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"Damn it, she's single.", thought Gregg. He had been surfing the dating sites, looking for a married woman for three days now, with no luck. How he hated to see that dreaded "S" beside a woman's name. He wanted a married woman to romance and seduce. He'd had seven already in the last three years and he'd found them all on sites that allow you to select "married" in your search for a partner. Matchdoctor was his favorite. So now he sat staring angrily and helplessly at Sheila's profile. She was 35, a few extra pounds with short, reddish brown hair. She liked "indoor sports" "cuddling" and "spoiling her man". All the attributes he looked for in a married woman. He shook his head and clicked to the next profile: Dorothy. 44.

This one was classy. Dressed in a dark blue evening gown and pearls. His heart raced. He scrolled down to her marital status. All his attention galvanized and he stared as the letter appeared: M. Scrolling further down, he saw that she was "just looking for online friends". Gregg knew that that was just code for: "Let's get to know one another first, and if I like you, we'll see." Now, he was really checking her profile out in earnest. She lived in Canterbury, about 40 miles from him. She liked windsurfing, collecting sea shells and whist. She said she was 6 feet, 138 pounds. A brunette. It was hard for him to tell how long her hair was, because she had it up in a pretty, fancy hairdo. Other than her picture and the fact that she was married, two things helped Gregg to sink his teeth into Dorothy's profile; the line "...looking for online gentlemen friends" and the fact that she did not mention her husband once on it. He obviously took good care of Dorothy, though, money-wise at least. Those were the wives Gregg wanted and loved the most: The ones who were smothered in posessions and a nice house and landscaped lawn but were completely neglected emotionally and sexually. The more well-off women were sharp as a tack, too. They always stayed one step ahead of their husbands and usually didn't slip up. Most of the rich husbands didn't even care enough to notice that their wives were having an affair, anyway. They were too busy making money and golfing.

At 32 years of age, Gregg had had married women from age 17 up to 68. (The 68-year-old had offered to leave her husband and marry him, even offering to allow Gregg to continue his online activities). She was almost begging him and proved quite hard to get rid of once he had tired of her and decided to move on. He had been 24 then, and his all night sex had made her as giddy as a schoolgirl. She said she'd die if he left her. In reality, the only thing that died when he left her was his cum inside her mature pussy. She'd had five weeks of sexual heaven. Her husband, a retiree who often left for fishing and hunting conventions, hadn't suspected a thing. He had thought that no young guys were after married, mature women his wife's age. He couldn't have been more wrong. Unlike some guys, Gregg wanted to know all about a woman's husband. In lounges, restaurants, hotels and chalets, he would listen intently as his date would describe her husband and their relationship. Gregg especially loved the photos. He wanted to see the face of the man he was replacing. The man who would be paying to raise Gregg's child if he impregnated his wife.

He e-mailed Dorothy right away, making certain that he appeared polite and professional. To his surprise and delight, he received a response from her the next afternoon. She thanked him for his interest and asked him for a photo. He zoomed one off of him lying on his side on the bed, wearing only a smile and a black thong. Underneath, he daringly wrote, "Can we meet for cappucino?" When Dorothy received it, she didn't know whether to get angry or not. She got up from the computer quickly and walked to the wide bathroom mirror to fidget with her gold earrings. She looked at her face in the mirror, wondering whether she could attract a young, thin, muscular guy like Gregg. She lifted her skirt to look at her violet, satin thong. No one knew she wore a clit clip but her. Not even her husband. Dorothy walked to the computer, intimating a decisiveness. She sat down and was tempted to fire off an angry, defensive response to Gregg because of the revealing photo of him, but considered instead that she was getting no younger and that she and her husband no longer loved eachother. She typed out only, "Make mine a double". Before the week was through, Gregg was watching Dorothy's expensive diamond wedding ring rise and fall as she drank her cappucino. A womans wedding ring captivated Gregg. It was the symbol of his extraordinary erotic victory. He would often kiss it during sex and when they parted after a meeting. Most of all, though, he loved the feeling of it on his back as he ploughed the man's wife, forcing orgasm after luscious orgasm from her helpless and grateful pussy with his 9" cock.

