1. Old Friends Become New Lovers


    Date: 10/8/2019, Categories: Anal, Author: byMatt450, Source: Literotica

    It all started back in high school, but nothing ever happened until I was a junior in college. Andrea was the hottest girl in high school by far, but I never had the guts to ask her out. Mainly because I played soccer and she was a cheerleader, I figured she would never go out with me; and since we had been friends since kindergarten. Turns out I really should have asked her out, I missed a lot of opportunities for great sex. Anyhow, I was home from college one weekend and decided I would go hit up the local watering hole, since I had just turned 21 a couple of weeks before. Once I got to the bar I decided to survey the scene just to see if I knew anyone, there were only about 10 people there including myself and the bartender. Most of the people in the bar were in there forties I would say, but then I spotted Andrea and all my feelings for her came rushing back. I really had forgotten about her, because I had heard that she was going to some school in New York and we hadn't really talked in awhile. But there she was sitting at a table all by herself drinking a vodka and cranberry, she looked very sad and alone. I decided that it was now or never and started walking towards her; after getting myself a fireball and ginger ale and another vodka and cranberry for Andrea. "Hi, Andrea!! How have you been?" I said with surprise in my voice. "Holy Shit, Matt is that you? I have been okay" Andrea said, like she was surprised as well. "Yep, it is me. I thought you were living in New ...
    York?" "I was but..." she trailed off. "But, what? You don't have to be shy with me, I have known you for a really long time," I said. "Well my boyfriend cheated on me with my best friend/roommate and some other stuff," she said as she began to cry. "Well if he did that too you, he sure as hell didn't deserve you and she sure as hell wasn't a friend worth having. But I am sorry he did that to you," I said as I gave Andrea a big friendly hug. "Let's drink to stupid ex's," she said knowing I had a really dumb one in high school. "To stupid ex's," I said as we hit glasses. Andrea was dressed pretty sexy that night as well with a tight fit top that really showed off her beautiful breasts. But the jeans, WOW, they hugged her perfect ass and put me at attention the first time she got up, and I think she knew it too cause I swear she was swaying her hips just for me as she walked away. I would eventually find out later that she was doing it on purpose, cause she really wanted sex that night. That is how the night began it didn't take very long for us to start getting a little bit tipsy. Especially Andrea, since I think she was there for at least a couple of drinks before I got there. It didn't take us very long to start talking about high school and the fun that was had. Then it happened, I really had no idea it would happen but it did. "Matt, why did you never ask me out in high school?" She said with smile. "I....I...I never thought you would say yes and didn't want to ruin our ...
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