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Strings attached

"Jake has a one night stand with an older woman, which comes back to haunt him."

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Sylvia was one of those women guys like to call MILF. Her hair was a mix of dark red and gray, and she was one of those people who barely wrinkled as they aged. She was absolutely beyond all resistance. Perfectly conical breasts, a figure that was both fit and voluptuous, just enough muscle on her toned arms and legs to make her appear strong without detracting even slightly from her feminine charms, and a derriere that instantly attracted attention. Her intense blue eyes took the cake though. I’d be surprised if there was anyone alive with blood flowing through their veins who would not be turned on by her gaze.

Naturally Jake fell for her. It was unexpected, and it happened at one of those football bars, where the Redsox and Yanks are conversation fodder seventy percent of the time, and beer is discussed the remaining thirty percent. She was a smoker, but Jake deducted zero points for that. Smoker, but smoking hot - so he didn't give a damn. He was absolutely smitten with this woman, but he knew that she was probably twenty years his senior. That didn’t really matter though. Anytime doubt entered his mind, he looked into her eyes again and doubt was instantly banished.

It was hard to say who seduced whom. He did more of the moving towards her, but she was a true master of subliminal management. So he moved, and it almost appeared as if she was directing his steps without appearing to on the surface. It wasn’t long after that they departed from the bar, Jake having covered her tab after insisting on it. Their lips were locked together as they stumbled out of the bar.

Jake suggested a motel room in a throaty whisper, as they took a cab, but she didn’t want to do it in a motel room. She wanted to be risky, so they took the cab to a coffee shop near Quincy market. It was only ten pm, so they still had an hour till closing time.

They didn’t order coffee, or even approach the counter. She headed towards the restroom, not leaving his hand. Then she dragged him into the women’s loo. As soon as the room’s door closed behind Jake, they were on each other, tearing off clothes, kissing each other’s body parts, moaning, groaning in an urgent sequence of whispers.

In the cramped space of the women’s bathroom, she made him sit on the commode, while she started out by undressing him from head to toe. Then she slapped him several times, testing out each slap. He was shocked at first, and cried out the first couple of times, but the look on her face stopped him.

He sucked it up and endured the slaps, and he seemed to like them as they went on. She then pulled her black skirt down over her legs, and forced his face into her dripping panties. He tried resisting, but she held him firmly.

After grinding her crotch in his face, she had turned around and made him lick her ass crack. She specially enjoyed this kind of humiliation. She sat on his nose and rubbed the length of her ass up and down his mouth, nose and eyes. She forced him to lick her ass crack again, and pretend he liked it.

She wanted him to ‘pound her vagina’ until she came. That day had been rough at work, so she needed release. She seemed satisfied that he was well endowed, and she felt the large cock throbbing inside her, as she leaned against the door of the restroom and he entered her pussy from behind and below.

She turned around and then leaned against the washbasin instead, so she could look at herself while she was being pounded in the pussy, and so she could look at him, in case he wasn’t paying attention to his job. She held the basin, looked down at it with distaste, and then focused on fixing her hair, as she felt his cock sliding to and fro in her pussy.

Then she turned around, right when his motions sped up, indicating urgency, and asked him to pee. 

He stared at her with disbelief. She slapped him tightly. He glared at her, but she wouldn’t relent.

“Pee,” she said.

It takes a man a while to be able to pee after a full blown erection, so that meant he had to go soft first. So they waited.

It took him a good ten minutes to work it so that he could pee. He kept losing and regaining hardness in stages. Each time he looked at her, his prick became hard again. So he simply closed his eyes and breathed in and out, until he felt the sensation to pee.

He peed, and looked surprised to find a lot of hot pee stored inside him.

When he was done, she started on him again. She played with his balls and clenched them in her palm, as though she wanted to crush. He yelped in pain, but she didn’t relent. The testicles jumped from the point of greatest pressure to a lower pressure point, in her hand. She felt like she was plying with a ball sack that contained hard jello.

Then she clenched her fist over his shaft, and tightened it even more, so that when it tried to swell, she wouldn’t allow it. She held that grip for a good minute, and then moved back to the balls.

He was erect in a few seconds after that. She swirled some spit around in her mouth until it was voluminous enough, and then spit it down on the head of his cock. Then she massaged her dripping saliva, along with whatever pee and pre-cum were left on there, into his foreskin, and into the head itself. She tried forcing her pinky into the opening on the head of his cock, and he cried out from the pain and the suddenness of it.

