Meeting in Chicago
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June 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...
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...
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...
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,...
EroticWeekend 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...
InterracialIt 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 LoversMany 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...
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...
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...
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...
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...
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...
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 LoversCHICAGO.TXT - by Cindy V. femdom, TV, humiliation I had my first experience with a professional role play mistress this week. I was in Chicago on business, opened the weekly newspaper "The Reader" for the adult services section, and chose one of the advertisements. The price was $125 per hour or $225 for two hours, and the location was a fifteen minute cab ride from downtown, in a third floor private apartment above a retail business. A gorgeous late twenties woman named Mistress Rae met...
Ana and I were staying at that Chicago hotel for a couple days.I had a conference to attend and had invited my sweet wife to join me. Ana had been in Chicago before and she loved that windy city.On the second night during dinner at the lobby, we had met a perfect stranger and I had invited him to join us at our table.A while later, I went to the rest room and, when I came back, I found this man sitting closer to my sensual wife.I noticed his hand was below the tablecloth and I guessed he was...
It started off in a restaurant where I had gone for a drink after a long business meeting in Chicago. I had noticed her when I first walked in the door, but hadn't thought much about her until my friends had left and I was left sitting at the bar alone. I caught a glimpse of her in the mirror, and I thought that she was watching me. I turned to get a better look at her and much to my amazement, instead of cloyingly looking away, she made and held eye contact, inviting me over to her table. I...
I'm in the window seat with Mr. McKay sitting next to me. He's showing me the sales and profits of the two stores that I have been working at. He said the other investors are very impressed with me and how I've made business boom. I laughed and said I'm best on my back. The man in front of me turned around and said he'd like to see me on my back and how "good" I really am. I put my hand on his right shoulder and told him, his wife wouldn't like it if he was caught with his pants around his...
Hi. I am armaan from chicago (originally from hyderabad) doing my masters. After reading lots of stories for years on iss, its time to submit my own story. I had affairs with a couple of girls during undergrad but that’s not the story that I want to tell you guys. That’s for another day. First let me tell you about me; I am 5’10”, athletic, average build, 7” tool. After coming to us and joining the university, we had orientations where all the students would attend to get basic info about...
The plane to Chicago was, naturally, pretty full. Peter and Susan had two seats together on the outside of the wide-body jet. Susan settled next to the window and pulled out a book to read as soon as they were airborne. She wore a soft, light sweat suit with a three-quarter zip closure on the top. Peter was comfortable in chinos and a sport shirt. When the snack service began, Peter looked up from his e-reader to glance at Susan. She had pulled her zipper down to the point where the slopes...
March 15th, 1995, 6:40 EST; Mile 770; 2 miles east of Garrett, IN Oh dear god, no! George thought as he lay there, his cum all over both of them, How the hell am I going to handle this? “Jill,” he stammered, “I love you, I really do, and I want to do everything with you, like you couldn’t believe, but we can’t do this here.” “Why not?” “With the circumstances involving your minor status,” George tried to explain, “your aunt and uncle, your other uncle, your custody situation. We have to...
The divorce went well all considering. They never stopped loving each other. They never would. But Phil worked too hard creating his law firm, becoming an absentee father. And when Marisol got pregnant again either by Phil or one of her bosses, he spent even more time with her, consoling her after her abortion, her third. He stayed away from his wife and children for nearly a month. When he returned to their marital bed, unlike in his youth when he and Marisol could only see each other one...
Marisol promised Phil when he finally found her and they finally got back together in Chicago back in the mid eighties that if she ever became the reason for ending Phil's marriage, she'd leave him forever. With Missy it had been a non-issue. The love flowed equally between the three of them while the relationship lasted. But by the time she affected Phil's second marriage, she was too weak to leave. And yet she did leave. Permanently. Phil met Hannah at a cocktail party just as Marisol...
The day had started out great. It was going to continue to be a good one. Today they were going to Old Chicago. It was the world's only indoor amusement park. And it was right there in his hometown of Bolingbrook Illinois! The village was to decide between a shopping mall or the amusement park. To his delight and every other kid in town, they chose the amusement park. His parents chose Sunday because the crowds were lighter. The day was what you would expect at an amusement park. There were...
