The Midnight Hour

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Ann Douglas
Ann Douglas
3,177 Followers

"Well, would you look at that," Keith heard Lilly said, causing him to pause in his efforts and lift his head from between her legs. "It looks like we have a resurgence of interest."

Keith didn't understand what she was talking about until he followed her gaze down to between his legs and saw that his cock had indeed undergone a resurrection. He'd been so enthralled in what he was doing, he hadn't noticed it at all.

-=-=-=-=-

Lilly guided Keith back to his feet, once more taking his cock in hand. Gently she rolled her fingers along its length, feeling it growing harder at her touch. She leaned forward and closed her mouth around it, sucking on it for a minute or so until she decided it was as ready as it would ever be.

"Showtime," she laughed as it let it fall from between her lips.

As excited as he was, Keith also felt a sudden trepidation as he approached what he knew would be a life changing moment. What if he was a lousy fuck? He couldn't help but recall what she'd said about her ex-husband.

"You're not nervous, are you?" Lilly asked, noting the anxious expression on his face.

"A little bit I, guess," he replied.

"Well, we could stop if you really don't want to do this," she pointed out.

"Oh, I want to do it!" Keith instantly countered, any apprehension instantly fading.

"Then climb on up here, because it's time for Lilly to rock your world," she smiled, not having expected any other answer.

'Now she's going to rock my world?' Keith thought as he moved to comply. 'What does she think she's been doing up to now?'

Lilly stretched out across the length of the couch, spreading her legs to create a gap into which Keith could climb. He'd seen what he knew was called the missionary position in that stag film, so he had a good idea of what he was supposed to do next.

Keith positioned himself above her, wrapping his hand around his cock as he laid the head of it against her mound. Part of him still couldn't believe this was actually happening, that he was about to lose his virginity - and to a woman who had lost hers even before he'd been born.

He felt Lilly's hand against his own, taking control of his cock as she pressed his cockhead against her pussy, rubbing it back and forth until it was covered with the fruits of her arousal. With the slightest of pressures, she used it to part the folds of her sex, then released her hold, ceding control back to him.

Taking a deep breath, Keith pressed forward and slid his hardness into her with surprising ease. The press of her sugar walls as they wrapped around his hardness was heaven itself, producing a greater thrill than he ever could've imagined.

"Oh ... My... God!" Keith gasped as their bodies became one.

A sentiment that was echoed by Lilly in the form of a long, encouraging moan.

Keith began to slowly slide his cock back and forth, penetrating further with each succeeding stroke. Following Lilly's instruction, he took hold of her hips, holding them tightly as he quickly developed a robust rhythm. One in which each new thrust was reciprocated by one of her own.

The pace of their joining quickened, and with it Keith's confidence in what he was doing. He began to pull nearly his full length out of her, only to again enthusiastically press it forward, which seemed to please Lilly even more, given the rise in volume of her cries of delight. Yet even that didn't seem to be enough for her.

"Fuck me, Keith, fuck me harder," the redhead intoned. "I want to feel you all the way inside of me."

Keith didn't know how he could get further inside of her, given that his balls were now slapping against the bottom of her ass, but he was determined to try. Drawing on every bit of youthful vigor that he'd been blessed with, he tried to go faster and somehow, to his amazement, their interaction did seem to grow even more intense.

Slipping a hand between their bodies, Lilly found her clit and began to rub it frantically, supplementing Keith's efforts with her own. At the same time, her other hand moved across her breasts, squeezing them tightly, playing with her nipples until they again grew hard. The dual pleasures, combined with those brought forth by the young man on top of her, quickly carried her to the edge of bliss. A bliss she craved but, at the same time, was not yet ready to embrace.

She reached out and placed her outstretched hands on Keith's chest, causing him to pause in mid-stride. When she explaining what she wanted him to do, the young man happily responded. He rose off the couch, giving her room to turn over onto her stomach, her breasts pressing against a throw pillow by the arm as she raised her lower body up into a kneeling stance.

Once she was done, Keith climbed behind her, guiding his cock back into her. It went in even easier than before and in no time at all he returned to his earlier rhythm. The dark haired teen soon found he liked doing it this way even more than what he was doing before. Lilly certainly seemed to be enjoying it, he thought, content to just lay there and let him slam into her over and over. He felt his heart racing with excitement as Lilly's outcries continued to increase in volume and frequency, calling for him to "drive it home."

Feeling beneath her, Keith found that in this position he could reach her breasts and, even though it forced him to shorten his strokes, he couldn't resist the urge to take hold of them. Lilly didn't seem to mind; in fact, after he'd squeezed them a few times, she retroactively endorsed his actions. Keith knew he was getting close. In fact, if he hadn't already climaxed once, he'd probably have lost it the moment he first entered her. He was just thinking that life didn't get any better than this when Lilly proceeded to prove him wrong.

Once more she forcefully got his attention and directed him to get off of her. This time she was the one who slipped off the couch as he sat down on the center cushion. With her back to him, Lilly climbed onto the sofa and, after taking hold of his cock to hold it steady, impaled herself on it.

With her hands braced against his body, Lilly ground her pussy against his cock, creating a suction that almost brought him to climax right then and there. Slowly, she lifted herself off him, only to reverse herself and drop back down. A process she repeated over and over with increasing speed. The force of her gyrations almost caused her to fall over, a mishap prevented only by Keith's quick grab of her breasts, which in the long run only added to her pleasure.

'So, this is what they mean by riding a cock,' Keith thought as Lilly once more slammed down against him. 'I like it.'

