Rendezvous In Chicago - Chapter 4 free porn video

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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 knowing or thinking that Dave was not her husband were remote at best. And because they both wore wedding rings, from all outward appearances, it would seem they were married; well, they were, just not to each other.

Dave had rented a tuxedo for the event, which was delivered to the suite late that morning. He tried it on and it fit perfectly. Jill had purchased a beautiful full length gown for the event. Her husband thought she had purchased the gown for his industry conference's closing banquet, held a couple of weeks prior; little did he realize the plans Jill had for this elegant dress. Her plan for this event in Chicago was her primary focus when making her selection.

Now with Thursday afternoon free, Jill returned to the suite and Dave suggested that they spend some casual time exploring the city and just enjoying each other's company as well as some of the local flavor of the lake front area. “How about we start with lunch at the Billy Goat Tavern?”

“The what?”

“It's a local eatery made famous in years gone by John Belushi and Dan Aykroyd on the old Saturday Night Live. You remember, someone would order 'a burger, fries and a Coke?' And the response was always, 'You have cheeez-buger, cheeeeps and a Pepsi.' The place was actually made famous in the early 20th century for the curse the owner placed on the Chicago Cubs who have not won a World Series since.”

“But why the goat?”

“The owner used to bring the goat with him to the games,” chuckling his remark.

“Are you serious?”

“Yeah. I guess it was a little different in those days.”

“Yeah I guess. So, that sounds like fun. We can maybe get a little better feel for the locals in a place like that.”

“It will be fun. But don't order the goat! They are very protective of the goat.”

“Oh, I can imagine,” she laughed.

So off the lovers ventured strolling hand in hand up Michigan Avenue, across the Chicago River and down the steps on the north side to find it still there; the Billy Goat Tavern. The place was a buzz of activity with it being just after noon. They wedged their way through the crowd and found a table not too far from the counter.

Ever the prankster, Jill ordered, “Just a hamburger, fries and a Coke, please.”

The waiter responded, “No, you have cheeez-buger, cheeeeps and Pepsi, okay?”

Laughing, Jill agreed, “Cheeez-buger, cheeeeps and Pepsi it will be then.”

Damn, he loved her playfulness and that beautiful smile! They were so relaxed with each other and so in sync with their moods, emotions and sense of humor. Dave wondered how difficult it would be to let this dream of a woman really leave on Saturday. In his heart he knew and quickly recovered to his normal positive frame of mind, vowing to himself to thoroughly enjoy the next forty-eight hours with this angel of his dreams.

After finishing perhaps a third of their meal the love birds agreed that they had had enough and wanted to get on with their enjoyment of the city. Dave led Jill out of the restaurant and to the nearest place where they could catch a water taxi that ran up the Chicago River and out to Navy Pier. In recent years they had developed quite an attractive amusement park on the pier, where families and lovers enjoyed being near the Lake.

As they walked along Dave couldn't help but notice, even in casual clothes, just how taken he was with Jill. She wore a striped pullover that had a V neckline with a nice display of cleavage, but not in a slutty way, just a hint at what lies beneath. She also had short jean shorts that her top almost covered while not tucked in. On her feet she had cute leather thongs that matched her purse and complimented her leather bracelet and dangling disks earrings. She was casually attired but in such a classy manner.

With Dave in beige cargo shorts, a golf shirt and deck shoes, they made a most attractive couple.

The water taxi was a fun diversion from the normal transport around the city and just being on the water with the wind and sun in their face felt great, as it blew Jill's pony tail about. Jill looked healthy and alive with the relaxed excitement of the day and the anticipation of just spending unhurried time with her lover.

Navy Pier has all the normal food vendors and other amusement attractions so normal for this type of venue. However, a couple of things make it unique. On the far east end of the pier is a huge ballroom that is utilized for various events. The Steve Harvey Show, based in Chicago, recently hosted speed dating with a couple of hundred couples. It has also been the site of a number of political gatherings, business meetings, fashion shows, etc.

Near the west end of the pier is a Ferris wheel standing one hundred and fifty feet tall. There have been many a romantic couple take advantage of this unique method of seeing the city from a taller perspective on this very slow moving ride. The seating is fairly secluded. When Jill and Dave took their turn, as the wheel stopped and started with each new customer taking their seat, about half way up Dave leaned over and took Jill in his embrace and kissed her in a most salacious way. As their arousal grew, he couldn't help but venture under her loose top, cupping and kneading her ample bosom. He then dropped his hand down to her lap and began loosening her shorts.

