I’d always been the bad brother. Chris was a year older than I was. He was the jock and got good grades. I was a solid C student and often in trouble in school. On the bright side, I generally got better pussy than he did and I let him know it. Funny enough given our rather antagonistic relationship, we got along pretty well.

After high school, we ended up rooming together. He was in college and I was, well, not. I worked odds and end jobs and did some petty crimes to pay the bills. I learned that girls with drug problems made for some really great lays, so I enjoyed banging the shit out of them all night when I knew that he had a test the next day.

Still, we hung out now and then and occasionally went to parties together. He was getting in with the frat crowd, so, having a fair amount of free time, I often went with him to their parties. Picking up drunk college girls was far too easy and I enjoyed leaving their underwear in the hallway of our apartment for him to find, as he typically got home to find me banging away on one of them. I also enjoyed fucking them in the living room where he would clearly see us banging as he came home.

One weekend, something was different. We were at a standard drunken frat party when my eyes caught something new. This girl had long, dark hair with red streaks in it and was not dressed like a normal rich sorority girl. She was in a black tank top and was wearing a ripped up black skirt with chains hanging off it. As she lifted her cup to her mouth, I noticed an arm sleeve tattoo. Not many girls in college in Texas wear that much black, or have sleeves. She also seemed to be rather bored with the party, mostly hanging out against the wall and slamming drinks. I wandered my way over to her, figuring I’d be far more interesting than talking about football with a bunch of drunk jocks. I wandered my way over towards her, seeing up a red bra and some nice tits as I got closer. She caught my eye as I approached and looked intrigued, seeing as how I was similarly dressed in a non-rich way.

“So.” I started, eyeing her tits.

“So.” She replied, catching my gaze and following it down. It didn’t seem to bother her that I was bluntly checking her out and she followed suit with me. She seemed to be pretty hammered, enjoying the rich kids booze to their fullest.

“You as bored as I am?” I asked her

“Pretty much.” she replied drunkenly.

“Nice tat.”

“Thanks.”

“You got any more?”

“Yeah.”

“Where are they?”

“Wouldn’t you like to know.”

This chick was feisty.

“You here for the free booze too huh?” I asked with a grin

“Pretty much.” She replied. “And some dick.”

This chick was seriously feisty.

“Oh yeah? How’s that going?” I asked, my smile growing bigger.

“Well, I’m still here, so obviously not that well.” She replied, one eye half closing.

“Could have gone into one of the bedrooms and gotten some.” I replied.

“Naw, I’m pretty loud. Especially when I’m getting fucked in the ass. Don’t need to get the cops called” She replied bluntly.

My cock grew hard.

“Yeah? You get butt fucked a lot?” I asked, taking a sip from my drink.

“Not nearly enough. Frat boys get too drunk to be hard enough to stick it up my ass. It’s been a while since I got a good hard fuck in the ass.” She replied, a little too loudly. A few girls turned to look at her, their noses wrinkled.

“Shame. Too bad. A cutie like you should be able to get fucked in the ass whenever she wants.” I replied.

“Aren’t you a charmer?” She replied with an eye roll.

“Nope. But I’m also not a limp dicked frat boy.” I said, moving a little closer towards her.

The girl blatantly reached down and grabbed my cock. I had grown harder during our banter and my cock jumped. She squeezed it a little and looked up at me.

“Nice. Not bad. You’ll do.” She replied, swaying a little towards me. I put my arms on her shoulders to catch her, feeling her tits press against me.

“What’s your name?”

“Ember.”

“So you ready to get out of her then?” I asked.

“I want another drink and then we’ll go.” She mumbled, sticking her cup out towards me.

“Cool.” I replied, grabbing her cup and turning. “Don’t go anywhere.”

“I won’t.” She replied, leaning back against the wall to hold herself up.

“Score. Piece of cake.” I thought to myself as I wandered through the crowd towards the booze. The trip took far longer than I had hoped, making my way through the large crowd and trying to avoid a few fights along the way. As I had feared, when I returned Ember was gone.

“Mother fucker!” I yelled, slamming both her and my drink down as fast as I could.

I was pissed off. I was bored, drunk, annoyed and hard. I cursed openly as I stomped around the frat house, trying to decide if I should start a fight or leave. Luckily, the frat boys were smart enough to stay out of my way. I was apparently throwing off the ‘don’t fuck with me vibe’.

