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Travel to Chicago

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WARNING This little story deals with a topic some might find offensive. If you don't care for taboo topics you might want to skip this one. Otherwise enjoy it. The places in this story are all real. The story is something that really happened.

While we were talking one evening I mentioned I had to go back to Chicago to attend to some family business and wanted you to accompany me. I told you that I want to leave Friday two weeks from now. I said we'd return the following Wednesday, so make sure you tell your boss you need the time off.

We arrive at O'Hare Friday afternoon, and after a cab ride to the Drake Hotel downtown, we check in and just relax. That evening we catch a cab and go to Geja's for dinner and drinks. After a relaxed, romantic dinner we catch a cab up to Kingston Mines and for the next four hours we listen to Mississippi blues. We are both enjoying the music, the scene and the drinks. 1AM turns into two and around three we are both getting tired and ready to call it a night.

Awaking late the next morning I remind you that I'm meeting some of my family today, so you'll have to keep yourself busy. "You'll find plenty to do in the city to keep you busy. I want you to stop at one of the Gold Coast stores and find yourself a little black dress and heels to wear tonight. I've also arranged for you to go to spa down the street for a massage, facial, and whatever else might pop into your mind. I'll give you a call a little later and let you know what's happen". With that I kiss you bye and walk out of the room.

You lounge in bed for a while having room service bring you some breakfast before rushing out to explore the area. You go from store to store looking for the perfect black dress - something that accentuates your figure and exposes just enough of your breasts to invite stares. You've decided that you need some new panties and a bra to wear with it, so you stop at the Victoria Secret store in the area. Looking at your watch you realize that you have to head over to MySpa to get your massage you'll leave finding your shoes for afterward. When you get to the spa you realize I set everything up - there is nothing you need to decide. I've arranged for a full body massage, facial, pedicure and manicure, ...the whole works!

It's getting late in the day and you are finally done with the spa treatments, and talking to the attendant you find the location of an excellent shoe store, some place that will have the heels to match your dress. You find the perfect pair - Italian evening shoes with 4 inch stiletto heels. You feel ready for this evening - relaxed and pampered. Starting back to the hotel your phone rings, and noticing it was from me, you answer it. After some pleasantries I tell you that I can't make it back to the hotel before we are going out so you should meet me at a little place on Division Street. "Hop a cab over there about 6, go in order a drink, and I'll be right there."

As the cab pulled up to the club the taxi driver said "Are you certain this is where you want to be? This isn't a very safe place to be." You assure him it is the correct place, and paying him, you get out of the cab and walk into the club. Inside, you let your eyes adjust and scan the room for me. You do notice the rather seedy collection of guys in the club though. You are somewhat apprehensive and uneasy, but you know that I wouldn't put you in harm's way. So you walk over to the bar and ask the bartender for a glass of wine. You figure I'm just running a little late and I'll be there shortly, so you sip your wine slowly, trying to avoid staring at the guys around the area. You found an empty booth by the pool table, and sitting there you are trying to ignore everyone around you.

Four guys are playing pool, and as you slide into the booth you know they are staring at you. Your little black dress shows off a little of your cleavage, but not too much. The bottom half of the dress hugs your ass and thighs making it a little difficult to walk. But you bought it knowing what I like. One of the guys asks says: "Would you care to join us?" You politely decline mentioning that you are waiting for your date.

Sitting there and being stared at constantly made you feel like they are violating you - stripping off your clothes in their mind. Whenever you did glance at them, they would lick their lips. After they had a few more drinks, it got worse. They would stand between the pool table and you, rubbing their crotches, as they waited for their turn to shoot. Their remarks to each other kept getting more and more crude as though you weren't even sitting there. Finally one of them blurted out: "How about spreading those legs so we have a real hole to aim at?" "Do you fuck as good as you look?" said another of the players. With that comment you decide to wait for me outside, and as you begin to slide out of the booth one of the guys came over and placing his hand on your shoulder pushes you back in to the booth, saying loud enough for everyone to hear "Bet you a blow job I make my next shot."

You sat there amazed and in disbelief. Because you didn't say anything he reached under your dress, rubbing your thighs and trying to part your legs. You resisted, hoping someone would come to your aid. "Hey, dude it's your shot." Getting up, he stepped out of the booth and as he did one of the other guys slid in next to you. You hear "You owe me a blow job! I made my shot."

