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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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28 Comments

  1. Very nice story

    1. I so wished I had dressed more as a wittle girl! I so wanted to be a sweet young lady for Mommie, and be her best daughter! I wuv being in dwesses and skirts, wif my wittle panties and bra under them, and to pway wif wittle bois. One day I weally want to have a wittle boi want to marry me and make me his wife. I would be ever so sweet to him. Oh, such are the way I feel these days. I so want to be his woman!
      Miss Roxanne Lanyon

  2. My parents divorced when I was 12. I started to dress up to and feel like the “woman” of the house, not the “man”. One night my mom was out on a date, so I dressed in my mom’s bra, panties, pantyhose, dress, heels, pearls and full makeup! It was so freeing. But, when she came home early, I was caught red handed. My mom was shocked and asked how long had I been doing this? I panicked and said this was my only time. A total lie. The next morning we had a very brief talk and she wrote the event off to the divorce as a one off. I’ve been dressing ever since!

  3. I started cross When my mother asked me to wear a sweater suit to match the hem of her coat with the skirt. At 12, we were both 5’6”. I resisted and gave in. She tried just the skirt and the coat. She was not satisfied and added her girdle, slip, skirt, bra and sweater. The skirt and sweater were cashmere. I felt the soft texture of the sweater, the smell of my mother and her perfume and I was hooked. By the end of the afternoon she added stalkings and had me wearing two more sweater outfits with the camel hair coat. My heart pounded and I had a restrained woody in her girdle. After that experience I cross dressed on the sly when ever I had the chance for a year. I wanted to be close to my mother and I felt embraced in her soft cloths. A year later mom caught me in here cashmere suit. Mom was not surprised or angry. We talked and I admitted my strong feeling for her in her attire. Mom had me remove her cloths and had me bath in a scented bath and shave my whole body down. She had me dress again and every inch of my body felt wonderful. Than she applied make up and a wig with matching style and color to her own. Mom was turned on. I was turned on and I spent my whole Easter vacation made over in my mother’s image. We spent many weekends and whole summer together as girlfriends. To this day, I still crossdress behind closed doors.

    1. That’s terrific. I wish sometimes something like that had happened to me.

    2. Hello!amazing..for me just the same story…but i put on my mothers half slips at age 5?6?..while she stood next of me…i was hooked..my mom tolerated it…(dad was 5months away mil operations)..she started showing me how to put on stockings..she told me till i was 14/15years always girly talk about fashion .skirts dresses how they mafe them themselves in ww2 time.. she would do my hair ..while i had to wear her mostt loved dress…she said i always wanted a daughter(i was her only child)
      I guess my osychopatic military dad abused her finacially emotional and mental…so she simewhat hated MAN…so she mafe me her oart-time daughter as long we were alone…when tyrannic dad came home…her schouted at her yelling commdang always angry…..i had to act like a “man”=hunting with him(killing defenceless unguilty animals…getting drunk on gallins of beer….so i ended up in the army(special forces)had to fkrget my dear mother and ne as a gurl/woman i loved to be….now after the army…i can be at some time what i am a crossdresser a woman

  4. Charming story … and I love the picture! You have great legs!

  5. good story’s — there is not a thing I like more than dressing as a girl , then go to then shopping

  6. good story’s — there is not a thing I like more than dressing as a girl , then go to then shopping
    as i am there i will buy new bra an panty’s of different color’s

  7. im 51 and married my wife knows im fem and she buys my panties and she pays to get my hair fem permed and curled and rollerset and have curlers put in my hair looking for another into girly clothes and a fem hair perm

  8. I enjoyed reading your story. I wonder what my life would have turned out to be like if I had been caught by my parents and confessed that I enjoyed wearing femme underclothing.

