Only when we first got married and my dressing was still unknown to her.
I had always had my own collection of lingerie I kept hidden but after we got married her wardrobe opened new possibilities to me. I had never worn a dress before and seeing all her pretty dresses hanging in the closet looked so inviting to me. It was only a matter of time before I just couldn’t resist wanting to know what it felt like and looked like wearing a dress over my lingerie.
My wife one day asked me if I wouldn’t mind if she went out of town with her sister for a few days. I of course said “No I don’t mind” as my heart started pounding with excitement.
I couldn’t believe I was going to be left home alone for 4 days with a closet full of dresses to put on and experience fully feminizing myself for the first time in my life. I didn’t just have dresses to try on but she had drawers full of pretty panties, bras, a couple of slips and stockings. She also had an extensive collection of makeup I could experiment with.
The morning she left I headed to the mall and found a wig shop where I purchased my first wig. The minute I got home I striped out of my drab clothes, slipped into her feminine undergarments and put on my first dress along with my new wig. I was feeling like a real woman for the first time in my life and I was loving how wonderful it all felt.
I stood there admiring what I was seeing in the mirror for a while until I calmed down and then began to spend hours on my makeup. By late the in the day I felt I had done a fairly good job with my total transformation and I just couldn’t resist taking my new look out the front door and into the world feeling like a complete woman.
This was the beginning of taking my crossdressing to another level. Those were the most exciting four days of my life up until that point.
As the years passed I have bought almost all of my own feminine clothing. I have about 7 or 8 of her dresses in my collection, now that she has gained a lot of weight and they no longer fit her.
All of my lingerie I have purchased for myself because her undergarments just aren’t as pretty and feminine as I like to wear.