1. Neighborhood Mom, Part I

    Date: 6/10/2017, Categories: True Story, Author: luvsumcameltoe, Source: sexstories.com

    I will refer to her only as C. I was in my teens, and inexperienced having grown up in a very strict Christian family. From a young age, I was good with computers, and a bit of an entrepreneur at heart. It didn't help me in any high school popularity contest, but it did have other benefits. Through a friend that knew our family, I was introduced to C. She was in her mid forties, and after getting laid off from a job that had spanned most of her career, she opted to start her own business - an internet service provider. Not knowing much about computer technologies, she had hired a young alpa-geek - older than me, but still young (early 20's maybe). Like many techies, he turned out to be unreliable and one day C called me desperately needing help with a non-responsive server. Over a few months, I assisted C on a fairly regular basis. She lived in the next subdivision over, and operated her business from her home. I would come over late in the evening once or twice each week to tweak and maintain her servers (it had to be done late at night because you couldn't take away people's internet access during the day to do this kind of maintenance). Eventually, we connected on instant messenger, so she could ask me questions when I wasn't there. As time went on, we would chat more and more about personal things - our lives, families, etc. She had 3 children, 2 of which were grown and had moved out. Her youngest daughter, then about 16 still lived at home. She was long divorced. ... Gradually the conversation dipped into more...interesting...topics, as tangents, but briefly and then they would return to more benign topics. For example, a witty sexual innuendo in response to something might lead to a "have you ever done that?" sort of question, which might prompt a few follow up questions or comments, but then return quickly to whatever topic had been at hand. Through these IM conversations, I didn't really get the sense she might fancy me, but being young and incredibly chronically horny, those brief conversations still turned me on. At least half the time, I probably was the one taking the conversation to the tangent. Often after an exchange like that, I would masturbate while carrying on the continuing conversation. At one point, I recall making a remark about the conversation turning me on, and asked if they did her too...she only responded with a wink emoticon, and then continued on the non-sexual prior topic. Occasionally she would remark that I was "the kind of guy she would want for her daughter", and I wasn't sure if that was mean to put me off. Sometimes these server problems would get complex, and from time to time I would end up working non-stop for several hours - sometimes till the wee hours of the morning. I recall at least a few times going over to her house in the evening to work on her systems. As I got exasperated with an issue, she would bring me drinks (she kept her fridge stocked with Pepsi for me), and generally be supportive. Noticing ...