AUTHOR'S NOTE: This story owes a great debt to "Six Times a Day" and its author, spacer_x, along with many others.
-------
Another week went by in the Smyth house with little contact between mother and son. Josh was busy with his job during the day, as was Allie. But while Josh had made it a point to be available in the evenings, Allie seemed to be keeping her distance again. On Monday and Tuesday she texted him to say that she was working late on a project and that he should heat up dinner on his own. Wednesday was something similar, though she said that she was out with some work friends for drinks.
Now it was Thursday, and Josh had barely glimpsed her except in the mornings before they both departed. He had a hard time not staring at her tits as they wobbled dangerously under her blouse. In fact, they'd looked a bit wobblier than usual, but perhaps that was because he'd been so close to them the previous weekend. Their topless massage session had been cut tragically short by a message from Lana. And while the evening had consummated in a tremendous anal sex romp with Lana, part of him wished that she'd left him alone to see where things went with his mother.
Allie, for her part, seemed to have been scared off by the incident, just as Lana had predicted. Things had gone too far. Josh was hesitant where it all might lead, but perhaps less so than his mother. He knew that she must be lonely, alone for so many years after his father had passed. Her vibrator and dildo collection, which he was embarrassingly familiar with, was a testament to that fact.
But they both knew something was building. He suspected that she had watched him masturbate, and he had eavesdropped on her. Twice he had massaged her, and she had partially disrobed the second time so he could not touch, but at least bear witness to her amazing breasts, clad in a lacy bra.
However, the more Allie stayed away, the more he doubted his decisions. She had been shirtless and in his arms. Should he have been bolder? Should he have just grabbed them and squeezed? Maybe she wanted a "real man," like in a porn movie. Should he have torn her clothes off, grabbed her head and guided it to his stiff cock. Or maybe he should never have engaged her in the massage in the first place.
He would have liked to turn to Lana for advice, but she had vanished again, as she seemed prone to do. When he was with her, he felt secure. She was both a guiding force and a willing partner. He was quite aware what she was doing with him ¬-- training him up from a boy to a man. But when they were apart he felt as lost as before he'd met her, perhaps even more so.
Through the week, the absence of both women in his life wore at him, leaving himself alone with nothing but his own thoughts to gnaw on. All these misgivings blurred through his head as he drove home from work on Thursday. Just then a new text hit his cell.
"Won't be home til late. Date tonight. Take some money for pizza." It was from his mother.
He nearly ran off the road when he read the words "date tonight." His mother hadn't had a date, hadn't even mentioned the word "date" for as long as he'd known her. Could she be so desperate to create some distance between them that she'd resort to this?
No, he thought. That's not fair. She deserves some happiness. Then another voice popped into his head: "But I thought that I could be that person."
He had to admit that it was true. He couldn't exactly picture how they would make it work, but in his mind he saw the two of them together, happy and in each other's arms like a married couple. As comfortable eating breakfast together as they were screwing each others brains out in bed.
When he got home, the place felt particularly empty. It had been threatening to rain all day, and the impending storm front was palpably ominous. After a shower and a fruitless half hour hoping to hear Allie come through the door or at least call, he phoned for a pizza, then ate it in silence.
Around nine at night, he tried calling Lana, but only managed her voicemail. He was tempted to go through his mother's dildos again but was afraid that she could be home any minute. Then he thought about going up to his room to jerk off to some porn, but that would prevent him from seeing her when she returned, and he really did want to see her. Not to berate her or interrogate her, but to reassert his presence back into her life somehow. So he settled for sneaking into her room and grabbing a pair of dirty panties from her hamper.
When he brought them to his nose he could smell a deep, feminine musk. It rang the alarm bells in the animal part of his brain and he couldn't help from shoving a hand down his pants just to feel his lengthening cock. He managed to get ahold of himself and wander back down to the living room, where he sat flipping idly through channels while occasionally bringing the panties up to his face. The TV programs zipped by, unseen by his glassed-over eyes. He was lost in a world of thoughts, doubts, and perverted fantasies, a slave to his own bizarre lusts. And feeling how he felt now, he wouldn't have traded it for anything.
