Caught For The First Time

I'll never forget the first time I was caught wearing lingerie.  My mom and sister had gone to the store.  My dad was off somewhere for the weekend.  It was a Saturday, and they left me watching cartoons.  I guess they figured they could leave me alone by then.  I believe that I was around nine years old.  Anyway, as soon as I was confident that my mom and sister were gone, heart racing, I went to my mother's bathroom to see what was in her hamper.  I hit jackpot.  Every item of lingerie that I craved was in there.  I've posted this photo before, but this is the best example I have of what I was wearing that Saturday morning.

Anyway, I was in heaven.  I was all alone in our house, wearing my mother's lingerie.  I even snuck into her closet and found a pair of high heels to wear.  I knew my dad was gone for the weekend, so I wasn't concerned about him.  And I expected my mom and sister to be gone shopping for hours.  I practiced walking in her heels, constantly checking out my sexy form in her mirror.  I was having so much fun.  I decided to take things a step further too.  I went into her makeup drawer and found some red lipstick and put it on.  This was, by far, one of the best "dress up" sessions I'd ever had.  Little did I know how bad of a memory it was about to become.  You see, the thing about hiding your dirty little secret is, that sooner or later, you'll make a mistake.  And I did that day.  I lost track of time.  I sat down to watch some television.  I'll never, ever forget the feeling of panic that I felt when I heard the lock on the door to our den click, and realized someone was coming inside, and there was nothing I could do about it.  Normally, when I dressed up in my mom's lingerie, I stayed out of view of the front part of the house.  Then, I figured, if I heard anyone come in, I could quickly change and avoid detection.  I'd never cut it that close before, but at least I'd been prepared.  But not that day.


As I was sitting on our den couch, wearing my mother's lingerie, my mother and older sister burst in the door carrying their packages from their shopping trip.  I was speechless.  I stood up to run and hide, but it was obviously too late.  My sister was standing just behind my mother, a look of confusion on her face.  Looking back on it, I can understand why.  She was looking at her little brother dressed up in her mother's underwear, including her DDD bra stuffed full.  My mother's reaction was indecipherable to me - at least at first.  But it didn't take long to find out that she was not taking it well - finding her son dressed up like a sissy girl.


She slammed the door and began yelling at me like I'd never been yelled at.  That would have been enough to stop me from ever doing this again.  (Of course, that is completely wrong as it actually didn't stop me.  What I was doing was something I couldn't not do, as I eventually have learned.)  She ran at me and began beating me with her hand, completely out of control.  I was balled up in self defense.  She yelled at my sister to go get her a belt from my dad's closet.  I think my sister was scared to death as well.  She was only about fourteen.  And so she brought my mother the belt.  My mom folded it over and began beating me beyond any whipping I'd ever received, the whole time I'm still wearing her lingerie.  So this is happening in our den, in front of my sister, with me crying and pleading for mercy.  I was telling her I was sorry and that I'd never do it again.  And she didn't stop.  She just screamed that she was going to make sure I'd never do anything so perverted again.


She beat me and beat me until she was exhausted.  Then she told me to go take off her lingerie, put it back where I found it, and then to go to my room.  I was happy to do that.  I never wanted to be seen again.  I stayed in my room all day.  Later, my mom came in to talk to me.  I couldn't look her in the eye, but she made me.  She wanted to know why I did it.  I couldn't explain it.  All I could say was, "Just because," which, of course, is no explanation.  In the end she made me promise to never do it again.  She also told me she wasn't going to tell my dad, as he would never understand.  I was eternally grateful to her for that.  Just facing her and my sister was torture.  My sister never said a word to me.  I think my mom must have told her not to.  And so, in time, we moved on.  But I couldn't resist the pull.  Eventually, I did it again.  But I was so much more careful.  This photo isn't exactly what it looked like, but it is close.  She beat me almost raw. 

The next time I was caught dressed en femme, it was my wife.  I'll tell that story some other time.