I stomped my way up the crowded staircase, hoping that something upstairs would entertain me. As luck would have it, as I rounded the top of the stairs, a short blond fell into my arms.

“Hehe, sorry.” She giggled, obviously plastered.

“No problem. Nice tits.” I commented, not giving a shit as I stared straight down her shirt.

“Awe thanks. You like them?” She hiccupped.

“Yeah they are cute. Like your lips.” I ventured, starting down a very cheesy path.

“You like my lips?” She babbled, looking up at me with blood shot eyes.

“Yeah baby, they would look really great wrapped around my cock.” I replied, finishing the worst pick up line in history that worked far too often.

“Oh you think so?” She asked.

“Yeah, if you think you can handle it.” I replied.

“You’re cocky.” she said bluntly.

“Yeah, so. You think you’re up for it?”

“Yeah let’s do it.” she slurred.

I grabbed her tiny wrist and pulled her into the first open doorway I could, which happened to be the bathroom. I closed the door behind me to the boos of the crowd as she dropped to her knees and reached for my zipper.

“Oh that’s nice.” She mumbled as she pulled out my cock.

I put my hand on the back of her head wordlessly and pushed her down on my dick. Her wet mouth felt great around my shaft and she did a pretty decent job of taking the majority of my cock. I leaned my head back against the door and fucked her mouth, rocking her head back and forth on my cock with a fist full of her hair. I heard her gag several times but I was past the point of caring. I also didn’t really give a damn as I felt my balls tighten, so I grabbed her head with both hands and shoved all the way in, blasting my cum straight down her throat.

Her eyes bulged out and I could feel her throat contract. The instant I pulled my cock out of her mouth she turned around and shoved her head into the toilet, puking up my cum and lots of alcohol.

“Thanks for the head. Catch you later.” I called out, shoving my cock back into my pants. The girl flicked me off while continuing to puke. I picked up her cell phone which hand fallen out of her pocket and left the bathroom, leaving the door wide open.

I thumbed through her phone as I stumbled my way back to my apartment, enjoying the naked pictures and dirty text messages. I responded to a few, begging boys to come over and fuck my ass later and posting that I’d just blown a stranger in the bathroom on her Facebook wall before throwing her phone in the gutter.

I was feeling better when I opened the apartment door. As I closed the door behind me, I heard something new.

Moaning.

Or, better put, screaming.

Girl screaming.

Now, Chris wasn’t a virgin and he’d brought some girls home before, but not many. Certainly not screamers. Usually quiet, boring sorority girls that made little moaning noises. They were usually cute, but stuck up rich girls that he spent far too much time eating out. Whoever this girl was, she sounded like a fun ride.

I made my way down the dark hallway towards his bedroom and the screaming got louder.

“Fuck me harder!”

“Your ass is too tight! I can’t go any harder!”

“Can’t you fuck me any better than that?”

Now I was highly intrigued. This girl sounded like a fun ride! Curious to see what sort of freak my brother had managed to land, I pushed his door open a crack.

I didn’t really want to look right up my brother’s ass crack, but that was the view I got. Judging on the noises he was making and his slow pace, it appear that he was, in fact, fucking her ass. His room was dark, so I couldn’t get a good look at his girl. But it appeared that she was still wearing her bra and was eagerly thrusting back against him.

“Haven’t you ever fucked a girl in the ass before?” the girl demanded.

“No. First time.” Chris panted.

“I got your cherry. How cute.” The girl spat back. This chick was feisty! I thought to myself.

“It’s really tight.” Chris complained.

“Lay back pretty boy. I’m going to take you for a ride.” The girl called out, pulling her body forward away from Chris. I could hear the pop as his cock came out of her ass.

Chris obeyed and rolled over onto his back as the girl turned around. I could see his cock sticking up and was happy to see that I was quite a big bigger than he was before the girl turned around and sank her mouth down on it.

“Ass to mouth, I’m impressed!” I thought to myself, my cock growing harder.

