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Have you been caught xdressing?

by Emma on January 22, 2012

Emma offers up some of her experience with getting caught crossdressing.

Sooner or later the tracks you so carefully cover will turn up. I was like a hunter trying to hide some illegal game. I covered my tracks by purging, packing makeup removal wipes, underdressing only before I went out, never wearing any lady clothes unless I knew I was going to be alone, buying items and mentioning my wife as the cashier rang up the makeup, hiding things in crannies around the house, and going for long stretches in between dressing incidents. Then it happened:

The younger me was fond of stealing into my mother’s closet and wearing her cocktail dresses. When I was fourteen she had the most beautiful red satin and black lace party dress with matching heals, and at the time we wore the same size shoes. So I skipped school one day and wore the dress around the house. To my surprise my father decided to come home early. I saw his shadow move across the window curtains and I ran like a gazelle into the bathroom and locked the door just before he came into view. He thought I was a criminal!

The lie:

(my dad bangs on the door) “Hey! What are you doing in there!? You come out right now!”

(me) “It’s just me, I was scared, I stayed home sick today.”

(Dad) “Well, open the door!”

(Me) “No, I have to use the bathroom anyway. Hold on.”

The awkward lull:

My dad goes down the hall and I get undressed as fast as I can. I run naked into my room before he catches me, and I pull on my pajama bottoms.

The fallout:

My dad grunts something about me going back to school tomorrow, and I put everything back into it’s place as he lays down for his afternoon nap on the couch.


My ex was doing the laundry one day and turned my sweater inside out. The inside of my sweater had lipstick on it, I happened to have been a bit careless a few days before. Of course, she thought I was a cheat, and here’s how it went down:

The lie:

“I have no idea what that is, what does it smell like?”

The awkward lull:

She smells the lipstick. “It smells like lipstick. What have you been doing?”

The cop out:

I close my eyes, lower my head, and explain that I was downtown trying on costumes to get ready for Halloween.

The fallout:

She looks at me funny, tosses the sweater in the washer, and wonders where I got the time to go downtown. Convinced I cheated on some level, she tells me that she loves me in a manner that instills into me a great degree of shame. I then purge my entire collection of feminine items and “go straight” for a few months, counting my blessings she didn’t pry harder.

I actually used that Halloween excuse twice and got away with it. The second time was after she found a wig in the floorboard of my car, years later. Oops.

Beyond those two incidents I was never caught off guard, but I did go out in public as a lady often. I have to say, if I were to go through it again, I would just stare everybody in the face and be honest. Now that I live as a woman my life has just a little less stress in it. I suppose I could have avoided all of the sneaking around and worrying by simply being myself. Share your stories about getting caught and how getting caught made you feel. Just curious :)


image credit: David 23

{ 16 comments… read them below or add one }

Robert January 22, 2012 at 11:41 pm

I never had to sneak or hide as my mom bought me my own dresses from age 11. She knew I was unlike other boys and watched me closely and figured it out.


Emma January 24, 2012 at 11:54 pm

My parents were oblivious. Lord knows I didn’t hide it very well.

avalana January 26, 2012 at 12:16 am

i never snuck around or anything like that,my mom made all the dresses that my sisters would soon wear..lucky me! because i got to wear them first… and i loved the feeling of wearing a dress from the start…like what can i say? i know that i absolutly prefer girl clothes,and have 24/7 for a bunch of years

Angela January 23, 2012 at 4:56 pm

I’ve actually only been crossdressing for a little more than a year now and my little brother already caught me and my mom suspects something. I came home kinda late once and forgot to take off my eyeliner. My mom asked me what was up and I totally denied I had eyeliner on but my brother later kept chizzling away at me with questions until one time he asked me if I was a crossdresser. I blushed and couldn’t give a good answer. The rest you can all suspect how it went down.


Emma January 24, 2012 at 11:53 pm

I hear stories about makeup being the thing that “gives up the girl” frequently, which is odd, because I knew boys that used makeup as part of their style. Well, never red lipstick or anything so overt.

avalana January 25, 2012 at 12:20 am

i guess the last time i was “caught” was when myself and my ggf decided to go swimming and all i had to wear (short of skinny dipping) was a pink and yellow bikini and then a whole family walked around the corner, as i was laying face down ,almost dozing when i heard the mother whisper “cute bottoms” i expect i blushed a bit, but by then i had years of dressing up so i flowed with that comment,thank you very much


Satinique January 27, 2012 at 7:49 pm

After a long shift in hospitality, I decided to go out for drinks… when parking, I dressed into stockings, a beaut red dress, red heels, red bra and panties… I felt GREAT!! Adorned with wig,at about 1:20am, I was passable.. went to stonewall in Sydney, goa bit tipsy… Driving home fully dressed and made up, I totalled my car. Near fatal. Awoke in man clothes with me at all.. an orderly discreelty put my girly attire into a brown paper bag… and totld me how Police, Fire and Ambulance were in attendance.. literally an old fantasy that actually came true!!


