Story Details

Pool Party Gone Wrong

reefermadness on Cheating Stories

Let me just start this off by saying that I am waking up this morning (actually, technically it's the afternoon now) with a wicked hangover after a major mess last night. Waking up alone, with my girlfriend nowhere to be found... I mean, normally I would be stressed out or panicking about the prospect of another failed relationship, but quite frankly my head is spinning too much to even go there.  I guess the best thing for me to do in order to make sense of this whole situation is to write it down, so here goes...

My girlfriend Kayla and I have been dating for a little over a year now, living together for just under 3 months.  She's young, 22 years old, working part time at a videostore while taking an art class or two at the local college.  I'm 29 and I work for a major investment firm.  I guess anybody with have a brain can figure out the score here... while I'm not rich per se, I'm definately not worried about where the rent money's going to come from and I can afford to go out to dinner, clubs, travel, and all that good stuff.  Kayla knows a good situation when she sees one, and it's an arrangement I can live with.

I guess the main reason I got involved with Kayla was the obvious.  She really is a piece of ass.  She's about 5'8" or something and couldn't be more than 120 pounds.  The thing I noticed about her first was the way she looks in a pair of jeans... she has these long legs that make me more jealous than anything nowadays because guys are always turning their heads when she walks by.  She has a great tight ass and, while her tits are probably a B cup, they are perfect for her body type and have the perfect sized nipples.  She has long brown hair and a really cute face, with a great set of lips and nice blue eyes, if you're the type who gives a damn aboutt hat sort of thing.  

Anyway, our relationship started out really hot and wild and it stayed that way for months.  We'd see each other 2 or 3 times a week and we'd tear each other apart.  Usually she would end up panting and covered in sweat (or my cum) and moaning even 20 minutes after we fucked each other to pieces.  I can honestly say that she was and still is the best fuck of my life.  She is in such amazing shape that she can ride me cowgirl style pretty much for 45 minutes straight, changing tempo and keeping my cock in a constant state of near-orgasm.  Simply put, she is an unbelieveable lay, once in a lifetime kind of thing.  She would always tell me that I could fuck her like no other, and I believe it... she would cum several times each time we do it, even when we'd do a quickie in the car or other places where it's usually wham-bam-thank you ma'am.  I mean, I'm a good looking guy with a pretty big cock and I love eating pussy and making her cum, so I guess she has nothing to complain about.  All in all, I don't think either one of us could have asked for any better.

Then, she moved in.  

Suddenly, the sex slowed down.  I'd come home from work and she'd be tired from doing nothing all day.  We'd get into little arguments that would escalate into this big drawn out wars that really put a damper on things.  Communication started to break down, and before you know our sex would start becoming routine.  Time for bed, brush the teeth, floss, get underdressed, fuck for 10 minutes, go to sleep.  Shit like that.  Suddenly, we weren't all over each other when watching a movie, we didn't go out to eat anymore, and most of all, she stopped dressing to impress.  Jogging pants and sweatshirts and hair always tied back in the ponytail.  I admit, I could've probably done a bit more to encourage her, but I guess I had kind of started to lose interest too.

The other day, I'm on the computer and her messenger thing pops up.  I guess she left it logged in.  I see this message from a guy named Todd, so I couldn't help but read it.  I won't lie, there was nothing incriminating in there (trust me, I read the whole message archive!).  Some guy from the videostore, the assitant manager or something.  The message was just them going back and forth talking about some work bullshit, but I got the impression that there was an undercurrent of some heavy flirting going on.  I couldn't put my finger on it, but maybe I'm just the jealous type.  One way or another, this guy was now on my radar, although there was no real way of bringing it up to Kayla.  I asked her some vague questions about her work but she wouldn't really offer too much.

So this all leads me to last night.  Kayla was invited to a party at a co-worker's house, actually the co-worker's parents house, and I saw this as a great opportunity to get introduced to this Todd character and see if my suspicions were warranted.  We drove out there at 5:30 because it was a barbeque pool party, and Kayla was dressed in a loose denim mini skirt, a bikini top, and a pair of those ridiculous oversized sunglasses that's been in style.  We had a little argument that morning over something pointless, so we didn't talk much on the way there, besides her saying that she wanted to get hammered.  I was definately thinking along those same lines, given the fact that I wouldn't really know anyone at this party anyway.

The party was actually pretty good though.  Lots of people, and some pretty hot girls too.  One girl named Carrie was there that I knew from highschool that I hadn't seen in ages, so we hit it off right away over some burgers and beers and talked for a long time.  Meanwhile, Kayla was off talking to some friends or swimming in the pool, and I was cool with her keeping her distance anyway, so I was enjoying myself.

