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Weekend in Chicago

5229 words | 1 |4.00

This naughty tale started when we were invited to a family member’s wedding in Chicago. Jeff and I decided to make it a mini vacation and have some fun. When away we like to really let loose and embrace our lifestyle enjoying our freedom since there is minimal probability of running into anyone we might know.

The wedding ceremony was a private ceremony at the estate of the groom’s parents. It was a magnificent estate and the grounds were decorated beautifully. It was a beautiful sunny winter day; quite unusual for Chicago at this time of year. I wore a long black dress with a plunging neckline and had a slit almost up to my hip on the left leg. I wore black heels and black thigh highs. Underneath was a garter belt with no panties. Every step I took in that dress exposed the lace tops of my stockings through the slit. I accented my ensemble with a simple string of pearls. Jeff was decked out in a beautiful black and gray suit. We looked so good together. The ceremony was beautiful but with four hours to kill before the scheduled start of the country club reception and with the country club just a few miles away from the hotel, Jeff and I decided to go back to the hotel and relax with a couple of cocktails. As we walked into the hotel lounge, the only other patrons was a group of seven black men sitting in a group of leather sofas and chairs watching a football game on the big screen television. The men very tall and fit and were obvious athletes of some kind. They had money as well since they were dressed in expensive suits and presented themselves very professionally.

As we walked into the bar the seven men looked away from the television and watched as I walked to the two leather chairs that were just a few feet away from them. The men turned to each other and whispered among themselves. I knew they were talking about me and I have to confess I always love the attention I get from men admiring my body in the most lascivious manner. I quietly volunteered to Jeff that I would get our drinks. Knowing he was married to a wanton slut, he knew why I offered to get them. The main and only reason was to have the guys watch me some more. As I approached the bar I made sure my gate was as enticing as possible as I went by them. Success! They almost appeared like teenage boys, practically drooling as I came near them. I could feel their eyes undressing me as I passed by returning to my seat with our beverages. As I sat in my seat I made sure to expose my stocking clad leg as I crossed my leg for maximum exposure through my slit. I then made eye contact with one of the men. Smiling at him I asked who they were cheering for in the game. They told me they were Packers fans. Now I do not know much about football, but I knew I was going to be a fan of the other team. I smiled at him and jokingly expressed my condolences. He had a look of confusion on his face as he asked me why condolences. “Because the Packers will have another loss by the end of the day,” I offered. That opened up a dialogue between myself and the men. We teased each other until one of the men asked me how confident I was that the Packers will lose?

He then asked if I wanted to back my prediction with a wager. I said sure, what would you suggest for stakes? How about the loser buys the winner a drink? I chuckled chiding him about being a big time spender. I countered that I thought I could handle that, but I was pretty sure that I would be quite thirsty by the end of the game.

Jeff and I moved and joined the group in their area ordering another drink each.

As we talked they learned why Jeff and I were in town. We found it ironic as they revealed that they were in town because Terrance, one of their guys, was getting married and they all got together for a bachelor weekend before he went down the aisle. Looking at them I jokingly said, “Wait a minute, he is getting married, and your here watching a football game? Shouldn’t you have gotten him a hooker?” They informed me that they did have one set up but she never showed. I chuckled and told them well I guess no one takes pride in their job anymore. That brought up a roar of laughter from everyone. We were having a good time and I was giving some good ribbing as Chicago was up 17-0 at halftime. But I didn’t let up and continued to tease the guys. I told them I was so confident the Packers were going to lose that I would up the bet to drinks and dinner if they were not too scared. Since I challenged their manhood, they really had no choice but accept the new bet. The second half started and Chicago was now up 20-0 and I teased them mercilessly. Jeff chimed in as well saying how much we were going to enjoy eating on their dime.

In the third quarter though, things started to change, as the Packers started to score. Soon it was late in the fourth quarter 20-17 and although Chicago was still winning, the Packers were controlling the game. My pride wouldn’t allow me to back down now and I continued to tease the boys. I kept telling them there was not enough time and it is over, so just give up. Then Chicago threw an interception! I could have crawled under the table at that point.

The guys were cheering and laughing. Suddenly Davante,who had been the most vocal all day, looked over at both Jeff and I and asked, “How confident are you now that Chicago will be winning? Want to up the bet?” I couldn’t back down now, so I told him there isn’t enough time so yes, what do you have in mind? He looked at Jeff and told him, “Well, we still need some entertainment for our bachelor party. If The Packers win, you agree to be our slut and take the place of the hooker who stood us up.” That shut me up! I was shocked and looked at Jeff. I could see it did interest him. Jeff then asked, “What do we get if Chicago holds on to win?” Devante told Jeff they would pay us the $2000 they agreed on for the hooker to ride around on the limo bus and service them all regardless. If we win we get the money and we could walk. If they win they still pay, but I was their slut for the night till dawn.

