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This is sort of long, but its pretty well to stories in one.
So I finished high school a year ago and I took a leap year and went to travel in Asia with two of my best friends. I got home in the spring and back into the swing of life and began to get ready to go to University in the fall.
I sort of grew up in an affluent area of the city I live in. Since I graduated high school and travelled the world for like 6 months at 18-19, it became sort of fashionable for my parents to invite me to some of their social events. One of the guys I travelled with for 3 months has parents that our friends of mine and they were throwing a party at a hall for a charity and him and I were invited.
So our plan was to go to this adult party and drink all the free beer we could, then go out to meet up with a group of girls who had just gotten home from their first year of university. I had only been home a couple of weeks and really not re-connected with some of my friends yet so this was going to be a night. I tried my best to dress to impress as I had my eye on a girl we were going to meet up with later.
So my two friends and me show up to this hall party and there’s like 6 kegs of beer of beer there that some guy who owned a small brewery had brought that had all been tapped and only 60-70 adults there my parent’s age. We begin drinking and socializing, and a band starts playing a bunch of oldie rock and everyone starts to drink.
So my Mom is introducing me to all these people, then all of a sudden my friends mom pulls me aside and introduces me and my buddy that I travelled with to this woman. She is, for lack of a better word, stunning and milf status at this party that had some attractive older woman at it. She looked a bit younger than my friend’s mom. She had blonde hair, big blue eyes and a really pretty face. She had this really square jaw and really nice teeth that she always smiling with. I’m not even kidding when I say this, picture like a Kate Upton, but a little shorter and 45 years old. She was wearing this low cut spring dress that had black polka dots on it and showed off her big breasts nicely. I don’t know if she has had some work done, but I’ll just say she looked like she really tried to keep herself attractive.
She turns out to be an associate of my buddy’s dad, who is a highly educated medical professional, wink wink, and she recently got back from a conference that she turned into a vacation in Asia.
Her name is Karen and we end up talking with her for a while about travelling in that region of the world and how our experiences were. Karen had a totally different budget than we did on our trip, but she was interested in what we did and saw. She also told us about her two kids and how she had a son who just started high school at the same school we graduated from.
So the conversation with her keeps on going and going and I can tell Karen is really enjoying the attention she’s getting from my buddy and I. Both of us are pretty tall and had grown our hair out on the trip. Not to blow my own horn, but I’d say I am the better looking of the two of us and maybe a bit better with girls than he is. But yeah, I can tell Karen is really enjoying the conversation she’s having with us and she’s laughing all the time and smiling a lot.
All I’ll say is this about Karen and flirting. She had the eyes. Any guy out there knows what I’m talking about when I say this. Her eyes were just so flirty and they dashed everywhere and were all inquisitive and actually interested in me. Every time I’d look over at her later in the night my eyes would meet hers and she give me this flirty look and smile.
The conversation about traveling eventually ends with Karen and me and my buddy’s have drank a lot of keg beer at this point. My one buddy really wants to go meet these girls that we planned on seeing but my other friend who I travelled with is down to stay. I didn’t want to leave either, so him and I stayed and just kept partying with the adults and our parents.
Things then start to get a little crazy. All the moderate partiers start leaving around midnight and a few of the kegs are done. The dance floor is going off with the oldies and the auctions over. My parents, being a little more reserved have bailed. Right after they left I noticed that Karen had gathered her stuff and was looking like she was about to leave too. Earlier in the night we had done like a swing dance thing together and I could tell she was really into it, so I was disappointed that she was leaving because she was easily the best looking woman at the party.
I approached her and asked if she was leaving and she said that she wasn’t, she was just going out for a cigarette. I asked if she wanted some company, being the confident drunk I am, and she smiled. She then made a quip along the lines of "I know, a medical professional that smokes." I couldn’t say no to another opportunity to flirt with her and as far as I could tell, she had come to the party alone, but I did notice when we were dancing that she had a wedding ring on.
When we got outside it was a little chilly and we decided to walk a little ways from the halls entrance to this bench under a tree not far away. When we get tot his bench my heart is full blown pounding because I have this feeling that something is going to happen with Karen. The whole walk there I was trying to convince myself that there was no way she was into it and that there was no way possible it could happen.
So once were at the bench she pulls out a cigarette and lights it, then sits down on the bench and crosses her legs all sexy like. She asks if I want one and I politely accept her offer. We begin talking and flirting some more and I can tell she’s a little more drunk, but at this point I am too, so I’m also more confident and I begin talking to her more like an equal and not a young guy. I asked her where her husband was and all she said was that it was a story longer than she was willing to explain, but it was part of the reason why she was Asia so long away from her family. I made some flirty remark about how the bastard was stupid (because he seriously is) for letting her go.
Then, out of nowhere, Karen runs her leg up mine. I’m standing like a foot from her and she just sticks it out there and runs it from my ankle close to my crotch. I get hard instantly despite the alcohol and the weather, and I’m sure she’s into to me, so instead of backing away, I move closer to her. We sort of lock eyes and I ask her if she meant to do what she just did, but I’m staring at her and I can tell she wanted me. All she does is smile, and I lean in to kiss her. She stopped me before I could, and said that she couldn’t there because we were in public and not far enough away from the entrance.
