My my was the dominant partner and she liked to give me rules and control me. I liked it too. So it seemed natural that shortly after I started openly cross dressing in front of her with her approval, she would take it to the next level. Her first rule was that I had to wear a bra all day everyday without exception. She added that I could not go topless in any scenario where a woman couldn’t be topless, referring specifically to the beach. I started thinking about how I would handle this as I remember it was just the start of summer when we had this conversation.
Inevitably, she suggested a beach trip the following weekend. I answered her honestly that I wasn’t sure what I would wear, and we had a talk about it. After discussing several options that she considered acceptable, I decided on what I thought would be least embarrassing for me: wearing a women’s one-piece suit with a pair of shorts over the bottoms.
We went to a department store and I had in my mind that I would find something that would just look like a tight fitting tank top coming out of my shorts. But as we started shopping, I realized everything had much more of a feminine flare to it than I was expecting. I found one that was blue and white vertical stripes, and very obvious built-in bra, and a low-cut neck, but it seemed like one of the best options.
I started thinking about plan B, which was to get a proper bikini top and wear a tank top over it. We browsed a few of those but quickly figured out I wouldn’t really find one that fit me right, and we went back and got the one-piece. We also got a pair of short women’s shorts for me to wear over the bottom. I was expecting to wear big knee length shorts, but we ended up getting something not much bigger than underwear.
When the beach day came, I wasn’t sure how I should dress when we were leaving the house. I was going to throw a pair of shorts and a t-shirt over it. Or, I was considering just taking it with me in a bag and changing when we got to the beach. My wife proposed a third option, for me to just put a loose summer dress over it and go that way. I knew even though she was calling it an “option” it was what she wanted me to do. She pulled an old dress out of her closet and I put it on. I was definitely embarrassed walking out to our car in a dress.
I was even more embarrassed when we got to the beach and I realized I would have to walk from the car to the sand in the dress, with literally hundreds of people around. I decided to just be brave, and I got out of the car. I reminded myself that my wife wasn’t really forcing me to do this, but it was how I wanted to dress. I needed to learn to be comfortable with it.
We walked out to the beach and stopped at the restroom. I walked right into the men’s room with my dress, and went into a stall. I quickly realized that I would have to take the swimsuit off completely in order to pee. That’s a weird inconvenience I hadn’t thought about before. So I awkwardly got undressed and then re-dressed in the stall. It took a while and I explained to my wife the reason for the delay. She said that at least now I understand what women have to go through.
We spent the afternoon on the beach and I hardly thought about what I was wearing. It was interesting having tan lines on my top.
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