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Black Tie Night in Chicago

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It had been awhile since Sheri and I were out of town together without the kids. We were in Chicago on a business trip where we were attending a black tie fundraiser. Although we knew very few people who were going Sheri was looking forward to getting all dressed up. We had gotten to Chicago very late the night before and we pretty well checked into the hotel and called it a night as I had an early morning meeting the next day. I woke up early and tried not to wake Sheri as I dressed and got ready to leave. I left Sheri a few hundred dollars on the pillow with a note to not spend the money on shoes but for something nice for me to unwrap later tonight.

I got back to the hotel about an hour before we had to be at the black tie event. Sheri was soaking in the tub when I got in. She greeted me by standing up in her bubble bath and showing me her shaved pussy. I gave her a kiss and stroked her wet slippery pussy but as we were running late, that is where it had ended. I asked Sheri what she had purchased today and she said se would show it to me later. And with that she got dressed in the bathroom while dressed in the main bedroom.

Sheri came out of the bathroom and looked terrific. She had on a black dress that accented her big tits and she wore some high heels that looked new. I asked is that what you bought, motioning to the heels. She said yes and I also got a little something else to wear with them, but you will see that later.

We went to the black tie event and it was, as usual, pretty boring. But we were able to catch a buzz. At around 11:00 pm my clients announced they were leaving as they had a long trip back to the burbs. Sheri and I stayed at the table with another out of town guest that seemed attached to no one from our group in particular. As it turned out he was from Denver and was frequently in Chicago on business. With the clients now gone Sheri and I started to pick up the pace drinking and our new friend Kent joined in. Sheri coaxed me onto the dance floor for a few slow songs. I asked her when do I get to see what she was wearing underneath her dress and she responded that she expected to be taken for a good time since we were out of town before I got anything special.

We ended back at the table chatting with Kent. The topic turned to TV and Sheri brought up that her favourite new show was Swingtown but that she wished it were on HBO versus standard network. Kent mentioned that he had seen the show and the fact that it filmed in Chicago. Sheri responded it was too bad the Playboy club was now closed. At which Kent said he knew of a place that he had been to before and he was going to go there tonight but his date never showed for the black tie. And the club did not let single men in. At this point I kidded that I would go but I doubt Sheri would be up for it. Feeling no pain from her drinks Sheri said she would certainly like to go as long as she did not have to do anything.

We went outside and hopped in a limo outside that Kent had on call. We got in and had a few more drinks before arriving at the “Pomme Rouge”. I had noticed in the limo that Kent was certainly staring at Sheri’s big tits, and when Kent was giving directions to the driver I mentioned it to Sheri. Sheri responded that she also though he had been looking up her dress as he sat on the other side of the limo. I responded if it was I I would too.

When we arrived Kent briefly spoke with the doorman to let him know we were all together and we entered. The club was very full in the main bar area and there were several small booths on the outer edge of the bar that were pretty secluded. The doorman that Kent had spoken with directed us to a booth. It was obvious that Kent was a bit of a regular here. When Sheri commented that it looked like he knew what he was doing here, he grinned and said he had been around Chicago many times on business and he had found this place as result of a date he had. After a few rounds of drinks we noticed nothing too sexual was going on in the bar and mentioned same to Kent. He said the real action was in some back rooms. He said there were viewing rooms that you could go and see what was happening in the backrooms. I asked Sheri if she wanted to see what was in the backrooms and she jumped up and said to Kent to lead the way.

Kent took us through a VIP area and up around to a back viewing room. He said you really never know what you get as you enter these many viewing rooms and we may have to look into a few to see what was up. We went in to the first room and it was dark and took a while for our eyes to be come accustomed. When they did Kent pushed a button that allowed for a window shade to open up. In the room we were watching there was two girls going 69 while their dates watched and jerked off. After awhile one of the girls grabbed a vibrator and started working it into the others snatch. Sheri brushed her hand against my crotch and commented, “well I guess you are liking what you see but I would like a little something for me”.

