Category: Hookup Stories

When I woke up the next day, I had a whole new outlook on my mother’s best friend. I suddenly knew what she was after and I really wanted to give it to her. That meant that I had to be in charge of everything that happened between us from them on. After I walked in on her masturbating in her room the day before, things had taken a very severe turn. This was a much older woman than me. She was my mother’s best friend and in her late 30s or early 40s. I was 18 at the time and I had always wanted to fuck this woman. I was deeply attracted to her and she was amazing in every way. Any time she came over to visit us, I’d take one look at her tight body and have to run to my bedroom to jerk off to her. I just had no idea that sometimes she followed me and listened to me pleasuring myself on the other side of my door. That was because she was just as attracted to me as I was to her. She told me all of this after she gave me a blowjob on the living room sofa.

We were on vacation

Both of our families were on vacation at a lakeside cottage. She was there with her husband and I was there with my parents. I knew that I wanted to take the opportunity to finally see her naked, but she took things to a whole new level. I ran into the cottage while everyone else was at the lake and walked in on her on the first day. She was naked in her room with her legs spread wide and magic wand vibrating her clit. She saw me walk into the room, but never even considered stopping and covering herself up. She just locked her eyes onto mine and came while I watched her. Just seeing it made my cock start throbbing so much that I had to run to the bathroom to jerk off. That could have been the end of it, but she had other plans. She just followed me right into the bathroom and made me give her the same show that she had given me. She watched me jerk off and made sure to catch my cum so it didn’t shoot all over the place and get us both in trouble.

She needed to feel sexy

It was later that night that I learned the information that I really needed. I was in the living room while she was out at a fire with everyone else. They came in to head to bed and she stayed back. She sat next to me on the sofa and told me how neglected she felt as a sexual being. Her husband simply saw her as the mother of his children and refused to do the things that she used to love. She was nothing more than a cock slut deep down and her husband used to love that about her. Now that she was a mother, she had to put those desires aside and that was what led her to fantasize about someone like me. She knew that I wanted to filthy things to her. She knew that I was jerking off to her on a nightly basis. She also knew that was the kind of sexual energy that she needed. She needed to feel like a sexual being that was deeply desired by men again. That was where I came in. She wanted me to use her for pleasure and nothing more. I did what I could the first night, but it wasn’t enough.

She was too tight

It turned out that having to give up her true passions for so long had reset her body. She loved nothing more than to be bent over by horny men and taken up her asshole and I can understand that. Having anal sex isn’t like vaginal sex. It’s primal and more passionate. Being fucked up the ass by a man means that she’s being used for pleasure and that’s what she loved. Having vaginal sex means that the man also wants to give her pleasure and that takes away that primal, sexual use. She had a butt plug in for a little while to loosen herself up, but it was just too tight. The years without any anal penetration had practically left her a virgin again. I tried to get myself in there, but it was just too much. All of the pushing and pressure sent me over the edge and I had to shove my dick into her sopping wet pussy to explode inside her. I know it wasn’t totally satisfying for her, but it was still close to what she was looking for.

She was ready again the next day

I woke up the next morning and headed downstairs to see everyone in the kitchen. She was wearing a tiny little tennis outfit that showed of every last one of her amazing curves. If you don’t know what a tennis outfit is, it’s pretty much standard issue for MILFs. It’s a short, pleated skirt with a button down shirt. She was wearing a visor on her head and her should length hair was in a ponytail. It took a few long minutes of staring at her before I noticed that everyone was dressed for the tennis court. It turned out that they were all headed to the tennis court for a morning games and I was free to watch them if I wanted. Normally, this would have been something that I passed on, but I couldn’t lose out on the chance to see her looking so sexy and jumping up and down all morning. I went along, but not before she let me in on her secret. She made sure that she was the last one out the door with me behind her. It was a very subtle gesture, but she flipped up the back of her skirt just long enough for me to see the bulge in the back of her white, lacy panties. Then she let the skirt flip back down and turned her head back to wink at me before heading out the door. That was when I knew I was in for a very special day. That bulge in her panties was the buttplug from the night before. She was clearly intent on wearing it all day long to really stretch out her asshole for me. She wanted me to try and fuck her up the ass all over again and I was more than happy to oblige her. All I had to do was get through the hot day and I’d be reared with a whole new night of taboo passion with his married woman. It was going to be difficult to think about all day long, but that was my mission. I had to be discreet about it and not let everyone else know that I had a raging erection the entire time I watched her dance around the tennis court. It was the most difficult every time I saw her skirt flip up in the wind and I knew that I was the only other person who knew our secret.

I couldn’t wait

The problem was that I just couldn’t wait that long. There was a brief lull in the playing and she plopped down next to me on the bench I had been sitting on. She was glistening with sweat and even sexier for it. It was too much for me and I made up my mind. I gave her a very deep look into her eyes and got up to walk to the public restrooms by the court. I didn’t look behind me because I didn’t want to give anything away to anyone who might had seen, so I had no idea if she had even followed me. I got out of sight and finally turned around to see her coming up behind me with a smile. I grabbed her by the arms and pressed her against the wall to shove my tongue into her mouth. She happily sucked it in and we kissed each other with my parents and her husband just a few feet away. That was when I made my first move to take over and be the man that she needed.

