Our First Date!

9/9/2021

My family went on a one-week vacation. I brought an outfit, just in case I had an opportunity to have a crossdressed outing. On each of our previous vacations, I have always had at least one opportunity to crossdress. These days, my kids are old enough to stay home and let my wife and I go on a date. I conceived the idea to ask my wife if we could go on a date while I wore something pretty. (When I crossdress, I incorporate women’s clothes into my male wardrobe. No makeup, bras, wigs, etc. My children are unaware of my crossdressing.) I asked my wife if I could wear something pretty (women’s clothes) on our date. I said it was not required. I added that it would mean a lot to me if she would do this with me.

My wife has roughly never gone out in public with me dressed up, so I consider this our first date where she willingly consented to me crossdressing. Here are the exceptions where I was in a “costume”:

• Once, she helped me dress as a woman for a non-Halloween costume.
• Another time, she went out with me on Halloween while I was wearing a dress and presenting female.
• A third time, she went to a Halloween costume party with me. At the party, she was wearing a man’s suit and presenting female. I was wearing a woman’s dress and presenting male.
• Other than that, I have surprised her and worn skin-toned pantyhose under shorts with her when we were far from home.

Prior to the date, I told me wife that she had options: I could wear my (men’s) blue jeans and hide everything. I could wear guy shorts with hose. I could wear women’s shorts and a women’s top. Or, I could wear a my knee-length denim skirt.

For our date, we had to get something at a grocery store and then we were going to eat at a restaurant. When we arrived at the grocery store, I asked her, “May I wear something pretty?” She decided that she would cooperate if I wore the men’s shorts with the nude pantyhose. She asked me to wear the shorts to the grocery store, but not to the restaurant. I changed into the shorts in the car.

These days, I am so accustomed to going out in public wearing skirts and dresses, that wearing shorts and pantyhose did not worry me at all. I did not expect that anyone would even notice. My wife said that she was concerned about the morality of it. She was OK with being with me while I was wearing it, but she still is concerned that this is immoral activity. I understand.

We went into the grocery store. I expected her to be afraid. I anticipated that her fear would match the fear I felt on my first outing in shorts and pantyhose. She seemed completely at ease to me. She later said that it was not any different than a guy wearing medical compression stockings. She even held my hand while we walked in the store. We went through the checkout and returned to our car. We were there no more than ten minutes.

We drove to the restaurant. I put on my blue jeans. We had the rest of our date. It was very nice getting to go out with only my wife. The restaurant had a lovely view. My wife and I are having to re-learn how to have conversations without children! I love my wife.

P.S.:
I want to add one more thought. This is a good example of what a true story looks like. It is not dramatic and elaborate with details. It is not sexual. It is not fast. It is like life: slow, logical, and boring. I am weary of all of the false stories on the Internet.