Chuck Chicago Assignment IV
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My dream comes true not LA or Vegas, but ChicagoI am 20 years old now, and I guess what some would call a blonde bimbo. When I was sixteen my mom, who I am a spitting image of, took me to France, to see a special plastic surgeon, who specializes in breast enhancements. She did my moms and she now did mine. We now both have 34 DD’s, and there is no surgery line, under the breast. So anyone looking at me, can only assume these monsters, that stand proud and no sag, must be real. We have promised...
A fantasy that takes me back to the Chicago blues...and a very special dancer...Cum On Baby (Take me to Chicago 1962)Alright, I've been playing you people...I'm sorry, but that is just the way it is. I've been taking the easy way out, like the song says. I've been writing about stuff that happened in my sordid past, not taking into account that this is a fantasy site. This is a sex fantasy site, not a sex reality site, right? So, now I am going to treat it like it deserves, I am going to tell...
I sat and I thought of the words I said to Jenny those many years ago. “Yesterday is another country, I can’t go back. Tomorrow is never assured and may not happen. Today is here and we should live all dreams like it is our last chance to live them.” Words to some extent I live by. Yesterday is another country- and the borders are closed. It is an arrogance of the transient. Only that which I chose to bring with me into today comes with me. I don’t need to worry about the people who are...
The AldermanCliff Bradley was one bullet short of making the Chicago Daily News obits in the summer of 1930. He had gotten tangled up with the mob who got itchy about a bundle of misplaced cash. They wanted it back. It turned out that 10K had been stolen by a teen-age hooker who considered it a tip. Unfortunately, the Chicago outfit didn't see it that way. They terminated both their disagreement and her in the customary way, the mob's way.Lots had changed since then. Alphonse Capone was out of...
HistoricalJune 1981, Chicago, Illinois I pulled up in front of the InterContinental Hotel on North Michigan Avenue in Chicago, and reluctantly handed the keys to my Trans Am to the valet. Stephanie and I grabbed our bags, and I went to check in. I handed over my new BankAmericard, which I’d received in the mail the previous week, and after they took an imprint, they handed it back along with two-room keys. I declined the assistance of the bellman and my sister and I took the elevator up to the 12th...
This is a sex fantasy site, right? As someone in the audience commented recently, "and that, ladies and gentlemen is why this is called a fantasy site". I really don't know what he meant, I mean, that story was true...I have never really taken the liberty of fantasizing on this site...until now. I mean, really, if others can do it why not I? If other people can write stories about living out every line of some sixties song, and someone else can fantasize about making love to 'Little...
The administrative manager of Jill's employer, having been to a number of these educational conferences over the years had told her that, with the meetings running through Thursday and the closing banquet that evening, she should take the whole week. She told her husband that she would not be able to fly home until Saturday late morning, wanting to spend as much time as she could with Dave.With virtually everyone being a total stranger in this area of the country, the chances of someone...
CheatingAlright, I've been playing you people...I'm sorry, but that is just the way it is. I've been taking the easy way out, like the song says. I've been writing about stuff that happened in my sordid past, not taking into account that this is a fantasy site. This is a sex fantasy site, not a sex reality site, right? So, now I am going to treat it like it deserves, I am going to tell you nice people about one of my dearest sexual fantasies. I, Alan W. Jankowski, am going to spill my guts out on the...
InterracialLove talkin', is all very fine, yeah Jive talkin', Just isn't a crime And if there's somebody, You'll love till you die Then all that jive talkin', Just gets in your eye --Jive Talkin' (Bee Gees) I picked up the phone in the kitchen and called my mother to tell her that Kristen was taking me somewhere--a surprise--and that I'd be home before ten o'clock tomorrow evening. My mother didn't have a problem with that. Kristen drove me in her Camaro to a small airport about ten...
Dear Diary, Words can't describe it! I'm sitting at my dining room table thinking back over a weekend that is surely the high point of my life. Three days of sheer and absolute joy. Days of total expression of love. Days of sexual enjoyment and satisfaction whose tingle still rings through my body at this moment. And yet I cannot wait for the moment Charlie comes home and I can give him my body once more and feel the joy of his heat inside my body. I have just waxed this beautiful table...
