1. Pizza, Baseball, and a Bet

    Date: 4/13/2018, Categories: Wife / MILF, Author: byherfan, Source: Literotica

    This is another story about experiences with Jill, my first long term girlfriend and sexual partner. They are based on true events except that they are revised into a much more positive, pleasurable outcome. If we'd known then how to have a relationship good enough to do the things we could have, then maybe things could have turned out better. *** Jill and Jenny Jill and I were going through a rough patch. We had been together for a few years but it seemed we had different views of the future. She wanted to get married soon but I wasn't ready. She thought that seeing other people was the way to figure out if we had something good enough to wait for, or maybe it would help me get ready. Jenny, Jill's sexually enthusiastic cousin, was in for a visit. (The same Jenny from "What Might Have Been") The two of them would get out at night after their family obligations. On the Sunday Jenny was leaving, Jill invited me to come over that night. She had things to talk about. This sounded bad. When I arrived, she was dressed in very short denim shorts and a white gauze top that buttoned up. I could see she wasn't wearing a bra. I was not expecting that. It had been a while since we'd had sex, so I was happy for the show, whatever the reason. I reckoned that she had been out with Jenny, which could mean most anything. She told me she had some explaining to do. She continued, "When we broke up, I planned to have sex with lots of guys. I wanted to have some fun, but I also wanted to ... hurt you and make you jealous. After talking to Jenny and thinking about it for a while, I decided I shouldn't use sex to hurt you when I could use it to bring us closer. It didn't make sense to do something to hurt you that I wouldn't do to make you happy. So first, I'm going to do you any time you want it. I know we're not over all our issues yet, but I'll probably make you give it to me even if you don't want it. I hope you don't mind. It's OK though; I'll take some of the responsibility for making sure you want it. Next, I'm going to tell you a story. This story is either completely true or completely untrue. There is no middle ground. There are a couple of conditions, (1) I'm not going to tell you which it is, true or untrue, and (2) I'll only tell you during sexual activity. Once you come, we have to stop until the sex begins again. Any type of activity is ok, and I'll do a lot of the work since I'm telling the story. I might even have a few new tricks to try on you."As she spoke, she walked around the room and kicked off her shoes. She continued talking as she slowly unbuttoned her top to the point where only one button remained. "For two nights in a row, Jenny and I had been talking to a couple of guys at the pizza hang out. One was the regional manager and the other was the local guy. Jenny mostly flirted with Dave, the regional guy, while the other one, Steve, showed me lots of attention. Sometimes though, Dave would get very close to me if Steve and Jenny were ...