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Hookup Stories

Seducing an Older Woman – Part 9

I told you before about the time I hooked up with a much older woman. It wasn’t just that she was older, though. What was really fun about it was the fact that it was my mother’s best friend. This was a woman that I was attracted to for many years. She would come over all the time and I wouldn’t be able to stop staring at her. In fact, a lot of times she was there, I had to run up to my room to jerk off as hard and fast as I possibly could. She just turned me on that much. What I didn’t know at the time was that this woman was just as attracted to me. She confided that she always knew what I was doing when I went to my room. In fact, sometimes she would follow me up and listen to me stroke myself through my door. The thought of an 18 year old guy cumming to her turned her on so much that she would usually end up doing the same thing as soon as she got home. Things could have gone on forever like this, with the two of us masturbating to each other over and over again, but she decided that she wanted something more.

We went on vacation

Things all came to a head when we all went on vacation together. It was me and my parents along with her, her husband, and her kids. They were younger than me, so I didn’t really have anyone to hang out. That’s probably why I decided to make it my job to at least see this woman naked while we were all staying together. It was a lofty goal, but I was sure that I could make it happen. I just didn’t expect it to happen so quickly. Most of us were down by the lake on the very first day, but she stayed behind. I had to take a bathroom break, so I made my way back to the cottage. I was just finished pissing when I heard a strange noise coming from down the hall. I had no idea what it was, so I followed it. TO my surprise, it let me right to her room. I slowly opened the door and was greeted by the site of her totally naked and energetically masturbating with a magic wand.

She let me watch

I was shocked at what I saw and horrified when she heard me. I thought I was going to have to apologize to her and that I had just ruined everything by violating her privacy. Fortunately, things didn’t work out that way. She saw me standing there and just took a second to realize who I was. Once she knew that it was me and not someone else, she just locked eyes with me and let herself cum. She made a lot of noise and looked right at me with a smile on her face for her whole orgasm. I just stood there and watched it, loving every single second of it. When she finally stopped cumming she turned off the wand and put it down. She simply and softly told me that I now owed her a show of my own and turned over to relax. That was my cue to leave. I quietly closed the door and made my way back down to the bathroom. There was no way that I was going to be able to watch all of that and not have to immediately jerk off to it.

She followed me

I was just sitting down on the toilet with my shorts around my ankles and my dick soaped up and in my hand when the bathroom door opened. It was her and it turned out that she was already there to get her show from me. She closed the door behind her and just stood there to watch me work. I was embarrassed and extremely self-conscious, but I still did it. I really figured that I owed it to her and it seemed like something that she really wanted to see. I just sat there and did everything that I would normally do in this situation. The only difference was that I was looking up into her eyes the whole time. I don’t know if it was something she wanted to do or if it was just to make sure the floor stayed clean, but she paid attention  to when I was about to explode and caught all of my cum as it shot out with her bare foot. She took it all and didn’t lose a single drop. Once I was finished she just cleaned it all off with toilet paper, dropped it into the toilet between my legs, and left. That was the first time I ever jerked off in front of someone.

She laid it all out for me

It wasn’t until later that night that she told me everything that was going on in her head. It turned out that she had been lacking in the kind of sexual passion that she needed for a very long time. She was the kind of woman who liked it rough. She also liked it when men used her and degraded her. She loved the humiliation but had to live without it ever since she gave birth. After that big change, her husband stopped looking at her like a sex object. He started looking at her like the mother of his children and was unable to treat her the way that she wanted to be treated. That’s what led her to me. She knew that I wanted her. She also knew that an 18 year old would be more than willing to treat her like a piece of meat. She came up with the entire idea of taking a vacation just so she could get what she wanted out of me. She told me all of this on that very first night and then begged me to fuck her up the ass. That was, unfortunately, something I was unable to do that first night.

She was too tight

After years of never having her anus penetrated, it had closed back up nice and tight. I tried to fuck it, but I couldn’t get inside. All of the pressure of trying was too much and I couldn’t stop myself from cumming. She asked me to just shoot it into her pussy and that was the end of our first night together. The next day brought a whole new opportunity. She really wanted to get what she needed and she put in the effort to make it happen. She spent the entire next day with a butt plug in her asshole. She even flashed it to me so I could see it. That wasn’t all, though. She was playing tennis with the other adults when I just couldn’t take it anymore. I called her over behind the public restrooms and pushed her down onto her knees. I knew that it would be something she liked and she responded in kind. She gave me a blowjob right there, just a few feet away from my parents and her husband. She even jerked me off onto her tits and buttoned up her shirt to keep it there all day long.

