Hookup Stories

Seducing and Older Woman – Part 7

When I woke up the next day, I had a whole new outlook on my mother’s best friend. I suddenly knew what she was after and I really wanted to give it to her. That meant that I had to be in charge of everything that happened between us from them on. After I walked in on her masturbating in her room the day before, things had taken a very severe turn. This was a much older woman than me. She was my mother’s best friend and in her late 30s or early 40s. I was 18 at the time and I had always wanted to fuck this woman. I was deeply attracted to her and she was amazing in every way. Any time she came over to visit us, I’d take one look at her tight body and have to run to my bedroom to jerk off to her. I just had no idea that sometimes she followed me and listened to me pleasuring myself on the other side of my door. That was because she was just as attracted to me as I was to her. She told me all of this after she gave me a blowjob on the living room sofa.

We were on vacation

Both of our families were on vacation at a lakeside cottage. She was there with her husband and I was there with my parents. I knew that I wanted to take the opportunity to finally see her naked, but she took things to a whole new level. I ran into the cottage while everyone else was at the lake and walked in on her on the first day. She was naked in her room with her legs spread wide and magic wand vibrating her clit. She saw me walk into the room, but never even considered stopping and covering herself up. She just locked her eyes onto mine and came while I watched her. Just seeing it made my cock start throbbing so much that I had to run to the bathroom to jerk off. That could have been the end of it, but she had other plans. She just followed me right into the bathroom and made me give her the same show that she had given me. She watched me jerk off and made sure to catch my cum so it didn’t shoot all over the place and get us both in trouble.

She needed to feel sexy

It was later that night that I learned the information that I really needed. I was in the living room while she was out at a fire with everyone else. They came in to head to bed and she stayed back. She sat next to me on the sofa and told me how neglected she felt as a sexual being. Her husband simply saw her as the mother of his children and refused to do the things that she used to love. She was nothing more than a cock slut deep down and her husband used to love that about her. Now that she was a mother, she had to put those desires aside and that was what led her to fantasize about someone like me. She knew that I wanted to filthy things to her. She knew that I was jerking off to her on a nightly basis. She also knew that was the kind of sexual energy that she needed. She needed to feel like a sexual being that was deeply desired by men again. That was where I came in. She wanted me to use her for pleasure and nothing more. I did what I could the first night, but it wasn’t enough.

She was too tight

It turned out that having to give up her true passions for so long had reset her body. She loved nothing more than to be bent over by horny men and taken up her asshole and I can understand that. Having anal sex isn’t like vaginal sex. It’s primal and more passionate. Being fucked up the ass by a man means that she’s being used for pleasure and that’s what she loved. Having vaginal sex means that the man also wants to give her pleasure and that takes away that primal, sexual use. She had a butt plug in for a little while to loosen herself up, but it was just too tight. The years without any anal penetration had practically left her a virgin again. I tried to get myself in there, but it was just too much. All of the pushing and pressure sent me over the edge and I had to shove my dick into her sopping wet pussy to explode inside her. I know it wasn’t totally satisfying for her, but it was still close to what she was looking for.

She was ready again the next day

I woke up the next morning and headed downstairs to see everyone in the kitchen. She was wearing a tiny little tennis outfit that showed of every last one of her amazing curves. If you don’t know what a tennis outfit is, it’s pretty much standard issue for MILFs. It’s a short, pleated skirt with a button down shirt. She was wearing a visor on her head and her should length hair was in a ponytail. It took a few long minutes of staring at her before I noticed that everyone was dressed for the tennis court. It turned out that they were all headed to the tennis court for a morning games and I was free to watch them if I wanted. Normally, this would have been something that I passed on, but I couldn’t lose out on the chance to see her looking so sexy and jumping up and down all morning. I went along, but not before she let me in on her secret. She made sure that she was the last one out the door with me behind her. It was a very subtle gesture, but she flipped up the back of her skirt just long enough for me to see the bulge in the back of her white, lacy panties. Then she let the skirt flip back down and turned her head back to wink at me before heading out the door. That was when I knew I was in for a very special day. That bulge in her panties was the buttplug from the night before. She was clearly intent on wearing it all day long to really stretch out her asshole for me. She wanted me to try and fuck her up the ass all over again and I was more than happy to oblige her. All I had to do was get through the hot day and I’d be reared with a whole new night of taboo passion with his married woman. It was going to be difficult to think about all day long, but that was my mission. I had to be discreet about it and not let everyone else know that I had a raging erection the entire time I watched her dance around the tennis court. It was the most difficult every time I saw her skirt flip up in the wind and I knew that I was the only other person who knew our secret.

I couldn’t wait

The problem was that I just couldn’t wait that long. There was a brief lull in the playing and she plopped down next to me on the bench I had been sitting on. She was glistening with sweat and even sexier for it. It was too much for me and I made up my mind. I gave her a very deep look into her eyes and got up to walk to the public restrooms by the court. I didn’t look behind me because I didn’t want to give anything away to anyone who might had seen, so I had no idea if she had even followed me. I got out of sight and finally turned around to see her coming up behind me with a smile. I grabbed her by the arms and pressed her against the wall to shove my tongue into her mouth. She happily sucked it in and we kissed each other with my parents and her husband just a few feet away. That was when I made my first move to take over and be the man that she needed.

More next time

I’ll have more to say about this next time. We had a very fun day and there was a whole lot going on between us. I knew that I wanted her more than anything and it seemed like she wanted the same thing. I’ll get into what happened behind that public restroom and how it cemented this older woman as one of the best hook up I’ve ever had the joy of experiencing in my entire life. She’s an amazing woman and I love to remind myself of that.