Heather spent a whole day at the spa, getting her hair done, her nails, and she feels so sexy. Her shoulder length blonde hair hangs down her back and she is very happy as she looks at her naked body in the mirror. Her bare pussy is so sexy it even turns her on. Heather is looking forward to getting fucked rough and hard and couldn't wait to feel me inside her. Heather looks at her butt in the mirror. It looks sexy too, sexy enough to give me all I can handle. She decided to get dressed and...
It’s been a long day as we both fall into our bed, the cold February wind pecking softly at the window. Earlier, hand in hand we walked silently through the neighborhood as a soft snow drifted down. It was so peaceful that our hearts and minds embraced the silence. These are the evenings that we cherish, so far from our house in L.A., but so close to the home that we learned to love in our youth. There was no wind and her hand, as always, felt so warm in mine. Although we were silent, our bond...
Melly and I had moved in together around the first of November. When Christmas came I couldn’t get time off from the fire department and Melly thought it would be better if she just went home alone. As soon as she left I was miserable. There was no joy around my tree the whole time she was gone. We talked a few times on the phone and she told everyone there about me. When she got home I wanted to tell her how crumby it had been without her but I was a little afraid of seeming too needy....
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...
Melly and I had moved in together around the first of November. When Christmascame I couldn't get time off from the fire department and Melly thoughtit would be better if she just went home alone. As soon as she left I wasmiserable. There was no joy around my tree the whole time she was gone.We talked a few times on the phone and she told everyone there about me.When she got home I wanted to tell her how crumby it had been without herbut I was a little afraid of seeming too needy. Lucky for...
LesbianMeeting Millie By Emily Ross Prologue Robbie Anderson was an ordinary kind of guy. He was a senior accountant in one of Northbury's leading accountancy practices. He enjoyed the benefits of a good salary, living in a smart part of town with his lovely wife, Helen. He drove a new BMW and every year he and Helen holidayed in exotic places like the Caribbean or the Maldives. In his early thirties, he was good looking, hard working, charming and ambitious. He expected to be offered...
Meeting at the Mall (Continued) Jim and I fell asleep and I think we fucked one more time during the night, I am not sure, but I know when I woke up the next morning, I had a ass pussy full of cum and Jim had a satisfied look on his face. Whew, it's Sunday and I need to prepare for my meeting on Monday. When Jim finally stirred, I had already showered and was dressed in only a pair of panties and bra, full makeup, and a white terrycloth robe, working on my computer. I was only in...
Main Character Deions Ha Na (JC’s wife) - 5’4” 130 lbs, olive colored skin, below shoulder length straight black hair, brown eyes, 34C breasts with small areolas, brown nipples and nearly hairless pussy. (Mid 60s) JC (Me, Ha Na’s husband) - 5’7” 200 lbs; short graying brown hair; brown eyes; 6” L 1.75” D circumcised cock and hairless. (Mid 60s) Mac - 6’ 190 lbs; short blond hair; blue eyes; muscular build; 9” L 2” D circumcised cock with a patch of blond hair above his cock. (Mid...
Meeting at Bedford MillsI had often thought about my friend Simone in the years since we had been at school together. After I graduated, I had moved to New York to pursue my career and with a husband and children, I had lost touch with Simone, but I knew that she had married a rich man whom she had met at college, and that they lived in Greenwich, Connecticut, but they had no children. I had also heard from other former classmates who had met her, that she had a glamorous lifestyle, with...
Meeting Karen By MadQuill Note: this story was inspired by another, though the plot lines are dissimilar : about a woman who models herself on someone. I hope readers will enjoy this translesbian tale. All of the characters are over eighteen years of age. This is a work may have an additional chapter. Thank you for your comments. This is a work of Fiction. Please remember this is a copyrighted work and all legal disclaimers apply. Meeting Karen - Part I I stood with...
