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Of course I didn't, especially when she said I didn't have to use a condom. She didn't like the pill, as it killed her libido, which as far as I was concerned was like giving Einstein stupid pills. So we used condoms (and went through a box a week), but I jumped at the chance to go bareback, even if it meant getting a little messy.Her period came on a Friday, and I spent that night and Saturday with my cock buried in her soaking wet pussy - as good as the sex was before, this was like nothing I had ever experienced. We both got a little bloody, but we'd just jump in the shower and go at it again with the hot water washing the sweat from our bodies, and then making us sweat all over again. Sunday, the bleeding stopped and the rubbers went back on.And then two days later, they came off again. She was talking about how good it felt without them, and about how, three days into her cycle, she was still pretty safe. So she asked me to just fuck her bare for a minute, then pull out and put. The tight fit of the blouse distracted her from noticing that the usually loose skirt was now visibly complimenting a firmer, more shapely backside.She was never one to dress in any revealing or provocative manner. The choice of shoes today was just a small step out of character, but not noticeably. As a mid-level corporate attorney in the contracts department of a New York law firm, Caitlin was known for her professional attire, professional demeanor, and professional accomplishments.Because of this she served as a mentor to several of the young female law students interning at the firm. Hearing the mantle clock chime, she headed out to get to the train for her daily commute.She often enjoyed the scenery on the trek down from her home in Tarrytown down to Grand Central Station while spending time getting a jump on the day with a bit of work on the train. Today, however, her thoughts drifted, trying somehow to make sense of last night's dream. She normally didn't recall any of her.
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“You don't have to rush off, I will only be a couple of hours.” I smiled at him and said “I need to change. I will head home and you call me when you get back.” He smiled and headed into his room. When the door was closed Barbara exploded with questions. They were basic information, just getting to know me. I asked what she does for a living and she said she works as an Administrative Director and told me the company. I asked if she was married and she laughed and said “I was, once, if you want to call it a marriage.” I asked “What do you mean?” She smiled and said “He cheated, lied, emptied the joint account and took off with a neighbor.” I was kind of stunned and said “How did she could she possibly compete with you?” She started laughing hard and said “She was a he.” I almost choked on my coffee. I recovered and said “Wow.” She laughed and said “If you think I was shocked you should have seen his parents.” I nodded, having no idea what to say. I could not imagine it, having no.

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