His face buried in the depth of my bosom as the glistening sweat poured from his face. He looked up into my eyes and said, “You make me feel sooooo goooood.” The words expelled in breathless whispers as he finally released many months of anticipation topped by the evening’s build up. He rocked my body back and forth as he continued to release deep inside of me kissing me ever so gently on my breast and under my chin. He whispered warm and beautiful sentiments as we sat Indra style feeling...
Kendal picked me up early because we had a long drive to Chicago. I loaded my bags in her trunk and I had coffee plus cinnamon rolls for the trip. "Did Tom give you your portfolio?" she asked. "Nope, I guess we have to go to your office first." I thought for a moment of what else we might need. "Should we make a CD with all the photos watermarked?" "That's a good idea. Do you have the CDs from yesterday?" I shook my head no. I got my phone out and called Tom. He met us at his...
Chapter 1 Here I was, 33, single, and just recently transferred to Chicago. I was sent here to get this upstart IT company on its feet. We recently acquired it and they need me to make sure it got up and running, our way, and to make a profit. And now 3 years later, I’m loving my life. I’m Blake, and as I said, I am 33, single, 6’, 190 lbs, with short blond hair. I generally work out at least 3 times a week, so I am in good shape. I’ve been told I am good looking, and judging from...
I open the garage door and feel the bitter chill of the Denver morning breeze. Moving around the car I hit the trunk release on the remote and place a small suitcase inside. As I back out of the driveway, the clock signals to me it is 4 AM. I turn onto 120th going east heading to the airport for my 6 AM flight out to Chicago. As I drive into the darkness all I can think about is tonight is the night. The night I will meet Michael for the very first time. Pulling into the airport garage,...
August 1982, Chicago, Illinois The drive between Milford and Chicago was becoming almost automatic for me — I’d stop the same places, eat the same thing, and fill up with gas at the same Amoco station. I made my usual good time and pulled up in front of the apartment building just before 6:00pm Chicago time. I got my mail from the mailbox, opened the apartment, then carried all my stuff in from the car. I moved the car from the loading zone to a parking spot, then walked to Theo’s. I...
The wait finally ended, Phil felt peculiarly unrushed. As they say, he'd waited over two and a half years, what's a few hours? Sitting in his old red VW beetle, probably on its last legs after the long journey from Cambridge to Chicago, he watched for the motherfucker Marisol married to leave the house. Arriving in Chicago late in the evening, he had slept at his fellow Harvard graduate's parents house. Despite the dark cloud of lost love and the unresolved discord with his parents, by...
Dear Diary, He did not quite get me there tonight, and so I am awake at 3AM. However, I am not a bit sad about that, he made me tingle all over and delighted me in ways I never expected to see again. He was just darling. Besides, I'm still just a little bit tender down there from our wonderful overindulgence in sex in Chicago. So I might have regretted him going on much longer. Delightful. We may be acting a bit like teenagers just at the moment, but I am sure things will settle down to...
Katherine Jackson arrived just before the presentation was to begin. Fred had called her during the week and excitedly explained how he was being recognized for his investment strategies and was going to be a guest speaker at the conference that he was attending in Chicago. Mrs. Jackson was thrilled by her husband’s accomplishments. She knew this could help him in his career and when he asked for her to fly out and support him; she couldn’t say no plus it meant a night together away from the...
My hard breathing hissed through my clenched teeth as I arched my back and tightened every muscle I could find to keep from releasing a flood of cum into the ultra-petite Japanese school girl’s pussy on top of me. As my muscles flinched with quick pulses, I knew it was too late to hold back. I looked up at the sweet young face with full, tender lips as I pulled down hard with a hand on each of her curvaceous hips. With my cock buried so deep I could feel the top of her canal, I shot my hot,...