So Kent punched the shutter button closing the slide and moved to another wall and pushed another shutter button. This shutter opened up and we could see two guys and a girl who had just entered the room. The guys were young and in good shape and the girl was trim with a pretty small set of tits. I joked that I think we should go back to the other window. Sheri said no this seems to have more entertainment value. We watched as the girl slid down into a crouch as the guys pulled out their hard cocks. The girl quickly started jerking them off into her mouth. Sheri reached back and rubbed my cock and said I see you are still hard. I rebutted she seemed to know what she was doing down there. After getting the guys hard the girl was bent over so one guy could fuck her while she sucked on the other. Sheri commented that this is shit that always bugs me when we watch porn, two guys and no foreplay.

Kent chuckled at this and asked Sheri if she had ever had a threesome before. She said no that she wasn’t into girls and two cocks seemed like too much work. While the girl was getting fucked, Sheri was pushing her ass back into my growing cock, and every once in awhile she would slip her hand behind her back to rub it. We watched the threesome assume a variety of positions before the guys filled her with their cum. We decided to go back to our booth for one more drink. Sheri excused herself to use the bathroom as we went and sat down.

Kent commented that we had a very cool relationship and that many couples he doubted would be willing to come here. I agreed. Kent added do you think your wife would be interested in going into a room. I chuckled and said she likes to watch but not so much being watched.

We went back to the limo and got in. Kent took a little bit of time to get back to the limo. I asked Sheri if she had fun. And she said she did but she may have ruined her surprise for me upon which she produced from her purse a set of panties. She added I got a little wet in there and now these are just too wet to wear. I slid my hand down and felt her shaved pussy and it was very wet. I rubbed her clit but when the door opened for Kent to get in she pushed my hand away.

Kent entered the limo and said he hoped he wasn’t disturbing us. Sheri was a little embarrassed so I said no we were just making plans for later. We poured ourselves some more drinks and headed back to the hotel. I noticed that Kent kept stealing glances at Sheri’s tits and her crotch. In the darkness Sheri was slowly stroking my cock through my tux pants. I didn’t think in this light he could see anything but as went through a well-lit tunnel he seemed to be staring directly between Sheri’s legs. I imagine he got a bit of an eyeful as Sheri’s dress had slid up her legs and her hand was on my cock. Sheri backed off during the tunnel but as soon as it was dark she started rubbing my cock again.

Kent said in the darkness, “Sheri you seem a little different from the earlier ride”. Sheri confided that she was a bit drunker. Kent chuckled, “I meant I swear you had panties on earlier”. I almost spit out my drink and laughed. Sheri was only a touch embarrassed and a little too emboldened by the Cosmo binge she had been on. So she responded, “they had gotten a little damp while watching the girl get fucked by those guys”, and added “did you like what you saw”. Kent said he only caught a glimpse but he did like what he saw. Sheri said, “well I guess since you have seen mine I should at least get a glimpse of yours”. Kent looked at me and I shrugged. So Kent unzipped his tux pants and slid his semi hard cock out. It was quite a bit bigger than mine. Sheri said, “You have got quite the sword there, does it get much bigger?” Kent said, “well why don’t you continue doing what you were doing in the dark and we would see”. So with this Sheri started stroking my cock. I leaned over and started kissing her and rubbing her tits through the dress. Sheri looked over my shoulder and saw Kent jerking off to the sight of us. His cock had grown to a pretty impressive size. Sheri unzipped my pants and freed my cock and started to stroke it to its full length. She went down and started kissing the tip. She kept stealing glances at Kent’s massive pole.

It was about that time that the Limo driver announced that we had arrived at the hotel. Kent asked Sheri if she would like to come upstairs for a nightcap. Sheri said she was game.