I was intent on giving it to her

I was pretty much falling in love with this woman at this point. She needed a man to take her and I was going to make sure that it was me who did it. I didn’t care about her husband or what would happen if anyone found out. He wasn’t giving her what she needed and I was going to step in and do it. I was leaning against the wall of the public restroom after she made her way back to the court and thinking about just how I was going to make that happen. I kept running the scenarios through my head until I came to one that might just work. It seemed really simple and wouldn’t take much at all. I waited for some time to pass so no one would get suspicious, then I made my way back to the cottage. It was going to be a lot easier if I could do what needed to be done with no one around.

More next time

I’ll let you know what happened next time. This is still a story that I love to tell. It brings up a whole lot of points that I care a lot about. You should always be aware of what the women you’re with needs. If she goes out of her way to make you happy then you have to do the same exact thing. It doesn’t matter if she’s the mother of your children or a random girl you’re hooking up with. Give her your very best and she’ll do the same for you. It’s really that simple and it’s something that we should all be doing for each other, even when it has nothing to do with sex.

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Hookup Tips

How to Hook up in the Shower

If there’s one place that seems great to have sex in, it’s the shower. Lots of movie sex scenes take place in them and they just seem ideal. You have the hot water running down your body. The steam makes it all warm and nice, plus you’re completely naked and touching yourself. If you can manage to walk in on a horny hook up when she’s taking a shower then you’re guaranteed to get laid in one. The problem is that it’s not as easy as it sounds. There are a lot of different things working against you when it comes to shower sex.

The steam is a problem

The first issue is the steam itself. If you’re banging away on someone then you’re going to have to be breathing heavy. When you breathe heavy in a room that’s filled with steam, you’re going to immediately get lightheaded. Get lightheaded enough and you might just pass out and crack your skull open. If you want to stand the best chance then you want to keep the shower curtain open. If you can keep the bathroom door open, too then it’s even better. You’ll have the cool air to keep you straight.

Don’t use the showerhead

There are few things that are more fun that using a showerhead to make a girl cum. There’s a reason that they always take so long in the bath. The showerhead is the perfect instrument for working their clits and making them cum harder than anything else ever could. There’s a problem with them, though. All of that water is going to dry out her pussy faster than that time her dad accidentally sent her a dick pic. If you want to have sex then you have to give up on your idea of fucking her with water. Save that for a day when you’re not going to try and get inside her.

Bend her over

The shower is a tight place and it can be tough to get into a good position. Most people just try for standing sex. If you can get her legs around you then you have free access to her pussy. It’s extremely dangerous, though. One wrong move and you’re going to slip and you’re both going to fall. There are just too many things that can sever your spinal cord on the way down in a shower. Play it safe by bending her over and fucking her from behind. If you really want a night to remember, lube up her asshole with soap and pound her backdoor open before she even realizes what you’re doing.

Cum in her face

The best thing that the shower really has to offer you is the chance to do the dirty stuff in a place where you can get clean right away. If your hook up has a problem with you shooting your load all over her face then this is the best place for you do it. You can even let her kneel under the water so it washes away as soon as it hits her. It’s a great way to ease her into the idea of facials. When she realizes that they’re not really a big deal, you can give them outside of the shower whenever you want.

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Hookup Tips

How to Make Sure she Cums

If you really want to walk away from a hook up with a smile on your face then you have to make the girl cum. It strokes your ego and lets you know that you gave a show that she was able to really enjoy. The problem is that it’s not always that easy. It’s next to impossible to just give a stranger an orgasm. You never know what they like and you certainly never know how hard they like it. That’s why you have to go about it in a total different way when you don’t know her.

Talk about kink

The first thing you should try doing is simply talking about kink before you have sex. This is going to give you a great idea of what she’s into. It doesn’t need to be an in depth conversation. Just bring up something that you’ve seen and see what her reaction happens to be. If you find out that you’re with a kinky girl then her orgasm is going to require you to go hard and give her plenty of additional action. That means you should consider spanking her or just going full kink.