EroticThe HeiressThe well dressed woman sat across the desk from Detective Cliff Bradley. "I could use a name," Cliff said."I don't know his name," the voluptuous woman curtly replied. "I mean yours, not the blackmailer.""I'd rather not say until you've heard my story.""Okay, I'm all ears.""Well Mr. Bradley," she began."It's Cliff, doll.""Yes, Cliff, she continued. "I met a man.""Excuse me. I think I've heard this one before. It's about a handsome guy that you fell in love with who stole your virtue....
HistoricalWeekend in Chicago! My delicious secret!Not too long ago, one of my sexy friends asked me if I had a sexual experience that stood out in my mind; one that I’ve never really told anyone. Well…the answer to that is yes! I do, it’s been my little delicious secret for quite a while. Today, I am finally going to share it.My stepdaughter, Jessie – who is a real cutie – played on the tennis team in college. She told me about all the players on the team but the conversation kept coming back to her...
Pakistani Couple Swinging in Chicago I was rather lucky to get admission in Chicago University for PhD studies. I was relatively young 35 years and was not expecting to go to USA for 4 to 5 years and do my PhD. My name is Sameer, I am a Pakistani married to my girlfriend and class fellow in Masters program Saima. Saima belonged to a middleclass family and as you would know that in Pakistan having love marriage is a sin, therefore we faced problem from both the families. One reason for me to...
LETTER FROM CHICAGODear Shoeblossom:My name’s Noelle. I was just reading ?LETTER FROM BOSTON??That dopey rich boy Franz the Fool wrote you about how I was his Candy Striper, when he was in the hospital in four cast traction?and how I teased his cock and balls, and beat the crap out of him?and made him suck off my gay cousin! God, it brings it all back!Truth be told, I was only on the Candy Striper volunteer bit because I had to do three hundred hours of volunteer work as punishment for selling...
It would soon be our eleventh anniversary and my wife, Jenny, and I were looking forward to celebrating it on that upcoming Saturday. Being partners in business and being constantly on the road together can really put a strain on a relationship and I could feel us drifting apart lately. It was my idea to come back Chicago for our anniversary; I prayed it would put some spark back into our marriage. The plan was to return to the same club where I had proposed to her. I had checked first to make...
588,750.62 Japanese Yen. That’s how much my $5,000 dollars came out to after conversion. Here I was in the Hotel Nikko in Chicago waiting in my suite for my special visitor from Japan. I figured if a girl was willing to pose for nude photos for money then maybe, just maybe, she’d do more for money. So, I started my quest. It took many phone calls to a variety of publishers until I found someone who could get an offer to the lovely young japanese model Ayumi Tahara. I made my offer: all expenses...
InterracialThe Assignment By RogerGirl Melvin and Ambrose were at their makeup stations goofing off as usual. The assignment for the class was to give the girls in the chairs glamour makeovers, but the two guys had no interest in the assignment. While they were both very talented makeup artists and could very easily complete the assignment, they had only taken the course for the movie makeup portion. They had both completed their other assignments with great enthusiasm, impressing their...
Somewhere, within the storm, there was a sign. It wasn’t much. It could be, and frequently was, easily missed. Unadorned, made of faded bronze…just another plaque stuck to the side of a deteriorating brick building, tilting a little bit to the left in its old age. The curious and careful reader would find Olde English lettering, scratchy and unpainted, informing that the bar at the bottom of the stairs was called ‘The Rage.’ Not many people can claim to be curious and careful reader,...
As the sun was coming over Lake Michigan, I glanced over at this handsome man lying next to me in my bed. I had not slept a wink at all during the night. I had come to bed about 10:30 and had tossed & turned all night long. I wanted to sleep so badly but it looked like it wasn’t going to happen, not tonight anyway. Well I could hear him breathing in a deep rhythmic tone. You may be asking yourself, why is she talking like he is somebody new? Well, maybe that is because he is. Well, new to me...
It was my third night there at Chicago, now completing my quick business trip. During the second night I had been fucked by a hungry black man, Tyrone, who I had met at the lobby’s bar while I enjoyed a drink.After ruining my cunt so badly, Tyrone had called his friends Theo and Donny. These two black well hung guys had taken turns to fuck me even harder. Tyrone had fucked me in the ass while I was riding one of his buddies.I passed out during the night and I woke alone in early morning.I found...
