Kyle In Chicago free porn video

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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 out getting back in shape. Not that I was too out of shape I, by many accounts look good. I just needed a bit of toning up. My appeal with the woman really started when I shaved my head. Being a Black Male who is Tall, Medium Dark, Hansome and Bald seems to be attracting all types of women.…. Hope you enjoy my stories….


It was my first trip out of town since my divorce was final. I never was a chick magnet when I was younger so I felt that it would be hard for me to meet ladies. I had always been faithful to my wife. She had always told me that women were always giving me the double take. I never noticed after all I was spoken for. So this trip I thought that if I kept my eyes open I just might get some action.

I think I’m a good lookin guy. I’m tall (6’4’’) with a very athletic build. Wide shoulders and narrow waist, I weight about 220 pounds. I don’t look 43. People tell me that I look 30ish. People say I look like a taller Montel Williams, muscles and all. My wife is hot looking. Blonde, with long legs and a down right beautiful face. I don’t go for cute woman I go for sexy ones. Kathy was definitely sexy. Too bad she left me to munch carpet.

This time my trip took me to Chicago Midway Airport. I was just passing thru , I needed to change planes because I was due in Green Bay in the morning. Bad Luck would have it, my plane was cancelled and I would have to stay the night in Chi-town. I was not alone, several people were in my shoes. Two people in particular. Ellen and Stu.

Ellen was a stunning brunette with large tits that fit on a tall slender body. She had a nice walk that featured a great ass. She and Stu were in line in front of me waiting to find out where the airline was going to put us up for the night. It just so happened that we had 3 choices and the three of us all unknowingly chose the same place. I made my choice based on which hotel had a bar. I suppose that they did as well. I suspect that they had a head start on me. They were acting a little loopy.

In line we chatted a bit. The two of them seemed somewhat close though I did think that they just met on the plane up. I did not think that they were together together because of the conversation and the fact that Stu looked to be 30years Ellen’s senior. Nice guy and all but I just could not see them ever “getting busy” She turned and smiled at me a few times ( guess that the look that my ex was talking about) I didn’t think anything of it until she turned, took my hand and said “I hope to see you at the hotel bar in a few. I’m lookin for a good time tonight.” Now while married I would have considered that to mean drinks, jokes, and good night. Now, with my eyes wide open, I saw something that suggested that, if I played my cards right it would be better than a good night.

At the bar, Ellen sat between Stu and me. I noticed that Stu started to become touchy with Ellen. Touching her arm, and leg. She didn’t seem to mind but as he moved closer to her she would move closer to me. The couch got smaller and smaller and soon she was pinned between us. That lasted only a few minutes. She reported that she needed to go to the room. I slide over. She moved past me stumbling a bit. She fell right into my lap. I looked at Stu and he was not happy. He had the look of an old man chasing after some young thing. I think it was at that moment that I became the competition. Before that I was just the third wheel.

On the way up she grabbed a handful of my manhood. Held it tight for a second. Let it go and patted it twice as if to say “easy big boy I’ll be right back.” Excusing herself she went on. Stu could not see what she had just done. The table was in the way. I am sure that my face didn’t give her actions away. I have a reputation for never being surprised and having a great poker face. My cock would have given everything away as it was now beginning to swell.

When she was out of site Stu did not hesitate to tell me that he was planning to fuck this chick. “My cock is ready for this hottie” he said.

I said “Go right ahead don’t I won’t stand in you way. I’m just out for some drink and a good time.” All the while thinking, man if she fucks you, not only will she snap your spine but she will give you a heart attack as well. When she got back to the table she slid past him. I know she grabbed his piece because I could see it in his eyes. He hadn’t had that happened to him in a long time.

A minute or two later it was his turn to hit the room (probably to jax off and take his Viagra). Ellen shouted to him that he better not come back without another round. When he was out of site, she turned to me, grabbed my cock again and said “Damn that feels nice. I want that tonight.” I looked at her sharply. She continued. “ Look, I am gonna flirt with him big time. I want to get him to pay for our night. I have no plans to fuck him and his little dick.” Squeezing my hardening cock she said “ I want this in my mouth, between my legs and up my ass!!! Got that!!!