Chris moaned loudly and put his hand on the back of her head as his sunk back onto the bed. The girl bobbed up and down on his dick in one of the sloppiest blow jobs I’d ever seen. After a couple of minutes and plenty of split slurping, the girl sat up and straddled his waist. I thought she was going to sit down on it, but then she reached back and grabbed his cock. I could see her moving her hand around as if she was looking for something. She struggled for a moment and then lowered her body down on.

I could see the outline of a grimace on her face and then a POP noise, followed by a loud moan from her and a groan from him. The girl put both of her hands on his knees and pushed down, leaning her body backwards.

“Fuck yeah, that’s better!” The girl exclaimed, rocking her hips around on him.

“Holy shit that’s amazing.” Chris moaned.

“I’m going to take you for a ride now.” The girl panted, bucking and rocking her hips.

It was pretty impressive. The girl was clearly drunk, but clearly knew how to fuck. She bounced on him for several minutes before stopping to rest.

“I want more dick.” She said bluntly.

“Sorry, I only have one.” Chris replied.

“You have a roommate don’t you?” She asked.

For a moment, I thought I was going to get pulled into a 3 way. It wouldn’t be my first.

“It’s my brother.” Chris replied.

“I don’t give a fuck. How big is his dick?” She asked.

“I don’t know. Besides, he’s an asshole.”

Asshole huh? Well, I’m glad I knew what he really thought. I was about to stomp off when a car pulled up just outside his window. The headlights lit up his room and I could see black hair with red streaks, and a red bra.

I’ll never know why I got so angry that Chris had stolen Ember that night. I got plenty of ass. Maybe I was just extra mad that he called me an asshole. Regardless, Ember didn’t stay long after I walked back to my room. Even riding his cock in her ass, he still wasn’t enough for her.

I didn’t go to any more frat parties after that, the experience leaving a strangely odd taste in my mouth. Shortly after his experience with Ember, Chris met this girl named Maggie and soon after moved in with her.

Maggie was hot. Chris was fairly short, and even barefoot Maggie was taller than him. Long blond hair and small tits, with a curvy ass. She did have a cute face and fun smile, but there was part of me that really wanted to call some friends over and watch her get gang banged. Maybe it’s because Chris and Maggie were far too cute together. I got sick to my stomach every time I was around them. Maybe it’s because Chris somehow managed to buy a car dealership out of college and started making a shit ton of money. Within a year, Maggie and Chris got married. I went to the wedding, if only for the free booze. Maggie’s sister Hailey, who looked like a clone of her, was there, obviously stealing drinks and making out with anyone she could find. I thought about making a move on her just to fuck with Chris, but jail bait wasn’t really my thing. Maggie and Chris went to Hawaii for their honeymoon, naturally.

I drifted away as Chris and Maggie started their fairy tale life together and I’d really didn’t care much. I followed them both on Facebook, watching their constant road trips for her job and their monthly vacations to Dallas, Chicago and New York. It seemed that they were barely home in Austin, but I suppose that was the benefit of being rich and child free. They took their dog with them on almost every trip, which made me gag. I had just about enough of Maggie’s post about their trip to San Antonio and was about to block them both when I got a text from Chris.

“Hey man, we’re going out of town next weekend and the hotel won’t let us bring the dog. Can you drop in Saturday and feed him?”

So, after not hearing from him in almost a year, Chris asks me to dog sit? I figured that there would be some things I might be able to snag and pawn from his house, so I agreed.

“Where do I meet you for the key?” I asked.

“Don’t worry, I’ll text you a code. It’s keyless.” He replied

“How cute. How high tech.” I thought to myself.

I got his address and doggy food instructions and promised that I’d walk the dog. I didn’t have anything better going on that Saturday, so I figured at least I’d get to see how my rich brother lived.

I woke up late Saturday, hung over from a late night at the strip club Friday and wandered my way to my brother’s place. He lived in the suburbs of Austin, out in the rural rich area. I pulled into his driveway, impressed at his place. I guess the car dealership paid well.

“Or maybe he’s pimping out his wife? I’d fuck her.” I thought to myself with a laugh as I punched in the code and opened the door. Their dog greeted me with a lot of licks and tail wags and I located the food and rubbed his head a bit. Seeing that I had gotten out of bed for such a short task, I decided to help myself to his booze cabinet and wander around his house.

The back yard had a pool and hot tub, and I imagined Maggie and her friends in bikinis, drinking expensive wine while sitting in it. I wondered to myself if he had ever fucked Maggie in that hot tub and grew a bit angry that my loser brother had snagged such a hot piece of ass.

