Well the conversation later turned to crossdressers and transvestites. There had been something on the news that day about the gender restroom issue and we digressed to the Rupaul drag race show and how much a man could look so much like a woman with the right help and motivation. That’s when she told me that she thought I would look good dressed as a woman. I was kind of shocked at first that she would even say that. I mean no one knows I’m a crossdressing transvestite other than me. No one’s ever saw me that way except the ones that I had met in the past but then again they never seen me in guy mode either. So my true identity and my alter ego’s was never compromised. But in the same way I felt excitement on how she would respond if I told her my secret. It’s kind of like I wanted to tell her since I’ve known her for so long and knew my secret would be safe with her. I responded to her with something like, “Do you really think so?” I even said maybe you could be the one to do my. The worst part for me each week was when it was over. I hated that I would have to wait another week before I would get to do this again. I did not want to increase the frequency of our sessions though, I did not want the enjoyment to wane.Finished with my massage, I got up off the bed and her, set to leave the room. I went to her, to receive my thank you kiss. Normally, after kissing me, she’d fall asleep. Not this night. After our kiss, she asked me to stay. She wanted to talk to me again. I was scared that she did not want me to do this for her anymore. That would be the worst thing she could tell me.Shaking with trepidation, I sat down on the bed next to her as she sat up, her breasts jiggling enticingly as she rose. I got a thrill seeing that her nipples were still hard. Sitting up now, she turned to face me. It was a little strange, sitting here on my mother’s bed, with me still fully clothed and my mother completely naked. It took effort on my part not to just stare at her.
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