Then, all of sudden she stands up, moves close to me, and seriously, stuck her hand down my pants while acting all casually, and squeezed my dick. She looked me in the eye and said that she’d be waiting for me in the woman’s bathroom in the far stall and told me not be seen by anyone. As she walked away I sort of called after her asking if she was serious, and she just turned her head around to me and laughed then nodded a little.
I couldn’t believe it. I was totally in shock. I know, at this point it sounds like clichés or a bad porn video, but this actually happened. Up until this point, I thought my conquest of a 27 year old Dutch girl I had met on the beach in Asia was the oldest I’d ever get to at my age. I’m still a little younger looking, but I’ve grown a lot in the last few years and I can tell woman, especially older woman, like me because I can talk to them.
So I let her walk in front of me on the way back into the hall and still couldn’t believe what was going on. I just remember tucking my boner up into my pants to hide it Super Bad style and thinking that I had never had a woman come on to me like that. None of the girls in highschool had ever acted that way and when I was in Asia, it was always me who usually made a move or it was mutual. I watched Karen’s ass as we climbed the stairs and once we got inside, she took a right to go down the hall to the woman’s bathroom. This was actually going to happen and my stomach dropped a little in anticipation.
I stood in the door of the hall and observed the party for a bit. Everyone in there was significantly drunker than I remembered them being. Another one of my friend’s Mom actually passed me to go outside and she almost stumble down the stairs and just laughed when I offered to help her.
I was hesitating. All I could think was, was Karen serious? I went and grabbed my beer chugged it, then said fuck it and literally ran back to the entrance and back down the hall to the bathrooms. When I got there, I decided to just put my head down and go in to the woman’s washroom and act like I was drunker than I was if someone was in there and apologize.
Thank god when I opened that door there was no other woman in their washing her hands, because I would have turned and run the other way. I eyed the three stalls and noticed the one on the end was closed. The lighting in the bathroom was super low, almost to dark to see at that point so it wasn’t a terrible hook up place despite it being a bathroom. I walked to the stall as quickly as I could and pushed on it.
When it opened, Karen was actually sitting on the toilet peeing. She just looked up at me and quietly said close the door. I did and I just stood there in silence while she wiped. Then, she stood up and kissed me. Those big red lips just devoured my mouth and my hands began to make her way down to her chest and up her skirt. It was probably pretty sloppy at the time. She was really aggressive for her size and like a whole new dimension of her personality was on display in that bathroom. She was feasting on me and I was hanging on to survive but it was fun at the same time.
Next thing I know, after she’s had enough of my mouth, she sits back on the toilet and rips my pants down. No girl I had been with had ever done anything like that before. So I’m standing there, full mast and she’s sitting on the toilet and she begins stroking me and looking up into my eyes and all she says to me is that ‘you have a nice cock.’ Then she puts her lips on it and begins taking it like a total champ.
I’m not the biggest guy girth wise, but my dicks a little longer, and Karen is just straight up ravaging the thing. She’s deep throating it and licking the shaft like a freaking maniac and stroking it so hard when it’s not in her mouth that I thought I was going to bust within a minute. Luckily, I’m drunk and thoroughly enjoying myself, but she’s going maniac on my dick. She spit on it and licked up and down the shaft and it was the first time ever a woman had put both of my balls in her mought.
So im standing there, both hands on either side of the bathroom stall and my pants are completely off and I’m so nervous that someone was going to walk in and hear the unmistakable sound of a blowjob going on. It was a total porn star status though, and easily the best I’ve ever had.
Then she just stands up and takes her underwear off and turns around. She’s placed herself bent over the toilet, arms on the top of it and ass sticking out and she pulls her dress up onto her back. Her ass is just there for the taking and her toned legs are spread the width of the bathroom stall. I reached down and stuck my fingers in her and I felt how wet she was. I just kept playing with her and I could tell she’s loving it as she just moved her pussy along with my fingers. I’m just admiring her ass and thinking, shit I don’t’ have a condom, but I’m going to hit this anyway and no one is going to ever believe me.
Then, she said the single sexiest thing anyone has ever said to me. She turned her head around and tells me "Be a man, not a teenager, and fuck me." Hey, ‘medical professionals’ orders
I stuck my cock in her and I begin just going to town on her ass. She’s so wet and really quite tight for a woman her age. I just couldn’t believe how soft her pussy felt. I had only had unprotected sex a handful of times up until this point and I have to say she easily had the best and softest lips I had ever felt. It was so smooth and wet and warm and she was so into it being inside of her. She actually made me stop and pull out for a second so she could remove her shoes and spread her feet wider as I was having trouble getting the whole thing as deep as I could in her. When her shoes were gone I just begin going at it with this perfect milf ass, but I;ve got to keep things quite. I’m only fucking her ¾ length so I can avoid my balls from slapping her and my thighs from hitting her ass. It was perfect actually. She was just the right height to pull it off and I could tell she was loving it because she was panting super fast and hard but she was doing it without and moans.