I was boarding a plane to fly to Chicago; when I got a nice surprise.I heard my name and, as I turned my head back; I saw this beauty woman Donna, who was married to one of my old Bosses…She greeted me with a kiss on my cheek and asked if I was going also to Chicago. I could not believe this sexy lady would fly with me.Donna was a real trophy wife; a beauty redhead in her late forties, with nice round tits and a couple long legs to die for. She looked hot, wearing a tight dark green dress and...
Sex on the train, sex in the hotel, sex, sex, sex. I recently got an invitation to speak at a conference in Chicago. Joan as usual came with me. Joan is the most desirable woman and has the most voracious sexual appetite of any woman I have ever met. We have shared many sexual adventures and have enjoyed them all. Recently we were in Savannah and barely avoided a gangbang, although Joan might have enjoyed it. I love Joan more than life itself. I made the travel arrangements. We would take a...
Wife LoversJill rolled over and as she awoke she was disappointed to find that she was the only occupant of the bed; she had gotten accustomed to, and relished the touch of her lover. She arose and took her beautiful naked self out to the living room to find Dave also without a stitch of clothing, standing at the massive windows sipping on a cup of coffee and just taking in the view of Chicago's lakefront. Jill quietly approached him from the rear and embraced him from the back pressing her sexy breasts...
CheatingMany years ago, I was driving from Denver to Chicago, cruising down the highway late on a Friday afternoon. I had to stop for gas. As I was filling up, this young guy approached me. He was a good-looking k**, in his early 20’s. "You going far?" he asked. "To Chicago," I replied."I'd like to go there, can you give me a lift? I can help with gas money," he answered.I thought about it. The company would be nice. I opened the trunk and told the k** to throw in his pack and jump in the front...
It was late and I was exhausted and could wait to get home to sleep. So I waited for the train to come, which seemed forever. There was no one in sight, which is strange for Chicago. I was almost sleep when the train finally came. It was a full eight cars and I sat anywhere. The train was pleasant and comfortable. I had far to go, so I relaxed. On the next stop, there entering the train was a woman. A sweet and beautiful very, very dark skin Black girl. She was wearing blue shorts that went up...
What a week! I had spent the whole week pampering myself, going to the spa, shopping for new clothes and getting ready for a weekend getaway to Chicago. My husband had been gone all week on business and we were going to meet for our first weekend away as empty nesters. I had spent the last 18 years living the soccer mom life, so I was particularly excited to resume living for me. Our daughter had started college this fall, so we planned on completely enjoying this new phase of our lives. I was...
I'm waiting at Penn Station a little after 3.30 pm with a 19 hour train journey ahead of me. I am thankful for my expenses card that allowed me to purchase a roomliner bedroom all for myself so at least I can have some privacy, and some time to rest after my long week in New York. I'm wearing an old pair of slightly worn jeans, a nicely fitting polo shirt, a tatty leather bag is at my feet containing all my stuff for my summer in the States. With nothing else to do, I scan the platform mild...
Straight SexI spent last weekend with Marla in Chicago so she could catch up with some old friends. When we got there Friday night and Michael opened the door to his apartment, I could feel my cock start to get thick and harden up just looking at his handsom face and tall slender body. Once inside he offered to fix us some drinks while we made ourselfs at home. Marla and Michael were getting caught up since the last time they were together and every now and then I caught Michael trying to sneak a peek...
I was rather lucky to get admission at Chicago University for Ph.D. studies. I was relatively young 35 years and was not expecting to go to the USA for 4 to 5 years and do my Ph.D. My name is Sameer. I am a Pakistani married to my girlfriend and class fellow in Masters program Saima. Saima belonged to a middle-class family and as you would know that in Pakistan having a love marriage is a sin. Therefore we faced problems from both the families. One of the reasons for me to apply for Ph.D. was...
