Caught Crossdressing Stories By Mom

When I was caught crossdressing for the first time, it was a truly awful experience. I felt embarrassed, exposed, and humiliated. However, it was also a liberating experience because it allowed me to finally face up to my true identity. After that initial experience, I could crossdress more freely and feel more comfortable in my skin.

How Did I Get Interested In Crossdressing

When I was young, I became interested in crossdressing. I think it started around the age of 7 or 8. I was fascinated by the way women looked and how they dressed. I loved the way they could express themselves through their clothing and makeup. I also enjoyed the feeling of wearing women's clothes. It made me feel pretty and unique.

I always enjoyed wearing my mom's high heel shoes and dresses. They made me feel powerful and confident. Even though I was a little, I thought I could do anything in those shoes. Now that I'm all grown up, I still enjoy wearing high heel shoes and dresses. They make me feel sexy and beautiful. And I love the way they make me feel powerful and confident.

Once puberty hit, crossdressing took on a whole new aspect. I started to realize that I wished I could dress in girl's clothes all the time and that I preferred the way girl's dresses fit my body and how they looked at me. I also began to feel trapped in the wrong body and that I should have been born a girl. These realizations were confusing and scary for me, and I wasn't sure what to do with them.

One summer, when I was 14, I stayed with family members for a week. It was an excellent opportunity to catch up with them and spend time together. A cousin of mine had a friend who was storing some of her clothes in my cousin's basement while she was away. I could not believe my luck when I realized that anything I took would not be missed and they would fit me. I took the advantage and helped myself to several panties, bras, swimwear, and dresses.

After returning home, I had the house to myself for the days. Because my mom was a single parent and worked during the days, every couple of days, I would get my mom's clothes out from her hiding spot and try on different ones. It was fun to dress up like a girl and feel the other fabrics and styles. I loved how I felt in my girl clothes, and enjoyed pretending to be someone else for a little while.

How Exactly Did I Got Caught

So one day, I am standing in my mom's room wearing the whole outfit. I have on the wig, the dress, the shoes, and the makeup. I feel like a million bucks! Suddenly I hear my mother scream, What are you doing? As I turned around, it felt like all my insides were falling. She did not appear surprised; she looked flabbergasted. For my part, I was embarrassed. I felt like I was caught doing the wrong thing and ashamed. I felt like I had done something so bad that my mother might kick me out of the house and never look at me again.

But she said clean this up, and we'll discuss this later on. And then she departed. I cleaned up all the clothes and changed. Once I was done, she went into her room to change for her Dr. appointment, which is why she had come home early. She had told me this, but I had forgotten. She then left without saying a word. Once she was gone, I threw all my girl clothes in the trash where my mom would see them. I wanted her to know I got rid of them.

As the day went on, I waited for her to get home and give me the lecture of my life. But she came home and nothing. As the days passed, she continued to not bring it up and acted normal. It was like a weight hanging over my head, waiting to drop and crush me. After almost two weeks, II decided she was just going to ignore it or that she had seen the clothes in the trash and decided I had quit doing it. I was becoming depressed though, at having to get rid of my girl clothes.

The Surprising Moment Of My Crossdressing Life.

One weekend after I had stayed with my grandparents, I came home on Sunday night. As soon as I entered the door, my mom hugged me and told me she loved me. This was odd as she would do this when I left the house but not upon coming home. She then told me she had bought me a gift and it was waiting in my room. 

So I went to my room and sat on my bed in a couple of shopping bags. Inside was panties, bras, pantyhose, and girl's clothing. There was a note from her saying, "I love you, exactly the way you are." I started crying and felt a significant weight lift inside me. Once I composed myself, I went downstairs and hugged her and told her thank you. We left it at that.

We did not talk about it for the rest of my time living at home. When Christmas came that year, a number of catalogs were placed on my bed. The first one was opened to the women's clothing section and a note that said, circle things you like. Then, days later, some items appeared on my bed; she also added stuff to improve outfits. This happened each birthday and Christmas till I moved out.

After A Long Time, We Talked About My Crossdressing

Many years later, we talked about it when I came out trans to her. She said that when she first saw me that day, she was shocked out of her senses and even felt hurt. It was something completely outside her experience and worldview. Though she thought long and hard about it, she decided that feeling pain was irrational and that she loved me for who I was and not who she thought I should be. She decided that she would support me even if she did not wholly understand it. To this day, she continues to be fully supportive and proud of me.