Hookup Stories

Seducing an Older Woman

I used to have a huge thing for older women. This was back when I was about 18 or so. There was just something about the experience they had that made me crazy. I wanted to get as much of it for myself as I possibly could. I tried to seduce many older women back there with varying degrees of success. I thought I’d share the story of how I managed to seduce my mother’s best friend. I was definitely 18 and she was in her late 30s, I believe. It worked better than I ever could have imagined and I still think of it with a giant smile on my face.

We went on vacation

It all started when we all went on a vacation. It was me and my family along her and her family. We were going to be in close quarters and I knew that it was going to be next to impossible to not be constantly hard as a rock around her. I had always had a thing for her. She was a tall brunette with perfect boobs and an amazing ass. Any time I had friends staying over, they all took turns just staring at her. That’s how hot this woman was and I had to do something about it. Sure, she was married and had kids, but still. I was 18 and I needed her. I knew that I had to figure out how exactly I could get something from her. At the very least, I wanted to see her naked. That was pretty much my goal for the vacation. I didn’t care if I had to walk in on her in the shower or catch her changing in her bedroom. I had to see her naked, no matter what it took.

My first chance came quickly

I never thought I’d get to see her naked pretty much as soon as the whole thing started. We had all arrived at the vacation cottage that morning and everyone unpacked. I took every opportunity that I passed by her in the hall to check her out. She was looking tired, but hotter than ever. She has this tiny skirt on and a tank top and really showed off her perfect tits. Anyway, we all got together and both families were settled and decided to head down to the lake for a quick swim before dinner. Both families headed out but it wasn’t long before she said she was heading back to the house for a few minutes. No one thought anything about it and twenty minutes passed. I was having too much fun in the water to really notice anything, but I suddenly had to use the bathroom worse than ever before. I ran out of water and up to the house without saying anything to anyone. I made it to the bathroom just in time and did my business. I make my way out of the bathroom and that’s when I heard it.

She was gone for a very good reason

The sound was pretty quiet, but I still heard it. I had to follow what sounded like low vibrations in one of the rooms and the closer I got to her room, the louder it got. That was when I saw that the bedroom door was open just a crack and the sound was clearly coming from inside. I pushed the door open and that’s when I was greeted to a site of this gorgeous MILF naked and on her back with her legs spread wide. She was going at her pussy with a giant vibrator. Now that the door was open, I could tell that it was a loud and powerful thing that was clearly doing the job for her. I could immediately see why she needed to be completely alone to use it. I must have made a noise because her eyes shot open right as it was clear that she was starting to cum. She looked shocked at first, but seemed to realize it was me, rather than her husband or one of her kids. I really mean that she was right on the edge and she just looked me in the eyes and started cumming right there on the bed.

I was frozen

I had no idea what to do. I had no expectations of this happening and I certainly wasn’t hating it. I just stood there at the door for a few minutes and watched her try to catch her breath with her eyes closed. It was clearly a very nice orgasm. Then she finally opened up her eyes and looked at me.

“It’s okay that you watched me, but let’s not tell anyone about this, okay?”

I just stammered a yes and started to back out of the room.

“By the way, you owe me a show later. Just because I like to be watched doesn’t mean that I perform for free, honey.”

She was smiling wide and turned around to face away from me and recover. I just closed the door and ran right back to the bathroom. I can’t tell you just how hard I started jerking off right then and there. I was on the toilet with a massive erection and I was working it harder than I had every jerked it before. I was even running the water to lather up the soap for lube while I played back the images of her cumming over and over again.

I must have been loud

Either she instinctively knew what I must have been doing or the sloppy sound of the soap and stroking gave me away. Either way, I was rounding the corner when the bathroom door slowly opened. I panicked and immediately stopped, but then I saw that it was her. She was still completely naked and smiling at me. She slowly slipped into the bathroom and closed the door behind her.

“I guess you’re ready, then.” She said.

The rush of excitement and arousal slammed through my entire body. Once again, I had no idea what to do. I think that I must have just nodded to her and grabbed right back onto my dick. I had never been watched before in my entire life and I still don’t know if I actually like it. I still had to do it, though. I watched her and now she got to watch me. That was just fair. I started stroking all over again and looked up into her eyes while I worked. That part really turned me on, but I also felt totally open and embarrassed at the same time.

She knew I was close

She didn’t really waste any time in making sure that she enjoyed this as much as she possibly could. She could probably tell that I was getting close by the way that I was jerking off faster and faster.

“That’s a good boy, keep going.” She said with a smile. Then I felt something brush against my calf. I looked down to see her naked foot making its way up my leg, touching my skin the entire way.

“Don’t worry about that. Look me in the eye, honey.”

I did as she asked and looked right at her and I felt my cock start to explode. The cum just shot out all over the place and I noticed her look down to her foot right before I felt her toes start sliding up and down my shaft. I let my dick go and leaned back while she stroked me through the orgasm and kept going until I felt every last drop of my cum leave me. I fought to keep my eyes open so I could keep looking at her and she never stopped smiling.

“Looks like we made a mess.”

I looked down to see her foot absolutely covered in cum. I guess it wasn’t just shooting all over the place like I though. She knew exactly what she was doing. She caught it all right on her foot and made sure she didn’t miss a drop. The she simply grabbed some toilet paper from the roll next to me, leaned forward, and wiped it all off of her. She slipped the tissue in between my thighs to drop it in the toilet, kissed her first two fingers, then pressed them to my rapidly deflating cock.

She said “Good job.” Then she just turned around and walked out of the bathroom, closing the door behind her.

More next time

This was just the beginning of the vacation and I had no idea that any of this was going to happen. I couldn’t have even come up with it in my biggest fantasies. It happened, though, and that wasn’t the end of it. I’ll some more to say about it next time. It was a great vacation and I found out that this much older woman wanted me just as much as I wanted her.