It had been over a year since my wife, Erin, and I had last visited Chicago to see her sister Meredith. On our previous trip the three of us and Meredith's roommate ended up fucking in our hotel room.
For any those that have read my previous story (Chicago Sister-in-Law), you know last year I fucked my wife Erin's younger sister (Meredith) and her roommate. They all had fun with my 10" cock and with each other. In the past year, Meredith graduated from college, found a job, and has become increasing flirtatious with me. I love it and Erin thinks its funny but it can be awkward when we're around her parents!!!
Anyway, some of my college buddies were planning a guys weekend in Chicago where we had also all gone to school. It ended up being 6 of us total and all we really had planned was a Cubs game on Saturday and lots of drinking. At the last minute Erin asks if she can drive up with me and she'll hang out with her sister. Meredith had just gotten a really good job and moved into a new apartment and wanted to show her sister. I had no reason to say no although I thought she was infringing on my "guy time" so I just gave in.
I dropped her off at Meredith's apartment Friday night and stopped in to say hi. I had just seen Meredith 3-4 months ago but since she got her new job and apparently a hefty pay increase ,she rewarded herself with a boob job. She used to be a medium 'B' cup but was now a 'D'. A bit too big for her frame but trust me, no one would complain. She gave me this long hug and a peck on the lips and I could feel my cock growing in my pants so I pulled away. I was getting ready to leave when her new roommate came home. Her name is Rachael and she was drop dead gorgeous. 5'3, 100 lbs, perfect 'c' cup tits, long blond hair. But it was when she turned around and I saw that ass; she had on these tight pants and her butt just popped perfectly. We exchange pleasantries and I go on my way.
On Saturday my buddies and I go to the baseball game at noon and bounce around from bar to bar. At about 6 we swing by the hotel and get changed for dinner. We've had a great time all day then right around 10 as we are paying our bill, I get a text from Erin asking if we want to meet her, Meredith and Rachael at a club. Now none of are club guys, we're all in our early thirties and that just isn't our scene. I tell her no thanks so she replied with a picture of the three them slutted up, ready to go clubbing. Erin had on a skin tight shirt dress that was very short. Meredith had on a tiny t-shirt, mini skirt, thigh high fishnets and some serious fuck me heels. But it was Rachael that made up my mind; a bra top and a skirt that went about 2 in. below her ass cheeks. I showed the boys and we we're all in.
We wait in line for about 15 minutes and head for the bar. The place is packed so it was a little while before the girls saw us. The looked even hotter in person; if I didn't know any better I would have thought they were strippers. Meredith gave me another tight hug but this time the peck turned into a kiss. All my buddies are in awe. I've never shared with them my last trip so they had no idea what to expect. Rachael then gave me an unexpected hug and whispered in my ear, "I know what you're packing down there". She gave me a sexy fucking look and walked over to Meredith and Erin. They said they wanted to dance and none of us wanted to partake yet so they went on their way. As they were walking to the dance floor, they mooned us to reveal none of them were wearing panties. All of our jaws dropped and my friends were just like what the hell is going on!!! My cock is growing in my pants and I'm sure their's were too.
At first the girls are pretty tame. Just dancing with each other, keeping it R rated and not NC-17. But after about 30 minutes, Meredith and Rachael start grinding hard and then they begin making out. Of course this drew the attention of about every guy there so we can't see anything anymore. We get up and walk over and by this time Meredith is grinding with 4 guys and now its Erin and Rachael dancing together. After a lot of encouragement from the may on-lookers they kiss. Rachael then lifts up Erin's dress, grabs her ass, and starts to full on make out. Meredith sees me and runs over, lifts up her skirt and starts grinding her bare ass on me. She goes harder and faster until I'm erect as can be. I look over to Erin and she doesn't even notice because she's so busy with Rachael which makes me even more excited.
My drunk friends have no idea how to react and quite frankly neither do I. Finally Derek makes a move toward Erin and Rachael. Derek is obviously the one who has always stood out in our group; he was on the basketball team in college. 6'6" and black, he didn't fit in with the short white guys. He got behind Rachael and started dancing with her. At first Erin objected but she just wanted to have fun. So she lifts up the front of Rachael's skirt and starts to play with her pussy. She then leans over Rachael's shoulder and kisses Derek. I was a bit shocked by this but how could I judge. Rachael slips out of the way and Derek and Erin start to go at it. He grabs both of her ass cheeks and lifts her up, she wraps her legs around him and he starts to pump her. Her ass is up in the air for the world to see and I was honestly loving it. I've never been the jealous type and I think a lot of that has to do with having a big dick but I knew how big Derek was. Back in college, the two of us kind of had a rep for having a couple of the biggest cocks on campus and on a few occasions we double teamed chicks. He is longer bit I'm thicker; either way he had a cock that she would love. Rachael is now face-to-face with me and starts to unzip my pants. I'm not sure how but I stopped her and suggested we grab a cab a head back to the hotel.
