10 Caught crossdressing stories – Confessions that’ll Leave You Speechless

10 Caught crossdressing stories – Hey there! Ready for some intriguing tales? Today, I’ve got a collection of 10 real-life stories about individuals caught crossdressing. 

Yep, you heard it right! From unexpected encounters to funny mishaps, these stories offer a glimpse into a world where clothes don’t define who we are. 

Whether you’ve ever found yourself in a similar situation or you’re just curious, you’re in for a treat. So grab a seat, get comfy, and let’s dive into these captivating accounts together. 

Ready to see how these folks navigated through their unexpected moments? Let’s get started! Read Full Story here

Caught crossdressing story #1 A Girl In Trouble

I was trying on the swimsuit a short time later when I noticed that Mom and Evil Ugly Stepbrother had pulled into the drive and were getting out of the car. (Uh oh.) At this point, I figured if I put my regular clothes back on, sneaked back into my sister’s room, and put back her swimsuit and bra, Mom would very well catch me red-handed.

What I did instead was take off the swimsuit and placed it and the bra into one of my dresser drawers (I placed them underneath my male mode shirts and shorts for good measure). Read Full Story here

Caught crossdressing story #2 Caught Crossdressing at Work

I got caught crossdressing at work. Many evenings, after the people around me have left the office, I’ll slip into some lingerie and stockings, maybe some pantyhose, then go online to chat on cam.

I love a satiny chemise or short nighty. Occasionally, I stay really late or come in on a weekend and get fully dressed in my full-on, ** secretary best.

(I wear ** and perfume everyday. Though, I’m starting to get the feeling from little comments a few coworkers have made that my little secret might not be so secret.) 

One evening about a month ago, everyone had left (or so I thought), so I slipped into my favorite outfit, a silky black babydoll nighty, matching **, black stockings with a seam down the back, and shiny black pumps. Read Full Story here

Caught crossdressing story #3 Caught By Mom

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. Read Full Story here

Caught crossdressing story #4 Getting caught by my landlady

Many years ago i lived in a flat with a Nurse in her 30s and i was in my early 20s. We got on well but there was no relationship at all as i already had a girlfriend. When i came back from work especially if I had been out drinking we would have long heart to hearts.

One night being very drunk I blurted out that I was a crossdresser and whilst I was very nervous about talking about it I was also excited to be opening up about it. Read Full Story here

Caught crossdressing story #5 Caught by landlady and turned into her Househelp

It was a same day like others when i managed to take leave from school to be alone at home and enjoy me time, my feminine side ‘Tiya’ Time. When dad was leaving, he said lock the maindoor from insidemom has not taken keys with her.

So i got up and locked the door from inside as dad left and straight away went to bathroom with towel. There i freshenup then i had bath and moisturise the whole body. Then i drape the towel around my body as a girl covering my breast. Read Full Story here

Caught crossdressing story #6 Nearly Got Caught Crossdressing

Anyone been caught out wearing saucy lingerie or more? I’d love to hear your near miss or caught red handed story. And the aftermath lol. The story below is tame but true.

I once had the responsibility of watering a friends plants while he was away with his Mrs. I went round one Friday evening around 5pm and the sun was still on the pots so I thought I would water them once the shade came over them. Read Full Story here

Caught crossdressing story #7 Got Caught Crossdressing by a Girl 

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. Read Full Story here

Caught crossdressing story #8 I Almost Got Caught Crossdressing

It was a regular day at school, had a few classes left but the teacher had to leave for something urgent and we were given off early. Once I reached home, I noticed that no one was at home and I also noticed that my sister had thrown out some of her clothes in the laundry basket.

There were few t-shirts, pants, and her gym clothes. I picked up the gym clothes which was a Sports bra, a cute T-shirt and yellow leggings, all of which I hadn’t worn before. Read Full Story here

Caught crossdressing story #9 Got Caught by Neighbor in Panties

Ever been caught before? Was it embarrassing? Or did it go better than you could’ve imagined? This is my story of getting caught wearing panties by neighbor.

Normally when I’m home I’m dressed in some way, whether it be short shorts and a cami or silky pajama’s or just a thong under my sweatpants, but regardless I’m usually wearing something. Read Full Story here

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Caught crossdressing story #10 Caught Cross-dressed by Accident From Mom

Since as a young child I have always felt attracted towards feminine panties. I didn’t understand why I liked them possibly because girls wear them and I was lonely.

One day I decided to try on a pair of my mom’s silky panties along with a full slip and one of her nightgowns. I felt wonderful and sexy, even my little guy between my legs was stiff. I was very comfortable wearing my mother’s undergarments and nightgown. After prancing around for a while I laid down on the bed and fell asleep by accident. You can also see Sissy captions and sissy training content on the website.