Getting angrier, I wandered around their house, finding my way into his office for some reason. He had a huge wooden desk with an enormous computer monitor. I dropped down into his leather chair and put my feet on his desk, sipping my drink with a growing annoyance.

“So this is how the big boys feel I guess.” I said loudly, slamming the rest of my drink. As I got up go get another my foot kicked the mouse and his screen lit up.

I didn’t pay it much attention but as the screen came to focus, I noticed that his email was open and the subject line of the first several messages were the same. I knew it had to be only one thing.

Craigslist.

I sat back down and peered closer at the screen

“Visiting Kinky Couple for freaky girl” was the subject line of the first dozen or so messages.

My brother had posted an ad for a 3 some.

Woah.

The pervert in me kicked in and I clicked through the emails. There were some real ugly girls that had replied to him, but several really hot ones. Young college girls as well as professional women about the same age as they were. There was even an email from two female roommates, offering to come over together. Lucky bastard. As I read through the threads, I noticed that he had replied to several of them. The girls that had replied made mention of the hot videos and pictures that he was sending, so I clicked on his sent folder.

Sure enough, Chris had been replying to the ads with pictures of him and Maggie. A few of them popped up, some silly pictures of him and Maggie in their pool with their friends, but eventually I got to the good ones. I was right, Maggie did have a hot body. There were pictures of her in her underwear, some down shots of her sucking him, a nice view of him fucking her doggy style, a picture of her ass up in the air with a butt plug in it and a picture of her small tits covered in his cum. As I had suspected, there were also several pictures of their hot tub filled with Maggie and her female friends, all in bikinis with glasses of wine. There were a few topless shots of Maggie and her friend and a handful of Maggie sucking on their tits. As I scrolled through, I noticed a couple of drop box links, which I clicked.

The browser opened up and a video of Maggie kissing a redheaded woman in the hot tub came on. Both women were topless and Maggie was rubbing her friend’s tits. They made out for a long time and I skipped the video forward hoping to get to something better. Eventually Maggie urged her friend to sit on the edge of the hot tub. As Maggie reached up for her bikini bottoms, I played the video.

“Lay back now.” Maggie directed. Her friend was biting her bottom lip.

“I’ve never had this from a girl before!” She giggled nervously.

“Don’t worry, Maggie is really good.” I could hear Chris say as she lay down.

Maggie turned and blew a kiss at the video as she pulled her friend’s bottoms off and spread her legs. Maggie’s ass popped out of the water as she dropped her head down between her friend’s legs. Chris reached up and pulled Maggie’s bottoms down and fingered her pussy a little bit before moving to the side of the women. Maggie’s face was pressed hard against her friend’s pussy.

“How is it?” Another male voice asked.

“Really good!” The redhead replied, panting a bit. The camera turned and aimed up to see another man standing at the edge of the hot tub, watching.

“Hot stuff huh?” Chris asked. The other man nodded.

“You taste really good.” Maggie said, lifting her head up a bit.

“Thanks.” The redhead panted.

“You’re welcome to fuck her if you want to. She loves that.” Chris said.

“Cool man, thanks!” He replied as the video went dark.

“Woah.” I thought to myself

I hit the next link and a video of Maggie on her knees, eagerly sucking Chris’s cock came on screen. It appears to be from the same setting as the photos. Maggie didn’t seem to have any problem taking Chris’s entire cock in her mouth, but with the view of the video, I could confirm that his dick wasn’t that big. Bored, I clicked on the next link.

This video was the doggy style shot from earlier. I could hear Chris grunting and Maggie moaning as he banged her. She did make some cute noises but I wanted to see what else was there.

I hit the next link and the perspective changed. This shot was looking directly at Maggie’s face. I could see Chris in the background over her shoulder. I hit play and immediately I could hear Maggie groaning loudly.

“Oh baby, fuck my ass!” she panted.

“Damn. Maggie likes it up the butt! “ I said out loud, turning the volume up

“Tight ass baby!” Chris grunted.

“Hurts. I love it when you fuck my ass! Fuck it harder!” Maggie moaned.

My cock started to stir.

I watched Chris pound her butt for a few minutes before pulling out and cumming on her back.