Let her touch herself

If you don’t want to talk about kink with a stranger then your best bet is going to be simply letting her fuck herself. She may be reluctant, but if you tell her that it turns you on she might be willing to do it. When she starts, make sure you watch everything that she’s doing. Pay attentions to the way she does it and how hard or fast she goes. That’s what you’re going to have to do to her if you want to make her cum. If you can manage it, you’ll have a fuck friend that you can call up whenever you want to share an orgasm.

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Hookup Stories

Hooking Up with the Last girl – Part 7

I had everything I needed to finally get the job done. Her roommate had me wanting to fuck and the hard on she gave me from stiffer than anything I had all night. I got up and walked right into the drunk girl’s room. I made sure to the leave the door open so the roommate could watch. That was helping me out a lot. I’d be able to look at her while I worked and I knew that was what was going to make the difference. The drunk girl finally stopped playing with herself when she saw me and immediately smiled. I didn’t stop. I grabbed onto her meaty hips and flipped her right around. I shoved my hand around and onto her pelvis to guide her up. She followed me lead and got up onto her knees on the bed. I knew what I was going to do and I knew that it was what she needed. She let her head fall down onto the backs of her arms and just waited to take what I had to give her. I looked out through the door and locked eyes with her roommate.

I hit the last mile

Just like every other inch of her, her asshoie was lubed up and soaking wet. It didn’t take any force at all to get my cock inside it. It just slipped right in until her body just pulled me in the rest of the way. I smiled at her roommate as the drunk girl started to moan. I saw the roommate nod to me and smile. I started sliding my rock hard cock in and out of her asshole. I started nice and slow at first and imagined that it was the roommate I was fucking. She was clearly enjoying the whole thing and I watched as she brought both of her feet up onto the sofa and let her legs spread apart. It was only at that moment that I noticed what she was wearing. She had long t-shirt and panties on and nothing else. I really wish I had paid attention to that when I was with her just a few minutes ago. I just couldn’t take my eyes away from her, no matter how much noise the drunk girl was making in front of me. I even managed to reach out and grab onto her hair without looking at her a single time.

She played along

I pulled her hair back hard and started pounding my cock into her faster and faster. She started up with the Daddy shit again and I just let her scream and moan. I was paying more attention to the roommate. She sat there watching and slowly slipped her right hand into her panties. Seeing her do that sent a shock of pleasure through my entire body. I really started to jackhammer this girl’s asshole when I saw that. There was something so intimate and sexy about it that I couldn’t stop looking. I was using the drunk girl as a proxy for the roommate and she seemed to like it just as much as I did. That’s why I decided to reach around and rub her swollen clit while I fucked her asshole. It was like I was working the other girl’s clit instead of her working it herself. I started slow and saw that she was going at the same pace. Then I worked her clit faster and faster and watched as the roommate did the same exact thing with her hand. I watched as her chest started to heave and then I knew that it was time.

I turned it to eleven

I worked the clit as fast as I could and really jackhammered her ass with my cock. I stared deep into her roommate’s eyes as she played along. I could vaguely hear the screaming and the word Daddy over and over again. I could tell that her roommate was getting close. She was only able to keep her eyes halfway open and I couldn’t hole myself back, either. I wasn’t paying any attention to the drunk girl at all, but I was extremely lucky to find out that she was just as close as the two of us. I let out a load grunt and shot my hot load deep into the drunk girl’s asshole. I felt her squirt splatter against my thighs as soon as I grunted. I stood there and let the cum shoot out in spurts inside her while I watched her roommates entire body shake and buck in a deep and satisfying orgasm. All three of use came together and the drunk girl had no idea that anyone else was involved. She collapsed onto her stomach and I hunched over to catch my breath and just kept smiling at the roommate as she smiled at me and caught her own breath.

