Crossdressing, Why Me? Ch. 05

After Ryan and Megan moved out and were settled in their own lives it was Terry and I, things were good for quite a while then Terry started to become distant, his mind elsewhere, his interest in me sexually no longer there. He was quickly losing interest in me, his eye roaming, looking at other men, feeling like he had missed out. I quickly realized he was seeing other men on the side, after my ordeal with Scott and the other Terry I was not going to stand in his way of his exploring his options, but he would not be living with me or sleeping in my bed anymore. Terry would get himself a one bedroom apartment on the other side of the city, he had met a younger guy he was interested in and hoped to pursue a sexual relationship with this young man. I helped set Terry up in his new place, he and I would be friends, but not close ones, it was to weird to watch him with other guys around. Terry and I let the kids know we were going to separate their Dad moving out of my house. Terry and I

Just after I graduated high school, my dad told me I had to get a job, until I started school in the Fall, and had to remain employed, or move out. At this same time, my stepmom decided she wanted to open a hair salon with my dad's money and offered to employ me to do all the odd jobs that needed doing around the place - sweeping hair, laundry, mopping floors, cleaning the bathroom, maintaining all of the equipment, and even covering for the receptionist when she went on her breaks. It was a lot to do, and it kept me very busy. But I enjoyed it a lot, as I got to talk with some very nice older ladies, and the beauticians my stepmom had hired were very friendly, too. As I avoided the more aggressive, cougar-type customers, I worked on seeing how close I could get to one of the pretty hairdressers closer to my age. My stepmother, however, had other plans for me. I have to say that my dad must have had a thing for the bimbo look, because that's just what he married. My stepmom i

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The following is the fourth part of James' exciting weekend with his cousin's twenty-something daughter. To understand the full context, you should probably read the first three - chapters 11-13. Portions of this weekend were taken from my previously-published work from over a decade ago, with names changed and details added. I just felt it was a better fit for this storyline. *** Some time around four or maybe five in the morning, James awakened to realize that he was living every man's fantasy. He was hard as a rock, his dick felt warm and wet and was feeling very good. He heard the sucking noises and it didn't take long to sink in. Megan was giving him head? 'Slurp! Slurp! Slurp!' His beautiful cousin slobbered hungrily on his arousal. He clearly felt her lips wrapped snugly around his shaft and gliding up and down steadily. He could feel his hardness poke the back of her mouth each time she sunk him deep. Her head bobbed up and down on his lap, gobbling up

I realized that Craig might ask me to stay the night, but I thought that might be a little much. Whatever we'd just done, it was still a first date. Staying over would probably mean morning sex, and perhaps more puzzling behavior from him. And I was far from ready for any of that. But he asked, almost as a formality, and when I declined, he didn't argue. We watched the TV news, including clips from the Cubs game, while we ate the cold remains of our supper. Afterwards, he drove me back to my apartment. I kissed him before I got out. He still smelled faintly of my juices. "Can we see each other again?" he asked hopefully. I suspected from his tone that he was expecting an ambiguous reply, like 'I'll call you', or 'maybe sometime', that would mean 'never'. I wasn't certain that I wanted to date him again, but the poor man had gone so long without sex, and he'd tried so hard to please me, I couldn't disappoint him now. I had to l

Crossdressing, why me? Read on and you'll find out why. Firstly, before I begin my recollections, may I once again state they are true, not a fantasy. I have been both cursed and blessed being a crossdresser but my sex life has been brilliant because of it. The conversations are maybe not exactly the whole truth but near enough to give you the reader an idea. "I'm cumming" Michelle screamed, and with that a fountain of creamy love juice shot up like a fountain from her beautiful clitty. It kept on coming, landing on her pretty pink lace topped stockings and matching lace panties. Finally it was just a dribble. She used that to lubricate herself as she continued to wank her clitty. The same clitty I had experienced a few weeks earlier. Oh, how I longed for it again, to have it in my hand, my mouth and then up my ass. All the time her piercing green eyes were staring at me from my computer screen. She was beautiful, she really was so very convincing as a female, except