

My name is Mike and this is my story about how I got caught crossdressing by a girl wearing her clothes and makeup. I never imagined any such thing would happen to me and it changed my life forever.
When I was studying in high school, I used to work part time as a painter. One time, Mrs. Brown, a nice lady in my neighborhood hired me to paint the rooms in her house. She was a window and lived with her daughter Sarah who was almost around my age.
The job was to paint all the rooms in Mrs. Brown’s house. I told her it would take me about 4 to 5 days to complete the job. She was fine with it and told me if I could start from the coming weekend. I agreed.
When the weekend arrived, I went to Mrs. Brown’s home in the afternoon carrying my paint brushes and some other work tools. She greeted me along with her 2 cats. Her daughter Sarah was away at her friend’s house. Mrs. Brown showed me around the rooms that I was supposed to paint. After she was done showing me around the house and the rooms, I told her I could start from the living room and she nodded.
I didn’t bring my work clothes this time, because I felt more confident with my work tools & paint brush. First, I moved the furniture out of the way, one by one, then started priming the surfaces of the wall. After that was done, I mixed the colors to be painted and started painting the walls.
Mrs. Brown would bring me snacks and drinks here and there. I would take short breaks then and get back to work. As I was painting the lower section of the wall crouching, one of her cats came close to me, I turned to pat it but suddenly it ran and knocked the chair on which the paint bucket was on. The bucket fell and all the paint splashed all over my clothes, and a bit on my face and hands too.
Mrs. Brown came rushing, hearing the sound of the mess that just happened. When she saw me covered in paint, she was pretty stunned. I told her what happened and she apologized for having the cat interfere me while I was working. I told her it was all right.
I had to take the paint of my hands and body quickly before the paint dried. So I asked Mrs. Brown if I could take a shower and wash my clothes. She showed me the bathroom and I jumped in the shower to wash off the paint. I washed my face and hands with soap and had to scrub hard on some areas to get the paint off. After I was done showering, I washed my clothes. I was regretting not bring extra clothes. I squeezed the water from the clothes as much as I could and had no other option but to wear them. It was quite wet.
I came out of the bathroom and Mrs. Brown saw me wearing the wet clothes. She didn’t want me to work while wearing wet clothes so she said she would get me some dry clothes to wear. I told her I could go back to my house, change my clothes and come back. But she insisted me to stay and told me that she would bring me some clothes to wear. I tried to object but she wasn’t taking no for an answer at that point.
After sometime, she came back with some clothes in her hands. “These are some of Sarah’s old clothes, I am sorry that I don’t have any male clothes in the house since my husband passed away. But I think these clothes will fit you. I will put your clothes out to dry while you wear them and by evening your clothes will be fine to wear. Until then please wear these clothes and you can start painting the walls.” said Mrs. Brown.
I went to the bathroom to change. I checked what Mrs. Brown had handed me. It was a light green t-shirt and black pants. The t-shirt looked pretty plain but had a small bow on the neckline. The black pants looked pretty slim and I wondered if my legs would fit in them.
I undressed and put on the t-shirt first. It was a good fit but a bit tight. Then I picked up the pants and tried putting them on. The fabric seemed to stretch as I pulled it up through my legs. It was very tight fitting and I realized that they weren’t pants but actually leggings that girl’s wear. It was quite fascinating how the leggings wrapped around my legs and hips. A tiny bulge on the front because it was such a tight fit.
It felt a bit strange knowing that these clothes belonged to Mrs. brown’s daughter and that it was actually girl’s clothes that I was wearing. I had never worn any kind of girl’s clothes before, so this was very new to me.
I looked in the mirror to check out my new appearance and I could see that my body looked so different now. It looked more feminine than masculine. I was feeling a new sensation in my body and mind, something that I had never experienced before. I wondered if this was how girls felt while wearing such types of clothes. I was getting turned on and the bulge on my pants was looking more evident now in those leggings.
