Like many, I started dressing as a teenager. For many years, I was content with just sneaking into a pair of panties now and then, but the urge got stronger and I started trying other women’s clothes — the entire time keeping it a secret. I married my high school sweetheart and we were together for ten years before I found the courage to tell her. She said it was okay, but six months later we were divorced. She promised to keep my secret, and to this day I believe she has.
For the next ten years, I was single and spent large amounts of time dressing. I expanded my wardrobe to where I had more women’s clothes than men’s. I did not date a lot, thus I never felt the need to mention my crossdressing to anyone. Once, I started having feelings for a woman; I thought it best to tell her. In the middle of the date, she up and left.
I should mention that I was a police officer in a major city in the western United States. I had been with the department for twelve years when I was assigned as the training officer for my current wife. She is ten years younger than I am. Throughout her training, we had to interact with transgenders and crossdressers on a somewhat regular basis. I saw that she always treated them nicely and with respect– maybe that is what made me start to fall for her. We went for a drink after work one afternoon. She mentioned that she was sad as her training was about over and she was going to miss me. The way that she said it made me feel there was more to it than just a working relationship. It was difficult, but after a few minutes, we both admitted that we had feelings for each other.
A few dates later, I spent the night at her place. As a joke in the morning, I put on her panties; she loved them on me. I admitted my love of wearing women’s clothes and we talked about it for a few hours until she told me she wanted to see all my women’s clothes. We soon headed to my place where everything down to my last pair of panties was pulled out and shown to her. She asked me model several outfits. All of this led to an acceleration in our relationship. Three days later, she moved in with me.
From that first morning, my wife started laying out my clothes. Even on work days, she had me wearing panties under my uniform. Her training soon ended. She was out on her own, but we worked the same shifts. When we get home, she lays out the clothing that she would like me to wear. I must have spent ninety percent of the time at home dressed in women’s attire. Our lives were good.
In May of 2002, my wife told me that she was not feeling well and was taking the day off. I got home and she was happy and cheerful. Informing me that she had a surprise, she lead me to our bedroom and laying across the bed was a beautiful wedding dress. My wife got down on one knee and asked me to marry her. When I said yes, she slid me a beautiful engagement ring on my finger. The next day we both scheduled a week off as soon as possible. My wife-to-be made arrangements with a wedding chapel in Las Vegas for the ceremony. She would wear a tux, and I would wear the dress. On June 8, 2002, we were married.
After I retired and my wife was still working, she continued to lay out my clothes. She has helped me build my confidence. I have not a second thought about going out day or night dressed. I realize that I am an extremely lucky man to have found a woman who not only enjoys, but encourages me to crossdress. My wife has helped me become the woman I love being and I am eternally grateful.Tags: crossdress with confidence crossdresser confidence crossdresser relationships crossdressing while married Relationships