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I stood in the middle somewhere.Growing up in the 1960's gender roles were massively enforced andstifling; the fear of being outed was palpable. Men's clothing was, andis, purpose driven, rough, confining and restrictive in all aspects; theform and function of it was strictly enforced as though it was auniform. Women's clothing on the other hand was about freedom andbeauty. Men's clothing is boring; women's clothing exciting. Womenexpressed themselves through their clothing, men weren't supposed toexpress themselves at all.All through my teenaged years my crossdressing experimentation continuedand expanded but was limited to what of my mother's clothing I couldactually fit into. I had to be careful to fold and place the clothingback exactly as I found it but I took the risk of being found out for Ihad to satisfy what was to become a lifelong crossdressing compulsion.At one point my mother figured it out and discreetly asked me to stayout of her dresser but didn't press the issue any. Her matter-of-fact tone and actions lent innocence to our actions, but there was no doubting the fact that I was accompanying a beautiful mature woman to her hotel room – not something a 22 year-old can ignore, or take for granted. When Megan opened her room door an entered she didn’t indicate for me to follow her, but I did so just the same. No matter what this was about, I knew that I was supposed to follow. Once inside she placed her purse on one of the two soft chairs beside a small table. The Hotel room was standard, upscale for sure, but not luxury. The bed was pristine with lots of pillows of different sizes. There was a small suitcase on a stand and a few small artifacts Megan had left around. Unsure where to sit, I stood and watched as Megan bent down to a small refrigerator and pulled out a bottle of wine. She found a couple of glass tumblers and held one of them up, along with the wine. “This okay?” I nodded and she indicated I should sit. I sat on the edge of the bed. .
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