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
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{ 10 comments… read them below or add one }
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.
My parents were oblivious. Lord knows I didn’t hide it very well.
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
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.
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.
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
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 ICU..no 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!!
Your fantasy involved a hospital stay? I mean, I get the rest (firefighters and police surrounding you in girl mode), but I just wonder.
Errr…. fantasy? Sounds more like a nightmare. At least you survived and no one else was hurt.
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.