More next time

I’ll have more to say about this next time. We had a very fun day and there was a whole lot going on between us. I knew that I wanted her more than anything and it seemed like she wanted the same thing. I’ll get into what happened behind that public restroom and how it cemented this older woman as one of the best hook up I’ve ever had the joy of experiencing in my entire life. She’s an amazing woman and I love to remind myself of that.

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.

This gorgeous, older woman was on her knees in front of me with the butt plug that I had just inserted deep in her asshole. My balls were empty and my cum was still in her stomach, but I could feel my cock start to throb her all over again. It had been a very long time since she had been able to enjoy anal penetration and she was incredibly tight. I could tell that it had taken a lot out of her to accept the butt plug inside her. She was still breathing heavily and she had her head resting on the arm of the sofa. I could also see that her perfect little pussy was dripping with juice. She was incredibly turned on to the point that a long, thin strand of her fluid was making its way from her pussy all the way down to the sofa. That was when I knew what I needed to do for her. She was desperate to be treated like a sexual object and I just couldn’t stop myself from doing it for her. She jumped when she felt it, but she immediately started to moan in pleasure.

I ate her out

I put my hand on her hips and leaned in to suck her swollen clit right into my mouth. I ran my tongue over it again and again and made sure to keep pressure on it. Then I used my tongue to massage her entire vulva from the top right down to the bottom. I even took the opportunity to slide it as deep inside her warm hole as I could get it. I was rewarded with the sounds of her quickly achieving orgasm while I worked. I went back to sucking on her clit and brought my hands up to her naked tits. I kneaded them like dough and twisted her nipples with my fingers. Her entire body moved with my actions and her back arched. I was eating her out for maybe five minutes when I felt her start to cum for me. She shook and her ass cheeks vibrated against my face. She pushed herself into me and I kept sucking on her clit until she collapsed onto the sofa. I made her cum and felt the kind of pride that you really have to work to accomplish. I gave her exactly what she needed and her sweaty, collapsed body was the proof.

I let her recover

I just sat there for a few minutes while she caught her breath. I ran my hand over her warm ass cheeks and loved the way that they felt against my palm. She finally get enough strength back to turn herself around so her head was resting on my lap and her legs were up on the sofa. I ran my fingers through her hair and just enjoyed having her in my presence.

“Well, I wasn’t expecting that, honey! You really know what you’re doing back there.” She said with a smile.

“I just did what I thought you’d like.” Was the only response that I could come up with. Secretly, I was praising myself on the inside for making her cum so quickly.

“Well, thank you. I certainly enjoyed it.”

“So, why did you bring the butt plug?” I had to ask her. It was killing me not to know. I had to her it from her if she had been planning to sleep with me on this vacation.

She laughed softly and nestled her face into my thigh in embarrassment. When she turned her head again, she said “Oh, you figured that out, huh? You’re too smart for your own good.”

I had to know

“I’m just curious. You didn’t bring it for your husband. That means you brought it for us.”

She hid her face again for a minute then turn onto her back so she was looking right up at me. I looked down at her and her put her hand on my cheek.

“I brought it for us, honey. This whole thing was my idea. I’ve been dreaming of this for a very long time. I came up with the idea of a vacation because I knew it would be the best chance for me to get fucked by you. Is that okay?”

I can’t tell you how much pride swelled up inside me right then and there. She had planned the whole thing. She suggested the vacation as a way to have sex with me. She really had fantasized about me just as much as I had fantasized about her. That was possibly the best thing that had ever happened to me up until that point.

“Yes, of course it’s okay.” I said and leaned in to kiss her again.

That was when she got up and made her way into the kitchen. I watched her walk from behind and I couldn’t take my eyes off of her perfect and naked body. The best part was that the butt plug was pushing her ass cheeks out a little. It gave me a perfect view of it, even when she was standing upright. She got a bottle of vodka out of the fridge and two glasses then came back to sit on the sofa with me.

More next time

I’ll have more of this story next time. I can’t say enough just how much happened on this trip. I got to fuck this amazing woman that I had always fantasized about. I seduced her and she seduced me. It’s pretty much the best case scenario when you’re hooking up. Two people that have wanted each other for a very long time finally get to enjoy each other. It remains one of the greatest hook ups of my entire life and I’ll always remember it with both pride and pleasure. Next time we’ll see just how far things went between us on just this first night we had together.

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.

So there I was at the rental cabin. I was on my back on the sofa and my mother’s best friend was on top of me and giving me the best blowjob that I had ever had the experience of enjoying. Like I said last time, we were all on vacation. It was me and my family along with my mother’s best friend and her family. This was a woman that I had always found to be painfully attractive. I had fantasized about her for years and jerked off to her in my room any time she came over to visit. She was in her late thirties or early forties and I had just turned 18. I had made it my job to at least see her naked while we were all together on vacation, but it turned out that I got a whole lot more. Completely to my surprise, she had been fantasizing about me just as much as I had been fantasizing about her. She was on her own mission and I was finally getting all of the things that I had spent so much time fantasizing about ever since I was old enough to get hard.

