1. Those with Experience Apply


    Date: 1/19/2016, Categories: MILF, Author: mikej007, Rating: 9, Source: LushStories

    A while back a female friend of mine, Sarah, continuously talked about a co-worker she had who was from New York. This lady, Jacky, was a bit older than all of us. She was in her late forties, and was "that person" at their work who talked about everything and didn't seem to have any boundaries. Some of the stories my friend would tell about Jacky were stories she would hear at work, like how Jacky used to hike secluded trails topless when she was younger, how Jacky discussed sexual preference changes from the 80's, 90's and 00's, and stories of Jacky's many sexual encounters with 80 hair metal bands. These stories were always fun to hear, and I always wondered who this Jacky character was. One day I finally found out. As our crew left on a Friday night to go see a local band, Sarah mentioned that Jacky overhead her talking about the show at work and might be meeting us. Jacky was already there when we arrived. In looking over her, it was hard to believe she was in her late forties. Jacky had long black hair, a great figure, and breasts that were about to pop out of her low cut blouse. As the night went on, we all saw Jacky in action. She talked nonstop. Within an hour we all knew she was Italian, lived in Brooklyn, moved west in the 90s, had a daughter in college, was liberal in her political views and tons of other trivial information. I eventually tuned out and watched the band. Later that night, I met up with my friends again, and noticed that Jacky was still talking. ...
    Within a few minutes she let us all know that although she wasn't drunk, she probably shouldn't drive home and asked if someone her drive her home. All of us were planning on cabbing it home, but Jacky insisted that she couldn't leave her Jetta in the bar's parking lot over night. I explained that I could drive her home if needed, and then would take another cab home being that I lived the closest to where Jacky resided. In the car ride back to Jacky's house she started running her hand up and down my muscular arm. Showing off her lack of boundaries, she mentioned that she hadn't had sex in a while, and the next guy she slept with was in for a treat. I playfully asked her to elaborate, and she did explaining her "no-holes barred" philosophy on sex as her hand started to crawl across the seat belt and onto my hardening crotch. When we finally reached her house, she asked if I was feeling lucky. I was already half way out of the car with all the intention of fucking the shit out of her. Very little words were spoken for the next hour, an event that led to a series of fun times with Jacky. As soon as we got in the door, I pushed her up against the wall and starting kissing her passionately. I ran my hand up her skirt, grabbed her panties and ripped them off of her, throwing the fabric to the floor. Grabbing her pussy as we kissed, my fingers ran in and out of her wetness. She reached to unbutton my pants and grab my hardness, stoking me as I fingered her. Pushing me back, Jacky ...
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