Jill broke their kiss and protested her embarrassment, “We can't do that here …” But her resolve was anything but firm, as she smiled her million dollar smile.

“ Why not? No one can see. And you'll have something to tell your grand kids; how grandma was brought to orgasm on top of the Ferris wheel at Navy Pier in Chicago,” he smiled that charming successful salesman smile of his.

He then knew his victory when Jill said, “Are you sure no one will see us?”

Sealing his sweet victory, Dave moved his hand into her dislodged shorts and into her panties to find her engorged clit and steamy center. He teased all around her little nub as her head swam with thoughts of just how crazy this was, but oh so pleasurable. She knew this sweet man would never do anything to cause her embarrassment and gave into her own lustful desires thrusting her hips forward to meet his invading fingers as they began to plundge into her clammy center with more and more resolve. As the slow moving Ferris wheel reached the zenith of its course, Jill also went over the edge and her orgasm peaked, with its powerful wave of pleasure crashing from her center through her entire body. This was just so delicious!

The Ferris Wheel had completed its three revolution ride and began the process of changing occupants of each car, with its once again start and stop motion. The lovers were only about two thirds of the way back up to the top of their last revolution. Dave continued his attack on her sweet pussy, bringing Jill to her third and most powerful orgasm. With her head pulled back and her upper torso arched in mind blowing rapture, she begged him, “Please honey, please … we have to stop …” Oh, but she was so enjoying the ride.

So he relented allowing her to straighten and put her clothing back in proper order. But just as they approached their normal point of disembarkation, Dave held up a fifty dollar bill to show the operator of the ride and indicated he wanted to continue to ride. The operator understood and conveniently skipped their car in the exchange of passengers. Ah yes, Chicago, “the city that works” with the proper payoff.

Jill looked at Dave with a scowl but couldn't begin to hold back her brilliant smile, as his hand once again made its return visit into her lace panties. Jill did not hold back this time and relished his naughty attentiveness. Giving in to her own lustful emotions, she lost track of the number of releases that coursed through her body; some small and a few all encompassing, but all so very wonderful!

As they finally left the ride, Dave slipped the Franklin into the operator's large calloused hand. Jill could not bring herself to look at the man, as she realized she was flushed with the heat glowing off her pretty face and a hint of the scent of this woman wafted into the air. They walked away, hand in hand with their fingers intertwined, giggling like high school kids. What a wonderful memory the lovers had created that leisurely afternoon; one they would each play over and over again in their minds with fond memories throughout the remainder of their lives.

They strolled as lovers do along the lake front totally enjoying each other's company and eventually found their way back to the hotel. As they entered the lobby on their way to the bank of elevators, Jill was sure she heard a woman behind her complain to her husband, “Look at that couple! It is so obvious the love and affection they have for each other. Why don't you treat me like that anymore?”

Once back in the suite, they kicked off their shoes and relaxed in quiet conversation, with the occasional show of affection, quite a bit of humor and plenty of sexual overtones in their friendly banter.

“Hey Jill, would you like me to try my hand at making you one of your favorite Martinis? I paid close attention to William the other day, building on my basic knowledge of the drink. I think I can come pretty close, if you would like me to try.”

“That would be fabulous. And you will join me?”

“I will, but if you don't mind, I'll just stick with my normal scotch and water.”

So he mixed them each one of their favorite cocktails and they continued their relaxing visit for the next hour or so. They both so totally loved chatting with each other online, and it continued with an ease in person, that neither was accustomed to, as conversation with their respective spouses had become difficult at best and often was reduced to standoffish disagreements. This was so different; so much fun. They actually enjoyed each other's company, just visiting, almost as much as their illicit affair … well, almost.

Dave then noticing the pace of their conversation slowing, suggested that they perhaps rest for a short while before their big evening. Jill agreed that this would be a wonderful idea, as neither of them ever got to slow down and just enjoy such an extravagance in real life.

