1. Kaylin, A Seemingly Innocent Encounter

    Date: 5/29/2024, Categories: True Story First Time Latina, Male/Teen Female Mature Older Male / Female, Oral Sex Teen Virginity Young Author: markerss, Source: sexstories.com

    It really wasn’t suppose to happen, and even though yea, I thought about it, hoping it would, I knew deep down I shouldn’t pursue it, because afterwards, I worried about what we had done.
    She was a very attractive, Latina student, probably around 18 or 19, with long dark wavy hair, and even though she wasn’t in one of my classes, I did see her a lot. Most of the time she dressed very casual, wearing a pair of blue jeans and a top, but there was a few time when she wore these off-white knitted legging that really showed off her cute little butt.
    Over the next few weeks, I deliberately tried to position myself, wanting to run into her. She was really so naïve I thought, and wanted to know her name, I eventually asked this one time when we happened to be talking. Seeing that great smile, and her petite little body, super cute figure, I nervously smiled and asked, “What’s your name?”
    It surprised her I think, but then telling me her name was Kaylin, we shook hands, and I introduced myself. She seemed to know who I was, and being she was only about five feet tall, and I was more than six feet, I kind of towered over her, which I think made her a little nervous. I was nervous too, and being a little tongue tied, there was an awkward pause as we stood there waiting for the other to continue the conversation. It was only for a moment, and when she gave me a smile and said, “I gotta get to class,” we again shook hands.
    “My god,” I thought, “she was so pretty,” and as she ...
    ... walked away, I couldn’t help but look at her little butt, in those knitted leggings she liked to wear, thinking, “I should have said something.”
    I wanted to ask her out, but how, and as I continued to search for a way, I said to myself, “Next time.”
    Yea, I was a lot older, more than twice her age, being I was in my late forties, which I knew was going to make it difficult, but seeing her and being able to interact with her, always had me think just maybe, but the age thing was always there.
    I really couldn’t get enough of her, she was so young and friendly, in a naïve way, and everyday, I found myself looking forward to seeing her, to the point where, I again would deliberately try to run into her. I liked seeing her and talking with her as much as possible, wanting to innocently flirt with her, but I always knew I needed to be careful to not appear overly flirtatious. I really hoped she’d get the idea just how interested I was, and maybe unknowingly she actually did, but I think the differences in our ages was always in the back of our minds, which made it difficult to act upon our feelings.
    It was really nice, she always made me smile, which constantly had me trying to think of a way to somehow be with her, but then again, there was noway. I was becoming obsessed with her, continuing to to want to see her, always looking for an opening to ask her out, but how?
    However, this one Friday afternoon as I headed home and I passed by the front lobby, there she was! I ...