I lost track of time while I was checking myself out in the mirror. A knock on the door startled me. It was Mrs. Brown. She asked if the clothes fit me. I replied they were all-right and I hesitated to come out from the bathroom and have Mrs. Brown see me dressed in her daughter’s clothes. But I knew, I had no other option. I grabbed my wet clothes and came out. I was doing my best to hide the bulge in those leggings, covering them with the wet clothes in my hands.
Mrs. brown looked at me and smiled. “You look good. I am glad I didn’t throw those clothes out. I knew they could be handy for some occasions.”. I nodded trying to hide my bulge in the leggings. I felt quite awkward, So I told her I was getting back to painting the walls. She asked me to hand the wet clothes and slowly while covering the bulge with one of my hands, I handed the clothes to her. She smiled and pretended not to see my bulge and went to dry the clothes out in the sun.
I started cleaning the mess on the floor, mixed some new paint and started painting again. It was a strange but very nice sensation to work while wearing girl’s clothes. My whole body was having a tingling sensation. I felt very conscious about my body and the clothes that I was wearing. It had a very magical effect on me.
As I was distracted in my thoughts, I heard the front door open and then I saw Sarah coming in. I was pretty embarrassed that she was going to see me wearing her clothes. I had no idea how she would be react. When she came closer, I tried to pretend looking busy and didn’t face her. But then I heard Sarah laughing, she must have noticed it was her clothes that I was wearing. I was too shy to turn around, my face was turning red with embarrassment.
“Are you wearing my clothes? I thought mom got rid of them. They do look nice on you though.”. Sarah said with a big smile on her face.
I didn’t know what to say. I was just too embarrassed. Luckily, Mrs. Brown came in at that moment and she explained to Sarah, what had happened. Sarah asked me if I was comfortable in those clothes. I replied they were okay.
She giggle and went to her room.
I finished painting the living room and decided to call it a day. Then Mrs. Brown brought my clothes back from the drying line and I changed into them. These boys clothes felt so ordinary now. I realized girl’s clothes were a lot more stylish and fun to wear.
On the way back home, I couldn’t stop thinking and admiring how nice it was to wear girl’s clothes and also to be dressed in front of other people. That night I just kept wondering about dressing up as a girl. Next day, I went to Mrs. Brown, this time bringing some of my extra clothes just in case. When I arrived, Sarah greeted me at the door and let me in. She teased me saying if I would like to change into her clothes that I wore yesterday. My cheeks went red, I tried to look normal and just smiled back not knowing what to say.
Then Mrs. Brown appeared and asked me if I could paint Sarah’s bedroom first. She told me she and Sarah were going out that day to visit some of their family and would be gone till the evening. I nodded and Sarah took me to her room. It was pretty cute. There was a bed, her closet, makeup table, study table and two chairs in her room. She wanted the room to be painted in light blue color this time. Sarah helped me move all the furniture to the center of the room. After that was done, Sarah and Mrs. Brown went out.
I got the new paint ready and started painting the walls. After an hour, I decided to take a short break. As I was sitting there, I had this strong urge to dress up. I wondered if Sarah’s closet was open and how many outfits would there be. I knew I had some time before they came back so I went to check Sarah’s closet. I grabbed the handle and turned it, it was open and I could feel my whole body getting very excited.
I opened the closet door wide open to check what was inside. The closet was pretty organized. There were Sarah’s clothes neatly stacked in one section, her undergarments in the other, coats and formal wears in the hanger section, and hosiery & socks in the lower compartment. I was trying hard to resist the temptation to wear Sarah’s clothes again but the urge was just too strong at that moment. I looked around and found a cute mini dress that I could try.
I closed all the window curtains and quickly undressed myself. Then put on the dress carefully. It felt amazing how the dress hugged my body. I went in-front of the mirror to see how I looked and I couldn’t stop checking myself out in that dress. My body looked so feminine, just like a girl’s body. I felt so hot wearing that dress.
After few moments of posing in-front of the mirror, I looked around to see if I could try on anything else. Then I noticed Sarah’s makeup box and checked to see what was in there. I took out one of her lip gloss and applied it on my lips. It made my lips so sparkly and I felt so cute. Then, I decided to walk around the house. Nervously, I stepped out of the room and walked around the house. It felt so liberating and sexy. I was loving every moment of walking around in that dress. I figured I could try on one more dress before Mrs. Brown and Sarah were back.
