An Unexpected Evening - Sex Stories

An Unexpected Evening

Part 1

Sitting on my couch and looking at my phone, I find myself reflecting on an eventful Tuesday. This morning I broke up with my girlfriend of eight months, Lisa.

Lisa was a hair dresser that I had met when she was subbing in for my regular barber one day. I was in my mid-thirties and she was eleven years older. Despite the age difference, she took care of herself well. She was a 5'3" natural redhead and had a pretty tight little body, small breasts, full lips, a tendency to wear a little more makeup than necessary and a smoky voice that I thought was sexy. I asked her out when she finished cutting my hair and things moved fast after that.

It started out as an intense relationship for a few reasons. She seemed like exactly what I was looking for - someone who knew what she wanted and wasn't "high maintenance". It also didn't hurt that we were all over each other, all the time. It wasn't uncommon for us to fuck a couple of times a day when we had the chance.

Things started to go downhill after three or four months. As she started getting comfortable with us as a couple, it became clear that she wasn't as self-confident as she pretended. Turns out that she was actually remarkably insecure in many things. Our age difference, female friends in my life, our future, etc. That insecurity started manifesting more and more in drama that I just didn't want to deal with.

At the same time, the sex life was cooling off. One thing I had overlooked due to the intensity ...

... of the sex was that, well, her pussy was really loose. It was getting harder to get pleasure from fucking her because the physical sensation just wasn't there. I'm not saying it was like throwing a hot dog down a hallway but it wasn't anywhere close to tight.

I had asked her early on in the relationship what she thought about anal. She told me she wasn't into it and I reluctantly respected that. One night, about five or six months in, she was riding me and my cock came out of her pussy. She grabbed it to put it back in but rubbed it around her asshole to tease me a bit. I grabbed her hips and pushed upwards a bit and the tip slipped in. She froze but after a few seconds pushed down so that the head of my dick popped into her ass. She held me there for a bit and then pulled back out.

When she rolled onto her side, I wasted no time curling up behind her and pushing the tip of my cock back into her ass. She didn't fight it so I slowly pushed myself into her, pausing when her hand gripped my thigh tightly.

I fucked her in the ass that night, which started a new pattern that I enjoyed quite a bit. We would start having sex and at some point be on our sides. I would fuck her pussy for a while and then subtly reach over and put some lube in my hand without her noticing. I would thrust harder into her and "accidentally" pull out. Grabbing my dick with the lubed hand, I'd get it slick and then glide myself into her ass.

That was the pattern for a couple of months. We would ...