A Tale of Two Marital Failures Ch. 01

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Dan gets lucky with his first internet sex connection.
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"Good bye Dan. Take care."

"Yeah, see you later Allen."

Allen was Dan's good buddy. They had known each other for years and DA Tale of Two Marital Failures Ch. 01an had just been over for a beer and some guy time. Dan's wife had walked a month earlier and he was still reeling from the unexpected break up. He had been coming over to Allen's place a lot in the past month, looking for something to take his mind off his empty house. His two sons were with his ex and she was being a real bitch about visitation. His lawyer told him she was just playing hardball, trying to soften him up for a quick and generous separation agreement. A judge had already received a motion to have equal custody but it was going to take time. Until then, Dan just seethed and tried to keep his shattered life from going up in smoke. As he walked to his car, he kicked himself for the hundredth time for not having a pre-nup. Never again, he swore, but that was no help now.

As he drove, he thought about how easy Allen had it. His wife Pat was gorgeous, they were still in love and his job was something he enjoyed. His only child, his daughter Marion, was a model kid. She was just going on thirteen, was a whiz at school, played several sports and never seemed to give her parents any grief. Dan's own two boys were sometimes hellions and now with the separation, they were really acting up. Twice, he had been called to the school to be talked to about proper parenting. 'Fuck you', he mentally said to the councillor who was not much older than the students and knew nothing about raising kids. 'You try it, you silly bitch. Then I'll tell you where you can get off.'

It made him feel a little better to think that at least he was making every effort to keep his boys under control, even if his ex was making that difficult. He had a sudden fantasy of being called into the councillor's office again, bending her over her own desk and giving it to her from behind. 'Damn,' he thought. 't would be a thrill.' Not having had sex for the past month, he was getting a bit antsy in that department. Even Marion had looked good when she came into her father's den, asking for a quick bit of help with her math. He gave his head a shake and tried to forget how he had looked at her in a whole new way, but the image wouldn't go away.

He had known Marion since her birth. He had watched her growing up and now she was becoming a young lady. Despite being just shy of fourteen, she was filling out. She was a tall girl, had long blonde hair, usually in a pony tail and her hips and breasts were coming along nicely. She was going to be a heart breaker next year at high school. Like her mother, she had a beautiful face, perfect skin and natural Hollywood teeth. Allen had commented on how a few of her grade seven class mates, boys, had been "sniffing around". He had just chuckled at that and said his daughter wasn't yet interested in boys.

"And she had better stay that way," was his final opinion on the matter. Dan had refrained from saying anything about the subject as he was inwardly embarrassed at his own carnal thoughts. He had imagined Marion naked in front of him, and he had liked what his imagination had seen.

'Damn', he thought again. 'If I don't get laid soon, I'm going to make an ass of myself'.

When he got home to his empty house, he opened another beer and sat in his easy chair. Newly single, he had to think about what it would take to get laid. He was forty-five, a bit paunchy after years of not paying enough attention to his body and while he had always considered himself to be reasonably handsome, his hair was thinning and a bit of grey had appeared this last year. Never having cheated on his ex, he didn't really remember how to pick up a woman. Money was tight, so going to a hooker was not an option and the thought of paying for sex with someone who might have had sex five times already that night was unappealing. Checking out the bars was an option. And there was always the internet.

He had never signed up for one of those casual sex sites but now it seemed like a good idea. He logged on to the web and entered 'casual sex' into his search engine. Back came thousands of hits. Recognizing one site's name, he clicked on ANightToRemember.com and began the process of getting a membership. Damn, he thought yet again. I'm really doing this. I wonder if this type of a site really works. One way to find out, he thought and made out the online form and gave his credit card number. His ex might find the charge on the monthly statement but so what, he thought. 'What's she going to do? Leave me again?' In only a few seconds he was a paid up member and he paused.

He had to create a profile, and like the site information said, he would do better if he included a picture or two. Feeling silly, he went to the men wanting women section and looked at several male profiles. Names like Stud4U and SexMachine were accompanied by pictures of erect penises and provocative, nude poses. Well, he thought, I have a digital camera and I can always call myself something like 'RetiredPornStar'. No, that was too unreal he thought. With a chuckle and entered 'FreeAtLast'. At least it was an honest nickname, he thought. 'And I can always change it'.