I’m not sure I heard her because at that point she started to stroke my cock through my pants. In any case, I shook my bigger head yes because it seemed to be the best thing to do at the time.

“Continue to play the third wheel and it will cum out great for both of us.” She let me go, slid over a bit just as Stu came in to view. He stopped at the bar and brought back a round.

Finish up guys. I want to go dancing. You up for that Stu?

“Sure lets go baby”

“Kyle you want to come along?”

“Well” I hesitated “ I don’t want to interrupt, but if you think it’s OK… “

Before Stu could say boo, Ellen moved in his direction, put her arms around him and said “Sure it will be a blast, and Stu won’t mind will ya Stu.” Sliding her hand down to his crotch. Stu’s eyes rolled back. It was obvious that she hit his Jack Pot.

Chicago has many Blues halls that have great Blues dance music. We hit one of the more famous places and after Stu paid the cover we continued the party. Ellen rushed to the dance floor Stu and I hit the bar. Ellen was not alone on the floor. There were a few couples doing there thing. Ellen danced by herself for a while and every guy in the place was watchin her. Seductive and hot could only explain her movements. Her shirt was buttoned lower than I remember. Her tits were all but out of her visible bra. Playing the role of the third wheel I suggested that if Stu wanted some tonight he better get out there and claim her before some shark in this tank does. He thought it was a good idea so he got up and started gyrating with her.

I knew he could not keep up. The bump and grind gave Stu a pup tent that was noticeable (if you looked hard enough). After a few dances they came back to the table. Stu collapsed in his chair. Ellen was hot and hyper. She sat down for one song and jumped up when the next one started. She was out on the floor alone when a hot little number joined her. Jill was short and built like a brick shithouse. She had a tight, well proportioned body with huge tits. I never saw Dolly Parton live but I would imagine that this is how she looked.

The two were doing a great job of clearing the floor. Everyone in the place got a seat so they could watch the show. Tits were bouncing, asses were shaking, hands were roaming and dicks were getting hard. After a few songs, including a slow, sexy, bump and grind, Ellen brought Jill to the table to meet Stu and I. Ellen jumped into Stu lap and made it clear that she was with him. Reaching under the table again. After some small talk the two went to the ladies room together. While they were gone Stu said “Man we got to go real soon she is wearing me out.”

After a while, Jill and Ellen returned from the bathroom hand in hand and smiling. Ellen announced that it was time to go and grab Stu and headed to the bar. Jill asked me if I had an extra key to my room for Ellen. I said sure and slipped it to her. A moment later we were getting together to go. Jill hugged everyone and said her goodbyes. Ellen, Stu and I went out front and caught a cab. Stu told me that I should sit in the front. I did. I am quite sure that he got a hand job on the ride home. I noticed a big wet spot on the front of his pants. Not to mention his eyes were rolled back in his head again. Once inside I said goodbye to Stu and Ellen turned to me and said with a big smile “had a great time hope to see you again soon” the hug was great. She grab my ass hard. My cock stiffened. I could tell she noticed. She moaned in my ear.

I left those two and proceed to my room. I opened my door and a female voice said “close the door and strip everything off”. I did not recognize the voice, I thought it was a mistake. She said it again. I was slow to react. A hang grab my package and that helped convince me.

“Ellen was right. You do have enough to satisfy both of us”

It was Jill from the club. Damn!!! My cock swelled to new heights. I jumped out of my clothes. She fell to her knees, took my cock in her hand and guided it to her mouth. I was surprised at how much she could handle.

“Damn, you’re so long and thick. I can’t take the whole thing.”

She had about half in her mouth and was pumping the other half with her hand. In the dark I could only imagine what a beautiful site that was. Her head gobblin up the head of my cock and her white hand wrapped around my slick black dick. I know it could not feel any better. With her free hand she grabbed my ass and then slipped a finger up my hole. I blew my wad in a hurry. This was the first time I had cum, by means other then my own hand, since my divorce and I didn’t even have the benefit of seeing it.