As they went into the bedroom, Dave began to help Jill out of her clothes. She looked at him with a little bit of confusion. Dave said, “It will be more comfortable like this.” He really didn't have to convince her and soon their unclothed forms were cuddling together in a loving embrace. Jill slipped into a comfortable sleep first. Dave tenderly drew circles all around her eyes and lips with his finger tips. He lovingly gazed upon this beautiful woman, just drinking in how angelic she looked in her restful slumber. He then drifted off into an enjoyable dream of his conspiratorial partner.

And damn what a dream he was having! It was so hot; so erotic … when suddenly he opened his eyes, trying to recognize where he was, and there before his eyes, was the luscious head of rich auburn hair bobbing up and down. He then realized that his dream had morphed into reality. There was his goddess, his mistress slathering his cock from its bulbous head down to the root and back up again. Her tongue licking all around the head. Jill locked eyes with her lover and then with that lusty look in her eyes, took his entire length into her mouth and down her throat without even a hint of gagging.

Dave's eyes rolled back in their sockets. He had never experienced such pleasure. Jill loved giving head. She thoroughly enjoyed taking a soft cock in her mouth and feeling it harden as she gave her lover pleasure. In her college years, mostly as a cheap form of birth control, she learned to be quite talented at deep-throating and was able to take most guys without any gag reflex coming into play.

Dave wasn't awake too long before the ministrations Jill was giving had his manhood throbbing and he knew he was almost to the point of no return. Jill knew it also and soon he was coating the back of her throat with his ejaculate. She worked to not waste a drop, as she swallowed every drop. She then brought her body up Dave's, teasing his skin with the pointed tips of her awesome breasts. She nuzzled into his neck and whispered, “Hey big boy; did you enjoy your wake up call?”

“Holy shit Jill! That was so fucking hot. Thank you darling,” as they cuddled their naked bodies together so pleasurably. They were so comfortable with each other, as if they had been lovers for years, not days.

“What time is it anyway?” he inquired.

“ About six, but we have an hour before we need to be downstairs for cocktails. I just hate to end this. I love being in your protective embrace. This truly is a dream come true.”

“You think this is? I was actually dreaming about you doing that to me and awoke to it really happening. My lord Jill, what a wonderful expression of your love; your giving. I guess when we chatted online, you couldn't really properly explain just how talented you are.”

“Lover believe me, the pleasure was all mine. I totally love giving oral, which is in this case not just a matter of sexual pleasure. Dave I hope you realize that it was truly an expression of my love for you; so much better than just a lust filled act of sexual relief. I find my lover gets so much more pleasure, as do I, if I have truly heart felt feelings for him.”

“You mean you have performed oral sex for a guy and not felt love?”

“Dave you know, a girl has to relieve her own needs. So, as ashamed as I am to admit it, yes Dave. In my college days, I loved giving blow jobs and it wasn't until much later that I experienced the added pleasure that comes from any sex act, when I have truly loved the man.”

“Yeah, I guess when we were kids we did a number of things we might not be so proud to admit, if we are truthful about it. I never should have been surprised Jill. It is so enjoyable to hear you express your love for me, both verbally and physically.”

“Hey cowboy! We better get it in gear or you may not get to have your way with me, if we miss the cocktails and you can't ply me with liquor,” she teased.

“Well we wouldn't want to blow that opportunity would we? How about you go in and shower. I can shave and shower while you are dressing?”

So they went about their preparations for the evening. Dave finished up showering and while Jill was still doing her hair and make up, he decided to wait for her in the living room. There he finished inserting the studs through the button holes in his shirt and fiddled with his tie. About 20 minutes later, as he was enjoying his scotch, Jill suddenly in the bedroom doorway and stood awaiting his appraisal of the finished product.

Jill wore an over the right shoulder black floor length gown with a slit running the full length of her right leg; it fully exposed her enticing leg seductively to the top of her bare thigh. She wore strappy silver heels that allowed her to exhibit her perfectly pedicured toes. Being strapless on her left side, she looked alluring with a peek of the top of her left breast, her shoulder and most of her back exposed so erotically. She wore her auburn locks up, highlighting her long swan like neck. She wore dangling silver earrings and a single diamond pendant that rested just above her cleavage. A tennis bracelet on her left wrist finished off her simple but elegant evening wear.

Dave was mesmerized by the beauty of his angelic appearing companion. “Holy crap Jill, for a woman in your forties..."

“Well Mister, for a man in his early sixties you look quite dashing in your black tuxedo. Your silver and charcoal striped tie will match up perfectly with my gown. I am sure that all the women there will be using my handsome prince for their eye candy for the evening. And thank you for your compliment on my appearance.”