  9. By now I am a mature crossdresser. I think I want to graduate and become a real trannie girl, and wear feminine clothes 44/7! I simply adore being feminie, and would even love to go out on a date as Roxanne, with a sweet, knowing man! Oh my! I just know I could be a really loving girl for a nice, caring man, someday!
    Miss Roxanne Lanyon

  10. That’s a beautiful story.when I was small,our neighbor lady watched me after school every week day.For some reason it was important for her to dress me like a girl and demand I act as if I was her daughter every day. I did love her, even though she was very strict and controlling, the feminine clothes she dressed me in always made me feel peace and joy. I was with her nursery school thru 3rd grade. Will never forget her….

  11. i was 13 and a half when i started to dress, my mom worked as a nurse then they wore all white bras slips stockings and shoes, her bra would always fall so tried kid sis omg it felt great, from then on i was hooked. one day i got fully dressed in kid sis cloths, black bra, panties,white half slip lime green skirt,light pink blouse red tights white mary janes and did my chores, came up from the basement and was confronted my mom. all she said i was dressed all wrong and come with her to sister room where she re dressed me and re named me from then on i had to dress

  12. lovely story. I have loved to dress in ladies clothes always made me feel so feminine.xx

  13. there is not a thing better than to dress as a girl

  14. love to dress up as a sweet girl then go to town an do sum shopping

  15. Nice! My mother caught me rummaging through her lingerie drawer when I was young less than 10, she walked in when I thought she was going to be out for the afternoon and caught me in the bottom half of her canary yellow two-piece baby doll. Instead of freaking out took a cut off and slowly slipped the top half of my shoulders. She started to brush my hair and told me how adorable I was. She nurtured me for many years and I trust in front of her from the time I came home from school to the next morning when I left we shared many things and she taught me how to be a good young girl, and when I was older and she was older I would still trust for her and black bras and panties and more mature see through tops and short shorts she always got a kick of how cute and sexy I looked!

  16. Well, her am I again! I am still not yet married, but am still looking aroun! I have had a few men interested, but none into marriage yet. Some day, I hope! I am a mature woman now, but I think I am still cute! I am learning how to please a man, and love to practice on him! One day there will be an ivory lace gown in my life, and I know I will be the happiest woman in the world! with, I hope, the happiest man on my arm!
    Miss Roxanne Lanyon

  17. I love wearing a maid uniform and working as a real maid. I have a friend who lets me do this about once every two weeks dressed in one of my maid uniforms. She gives me proper maid’s jobs to do and they have to be done properly. I do get punished before being dismissed with a riding crop across my knickers but normally not very hard just as a token of our relative positions in the house. However if I have done some thing wrong i.e something broken or not cleaned properly the punishment is real and hard and I still have to thank her for it with curtsey

  18. just love to dress for my sister in law Verige , she say I am so pretty

  19. I was once nearly caught by my mum, I was dressed as a secretary: – knee length black pencil skirt / white blouse/ black jacket/ 4″ stilettos, I’d done my hair & I was just doing my lipstick in the mirror at the top of the stairs when she unexpectedly came home early, when I think back now, I wish she had caught me, or I had gone downstairs & presented myself to her as the woman I knew I was, because I’d would have come out as the real me a lot sooner & as for men there’s no wonder I prefer been a woman.

  20. I started dressing up when I was 13. I would go to the basement and try on my older sister’s clothes that were in the laundry. I loved pretending to be a girl, wishing I could wear girl’s clothes all the time. I always liked how they felt. Girls are so lucky.

  21. I like the story about the boy putting on his mom’s dress huh I’ve done same thing with my sister’s clothes but I never got caught now I wish I could find somebody to help me do more women’s clothes is fun to wear it makes me feel really good

