Hookup Stories

Seducing and Older Woman – Part 4

I was lying there with her on my chest when she propped herself up on one arm, told me she’d be back in a second, kissed me on the forehead, and got up to walk up the stairs to the second floor. That gave me a few minutes to just relax and think about everything that had just happened. First of all, I was happy that she kissed me on the forehead and not tried to kiss me on the lips. She had just given me a very satisfying blowjob and swallowed every last drop of cum that I had in me. Kissing on the lips after that is incredibly unappealing. Then I was just happy that I had walked in on her so many hours before. She was my mother’s best friend and much older than me. We were all on vacation and things had taken a turn that I never would have been able to fantasize about, no matter how creative I tried to be. This was a woman that I had always wanted to be with and she was giving me every opportunity that she could while we were together with each other.

It started innocently

The whole thing had started very innocently. Like I said, our families were on vacation together and things came to a head when everyone but her was down at the lake. I had to run back to the house to use the bathroom when I heard something coming from the room that she was sharing with her husband. I knew that she was in the house alone and I had no idea what that sound could have been. I followed it down the hallway and opened her bedroom door to see the source of it. It was a giant magic wand vibrator that she was using on her clit. She was all alone and naked and seemingly enjoying all of the things that the vibrator was doing for her. She looked at me when I opened the door and just came right there while she smile at me. I just stood there and enjoyed the view of this woman that I had fantasized about since adolescence cumming in front of me. After she was all done, I had to run back to the bathroom to pull out my dick and jerk it off as hard as I could possibly manage.

She came for me

I was mid-stroke when the bathroom door opened and she walked in on me. She believed she had just given me a show, so now it was my turn to give her one. She stood there and watched me jerk off to her and it was the most intimate thing I had ever done in my life. She watched me cum, just like I watched her cum and we were now both even. She simply walked right back out after I finished and that was that. It wasn’t until much later that night that I saw her alone again. Everyone else headed off to bed after a night of drinking but she stayed behind with me in the living room. We were both sitting on the sofa when she decided to confide in me. It turned out that I wasn’t the only person fantasizing about the other. She told me that she thought about me every single time she had sex with her husband. It was because she wasn’t getting what she needed out of him. She was a sexual being who needed deep sexual pleasure to survive. He was simply treating her like the virginal mother of his children and not doing the things that made her feel like a woman. That’s why she would always fantasize about me. She knew that I would have to run up to my room to jerk off every time she came over the house. She knew that I wanted to do things to her that would leave her humiliated and exhausted at the end. Those were the things that she needed in her life and this was the time that she had chosen to finally get them. I was finally of legal age and she was going to let herself get used by me right behind everyone else’s backs.

She brushed her teeth

She came back down from upstairs and I could immediately smell the mint of toothpaste. She had brushed her teeth and gotten rid of any residual cum that she had in her mouth. I was grateful for that and attacked her as soon as she sat back down on the sofa. I shot my tongue into her perfect mouth and explored every last inch of it. I wanted to taste her and feel her in any way that I could. I didn’t want to leave any part of her as a mystery. She replied by running her tongue over my teeth and massaged my tongue. We kissed for a while until she pushed me back and smiled up at me. She had things that she needed to do and I hadn’t even noticed the velvet bag that she had brought down with her. She opened it up and dropped the contents onto the sofa. It was actually the first time that I had ever seen a butt plug in real life. I knew what they were, but had never found a girl to use one on.

It was there for a reason

She just looked up at me and brought the butt plug up in front of her face. It was made of glass and fairly large. I have no idea what one would feel like, but it seemed that this one was meant to be painful and that was probably the reason that she liked it so much.

“It’s been a really, really long time since I’ve had anyone in my ass.” She said quietly. “I’m like a virgin back there and it’s all closed up. I want to make sure that you can get inside me, so I got this. Do you want to put it in?”

That was when I also noticed the bottle of lube that had fallen out with the plug. I was more than happy to put it in for her, but it brought up one very big question. If she brought the butt plug with her on vacation, does that mean she had planned this whole thing out? She clearly wasn’t expecting to need it with her husband, since he was unwilling to fuck her the way that she needed. If she brought it, that meant she brought it for me.

I put it in for her

I nodded and took the butt plug from her. It was kind of cold and as smooth as glass could be. She responded by standing and turning away from me, only to get on her knees on the sofa with her amazing ass right in my face. Everything looked perfect back there. The way her pussy showed from between her thigh made my mouth water. Her pussy looked like it had been sculpted by the gods themselves. The lips weren’t too long, but they were there to suck on. Her asshole was tiny and tight. It was a slightly darker color than the rest of her. I open up the bottle of lube and let it cascade down her ass crack. She leaned forward a little bit to let it pool around her hole. I just reached in and gently massaged it around her asshole. I even slipped in my first two fingers to lubricate her from the inside. I wanted to make sure that it was as pleasurable as it could possibly be for her. Then I lubricated the plug itself and started to gently push it inside her. It was very difficult at first and I didn’t want to rush things. Her hole was incredibly tight, but I already knew that after my slid my fingers inside. She moaned gently with every push from me. When I finally got it to open up just enough to start accepting it, I grabbed onto hip and pushed hard. Her moan grew in volume and she pressed back with her entire body. The largest circumference of the plug finally made it passed her anal entrance and then her asshole just pulled the rest of it inside with me having to push at all. I was so wrapped up with what I was doing that I didn’t even notice that she was panting and sweating in front of me. It had been so long since someone penetrated her anus that she had to give it her all to accept it, but she did.

More next time

That was the first time I had ever inserted anything into someone anus and it’s a treasured memory. I’ll have more of the story next time. I couldn’t believe what I heard when I asked her why she brought the plug with her.