Now for some pictures, he thought. Getting his camera, he looked around the house for a good spot to take them. His bedroom was a mess and he didn't feel like tidying it up. In front of the fireplace, he thought. Perfect. He took off his clothes and feeling a bit awkward, he took some pictures with the timer. They all looked ridiculous. He was posing as if for a family portrait but nude. Going back to the computer, he checked some more male profiles. A few of the guys had managed to look good while nude by taking suitable stances.

He copied some poses he thought better than the rest and was rewarded with two images that seemed acceptable. He had waited for the erect penis shot, not really sure he wanted to include one. In for a penny, he mused and started to massage his shaft. He imagined the school councillor, her skirt up and her panties down, with his hand holding her face down over her desk. He visualized her labia and ass, open to his lust. He saw himself thrusting into her vagina, raping her as she screamed for help. Then, without any conscious desire, his fantasy switched to Marion.

She was nude, sitting on him as he was lying down and she was holding open her labia as she lowered herself to his erect and throbbing cock. His masturbation got more forceful as he imagined her slowly settling over his cock and watched it disappear into her young girl vagina. The reason for his masturbation was forgotten and he imagined her, tight and virginal, slowly allowing his adult penis into her thirteen year old vagina, her face a study in pleasure as she gives up her virginity.

He could almost feel his cock, squeezed by her tight, previously untouched love tunnel, and he was almost ready to come. He imagined her, slowly riding up and down, her tiny breasts flushed with the excitement. He almost heard her moans of pleasure as she gave him her very first fuck. His penis, surrounded not by a young tender vagina, but his own hand, was as thick as it had been in years. His cock head was bulging like it used to do in his own youth. He felt the orgasm rising and it seemed to climb higher than he could ever remember. It was like the feeling he used to get with wet dreams, where the rising pressure and heat seemed to go on and on. He was almost in pain when he felt the spurts of cum shooting out onto the floor. It was the best orgasm he could remember in a decade. He gasped in air and rested against the fireplace mantle.

Covered in sweat, he saw cum drops on the floor, almost six feet away. 'God', he thought, 'I haven't squirted cum that far since high school.' Then he remembered the object of his fantasy. Marion, his good buddy's thirteen year old daughter, the girl who had come into the den only hours earlier for math help, the girl who was still in the seventh grade, the girl who was younger than his own two sons. 'Oh my God', he thought, 'Allen would kill me if he knew what I was thinking. And Pat would kill me, but only after she had gone over me with a baseball bat'.

The taking of erect penis shots was over for the night. He put his clothes back on, cleaned up the evidence of his inappropriate lust and poured himself a stiff belt of scotch. He absentmindedly turned on the TV and channel surfed. Nothing on worth watching he decided and turned it off. His mind went back to Marion and his incredible orgasm. He sipped the liquor and tried to put the images in his head aside. It didn't work. He thought about his rape fantasy with the councillor. He even imagined giving it to her up her ass; raping a young woman in her ass. He paused in his thoughts and wondered why he didn't feel disgusted with himself. Anal rape, sex with a girl not yet into high school, sex with his good buddy's daughter. He shook his head side to side. I really need to get laid, he thought. I need it bad. He sipped more scotch and felt himself rubbing his penis through his pants. Then he glanced at his camera.

Might as well get it over with, he thought, and continued to masturbate. So soon after an orgasm, he expected it would take a while to get hard again. Then he imagined Marion's mouth with his cock head inside. He thickened and lengthened in a minute. 'What is that girl doing to me?' he asked himself as he again took off his clothes.

The thought of Marion giving him a blowjob worked magic. His penis was again fuller and harder than it had been for the last decade with his ex. He took a few pictures, holding the camera himself, then a few more using the timer. Examining the results, he thought that he looked reasonably well endowed. Then, thinking of scale, he took a few more with the scotch glass in his hand, close to his manhood. One looked particularly appealing, he thought. Then, letting the alcohol go to his head, he posed with the timer, taking full body shots, his erection proudly displayed as he sipped the scotch and sucked in his stomach.