It started very quickly

Just to recap, the whole thing started when everyone was down by the lake. She was in the cabin by herself and I had to make my way back to use the bathroom. I walked down the hall and heard a whirring sound coming from the bedroom that she was sharing with her husband. Not knowing what was going on, I opened the door and was greeted with a very lovely sight. She was completely naked on the bed and masturbating with a massive vibrating wand. She noticed my intrusion and didn’t seem to mind it at all. In fact, she just looked me right in the eye and had a powerful orgasm right there in front of me. I’ll never forget the look on her face when she came. That in itself would have been a great story to take back home after the vacation, but she wasn’t done with me at all. Overwhelmed with sexual desire, I ran back to the bathroom and started jerking my throbbing cock for all that it was worth. It was only a few minutes of stroking before the door opened and she walked in.

She didn’t let it stop

She just came right into the bathroom with me and closed the door behind me. She told me that I owed her a show and just stood there while I jerked off for her. She even took it upon herself to catch all of my cum on her foot as it shot out of my swollen balls. It certainly saved a lot of time on the clean up because, believe me, I shot a massive load and it would have gone everywhere. The best part was that this was just the first part of the first day. She kept it going later on after everyone else had gone to bed. She sat next to me on the living room sofa and shared all of her secrets with me. Sher told me that the sex with her husband left her feeling more like the mother of his children than his wife and that was why she spent so much time fantasizing about me. She needed someone who could make her feel like a woman again and that person was going to be me. That’s what led to her passionately sucking my dick on the sofa.

It wasn’t just foreplay

Of course, what I thought was happening was that she was just giving me a little bit of foreplay before she got what she really wanted out of me. Those ideas were tossed out the window when I told her that I was getting too close and tried to pull away. She simply held onto my thighs and looked up me with my cock bouncing right underneath her chin.

“It’s okay, honey, you can just cum. I want you to be all emptied out for me.” She said with a smile.

She started to go back to sucking and it felt so good that I was afraid I wouldn’t be able to do anything without at least an hour nap afterward. She was incredibly at it and it was like she was trying to suck out every last drop of me that I had. I asked her if she was sure and tried to hold it back.

“Oh, I know fast you blow your loads when you’re all backed up and excited, honey.” She said after stopping again, only pausing to lick my shaft and run her soft lips over my head. “I’ve watched you run away into your room to jerk off to me for years. Sometimes I even follow you to listen through your door. You shoot your loads all over the place and it’s always over way too fast. I need you to last in my ass.”

And with that, she gave a soft laugh and went right back to blowing me. This was all a major shock to me. I had never even considered the possibility that she knew I was jerking off to her whenever she came over. I really had no idea that she was listening. Just revisiting those days and imaging her on the other side of my door was way too much more me.

She swallowed it all

It must have only been thirty seconds after she started sucking me off again that I started to erupt, and I mean erupt. I could feel what must have been a gallon of cum shout off of me. I never felt her mouth leave my cock for a single second. As soon as the cum shot out, it disappeared. This woman was swallowing me whole and I absolutely loved it. It also made me furious that this sexual deviant wasn’t getting what she needed from her husband. That guy should have been giving her every last thing that she ever needed from him. If she was this desperate to swallow my cum, I could only imagine how happily she would have been swallowing his if he let her. She kept sucking me until long after the spurting stopped and that’s always the best sensation that there is. There are far too many women who stop too soon and it’s always heart breaking. She was taking the time to make sure that I was getting as much pleasure as I could possibly handle.

Then came the cuddling

I knew that she wanted a whole lot more out of me, but she just decided to spend some time cuddling afterward. She crawled up so she was lying on top of me and rested her head on my chest. She started running her fingers up and down my body and just laid there after giving a satisfied sigh. I couldn’t help but just throw my arm over her shoulders and hold her. I could tell that she needed the emotional aspects of sex just as much as the physical ones. If she wasn’t getting them from the man who was supposed to be giving them to her, then I would have to do it. No woman who sucks a dick like that deserves anything less at all. She was a sexual dynamo and she deserved to be held after all of the work that she put into making me feel good. That’s just a rule that everyone is supposed to follow and it doesn’t matter if you want to or not. When a girl sucks your dick and swallows your cum, you’re obligated to let her cuddle with you afterward and that’s just the way that it is.

More next time

There’s still plenty more to this story that I have to tell. She was there to get fucked up the ass that night and I was going to give it to her. I couldn’t send her away and there was really no reason to do it in the first place. Everyone was asleep after a night of drinking. There was no way that they were going to be waking up anytime soon. It was the perfect time for us to do all of the things that we had been fantasizing about for so long. I may not have known that she was fantasizing about me, but it was now clear that she was. That made it my job to make sure that she got to play out as many of those fantasies as she possibly could. If there was a way for me to give her what she needed then I was going to do it for her. She was an amazing woman and she deserved it. I’ll let you know everything that happened next time. Things only get hotter and sloppier from here, so make sure you come back to hear it.