Hookup Stories

Seducing an Older Woman – Part 9

I told you before about the time I hooked up with a much older woman. It wasn’t just that she was older, though. What was really fun about it was the fact that it was my mother’s best friend. This was a woman that I was attracted to for many years. She would come over all the time and I wouldn’t be able to stop staring at her. In fact, a lot of times she was there, I had to run up to my room to jerk off as hard and fast as I possibly could. She just turned me on that much. What I didn’t know at the time was that this woman was just as attracted to me. She confided that she always knew what I was doing when I went to my room. In fact, sometimes she would follow me up and listen to me stroke myself through my door. The thought of an 18 year old guy cumming to her turned her on so much that she would usually end up doing the same thing as soon as she got home. Things could have gone on forever like this, with the two of us masturbating to each other over and over again, but she decided that she wanted something more.

We went on vacation

Things all came to a head when we all went on vacation together. It was me and my parents along with her, her husband, and her kids. They were younger than me, so I didn’t really have anyone to hang out. That’s probably why I decided to make it my job to at least see this woman naked while we were all staying together. It was a lofty goal, but I was sure that I could make it happen. I just didn’t expect it to happen so quickly. Most of us were down by the lake on the very first day, but she stayed behind. I had to take a bathroom break, so I made my way back to the cottage. I was just finished pissing when I heard a strange noise coming from down the hall. I had no idea what it was, so I followed it. TO my surprise, it let me right to her room. I slowly opened the door and was greeted by the site of her totally naked and energetically masturbating with a magic wand.

She let me watch

I was shocked at what I saw and horrified when she heard me. I thought I was going to have to apologize to her and that I had just ruined everything by violating her privacy. Fortunately, things didn’t work out that way. She saw me standing there and just took a second to realize who I was. Once she knew that it was me and not someone else, she just locked eyes with me and let herself cum. She made a lot of noise and looked right at me with a smile on her face for her whole orgasm. I just stood there and watched it, loving every single second of it. When she finally stopped cumming she turned off the wand and put it down. She simply and softly told me that I now owed her a show of my own and turned over to relax. That was my cue to leave. I quietly closed the door and made my way back down to the bathroom. There was no way that I was going to be able to watch all of that and not have to immediately jerk off to it.

She followed me

I was just sitting down on the toilet with my shorts around my ankles and my dick soaped up and in my hand when the bathroom door opened. It was her and it turned out that she was already there to get her show from me. She closed the door behind her and just stood there to watch me work. I was embarrassed and extremely self-conscious, but I still did it. I really figured that I owed it to her and it seemed like something that she really wanted to see. I just sat there and did everything that I would normally do in this situation. The only difference was that I was looking up into her eyes the whole time. I don’t know if it was something she wanted to do or if it was just to make sure the floor stayed clean, but she paid attention  to when I was about to explode and caught all of my cum as it shot out with her bare foot. She took it all and didn’t lose a single drop. Once I was finished she just cleaned it all off with toilet paper, dropped it into the toilet between my legs, and left. That was the first time I ever jerked off in front of someone.

She laid it all out for me

It wasn’t until later that night that she told me everything that was going on in her head. It turned out that she had been lacking in the kind of sexual passion that she needed for a very long time. She was the kind of woman who liked it rough. She also liked it when men used her and degraded her. She loved the humiliation but had to live without it ever since she gave birth. After that big change, her husband stopped looking at her like a sex object. He started looking at her like the mother of his children and was unable to treat her the way that she wanted to be treated. That’s what led her to me. She knew that I wanted her. She also knew that an 18 year old would be more than willing to treat her like a piece of meat. She came up with the entire idea of taking a vacation just so she could get what she wanted out of me. She told me all of this on that very first night and then begged me to fuck her up the ass. That was, unfortunately, something I was unable to do that first night.

She was too tight

After years of never having her anus penetrated, it had closed back up nice and tight. I tried to fuck it, but I couldn’t get inside. All of the pressure of trying was too much and I couldn’t stop myself from cumming. She asked me to just shoot it into her pussy and that was the end of our first night together. The next day brought a whole new opportunity. She really wanted to get what she needed and she put in the effort to make it happen. She spent the entire next day with a butt plug in her asshole. She even flashed it to me so I could see it. That wasn’t all, though. She was playing tennis with the other adults when I just couldn’t take it anymore. I called her over behind the public restrooms and pushed her down onto her knees. I knew that it would be something she liked and she responded in kind. She gave me a blowjob right there, just a few feet away from my parents and her husband. She even jerked me off onto her tits and buttoned up her shirt to keep it there all day long.

I was intent on giving it to her

I was pretty much falling in love with this woman at this point. She needed a man to take her and I was going to make sure that it was me who did it. I didn’t care about her husband or what would happen if anyone found out. He wasn’t giving her what she needed and I was going to step in and do it. I was leaning against the wall of the public restroom after she made her way back to the court and thinking about just how I was going to make that happen. I kept running the scenarios through my head until I came to one that might just work. It seemed really simple and wouldn’t take much at all. I waited for some time to pass so no one would get suspicious, then I made my way back to the cottage. It was going to be a lot easier if I could do what needed to be done with no one around.

More next time

I’ll let you know what happened next time. This is still a story that I love to tell. It brings up a whole lot of points that I care a lot about. You should always be aware of what the women you’re with needs. If she goes out of her way to make you happy then you have to do the same exact thing. It doesn’t matter if she’s the mother of your children or a random girl you’re hooking up with. Give her your very best and she’ll do the same for you. It’s really that simple and it’s something that we should all be doing for each other, even when it has nothing to do with sex.