Jeff sat back for a second or two before he looked at Devante and countered, “Well if you’re that confident, if the Packers win she will be your whore but make it five thousand dollars.

The guys huddled up and talked for a few minutes; then they turned to us and simply said, “DEAL! But that means she does everything and anything we want for as all night.

Jeff looked over at me I was speechless and motionless for a long awkward moment before nodding. Jeff told Devante he could agree on those terms but had one more condition. He told Devante he had to be present to secure my safety. Everyone agreed to those terms. It wasn’t a minute later the Packers threw for a long touchdown to go ahead for the first time in the game.

I sank back into my seat and just looked over at Jeff who too was speechless, but also had a look of excitement on his face. I knew he didn’t mind losing this bet, as he loved watching me fuck other men. He was really getting his rocks off with me having a gangbang! I sat motionless as I watched the teams on the screen shaking hands and listening to the announcers saying how they couldn’t believe how the Packers engineered this comeback. As I listened, I watched as all the guys left the room only to return a few minutes later. Devante turned to Mike and handed him a stack of money. “Here is 2500, you get the rest tomorrow.

Jeff looked to me.

“Hey….a bet is a bet and we were serious of these conditions.” Devante said firmly. “Your wife is our whore now.”

Jeff looked over at me and replied, “We take our bets seriously and live up to our word, we have all intentions to living up to the conditions of the bet.” And then turning to me saying, “Don’t we Wendy ?” I nodded.

With that all seven guys stood up, Devante held his hand out to me and smiled.

Devante, who by now I realized it was the best man, got on his cell phone And re-contacted the party bus limo service that they had earlier cancelled. He was able to rebook the bus but it wouldn’t be to the hotel for another couple of hours.

I sighed with relief and asked Jeff if he would get me another drink.

Devonte’ waved Jeff off said “ I’ll buy the drink and then we are going upstairs.”

He returned shortly with the Moscow Mule that I had ordered and it went down faster than I intended.

“Well, should we move this party to our suite?” Jeff said.

Without saying a word I took Devante’s hand and followed him and the other six men along with my husband Jeff to the elevator. The nine of us loaded into the elevator, as the door closed I felt one of the men behind me caress my ass, as we road up to the top floor.

As the elevator door opened we all walked into a beautiful penthouse suite. Devante took my hand and walked me to the center of the room as the other men sat around me. Devante left me there and he sat back in one of the lounge chairs.

Devante turned to Jeff and said, “I think it only proper that you unwrap this package and deliver the naked slut you owe us for our whore. Show us the goods!” Jeff stood behind me and slowly lowered the zipper on the back of my dress. He then pushed the material off of my shoulders and the dress floated to the floor. I stepped out of the last barrier to any shred of modesty that I may have previously grasped hold to; I actually loved exhibiting my sexy body to this group that I knew would soon be pounding their cocks into my willing body.

There I stood in full display for all the guys to lust after. The guys all roared as my tits and pussy were in plan view, for all of them to see. I then watched Jeff walk across the room to take a seat at the bar about twenty feet away. He smiled as he watched me surrounded by a group of black men, knowing that the slut in me was about to be unleashed. As I stared into Jeff’s eyes, I stood there naked except for my heels, thigh highs, garter and pearl necklace. The hoops and lewd remarks from the boys got louder and louder as I then did a pirouette so they could all fully appreciate my naked body, now delivered for their use, in payment of the high stakes bet. I heard one of the guys yell out, “Damn, look at that hot pussy I can’t wait to have some of that!” Devante spoke up, “Wait a minute guys, our guest of honor gets first crack. Show our groom a good time slut and show us all what you have.”

I remarked back to Devante, “My pleasure.” I walked over to Terrance, the groom, and immediately spread my stocking clad legs so I could grind my already moist cunt on his thigh, as I reached up placing my hand on the back of his neck and pulled him down to me to give him a most salacious kiss.

As our kiss continued, I ran my hand from the back of his neck down over his massive chest. In the meantime, my other hand was busy rubbing the substantial bulge in his slacks. When our kiss broke I again reached up to bring his face down to be smothered between my tits, as I ground harder onto his thigh that he now had wedged between my legs.

