Hookup Stories

Seducing an Older Woman – Part 10

I had just gotten a very satisfying blowjob from my mother’s best friend and now I was alone in the cottage. I had a job to do that night and I was going to be sure that I did it. This woman wanted to feel like a woman. She wanted to be taken by a man and she wanted it to hurt. She wanted me to fuck her up her asshole that was so neglected by her husband that it had practically regained its virginity. It was extremely tight and my first attempt at penetrating it ended in failure. It felt too good trying to get into it and I ended up having to blow my load in her pussy instead. She was nice about it, but it was obvious that she was let down. Tonight was a new night, though, and I was going to make it happen. All I had to do was sneak into my parents’ room and find my father’s stash. I don’t know if he had them for fun or if he needed them, but he always had his Viagra with him whenever we went on trips. That was what was going to make all of the difference that night.

They were easy to find

While I was expecting to have to work to get them, they were actually pretty easy to find. They were right at the bottom of his sock drawer. I pulled them out and just looked at them for a few minutes. I had no idea how to use them and I was half expecting to see directions on the bottle. No such luck, though. That was the day that I learned prescriptions don’t always have the information that you need on them. I opened up the bottle and there were plenty of them in there. They were really tiny, though. I thought that taking one might not be enough for me. The last thing I wanted was to go into this whole thing with a false sense of security and blow the whole thing again. I was mulling this all over when I heard the front door open. I heard all of the adult right away and I had to act. I shook the bottle and four pills fell out onto my hand. I quickly through it back into the drawer and ran out of the room and into the bathroom to hide.

I had no choice

My original idea was to keep the pills until that night and take them right after everyone went to bed. That plan was in jeopardy now. Someone knocked on the bathroom door. I was in trouble now. I couldn’t walk out that door with the pills in my hand. Someone would see me. I just shoved all four into my mouth and swallowed them as quickly as I could. I even used water from the bathroom sink so whoever had knocked would hear it. I felt it all hit my stomach just in time for the person to knock again. I opened the door and saw who it was. It was my mother’s friend and she was happy to see me. She quickly snuck into the bathroom with me and quietly closed the door behind her. That was when I realized what kind of knock it actually was. It was a quiet knock like she was trying to get my attention without letting anyone else know what she was doing. She was giddy to be in there with me and very quietly whispered into my ear that everyone else was going out to start a fire. She had apparently used the bathroom as an excuse to stay behind with me. She told everyone that she was feeling a little sick and would meet them outside if she could. If she couldn’t she might just go to bed.

It was a brilliant move

I couldn’t help but wrap my arms around her and pull her into me for a kiss. Her husband was still downstairs and it felt naughty and wrong. That’s probably why it turned the both of us on so much. I wanted to give her a gift and I knew exactly what it should be. I turned her around and held her close to me from behind. I slipped my right hand under her skirt and pushed her thighs apart. She hadn’t been wearing panties all day long, so I knew I wouldn’t have to worry about them. She was soaking wet down there and my middle finger easily slipped right inside of her. I also used my thumb to gently rub her clit at the same time. She let out a quiet moan and I immediately used my left hand to cover her mouth. That would make it easier to make her cum without alerting anyone.

I made it good

I stood there with her in front of me and worked her pussy with my hand for five minutes. I was being intentionally gentle with her and she was responding to it. Her hips were moving and I could feel sweat glisten on her back. I kissed her neck and lightly bit her back while I worked. Then I finally heard it. The front door opened and closed. I could faintly here everyone’s voices coming in through the window from the outside. We were all alone and it was just what I needed. This wasn’t a girl wanted it gentle. I was just torturing her with it. I was working her through her levels of pleasure and keeping her right on edge while the house was full. Now that it was empty, I could push her over that edge. I uncovered her mouth with my hand and wrapped it around her throat. I closed my fingers around it just enough to control her breathing. I kicked her legs apart with my foot and shoved two more of my fingers deep inside her. I started hammering them in and out of her as she struggled to stay on her feet as her legs bucked and shook.

I found out she was a squirter

Hammering my fingers in and out of her pussy also meant that I slamming palm against her clit over and over again. She was already on the edge when I started doing it that way and it didn’t take long at all for her to cum. In fact, she came so hard that her pussy exploded all over my hand and legs. Juices poured out of her with force as she squirted over and over again. It was warm and slick. Her entire body shook violently. She grabbed onto me with her hands and just screamed through her orgasms. She had one right after another while I held her up. I wanted to keep her going but she soon grew too heavy for me to support. I held her tight and never let go of her neck until I slowed my hammering and eventually stopped. I took my hand away from her neck and hugged her from behind. She still quaked and shook in my arms but she was satisfied. All of her weight was on me as I just let her rest.

She needed a rest

She eventually regained enough of her consciousness to stand on her own and turn around to kiss me. Then she looked down at the mess she made on the floor and laughed. She told me that she hadn’t actually squirted in well over a decade. That just made me swell with pride. She shook her legs to get the last of it off of her and reached for a towel. She mopped it all up and threw it into the hamper. Then she opened the door and led me to her bedroom. It was clear from her face that she was exhausted but she was smiling wide. She sat down on the bed and pulled me down next to her. Then she simply kicked off her shoes and rolled over to lay on her side. She lifted her hand and waited for me to take it. I did as she wanted and laid down behind her and just spooned her. She wanted to be held while she rested and I more than okay with that. The only problem was that the Viagra had just kicked in and my cock was throbbing below my waist.

More next time

I still remember what happened next very clearly. I’ll let you know what it was next time. This story and this woman both deserve all of the time that I can possibly give them. It was a very special time and I was with a very special woman. There was still a whole lot more to play out and I was very happy to do it all. I like it when I have a mission like this and I always make sure that I get it done. Whether or not that happened is something that I’ll have to tell you when I get another chance to talk about her and everything we did together.