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Jim included – until we girls began an evening of lovemaking that ended with Jim jacking off on our spent bodies."Diane could see Ann squirming a bit as she told her story. "Jim and I took a big step earlier this year. He had become accustomed to dressing up for me as "Jamie" and allowing me to wear a strapon and fuck his ass. I started off slow using my finger when I would give him head. Eventually I probed his ass with a dildo and he never said a word. The night I told him I has a surprise for him, I knew he was shocked when I came out of the bathroom with a dick swinging from my hips. But he didn't resist as I slid the head into him and began to take his cherry. I fucked him steady and jacked his little dick with my hand until he came all over his stomach." I knew soon that he was ready to become the woman I wanted him to be. I had been giving him morning vitamins and had recently had a friend of mine provide me with a hormone regimen of estrogen and another pill that inhibited his. Lo and behold, after I had taken the message for her, I walked towards her desk and placed the message on her chair; the bespectacled gentleman glanced at me when I walked passed him. He tries not to be obvious about it. I have noticed that he was staring at my breasts. I was wearing an olive colored jersey knit long sleeved shirt with a demure A-line skirt with flats. The outfit was very conservative, yet it showed off my curves very nicely in an understated way. Since he had noticed me that day, I never could stop thinking of him.One day, we were in the elevator together. Everyone has those awkward moments in an elevator. We were both feeling very awkward. He was more so than I was. He was staring at my low cut blouse but he quickly looked away. He had his head down. He felt a little uncomfortable. He was avoiding eye contact and I politely asked him "how are you today sir?" he said “alright and yourself? “ So I responded, “I can’t complain.” Then the elevator door opened.
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