"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.