When I pulled away, to let him breath, I slid to the floor and knelt between his legs. Undoing his belt and pants, I lowered his zipper and reached in to take hold of his growing cock. As I stroked him under his boxers I looked back at the rest of the guys who have been watching intently. I smiled and yelled out, “Oh my! Some bride is going to be real happy with this.” The room erupted in laughter as they watched as I lowered his boxers and pants exposing his big thick black cock. “Now let me show you how much white woman love these big thick black cocks.” Lowering my head and wrapping my lips around his cock, I took him into my mouth. My tongue swirled around the thick mushroom cap at the end of this monster cock. As I worked my mouth on Terrance’s big black cock I could hear the others scuffling around and moving closer. As my mouth moved faster up and down Terrance’s dick, I could see the rest of the guys move closer around me and I could see that by now they were all naked. I knew when I was done sucking Terrance off I was going to get fucked over and over again. That thought spurred me on to suck Terrance even faster. The rest of the guys were making all kinds of off color comments, about how I was sucking Terrance’s cock as I started to feel different hands all over my body. One hand rubbed between my legs, “Damn, she is soaking wet,” he yelled out. This whore is ready to go someone said, with that I felt Terrance’s dick twitch and throb as the first stream of his hot cum filled my mouth. Terrance moaned and everyone knew he was feeding me his cum.

I no sooner sucked the last droplet of cum from Terrance’s dick I was guided over to the sofa as I knelt on it facing out the back. I watched as Devante moved behind me and suddenly felt a hand grip my waist. Then I felt the tip of his hard cock press against my soaking wet cunt. He tightened his grip on my hips as he pressed into me hard and deep making me gasp as he drove that long black torpedo deep into my white married cunt from behind. “Oh yes what an amazing pussy she has he yelled out.” The room erupted in cheers as they all commented on how much of a dirty slut I was and how I needed to be fucked by their big black cocks. They were all correct in what they were saying; I did need it and needed it badly. As Devante fucked me hard and deep a guy, Bobby, moved behind the couch and placed his cock at my mouth, “Suck it Bitch!” He commanded. I opened my mouth as he shoved it deep into my mouth. Bobby fucked my mouth as Devante fucked my hot cunt. I looked across the room and I could see my husband Jeff watching and smiling from ear to ear as he sipped his cocktail, while watching me being used by these big black cocks.

As Devante was getting closer to releasing his first load of cum, I could hear his moans become louder and his thrust more aggressive. As he thrust hard into me he drove my mouth harder onto Bobby’s cock making me gag some. Then with one hard thrust and a loud scream, Devante emptied his hot load into my quivering pussy. Knowing Devante was filling my cunt with his cum drove me over the edge as my body started to shake as I erupted into an amazing orgasm. Still not completely recovered from my orgasm, Terrance sat next to me on the sofa. Looking over, I could see his cock raging hard once again. Terrance then announced “I need to feel that white cunt on my black cock now!” as he guided me to sit on it facing him. I straddled his lap and lowered my hot juicy cunt onto his big thick cock. With Devante having already filled me with a huge load of hot cum, I was so lubed up that Terrance’s thick tool easily slid deep into my cunt. Bobby moved to the side of the couch, inserting his dick to my mouth once again.

I started to suck him more as Jerry, another of the party,moved behind me with a tube of lube in his hand. After a few moments of sucking and fucking on Terrence’s lap, I could feel a new cock against my ass. The lubed cock slowly entered into me and started fucking my ass as Terrance fucked my pussy and Bobby fucked my mouth. These men must have played some kind of team sport, basketball I heard later, as they synchronized perfectly with each thrusting their cocks in and out of all my holes in perfect rhythm and coordinated rotation. Devante looking over to Jeff across the room yelling out, “Damn she is a dirty slut who just loves her cocks isn’t she?”

Jeff replied back “She loves as much as she can get as often as she can get them, especially black cocks.”

They both looked back at me as the three guys fucked me hard and deep fucking all three holes. Bobby suddenly grunted like a wild animal as he pumped his hot cum into my mouth. I sucked that big black cock like it was a life line and swallowed every last drop of the spunk he spewed down my throat! The other two were still fucking my ass and cunt as the fifth guy, Scott, stepped in front of me and placed his cock at my lips. He spit out his order, “Suck this one now bitch.” I immediately opened my mouth and he thrust his cock deep inside without any hesitation. Jerry continued fucking my ass and Terrance rammed into my wanton wet cunt harder and faster from underneath me, holding my waist tightly in his strong grip.