Only a few minutes later, Lilly demonstrated that there was more than one way to do so as, pivoting her body, she turned to face him. She'd slipped off of him and then back on in such a fluid motion that the movement didn't even register on Keith. All he knew was that he was going to explode at any moment.

Lilly seemed well aware of that as well as she pressed her sweat-covered body hard against his, crushing her breasts against his chest as she pulled him deep inside of her. That triggered the inevitable in both of them as, with the walls of her pussy contracting around his cock, they shared nearly simultaneous orgasms. Even as she felt the warmth of his climax fill her, Lilly rode the frenzied waves of her own, bringing their mouths together to share their passion.

-=-=-=-=-

The midnight hour had long passed by the time Lilly and Keith finally finished. They had fucked a second time sometime around two, despite Lilly's earlier emphatic declaration that this had only been a one-time thing. She'd justified her change of heart by qualifying their second go-around as simply an extension of the first. When they still found themselves there at four, Keith had held out hope that there might be a second encore, but Lilly had put that idea to rest with the announcement that they really needed to clean up the mess they had made of Conrad's office. Looking around them, Keith failed to see much in disarray other than a few scattered throw pillows, then got the message. Whatever tonight had been - it was over.

Keith had the holiday off, so he didn't come back to work until Monday. During the interim, he couldn't stop thinking about what had happened and repeatedly hoped that it might happen again. Unfortunately, no sooner had he walked in the door just before the start of his shift than Lilly pulled him aside and reminded him in no uncertain terms that, while it was a memory to be cherished, that's all it could be.

'What's that old saying?' Keith thought to himself as he watched Lilly walk away, admiring the ass he had held so closely only a few days before. 'Better to have fucked and lost than to never to have fucked at all."

He smiled at his own witticism and was about to go and clock in when he was cornered by Pete Malone, who had seen Keith and Lilly talking.

"What's up with old lady Briggs?" Pete asked.

"Nothing really," Keith replied. "She was just letting me know how her son was doing. We used to go to school together, remember?" he added, thinking that it was better to say something rather than nothing.

Pete seemed satisfied with the answer, but, just in case, Keith quickly changed the topic.

"How did things go at your uncle's party?" he inquired.

"I'd rather not talk about it," Pete said.

"That bad, huh?" Keith queried, guessing that things had proceeded pretty much as he had imagined.

"Those girls wouldn't know a good thing if it was standing right in front of them," Pete insisted, not having to add that in his mind it actually was.

"Well, sometimes things don't go the way you hoped they would," Keith commented.

"No kidding," Pete agreed, "but at least my night wasn't as bad as Brooke's."

Having no idea what Pete meant, Keith replied with a 'what are you talking about' look.

"Oh, that's right, you were off yesterday," Pete said. "Evidently, she had convinced Doug to buy tickets to some swanky party up in Manhattan, just off Times Square, in a place where you could see the ball drop. The tickets cost nearly a hundred dollars apiece so, after spending that much, Doug didn't want to also pay to park his car in some high priced garage. So he insisted they take the subway into the city instead."

That actually made sense to Keith, especially if they were planning to drink at the party, which, it being New Year's Eve, was practically a given. He didn't understand why Pete was telling him this, unless of course he'd found out how Brooke had tricked him and wanted to rub it in. But then why had he said her night had been worse than his? Keith didn't have to wait long to find out as Pete had only paused his tale for effect.

"There was an electrical fire down in the subway tunnel between Brooklyn and Manhattan," Pete continued. "No one was hurt, but they lost all the power, stranding the train they were on until almost one o'clock in the morning. Brooke was so angry at Doug over missing the party because he didn't want to pay for parking that she broke up with him - this time for real."

It was clear to Keith that Pete had indeed put the pieces together and knew enough of how Brooke had tricked him to be entitled to say he'd told him so. Thankfully, he was so pleased with the blonde schemer getting her comeuppance, he didn't feel the need to do so.

"Karma's a bitch, isn't it?" Pete said with a broad grin.

"I guess so," Keith smiled in return, feeling a bit of satisfaction with what had happened with Brooke, even though she had unknowingly set the wheels in motion for what had happened.

"Still, it sucks that you wasted your New Year's Eve for nothing," Pete offered.

"Oh, I wouldn't exactly call it a waste," Keith replied, a mischievous glint in his eyes. "Things have a way of balancing out."

END

Ann Douglas
Ann Douglas
3,177 Followers
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BiologoBiologo4 months ago

You wrote: “Another surprise was the color of the rich bush - a mix of brown, gray and even a small touch of white. Suddenly the phrase, 'the carpet doesn't match the drapes', made sense to him.”

I may be wrong but I don’t think that hairs can be gray. What we call gray hair is the result of white hairs (hollow shafts devoid of pigment) mixed with darker colored hairs. Take a close look at a close friend’s and see what you think.

TheOldStudTheOldStudabout 2 years ago

Every Ann Douglas story is spot-on excellent. They're all the ideal length, the characters well developed, and the plots very believable. Her punctuation, at least to my untrained mind, is also perfect, and this is one of the things that makes a great writer in my opinion. Thank you, Ann!!!

gunmakergunmakerover 2 years ago

It's been way to long since I've read your work. Now I'm retired, maybe I'll have more time to enjoy some time reading. Very enjoyable. Well written.

AnonymousAnonymousalmost 3 years ago

"...the carpet doesn’t match the drapes." Priceless! I’ve been around for a long time but never heard that expression before. It is just one more gem in this story’s treasure trove. Wow, what a raconteur, your stories are always sublimely gracious. Thank you.

mason24mason24about 3 years ago

as usual another great story line!

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