She still had a bikini tan and everything and she was fully shaved, asshole and everything. I begin to grab her ass hard and she begins to moan real loud to the point I have to tell her to be quiet.
Then, I shit you not, the bathroom door opens and another woman walks into the washroom. My heart fucking sinks and all I can do is pray that the stall were in and the bathroom itself is dark enough so this other woman doesn’t see us. Karen stops moving to and I’m still inside her. This other woman just sort of stops in the doorway then walks into the stall furthest from us which is closest to the door and sits down and starts peeing. At this point I’m still just holding my breath, but the woman in the other stall phone begins to ring and she picks it up. This woman begins talking to who I know is her daughter, because at this point I recognize her voice. I went to school with her daughter and we were friends at one point, and this lady is telling her to come pick her up from this party as her and her husband are just smashed.
Karen, hearing the conversation, begins to sort of relax her pussy on my dick and slowly begins to fuck it again with her ass as I stand still. I don’t know I how she did it, I’ve never had it happen before, but it felt like she actually clamped her pussy around my dick and began pulling and fucking it really slowly. It was honestly the best minute of my sex life so far, this older woman just fucking my cock all nice and slowly, I’m not even moving and she’s bent over a toilet.
The woman in the other stall eventually ends her phone conversation and Karen stops moving again. Thankfully, this woman gets out of the stall and opens the door and walks out without washing her hands because she surely would have seen us in the mirror she glanced in it.
Once she left, I grab Karen’s ass again and begin going at it with her like it’s all business. Tip to balls, tip to balls, in and out and she’s taking it like a total champ and moaning. I can feel that she just keeps getting wetter and wetter and I have no idea but it honestly felt like she began to squirt at one point when I was inside her because my thighs and everything were just soaked with her juices. About a minute after this I’m about to blow my load and I tell her I am, and then she does what is also one of the sexiest things I’ve ever had happen to me, which is she actually put her left had on my ass and pushed me deeper into her. I was about to ask if she was sure, but it was too late. I just let it go in her and filled her up with what was probably a 8 to 10 roper.
After that was finished, I’m just standing there completely exhausted and sweating and Karen turns around and sits back on the toilet. She looks up and me and smiles. Then she says theres no point in telling anyone about this ever, because no one will ever believe you and that it was best for her to not have something like this get out. She then asks me how old I am exactly.
Then, as if it could get and crazier, as she’s wiping herself off and pushing my cum into the toilet, she sticks my cock in her mouth again and licks every last part of it. Holy fuck, the hottest thirty seconds of my life.
I remember she just stood up, told me to pull my pants up and look presentable, and I walked out of the bathroom in a haze and back to the party. I don’t even know who left the stall first or how no-one walked in. Or that no one heard us. When I met my friend by the keg I just told him I had a phone call and then I watched Karen walk out of the hallway, wave the party a good-bye and leave like nothing had happened.
So yeah, the story is fucking crazy. But here’s the crazier part. Last week I’m at another one of these adult party’s at my friends house that I went travelling with and guess who’s there. Karen. And, here’s the even crazier part, she’s talking to my mother. My mother actually see’s me and invites me over to talk with her and introduces me to Karen, who I hadn’t seen since I had her bent over that toilet in the hall bathroom.
Karen just says that we had met before at that party and she says really cheekily that she talked with my friend and me about our travels. At this point, I’m just in total shock and I’m not really saying much and my mom finally leaves the conversation and Karen and I just stare at each other and she smiles.
Here’s where it gets even nuttier. This particular party wasn’t nearly as wild or drunken as the hall party. It was dressier and more formal. So, Karen and I are alone and all she says to me is to meet her in the basement at 11. Again, I’m shocked, but how could I say no. So at 11 o’clock I wander down the stairs and find Karen standing beside a couch talking to another couple. When she see’s me, she sort smiles and motions to me to stay there and I backed away down the other hallway and eventually found the bathroom beside a spare bedroom and go inside.
Next thing I know, there’s a nock at the door and when I open it, Karen walks in. She just looks me in the eye and smiles and says that now that she’s officially divorced she doesn’t need to feel bad about fucking around with her colleague’s son’s friends in bathrooms at parties.
We make out for a bit, and she quickly pulls my cock out and begins to blow me. About half way through it I realize I am going to cum pretty quickly, as I’m not drunk and again, she is great at giving head. Both of us are making an effort to stay quiet. She pulls my dick out of her mouth and whispers to me that I can fuck her another time. About a minute later I sort of tap her head and whisper that I’m going to cum and she just picks up the pace. I blew huge load in her mouth and she swallows everything in like two gulps. It was the sexiest thing I had ever witnessed, then she just played with my cock for a bit and asked if it was good.
After it was over, she stands up and she asks for my phone. When I unlock it, she puts her number in my phone. Then she just leaves and walks back up into the party and I have to act like a milf didn’t just do what she did to me all night in front of my parents and my friends.
We’ve been dirty texting all week and I am going to her place tomorrow night.
I know. So fucking crazy.
BhupperC2014