Comments on: Caught Crossdressing by Mom

By: Jason B.

Jason B. — Sun, 31 May 2026 12:11:38 +0000

I started cross dressing at 13.My sister was a year older at 14 and i all ways wanted to wear her panties! We both finially made our First Holy Communions then and i had to wear a suit and tie,and sis had to wear a poofy,short sleeve,knee length communion dress and veil with lace anklets and white maryjane shoes and under her dress the required cloth diaper,plastic pants and tee shirt.She looked so cute and little girlish in her outfit! The next day,i got home from school and mom was out shopping,dad was at work,and sis stopped at a friends house.I snuck into her room,took off all of my clothes,and put on her diaper,plastic pants,communion dress,veil and her shoes.I was parading around in her room when all of a sudden,both mom and sis appeared in the doorway! I was caught!

By: Genevieve Woodhouse

Genevieve Woodhouse — Sun, 14 Sep 2025 15:29:44 +0000

In reply to Patricia Anne Trefoil. Patricia, Thank you for the great story that was smoking hot!

By: Earl

Earl — Mon, 18 Aug 2025 22:12:46 +0000

I was 12 years old when mom and I were both 5’6”. One day she asked me to wear a skirt for her to maesure the hem of skirt. I resisted. Mom insisted and I ended up wearing her panties, 4 inch heals and her skirt. I didn’t look right to her, so she put a sleavless blouse on me to get the skirt on just right on my waist. I complained about the skirt and feeling cold. Mom remove has angora cardigan sweater and put it on me. At that moment, I changed. I could feel the warmth of her sweater she had just worn. I could smell her scent and her perfume she was wearing. Her cloths suddenly turned me on. I was hooked for life. After that first experience, mom dressed me four mor time in different outfits and added more lingerie to complete my modeling for her. After that experience I started crossdressing to be close to my mother. The more I dressed, the deeper my fantasies grew with my mother. Her cloths put me skin to skin with her in my mind. Then her clothes became her skin and I dressed believing I was turning into her in her body. I wanted to become my mother in every way. The clothes I enjoyed most involved angora and cashmere sweaters. One day she caught me by coming home early. She knew what I was doing and left out her red angora sweater, black wool skirt and lingerie. After confessing everything, mom made me a offer I could no refuse. She offered to make me over in her image. I bathed in feminine oils, shaved by legs and body and mom began to dress me in her lingerie and a brown two piece cashmere sweater and skirt. She put makeup on me and placed a wig on me matching her color and style. We looked like sisters. It was a 9 day spring break and mom insisted I remain made over in outfits for those 9 days. I did not resist. I enjoyed being her, in her image for those days. I began to learn how to apply makeup and walk and sit like a lady. We went out to dinner once and even went to church in another town. We continues to share our time together on weekends. When I graduated from high school, we moved to another town where lived as a female together.

By: Miss. Beuitiful

Miss. Beuitiful — Sat, 13 Apr 2024 16:13:44 +0000

What was the movie that you said?

By: Patricia Anne Trefoil

Patricia Anne Trefoil — Sun, 08 Oct 2023 19:04:41 +0000

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.

By: Martin

Martin — Fri, 24 Mar 2023 09:38:44 +0000

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.

By: Wendy

Wendy — Sun, 05 Mar 2023 07:16:36 +0000

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.

By: Mary

Mary — Sat, 11 Feb 2023 17:44:26 +0000

In reply to Guyd.

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

By: Randy

Randy — Tue, 13 Dec 2022 08:11:35 +0000

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

By: Georgie

Georgie — Mon, 24 Oct 2022 14:34:02 +0000

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.