After they met and kissed, Dorothy asked, "Are you married, too, Gregg?" She had already committed to having sex with him if he asked. "Do you really care?" he replied. "No... Not really..." she said with a smile. He watched her from behind as she entered the bistro. She wore a tight purple blouse and a skirt that barely covered her knees, but Gregg could not tell by her body language alone if she was ready to ask about sex. When they sat and he got a good look in her eyes, he got the answer he needed, though. He made sure she saw him checking out her breasts as they sat and talked about their lives. She pretended not to notice or care. After a short moment of silence, she took the initiative. "I lied to you out there, you know..." she stated. "What do you mean?" asked Gregg, amused. "I told you I didn't care if you were married or not." She said, sliding her hand a tiny inch closer to Gregg's. "You mean you wouldn't want to see me again if I was married?" "No." answered Dorothy. "That's not what I mean." She looked piercingly into his eyes and then, looking away, said, "I want you to be married. I like to have someone to compete against." She took a bite of a breadstick and looked down her nose at him, smiling with her eyes.

Gregg felt his cock swell and rear up after hearing that. That was one of the sexiest things that he had heard in a long time. Maybe because it reflected his own feelings. He stood forward at his bench seat, held her head on it's sides with his palms, and kissed her very tenderly and long. After the 17-second kiss, which felt to both of them like an eternity with the intensity of flying past the sun, they parted their lips, both his and her nipples now erect. "I know exactly what you mean." he said, breathless. "I know exactly how you feel." Dorothy then commented, "To take a wife's husband away from her, even for a short while, is the ultimate conquest of her." Gregg gently took and held her hand on the table. "That is exactly how I feel about taking a man's wife!" "Unfortunately, I'm not married, though." he stated, pleading with his eyes. Dorothy didn't lose a beat, even though Gregg was going to be her first tryst in her 16 year marriage. She asked resolutely, "Would you be willing to get married? For me, I mean?" Gregg had barely considered this idea, even in masturbatory fantasies. "How would I do that?" he asked. "Getting married isn't that easy!" "Come on." She said, rising from her seat and grabbing her sunglasses and purse. "I'll explain it all on the way there."

In Dorothy's Lexus, Gregg rolled the passenger window down and asked, "Who is it I'm going to meet?" "It's my sister." replied Dorothy. "She is about your age. You told me you work with art, so you will get along fine. She works with paintings too." She paused, shifted, and said, "I want you to go for it sweetbuns. Take her out for a few drinks and pop the question to her as soon as you want. Ok?" Gregg found himself saying, "Ok", looking down at his date's exposed nylon-covered, married legs. This was going to take some work, being with her, he realized, but that it was going to be fucking intense, too. "I changed my mind." she said, and took a hard right turn. They pulled up at speed into a driveway of a house with a For Sale sign on the lawn. "I told you my husband was realtor..." She said in a sexy tone, smiling at Gregg. "Now I'm going to fuck your brains out." she added, matter-of-factly. They walked with their arms around eachother's waists and Gregg could almost feel Dorothy's leg's trembling, she was so excited. It had been 3 years and 11 months since she'd had sex. She was wondering if she was wet enough for Gregg to enter her. "Today is just a freebie, sweetipie", she said, "...but I want you at least seriously going out with my sister before we do it again. Ok?" "Absolutely." He told her. He was 100% into it. He didn't care whose heart he broke, or how many, and neither did she. It was all part of the fun.

She sat right down on the new berber rug in the den and, taking off her shoes, asked, "Do you want to see a picture of Jen?" "Who's Jen?" asked Gregg, sitting down beside her. "My sister, you lug..! The woman you're going to marry!" She unbuttoned his white dress shirt greedily and clamped onto his chest hair with her teeth. He gave a little scream of pain. She gave a little scream of passion.., and let go. As she lapped and sucked his nipple like a starved woman, he gasped, "Yes. I want to see her picture." "Here. " she said. "I'll lay it here so I can see it while we are having sex. I want to see who I'm conquering. I have a picture of my husband here too. Do you want me to put it down so you can look at it while we have sex?" Gregg almost gave into his normal impulses and said no, but he wanted to at least glance at this man's face. In his eyes. When he would cum deep inside this man's wife minutes from now, sending hot ropes of his D.N.A. into her body forever, he would look at the picture, feeling the man's wife's heels pumping on his buttocks, urging his cock into her as far as he could possibly push it.

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Note : This story is completely fictional! hello reader here is a live a life of fantasy. They have wealth and love. They are happy. But the life of them is a forbidden one. If any but those with very open minds discovered them they would be condemned to the eternal depths of Hell. Regardless, the member of one who have will tell their story. Read and cum my reader It’s Incester special. Most people, even though they would rather die than admit it, would kill for my life. My father, now dead,...