Now that looks good, he thought as he looked at the pictures. Back at his computer, he uploaded four. What am I he looking for, he thought as he continued to do a profile. Women, couples, two women; there were several choices. Women will do for now. What did he want? Well that was easy. Discreet encounters. He considered 'A relationship' but thought it unwise. Maybe later, perhaps.

What age group was he interested in? Pre-teens were not a listed option he noticed as yet again, his mind went to Marion. No sense in being stupid and only wanting the young ones. Ages thirty to forty sounded good. Say something about yourself. 'Well', he thought,' honesty might be a good idea', so he wrote a few lines about being newly separated, having two children who were with their mother and wanting to get back into the game. When his profile was complete, he entered it. A message said to log off and re-enter if he wanted his profile to be active. Why not, he thought and did it.

At the site he entered his name and password and he was in. He checked his own profile and saw his pictures. FreeAtLast was online now. He went to women looking for men, chose thirty to forty, within thirty miles. A few seconds later, there were dozens of profiles to peruse. Hot damn, he thought, gleefully. FunGirl4U, FillMe, ILikeItHard and many others were online, cruising for sex. The pictures looked like they could have been lifted from porn sites. Sexy lingerie, nude woman displaying their vaginas, several with toys inserted and many women giving some guy a blowjob, while looking at the camera.

One picture showed a woman lying on a guy, face up with his cock deep in her ass. She didn't look particularly pretty and she could have benefited by losing a few pounds but the picture said it all. If you want to fuck me in my ass, just contact me. Dan was tempted to message her but paused. She might not be a good first choice he thought. Instead he looked for a woman who looked like she had a bit more class. Then he chuckled to himself. He was cruising for sex, not class, but continued going through the profiles.

'TemptationsFlower' caught his eye. Her pictures showed a woman who looked like she was trying to impress without having a dildo in her vagina. Her poses were quite demure compared to the usual and she looked rather attractive. She appeared slim, had long dark hair and her breasts were small. Her age was listed as forty and her profile said she was divorced, had no children and was looking for both discreet encounters and possibly a relationship. Taking a deep breathe, he held his mouse pointer over the 'Send Message' icon and then clicked.

A message line came up and he wondered what to type. His hands were actually shaking slightly with his sudden nervous tension. Wracking his brains, he came up with 'Hello TemptationsFlower. I love your long hair. Do you want to get together?' He had to force his hand to move the mouse pointer over the 'Send' icon. He closed his eyes and clicked. Now he was committed. At least if she was.

He was a ball of nerves as he waited for some kind of response. He thought that she was checking his profile and wondering if he was worth replying to. After what seemed like an eternity, a message popped up. 'TemptationsFlower has sent you a message'. There was an accept icon and an ignore icon. Holy shit, he thought. Maybe she wants me. Or maybe she's going to tell me to fuck off. He clicked 'Accept'.

He almost sighed with relief as he read 'Hi FreeAtLast. I like your picture with the glass beside your very appealing cock. What was in the glass?'

Clicking the 'Reply' icon, he typed 'Scotch, and I just took the picture tonight.'

In under a minute he got back 'New here?'

He thought it best not to pretend otherwise and typed 'Brand new as in just signed up. Forgive me if I'm a bit nervous.'

Back came 'LOL. When I first signed up a month ago I was a wreck. Where are you?"

Wow, he thought, she is interested. Do I give her my address? I might as well, and he did. Back came, 'You and I are only about twenty minutes away? Do you want me to come over?'

Now Dan was seriously shaking. The woman wanted to come over and it was clear that she wanted sex. Go for it, he decided, and sent, 'Yes. Please do that."

n a moment he got back, 'On my way. Don't go anywhere.' Then she logged off.

Dan sat at his computer, staring at the screen. 'Oh my God', he thought. 'This is really happening'. He looked around his house and saw the mess a guy leaves when he doesn't care to clean up. Damn! He almost ran up to his bedroom and tore off the well used sheets, and made it up with clean ones. Hastily, he tidied up, tossing the scattered clothes into the laundry hamper. The en suite was a mess. He did a quick clean up and put out some fresh towels. Downstairs, he buzzed around, making the living room presentable. The kitchen was a disaster. A week's worth of dirty dishes was in the dish washer. He stuffed as many more in as he could and turned it on. Strewn garbage was tossed into the trash and put outside. As he frantically wiped weeks of spills off the counters, he paused and started to laugh. He hadn't been this nervous about an impending encounter since high school.

