Confessions of a Cross-Dresser

 
 

 

Looking back, I’ve been cross-dressing for years. 

I guess it started out slow…at a tender age of 12. 

I’d sneak into my stepfathers’ closet and grab his favorite cotton shirt to wear over my skin-tight jeans. The blue and gold paisley-print perfectly matched my eyes and long hair.  

I never considered that…I might have a problem. 

Over the years, I preferred to wear men’s’ shirts either to hide what I considered my huge hinnie, embarrassing thunder thighs, or after I was married to cover up an enormous pregnant belly. 

Honestly, I believe that on a cold winter’s day there is nothing more comfortable than wearing a guys’ oversized jacket with warm layers of clothing underneath. 

Anyway, my cross-dressing turning point came to pass when my daughter left home and I was picking through and cleaning out Keelyn’s leftover crap. Shockingly I spied a faded pair of men’s Calvin Kline’s. 

Immediately I knew, the boxers did not belong to either of her older brothers because my sons’ have always worn tidy-whities. (I mention this because I need to clarify that this undergarment did not belong in my household.) 

What a second. Are you thinking that some young man snuck out Keelyn’s bedroom window without his shorts on? If so, I can guarantee that boys’ bare butt has a nice scar on it from my mean as a snake chow-chow, Sterling. (Let’s just leave it at that okay!) 

After calling friends to discuss the outlandish underwear discovery, I was clued-in. It seems to be all the rage for girls to wear boxers to bed. All right, I’ll buy that.  But…they way I look at it, if these shorts ‘really’ are all that comfy, I’m going to wash ‘em up and try sleeping in them myself. On second thought, I’ll wash them twice. God knows where they’ve been. 

Wow! Who knew that boxers do not have that creeping underwear feel, plus the legs have plenty of breathing room? Face it, a t-shirt and a pair of oversized lightweight cotton boxers is the only way to sleep. Once I switched I never went back. 

With that being said, don’t forget I now live in the hot steamy sultry south with serious hot flashes and a titch of extra weight. However, lately I’ve taken my men’s boxers fetish one-step further. 

Let me explain, nine months out of the year, I wear billowing cotton summer dresses, which creates an embarrassing problem. 

My thighs rub together and I get horrific red-itchy-rashes. After one wretched inflammation, I had a brainstorm and decided to go back to basics. 

Like today. Instead of wearing my cotton granny panties under my flower print sundress, I have on cotton wide-leg Hanes boxers for inner thigh protection and gratifying continuous airflow. 

If that fact labels me…then…. Hello. My name is Pamela and I am a cross-dresser.

 

 

 

 
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