Incest
3 years ago
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Drawing on the Dark Side of the BrainChapter 21 A Fantastic Woman

“Is this a test?” Jas asked. “Only sort of,” I explained. “It’s a class project. We’re supposed to create a work of art that captures, in some way, the effect of Akhenaten’s changes in ancient Egypt on today’s art. You are perfect for my Egyptian canvas. Will you do it?” “You’ll use the water-soluble paints so I can shower it off afterward?” “Jas, sweetheart, I will personally bathe you and massage you until all trace of the paint is erased from your body.” “Bathe and massage? I’m in. I’m...

2 years ago
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A Day in the Life

I walked into the kitchen that afternoon and my mother was there, smiling at me. "Hi Mom." "Hey Wendy. How's school?" "It was okay," I shrugged, dropping my book bag and sitting down at the table. "Do you have homework?" she asked and I shook my head. "No, not today," I smiled and she was putting a sandwich down in front of me and a glass of milk, as always. "Okay," Mom said and then narrowed her eyes as I'd been a little immodest sitting down. "Where are your...

2 years ago
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Semper FiChapter 15 The Battle

Mortars exploded no more than thirty seconds after his daughter had departed. Hitch and Kieu-Linh quickly donned helmets and flak jackets, then rushed out to find protection. Old instincts had Hitch rising for a fight, his mind already taking in every detail and craving more. Plumes of dust were close by, and more impacts pounded within a hundred meters. Hitch heard shouts around them, the rattle of a .50 caliber exploding to their east. "We're being overrun!" a man shouted with...

2 years ago
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A Surprise Threesome

We are out at a bar and have had a few drinks. We've been dancing and this woman seems really into you. She's 38, divorced ans wearing boots, a short skirt, and is making a point to show us her stoking with garters. We are all dancing together and her hands are all over both of us. We go back to our table, drink a little more, and she puts her hand way up your skirt. You tell her how wet your pussy is as you lean over to kiss her. She slides her fingers into you, then offers them to me to...

4 years ago
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MactownChapter 3 Rachel is too young for Strip Clubs

Hank: “They’re your clubs aren’t they?” Hank didn’t like the Investigator’s in his office. What would the kids think? “Investigator, I’ve had this conversation numerous times with the police. I assure you my clubs are up to date to the highest standards, codes, and regulations.” “I’ve heard different.” Hank shrugged, “I don’t really listen to gossip.” “Well we do,” The Investigators eyed him, “Listen I knew we’re new here, but there’s something going on in this town. And I’d like your...

1 year ago
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Freda and Jenny become porn stars

Freda came from a loving family. She was a sweet girl and her mother and father worshipped her. It was time for her to go to college and she would live alone for the first time. Well not exactly alone. She was going to share an apartment with another girl. Her name was Jenny. Freda had all her clothes packed and her parents kissed her good by. Freda drove away in the used car her father had given her. Freda was sad and homesick already but as the miles slipped by she sensed that she was going...

Lesbian
3 years ago
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Married Strangers Enjoyed Honeymoon Together

Hi everyone, my name is Vikram a big fan of ISS and have been reading stories for a very long time. I am from Delhi, 5’7″ tall, aged 41 years, very fair, good looking married guy. This is a true sex story which happened three months ago. I went to south Delhi to an astrologer to show my horoscope and on reaching there I found that it was a bit crowded and my number was 10th on the waiting list, so I sat in the waiting area for my turn. Just after me, a lady came with her kid who was just one...

1 year ago
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Allison The Lifeguard Ch 01

This is my first story, I have a long way to go so any and all comments are welcome. I’ve read a ton of stories here and am sure I stole lots of elements unintentionally from authors I greatly admire like JukeboxEMCSA, Trilby else, Softi, and HypnoAddiction. I hope I don’t do them a disservice by even mentioning them as inspirations * I settled into my chair by the side of the pool, starting my afternoon shift as the lifeguard at the small, family hotel. The indoor pool was crowded today...

4 years ago
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Taking OliviaChapter 2

I awoke abruptly just as the first light of dawn was pouring in through the bedroom window "I'm in here!" a voice yelled. "Please help me!" Jumping out of bed, I searched frantically for the ski mask and pulled it back on over my head. I scrambled towards Olivia's bedroom door and fumbled with the lock. She let out an ear-splitting scream as I entered and tried to dodge past me, making a dive for the open doorway. I pounced and wrestled her to the ground but the minx fought with all...