Chicago By Suzi (Johnson) Thomas I was in Chicago, but I really didn't want to be there. My company was a sponsor of an investment seminar that was being given as a fund raising event for the university that our chairman had attended, and as my boss had explained to me, the company had to send representatives to "show the flag." As though a $50,000 contribution weren't enough, the chairman had decided that two portfolio managers had to show up as well. I was selected to...
Guys these is Andrew (Name Changed) again and thanks everyone for all your responses for my last story. I have been reading ISS since last 5 years and have been great fan since then. Thanks to everyone for writing such a sexy stories and making this site a big hit. All girls and ladies anywhere in USA or India of any age and size as I respect all of them please send me an email on if you like my story and if you want to have pleasure. All things between us will be confidential and trust me you...
Hello Everyone. My name is Ankit (name changed). I am from Mumbai but currently I live in Chicago – USA and I am a big fan of ISS. This is my story with Pankhuri (name changed) when I was doing my Masters in University of Illinois at Chicago. I have always been interested in sexy and tall girls. About myself I am athletic, well built, smart and handsome. About Pankhuri – she is tall and has a figure of 34-28-36. We met first time during our Orientation. We were in our first year of MS and...
I’ve been sharing my horny wife Kathy for several years now and have a great sex life. Late last summer Kathy and I decided to go to Chicago for a few days to do some shopping and enjoy the city. Kathy had never been to Chicago and I’d told her about the great downtown area. On the third night there we decided to go out to a nice restaurant and then go to a Jazz club later in the evening. Kathy got ready for the evening and slipped on the little black dress she brought and a pair of...
Hi everyone! My name is Jill. All my stories are true and are about the fun that i have when i get away from my hometown so that i can explore my inner whore without the locals finding out about it. Here, i'm going to tell you about the weekend of November 19-21, 2010. If you want to find out more about me or be my friend, then please go to my xhamster personal page.Late Friday after work i took a flight to Chicago. My plan was to go to some sex clubs and strip clubs to see what kind of...
Welcome to ChicagoBy Alice Parker ?Are you sure that is the one?? Colette asked me, her brow was furled adding emphasis to the concern in her voice and eyes. ?Yeah, I'm sure.? I said as I studied him from across the bar. ?Really? What about that one?? she asked turning her head, indicating a man who's very shiny loafers were the first thing that caught my eye. His manicured fingers were the next thing I noticed. ?Nope.? I said smoothly. ?Why...
December 28th, 1984, Chicago, Illinois Traffic was light until we got very close to Chicago, but even then, there was no real delay. I pulled up in front of my house at about 7:45am and the four of us got out and went inside. Jennifer and I used the bathroom, and she changed into a skirt and blouse, and we were back in Stephanie’s Nova by 8:00am. Forty-five minutes later, the two of us were sitting in the lobby at Nuvatec waiting for Scott Bannerman. He came out five minutes later. “Steve,...
Every six months, Marisol flew to New York to visit her son bearing presents and abundance of love. Early summer she came for his birthday and every Christmas she joined Luisa's family for the celebration. The presents didn't hurt, but Nate loved his "aunt's" visits more for her presence. She seemed devoted to his every word. She shared little of her life, telling him his "mother" had all the luck and she was just a mousy old maid. "But you're not," he said on Christmas of his...
Mistress Sarah led me back into her bedroom and sat naked in a chair in front of a large dressing table. She ordered me to fetch my maid's dress. It was time for me to learn how to properly dress her for a night out and she wanted me in full sissy attire for the event. Mistress Sarah watched me step into my sissy dress. She told me to turn around slowly for her as she pulled down on the pink silky fabric, ensuring the shiny dress cascaded around my legs smoothly and wrinkle free. She then...
CrossdressingNote – When I wrote the story, my aim was to make it as realistic as possible and that is the reason why I ended up making it so long. But all the stuff really builds up to this story making it more erotic. Please read it until the end, you’ll enjoy it a lot. (Stuff starts to happen after half the story, so don’t stop midway) My email is – if you want to drop any suggestions. This story happened 2 years ago when I was in South Dakota doing my Masters in Science. I was a keen student back when...