I needed a break

I was so exhausted at this point that I couldn’t help but sit on the edge of the drunk girl’s bed. I could have probably left, but I wanted to make sure that she was fully asleep before I did that. I was sweaty and tired and just couldn’t stand anymore. I let my head fall back and I just laid there with her next to me. I must have fallen asleep because I don’t remember anything else until I was woken up by someone on top of me. I was a little groggy and out of it, so I looked around and tried to figure out what was going on. I could see that the drunk girl was completely passed out and snoring on the bed next to me. Her large ass was red and she seemed happy. I looked above me and saw her. That thing that was on top of he was her roommate and was riding my cock. She leaned in close and whispered, “Sorry, babe, I just couldn’t resist anymore.”

I let her work

I didn’t have a single problem with this in the world. She must has sat on the sofa and expected me to come out to her, but I fell asleep. That meant she must have come in after me and just saddled up next to the drunk girl. I have no idea how she managed to get me hard, but I was stiff and deep inside her pussy. It was tight and lovely and everything that I had hoped it would be. It felt smooth but still gripped my cock and made me want to get as deep inside her as I could. I grabbed onto her slender hips and shoved myself into her. She moaned and let her head fall back. I did it again and she had to cover her mouth so she wouldn’t make too much noise. She was naked and her body was perfect. Her tits were the best that I had ever seen and they bounced right about me. I felt her skin start to glisten under my fingers. I thrusted again and she whimpered a quiet “Oh, fuck!” under her breath. She dug her nails into my chest and started to cum right on top of me.

I let her have it

I didn’t have any fight left in me. I was exhausted, practically in love with this girls, and my cock was about to explode yet again. I didn’t even bother trying to stop it. I jammed my cock into her again so hard that I hit her cervix and just let it blow. My cum shot out in streams inside her. She moaned and writhed on top of me. Her fingers clenched and unclenched on my chest. I kept pumping as the cum kept shooting into her. It didn’t matter that I had already blown two loads that night. This girl just brought it out of me. I have no idea how it took me to stop cumming, but it finally stopped and she collapsed on top of me, heaving and sweating. I just laid there next to the passed out drunk girl and ran my fingers over her roommates back. She let out a satisfied coo and we enjoy each other for a while. My dick was still inside her as it deflated and left the last few drops of cum inside her.

I finally snuck out

After a good, long while, she lifted her body up and kissed me on my lips. Then she leaned in to whisper “Now’s probably your best chance, babe.” She kissed me again and I knew she was right. I had to escape the drunk girl, but I still didn’t want to leave the roommate. That was when I heard the best sentence of my entire life. “Don’t worry, I already put my number into your phone.”

With that she quietly got off me, handed me my pants, and walked to the apartment door. She kissed me again and wished me a good night as I walked out and finally made my way home after a long evening.

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Hookup Stories

Hooking Up with the Last girl – Part 6

I stood in the bathroom for a few minutes to collect myself. The fatigue was really starting to kick in at this point. I had wanted to go to bed a long, long time ago. Now, here I was. I was in a drink girl’s apartment and I didn’t even know her name. On top that, I didn’t even find her all that attractive. I had been tasked with getting her home and that’s what I did. I thought I was going to be able to get rid of her before she got me into her room. I should have left, but I saw how desperate for sex she really was and I just couldn’t. I felt bad for her and I just had to take care of her. I had managed to make her cum twice so far, but I knew that she needed more. My main goal was to make her cum so much that she just passed out so I could leave. Then I could safely assume that she’d forget who I was and I’d never have to deal with the drunk girl who soaked my car with her pussy squirt ever again.

I can cum three times

The only reason that I knew I could do this was my ability to cum three times in a single night with someone. It’s just the way that I am and I figured I’d need all three to give her what she needed. I had just blown one load in her pussy and now I was waiting for my hard on to come back. It usually took about ten minutes, but that was when I was with women that I wanted to fuck. I really had no desire to fuck this one, so I was in a little bit of trouble. A trip to the bathroom is usually enough time to get me back in the game. Right now my dick, and the rest of me, just wanted to sleep. I wanted to stay in there for longer, but the more time I spent in the bathroom, the more likely it was that she’d wake up and want to take over with something passionate and gross. I just couldn’t handle the thought of it, so I opened the door and tried to figure out what I was going to do without a hard on. Luckily, that was when I met her.

