I wish that I could say that the first night with this incredible older woman ended exactly the way that I wanted it to. The simple fact is that hook ups don’t always go the way they’re supposed to. It’s not that I have much to complain about, though. I mean, after all, in one day, the both of us had already cum twice. Her first time was when I walked in on her masturbating in her bedroom. She had a giant magic wand on her clit and just smiled at me while she came. My first time was just a few minutes later in the bathroom. I just had to jerk off after seeing that and she even came into watch me. That was on the morning of the first day of vacation and things never slowed down after that. She blew me on the living room sofa after everyone went to bed and I ate her out. We were both tired from all of the orgasms, but there was still one thing left for us to do. It makes total sense if you remember what kind of woman this was that I’m talking about.
She was my mom’s bestie
The older woman I’m talking about was my mother’s best friend and both of our families were on vacation. I had fantasized about her since my first boner and it turned out that was fantasizing about me as well. She laid it all out for me in the living room when she bared her soul to me. After having kids with her husband, he stopped looking at her as a sexual conquest and now she was just the mother of his children. This meant that he wasn’t willing to do the kind of things that she really liked. She got off on being used for a man’s pleasure and it just wasn’t happening for her. That’s why she started to fantasize about me. She knew that I was jerking off to her every single time I saw her. In fact, sometimes she would even listen to me cumming for her on the other side of my bedroom door. She saw me as the person who could give her the sexual passion that she needed. She knew that I fantasized about doing every filthy thing imaginable to her because I was only 18 and wanted to do it all. That was why she planned this whole vacation. She saw it as a way for us to be alone with each other. She planned me walking in on her and she planned on me using her as a fuck toy. I was more than happy to oblige her. That was why she was lying on the sofa with her head in my lap and a butt plug in her asshole. She wanted me to fuck her up the ass and make her feel like a tiny little woman that any man could use for his own selfish pleasure because she was just that desirable.
Things didn’t go as planned
It was knowing all of this that led me to tell her to get back on her knees after we both had some time to rest on the sofa. Simply having her head on my lap and her naked body next to me was more than enough to get me hard again and I wanted to be inside her. I stood behind her and gently pulled out the big, glass butt plug. I watched her tight, neglected asshole close right back up in front of my eyes. I knew it was going to be difficult to get myself in there, but I was still going to try. I lubed it back up and pressed my dick against it. Nothing happened. She pushed her entire body back into me to get me inside her. Once again, nothing happened. I tried and tried, but nothing would let me penetrate her ass. Getting the hard, glass plug into her was one thing, but this was a penis. It’s difficult to begin with, but after you’ve already cum twice in one day, trying for anal sex is next to impossible. The bigger problem was that trying to force my way in had me on the verge of cumming all over again.
She just wanted me
I told her that I was getting close and that I couldn’t get in. She seemed a little disappointed, but I know that she understood just6 how tight she happened to be.
“That’s okay, honey, just come in my pussy for me, please!” She said in between moans.
I certainly wasn’t going to let her down any more than I already had, so I pulled my dick back and slammed it into her pussy. It’s still one of the best feeling pussies that I’ve ever had the pleasure of fucking. It was soaking wet and felt like silk inside. It was also almost as tight as her asshole. The pleasure that I was getting from her hole made me explode inside her almost immediately. I think that the sensation of a younger man with a pure sexual hunger cumming inside her was enough to make her cum again as well. I felt her body shake and stutter while I emptied what little bit of cum I had left into her. Then I just collapsed onto the sofa and watched as it slowly leaked out of her and trickled down over her clit and down her perfect thighs.
More next time
There’s still a whole lot of this story to tell and I’ll get back to it. I’m not going to tell you here if I ever fucked her up her ass, but we had quite a lot of time together. We spent the rest of that first night cuddling on the sofa and sleeping on and off. We only got up after the sun rose to sneak back into our room so no one would know what happened in the living room that night.