“ Thank you also, beautiful. So you think all the other couples there will look at us with envy, because I do. How many have been married for years and their relationship has grown stale, to the point of just settling; certainly no longer enraptured with their mate?”

“Shall we my princes?s” as Dave offerred Jill his arm.

“Why certainly my prince.”

As they departed the elevator there were any number of people that were obviously not attending the banquet, but guests of the hotel. A number of them paid the lovers their compliments, either by the admiration in their eyes or some even verbally commenting. They made their entrance into the banquet hall at about a quarter after seven. With dinner scheduled at eight, this left ample time to mingle among the crowd and have Jill introduce Dave to the small number of new industry colleagues she had made acquaintances with during the week.

The editor of one of her industry's leading trade publications invited Jill to sit at their table to which she readily agreed. Her husband and Dave left the ladies at the table, making their way to the portable bar to refresh each of their drinks and get better acquainted. They hit it off well with both being strong baseball fans and thry each loved their golf games. They also were of the same age group and in related industries. When they returned to the table, they let the ladies continue to sit next to each other, while Dave took a seat to Jill's right and the other gentleman to his wife's left.

Jovial and lighthearted conversation continued throughout the dinner, with Dave loving the ability to keep his left hand occupied on Jill's thigh beneath the table. Jill parted her legs as she rubbed her beautiful and bare calve up and down on Dave's leg. With her providing him access to her delights, he soon discovered his naughty little vixen had chosen to go commando under her sexy gown. As his finger slipped into her pink pussy, parting her moist lips, he leaned over and whispered, “You little hussy; no panties?”

She leaned back and first licked and then whispered in his ear, “You silly man, a woman doesn't want to show panty lines; and if you keep that up, this little hussy is going to have a very difficult time resisting the urge to hump your fingers,” smiling and winking as she flirted and pulled away.

Dave turned a little red in the face, blushing a little, but also a bit flushed from the sexy attention of his escort.

Following dinner and a few comments from the conference leaders, the musical entertainment began and the loving couple took to the dance floor and enjoyed the next few hours discovering what accomplished dancers each were. This is something that neither knew about the other and a fabulous discovery at that.

With the crowd thinning out considerably, they decided to enjoy one more cocktail in the lounge around eleven, before heading up to their suite. Jill opted for her favorite, White Chocolate Raspberry Martini, while Dave enjoyed an Amaretto on the rocks. Their conversation continued as if they had known each other all their lives. They found each other's company so very enjoyable and commented that each had arranged for this extended time together with some trepidation, fearing that the person they knew online would be completely different in reality. Their fears were completely without basis, as they couldn't have been more pleased with their co-conspirator in this affair.

Dave could not keep his hands off of Jill's lovely leg and roamed between her thighs. The heat they felt soon overwhelmed them in lusty desires. “Come on commando, let's enjoy this the rest of this night together,” as Dave took Jill's hand.

While in the elevator, Jill sheepishly stated, “You know Dave, with the way you have been petting my kitty all evening and then with all of our dancing, would you mind if I jumped in the shower quickly when we get back to the suite?”

“No Jill, I wouldn't mind.” Dave grinned as he had some other plans for setting up what he felt might be a lovers covey, while she pampered herself. It didn't take long for Jill to get into the shower once they entered the room.

Dave then set a half dozen mandarin scented candles around the bedroom and retrieved a bottle of luxurious mandarin scented oil that he had hidden away in a warming blanket, along with a few surprise items that he felt might add to the nights sensuous activities. He then quickly stripped himself and entered the spacious shower behind Jill. “Mind if I join you?”

“You have no idea how I was hoping that you might do just that.”

They proceeded to tend to each other's bodies, with salacious kisses abounding and hands groping and exciting each other, rendering Dave hard with arousal and Jill humping her drooling pussy on his tight thigh. But Dave had other plans than sex in the shower and soon said, “Jill can we take this into the bedroom? I think we will be more comfortable there.”

With a pout on her pretty face Jill whined, “Oh, you spoil all the fun.”

“We'll see how you feel about that statement in a couple of hours. Lets get dried off and I think you might just enjoy what I have planned; you'll see fun alright. Besides, I'm the one risking a set of blue balls stopping like this, but I know the night is only beginning.”

