1. GOOD LUCK WITH TOMMY


    Date: 8/15/2016, Categories: True Story, First Time, Older Female / Males, Author: Lostlady, Rating: 93.4, Source: sexstories.com

    be out of high school, what college was he going to go, what was he going to study, and things of that nature. Then I slid in the question that was bothering me. “Any girlfriends, Tommy?”, I asked innocently, already knowing the answer. He paused before answering, then “No, not really, at least not the way you mean it. I guess it’s like that old saying, I’ve friends who are girls, but no girlfriends” “Well, how can that be, you seem like the type that they’d flock to. You uncomfortable around them or something like that?” “No, not exactly.” He paused, looking at his glass as if there was an answer there. Then he looked at me, “I get along fine until I get by a girl that I really like, then I turn into a kind of idiot.” “How so?” I asked, deciding to press the issue. “I get nervous, I guess. You know. I can’t think straight and wind up making a fool of myself.” He shrugged his shoulders slightly. It was beginning to make sense now, no confidence. He’d probably been rejected a couple of times when he was younger and never got over it: what a shame. “Well, you have no problem talking with me, so I guess that means you don’t like me?” His head dropped for a moment before he realized I was just teasing him. Then he looked at me again and smiled, “There’s no good answer to that. If I agree I insult you and if I disagree I come off looking like a 19 year old horn dog on a MILF hunt.” “That’s a good answer!” There’s nothing at all wrong with this guy, I thought to myself, nothing ...
    that his first woman won’t fix. But, if he’s this shy, it could be a long time before he gets lucky. Then the obvious answer came to me, I could be that first one. At his age I doubt if he could turn down a sure thing, and if he did back out, just being offered would probably be a boost to his ego. At his age, a 36 year old may have seemed like an old lady, but I was not an unattractive old lady, I figured he’d go for it. But how to go about it. I decided on the direct approach. I got up and walked around the table and stood in front of his chair, looking down at him. “Stand up, Tommy.” I said calmly, even though my heart was racing. He looked up as if he thought I was angry about the MILF remark, nothing could be farther from the truth. In fact, that was what gave me the idea; lucky him, lucky me, lucky us. He rose up nervously and stood in front of me. I reached up with one hand behind his neck and pulled his head down gently and kissed him lightly on the lips. Then with our lips inches apart I asked quietly, “Do you really think I’m a MILF?” He didn’t answer and I didn’t care. It was on to the next step. Sliding my other arm around his back while I leaned against him, I pulled him tightly to me. Then I kissed him again, this time hard with my lips slightly parted. He kissed back but his lips were closed, no matter, he’d probably never kissed anyone before. I stiffened up my tongue and slowly pushed it into his mouth. His reaction was immediate and drastic: it was as if every ...
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