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