1. Riding the Jessie Train


    Date: 6/14/2015, Categories: Fantasy, Anal, Ass to pussy, Blowjob, Cheating, Consensual Sex, Group Sex, Hardcore, Males / Female, Threesome, Wife, Author: dpingjessie69, Rating: 92, Source: sexstories.com

    when we double-stuffed her the first time. We had agreed that high heels were a necessity for Jessie in these types of situations. While Jessie was in the bathroom, the atmosphere in the room was even more awkward than when I had sat in a stranger's house with Jessie's husband two Christmases ago before my first threesome. At this point, I knew literally nothing about Andrew anymore and didn't really care to find out. I just wondered how far this meeting would go and what Andrew was willing to do. Jessie had said one more was on the way, and obviously we were all going to fuck her. I thought it was fair to consider it a gangbang at this point, but would we all just take turns or would these guys be down to double-penetrate her? Would I even be comfortable going that far with these guys? Would they want to take it even further, to a level at which even I was uncomfortable? With all these thoughts racing through my mind while Jessie was taking way too long in the bathroom, as girls do, there was a knock at the door. I really have no idea if we waited for five minutes or an hour -- I completely lost track of time, reminiscent of Jessie's and my first group sex. At the knock, Jessie bolted from the bathroom, stumbling a little in her high heels. Her makeup appeared to be about half-finished, so I knew I'd get to enjoy several more minutes of uncomfortable waiting, only with two other guys instead of one. At that moment, as Jessie opened the door, I started to entertain the ...
    thought that it was another girl waiting to be let in, a thought that got me excited. That excitement didn't last long. The opening door revealed Ben. I hadn't seen Ben in about six years and was happy with that arrangement. I was not surprised that he would show up for a gangbang, though, and I was actually not happy at all that Jessie invited him to fuck her. Ben was a creep for as long as I had known him, and I was sure that fact hadn't changed over the years, especially now having seen him with that disturbing grin on his face as he showed up for a group fuck of one of my best friends. I guess I was being pretty judgmental though, since I was there for the same reason, but I digress. Jessie would later explain that, much like when she first invited me to join her and her husband, she thought it would be hot to invite multiple guys to fuck her in one session and see where it went. We never really justified this one in the context of her marriage, though, since her husband was absent, but I was there and ready to go, so it was easy to just not back out. We later figured that trying something even more debauched would give us a story worth telling instead of the same double-penetration story again. Maybe I was biased because of my friendship with her or just the fact that she was my type, but Jessie was a really hot piece of ass and very popular on top (because?) of it. I knew it wasn't a stretch that she could scroll down her contact list and randomly find a few guys who would be ...
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