So we went up to Kent’s suite. When we were in the elevator Sheri whispered into my ear that I might just get a fantasy checked off tonight. We got into Kent’s suite and he went to full bar and fixed us drinks. Sheri took a sip and said I hope you guys do a better job at foreplay than the two guys in the bar. At this point Sheri pulled me close and unzipped my pants and again pulled out my cock. As she was rubbing my cock we joined in a deep kiss. I had Sheri spin around so I could unzip her dress. She let the straps fall and she slowly let it drop to the floor. She stepped out of her dress and was naked except for her high heals, and her new stockings, garters and a new bra that was so sheer you could see Sheri’s nipples through it. After Kent got a good eyeful I spun her around and started to kiss her while rubbing her shaved pussy. She was so wet I felt her moan and her legs buckle a tiny bit. She was still stroking my cock that was poking out the fly of my pants. Kent and I were still dressed in our tuxes at this point. Sheri saw Kent start towards his zipper and she said come here and I will give you a hand with that. Sheri turned to face Kent and let my cock go. As she unzipped Kent’s pants and reached in and pulled out his hard massive cock, I slid my hands around her to caress her tits and kiss her neck. I slid her bra strap off one shoulder and then the other and undid the back clasp. Sheri let the bra fall off one tit and then the other and grabbed my hands and pulled them up over top. I kissed her neck while Kent slid his hands down Sheri’s side and onto her hips. With two cocks out Sheri started to crouch down. She said to me, “I noticed you liked it when the girl at the club did this so I figured I would do it too”. She went down to her knees and slowly started to suck on my swollen cock. All the while she was stroking Kent’s cock to its full length. She alternated and started sucking his cock. After only a few minutes she suggested that it was her turn.

So we sat her in the middle of the couch with one of us on ether side. While I kissed her and fondled a breast Kent took a pink nipple in his mouth and sucked it hard. I had slid my hand down to her pussy and started to rub her swollen clit. Kent then moved his hand down and started fingering her dripping pussy. Sheri moaned uncontrollably. She still had a hand on each of our cocks and was stroking them simultaneously. Kent then slid off the couch and kissed his way down her body and down her legs. Sheri shifted a little to her side and put one of her legs on the arm of the couch fully exposing her shaved pussy to Kent. She was locked in a hard kiss with me when Kent first licked her clit. I could feel her tongue pause as she felt the tongue of another man lap her swollen clit and lips. She was enjoying the ravishing that she was getting as I held her firmly and kissed her. Sheri then shifted me a little further down the couch so she could suck my cock and watch Kent lick her pussy. I could tell by the intermittent pauses in her cock sucking that she was enjoying the pussy licking. I felt as if I was going to come from the terrific blowjob and the site of another man eating my wife’s pussy so I suggested we switch it up.

Kent rose off of the floor and moved to the head of the couch. I positioned Sheri on her back so she could lean on her side and take Kent in her mouth while I resumed the pussy licking. I slid down between her legs as I watch Sheri pump Kent’s cock a few times before licking the tip. Sheri noticed I was staring up and looked directly into my eyes as she licked Kent’s cock from the base to the tip. She vigorously pumped it while licking it. I was mesmerized by the show. Sheri took her hand and placed it on the back of my head and pushed me down on to her pussy. I licked her wet pussy and got a finger wet and started to rub around her ass hole. I could hear from the slurping that Kent’s big cock was now buried in my wife’s skilful mouth. I slowly inserted a finger into my wife’s ass that was wet from her pussy juice. I felt her relax so she could take it all the way.

Kent was starting to moan and Sheri stopped and said, unless you can get hard again don’t even think of cumming until this cock has been in my pussy. I was quite shocked at the dirty talk but I guess Sheri didn’t want to miss out on having the largest cock of her life in her.

Kent suggested maybe we would need to switch this around. We got up and took the rest of our tuxes off. Kent sat on the couch and Sheri started to climb up on his big rod. I got closer so I could see this thick cock spread my wife’s lips. Sheri paused over top of his cock and rubbed his head around her wet pussy. She then slowly inserted it and started to gobble the cock with her pussy. I stood up on the couch next to them so Sheri could suck my cock. Sheri slowly started to pick up the pace on the big cock, while Kent buried his face in Sheri soft boobs. Sheri reached over and pulled me close and wrapped her hand between my legs and pulled my ass forward. She was sucking ferociously on my cock.