Emma January 28, 2012 at 1:31 am

Your fantasy involved a hospital stay? I mean, I get the rest (firefighters and police surrounding you in girl mode), but I just wonder.

Anne January 28, 2012 at 9:20 am

Errr…. fantasy? Sounds more like a nightmare. At least you survived and no one else was hurt.

Ericka Marie January 31, 2012 at 12:35 am

I was in junior high. As I had done several times before, one day I got home to find that I should be alone for some time. Dad was at work, mom took my younger brother to the doctor, and my older brother (who was in high school) was working his parttime job. So, I began trying things on … first panties, then a bra, then pantyhose, then stuff the bra with panties, and then a slip. I walked all thru the house. Exhilerated and at peace. I decided to add a skirt to the mix. Then I heard a knock at the door and I hit the floor! With my heart racing I made it back to the bedroom. About that time I raised up and to look out the window just as my older brother walked by – he was home early!! I just knew that he saw me. I quickly got out of everything and got it all put up. Dressed hurridly in my school clothes and went to the door. He must not have seen my because he never said a word. To this day I am not sure if he saw me and kept quiet or if he didn’t see a thing.


Diane Grace February 22, 2012 at 5:29 pm

I was out shopping on a weekend at Costco – dressed in a skirt, casual blouse and low heels with nice modest makeup. On Monday morning, one of my officemates – a woman who was just hired a month before – told me discreetly that she saw me all dressed up so “pretty” in Costco. In fact, she even had a debate with her husband who had refused to believe her. Well, I had to confess the truth and we actually became good friends. She never mentioned the matter to anyone even after I left that job. Maybe it helped that I had been very nice to her at work.


Debbie April 15, 2012 at 4:34 pm

When I was 16 I liked to ride my bike early in the day I got dressed in a skirt and top and make up I was feeling very good. Then I got to school the next day and a girl I know said she saw me and said I looked sexy. After that we became close friends I would go over her house and she would let me try on her clothes. She taught me how to do makeup and my hair. We had a lot of good times. When we got older we would go out on the town even 30 years later we still get together. Getting caught was the best thing that could have happened to me.


Heather March 20, 2013 at 4:20 am

I can only imagine how wonderful it would be to have a mother who understood my special interest in crossdressing and supported me by buying me my own female wardrobe. Robert you are a most fortunate crossdresser.

Joanne October 24, 2012 at 8:49 pm

Been caught numerous times as a kid, started when I was maybe 5. As the years wore on, it became no big secret that I wore pantyhose, slips, skirts, nighties and make up. It was hell growing up wishing I could wear girls clothes, and when I did getting busted. Eventually, when they figured out I wasn’t going to change, the acceptance reluctantly came. Grandma smuggled a few items she got a garage sale to me, and left them where they would be found, with a simple note “yours”. She said nothing, and neither did I. I’ve been caught in nearly every attempt at a long run CD, but I got better at covering my tracks. When I hit 35, I just quit caring what others thought, and CD nearly daily… Happily!


angel November 29, 2012 at 8:58 am

same here funny now first time i was cought i was about 6 years old my mother would make my sister dresses all very frilly i would where then when know no around we lived in row home in philly and my grandmother lived on first floor we lived on second most of the time eveybody was downstairs so i went up and dressed i was in house dressed and my dad came up and i heard hime come in and i could not get of dress fast enough and there i stood when he came into room he beat the shit out of ne called my mother up and i was hit agian i did not dress for a long time then we moved to northeast philly single home and about 10 or 11 years old i started agian i would take my mother cloths bras panties and any thing i would fit into and wear at night when every body went to bed i would stay up till 1 to 2am and play dress up then i happen agian ifell asleep dressed my mother came in to get me up for school and there i was she woke me and we had a talk that night ask me not t dress agian that did not work but i never was caught agian been lucky i married and wife knows and i dress most of the time she is not into it but goes along


Alison December 15, 2012 at 9:24 pm

This post brought back some memories. As a young teenager I liked to put on my elder sister’s clothes when everyone was out. One Sunday afternoon I was lying on her bed in her bra and panties when my parents came in… I flew to the bathroom, ripped them off and stuffed them in the dirty washing, dressed as a boy, then replaced them in her undies drawer when the coast was clear. Everything went okay from then on, though when my current gf had been living with me for a few months she found a nightie I’d had during my previous months living alone. I said it belonged to my ex, and she believed me.


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