Hookup Stories

Seducing an Older Woman – Part 11

So, there I was. I was lying next to a gorgeous, older woman in bed with a throbbing erection. It was quite the journey to get to this place. She was my mother’s best friend and I had always found her painfully attractive. In fact, I spent plenty of nights, before I turned 18, energetically jerking off to her. She would come over to visit my mother and I wouldn’t be able to look away from her. Everything was perfect. From her legs to her ass to her tits, and even onto her pretty face and long, sexy hairy, she was absolutely perfect. I would usually spend so much time staring at her on those days that I would have no option but to head up to my room, pull out my dick, and jerk it as hard and fast as I could manage until I shot a load into any tissue, sock, or pair of dirt underwear that I had close to me. The one thing I never even thought to consider was whether or not she knew what I was doing or standing outside my door and listening to me pant and grunt at the thought of fucking her.

She always knew

It turned out that she always knew what I was doing. She knew that I was staring at her and she knew that I was jerking off to her. The best part of it was that she liked it. It turned her on to have this horny teen blowing his loads to her. It turned her on to know just how hard I actually jerking my teen dick to her. In fact, sometimes she would actually follow me up to my room. She would stand outside my door and just listen to all of the horny teen noises I was making while I pulled it to her. It got her wet and she just stood there until I was finished. Sometimes she’d simply go back to visiting my mother and other times she make her way back home to assault her own crotch in my name. it wasn’t until I turned 18 that I learned all of this. She had no problem with telling me that she was just as desperate to fuck me as I was to fuck her and she was going to make sure that she made it happen.

We were on vacation

My family and hers all took a vacation together and that’s where all of this came to light. It was me and my parents with her, her children, and her husband. We were going to be together for a week and I didn’t have a whole lot to do. Her kids were younger than me so I was pretty much on my own. At least, that was until I found that I’d be spending most of my time with her. It was the very first night when I found myself alone with her in the living room of the house we were renting. She let it all spill out of her. She was deeply unsatisfied when it came to her sexual needs. She was everything from a cum fetishist to a sexual slave and her husband refused to take care of her needs. Although he used to be happy to give her what she needed, it all ended when she had his kids. Now he couldn’t help but treat her like the mother of his children and nothing else. It was what led her to fantasize about me and my young, sexual energy. She knew that I would be able to treat her like the piece of fuck meat that she needed to be and I was more than happy to do it for her.

I fucked her a lot

I got to fuck her for the first time that very first night. It was in that same living room and it was after watching her fuck herself with a magic wand in her bedroom. It was also after I let her watch me jerk off to her in the bathroom. She came into the living room drunk after everyone else when to bed and sucked me off. Then she begged me to fuck her up her asshole. I tried as best I could but she was just too tight and I was just too excited. I had to stop trying to force myself into her ass and shove my cock into her soaking pussy to shoot my load inside her. It was the next day that she was intent of getting me inside her asshole. She spent the entire day wearing a bust plug to loosen herself up. I was more than happy to try again and I was going to give her what she needed this time.

She pretended she was sick

She had treated me to a blowjob earlier in the day, so I wasn’t going to be as excited as I was that first time. I wasn’t expecting her sneak back into the house while everyone else went to start a fire, though. She told them she was sick but it was a lie to be alone with me in the house. She snuck into the bathroom with me and I just couldn’t help but finger fuck her while everyone else was still milling around inside. I just edged her until they all decided to leave and then made her cum in my arms so hard that she actually squirted all over the bathroom floor. She really need to rest after that, so she led me to her room so I could lie next to her while she took a quick nap. That would have been fine, but there was a problem. I had also just taken four Viagra pills right before she showed up. I was lying behind her and my cock was throbbing in between my thighs. There was no way thatI was going to be able to wait for her.

I ran through my options

I really had to figure out what I could manage. I thought about just turning onto my back and jerking off next to her. There were a few problems with that, though. The first was that I had nowhere to drop my load. The second was that she could wake up in the middle of my jerk and I’d come off as some pathetic young kid who couldn’t control himself. If I was going to do something then I had to be more creative about it. I could always wake her up, but then I ran the risk of wearing out all of her sexual need before I got another shot at her ass. If I just tipped her over, ripped her legs open, and jammed my cock into her pussy until I filled her with my goo then she might be too exhausted to give up her ass later on. I couldn’t involve her that much, but I still had to involve her in some way. I reached down to grab onto my cock and that’s when I felt the solution to my problem. Her thighs were still soaking wet with her juices and squirt from a few minutes before. On top of that, she was wearing a tiny skirt with no panties and the skirt was already riding way up her back. Her ass and legs were pressed against me and totally wet and naked.

I went quickly

I made my decision and just went for it. She was sleeping and I had needs. I unbuttoned my pants and threw them onto the floor. Then I just got up behind her as close as I could and tried to line myself up. I grabbed onto my cock and actually felt my veins pulsing from how hard the whole thing was throbbing. She was slick and sloppy down there. That somehow turned me on ever more. She was a slim girl and I had always loves looking at her though gap. That was my target. I slid my cock into it and her body accepted me immediately. I felt her perfect pussy lips pressing against the top of my cock. Her skin was smooth as silk and I just started humping her crotch from behind. I press down on her top thigh as gently as I could for just a little more pressure and that was all I needed. A few silent pumps and my cock exploded in between her legs. The cum just coming and coming. There was so much that I could actually smell it and it felt amazing. Fucking a sleeping woman was somehow even naughtier than fucking a married woman and I left my cock between her thighs long after I stopped cumming and just let myself drift off to sleep.

More next time

I’ll have plenty more to tell you next time. She may have been sleeping, but this was still just one of the first times that I got to fuck this woman and I want to talk about all of them.