It was a Saturday morning in the mid-eighties and my wife at the time was at work. She called me on the phone and said that
she wanted to try something that evening. Then she explained what she wanted. It was to be a "date night". I was to dress up
in my feminine best and she would come home to her "woman", the rest was to be a surprise. I heartily agreed!
First was a nice long hot bath. I was not shaving my legs at that point in my life, (that's another story!), but I had a wonderful bubble bath, washed my hair and shaved my face as close as I could. Next, lotion, all over my body, and the blow dryer to finish off my hair. I usually let my hair air dry, but tonight a special effort was called for. I went into the bedroom and sat at the vanity. I decided that I would do everything I could to make this night a "night to remember" in my crossdressing "career". I plugged in the curling iron, and got up to under dress. First, came my bra. (I sure wish I had forms then…), alas, all I had were my water balloons to fill it with. After I had my "boobies" situated, I put on my garter belt and drew my hose up my legs, being careful to clip them securely to the garter belt. Last of my garments, were a new pair of thong panties.
By now, the curling iron was warmed up and it was time to do my hair. My hair was short at the time, but not excruciatingly so. I used the curling iron to flip my hair under in the back and on the sides, then semi-parted it on the side and flipped the front and top backwards. I had to use loads of hairspray and gel to give my fine straight hair some semblance of body! I brushed this out a little and was amazed at the look that I had created for myself! This was the first time that I had done my own hair in a feminine style and it was pretty good.
Time for makeup. I really had no idea what to do here, so I tried the eyelash curler and applied black mascara. This turned out pretty good, (after several cleanups to remove the spotting from my upper lids), I have really long eyelashes and they look great with mascara. I decided that I needed some eye shadow and blush. These were applied with a heavy hand. (I told you I didn't really know what I was doing!) No foundation, or under eye cover, although with hindsight, I needed both. I didn't want to put on my lipstick until after I was dressed, so off to the spare bedroom closet to grab my outfit.
My new blouse was first. This outfit was the first and only purchase that my wife at the time ever contributed to my crossdressing wardrobe. It was a very pretty outfit with a white lace lined blouse and long flowing white skirt. After buttoning the blouse, I pulled on the skirt and tucked everything in its proper place. Then I pulled on my only pair of femme shoes at the time, a pair of 3" white heels. As a finishing touch, I went back to the vanity and put on one of her necklaces, (don't remember which one now…). Dressing done, scrutinized and approved, I put on my lipstick and perfume, then went downstairs to wait on my "date".
When my "date" arrived, I was quite surprised. Apparently, she had prepared for this before she left the house in the morning. She walked in, crossdressed herself! Although it was a nice effort at trying to understand my crossdressing, she never did understand the spirit that drove me. I don't know if I didn't explain it well enough, or if she just didn't get it. But after this first and last date night, our relationship just seemed to fizzle out.