3 years ago
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Blood of the Clans Ch 27

The dark, purple clouds hung low on the mountains, heavy with moisture and were releasing their burden rapidly. The fierce winds were driving it on a slant, almost level to the ground, but five riders were mounted and ready to ride north, soaked already but unconcerned with the weather. Harlan looked at his clan and then to the others riding with him. Eamon had agreed to go to see James MacRae and explain what they had found to him. He was completely unaware of the ramifications his disclosure...

3 years ago
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Date Night 2 A Date Weekend

A DATE WEEKEND After our successful first date, Hannah and I kept in regular contact via email. True to her word, Hannah tried to set up a second date for us to go for a meal together on her side of London for a few weeks hence. However, as so often happens when you are trying to set a date for something you would really like to do, it proved impossible to match diaries. Although we tried juggling other commitments, we just couldn't find a suitable evening that we could both...

2 years ago
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Lily Plucked And Fucked

Hi, my name is Lily. I find many interesting stories in this site, but not as exciting like mine. I will appreciate if you hold on to your cocks and cunts, because after reading mine, you will surely masturbate. I’m now second married. Thanks to Prem uncle ( 62 years). He has taught me very nice ways to spice up sexual activities in marriage. I was separated from my first drunkard husband and was looking out for a full time job. I didn’t want to be a burden on my brother and sister-in-law. I...

3 years ago
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Passing of SeasonsChapter 9

I wanted desperately to know what had happened to Jenny during those long days I'd spent alone in my room. I began to suspect that it was something bad during that uneasy silence. The hallway that only minutes ago bustled with activity was now strangely quiet. And inside me there was the same quietness. There were no words to say, no way to describe how I felt. But Jenny knew somehow, later I would find out why. I sensed her strength when her hand reached out to help me up off the floor....

3 years ago
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El Paso Jake Rivers

Copyright© Outpost Harry - John Faster than I would have believed possible, my life changed from being a student in the halls of academia in a backward eddy in the flow of the country to nine days of hell in a place incongruously named, "Outpost Harry." I finished my dissertation on "West Texas Gunfighters: Sheriff and Outlaw" and, after the faculty review, I was granted my Masters' degree from Texas Western College. I took off for a month of relaxation at the La Baca ranch...

3 years ago
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Rain Lust

The rain was just beginning to hit the windshield in front of me. That is what we saw as we drove down the road, anticipating what the evening would bring. We had planned this for months, but due to extenuating circumstance and the fickle weather, we hadn’t gone through with our plan. But tonight was the night. As soon as we saw the storm clouds approaching we quickly changed and raced to the car. MY beautiful girlfriend Ann was seated next to me, already breathing heavy. I noticed that she had...

1 year ago
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Sexy Office HR

Hi guys i am Rahul from Pune. I am 24 yrs old workin in a small IT firm. I have been a vivid reader of this site for numerous sex stories. So i thought of sharing my experiences. I had number of experiences but today i ll tell about an exp which i had recently in june. Well i am 5.8 wt 66kg with fair built. I got as an intern at an office in Jan 2011.The office had total 15 people since it was small one. There were two HR Poonam and Ayesha. Poonam was around 35 married with 1 child. Ayesha was...

Erotic
2 years ago
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Dirty Grandpa

Ted was a good grandpa, or at least he tried to be. His grandaughter Shelli and grandson Nick were fun to be with when they were kids, and made him feel younger when he could play with them. As they got older, they really didn't come around as much, but he still enjoyed the time when they did.Nick was now eighteen, and on his way to college, and so he stopped coming to see Ted. So when little Shelli began coming around with her friend Sydney, and they hung around and played at this house, he...

Incest
4 years ago
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The circle of sex

Twenty years ago, my girlfriend and I attended our first swingers part with three older couples. We were new to the group and both of us had a great time. Being the youngest couple, we were very popular and relationships outside the group formed. My girlfriend loved the ‘sugar daddies’ treatment. I had grown very fond of Tammy, she was a spunky 52, tan, nice small firm breasts, chubby, great big ass. I was just 23 at the time, athletic build, and in the best shape of my life. We connected not...

2 years ago
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A Busy Redhead Mom

Episode Two Part One By: Tom’s Mind Just for the record this takes place about one month after my adventure with my aunt Chrissie. One cold December day I was shovelling the snow out of my driveway when I saw my friend’s mom Susan driving off to work. She worked at this really big clothing company and she was really high ranked there. She was in charge of all the shipping and all of the production. Susan was a beautiful woman. She had long curly red hair that went up to her shoulders. She...

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