IncestMy first trip was to BH1 (which is now closed) because it was the closest to my home and the least expensive to enter. I only had the vision of what I read or saw in movies so I was nervous and excited at the same time. It was kind of strange from the outside, just a small sign and when entering this large old building I had to go downstairs. I paid my entry fee and received a room key and a smallish well used, but clean, towel, the door buzzed and I entered. It had dim lighting so it took...
Author’s note – be forewarned – not only is this non erotic, it is also very, very politcal. Hopefully it may make you think about the consequences of what some are wishing for. Chicago 2035 ‘Did you hear?’ it was whispered to me as I entered the office building on that dreary Tuesday morning. Even as I was removing my smog mask someone else came buy and asked, ‘Did you hear the news?’ I nodded politely and said nothing more as I folded up my acid rain poncho and stuffed it into its sack,...
My name is Kyle Eliott. My friends call me “strummer” because I have been known to strum a mean guitar. More about that later but for now these pages will tell the story of my sex life over the last 2 years. Believe me when I tell you, ever since my divorce two years ago, it has been a wild wild ride. I married young (20) and we stayed together for 19 years. One night she said she had enough and left me for another WOMAN!!! Imagine that!!! That moment I turned my life around. I started working...
Over the next year I came to know Leah pretty well. Single, she had moved away from home in hopes of starting a new life in Chicago. I was incredibly attracted to her, but alas I couldn’t act on this lust as I was a happily married man. And despite this fact, Leah seemed to make it a point to flirt with me. She was always willing to share a story and a laugh or two with me. She was truly a delightfully sexy young woman. Then one afternoon she said something to me that caused me to...
Andee tossed her purse onto the hotel bed and dropped her suitcase onto the rack tucked away in the closet. She had one last stop – this time Chicago – before heading back home. She hadn’t really had the chance to discuss everything that occurred in Denver with her husband, other than to allude how a certain fantasy of hers had become a reality. Of course, there is only so much fun and excitement to be had via webcamming with someone halfway across the continent, even less so when you long for...
You and I have had the most incredible online friendship I can ever imagine. With miles between us, it is quite apparent we will never meet. Much to my surprise, one day you e-mailed me that you are coming to Chicago to some convention in July. We both were very excited about you being 90 minutes away and the possibility of meeting. The date finally arrives. You arrive first in the morning and get settled in your hotel before attending meetings that afternoon. We meet at the restaurant in your...
This past summer I took a trip to Chicago with a few girlfriends. It was fun and I enjoyed it. The whole reason we went on the trup was so I could get my mind off of things for a few days. I had been feeling down after a resent break-up and wasnt really acting like myself. So thats when we decided to take a trip. After finally getting there, we checked into the hotel and got settled in our room. I was exhausted from driving so I took a nap while the two other girls, Caitlin and Amber, left to...
I lived in Chicago for most of my life starting the year after college. It was the late 1980's and I was a struggling, underpaid and overworked, twenty-something single bisexual woman, but I always found a way to have fun. Lots of bars and night clubs, lots of dancing and lots of dates. I had a few steady boyfriends and girlfriends and always a constantly changing group of friends with benefits. I was exploring the limits of my sexuality and was constantly finding that my limits were easily...
She's married; she has a number of young children at home; she has a successful career; she is intelligent and beautiful, and she has a libido running on overdrive. Why would she risk it all? Why would she risk it all with him? So much to lose and what would she gain? That fucking sex drive will be the death of her. He is older, like at least twenty five years older, with limited sexual capabilities; he's married; he should be thinking of other things like retirement or downsizing his house or...
CheatingAndee tossed her purse onto the hotel bed and dropped her suitcase onto the rack tucked away in the closet. She had one last stop – this time Chicago – before heading back home. She hadn’t really had the chance to discuss everything that occurred in Denver with her husband, other than to allude how a certain fantasy of hers had become a reality. Of course, there is only so much fun and excitement to be had via webcamming with someone halfway across the continent; even less so when you long for...
Wife Lovers