She was gorgeous

I had never even considered the possibility of this girl having a roommate, but here she was. She was standing right in front of the bathroom and I almost walked right into her. She stood there and eyed me up and down for a second or two. That was when I remembered that I was completely naked from the waist down. I threw my hands over my cock and just apologized to her. “Shit, sorry! I’m sorry. I didn’t know anyone else was here. I didn’t mean to…”

She just smiled and shook her head. “It’s okay, baby, don’t worry about it. I wanted to come out and see who she finally got to fuck her and say thank you.”?

She laughed again and I was totally lost. I could feel the confusion spread across her face and it seemed to entertain her a lot. “I could hear her on the other side of the apartment. You must be pretty good to make her cum so fast. She usually takes a good hour to get herself off and this is much better for me. I might actually get a chance to sleep tonight.”

She marked my severe confusion yet again and just laughed at me. She reached out for my hand and I just took it. I had no idea what was going on at this point.

“It’s okay, you have a little while. She’s just enjoying herself in there right now.”

She led me to the sofa

I just walked with her and looked back at the drunk girl’s room to know exactly what she meant. Her door was wide open and her legs were still hanging off the edge of her bed. I could see her quietly playing with my cum as it leaked out of her pussy. She rubbed it all around her lips and used it to rub her clit, then went back to sliding her finger inside herself to feel even more. Her roommate sat down on the sofa in front of us and I sat down next to her. My dick was flaccid and I felt it flop against the cushion. I turned my body to face her and find out what exactly was going on right now. This girl was absolutely gorgeous and I couldn’t help but wish that I was in her bedroom instead of the other girl’s.

She laid it all out

“She’s a very horny girl in there. I’ve been living here for about two years and she’s always waking me up at night. There hasn’t been a single guy here with her in the entire time I’ve lived here, so I know that she’s desperate and that’s why I let it slide. She’s just so loud! I can hear that piston thing in there every single night and it drives me crazy. That’s why I was so surprised to hear an actual man walk out of her room tonight.”

Now it was all starting to make sense to me. She was just as tired of and sorry for this girl as I was. She couldn’t help but come out and see who was willing to finally fuck her. I told her everything that had happened that night. I even let her know about the mess she left in my car. She just acted like it was all the furthest thing from a surprise to her. She also made sure to thank me over and over again for biting the bullet on this one and I couldn’t help but want to see this girl again.

I was still in trouble

“So, you’re not, like, done yet, right? I mean, I know her. You might be really good, but she’s going to start that piston thing up again as soon as you leave. She’s been so desperate for so long that she can’t help it. I was really hoping that you could go a few more rounds with her.”

“I really don’t think I can, to be honest.” I said. I looked down at my dick to draw her eyes down to it. “I’m just not into her. I can’t get it up again. I really want to, but I don’t think it’s possible. I know that if I get her off one more time, she’ll just go to sleep and I can sneak out without her ever remember who I am. As it is now, I’ll probably end up having her show up at the bar in a few weeks to try and do this all over again and I really don’t want that to happen.”

That was the whole truth and I didn’t feel bad telling it to her. She was clearly in the same exact boat as I was with this girl.

She helped me out

“I’ll tell you what, babe…” She said, but she didn’t finish her sentence. She winked at me and slid off the sofa and onto her knees. She crawled her way over in between my thighs and spread them apart with her warm hands. Then she just leaned right in and ran her soft tongue up and down my shaft. She did one side and then the other. It felt fucking fantastic. It was like I was being born again. She was cleaning off the filth of the drink girl with her mouth and I just leaned back and enjoyed it. I made sure to keep my eyes wide open so I could watch her. She was absolutely beautiful and I wanted to fuck her so badly that my soul wept. She wrapped her lips around my cock and took it all the way into her perfect mouth. Seeing it in there was all I needed for it to explode into a solid erection. She could have stopped there, but she gave me the gift of a good minute of the best blowjob of my life. We both knew what she was doing, though, and it had to come to an end. She let my stiff cock fall out of her mouth with a string of saliva following it. Not even my dick wanted to let her go. Then she just looked up and winked at me.

“Now go get her, tiger. Do us both a favor and finish her off. I’ll sit here and watch if it’ll keep you hard.”

More next time

Now I was finally ready to finish it all up and I was going to do it. That roommate was a gift from the universe and I was never going to let it go to waste. I knew that she was in it with me and having her watch me fuck the drunk girl filled me with renewed energy.