I went back to Sarah’s room and opened here closet. As I was going through her closet again deciding what to wear, the door suddenly flung open and it was Sarah. She screamed when she saw me and I was petrified. I was so busy checking out her closet that I didn’t even hear Sarah coming inside the house.
I felt so embarrassed. How could I be so careless and stupid. Sarah was very angry and asked me why I was dressed in her clothes and going through her closet. I said I was really sorry and told her I was just curious. I couldn’t look at her face. She took our her phone and started taking photos of me. I was scared and trembling now. I begged her to stop taking my pics. Sarah put the phone down, told me to take off her dress and get out of her room.
As I was picking up my clothes from the floor, Sarah noticed the lip gloss that I was wearing and screamed at me, ” You went through my makeup as well? Don’t tell me you are wearing my bra and panties too?”. I nodded no and rushed to the bathroom to change. It was so humiliating, even more because I was caught wearing her dress and makeup and now everybody would know about this incident.
I changed back in my clothes. I was terrified of the consequences that I had to face now. How was Mrs. Brown going to react knowing I was sneaking in her daughter’s closet and wearing her dress and makeup. So many questions were pouring inside my head. I came out of the bathroom, wishing I could just vanish but I had to face Sarah and she was waiting for me. I handed her the dress. I still couldn’t look at her face, I was just too ashamed. She asked me why I wanted to wear her dress and I decided to come clean. I told tell her everything that happened since I wore her clothes the other day and how I couldn’t stop thinking about wearing girl’s clothes.
Sarah seemed to calm down a bit after hearing what I had to say. She said ” I am still mad that you sneaked into my closet and went through my stuff. This is so weird. I have to tell mom about it now.”. I was terrified and begged Sarah not to mention anything to her mother and I would do anything for her. Luckily, Mrs. Brown was still out and I tried my best to convince Sarah to keep the whole incident a secret and delete the pics of me that she took.
“Sorry for screaming at you like that but I forgive you. But this is so crazy that you went through my stuff and even wore one of my favorite dress. It’s a bit funny now that I think about it but you scared the crap out of me for a bit.”. Sarah said with a soft smile.
I apologized and thanked her for understanding. I requested her to delete the pics and she said she would delete them. Then I asked her if I should get back to work or just leave and she said I could continue with the work. It was so awkward for me but I started painting the wall in Sarah’s room while she was out in the living room. The vision of the incident kept replaying in my head. After I was done painting the room, Sarah came in and said I did a nice job. I told her I was done for the day and thanked her again for forgiving me. She said it was all fine.
As I was packing up my stuff to leave, Sarah handed me a bag and said ” Here are some of my old clothes. They are kinda dirty but you can wash them and try them if you like.”. I hesitated and said it was not necessary but she insisted so I took it and thanked her.
“Okay, see you tomorrow and don’t go through my stuff again.”. Sarah said with a smile. I nodded and headed back to home wondering on the way what Sarah had packed for me in the bag she gave me. I was too nervous to check them out on the way and couldn’t wait to get home and check. It was a wild day for me and I was very lucky Sarah was kind and nice about it. But I knew that it was just the start to my crossdressing journey…
Submitted by Mike Peterson


What a beautiful story, I can imagine how beautiful you felt, a pretty and sensual lady.
I had a similar thing happened to me I was living with my older sister and I was walking by her room worked inside and seen a bra and panties I went in thought I wanted to try them on so did then I looked in her closet seeing a white blouse and a black skirt figured it wouldn’t matter if I tried those on then I walked out to the front room to see what I look like all of a sudden I heard a noise my sister and her girlfriend is show up they walk in and ask me what I was doing I told them I wanted to see what it felt like to wear a skirt they asked me why I had a bra on I said I thought it look good they said it does look good on you it is okay they said we will have a dress up day I got real excited I didn’t know what to think I have been dressing up since then my sister and her girlfriend come by and we go out together it is a lot of fun