Judging the kitchen to be adequate, he glanced at the time. She would be arriving in about ten minutes. A mad dash to the bathroom for a fast shower, shave, mouthwash and a touch of after shave and he was at least clean. Finally he put on a reasonably presentable shirt and slacks, his best casual shoes and combed his hair. Back downstairs, he thought about any thing he might have missed. 'Oh my God!', he realized, "I don't have any condoms'. His ex had undergone a tubal ligation. Then the doorbell rang.

He took several deep breathes and opened the door. It was her. "Hello...please come in," he managed to get out. "I'm...uh..."

She smiled, walked in and gave him a quick hello kiss. "I understand how you feel," she said in a warm voice. "About a month ago, I felt the same. Umm...I like your after shave."

She was more attractive in person than in her profile pictures. She was a bit taller than his ex and slimmer as well, with smaller breasts and remarkable eyes. Dan suddenly realized he was staring and he blushed. "It's all right," she said and gave his hand a squeeze. "Any of that scotch left?"

Dan led her into the living room and she sat down in an easy chair. She was wearing an attractive blouse and a long skirt. Her legs were bare and she was in sandals. "You look wonderful," was all he could come up with. "Thank you for coming over. Uh...how do you like your scotch?"

She smiled in a genuine way. "Thank you for having me over. And I like it straight up."

Feeling very much better after getting through the introduction, he poured two ounces into each of his only crystal whisky glasses. Handing one to her, he asked, "Is it all right if I ask you your name?"

She gave him a seductive smile and replied, "TemptationsFlower not good enough?" Then she gave a slight laugh and said, "It's actually Eleanor, but everyone calls me Peaches. Seriously. It's a name from my childhood."

"Okay, Peaches, I'm Dan and I'm very pleased to meet you. And you really have to forgive me for being nervous because...well...I am."

"It's quite all right, Dan. It really is. This is something new for you. I won't bite...unless you want me to."

Dan sat down on the couch and took a big sip of his liquid courage. How the hell I proceed from here, he asked himself. Then he remembered his lack of condoms. Damn. Peaches had brought a purse and he prayed that she was better prepared. They chatted for a few minutes and then Peaches took over. She came over to him and sat down on the couch, one foot under her other thigh. She sat facing him. "I know what you're thinking. We both want the same thing tonight and you aren't sure how to start." She raised her eyebrows, as if saying 'Am I right?'

Dan smiled and nodded yes. "Oh, you're right on with that one. And as long as we're on the subject...I totally forgot about condoms. I haven't needed them for years. I..."

She pointed to her purse on the floor by the chair. "All taken care of. So you can relax." With that she put down her glass, leaned in, took his head in her hands and gave him a slow, sensuous kiss. Dan fumbled to get his drink onto the side table and wrapping his arms around her, pulled her closer and kissed her back.

As if a floodgate had opened, he felt a rush of passion and his hands were all over her. They went up and down her back, her legs, over her butt and she just kept on kissing him. Her tongue was gently probing and he gave it a slight bite. She sighed and then they were French kissing like impassioned lovers. Dan caressed her breast and she held his hand to it, encouraging him. Fingers were fumbling at buttons. As Dan put his hand to her bra covered breast, she undid the front closure and held his hand to her bare skin. Her breast was small but firm, like a much younger woman's. As he played with her nipple, it went hard and she softly moaned. Dan then laid her down on the couch and took a nipple in his mouth.

Her hands were at his pants, undoing the snap and pulling down the zipper. Dan gave a groan as her hand went for his thickening penis. He reached under her skirt and she parted her legs in invitation. He went straight for her panty covered vulva and massaged.

She let out a gasp as he fondled her clitoris. She lifted her hips and he slid down her panties and with her help, got them off. He ran a finger down from her clit, feeling warmth and moisture. A finger slipped inside her vagina, and again she moaned. She was very wet and Dan stroked in side of her, and then added a second finger. Her hand was massaging his penis to full erection. With one hand, he started to take off his pants. Peaches finished the removal and then took off his shorts.