Black Tie Night in Chicago 4.7/5 (24)

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.

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