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Lingerie led to dresses led to high heels led to wigsled to makeup, if you are reading this you know about the evolution of acrossdresser and have likely traveled the same path. There was a freedomand yes a sexual aspect to it.Growing up I was not particularly interested in the standard and overtmacho role nor was I effeminate. 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. “I’m surprised. You’re pretty good at this.” I said as she caught her breath.She gave me a prideful smile, “Thank you, sir.” she said, stroking my cock as she stood up and started to remove the t-shirt and slipped off her panties. Climbing on top of me again, she began to kiss me as she reached back to grab my shaft and rubbed the head along the length of her pussy. My head was soaked from a mix of her saliva and her juices. She began to prepare herself and right before sitting on it, she moved it back and sat down quickly, putting the entire length of my dick up her ass. It felt amazing but as she did this she let out a loud yelp of pain. Even though I didn’t want to stop, I felt I had to.“Are you ok?” I asked her.She seemed to grit her teeth through the pain, “I’m fine.” she rolled over so i was on top and she was on bottom. “Fuck me!” She sounded so insincere but at the same time happy to do it and sure that she wanted me to continue. As she said, I began fucking her, harder and.
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