The Most Terrifying Day of My Life

Ok so not long ago, my wife shared a post about the most terrifying night of her life. And to be honest, it was probably the most terrifying night of mine, too. But the title for the most terrifying day of my life? Well, that belongs to a completely different occasion. And since we are just a couple days away from Halloween, this frightening story fits perfectly.

It was the day I was almost caught crossdressing by my mother, If you can call trying on a pair of pantyhose "crossdressing", I mean, technically, I suppose it is exactly that, but anyway….

I was around nine or ten years old when I stumbled upon a pair of purple stockings my mother had. They must have been part of a costume, because they were thick, silky, and shiny, nothing like the regular ones she wore on a normal day. But that’s exactly what made them more interesting.

I spent an entire day planning how to go about it. I knew I had to act fast before she decided to pack them away or move them somewhere out of reach. I don’t know, at that age I guess I just didn’t want to miss that opportunity.

So the very next day I carried out my plan. After school I would go to my room as usual and she would go to the kitchen to get dinner ready and wait for dad to get home. That was my window of opportunity.

I waited for her stick to my plan (completely unaware of it of course) and go to the kitchen. As soon as I heard the clanking of pots and pans I sprang into action. I grabbed the stockings, kicked off my pants, and sat on the floor beside my bed. My heart was pounding so hard I started shaking at the mere idea of what I was about to do.

Extremely nervous, I carefully began putting them on, sliding my first leg through. OMG! It was the most incredible sensation I had ever experienced, simply amazing. I was practically hypnotized, staring in awe at how my legs were starting to look and feel wrapped in that smooth, silky, shiny purple fabric.

I had just pulled them up past my knees when all of a sudden the unthinkable happened. My bedroom door swung open, it was my mother. I guess in my sensory trance, I had completely stopped listening to the kitchen noises and didn’t hear the sound of her footsteps approaching my room.

In that moment I really wanted to evaporate into thin air. I prayed for a sinkhole to open up right beneath me and swallow me whole. My entire life flashed before my eyes, all nine years of it lol!. All I could think of in that moment was… This is it. I'm dead. I had been caught red-handed (or purple-legged, in this case), and with no apparent way out.

She stood in the doorway, looking straight at me, and said something like, "Dinner's ready." I was petrified, honestly I don't know how I managed not to shake like a giant bowl of Jell-O. I squeaked out what might’ve been a faint, "Okay," while desperately trying to sneak my legs under the bed.

Obviously, she noticed my extreme nervousness and awkward movements. So like any perceptive mother would, she took a couple steps toward me. "What are you doing?" she asked, her eyes narrowing. "What are you hiding back there?" She added.

That’s it I was done, no doubt about it. All she had to do was walk around the edge of the bed and see for herself what was I up to. Trying to shift my posture and project total innocence, I answered with the classic response of every cornered child in a situation like that… "Nothing!".

She gave me “The Look”, that universal mother stare that instantly tells you you’re F… while I continued silently praying for her to not get any closer. After a few agonizing seconds of awkward silence, she said, "You're playing with your brother's Hot Wheels again, aren't you?".

OMG! My prayers had been answered, I was an instant believer. I immediately gave her a soft, reluctant "You caught me" nod and let out a soft, "Yes..." Her look instantly softened. "You know he doesn't like you touching his toys, now put them back and come to eat." She replied as she turned around and walked away.

I had barely dodge a bullet!. I sat there in total shock, paralyzed as my brain tried to process what had just happened. The scene was still replaying over and over in my head, but I certainly didn't waste any time, I yanked the stockings off and stuffed them back where they were.

The last thing I wanted was for her to have a second thought and come back to double-check my story. From that terrifying day forward, I never, ever attempted to try on anything feminine if anyone else was in the house. And to the best of my knowledge, no one ever found out or suspected about my preferences… or did they?