I clicked on the next link.

The setting of this video was entirely different.

The background was a lot brighter and I could hear the noise of the ocean in the back ground. In this video, the person holding the camera, who I presumed to be Chris, was standing at the edge of the bed looking down. In the middle of the bed was a woman, who I presumed to be Maggie, naked, in between the legs of a hot brunette. The brunette was moaning loudly and had one hand on the back of Maggie’s head and the other was rubbing on her fairly large tits. As the camera moved around I could see bikinis and other clothes on the floor and several empty wine bottles.

“Fuck Maggie you do that so good!” The brunette moaned as Chris moved behind Maggie for a different perspective.

“That’s so fucking hot.” Another voice came from off screen.

“No kidding. Just getting started.” Chris replied from behind the camera, turning to answer the other person.

There was another man standing next to the bed, naked, stroking his cock.

“You like the view?” The brunette asked the other man.

“Fuck yeah I do. How’s she doing Katy?” He asked.

“Fucking amazing! Her tongue is incredible! But then again, she’s been doing this a while.” Katy giggled.

“Since High school right?” The man asked.

“Yup, and all through college. Isn’t that right sweetie?” Katy purred.

“Uh huh.” Maggie looked up and nodded.

The video went on for several more minutes, with Maggie licking out Katy and Katy moaning and rubbing her tits. Eventually the other guy climbed onto the bed and put his cock into Katy’s mouth, which she eagerly sucked on. The video bounced around and then cut off.

I anxiously clicked on the next link, hoping it was more of the same.

The video opened up to the same room. However, this time it appeared that Chris was sitting down, since the video was a lot lower in the frame. Also, now Maggie and Katy were kneeling next to each other, alternating sucking the other man’s cock.

“How is it?” I heard Chris asked.

Maggie pulled off the other man’s cock, which was quite a bit larger than Chris’s and held it out to Katy. As the brunette sunk down on it, Maggie turned towards Chris.

“Fucking great! I love it! You know how much I love sucking dick.” She replied lustily.

Katy pulled off of the man’s cock and held it back out to Maggie, who eagerly sunk back down on it.

“All the way baby!” The man grunted, putting his hand on the back of Maggie’s head and pushing her down.

I could hear Maggie gagging as she tried to take it all down. Katy’s hands roamed over Maggie’s little tits as the man pushed Maggie’s head down hard before finally letting her up. As Maggie pulled off, a long line of spit trailed from her mouth to his cock head. He thrust his hips forward again into Katy’s now waiting mouth and this continued for several minutes.

The screen went dark and I clicked on the next link.

The view was of a man’s ass, which I didn’t appreciate, but it quickly moved to the side. This shot was over the other man’s shoulder and I could hear the sounds of bodies slapping. As the perspective changed, I could see Maggie lying on the bed with Katy between her legs. The other man was behind Katy, furiously fucking her.

Maggie was rubbing her small tits and was alternating between looking at the other man and then back to Chris.

“Fuck her Taylor. Fuck her good!” Maggie moaned, pinching her own nipples as Katy lapped at her pussy.

Chris walked to the side of the bed so I had a great perspective of Katy’s big tits swaying under Taylor’s thrusts. Maggie’s slender leg was wrapped around Katy’s head and I could see Taylor sweating with effort.

Maggie turned and looked at the camera.

“Can I go next?” She asked.

“Sure baby, whatever you want.” Chris replied

“I want to cum first! I’m almost there!” Katy cried out from between Maggie’s legs.

“Hurry up then, I want some more of that dick!” Maggie said loudly with a giggle.

“Woah!” I said loudly, eagerly clicking the last link.

The perspective of this was the same, from the side of the bed. Taylor was standing up and Maggie was on her back with her legs on Taylor’s shoulders, with Katy sitting on her face. Katy was rocking back and forth, rubbing her own tits while Taylor pumped Maggie.

“Damn girl, you’re going to make me cum again!” Katy exclaimed.

“Cum on my face!” Maggie moaned, her voice drowned out by the sounds of Taylor’s hips slapping against her thighs.

“How is she?” I heard Chris ask, a little strain in his voice.

“Her pussy feels fucking great! We should do this more often!” Taylor grunted, giving Chris thumbs up.

