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Caught Crossdressing by Mom

Caught Crossdressing by momI started crossdressing at a young age. A movie I saw once about a boy who was dressed as a girl by his mother got me very curious about dressing up. One time, I secretly got dressed in one of my mother’s dress when I was 12 years old. I simply loved the sensation and my desire to feel & look feminine grew with time.

I didn’t have much options back then to dress up. I could dress up very little because most of times, my parents would be home too. I only got to wear what I could find in the laundry most of the times. Sometimes, mom would have her recent worn clothes hanging in her bedroom and if no one was around, I would sneak in and put them on. It was such a rush for me. 

One day, I was alone in the house. My parents had went to a party the night before and both of them were off to work that day. I had a holiday break after completing my school exam. I went into my parent’s bedroom to find if there was any mom’s clothes I could try on.



The dress that my mom wore the night before was lying on the bed. It immediately caught my eyes. It was a burgundy bodycon dress with a cut on the front side. I also found her bra, pantyhose and heels lying in one corner of the room. It was already making me tingle with excitement just thinking about putting them on . 

I undressed myself and put on the bra first. It was a bit bigger for my size but it felt great. I could feel the bra’s strap around my back. Then I filled the bra with socks and adjusted the shape to make it look more round.

It was then time to put on the dress. It had a zip in the back. I unzipped it and then slowly put it on. Slowly got my body nicely inside the dress and zipped it from behind. It was a perfect fit. Instantly, I felt so feminine and beautiful.

Then, I got the pantyhose. I had never worn them before but always wanted to wear one. This was my best chance. So, slowly I put them on. I struggled to get it on because the alignment always got wrong. With quite a bit of effort, I finally got the pantyhose on. It was an intense feeling that I had never experienced before. I completely fell in love with how it felt on my legs. Lastly, I put on my mom’s heels and my feet could fit in them. It felt amazing.



I walked around the room in my new avatar and couldn’t stop staring at the mirror. I really felt like a girl. It was so nice to walk around in that attire. Then I saw my mom’s makeup kit on the table and from it picked a nail polish that matched the dress color. I was enjoying every bit of it. I started applying the nail polish on my nails. I was pretty bad at it. Just as I was finishing to apply the nail polish, I heard our main gate opening in the front. Someone was home early. I panicked and rushed to place everything back to where they were. I started to undress, I took off the shoes and placed them back.

Then, I tried taking off the dress, but I couldn’t get the zipper back down . I had maybe a couple of minutes before my dad or mom saw me and I was really close but I just couldn’t do it . I was mortified , my heart was pounding , I could feel my face was becoming bright red and I was sweating heavily.

I knew I couldn’t use too much force, otherwise the zipper would rip off. It was just stuck somehow and my only choice now was to run back to my room. Just as I turned to the door, it flung open and I saw my mom. As soon as she saw me, her face looked completely shocked and I had a very big fright that I almost screamed.

Immediately she asked me what was I doing wearing her clothes. My face became so red and I couldn’t utter any words. She noticed how embarrassed I was feeling and tried to calm me down. She spoke gently and told me to take off the dress. I told her the zipper was stuck. She turned me around and unzipped the dress. As she was getting the zipper back down, she saw I was also wearing her bra.



She laughed and said ” No, not my bra too. Why did you wanted to get dressed like this dear?”

I said I was really sorry and I didn’t know why I wanted to but I just felt like trying. I wasn’t a kid anymore and that made me feel more embarrassed. My mom then asked me how long I have been dressing up in her clothes and I lied saying it was my first time. The good thing was she wasn’t very angry and tried to be understanding. As soon as the zipper was down, I rushed to my room to take of the dress and pantyhose.

I returned the clothes to my mom and she said if I wanted to talk about it. I said I was sorry and just wanted to know how it felt to wear a dress. She agreed to not tell dad and after that moment I made sure to never get caught like that. My mom didn’t asked me about it again and I think I feel more comfortable like that.  

The End

– Sent by Rosie 

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1 Comment

  1. Very nice story

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