I asked her how it was feeling and she moaned and took me even deeper. I pulled out of her mouth and had her turn around so she could fuck Kent reverse cowgirl. She spun around and Kent had her by the hips and was bouncing her up on his cock. I stood in front of her and kissed her and rubbed her sweat-covered tits. I then reached down and started to rub her clit as Kent’s cock ploughed into her. She was moaning and cried that she was going to come. With that she started to gush around Kent’s cock.

I had still yet to enter that hot pussy so I suggested to Sheri that she get up on all fours so I could take her doggy style. She suggested we move to the bed. Kent climbed up to the head of the bed while Sheri climbed onto the bed on all fours. I rubbed her ass and inserted a finger into her pussy making sure to stay away from her overly sensitive clit. I slowly eased the head of my cock past her lips and into her well-lubed box. Kent had repositioned himself so Sheri could suck on him while I fucked her. I slowly picked up rhythm while Sheri worked over the hard cock in front of her. Sheri’s tits were swaying like pendulums while I rocked in and out of her. I pulled the head of my cock from her pussy and rubbed it over her ass. I then slid my cock into her wet ass. She stiffened at first then relaxed and took my hard cock in her tight ass. Sheri stopped sucking on Kent and asked if I wanted to DP her. I said it was up to her. She said as long as Kent doesn’t mind being in her pussy she would give it a try. Kent said he would be pleased to being that hot box again so Sheri shifted up and mounted Kent’s hard cock. Sheri then bent all the way over so I could slide my hard cock back into her tight ass. I slid in slowly. Sheri moaned and we started to slowly move in unison. Sheri was sliding down on Kent’s cock then backing up on mine. I asked how she felt and she replied, “full”. We continued to ride Sheri in rhythm. I told Sheri I was going to cum soon and she suggested a finishing position.

She rolled on her side so I could fuck her ass and reaches around and play with her clit, while she sucked Kent’s cock. Sheri was picking up the pace on Kent’s cock and I knew he would not last much longer. She reached up and cupped his balls and squeezed them while she had his monster cock as far down her throat as she could. Kent let out a moan and Sheri pulled him from her mouth and he squirted his load all over her tits.

I was also getting close to cumming but wanted to get Sheri off one more time. I was talking in her ear telling her how fucking horny my slutty wife was making me and how I was going to fill her ass with my cum. I told her to show me where she wanted my hand and she slid it into her pussy. Kent moved down to rub her clit so I moved my hand back and grabbed her hips and started fucking her while Kent was rubbing her clit and fingering her pussy. Sheri was holding her breath and getting close to cumming so I pushed deep inside her tight ass and let my cock spurt into her. Sheri started to squeeze her legs together and trembled and came on Kent’s hand. I rolled back and pulled my cock from her ass. Sheri rolled on to her stomach and kissed me.

Kent excused himself and said he had to take a shower as he had an early flight out. I asked Sheri if she wanted to go shower with him and she said she would have to pass as she had to catch her breath and calm down. Kent dressed and told us not to rush as we could catch some sleep before we went back to or room. Kent grabbed his bags and left. On the way out he left his business card on the desk and said if we wanted to we should call him if we were in Denver.

I rolled over and kissed Sheri and asked if she had gotten enough attention. She smiled and said she might be sore for a day or two but it was worth it. I agreed. We got up to take a nice hot shower where I soaped up my wife’s beautiful body and washed her. She lathered up her hands and started to stroke my cock and said let’s see if we can make you come once more too. She lathered up my cock while rubbing my balls and soaping my asshole. In no time my hard cock let a small jet of cum into the lather and we were done. We went back to the bed and cuddled and fell off to sleep.

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