There is a van cab right out front that seats 7 but the 9 of us squeeze in. One up front, then me, Erin, Meredith and Derek in the middle and Rachael and two of my buddied in the back. Erin is sitting next to me and asks if I'm comfortable with whats going. I tell her I'm having a fucking great time and then she whispers, "what happens in Chicago, stays in Chicago". She grabs my hand and slides it into her pussy and she is dripping wet. I'm trying to be respectful of the cab driver so I pull back but then I turn around and my friends in the back are both fingering Rachael. She is getting louder and louder and then we finally arrive back at the hotel. We had 3 rooms but everyone headed up to mine and Derek's except for my one married friend and me. He went to bed and I went to the front desk to see if they has a jacuzzi suite available. Turns out they did so I went back to the room to tell everybody. I was half expecting to see a full on orgy but to my surprise everyone was fully clothed and another one of my friends was passed out. So the girls, Derek, Keith, Greg and I pack up our booze and head up to the top floor. The room was huge; 2 king beds, a separate living room, and of course the jacuzzi. It looked like it was made for 4 but definitely big enough for more.
We're all doing shots waiting for the jacuzzi to fill up and honestly things were starting to cool down. The conversation was casual and no one had touched anyone else since we got to the hotel. Finally the jacuzzi fills up and all 3 girls strip down to nothing. The guys then take off everything but our boxers and we all cram into the hot tub. I felt a little bad for Erin because her boobs were so much smaller but she has a tight ass body so she was all good. We're all still drinking quite a bit and finally Erin says she wants to feel the difference between fake and real tits. She walks over to her sister and Rachael and feels them both up. Their racks are both huge so she takes her time and the longer she does it the hotter it gets, So Meredith then says to Derek, "I hear your cock is bigger than Shawn's". We argue back and forth like we have dozens of times so finally Erin shouts out, "Lets just fucking see them!" Neither of us is bashful so we remove our boxers and stand up. Meredith walks over to my semi hard cock and starts to suck it. It doesn't take me long to get rock hard but she didn't stop. I give Erin a look and she slides over to Derek and takes his big black cock in her mouth. She can suck cock like no one else I have seen so he is erect with seconds. Eventually the sisters both step back and then Meredith moves over to Derek and starts to lick his balls and Erin goes back to town on his dick. It was the hottest think I have every witnessed (so far); 2 sisters enjoying a huge black cock together. You could tell Derek wasn't going to last too much longer so he pulled out of Erin's mouth and Meredith stroked him on her sister's face!! He unleashed loads of cum on her face and tits (she fucking loves that). Rachael and Meredith then starts to lick the cum off Erin's tits and face. I almost came right there.
It started to get pretty hot between the 3 girls but there are 3 guys about to explode and a 4th who was ready for more. I grab Meredith by the hair, pull her back, and slide my cock in her pussy from behind. I'm pounding her but I want to see those titties so I lift her on the side of the jacuzzi, put her legs on my shoulder and pound her tight pussy. Meanwhile, Keith and Greg have been neglected the whole night so Rachael and Erin decide to torture them some more. Erin tells them all to sit on the edge of the hot tub; she thens spreads Rachael legs and begins to eat her twat, completely ignoring my friends. Eventually they both sit up and move behind Erin and play with her pussy. She then turns around and screams at one of them to fuck her. Greg it quicker so he stands up and starts to fuck my wife, only he knows her pussy is spoiled so he goes right for her asshole. This is the first time I ever saw my wife get fucked by another man but I'm so engrossed with Meredith I can barely pay attention. I do hear Greg cum and see Keith take his place, although he went for Erin's pussy. Meredith has her legs behind her head and I'm pounding her as hard as I've ever fucked anyone. She starts to cum and lets out a scream that stopped everything (except me). It was a bit scary actually. I'm not sure what happened next, but within seconds Erin and Rachael both climaxed, I came in Meredith and Keith shot in load in Erin.
Everyone is pretty spent except for Derek who has had some time to re-group. He's been sitting on the edge of the bed trying to stroke himself back to life but just isn't there yet (in his defense, it does take quite a bit of blood to get a big dick hard). All 3 girls get out of the jacuzzi and walk over there, hand in hand, with one goal: to get Derek hard again. Rachael goes for the balls as the sisters take turn on his cock. At one point Erin was essentially jerking him off in her sister's mouth and that is what worked. Rachael was itching for some cock but Erin wasn't about to give up Derek's swollen dick. She told Rachael to fuck me because she NEEDED his black cock in her.