After toweling each other dry, Dave led Jill into the bedroom and said, “Okay lover; how about we lay you face down on the bed and I give you a nice long full body massage?”

“Uhh … hmm, let me think about that … okay! You know, if I didn't know better, I might think you were trying to seduce me. Did you know that I love mandarin scented candles? And the warm glow is just the perfect amount of lighting. Are you trying to seduce me?”

“Trying? No … I already have lover. I already have.”

So she laid down and he grabbed the warm bottle of oil. She closed her beautiful blue eyes and he poured oil right at the base of her back and a thin line up her spine. He heard her moan in delight as his strong hands began to spread the oil and massaged it into her soft sexy skin. He was seated on her upper thighs with his half hard cock resting in the crack of her ass. As he massaged the oil into her back he kept moving slightly forward and back to an upright position. The touch of her hot body and this slight motion with his cock moving against her luscious ass, soon made his cock thick and hard.

He moved around so he could then give his full concentration to her lovely legs, first spreading more oil into her arches and between her toes and then gripping each of her feet in his strong hands. Up each muscled calf he proceeded and to those thighs he so loved to touch, kiss and ultimately spread and finally over each of those tight globes that were her perky little ass. He continued to attend to her entire backside as he spent almost forty-five minutes pampering this goddess of a woman, he loved.

He then nudged her slightly causing her to lie on her back exposing those luscious boobs with her silver dollar pink areola and perky nipples, her soft tummy he so dearly loved to rub and her pretty little pussy that he so enjoyed orally. The taste, the aroma and the soft warm feel of her miracle cavern with their full lips came flooding into his mind, as he watched her resting so peacefully.

But now it was time to further his plan for tonight. He noticed that Jill had become so relaxed she was actually sleeping. He slipped from the bed and gathered his new toys. He gingerly slipped a soft silk restraint on each ankle and wrist, then proceeded to secure the other end to the bed frame. So stealth-like were his movements that he didn't disturb her restful slumber. Then with catlike quickness, he slipped a blindfold over her eyes and around her head. This did wake her, but she was helpless to fend him off.

He calmed her fears with his low sexy voice telling her that she would know no pain this night, only pleasure. She believed him, or certainly wanted to believe him, but doubts kept sneaking into her mind as she thought of how recently she had first started chatting with him on Lush and had only just met him in person a few days ago.

“Dave ...”

“Yes Jill?”

“I'm scared ...”

“I understand Jill. I truly do, but I need for you to trust me. There is a purpose for me doing this and I will tell you later. Just understand, this is just you and me. There are no cameras, no one else is coming in to gang bang you and no one will harm you in anyway. Do you trust me?”

“I … I guess so,” she squeaked.

“Good. Concentrate on just how much you care for me and how much respect and love I have shown you this week. You know you can rely on me to want to show you that love.”

With that Dave approached her left ear and whispered, “Tonight my love you will understand more deeply just how much you mean to me.” Then he dipped his tongue in her ear, rendering a shiver down her spine and a moan coupled with a smile on her pretty face. Next he kissed and licked her right thigh perhaps four inches above her knee. Then he lightly rubbed small circles all over her tummy with his fingers. He then took her right index finger fully into his mouth; then gave her a passionate kiss on her full luscious lips.

“Oh Dave, I don't know what you are going to do to me next or where on my body.”

“That's the idea my love. But you are more comfortable with this now aren't you?”

“Yes … I guess 'um … yes, actually so far this is quite erotic.”

Next Dave took a small artists paint brush and lightly ran the dry tool over each of her eyebrows and then under her right underarm. She giggled with delight at the tickling sensation. Then he licked all around her left areola and sucked powerfully on her taut nipple. She moaned as if electric bolts shot from her nipple directly to her moistening pussy.

Recognizing the wonderful aroma of her arousal, he slipped one and then two fingers into that beautiful cunt and pleasured her for several strokes as Jill humped at his invading digits.

For the next half hour, Dave continued to randomly pleasure Jill's body. Her arousal and sensitivity were stronger than she could ever remember, as she experienced much more intense orgasms that seemed to encompass not only every inch of her body, but the totality of her mind!