“You two should see our new place when we get home.” Chris replied.

“Katy can take care of that for you.” Taylor replied, motioning towards Chris. The camera looked down to see Chris stroking his small cock.

“I’m good.” Chris panted. “You want to try her ass? She loves it in back.”

“Hell yeah! You don’t mind?”

“Go ahead.”

“I want to see!” Katy exclaimed, spinning so she could face Taylor.

“Hold her legs.” Taylor directed. Katy grabbed Maggie’s slender ankles and pulled them backwards while positioning her pussy over her face. I could see Taylor fisting his cock and re aiming it. Chris moved up a little closer to the bed and I could see Taylor’s cock pressing against Maggie’s asshole. Taylor grunted as he pushed in and I could hear Maggie moaning loudly. My sister in law screamed as he sunk into her ass, but those screams quickly turned to moans as he bottomed out in her ass.

“That’s so fucking hot!” Katy exclaimed as Taylor started to pump Maggie’s ass.

“When are you going to let me fuck your ass?” Taylor asked, panting loudly.

“Maybe one day.” Katy replied, moaning loudly as Maggie resumed her pussy licking.

Taylor fucked Maggie’s ass for several minutes, in which time Katy came on Maggie’s face and rolled off. Chris climbed on the bed next to his wife and jacked off on her tits as Taylor folded her legs up next to her head and pounded her ass before pulling out and cumming on her stomach.

“That was so fucking hot!” Katy exclaimed, slowly sliding over to the sweat covered Maggie.

The screen went dark.

Damn.

So, they my brother and his wife were swingers?” I thought to myself. As I clicked through the emails I noticed a variety of photos and small video clips that weren’t in the drop box links. Based on the length of Maggie’s hair, I presumed that some of them were older than others. On a hunch, I opened up the photos directory on the desktop.

“Jackpot!” I exclaimed.

Chris had very neatly organized all of their trips by location name. Inside of the ‘Hawaii’ folder were Facebook friendly photos of their vacation. Inside that folder was one marked XXX, which contained all of their sex pictures and the videos I had just watched. I clicked through them, seeing that the Katy had been one of Maggie’s bridesmaids in their wedding.

There was a folder called Home, which as you would expect, was dirty pictures and videos that they had shot at home. There were plenty of sexy shots of Maggie in bed, teasing and playing with herself. There were a few pictures of them fucking on the desk where I was currently sitting. They seemed to enjoy fucking in the pool, as there were tons of pictures and videos of partying out back with their friends, both naked and dressed.

As I clicked through the folders, I discovered that on every trip that they went, they typically hooked up with a girl or a couple. There were tons of pictures and videos of Maggie pussy licking and dick sucking. They seemed to be pretty adventurous as well. In their ‘Colorado’ folder there was documentation of them hooking up with a couple on the top of a mountain during a hike. Maggie was eating out another woman on a blanket in a field while getting railed from behind. In the ‘New York’ folder, there was a video of another man fucking Maggie against the window of a hotel, in broad daylight.

When I got to their ‘Chicago’ trip folder, I noticed that there was an additional sub folder named ‘Maggie Birthday’. I opened it up to see some pictures of Maggie in a dress and some video files, only these were huge. I opened up the first one.

It appeared that this was a new camcorder and it was on a tripod, based on the resolution and the fact that it wasn’t moving. I could see Chris’s leg sticking into the frame in one corner. Maggie was standing in front of Chris in what appeared to be a very high end hotel. The room and the bed were huge. Maggie was wearing a super sexy black bra and stocking and garter set with some heels that made her long legs even longer.

“I’m nervous.” Maggie said to Chris.

“You’ve wanted this for a while” Chris replied.

“I know. I just hope they like me.”

“They will love you. You’re super-hot and you’re an awesome fuck. How could they not like you?” Chris replied.

“Awe, thanks baby. This is just my first time doing this.”

“I know, that’s why we saved it for your birthday.”

“You’re the best.” Maggie replied, strolling over to Chris and kissing him passionately. They made out for a minute, Chris’s hands running over Maggie’s ass when there was knock on the door.

“Oh my God they are here!” Maggie shrieked.

“Don’t keep them waiting!” Chris laughed. Maggie turned and ran towards this door.

“This should be interesting.” I said out loud.