I found a wall to lean on. Jill found the light by the nightstand. “Ellen said you were gay and had no interest in cock” I asked

“That was until she told me that Black Cock were the biggest and the best. She said that she loved black cock and would not mind sharing.” Jill replied

“I second that emotion!!!” Ellen announced as she slipped in the door. “Lets get down to some fuckin.”

Feeling like a stud who’s just won the lottery, my mind flew back to the days before my marriage. Not that I had ever had a threesome before but I have seen many a porno.

“Ok girls, up on the bed. Tails up”

Both women got on the bed ass to the ceiling. Ellen’s ass was great and her hole a some hair around it. I slide behind Ellen and worked the head of my cock in her warm cunt. She took it well. She growled at me and I knew she was going to be a noisy fuck. I love that type of chick. I worked my head in and out. She was beggin for more as I slide behind Jill. Her ass was a bit bigger than Ellen’s but her cunt was hairless and smooth.

Easy big guy I ain’t had a cock up there in a while and never that big. “ I will take that into consideration.” Said with a laugh. My cock was wet with Ellen’s cunt juice only up to the head. So that’s all she got. I could swear that that was all she was going to get because she was tight. When I shifted back to Ellen. She wanted more and she got it. I worked my way way up that hole. Getting my entire pole wet. Ellen was moaning and groaning. She started to shake when I pulled out. I don’t think she came yet but she was right there. I went back to Jill. Told her to relax and I started to work my cock in. As I got half way in she slammed her face into the pillow and started to sob. I stopped, leaned forward and ask her if she was OK.

“Oh God that feel so great. My cunt hole is on fire. Are you all the way in yet.”

“No”

“Oh please give it to me. Give it to me slow but I want it all.”

I flexed my cock a few times to give her a chance to rest and then I went back to work. She was breathing deep. I felt that this could take a while so I put my hand on Ellen’s ass and took the liberty of sticking my finger first in her cunt and then up her butt. A low moan came from her direction. She was clearly approving this action.

Finally, I hit bottom. Jill was squirming and chanting “Give it to me… fuck me harder, Give it to me… fuck me harder” So, like a big stud I did. She came with a scream. I was still hard when I pulled out. I moved over to Ellen who was starting to beg for some dick. She said she was tied of the finger. I began to work myself back into her cunt when she stopped me.

“I need to take it up the ass. I love it that way.”

“I’m here to please, baby.”

Hot damn I was about to get my first piece of ass, literally!

I took it slow. It took a few minutes. I had my eyes closed as I was straining to get that last inch in. I only opened my eyes, I was surprised by Jill. She was on her back, between Ellen’s legs. What surprised me was her lickin my balls!!! She was taking turns lickin my balls and suckin Ellens driping cunt. Ellen was in heaven. I was giving her the long stroke treatment and Jill was giving her the small stroke treatment. I wasn’t long before we both blew. Jill must have been in that position before. She knew exactly when to roll out of the way. Ellen collapsed onto the bed Jill was not under her.

I rolled over and found myself between the two women. We were still for a bit. Then Jill reached down and started things up again. Once hard, Jill jumped on and road me like a champ. For a woman who didn’t know if she liked dick, she was putting dick thought the paces. Ellen was cheering her on to another explosive orgasm. Jill collapsed onto my chest. Ellen got behind Jill, pulled my cock out of her cunny and replaced it with her finger. She slid it in slow, Jill moaned, “I’m not ready yet”

“Relax” Ellen said “breathe deep” as she Glided her finger up and down her butt crack.

“Oh I like that”

“Hold on girl, what do you think about this.” Ellen push her finger past the brown star. Jill gasped but did not resist. ”I love it up the ass!!! You need to have some of that black dick up there.”

I couldn’t take it!!! It’s too BIG!!!