She barely noticed that Dave had in fact actually released her ankles from their silk shackles, just before he thrust his cock fully through her soaked pussy lips and deep within her womb. She cried out in pleasure! “Oh Dave, yes baby. Fuck me! Please fuck me! I am totally yours. Do what you want, but please give me all of that cock! Oh I need that cock!”

Dave pumped his prick into her center repeatedly with thrusts so powerful that his own mind fogged over with the rapture that he experienced. He was, however lucid enough to remove her blindfold and release her wrists as every part of their bodies became fused as one. His life giving sperm released into her and blasting into her cervix, as for the first time in her memory, Jill released a torrent of her own ejaculate … she had actually squirted. The center of the bed was soaked, but both lovers relished the experience and made no movement whatsoever to unlock from their loving embrace.

“My lord Dave,” Jill chocked out between her labored breathes. “I have never … where did you learn … I mean, damn … where did you come up with this idea? Who taught you to do this? How many women have you done this to?”

“Oh Jill, you are the first woman I have ever done that to. I read a fictional story online several years ago and planted it deep within my mind. I knew that some day with the right person, I want to do that. I just knew Jill, that you were the one.”

“I don't know how to thank you enough Dave. I have never felt such pleasure … ever.”

“Well, lover, that was the purpose, your pleasure, along with developing a stronger sense of trust that you would have for me.”

“Mission accomplished my Prince … and my lover.” And they slipped into a wonderful, deep sleep while still locked in a loving embrace and his now softening cock still lodged in her drooling pussy.

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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...

2 years ago
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One Chicago Visit

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...

1 year ago
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Stupid BoyChapter 21 Chicago

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...

1 year ago
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Rendezvous

Rendezvous “Let’s see… sandwiches, crackers, cheese, bottled water… check, check, check… and check! Napkins, table cloth and wash cloth… check” Glancing at his watch, Sam saw that he’d better get a move on or he’d end up being late… again. Closing the picnic basket, he grabbed his keys and headed out the door. Out of his apartment and down stairs to his car. As he was putting the basket in the back seat, he remembered something. “Damn!” he said aloud, turning to rush back up and to his...

2 years ago
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Chicago Chicago That Toddlin Town

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...

3 years ago
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One Night in Chicago

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,...

2 years ago
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A WellLived Life Book 7 Kara IIChapter 28 Sweet Home Chicago

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...

1 year ago
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Scenes From an AffairScene 7 June 1984 Chicago

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...

4 years ago
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My Mothers LoverChapter 12 Apres Chicago A New Beginning

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...

1 year ago
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Hot Wife KatieChapter 12 Katie visits Chicago

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...

1 year ago
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Fullfillment in Chicago

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,...

Erotic
3 years ago
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Chicago 42 Part Two

The 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....

Historical
1 year ago
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One Night in Chicago

Weekend 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...

2 years ago
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Pakistani Couple Swings in Chicago

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...

3 years ago
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Letter from Chicago

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...

3 years ago
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Return to Chicago

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...

1 year ago
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Japans Ayumi Tahara in Chicago

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...

Interracial
3 years ago
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Chicago Nights Ch 01

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,...

3 years ago
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Chicago in the Autumn

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...

2 years ago
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The third night at Chicago

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...

3 years ago
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A not so boring business trip to Chicago

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...

2 years ago
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Joan 9 we go to Chicago

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 Lovers
4 years ago
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Denver to Chicago

Many 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...

2 years ago
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Pussy play on the Chicago L train

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...

3 years ago
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Chicago getaway

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...

2 years ago
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The Long Train to Chicago

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 Sex
4 years ago
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Sissy gets creamed in Chicago

I 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...

3 years ago
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Pakistani Couple In Chicago Part 1 The Swing Club

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...

4 years ago
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Chicago

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...

2 years ago
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Chicago 8211 Mumbai With Sheetal 8211 A Beauty With Brain

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...

3 years ago
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Hot Pankhuri In Chicago USA

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...

3 years ago
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Wife Fucked in a Chicago Jazz Club

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...

1 year ago
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Jill Gets Fucked In Her Chicago Motel Room

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...

3 years ago
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Welcome to Chicago

  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...

1 year ago
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A WellLived Life Book 10 The WifeChapter 5 Chicago

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,...

1 year ago
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Scenes From an AffairScene 11 2009 New YorkChicago

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...

