    • Deidra  January 17, 2014

      First I hope you doctors are wrong. Thank you for the compliment

  5. Charlie  January 16, 2014

    Great pictures and your truly an inspiration to others

  6. Karla  January 17, 2014

    My second comment thanks I use eBay to buy wigs makeup cloths ok I started in making funny films to frustrate my fans I have millions of them as I dressed up more and more I felt good about it and I feel sexy
    Very sexy. Aim married to a woman who understands all this
    I truly like this very inspirational person thanks

  7. Emily Garcia  January 19, 2014

    You look fantastic…you have beautiful body…..

  8. Susanne  February 3, 2014

    Just great the pics.
    And you are right: never let dictate your life by “normal” people. I wish I would have started earlier But at least I began one day and since then I had a lots of fun.

  9. Phyliss  December 22, 2014

    Hi Deidra:

    You are very pretty and feminine in appearance. I too am in my 70’s, semi retired and enjoying my renewed life as Phylliss. My wife, who passed away 2 1/2 years ago, was not sympethetic to my desire to crossdress. She was a lovely lady and mother to our wonderful children, and I miss her dearly, but her mind on dressing was firm. Only occasionally durining our 49 years of marriage was I able to express my feminine me by dressing as a women for halloween or costume parties. Other times – no way. Crossdressing has helped me deal with the grief that most experience as a result of loosing someone you love. Shortly after her death, while working on estate matters, I said “why not”. I’m sitting at my desk alone and I could sense the relief I would experience if was wearing a dress while ding this work. I shopped on e-bay and Etsy alot. I learned how to measure myself so mistakes were limited, and I soon acquired a taste for buying nice outfits. Not everything I purchased turned out the way I had anticipated, but about 80% of what I bought I still have in my closet. While I do have a part time job to get me out of the house,I have ample time to take care of my feminine clothes and plenty of chances to wear them. I do my nails frequently and, when I have a few days in a row when I can be at home, I will take the extra time to do acrylics.

    Thanks to e-bay its fun to shop on line. It is a challenge to key into the right categories for items I’m looking for, but after a while one can become good at finding what you want. I have purchased some very pretty dresses, skirts with flattering tops, I have many lovely slips and a few gowns in my wardrobe. I love wearing these clothes so much that I feel something is missing when I am not.

    About four years ago I went to see my doctor about a lump that had developed in my left breast. After having a mamogram and ultrsound the doctor determined it was a benign condition, but needed watching. At the same time the doctor advised me that I was showing evidence of early stage gynecomastia or enlarging breasts. I had a hormonal count performed which supported the doctors intiial evaluation that I had a hormone imbalance. Two years later I had the lump removed as a precaution. The surgeon that perfomed the operation spoke a little about breast growth, which was helpful, and advised me, somewhat, on what I could expect in the future. The mamogram and ultrasound scans continue to show increased breast growth from one year to the next.

    While I love to wear female clothes I never dreamed that I would be wearing bras for comfort rather than for crossdressing affect. I’m not sure what size bra I needed when all this started to happen, but as my breasts grew they became uncomfortable, not only from the extra weight but also due to pain. Now I am a firm 40C breast size. I wear a bra just about every day. For vanity reasons I conceal my breasts with tight fitting sports bras when I go out. Regardless of what I think about my appearance, people do stare at you for looking different. During the winter, when I have loose bulky clothing on, I am able to wear a regular bra. The rest of the time, when I am dressed as a lady, my recently developed anatomy only enhances my crossdressing experiences.

    Best regards Deidra and love to all.

  10. Carolyn  December 2, 2015

    Deidre good onya sport I am now 80 and still dressing in fact have just got two new pairs of 6″ heels shoes
    one red with a platform the other black and strappy. I love your dresses tight and shiny my thing is satin and spandex some frilly some tight and clingy.


Add a Comment