  22. Started crossdressing at an early age. Has a sister that was older, but we were similar in size that I could wear her clothes. She had dressed me up in her skirts, dresses, and school uniforms several times. My mother had seen us playing several times and commented that I looked cute as a girl. Then one day my sister didn’t want to play dress up any longer. I still liked dressing up, so continued to do so in secret. My sister had some hi-cut stretchy nylon panties I found in her panty drawer one day and felt I just had to try them on. They fit me perfectly, and I instantly fell in love with them. I had more breast tissue than most boys, so I could fill out her old training bra and didn’t need to stuff her bra very much. At the time, I didn’t know what was happening, but I hoped my breasts would continue to grow, so I could wear a bra like my sister did. I preferred wearing girls’ clothes and just felt better wearing skirts and dresses. When alone, I would wear her panties along with her old bra, blouses, skirts, socks, and heels or wear one of her dresses and got quite good at zipping myself up. I practiced walking in heels and got quite good at it. I looked forward to being alone, so I could get out of my boy clothes into the clothes I preferred wearing. I was afraid to talk to my sister about it because I didn’t know how she’d react to me still dressing up without her knowledge and wearing her bra and panties. I liked her panties so much better than my own underwear that I started wearing her panties everyday. I liked being able to wear panties, but soon someone found out. My mom was going through some clothes one day and stopped me asking for me to try on some things to see if they fit. She handed me some shorts and I took it and turned to go to my room to try on. I was planning on taking off the panties and putting on my underwear and coming back out, but she told me to hurry up and do it right there. I was wearing my sister’s white hi-cut stretchy nylon panties that day and even though they were plain, I knew they couldn’t pass for my underwear. I was worried about changing in front of her and I tried to get her to let me try them on privately, but she insisted that I do it right there. I hoped my shirt which was long would hide the panties. Trembling, I unbuttoned my shorts and slid them down and stepped out of them. I was getting ready to try on the other shorts when she stopped me and gave me a shirt to try on instead. She had me take off my shirt and I was standing there embarrassed wearing only my sister’s hi-cut panties. I felt naked. My mother did the laundry and shared that she had realized something was wrong because my sister had been using about twice the amount of panties she should have been, and I hadn’t been using any underwear. Her suspicions confirmed, she called my sister in so she could see me standing there wearing her panties. My sister didn’t seem mad about it, but did looked shocked to see me wearing her panties. My mother seemed upset and asked why I was wearing my sister’s panties. I tried to explain about liking the way her panties fit and felt and about liking them better than my own underwear, but that must have been the wrong thing to say because my mother became angry and screamed at me telling me that panties were only for girls. She grabbed a belt and had me bend over and then started slapping my bottom with the belt all the time screaming about me wearing my sister’s hi-cut panties. Me dressing up wearing skirts and dresses had been okay, but me wearing panties was terrible to her. I didn’t understand why a boy preferring to wear panties was so terrible, but learned that some women were not understanding at all. I told my sister that I was sorry for sneaking into her things and she gave me a hug. I found out that my sister didn’t like those stretchy nylon panties very well and preferred cotton panties. She later gave a few pairs of her stretchy nylon panties to keep, and I was careful to hide it from my mother who remained a bit suspicious of me and I knew she didn’t understand. When my sister switched to cotton panties she wanted to wear, I was able to save the rest of her stretchy nylon panties from being thrown out.

  23. I used to be a crossdresser and i loved it. I don’t do it any more after i remembered that 13 years ago , i was in hospital for a different reason, when i had a heart attack, the doctors brought me back thankfully. Thinking now if i had one when i was dressed in my flat, that my daughters would find me dressed as a woman, that thy wound not understand.

  24. When I was 11 or 12 I found my sister’s Intermediate Girl Scout Handbook. Reading the parts about the Promise and the Laws gave me a woody for some reason. The description of the investment ceremony and the description of the uniform dress kept it up but I didn’t know what to do about it. In high school I wanted to be a flag carrier on the girls color guard. To wear the beautiful, full skirted uniform dress with high, white boots, to feel the flagpole rub against my girdled crotch as I marched. I had a crush for the girls color guard teacher, a butch looking woman and would have loved to have been one of her girls. I still have a fantasy about being caught in the Girl Scout uniform dress by my mother and becoming a girl scout, then being teased by my troop leaders and sissified by them and the school color guard teacher.

  25. What was the movie that you said?

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