Carrie is shorter than Kayla, with short black hair, a cherubic face with really cute dimples... okay who am I kidding, she really has an amazing set of tits on her.  They are big and round and with her sitting there in her one piece bathing suit I kept getting glimpses right into a canyon of cleavage that after a few beers had me trying desperately to hide my raging hardon.  Carrie has these really full, red lips and a gorgeous smile that made me thinking about how she'd look with them locked around my hard cock.  Okay, so I was horny and having dangerous thoughts.  Could you blame me?  I had blue balls for a week now and I needed something to look at, if only to give me inspiration to jerk off in the shower the next morning.  

Anyway, at one point Carrie went inside with the rest of the party when it started to drizzle.  I looked around for Kayla and I saw her sitting under an awning by the pool house, talking to some guy.  Right away, I sized him up as "the" Todd.  He's not bad looking, taller than I am but not as ripped, kind of on the skinny side and with one of those spiky emo haircuts that I think make guys look gay.  He dressed like some frat boy and he looked pretty harmless, so I went inside to get out of the rain.  

After about an hour, I started getting restless.  Carrie had disappeared, so I was sitting on the couch drinking a Bud and watching TV with a couple of people I didn't know.  I was pretty bored, so I got up and started walking around half-looking for Kayla to see if I could pressure her to get going.  I looked all around the house but I couldn't find her.  Then I remembered where I saw her outside, so I went to the window to see if she was still there.  She was.

It was pouring rain out, and she and Todd were standing there under the awning looking as though they were considering making a run for it into the house.  They were giggling and laughing, and I could see Todd's lips counting down from 10.  When he got to 1, they ran hand-in-hand towards the house.  The thing is, they made it about half way when all of a sudden they veered off to the right and ran to the pool house instead.  I guess they didn't want to get soaked in the downpour so they diverted to another dry spot.  I don't know why I just stood there watching, but when I saw Kayla lead Todd into the pool house, my heart started to race.  It was innocent enough, they just wanted to get out of the rain, but it was the look on her face when she led him in through the door that made me wonder what was going to happen.  I've seen that look before, and I know what it means... she wants something!

Like I said, I was just standing there staring out the window, my eyes focused on the door and window of the pool house.  I wasn't angry, and I definately wasn't upset.  Curious would be the most accurate description of how I felt.  What the fuck was she up to?  Was I right all along about this Todd character?  Is Kayla cheating on me?  I had to know.

I walked around to the other side of the house and opened the patio doors to go outside.  Nobody was around that part of the house, so I was able to creep up to the window of the pool house without being noticed.  It really was raining though, and within seconds I was soaking wet.  I was so focused on not getting too wet that I almost forgot about what I was there to see, but when I made it to the tiny window and looked in, everything came back into focus.

There was Todd, facing me on a small loveseat, his head back and eyes closed, with my Kayla on her knees in front of him.  I couldn't see her face, only the back of her head, but I could see she was working him good.  Her head was bobbing up and down with a really good rhythm that I know so well.  I touched the door handle and was seconds away from bursting in there and kicking the shit out of him, but I stopped myself.  Even now, I still don't know why I didn't go in there.  It's so out of character for me, but I had to keep watching.  I just had to see this.

Kayla was giving this guy some serious head, and his hands were in her hair and rubbing the back of her neck while she sucked him off.  At one point, she reached back and in one motion undid her bikini top, exposing her back to me and her tits to Todd.  He reached down and starting fondling them, at which point Kayla really went nuts and started what looked to me like some deep throat action.  The guy had the biggest smile on his face, like he couldnt believe his luck.  

This went on for three or four minutes or so, until she looked up at him and said something.  He nodded, and she stood up, still stroking what turned out to be a pretty big cock, and kissed Todd on the lips. He put his hands around her back and started rubbing her ass under her miniskirt.  It looked like a pretty passionate kiss that went on for a while; the only breaks was when he reached down to suck on her nipples while she continued to stroke his rock hard cock.  Finally, Kayla stood up straight and pulled down her bikini bottom from under her skirt, climbed into Todd's lap and slipped his dick into her pussy.

I couldn't see Todd's face anymore because the back of her head was blocking, but I still know the look he must have had on it.  Elation.  I know how hot, wet and fucking tight Kayla's pussy is, and when she started riding him slow, all the way up and all the way down his cock, I know he must have been in heaven.  And still, I just stood there like a douchebag, watching my hot girlfriend fuck some stranger.  But I couldn't look away.