3 years ago
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Rendezvous At Kuantan Beach Ch 1

Kuantan hyatt is really a great place to go… with the relatively clean sandy beaches and the proximity of the beach to the resort really makes the trip that much more enjoyable… I sometimes daydream about going there with you again and I’d like to share it with you so I don’t have to think about it… hehehehe [now it’s your baby… hahahaha]. I read an article once and it says if u have something to say to someone, then say your peace and be done with it, then it’s the other person will have to...

2 years ago
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Rendezvous Pt I

Rendezvous It started out as a typical Saturday, with not much going on except a couple of phone calls that weren’t of any consequence. Lounging on my sofa, listening to some music, and reading Catch-22 seemed like a proper way to allot my time. Steely Dan was wafting through the speakers when there was a soft tapping at my door. I sure as hell hoped it wasn’t some damn Jehovah’s Witness trying to sell me Jesus. Christ isn’t for sale, as far as I know, and a theological discussion with some...

3 years ago
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Rendezvous

Rendezvous He sat nervously at the hotel bar, his hands idly playing with the edges of the napkin that his drink was resting upon, his third drink. He didn't often drink like this. Normally one or two beers will suffice over an entire evening. But today was different, today his throat was perpetually dry and his hands needed something to do. Finishing his drink, he looked at his watch again and noting the time he ordered another Captain and Coke. How much longer, he wondered. How much longer...

1 year ago
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Rendezvous with Cheryl

Pulling up to the motel my cock was already rock hard just thinking about Cheryl. It had been a few months since my last trip to Baltimore and I so wanted her. We had met on craigslist about a year ago and rendezvous a few times. Now it is kind of a regular thing whenever I am traveling through. Cheryl always grabs a room at this seedy super 8 and then text me the room number. Cheryl looked so sexy today she had dark brown shoulder length hair that curled at the end, nicely lined eyebrows, long...

2 years ago
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Rendezvous

Chapter 1. The Rendezvous The midday sun came streaming in though the windows and warmed his chest. Today was the day! As Gene drove the winding path to through the tangled vines, he had a slight knot in his stomach. He had thought about today for many weeks after the date had been set. Would Alyssa find him attractive, or would she be disappointed and feign an excuse to hurry home. While they had spent hours together on email before getting the courage to talk over the...

4 years ago
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Rendezvous laDiablo

Rendezvousby laDiabloPart OnePrologueI hold the card key you left for me at the front desk, but I don't use it. I knock instead, standing there, with my head down...As you open the door, I see the spiked heels first... I scan up, taking in the stockings, the form fitting skirt, the belt, the button down white blouse open to reveal the lacy white bra beneath.Your hair, perfectly styled to partially hide your eyes, is so sexy...Everything about you is perfectly as I requested. I am pleased.I tilt...

3 years ago
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Rendezvous Pt I

Rendezvous It started out as a typical Saturday, with not much going on except a couple of phone calls that weren't of any consequence. Lounging on my sofa, listening to some music, and reading Catch-22 seemed like a proper way to allot my time. Steely Dan was wafting through the speakers when there was a soft tapping at my door. I sure as hell hoped it wasn't some damn Jehovah's Witness trying to sell me Jesus. Christ isn't for sale, as far as I know, and a theological discussion with some...

Love Stories
3 years ago
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Rendezvous IIChapter 40

Karen In the morning I signed the Lottery Ticket and stashed it back in the cash box. The drawing for the Monster Millions was at 8:59pm Mountain Daylight Time Wednesday night. The Drawing was actually held in Tallahassee, Florida at the National Headquarters. Monster Millions is a 5/75 with a 1/15 monster ball. The first five numbers are done with actual balls in a bingo 75 ball wire roller cage. The monster ball is taken from a separate bingo 15 ball roller cage. The mixing is through a...

2 years ago
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Rendezvous IIChapter 42

Karen Angie said, “That is NOT what I wanted to know ... and you know it.” Since I had to give a commercial about winning I was pretty sure my name and picture would be plastered on every newspaper and TV screen in the United States. I didn’t wanna do it ... but Montana has this law... I was stuck. So ... Artie stepped out and scratched on the tipi cover. “Karen, you’re on TV,” he said. Then he asked, “That much?” The dash to the office rivaled the Yankees winning the Series. Since I...

2 years ago
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Chicago Part 1 when I lived there

My 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...

3 years ago
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Chicago 2035

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,...

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