The next day when Olivia comes into the office, she finds Mr. Wellington already there and on the telephone. She smiles and mouths a silent "Good Morning" to him and quietly slips over to her desk putting her things down. She sits there quietly as she listens to the phone call in case she is needed. Mr. Wellington is talking to a client and she learns that he will be coming to the office that afternoon. She makes a note of that – she may be needed at that meeting. Mr. Wellington finishes the...
Office SexMeeting Hannah SisyphusI hadn’t been to New York City in over twenty years, and in fact, rarely leave my off the grid cabin in Maine for any cities. I shop at a local food co-op in our small town, pick up mail at the post office, sometimes get a bowl of soup or a cup of coffee and exchange greetings with friends and neighbors then head home, happy to drive down the long dirt road through the woods and walk the path up to my quiet life.I had just completed a book of poetry and my brother told me...
Straight SexMeeting Karen Part III by MadQuill This is a four-part story is about a woman who models herself on another. I hope readers will enjoy this trans-lesbian tale. All of the characters are over eighteen years of age. This is a work may have an additional chapter. Thank you for your comments. This is a work of Fiction. Please remember this is a copyrighted work and all legal disclaimers apply. Meeting Karen - Part III Preamble : Carrie and Karen meet and ride...
Meeting Karen By MadQuill This is a four-part story is about a woman who models herself on another. I hope readers will enjoy this trans-lesbian tale. All of the characters are over eighteen years of age. This work will have additional chapters. Thank you for your comments. This is a work of Fiction. Please remember this is a copyrighted work and all legal disclaimers apply. Meeting Karen - Part II Preamble : Carrie has met Karen, and the two left the club...
This is the final part of a four-part story is about a woman who models herself on another. I hope the readers will enjoy this trans-lesbian tale. All of the characters are over eighteen years of age. Thank you for your comments. This is a work of Fiction. Please remember this is a copyrighted work and all legal disclaimers apply. ***** Meeting Karen - Part IV Preamble: Carrie's new position evolves Carrie walked to the side of the large bed and sat softly on the...
I first meet Rikki about 3 years ago, guess going on years, via the Internet. I was responding to a posting I had seen on Craigslist… not sure I understood the posting but certainly it seemed that it was a good idea. We had some great conversations via email over a variety of subjects of course many of the subjects dealt in a very sexual nature. Truth is I became more an more aroused by this woman and though we never actually had meet face to face she became an intense fantasy and arousal of my...
I first meet Rikki about 3 years ago, guess going on years, via the Internet. I was responding to a posting I had seen on Craigslist... not sure I understood the posting but certainly it seemed that it was a good idea. We had some great conversations via email over a variety of subjects of course many of the subjects dealt in a very sexual nature. Truth is I became more an more aroused by this woman and though we never actually had meet face to face she became an intense fantasy and arousal...
Meeting GloriaThis is a continuation of my story about my life with my ex-wife, Sue. Marg has come over to the west and planned to stay. She decided that I would not leave my wife for her so she had moved on and formed a permanent relationship with her good friend, Cherie. Sue, my wife had invited our babysitter to join us. It seemed that given she had promised that her cheating with men was to stop she had started to have an affair with our 18-year-old babysitter, Debbie. I had worked out from...
Wife LoversI met Mark online. I'd joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest.To begin with, I was very shy and didn't know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages.I've discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it...
Meeting Hannah Again SisyphusI hadn't seen or heard from Hannah since the last time I was in New York to do a poetry reading at the public library. That was two years ago and now I was back to do a reading at Barnes and Noble from my recently published book, Morning Songs. Hannah had been careful not to tell me where she lived or give me any information about her, so I had no way to let her know. Still I fantasized that we would meet again. I hoped she would have seen the posters advertising...
Straight SexI am not sure how or why it happened maybe because of a family tragedy, made me stop and realize life was way to short at times that you had to do things you wanted to as long as it didn’t hurt yourself or others. Or maybe it was my version of a midlife crisis. What ever it was I told my husband that I wanted to go for lunch with this older man that I had been chatting to on line. Matt and I had been chatting back and forth via emails and then MSN for a few weeks and seemed to hit...
ExhibitionismI'd joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest. To begin with, I was very shy and didn't know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages. I've discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it takes you...