After several minutes of this, Kayla gradually picked up the pace, squatting on his cock and really fucking herself hard on it.  I could hear her moaning and groaning through the glass, and talking a whole lot of shit.  It was muffled, but I could definately hear her telling him how good he felt.  "OHHH You're so big" was one thing she kept saying over and over.  She really looked like she was enjoying herself.

Finally, she collapsed onto his chest and started screaming as she came hard all over his cock and balls.  She stopped riding him and he just held her there, cock buried all the way inside her, as her body shook from a powerful orgasm.  Her moans were really loud now, and if it wasn't for the torrential downpour I was sure the neighbours would have heard it, if not the party-goers.

Todd, to his credit, didn't stop there.  He flipped her over onto her back and spread her legs wide and started fucking her missionary style while she slumped on the couch.  Her legs were moving around alot, sometimes wrapping themselves around his back, other times spreading wide, but mostly just flailing about as though she was too lost in the sex to have control over them.  At one point, Todd put one of her legs over his shoulder and started pounding into her hard.  "Fuck me!" she kept screaming, and when he started moaning and groaning I knew the end was near.  Finally, he grunted and cried out, throwing his head back and pushing his cock all the way into her.  I could see Kayla's face now, and she looked positively possessed.  She had this greedy look on her face and a huge smile as she looked up at his face; you could tell she wanted nothing more than to have his cum flood her pussy.  She ground her pelvis into his, licking her lips and crying out as Todd pumped what must have been a massive load into her tight little cooze.  When he finally came down from his high, he bent down and they kissed passionately.  

The funny thing is, it wasn't the sex that bothered me so much as the fact that 1. he came inside her, and 2. the way they kissed afterwards, with her hands in his hair and tongues all over each other, that I knew this wasn't just some fling.  These two were really into each other, and this probably wasn't the first time.  As I walked back into the house, drenched from head to toe, I finally began to feel pangs of jealousy and anger.  It was like my brain had been asleep the entire time I stood there watching them.

I walked over to the bathroom and went in to dry off.  I toweled my hair dry and removed my T-shirt and wrang it out in the sink.  I stood there looking at myself in the mirror for a really long time, wondering what the fuck I was going to do.  Just then the door opened and Carrie walked in absently, laughing to someone behind her and she made her way into the bathroom.  "Oh!" she said when she noticed me, and I smiled at her.  She smiled back, and I know she was looking at my barechest and muscles.

"Hey Carrie" I said, walking towards her with a big grin on my face.  Her expression changed from smiling to confused when I put my hands on her hips and moved in for a kiss.  "What the fuck are you doing?  You're drunk!" she cried out as she shoved me away from her.  At this point, a friend of her's who was right behind her poked her head in to see what all the fuss was about.  I was backed up against the sink at this point, looking at Carrie's hot body and big tits and just wishing that I could have a piece of that.  I moved over to her again, and I guess she was still in a state of shock, because when I kissed her on the lips this time, she didn't push me away... well, not right away.  After a couple of seconds she shoved me again and spat into the hair.  "What the fuck don't touch me!" she yelled out while I just stood there staring dumbly at her face, wondering how the fuck this could have gone so wrong.  To make matters worse, right over Carrie's shoulder I saw Kayla, looking at me with this "oh- my- god- i've- never- been- so- shocked- in- my- life" look that was pretty priceless, considering what I just saw.  "You fucking BASTARD!" she yelled at me, storming off.  

"Kayla, wait!" I said, lunging after her.  Everything might have been fine if I hadn't practically ran over this waterpolo player guy trying to get to Kayla... this guy was huge and he practically picked me up off my feet and tossed me to the ground.  Sandra, the girl whos party this was, was trying to do damage control, but with all the yelling and screaming going on there wasn't much hope of that.  Before I knew it I was out on the front porch of the house in twilight, walking towards my car holding my T-shirt, wondering where the fuck Kayla got off.  Fucking bitch, she thinks it's okay to fuck some clown at a party but I can't take a little piece?

Anyway, I heard people saying as I left that they were gonna call the cops if I drove, so I figured I'd cut my losses and I just started walking towards the main street so I could catch a cab.  I was pretty loaded after all, and getting nabbed for DUI is just what I needed... I figured I'd worry about the car the next day.

So here I am, the next morning, waking up in a bed by myself, my girlfriend (or ex girlfriend I guess now) obviously is off somewhere dozing peacefully in the arms of this fratboy, while I sit here wondering what the fuck happened.

And I still have to go back to the house and get my car.  

What a weekend!

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