“Don’t worry I will warm you up to it. It will be fine” Ellen said as a second finger found it’s way up her butt Jill moaned again. As I heard this talk I could not believe that I was gonna get a second piece of ass and this time it was gonna be virgin butt. My dick started to rise to the occasion helped along by Ellen jaxin me off. A third finger found the mark. Jill was being slowly stretched I could see tension come and go from her face. I could feel Ellen bend my cock up to Jill’s entrance. Ellen whispered “ This will hurt if you don’t relax the head is the biggest part. Relax and breathe.” I felt the head knocking and in a second it was in. Jill was loud and tight. She wrapped her arms around me and held on tight. I didn’t move until the tension was gone from her face. I know I’m big so I wanted to be gentle. I knew that in this position I would not be able to slip my dick all the way in and I don’t know that for her first time she should have all I got. What I was giving her seemed to work. She was chanting and squirming her butt. What she was doing work for me as well. I could not hold back and I shot a load up her butt, she loved it and shook herself to another orgasm. I think she passed out I rolled her off me and once again found myself between the two women.

We slept for about four hours, When I woke up. Jill was gone, but she left a card. She was a bank president. I chuckled thinking about my late night deposit. Ellen was still with me. Needless to say we both missed our morning flight. We were busy. I was glad to have her by herself.

She told me that she did indeed jax off Stu in the taxi. She told him that that was to thanks him for all the drinks. When she got to this room and he invited her in she said no and asked him “what type of girl do you think I am”. She added “ I don’t fuck guys with tiny dicks”. We both had a laugh about that.

I still stay in touch with Jill and Ellen. I have not gotten back up that way but Ellen has been with Jill on a few occasions. They usually call me when they are together. They love to tell me how much they enjoyed my big dick. (The phone sex is great as well… They can get pretty raunchy). We are planning a get together to have a reunion soon… By the way Stu will not be invited.

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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
1 year ago
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Kyle fantasy 2 Bedroom encounter

So Kyle popped up at his window yesterday morning, you see his upstairs bedroom faces my downstairs bedroom, while babysitting him in his house I've explored the view he has of my bedroom, when he stands directly in front of his window he can see me at my desk, and when he looks through the lower left portion of his window he can actually get a pretty good view of my bed, for this reason I've been very careful not to roam around my room nude with my blinds are open. So he called down to me as I...

1 year ago
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kyle and the amoba lake

kyle was an 19 year old collage student in Maine and is sometimes bored about almost everything in his life and most of the time he's often lazy, he had some great hobbies like swimming, exploring, traveling, fishing and camping. today we see him wandering the woods carrying his camping supplies looking for a nice spot for him to camp out, that was until a really strange lake caught his eye and went over to investigate it. he layed down his supplies and walked over at the edge of the lake and...

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
2 years ago
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Kylees Sauna Fantasies

Introduction: Tranny fucks guy in sauna and brings him home. Last Saturday I went over to a friends house to eat and he had his sister, Kylee, over for dinner. For some reason it seemed like they didnt like each other very much. As the food was set out to eat they argued over who was going to sit where, she wanted to sit next to me, but my friend was the man of the house and he won the debate. Rosa sat across from me. She sat down slow and winked at me while doing so. We were having a roast...

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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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...

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...

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,...

2 years 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...

1 year ago
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Andees Sexual Adventures Continue in Chicago

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...

1 year ago
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Meeting in Chicago

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...

3 years ago
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Rendezvous in Chicago

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...

Cheating
3 years ago
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Andees Sexual Adventures Continue in Chicago

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...

Wife Lovers
2 years ago
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  • 9
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Chicago

CHICAGO.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...

2 years ago
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Meeting in Chicago

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...

Straight Sex
3 years ago
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  • 11
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The hotel room in Chicago

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...

4 years ago
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Encounter in Chicago

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...

1 year ago
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Kyles conversion

This is my first story, I have enjoyed all of yours and though I should finally submit one, I hope you enjoy. Please leave comments. Come on Kyle, just take them off no one will see us. Todd said again, finally Kyle relented. Todd and Kyle had been friends ever since Todd moved in across the street, 10 years ago. Kyle and Todd were 16 and 17, it was the end of their sophomore year, and they'd just started to enjoy a summer unsupervised while their mothers worked. Kyle's mom never...

3 years ago
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The Trip to Chicago

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...

3 years ago
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Sex With Horny Girlfriend In Chicago

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...

1 year ago
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Card PartyChapter 23 Chicago

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...

2 years ago
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The Love ExpressChapter 8 Sweet Home Chicago

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...

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