Like our sessions on the couch, this had progressed over time into an intense petting session. She’d let me slip my hand inside her panties as we to...gue-kissed with closed eyes. I parted her labia and then worked my finger in-and-out of her moist pussy. I mistakenly thought this was how girls masturbated. It must have been during one of these sessions that I unwittingly popped her cherry. If she felt it, she said nothing.I loved feeling her warm pussy encircling my finger and assumed she was. I put my makeup and wig on. I felt so sexy en femme. I just couldn’t believe I was getting a chance to crossdress and not have to worry for a while as my mom was at work. I just ended up crossdressing, doing the things I normally would, which felt so good hearing my heels and hose rub together and my heels on the floor when I would walk.After a bit I decided to go out into the hall way for a bit and see how far I could get without anyone paying any attention to me or even noticing me. It. I hadn’t known that almost all the available men had married. I had been vulnerable because I’d been working so hard that I’d had no time for women except as colleagues. Janie hit me like a tidal wave and I was lost.National Nude Day was near. Janie had an idea that she didn’t discuss with me. If she had – I would have refused to co-operate. She wanted to show everyone that she owned the man with the biggest tool in town. She didn’t expect me to parade down Main Street with my asset on display. Yes, I could have ordered her to do something new, but I would rather her think it was her idea. I could be subtle, but I always got my way, eventually. The shortest implementation when she was hesitant at first was an hour. The longest implementation was a few years.Occasionally, not very often, she would bring up an idea for me to consider. If I didn't like it, we didn't try it, and if I did like, we tried it. I knew that she was about to suggest something when she would start off saying,.
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