I started moaning uncontrollably as another orgasm ripped thru my body in waves that were exploding up from the two cocks thrusting in and out of both my pussy and ass. I began to feel Terrance’ body tense under me, as his hot meat began to throb causing my orgasm to drag on seemingly without end as he was shooting another beautiful load of cum inside of me filling me like a two bit whore with his hot sperm. Hearing Terrance unload into me, drove Jerry over the edge and he filled my ass with his hot cum. Just minutes later Scott screamed out as he filled my mouth with yet another big load to swallow.

I got a very brief break to slam down another Moscow mule drink as Andre and Theo hovered close to me. stroking two big thick rick hard cocks.

Theo grabbed me by the hips and pulled me off the couch Turning me around and bending me over standing. Theo roughly fucking me doggy style as I balanced legs spread wide on my slutty heals.

Andre Tangled his large hands into my dark brown curly hair and held my head still placing his second big hand on the back of my neck as he fed me his cock.

Jeff was now stroking his cock his eyes locked on the scene as Andre held my head still and fucked my mouth occasionally causing me to gag a little and drool.

The feeling of of Theo squeezing both of my hips tight as him mercilessly rammed his fat cock in and out of me, while knowing what a slut I was allowing everyone to use me in a way that only Jeff should caused me to rush over the edge a third time and I almost blacked out from the intensity of the orgasms as my knees buckled.

I was vaguely aware of feeling Theos huge cock swell even larger, as he filled me with another flood of hot semen. Almost simultaneously I was swallowing a huge load of come again. I was unable to swallow at all and some of it ran down my pretty face and dripped off my chin and a long visceral string. As I collapsed over the back of the couch I looked up at Jeff and watched as he was stroking his nice white cock. I smiled at him knowing he was enjoying watching his slut, now also a paid for whore.

He took my glance as an invite and came over laying me in the couch and sinking his rather large white cock into my destroyed sloppy pussy.

Pushing my legs back to where my knees were by my ears and the flats of my feet were up in the air He fucked me as well as any had so far whispering naughty things in my ears pushing buttons that only he knew.

I could feel him swell up and he timed it so that just as I was coming again he let go inside of me to the cheers of the many black men in the room watching.

“Damn he can fuck for a white boy” Devante said.

“But that’s enough white boy this is our pussy go back to the bar.”

All of the guys laughed.

Some of the guys were drinking and some of the guys were stroking their cocks which were getting hard again.

I started to brace myself for another round when Devonte’ cell pinged a tone indicating a text message.

“The bus is here “he said. And all the guys started to put their clothes on again and a flurry of activity.

I started to get dressed as well when Terrence spoke up.

“Oh no, you don’t need your clothes back on whore.”

He pulled a men’s suit jacket out of the closet. It was long for me as a coat but barely covering my ass as a button down dress.

You expect me to wear this through the lobby I stated.

“Yes and we’re leaving right now “replied Devante.

I smiled and said “ With my hair a mess my makeup smeared and come on my face and running down the insides of both of my legs?”

Devante said “you’re a whore, so stop worrying about looking like whore.“ “All of those people in the lobby are going to see you getting out of the elevator with a group of black men wearing one mans suit jackets as a dress, walking in Slutty heels, looking like you’ve been fucked hard, and know just what kind of slut you are”

I shrugged and started moving.

We all left the penthouse and got on the elevator again to take it down to the bus which was parked in the circle in front of the hotel.

On the elevator Jerry couldn’t resist reaching around grabbing my waist with one arm and pulling to the back of the car. There he spread my legs a little with his knee from behind before plunging two of his thick fingers into my sloppy wet pussy.

He curled his fingers up and back towards my belly button and started to finger fuck me hitting the spot up underneath my pubic bone.

My already over stimulated G spot began to you react almost immediately as the elevator doors closed.

The elevator stopped twice on the way down so that a white older businessman and a young asian man in workout clothing could squeeze on to the now full car.

Jerry continued to finger fuck me hard as Booby slipped his hand up under the jacket and fondled my breasts while kissing me on the neck. I turned to him and thrust my tongue into his mouth stifling a moan into his mouth. Our activities were mostly screened from the two new occupants by the bodies in front of us. I had to fight to remain quiet As my eyes rolled back in my head and my knees buckled again.

Despite my efforts a couple of whimpers and a moan escaped my tortured lips causing both of the new occupants to look back in concern at the two men groping me. The rest of the guys laughed out loud And made lewd comments.

The doors to the elevator opened in the lobby which was now full of people spilling out from the bar and some nearby banquet rooms.