Then, just as the eleven o'clock news came on, he heard a car out on the street pull to a stop. He went to the front windows and saw a long sedan parked in front of their house. Was this the date, he wondered. It was took dark to tell, and the forty foot expanse of lawn separating the house from the curb make it difficult to see anything inside. Josh crouched by the window, frozen, waiting for any activity. Then suddenly the car came to life again, backed up, and turned up the driveway.
Without really thinking about it, Josh sprinted across the living room and turned off the TV and lights so the house looked dark inside. Perhaps if his mother thought he was already asleep, he might be able to get a look at the new suitor.
Josh then dashed to a little side entry room off the kitchen that was parallel to the driveway. The car pulled up close, so close Josh had to duck as the occupants looked up towards the window. It was definitely his mother and a man. The man was older, maybe early fifties, though his hair didn't look grey. Josh waited another moment then slowly raised his head to the window. The pair inside was lit by a yellowish light, and he realized that it was the outdoor sconce that hung on side of the house. Positioned as it was, if they looked at the window they would only see a reflection. He could look all he wanted.
Josh stood up and pulled the curtain back to get a better vantage point. Now he could see everything in the front of the car. The man was buff and well-built, with a dress shirt and khaki pants. He had bushy hair, and Josh thought he possessed a certain arrogance as the man laughed raucously at something Allie had said.
Allie was wearing a light jersey dress that showed off a fair amount of cleavage, and was thin enough that he could see the outline of her bra even in this light. He knew the dress well, as he'd noticed it on her before. They seemed to be enjoying themselves, which only annoyed Josh more. They talked for what seemed nearly an hour, but when Josh checked his watch only about fifteen minutes had passed. His legs were getting sore and he wanted to go away, to be anywhere but here, a silent witness to what could be the courtship of his new stepfather.
Then the man rested a hand on Allie's knee. He hoped that she might push it off, but he knew by her body language that it was a welcome gesture. He slid a little closer to her and brushed so hair from her face. The man knew he was doing, Josh had to give him that. He was seducing her in a skilled and practiced way, yet made it look like he was as inept and nervous as she was.
He moved in to kiss her. Josh wanted to bang on the windows, but he knew he couldn't. They kissed, lightly at first, but Josh could tell that they were getting deeper into it. Soon enough, the hand on her knee was sliding up and down her thigh. He moved from kissing her mouth to her neck. Josh could see that her eyes were closed in ecstasy. He slid his hand further up her thigh and her legs parted. Josh could see her panties. The striped pink pair. He knew those panties. This was killing him.
The man continued playing her like a fiddle, hitting her in all the right spots. She was putty in his skillful hands. Then he took her hand, kissed it, and placed it directly on his crotch. She smiled and squeezed, feeling his dick under his pants.
They kissed some more, but Josh noticed that she seemed a bit hesitant to do anymore than give him an over-the-pants rub. She merely continued rubbing it. "That's it," Josh thought, "keep him at bay." But the man would not be daunted by a little shyness on Allie's part. Without pretense, he reached down and unbuckled his pants. A good-sized cock popped up, about six inches and hard as a board. Josh noted this pyrrhic victory, that if a cock was about to be in his mom, at least it was smaller than his.
She took hold of it gently, running her fingers up and down it. The man said something to her with a laugh, then indicated down to his dick. Josh knew, with sick certainly, that this was an invitation. He could not look away as Allie leaned forward, transfixed, and took the cock in her mouth.
It took Josh quite a lot of willpower not to come in his pants, while at the same time not hurl himself out the window to stop the scene in the car. The competing instincts clashed with such force that he ended up pulling his dick out of his pants then running smack into the door. It reverberated with a thud and he was sure that they must have heard him out in the car. He crouched low for a moment, rubbing his forehead, then peered cautiously through the window.
Apparently they had not heard him because his mother was thoroughly involved in her blowjob now. Her luscious lips bobbed up and down on his cock, which was wet with spit. He was clearly enjoying it, as his eyes were closed and his hands were buried in her hair, guiding her up and down.