Erin pushed Derek back on the bed and straddled him reverse cowgirl style so Rachael did the same to me. She sat on his chest and admired his cock, He was playing with her asshole and she licked his stomach, cock and balls. Rachael and I, in the same bed as them, followed their lead and fuck did I love the view. She had the best ass I had ever seen. I'm still not hard so Erin yells at Rachael to suck me. So she leans forward and does the best she can but it was her ass and pussy in my face that got me hard. I can tell Erin is ready to go so she mounts Derek; slowly sliding down on his long cock. She struggled more than I thought but she took it fairly well. Rachael on the other hand did her best to mimic my wife but her pussy was much tighter. She slid about 3/4 of the way down and stopped. She looked in the mirror in front of us and couldn't believe there was more to go. She slowly inched more and more in and her cries got louder and louder. Eventaully her perfect ass is slamming onto my stomach as she rides me harder and faster. The first time she came I thought she was going to snap my dick off. I see Erin looking next to her at Rachael and she looks back at Derek and says. "thats what I want". I knew what was next; Erin got on her knees, placed a pillow on the headboard, reached back, spread her lips, and told Derek to pound her. He wasted no time and within seconds was fucking her as hard as he could. Because hes so tall he was at an angle I can't get to so he railing down on her and she fucking loved it. Rachael does the same and fucking her doggie style was a dream. I just stared at that ass as she begged me to fuck her harder. Both of them are screaming and Rachael came again.
I think Erin climaxed too but she wasn't satisfied. She told Rachael to get out of the bed and told me to stay. She sat up and removed Derek's cock from her pussy and I look over and the rest of the group is just staring except for Meredith who was recording it!! Seconds later Derek jizzed in her pussy and three of us laid there for a minute. Meredith hands me the camcorder and told me to pay close attention. Her and Rachael then get on the bed and start to lick the cum from Erin's ass and pussy. Trust me, I didn't miss a minute of this.
The two of them spent a fair share of time with Erin but I think she was finally satisfied. Greg and Keith walk over and start playing with Meredith's soaking wet twat. She had been neglected over the past half hour or so as she watched her sister and room mate get nailed. Being the insecure younger sister, she now felt compelled to top Erin. She said she wanted all four of us. Derek and I aren't even sure if we can get hard again but we were going to let her try. She got in front of us and alternated sucking us off and we both slowly grew. Keith got behind her and began fucking her pussy. Greg gets underneath and starts rubbing her clit. She's doing a fairy good job on me and Derek but I could tell she needed it and it was Greg and Keith's turn. I told Keith to lay down and grab some lube and told Meredith to position her in reverse cowgirl but Keith was going to ass fuck her in this position. Erin was curious so she spread some lube on her sister's butthole and spread in open. She lowered down his cock and I could tell she was hurting bit. I then had Erin and Rachael grab one of Meredith's legs and spread them wide open so Greg had plenty of room to mount her and pound her pussy. It takes them some time to get into a steady rhythm but within seconds Meredith is sobbing with pain and pleasure. Derek and I, still semi-hard, stand over Meredith's face and start to jerk off. Erin told us to grab her legs because this needed to be filmed. I had forgotten that Greg still hadn't cum so you tell he was getting close. He pulled out, Rachael grabbed his cock and jerked him off on Meredith's tits which I think she loved but she still couldn't really speak because Keith is fucking her ass hard. He was getting that look too so Erin lifted her sister up and told Keith she would finish him off and it was just in time. He stood over Meredith and blew a huge load on her tits and face. Derek and I were both hard as could be so Meredith took each of us in a hand and started to pump our cocks. It took a few minutes but within seconds of each other we shot what little we had left.
You could tell Rachael and Erin were just waiting because as soon as the drip cum was out of us they were cleaning Meredith up with their tongues.
I didn't want the night to end but I was spent. It look like all the guys were; Derek and Kieth were passed out on the floor and Greg was on the empty bed. Me and the girls fell asleep on the other bed and I was awoken at about 8AM with 3 mouths on my cock and balls. I couldn't think of a better way for my stay in Chicago to end. We showered and dressed and were on our way back by 10.
Meredith emails me fairly regularly about my trips to Chicago and keeps asking us to come back. But it turns and their parents have planned a family vacation to Jamaica and because Meredith doesn't have a spouse she is bringing Rachael!!! I hope I have another tail after that.
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