Then she masturbated him for a few minutes, so that he became harder still.

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She wanted that cum to come back into his balls, from whatever mysterious source it came from.

Then she had forced his enormous penis down her throat, so that her lips were on his balls. She didn’t want to kneel, so she had made him stand on his shoulders so she could blow him. She placed her foot on his ear, and he didn’t complain.

So she forced his upside down dick down her throat, and pursed her lips so that they bit into his balls. She gagged, but she held it there. She moved her head up and down his giant shaft, and kept him in that position for as long as she pleased.

When he begged to turn around, because his shoulders were hurting, she ignored him the first two times. Then she allowed it. He turned over, and she knew that he was almost on the verge of climax. So she went for it. She made him stand on the commode, so she wouldn’t have to kneel, and then she took his manhood into her mouth once more. Her thick saliva coated it and dripped all over her breasts. Then she sucked hard. She sucked his cock, and teased the swollen head and the glans and the frenulum with her abnormally long tongue.

She felt its first quivers in her mouth. Since she was due back at work, she didn’t want cum all over her business casual outfit. So kept it in there. Jake tried removing it, so he could jerk off the last moments before ejaculation. She wouldn’t allow that.

She simply locked her lips around his balls in a vice like grip, and kept sucking. She gagged as she sucked, and felt the penis throb with more determination now, and she felt quakes along the shaft and in his balls. She bit deeper into his balls with her pursed lips, and he let out a scream that she was sure everyone in the coffee shop could have heard.

His thick, salty wad of cum spurted down her throat, and she felt the impulse to retch, but denied it. She heard him scream frantically, but she maintained the grip on his balls with her lips. She felt his hands in her raven hair, pushing her head further onto his cock and balls, and she almost gagged there, with the penis all the way down her throat. But she stayed firm. She would release her grip on his balls until they shrank.

He ejaculated hot spurt after spurt into her throat, and she drank it all. It was a beautiful snack - so much better than anything the coffee shop had to offer. After that, she knew he was done. The weaker spurts hit her now, and she released his balls and withdrew his cock from her mouth. A thick mix of her saliva and his gooey cum dripped down his penis head, and onto the commode cover. She licked his penis head once more, and then gave him an evil smile.

It was a one night stand that got very kinky, and Jake didn’t feel the need to mention the fact that he was cheating on his girlfriend through all of it.

 ***

Steffi wanted him to meet her parents. It’s always exciting meeting your girlfriend’s parents. Actually scratch that. It’s downright terrifying, but Jake was pretending it was exciting, and he kept telling Steffi how excited he was. So there they were, sitting in his Volkswagen Jetta, about to get down. She straightened his tie, and brushed a loose strand of his hair once more.

“Perfect,” she said.

The tension was hanging thick right there, and she appeared tenser than him. They got out, and she rang the ivory colored doorbell with traces of grime. One part of her mind started to fill with a familiar feeling, standing there, outside the home she’d grown up in. Another part was filled with a tumult of expectations. Another simply wanted to lie down and fold up.

She knew that it was interview time. Interview time for both of them as a couple. It was just as much about her as it was about him. They would have a post dinner rehashing of his strengths and weaknesses. Samantha, Steffi’s critical elder sister, would make sure she took a microscope to each and every one of Jake’s faults. She got it from their dad. Their mom was the sweet one, the one that smiled and nodded and tried to make everything reasonable. She didn’t expect trouble there.

Samantha opened the door, and gave Jake a visual once over, while smiling like an executioner at Steffi.

“Hey, you must be Jake,” she said, shaking hands with Jake.

He smiled and nodded.

“And you must be Sam,” he said.

Good, he was paying attention. Steffi gave him approval through eye contact. Samantha preferred the short version of her name from the get go. It was a thing with her, and calling her Samantha was a sure fire way to have an enemy for life.

“Yup, guilty as charged,” she said cheerful for the moment, and led them through an ante room into the living room. “This way folks.”

Jake nearly leaped out of his skin. His mother in law was standing next to the sofa. Her dark red hair with gray in it was glistening with oil, and tied up into a bun. She was every bit the MILF she had been when he had seen her last. Her face had lost all color, as she tried to mask her horror. Jake started trembling, wondering what he could do to control himself. He remembered the slaps, and the kinky domination session, and he saw his entire relationship with Steffi crumbling before his eyes. Such a huge secret wouldn't stay hidden for long.

If you liked what you read, don't forget to like and comment, y'all! It's what keeps writers like me inspired.

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Written by megalanthropus
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