Suddenly the bartender ran to the front door and locked it. Two of the guys got hold of you and pulled you out of the booth, kicking and screaming. You begged the guys to let you leave, and you repeated it again and again."You can have all the money I have! Take it and I promise not to tell anyone." The guy that wanted the blow job, pulled down his zipper and laughing said: "We don't give a shit about your money. You can keep that. We aren't going to let you keep that cunt to yourself!" You realize you are going to be gang r*ped, and could either fight it and possibly get hurt or just relax. Suddenly all ten of the guys appeared around you.

Someone pushed you down, the bartender standing before you holding your head and keeping your still. The man who made the bet stepped closer, pulled out his cock and told you to start sucking it. He said "If you bite me I'll knock your teeth out, so just enjoy it bitch!" You resisted for a while until one of the guys held your nose causing you to open your mouth. And when you did he forced his cock into your mouth. The bartender started to pull your mouth back and forth pretending to be a cunt. "Not bad! Warm and juicy! She needs more practice giving head though."

"Maybe she's never sucked cock before. How about it? You ever have a cock fuck your throat before? Sure she has. Notice how her lips squeeze around your dick", the bartender said leaning over your shoulder to look at you. The guy fucking your mouth pushed the bartender away and grabbed your head and began to violently fuck your face. Everyone could hear your forehead slapping up against the belly of the guy and her your grunts every time he pushed his cock deep into your throat. When he cummed in your mouth, his cum was bubbling from the corners of your mouth and ran from your nose. As he continued to fuck your mouth, cum dribbled down your neck and spilled on the front of your black dress. As he pulled out, you fought for air and coughed up more of his cum that was lodged deep into your throat.

Two of the guys held you in place as everyone else got undressed, and these same two guys carried you to the pool table, putting you spread eagle on the table. There were four guys holding you down, one on each hand and one on each leg. You were struggling but you couldn't escape. But since your dress was so tight they couldn't pull your legs too wide apart. The bartender reached over grabbed your dress at the helm and cut it open to your waist! The guys were gawking at what your were wearing: sheer black nylon stockings with lace tops, held up with a black satin garter belt. You were wearing a pair of sheer black panties that did nothing but display your sexy pussy behind the transparent material. You were wearing a sheer black half bra that emphasized your nipples, something the guys could see through the fabric of your dress."Damn! Your dressed like this and you have to be forced to suck cock? Maybe you just don't like us. Is that it? You waiting for Chance? You dressed like this so Chance would fuck you? Well, cunt you won;t be able to fuck him or anybody else for a while when we're done. Now let's see just how tight your cunt is!" Suddenly you realize these guys must know me and I arranged this." The guys ripped off your dress, panties and bra.

Suddenly out of the back, I enter the room. "Hey, guys we are going to give her one of her fantasies. She wants to be held down, spread eagle, fisted until she squirts and keep stimulating her until she can't stand it any longer. She's a squirter too! After I'm done with her she's all yours. Just give her what she wants - a cunt filled with cum and orgasm after orgasm."

Slowly I push my fingers into your cunt. One finger, two, three, four. I beginning to spread the lips of your cunt wider apart, slowly my hand goes deeper and deeper in you, until just my thumb is sticking out. And I being to work it in, little by little stretching your cunt until my hand to my wrist is in your cunt. Suddenly I'm using my arm like a giant cock - fucking your deep and hard, listening to you moaning with each stroke. "Would one of you guys massage her clit, while I fist her? How about some of you other guys suck her tits or give her a cock to suck! I can attest to how great a cock sucker she is!" And soon you are being played with like never before when I suddenly slide my fingers up your ass as well!

You are starting to moan louder and louder. I can tell you are enjoying this because you are starting to buck your hips with every thrust I make with my arm. Guys are sucking your tits, playing with your clit and forcing a very large cock down your throat. Suddenly you thrust your hips up, begin squirting and gurgle. It is having an effect on you since you're no longer moving. Pulling my fingers from your ass I hand one of the guys some smelling salts and tell him to crack it open and wave it under your nose to wake you up. As he does so, you start to shake your head and awaken from your orgasm. As you do you still feel my arm into your cunt, fucking you and mouths on your tits. You mumble something like "Oh my God..."...and we continue for another long while.

And as I promised when I was done I let all the guys, who are still hard and stroking their cocks, time to fuck and cum in you!

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