I got numerous sideways glances and shocked looks as I made my way across the hotel lobby and out the door with the group of black men continuing with their lewd comments and loud references to me as whore.

On the drive to the strip bar Scott and Devonte’ sat on either side of me as I took turns sucking on both of their cocks, Devonte’s hand the back of my head encouraging me.

Before either could come we arrived at the night club and all of the men eagerly piled off the bus.

Devonte’ turned and said “don’t go anywhere slut I’m sure the boys will be back on the bus to fuck you some more.”

I took advantage of this break and had Jeff make me another stiff drink as I took a painkiller and messed with my hair and make up. After an hour and a half Terrence stumble back on to the bus smelling a little like booze.

He made his way over to me on the bus zipped his pants down and pushed on my shoulders. I obediently got on my knees. He just looked down a me with a slightly annoyed look as I paused looking up. So I removed his hard black cock out of his boxers and went to work desperately hoping that I could satisfy him orally to give my tired sore pussy a break.

I was rewarded after a short period of time with a groan and another load of come to swallow.

Terrence zipped his pants up turned away from me and went back into the club without saying a word.

I had another visit from Scott who worked my tired pussy over again, And a visit from both Devonte’ and Theo Who took turns on me switching between my pussy and mouth. They all returned to the club as soon as I satisfied my role as a cum receptacle.

I must have dozed off a bit when the guys were all piling back on to the bus. I was checking my watch when Theo stumbled over to me and told me to get on all fours on the bus floor.

His words were slurred and all of the guys were laughing again.

On the drive back to the hotel he fucked me in the ass as i was coached by most of the guys to keep my ass as high as I could in the air both to make it convenient for fucking and so that it provided the best view.

As I was ass fucked all the way back, Jeff and Devonte both jacked off and took turns pulling my head up off the floor so they could cum on my face. Devonte had me stick my tongue out as well.

The lobby was thankfully empty except for a snickering Bellman as we made our way back up to the suite at approximately 4 AM.

I was feeling pretty woozy by now as the s drinks were catching up with me. I could remember being thrown onto the bed off of someone shoulder before drifting off into unconsciousness.

I drifted in and out of sleep as I was vaguely aware of one cock after another in me. By the next day I laid collapsed on the bed with cum oozing out of both my cunt and my asshole, both of which were fucked more times than I could possibly even estimate.

At some point Jeff was shaking me awake and daylight was pouring through the blinds in the mostly dark room.

As I drowsily came back to consciousness, I looked down my body and realized that the boys had also bukkaked me, covering my tits, face, tummy and my well used pussy with cum apparently after I had passed out. Their deposits had dried like a coating of plaster on my body. Laying all over me was large bills, some of them stuck to my body. The remaining $2500 owed for my ass I later counted. I stepped into the bathroom for a minimal quick clean up before slipping back into my dress and heels for the short journey down the hallway to our suite.

Jeff gathered up the cash and before we left their suite, Jeff and I exchanged phone numbers with Devante just in case we got back to Chicago or Devante came our way.

Jeff and I then left and went back to our room where he couldn’t stop telling me how hot it was to watch me get gang banged by those black guys. With his cock rock hard I sucked him for a while before he slipped his dick into my cum filled cunt And gently fucked me.

My pussy hurt at first from being so swollen and sore but slowly the pain receded and again I felt the impending waves of orgasm rising and washing over me.

Needless to say we never did make the wedding reception,we called and told them we had a minor accident and got tied up. I am sure they would be stunned if they only knew the only thing wrecked was me and it was really because I was a black cock whore for a groom and his wedding party.

We can invite the folks that we really feel we missed to the baby shower. It turns out my thoughts that my fertile years were past were inaccurate.

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1 Comment

  • Reply Tom ID:1i2kovirk0c7

    Sounds like my wife
    We wanted to go away for our 7th anniversary
    We went out to the pool my wife in a bikini that barely covered her. There were 4 guys there.
    We chatted on and off with them.

    My wife said she needed more lotion on her back. I smiled at the guys and I put lotion up and down her legs and on her back.then I motion two guys over to rub it in.

    She felt 4 hands on her and looked back at me smiling. The guy on her legs was trying to finger her and the other was rubbing her side boob.

    After a bit she said needed lotion on her front
    But not at pool. We told them our motel room found out they were next to us.

    We get to our room and she meet them at door naked. She said ok guys give me your lotion.
    One guy got between her legs and started fucking her. He came in her then the other 3 guys took their turn.

    I thing we didn’t think about is why we took our trip. We wanted to start our family.
    Well we did she was pregnant from weekend